When Nichole Wischoff posted an opening at her fund, Neal Mintz reached out to a dozen people who knew her, sent her an Airtable with 10 actionable deals aligned with the thesis, introduced her to several of the companies, and offered to set up her CRM. That was his application. Business Insider wrote about it. People called him a try-hard. He started as a Senior Associate in September 2024. A year later, he was VP.

Neal’s career journey is a story about proving yourself through work instead of credentials and treating every interaction like it matters. It’s also about learning to live with the fact that venture capital’s feedback loops mean you might not know for years if any of it paid off.

Meet Neal Mintz and Wischoff Ventures

Wischoff Ventures is a $50 million pre-seed and seed fund (Fund III) focused on the automation of the real-world economy, spending most of its time in legacy B2B industries across money, movement, manufacturing, and marketplaces. Managing Partner Nichole Wischoff runs the San Francisco side. Neal covers New York. That’s the whole investing team.

Nichole built the firm’s thesis from operator experience. She was early at Blend, part of the founding team at One Finance, and joined construction tech company Built before it reached the growth stage. She started angel investing off that network, raised a small Fund I, a more institutional Fund II, and closed Fund III at $50 million.

The fund writes $1 to $2 million checks, targeting around 10% ownership, usually as the first institutional check in. Current areas of focus include AI-enabled rollups in legacy industries, where companies are building AI-powered versions of services businesses rather than trying to sell software to slow-to-change incumbents. They’re also spending time in critical minerals and mining, and energy infrastructure, where portfolio company Atomic Canyon is building vertical AI for nuclear energy facilities to address the generational knowledge gap as veteran workers retire.

Forging The Path

Neal always had an interest in building businesses and understanding how they scaled. He was the kid in middle school with a duct tape wallet operation. He commuted two hours each way to high school and couldn’t work a formal job, so he started an eBay business. He was president of the entrepreneurship club. The instinct was always there. The exposure to venture was not.

That changed during a couple of summers in Tel Aviv in 2017 and 2018, where he worked in a startup consulting role during the blockchain wave. Watching companies raise capital quickly and make real impact in their industries rewired how he thought about business.

“My perception prior was that the business world is very slow moving. Startups are really the catalyst for meaningful and positive change. Venture is the vehicle that enables them to grow.”

After graduating from Washington University in St. Louis, he spent a year and a half in consulting to understand the inner workings of these sleepy Fortune 500s before leaving to join Fractal Software, a venture studio in New York, where he helped launch B2B Vertical Software Companies. From there, he moved to Ground Up Ventures for a two-year associate program. He was close to leaving for an operating role when Nichole posted the opening.

“I recognize that at a small fund. You’re going to have to be willing to do whatever it takes to help us succeed.”

That philosophy shapes how he thinks about anyone trying to break into venture. The most defensible part of the job is relationships and deal sourcing, especially at the pre-seed and seed stages where companies have no digital presence. “If you just say, ‘Hey, I’m great at diligence and I can research a startup,’ there’s a lot of folks with that same level of intellectual horsepower,” he said.

“It’s the ability to relationship build and be intentional about how you’re doing so in a way that’s adding a ton of value for the firm.”

Automate the Machine, Not the Relationships

Neal is automating as much of his job as he can. Operational tasks like syncing Granola notes with his calendar, email inbox, and HubSpot CRM. Preliminary diligence research like mapping out competitors, their funding, their founders, and their headcount (tasks that used to take hours) now take one prompt. What he won’t automate is anything involving relationships. Outreach, follow-ups, and especially pass emails.

“Treat pass emails with the same level of thoughtfulness as initial outreach.”

He credits Nichole with that advice. He speaks with about 50 companies a month. Wischoff might do one deal a month. That means a lot of passes, and Neal sees everyone as an investment in his network. “The flywheel from those relationships end up paying dividends because I stay top of mind,” he said. “What better way to meet early-stage founders than through founders themselves?”

It connects to a broader principle about reputation in venture.

“It takes one bad conversation to completely destroy your own reputation or get grilled on social media. Whether or not it’s deserved, it’s very important to represent yourself and the firms you’re working for very well.”

The same values show up in how Wischoff works with portfolio companies after investing. Neal’s text messages are half portfolio founders asking for help with office space, hiring, product direction, or financial models. He described a recent night when a San Francisco portfolio company needed help building out their financial model for a seed raise. Neal, in New York, got on the line at 11 p.m. and stayed until 2 a.m. “It’s just our mentality towards everything,” he said.

The Part Nobody Talks About

“I love this job, don’t get me wrong, I have the best job in the world, but it is not always glorious. You are working incredibly hard to meet founders, to chase founders, to diligence opportunities and get a deal done. And very often the deal doesn’t happen for one reason or another.”

Someone else moved faster. Someone else was a better partner. The price didn’t work. You couldn’t convince your team. “You have to be willing to pick yourself back up and keep grinding and working hard,” he said.

The deeper challenge is the feedback loop. In venture, you make an investment and you won’t know for three to five years if it was a great one. The industry operates under the power law, where one or two investments produce the majority of a fund’s returns. If you’re relatively junior and doing roughly one deal a year, the sample size is brutal.

“It’s really hard to know whether or not you’re an exceptional investor early on in your career because of the elongated feedback loops. The likelihood that you find that outcome that ends up returning the fund is very, very slim, and it could be very disheartening.”

He drew a parallel to startup fundraising. VCs put enormous work into deals that fall through, just like founders put enormous work into pitches that end in rejection. But he was honest about the comparison. “I would be lying to myself if I didn’t say startups have it more. They’re in a much more difficult seat because they’re getting a lot more nos.”

It’s the same standard he holds founders to. “They’re raising for the sake of raising when they haven’t gotten themselves to conviction,” he said. Wischoff wants to see that a team has done everything in their power to scale the business before looking for capital. No revenue threshold, no specific milestone. Just proof that the founders have moved as fast as they can with what they have.

It all circles back to the same idea Neal started with: do the work before you have the job, keep doing it after you get it, and understand that the results might take years to show.

“If you want to break in, you have to do a lot of extra work that you’re not going to get paid for. You have to do as much of the job as you can before having it.”

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When Christine Keung was serving as Chief Data Officer for the City of San Jose during the pandemic, she needed a data lake. She wanted Snowflake. She couldn’t get it. The problem wasn’t budget. It wasn’t bureaucracy. The company simply wasn’t trying to sell to the government.

“I didn’t fully appreciate how much selling into the government, especially the Department of Defense, had become a cottage industry dominated by private equity-backed incumbents selling legacy technology. When I became a user and a buyer, I realized many of the core systems and vendors haven’t meaningfully innovated in 20+ years,” Christine said.

The most innovative technology companies in the world didn’t know how to access the largest enterprise buyer in the world: the U.S. government.

That disconnect is the problem J2 Ventures was built to solve. Christine has spent her career on both sides of the transaction. She has been a buyer of technology inside government and a builder of technology at companies like Dropbox and Figma. That dual perspective is the reason she saw the gap clearly enough to act on it.

Meet Christine

Before the Fulbright, before Bridgewater, before City Hall, Christine was employee number one at her parents’ Chinese restaurant in the San Gabriel Valley. She was 11 years old. The restaurant had seven tables, near-zero margins and no formal advertising budget.

What it did have was a kid who understood customer acquisition. Christine negotiated sponsorships with 10 local high school newspapers, trading catered holiday parties for free ad space and menu flyers tucked into newspaper folds. She incentivized Yelp reviews with free egg rolls. The restaurant eventually became the No. 1 most reviewed restaurant on Yelp in a fiercely competitive East Los Angeles dining scene.

“My parents always made me feel like my ideas mattered. I had a real seat at the table growing up, and they empowered me to think creatively, contribute to the business, and actually implement the ideas I believed in.”

That instinct carried forward through roles at Dropbox and Figma, a Fulbright in China and a stint at Ray Dalio’s Bridgewater Associates. Then the pandemic hit. Christine joined the Small Business Administration, where she worked on the $800 billion Paycheck Protection Program as the agency distributed unprecedented amounts of capital to small businesses across the country. It was there that she realized how much government funding existed for entrepreneurs and how poorly it was marketed.

That experience pulled her into public service full time. She served first at the SBA and then as Chief Data Officer for the City of San Jose, where she led data and technology teams and awarded contracts to companies building digital infrastructure for city services during COVID. Those two and a half years inside government changed her trajectory entirely.

“I would not have gone out, joined a general partnership at J2, raised this fund if I didn’t believe in the thesis. It was really my two and a half years in public sector, in government service that convinced me that what we do at J2 has to exist.”

Meet J2

J2 is a venture firm organized around a single thesis: dual-use technology. The firm backs commercial software companies and helps them expand into U.S. government markets. All four general partners have purchased billions of dollars of technology on behalf of the U.S. government. That background is rare in venture capital and central to how J2 wins deals and adds value after writing a check.

The portfolio is concentrated across telecommunications, advanced computing, cybersecurity and healthcare. But it doesn’t look like a typical defense fund. Half the portfolio resembles consumer and women’s health companies. The firm’s first investment was the Oura Ring.

“We don’t invest in pure defense companies. What surprises many people is that some of the most compelling technologies emerging through our military and government partnerships also have incredibly powerful applications in consumer health and women’s health.”

The Most Transparent Enterprise Customer Nobody Is Selling To

The Department of War alone has a $1 trillion budget and that is just federal defense spending. At the state and local level, the footprint is equally massive: state and local government alone accounts for 24 million jobs in the United States. By any measure, the U.S. government is the largest enterprise market in the world.

What surprises most founders, Christine argues, is how transparent that market actually is. Government buyers are required to post competitive bids publicly. Requests for proposals include problem summaries, budget allocations and, in many cases, the direct contact email of the program officer reviewing submissions.

“That level of accessibility barely exists in the private sector. If you’re trying to sell software to a product manager at a major tech company, even finding the right contact can be incredibly difficult. There are multi-billion dollar companies like Clay built around solving that problem.”

Beyond contracts, Christine is focused on helping founders access non-dilutive capital through programs like the Small Business Innovation Research grants administered by the SBA. These grants fund R&D for next-generation technology, from quantum computing to advanced GPS, without requiring founders to give up ownership. Christine believes most founders don’t know this capital exists.

“There is a ton of non-dilutive capital available to entrepreneurs through the government. There are grants, contracts, and funding programs that can be incredibly meaningful for startups. The government just does a very poor job marketing and packaging those opportunities to founders.”

Open-Minded and Assertive at the Same Time

Christine’s approach to evaluating founders was shaped in part by her time at Bridgewater Associates during the era of radical transparency. Every meeting was recorded. Every interaction was rated in real time through an internal app. Employees gave and received continuous feedback called “dots,” and each person carried a “baseball card” of aggregated ratings visible to the entire firm.

“Bridgewater approaches feedback like a big data problem. When you’re processing thousands of signals every week, you develop the discipline to identify patterns instead of over-indexing on any single comment or interaction.”

The principle Christine took from that experience, and the one she now uses as her primary filter for founders, is the ability to be “both open-minded and assertive at the same time.” She describes these as seemingly opposing traits whose continuous tension is the defining requirement for building anything difficult.

In practice, this means Christine looks for founders who hold deep conviction about their market and approach but remain open enough to absorb coaching and act on unstructured signals. She pushes founders to read cues beyond what is explicitly said: body language during customer calls, the outcome of a pitch, the patterns hiding in everyday interactions.

We Can’t All Be Whaling Ships

Christine is direct about what she sees as a structural problem in the venture ecosystem: there is too much venture capital in the market. She frames this through the origin story of the asset class itself. Venture capital was born in the New England whaling industry, where ships were financed with the expectation that most would fail but a single successful catch could return the entire fund.

“Historic levels of venture funding have created a market where even rowboats are financed like whaling ships. Not every company is built to absorb massive amounts of capital, and not every outcome needs to be a billion-dollar outcome.”

She grounds this concern in a specific historical example. During her Fulbright in China in 2014, Christine studied how the first wave of innovative solar companies were all backed by American venture capital. After the 2008 financial crisis, those VCs sold the assets to return capital to their limited partners. Chinese state-owned enterprises acquired the IP. China now controls 96% of the global solar market. The same pattern played out in batteries, telecommunications and critical minerals.

“Most of the core IP and innovation was originally developed in the United States, and it was American venture capital that funded the first generation of these companies. But many of those businesses were ultimately sold, in part because of the return expectations and incentives embedded within the venture model.”

Christine sees this history as part of what informs J2’s approach. When founders layer in government revenue and non-dilutive grants alongside venture capital, they build a more resilient capital base. As Christine put it, “Different forms of capital comes with different sets of expectations that inform the trajectory of your business.” The goal is to help founders avoid a structure where a single source of capital, and its return timeline, dictates the fate of the company.

Where Christine Is Looking Next

J2’s fastest-growing area of investment is workforce technology for the public sector. Christine and her partners have made at least three or four bets in HR, talent and reskilling. One of those is a company called Holly, which Christine describes as “basically Pave for state and local government.” The company helps government agencies hire more competitively. The broader thesis is straightforward: AI should not displace government workers. It should free them from administrative burden so they can do the work they were trained to do.

“Government work is fundamentally human work. You’re dealing with children, families, veterans, and people in moments of real need. But too often, public servants spend the majority of their time buried in administrative tasks, paperwork, and outdated technology instead of doing the work they were actually trained to do.”

Christine sees the future of government technology as a capacity problem. The 24 million state and local government employees in the United States are already there. The opportunity for AI is to remove the operational burden so they can spend more time serving people, not systems.

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In 2021, Andrew Peng was spending his evenings in Discord servers, attending NFT parties, and testing blockchain platforms. He was a first-year MBA student interning at Alpaca VC, and he had decided to go deep on the metaverse because, as he put it, it was early enough that nobody was the expert quite yet. The result was a 60-slide thesis that mapped the emerging space and identified which major tech incumbents had the most at stake. One slide argued that Facebook had “the most to gain and the most to lose” from the metaverse and was therefore the most likely to reposition itself around it. Two months later, Meta launched.

The thesis spread across Twitter, Reddit, and Discord. That moment of virality produced three concrete outcomes: Andrew sourced his first self-originated venture deal, Alpaca’s participation in The Sandbox’s Series B, after the founder reached out having apparently seen the thesis; he landed a full-time role at Alpaca; and he brought in his first LP relationship, a Korean conglomerate looking for managers with a developed view on metaverse and blockchain real estate. He is no longer bullish on the metaverse. But the lesson from that experience became the operating system for everything that followed.

“The lesson wasn’t about the metaverse. It was about how to research a market, how to find founders, how to articulate a point of view, how to earn credibility.”

Andrew believes the most durable edge in venture comes from doing the work others skip before the market prices the opportunity. This conviction informs his thesis on industrial resilience, his sourcing strategy, and his standard for the founders he backs.

From Coal Towns to Cap Tables

The son of immigrants from Shanghai, Andrew grew up across Ohio, Indiana, the mountains of West Virginia, and eventually the DC suburbs. That early geography, he says, informed a lot of his early career choices. He began his career at a boutique consulting firm before leaving at 24 to build out the consulting practice at Smart Growth America, a national nonprofit. There, he advised local governments across more than 40 states on innovation and growth—not just in what he calls “sexy downtowns,” but in places like the ex-coal towns of West Virginia still searching for a 21st-century identity.

He eventually moved into real estate private equity, running acquisitions at a Black-owned firm in DC and closing over $500 million in deals across office, multifamily, and mixed-use properties. That volume was clarifying. “After enough deal volume, you start to see the patterns. I loved deploying capital to shape markets, but I wanted to be closer to the founders and technologies changing how those markets actually work.” He felt farther from innovation. He enrolled in a dual-degree program at Wharton and Harvard Kennedy School and joined Alpaca VC as an intern. He spent four years there as principal and head of research before joining Collide Capital roughly six months ago.

Collide launched its first fund, a $66 million vehicle, in 2022. Fund 2, announced on the homepage of TechCrunch, came in at $95 million, a 50 percent increase, with most original LPs recommitting. The firm is led by two general partners: Aaron, founder of Blavity and AfroTech, the largest Black tech conference globally, who brings the operator lens, and Brian, who came from growth equity at Goldman Sachs and brings institutional investor discipline. The firm invests pre-seed through Series A, focused on fintech, supply chain infrastructure, and the future of work as Gen Z reshapes workforce expectations around communication, flexibility, and trust.

Research Upstream of Conviction

The metaverse thesis matters not because of what it predicted but because of how it was built. For Andrew, research sits upstream of conviction, not downstream of hype. The typical motion looks like this: a theme gets hot, a partner flags it for a house view, someone produces a landscape mapping who is building what, and the work stops before reaching the “so what.“

“By then, maybe the best founders are already funded and prices have moved,” he says. “A lot of research I see is post-rationalization dressed up as thesis formation.”

His version starts before the market has formed a consensus. “If the research doesn’t change who I meet, or what I believe, or what I invest in, then it’s just desk-based, it’s just content, and it’s not connected to actual proprietary sourcing.” As an illustration of how that works in practice, he points to the work he is currently doing on the software development lifecycle. Before forming a thesis, he is already talking directly to engineers and product managers about specific gaps, whether in penetration testing, security workflows, or other underserved parts of the development process. By the time he is sitting across from a founder, he often has relevant customer introductions already in hand. Research and sourcing become the same motion.

This approach extends to how he thinks about the metaverse story in hindsight. He draws a parallel to the dot-com era: “Most of the predictions from the dot-com bubble have come true. People were right. They just weren’t right on timing.” The durability of the lesson matters more than whether the specific call aged well.

“You don’t need to be right forever. You need to show how rigorously you got to conviction at the time.”

The Physical Constraints Software Cannot Fix

Andrew’s most developed market view centers on what he calls industrial resilience, a category built on the premise that the next decade’s bottlenecks will not be solved by writing better code. His years in real estate private equity gave him a ground-level view of an industry that resisted software for a century. He maps that experience onto a broader class of markets: outdated, offline, regulated, or structurally fragmented industries where new enabling technologies are finally creating a wedge.

His specific focus within supply chain and industrial infrastructure is the physical layer that underpins every AI application. Power availability, grid interconnection capacity, rare earth magnets, copper, load forecasting, domestic manufacturing supply, and permitting are the inputs that determine whether AI ambitions scale in practice.

“Anthropic can make software more powerful, but it cannot magically create more substations or faster permitting or make more rare earth magnets or increase our domestic manufacturing supply.”

What makes these opportunities venture-backable, in Andrew’s framework, is a wedge that avoids pure project finance. He looks for repeatable models with some form of nonlinear scaling: proprietary IP, marketplace dynamics with supply-demand liquidity, hardware-software plays, or distributed network models. He also looks closely at founder background. Through pattern recognition across construction tech deals he tracked at Alpaca, he identified that the strongest signal for reaching a Series B in that category was whether the founder came from the construction industry itself. Not pedigree, not cap table composition. Domain origin. Founders who come from the industry bring the relationships, the regulatory expertise, and the technical knowledge that outside competitors cannot easily replicate.

Access Is the Alpha

Collide’s sourcing thesis starts from a straightforward premise: if great products can be built from anywhere, great founders can come from anywhere. If VC firms keep sourcing from the same demo days, accelerators, and networks, they are underwriting consensus. The firm’s Collide Campus Program annually deploys roughly two dozen undergraduate scouts a year at schools like Johns Hopkins University, Vanderbilt, Columbia, and the University of Michigan. These are schools with unicorn outcomes that Andrew believes are dramatically undercovered by institutional venture.

“By the time they have a good idea, I want them to think of us. I want Collide to be the number one name on campus.”

The diversity outcome follows naturally from the access strategy. Collide’s Fund 1 portfolio ended up more than 80 percent led by women, Latin, and Black founders. Andrew is clear that this was not a stated goal. “It’s an output of our strategy,” he says.

“If everyone is sourcing from the same networks and the same schools, you’re going to get the same founder archetype. Great founders are everywhere. It’s just that venture access is not.”

The standard he holds founders to reflects the same principle he applies to himself. He is not looking for polished pitch structures or optimized narrative flows. He is looking for founders who have suffered with the problem and learned something not available from a Google search.

“Don’t just perform venture. Show me the urgency. Show me the pain. Show me what you’ve learned that other people haven’t.”

Embracing the Existential Crisis of VC

When the conversation turned to what he does outside of work, Andrew’s answer was not what most might expect. He goes skydiving and bungee jumping despite being afraid of heights. He scuba dives despite being afraid of open water.

“You have to remember that you can die. That’s what forces you to prioritize why you’re living.”

He did not connect that directly to his work in venture, but the parallel is hard to miss. The same willingness to go somewhere uncomfortable and stay there runs through everything he has described about how he invests.

Andrew describes venture as going through an existential crisis. LPs who feel overcommitted are pulling back, and the result is zombie funds and firms raising smaller consecutive vehicles than they did before. Collide is not in that position. Fund 2 is 50% larger than Fund 1, and that capital, in Andrew’s view, arrives at exactly the right moment. The market is bifurcated. AI is absorbing a disproportionate share of attention and dollars, and consensus opportunities are expensive. What remains, in the places others are not looking, is where he has always done his best work.

“It’s not your job to win every obvious mega round,” he says. “The job of a small firm is to find overlooked markets and founders where the next repricing hasn’t happened yet.”

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There is a version of venture capital that is driven by algorithm. An investor sees someone flip their LinkedIn profile to “stealth mode,” and within hours, an automated outreach tool has offered a term sheet to the top 25% of them. Mercedes Bent has watched this play out and decided to build something that looks almost nothing like it.

“We have become an index play […] and I’m basically doing the anti of that.”

That tension between venture as a relationship craft and venture as an asset-allocation game sits at the center of everything Mercedes is building at Premise, the early-stage firm she co-founded with Vanessa Larco. And the way she is building it is less about a contrarian thesis than a studied conviction that the fundamentals of the job got buried under a decade of hype.

Meet Mercedes, Meet Premise

Mercedes came to venture through a longer and more varied path than most. She worked at the Federal Reserve and Goldman Sachs during the 2008 financial crisis. She founded her own startup. She helped scale other people’s companies from early single-digit teams to organizations of 100 or more. She spent six years as a partner at Lightspeed Venture Partners, where she focused on early-stage investing and ran a scout fund starting in 2020. She also organized some of the first Ruby on Rails meetups in New York back in 2013. All of that shaped what Premise became.

“The last 15 years experience working in tech and in finance and venture capital,” she said. “I feel like it’s all accumulated and driven me to this point where I’m trying to create the VC firm of the future and really the VC firm I wish I had had access to back when I was a startup operator and founder.”

Premise focuses on pre-seed and seed investing, with a particular emphasis on founders in the AI ecosystem. The firm is small by design and deliberate by strategy.

The AI Cycle, Seen Clearly

Mercedes is not a short seller. She said so plainly and more than once. But she is also clear-eyed about what happens when a market gets ahead of itself, and she thinks the current AI moment is doing exactly that.

“The time to push in all of your chips on the table is when you see a huge new unlock for a technology start to happen,” she said. “We’re in a hypey moment of AI, but in the grand scheme of things, this is such early innings. More akin to when mobile was coming out than it is to the end of the mobile cycle, which was like 2021.”

Her concern is not that AI is overstated as a long-term technology. It is that the inflated valuations and accelerated capital deployment of this moment are creating a distorted picture of what these businesses actually look like. She pointed to the potential IPOs of OpenAI and Anthropic as the likely moment of correction. Once lockup periods expire, typically six months after an IPO, public market investors start applying fundamentals-based scrutiny that private market investors have not been required to apply.

“Public market investors are not VCs,” she said. “And they’re just gonna keep looking and saying, so this thing loses how much money for every dollar of revenue it makes.”

She outlined several other potential triggers beyond an IPO correction: large-scale enterprise security incidents, political backlash tied to job displacement, and shifts in public sentiment if unemployment spikes in ways that become visible and politicized. She noted that the U.S. has a presidential election in 2028 and that job loss related to AI automation could become a defining campaign issue if the effects reach beyond the tech sector.

Her read on what early-stage investors should do in this environment is simple: resist the pull to underwrite the exception.

And Drew adds: “A lot of investors have been underwriting the anomaly instead of underwriting the median,” citing cases where investors price companies based on the assumption they will reach $100 million in revenue in seven months.

The discipline is to return to realistic unit economics and to stop letting hype set your expectations.

Building a Deal Flow Engine That Does Not Look Like One

At the center of Premise’s sourcing strategy is Surreal, a community Mercedes started as a monthly dinner series for engineers and AI researchers. The first gathering happened in her living room. It has since moved to art galleries, where attendees sit among large paintings and sculptures and talk about the latest developments in AI research, agent deployment, and model efficiency.

The community now has over 5,200 applicants in the past year, with hundreds of regular attendees. Most of them, Mercedes said, do not know there is a VC behind it. That is the point.

“The minute you’re saying, hey, here’s office hours for VCs, come and talk about your idea, now people are posturing,” she said. “I wanna get to know the real you, who is real-time working out in their head as they’re sitting there, a software engineer at Vercel thinking I might go start a startup one day.”

She thinks about the community through the lens of product design, specifically the sequence of “magic moments” that keep people engaged. The first happens when someone shows up at a dinner, sits down next to a person with remarkably similar interests, and spends two hours in conversation that produces a potential hire, a potential co-founder, and a possible customer. The second hits when they join the Surreal WhatsApp group and discover that 10 people they already know are in it. The third arrives when they post a problem at 11:59 p.m. and someone answers it immediately.

“I want to draw out the magic experience for you to just keep coming back and feeling like it’s amazing,” she said.

The tool running much of the back-end logistics is Luma, which Mercedes described as far better suited for business-oriented community management than the alternatives.

The Behavioral Economics of Good Judgment

Mercedes applies behavioral economics as both a diligence lens and a personal operating discipline. On the diligence side, she looks for founders who understand the emotional architecture of their product.

“The founders who are most in tune with behavioral economics actually build the most magical products.”

If a founder can explain what the user will feel when they sign up, how that cascades through the experience, and how it translates to key performance indicators, that is a signal worth paying attention to.

On the personal side, she uses it to manage her own decision-making. The biggest risk she flags is getting emotionally captured by one part of a deal, usually the founder, and letting that excitement override judgment about everything else.

“I get so excited about founders sometimes on the very first meeting with them and I think it through and I’m like, well, it’s a terrible deal,” she said. “Maybe they’re just good at talking.”

The training is to make sure the founder, the product, the market opportunity, and the deal terms all earn conviction independently. When one of them is missing, the discipline has to override the enthusiasm.

She also flagged the opposite failure mode: letting a deal that worked despite its flaws become a template for future decisions. Chasing an outlier as though it represents a repeatable pattern is, she noted, its own form of cognitive error.

The Long Game, Played Up Close

Mercedes is building Premise for a version of the market that requires patience, presence, and a willingness to know founders long before they are ready to take a meeting with a VC. Her bet is that the firms built on relationship density rather than deal volume will survive cycles better, and will earn the trust of the founders worth backing.

“I wanna see that whole journey with you,” she said. “And have you naturally come to it.”

In a market where capital flows fast and algorithms optimize for reach, that kind of long-horizon, in-person relationship work is genuinely rare. Whether the AI bubble deflates through an IPO correction, a political shift, or something else entirely, Mercedes is positioning Premise to be one of the firms still standing when the next real cycle begins.

This season is supported by SVB. Silicon Valley Bank, a division of First Citizens Bank. Member FDIC. SVB is a trusted collaborator for the founders pushing boundaries and the investors who back them. We’re proud to have them as our sponsor.

Please note, this podcast is for informational purposes and is not investment, financial, or legal advice. The views expressed are those of the speakers and do not necessarily reflect the position of SVB.

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There is a moment in this conversation where Haley Bryant, partner at Hustle Fund, describes almost passing on a company because the founder openly admitted he had no moat. His argument: in a world where software rewrites itself every few months, execution velocity is the only defensible position left. He saw that as a vulnerability. Haley saw it as exactly what she invests in. "I don't agree," she told him, not with the execution velocity point, but with the idea that it wasn't a moat. Execution velocity IS the moat. "That's our thesis. I'm writing you a check."

That moment captures the core tension running through this entire conversation. The traditional frameworks for evaluating early-stage companies (domain pedigree, proprietary technology, clearly defined moats, etc…) are dissolving faster than most investors are willing to admit. What fills the gap is less tidy but, as Haley argues, more honest: a bet on how fast a team can move, adapt, and learn.

The Investor Behind the Thesis

Haley did not arrive at venture through a conventional path. Before joining Hustle Fund, she was angel investing while building a company, advising startups, and working at content agencies and early-stage technology businesses. She describes her early days in venture as a period of real discomfort, specifically around the question of whether to be a generalist or a specialist. “I don’t know if I’m good at shifting focus so much and trying to be kind of the master of none,” she recalls thinking.

What resolved that tension, at least partially, was leaning into something she had always done naturally. Haley grew up overseas, attended a tiny international school where her graduating class included students from roughly 27 countries, and spent her career sitting at every lunch table rather than committing to just one. That instinct toward broad curiosity became a professional asset. At Hustle Fund, where she has now invested across more than 60 companies, it manifests as a portfolio with a clear spike in vertical artificial intelligence, a strong position in small business infrastructure, and a growing focus on capital-intensive markets in the Washington, D.C., region, including cybersecurity, dual-use technology, and energy.

Hustle Fund, for those unfamiliar, operates at the earliest possible entry point. Haley describes it simply: they are the first check in about half of their investments. The fund is generalist in structure but increasingly deliberate in practice, with Haley carving out specific sub-theses she can defend with real pattern recognition rather than informed guessing.

Execution Velocity as the New Underwriting Framework

The most direct expression of Hustle Fund’s current investment philosophy comes from a reference by Vedika Jain at Weekend Fund on the concept of slope. A pitch deck, as Haley frames it, is just a snapshot. What a VC is actually trying to measure is the rate at which a founder moves from one point to the next. “How quickly did they get here, and how quickly will they get to and through the next thing?” she asks. That question, more than any market size slide or competitive landscape chart, is what she is trying to answer.

Roughly 30 percent of companies that receive a first check from Hustle Fund pivot after the investment, and Haley expects that number to accelerate. The implication is uncomfortable for anyone who spent years underwriting businesses on the strength of their initial product or market position: the thing you invest in today may look entirely different in 18 months, and that may actually be a sign of health rather than instability.

She has been deliberately spending more time with teams before making a decision, specifically to observe pace. One example she raises is a company heading into a major fintech conference that she has been tracking for about six weeks without yet signing paperwork. The speed at which they have updated both their product and their investor materials is itself the signal she is watching. “That’s what we’re looking for,” she says.

On the founder character side, Haley is clear about what she is not optimizing for. She wants intensity, but she also cares about emotional intelligence, customer centricity, and the ability to build relationships. Her view is that not every transaction will eventually be executed agent to agent, and the founders who can only operate in automated environments will hit walls that relationship-builders will not.

Fintech as Infrastructure, Not Category

In the conversation, Drew frames fintech not as a vertical but as the invisible operating system running underneath businesses that do not present themselves as fintech companies at all. Haley builds on that and shares her excitement around vertical AI and the idea that once a company gets embedded in a payment flow, the switching cost becomes structural. “Once you’re in those payment flows, it’s a lot harder to rip out,” she notes.

This framing has specific implications for how both investors think about moats in the current environment. Data and distribution still function as defensible positions. Team quality matters more than ever. But what Drew identifies as particularly underappreciated is the unsexy, deep-infrastructure layer of fintech, the parts of how money moves that most generalist investors would not even know to look for. His argument is that those overlooked systems, historically unscalable, are now capable of becoming high-margin, fast-growing businesses precisely because the tooling to build and distribute them has dropped in cost dramatically.

Haley adds a related concern about the era of neo-bank proliferation, where copycat models with slightly differentiated go-to-market strategies crowded every available niche. She and Drew agree that AI has accelerated that pattern across all categories, making it harder to distinguish genuinely venture-scale companies from polished imitations. Haley has started picking up small signals in founder conversations: a founder who talks only about search engine optimization without mentioning answer engine optimization, for instance, is quietly revealing how current their thinking actually is.

Building Pipelines Through Community, Not Hunting

Haley has shifted meaningfully toward community-driven sourcing over the past year. For her, this means socializing deals more openly with trusted co-investors rather than holding a position close until a term sheet is signed. “A few years ago, I wouldn’t have done that,” she admits, explaining that it used to feel risky to signal interest before committing. The logic has reversed: in a market flooded with AI-assisted companies that are easy to build but hard to evaluate, additional perspective from people she trusts reduces risk rather than creating it.

One framework she has become genuinely enthusiastic about is what she calls the consortium model, referencing an unannounced portfolio company. The concept is straightforward: early-stage founders in adjacent spaces form a deliberate network, effectively bringing a complementary ecosystem to enterprise customers rather than showing up as a single point solution. The distribution advantage this creates, particularly in complex markets where trust and relationships drive procurement decisions, is something she expects to see more founders pursue intentionally.

She ties this back to her time before venture, when she was thinking about how to connect customers within a network so they could all benefit from each other’s momentum. “Everything is a network,” she says, and it is the lens she applies to portfolio construction, talent introductions, and co-investor relationships equally.

What Comes Next for Early-Stage Investing

Haley ends the conversation in a reflective mode, acknowledging that six weeks prior, she would have described the investment climate as genuinely unsettling. The question she keeps returning to is both practical and open-ended: what happens if the pace of change accelerates 50 times faster than current projections? What does ambitious even mean in that scenario?

Her answer, at least for now, is to keep orienting toward businesses with real barriers to entry, whether those come from founder networks, proprietary data, or deeply embedded infrastructure. A recent commitment she made to a satellite communications company in D.C., focused on laser-based data transmission as an alternative to radio frequency, reflects exactly that logic. The founder brings rare industry relationships and a specific technical hire that would be nearly impossible for an outsider to replicate. The market is enormous. The why-now is visible to anyone paying attention to where compute is moving.

That combination (a team with genuine access, a problem that requires earned knowledge to even identify, and a market that is large enough to matter) is the kind of bet Haley is increasingly drawn to. The tools to build companies are now available to nearly everyone. The ability to find the right problem and move fast enough to matter remains, for the time being, a genuinely scarce resource.

This season is supported by SVB. Silicon Valley Bank, a division of First Citizens Bank. Member FDIC. SVB is a trusted collaborator for the founders pushing boundaries and the investors who back them. We’re proud to have them as our sponsor. Please note, this podcast is for informational purposes and is not investment, financial, or legal advice. The views expressed are those of the speakers and do not necessarily reflect the position of SVB.

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There is a version of financial services so well-built that nobody notices it is there. No app to open, no form to fill out, no branch to visit. A restaurant owner changes her menu, hires three people, opens a new location, and, somewhere in the background, her banking, lending, and payments infrastructure adjusts automatically to keep pace. The owner never thinks about her finances. She just runs her business.

That is not a distant vision for Bukie Adebo Umeano. It is the investment thesis she has been underwriting for the past four years as an early-stage investor at Anthemis Group. The firm calls it invisible finance, and Bukie has built her entire lens around it, from the structural advantages she believes in to the founders she backs to the unsexy infrastructure plays she gets genuinely excited about. The most powerful version of a thing, she argues, is often the one that quietly disappears.

Iron Sharpens Iron

Before Bukie was an investor, she was a builder. And before she was a builder, she was the second of four sisters, growing up in a household where imprecise thinking had consequences.

“If I say something that makes no sense, they’ll be like, wait, back up,” she said. “They challenge me, they push me. I got in a habit of a good back-and-forth, a healthy debate from a young age.” The four sisters have been called a cult by outsiders and, on at least one occasion, by their own mother, who reportedly turned away from the room after they showed her their welded-on matching bracelets. The bracelets do not come off. Neither, apparently, does the intellectual sparring.

That environment gave Bukie something that proved useful later: the ability to hold a position, defend it under pressure, and let it go when the argument runs out. She admits she still overqualifies her statements at times, a habit she has received feedback on, but the underlying instinct to stay open to being wrong has served her well in every role she has held. “Be open to being incorrect,” she said. “I learned that at a very young age.”

From that household, she moved through consulting and business school before landing in the fintech founding world. That operator experience is what eventually pulled her toward venture. She wanted to be, as she put it, the type of investor she wished she’d had.

What the Founder Side Gets Wrong About VCs

The transition from founder to investor came with a stack of recalibrations. Bukie describes them with the kind of specificity that only comes from having lived on both sides of the table.

As a founder, she could not understand why investors kept pushing on go-to-market so early. The product was good, the early users were there, so why all the questions about scale? On the other side, the logic snapped into focus quickly. “A lot of businesses do well in the first few years, and they reach this point where they can’t actually hit escape velocity,” she said. “Of course, investors try to de-risk that upfront.” If a portfolio keeps stalling at the same inflection point, the investor will start asking that question earlier next time.

Portfolio construction was the other blind spot. Bukie was direct about it: “There are so many great companies that we have not invested in, knowing they were great companies.” A strong business is a necessary condition, not a sufficient one. Ownership thresholds, fund model fit, stage, and check size all factor in before a check gets written. For founders, especially those who do not understand why a VC who loved their pitch still passed, that context matters.

She also noted that every party in a deal answers to someone. “Everybody has a boss,” she said. “Even the person who seems like they have power in a certain dynamic with you, they also have someone that they answer to.” For Bukie, that means the promises made to Anthemis’s limited partners shape every decision she makes as an investor.

The Moat Problem and the Network Effects Standard

At Anthemis, the early-stage fund focuses on pre-seed and seed companies operating in what the firm calls “high assurance” industries: financial services, healthcare, energy, and other categories that are heavily regulated and function as critical infrastructure. Anthemis has been investing in financial services for 15 years, and that experience in one complex regulated space turned out to map across others.

When it comes to evaluating defensibility in those businesses, Bukie is measured about what actually qualifies as a moat. She described most claims to moats as overstated. The one she takes seriously is genuine network effects, and she is precise about the definition. “Why does having company A make it easier, better, or more likely for company B to also be part of this network? Why does company B’s presence make it easier, better, or more likely for company C?” The standard is not just data accumulation. Every company accumulates data now. The question is whether data from one node improves the performance of every other node.

She looks for two things when assessing whether a business can build that kind of structure. First, reinforcing data loops: “Are there reinforcing data loops where one piece of information very closely launches you into the next piece of information?” Second, workflow integration. Businesses that embed themselves in where users already work, whether through technology, a physical environment, or an existing habit, are more likely to build something sticky. The further a product sits from the user’s actual workflow, the harder the network becomes to build and sustain.

The Invisible Finance Thesis, Wave by Wave

The thesis Anthemis developed for its current fund threads through all of this. Bukie described financial services innovation in three distinct waves.

Wave one was digitization: moving from the branch and the phone call to the mobile interface. Think neo-banks, early insurtech apps, the entire first generation of consumer fintech. Wave two was embedded finance: putting financial products at the exact point of need, so a business owner could access lending or payments from within her operating system rather than a separate banking app.

Wave three is what Anthemis is investing in now. “Your financial services are running in the background,” Bukie said. “You, as a business owner, are actually just making decisions.” In her framework, the imaginary founder she tracks through each wave, a restaurant owner she nicknamed “Rosie Restaurateur” in the fund deck, goes from opening a banking app in wave one, to accessing finance within her restaurant’s operating system in wave two, to simply running her business in wave three while the financial infrastructure adjusts behind her. “We don’t think about our electricity, do we? You just walk into a room, you turn on the lights, you never think twice about the fact that the lights work.”

The infrastructure thesis Anthemis is currently writing checks into reflects that directly. She pointed to investments in core banking, rebuilt from the ground up with AI, and in data orchestration platforms, reconstructed the same way. The other category she finds compelling sits at the coordination layer: businesses that unify the growing stack of AI agents and tools that companies are already using, helping them work together rather than creating parallel silos.

On the consumer side, she sees invisible finance building slowly. The business model is harder to crack, go-to-market is expensive, and the data needed to deliver real personalization takes time to accumulate. The founders she finds most interesting in that space are solving for that problem directly: finding ways to generate meaningful user data from day one rather than waiting months or years for the picture to develop.

Betting on the Unsexy

Bukie’s framework keeps returning to a counterintuitive place: the less visible the technology, the more interesting the investment. That applies to the infrastructure she funds, to the businesses she watches become embedded in daily life without anyone noticing, and to the founders who convince people to make decisions that look irrational from the outside because the logic is invisible until it is not.

She is also watching spaces that were historically overlooked become more compelling, specifically because automation cannot reach them. Physical goods, last-mile logistics, anything with a durable analog component: “There are pieces of this that are always going to be in the physical world and can’t be automated away. What automation do we build around that to kind of get us into the next era?”

For Bukie, that question is the right one to be asking. Not where the flashiest opportunity is, but where the work is that will still need to happen regardless of what the technology does next, and who is building the invisible infrastructure to support it.

This season is supported by SVB. Silicon Valley Bank, a division of First Citizens Bank. Member FDIC. SVB is a trusted collaborator for the founders, pushing boundaries and the investors who back them. We’re proud to have them as our sponsor.

Please note, this podcast is for informational purposes and is not investment, financial, or legal advice. The views expressed are those of the speakers and do not necessarily reflect the position of SVB.

Read Bukie’s VC Profile

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There is a pattern inside Harlem Capital’s investment philosophy that shows up everywhere: in the founders they back, the industries they target, and the market conditions they treat as opportunity rather than obstacle. Nicole Tommaso, a principal at the firm, put it plainly during a recent episode of VC Uncovered: “The best returns come from investing in market inefficiencies.” That single idea shapes how she reads a founder’s character, evaluates a company’s defensibility, and decides where the firm will focus its attention when everyone else is looking somewhere else.

Meet Nicole and Harlem Capital

Nicole joined Harlem Capital as an intern and fellow at the tail end of Fund One. Five and a half years later, she holds a principal seat at a firm that has since moved into Fund Two and grown into something that resembles, by her own description, a startup finding its growth stage. “Similar to a startup, everybody was doing everything in the beginning,” she said. “As you think about growth stage, everybody kind of has to focus on what they’re good at.”

Harlem Capital operates as a generalist, early-stage firm writing seed checks between $1 million and $2.5 million. The firm prefers to lead rounds because it wants to stay close to its portfolio companies and provide real operational support. Its recently launched tagline, All Winners Welcome, captures a founding principle that has not shifted even as the broader market conversation around diversity and inclusion has cooled considerably.

“We hate to see what’s happening,” Nicole said, referencing the retreat from DEI commitments across the industry. “But we stay steady. We’re going to do what we did from the beginning.”

Reading the Founder Before Reading the Business

Harlem Capital’s evaluation process at the seed stage leans heavily on character over financials, partly because early-stage companies often don’t have much in the way of financials to evaluate. Nicole described the firm’s approach as one that tries to understand a founder’s internal wiring before ever digging into the business plan.

“Markets are volatile and you need the person who is able to pivot and make things work regardless of the external factors,” she said.

The firm asks founders about their personal histories, how they grew up, and what shaped their thinking. One of its signature questions is deceptively simple: what is the earliest entrepreneurial endeavor you can remember?

“You’ll be surprised that people bring things back to being like 10 years old,” Nicole said. “They’re at recess and they’re selling candies. You know that it’s kind of innate and it’s in them.” The firm also tests for what she calls a “high slope of learning,” the ability to absorb new information quickly and do something with it. In a market where the relevant knowledge base shifts constantly, that quality matters more than any specific domain credential.

She was candid about the risk Harlem is trying to avoid: founders who have jumped onto a moment without a deep-rooted reason to see it through.

“This journey is a lot harder than you think,” she said. “We want to know that this is something that has been so deep in your bones that it’s inevitable.”

Where Software Never Landed

Harlem Capital has developed a formal investment theme it calls “leapfrogging legacy industries,” and it reflects a bet that some of the most durable opportunities in the current market sit inside sectors that traditional software never penetrated.

Nicole explained the logic directly. Many legacy businesses, from trucking to home services to skilled trades, never adopted enterprise software because the learning curve was too steep and the operational disruption too disruptive. They ran on relationships, paper, and phone calls. But AI tools, which generate outputs without requiring users to learn underlying systems, are now reaching these businesses in a way that software never could.

“They could have skipped over software, but now they’ll do AI because it does it for them,” she said. “It doesn’t need them.”

Harlem has already backed one company built around this thesis. Trash Lab is building an AI communications center for truckers, essentially a system that handles dispatch and route optimization through a phone call rather than a dashboard. “Truckers are never going to adopt software,” Nicole said. “They were never going to be on their computer inputting data. But now if they could just pick up the phone and call, AI comms does it for them.”

She also pointed to a broader generational shift. Baby Boomers are handing family-owned and small businesses to Millennials and Gen Z, who are far more comfortable with technology and more willing to invest in AI tools that produce measurable outcomes. That transition, she argued, opens a wide window for venture-backed companies to enter markets that were effectively closed to them a decade ago.

What Makes a Moat in a Zero-Cost Build Environment

Nicole was direct about how the economics of company creation have shifted. The cost of building a product has, by her description, fallen to near zero. Anyone can ship something. That reality changes what a defensible position actually looks like.

“What you have, ultimately, is speed,” she said. “Velocity of learning, velocity of shipping product. And you have data.” Proprietary data access, in her view, is one of the last remaining structural advantages a startup can hold. A competitor can replicate a tool but cannot replicate the training data behind it if that data came from years of specialized industry experience or exclusive partnerships.

The firm is also watching revenue per employee as a meaningful signal at later stages. Nicole cited Lovable as an example worth studying: the company reportedly scaled to $100 million in revenue in a single month with a staff that generated more than $1 million in revenue per person.

“We’re kind of making up new metrics to underwrite businesses now,” she said, “because the landscape has changed completely.”

On the ongoing debate between investing at the application layer versus the infrastructure layer, Nicole took a pragmatic stance. Foundation models will not solve every industry-specific problem on their own. Applications that fine-tune those models using specialized vertical data, she argued, serve a real purpose and deserve serious consideration. The deciding factor, as always, is the founder and whether they have done the customer research to know what they are actually building and for whom.

Building for the Long Game

Nicole closed the conversation with a few personal notes that illuminated how she operates day to day. She uses Claude as a thought partner and pairs it with GenSpark for presentations. Internally, Harlem is building custom Claude projects to automate recurring processes like deal memos, allowing anyone on the team to move through standard workflows without reinventing them each time.

Her wellness habit was equally straightforward: she reads for 30 minutes before bed instead of scrolling. “It turns off my brain,” she said. “It helps me fall asleep pretty instantly.”

The simplicity of that habit fits the larger approach she described throughout the conversation: clear inputs, disciplined habits, and a willingness to go where others are not. When asked what industry she would invest in outside of Harlem’s current focus, she picked consumer and pointed to beauty as a sector that is easy to underestimate and hard to time but powerful when it catches. “When consumer hits, it hits big,” she said.

That instinct, to see value where the math is harder and the outcome less predictable, is what runs through everything Nicole and Harlem Capital are building. The best opportunity, as she sees it, has always been the one that everyone else decided was not worth the effort.

This season is supported by SVB. Silicon Valley Bank, a division of First Citizens Bank. Member FDIC. SVB is a trusted collaborator for the founders pushing boundaries and the investors who back them. We’re proud to have them as our sponsor. Please note, this podcast is for informational purposes and is not investment, financial, or legal advice. The views expressed are those of the speakers and do not necessarily reflect the position of SVB.

Read Nicole’s VC Uncovered Profile

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Connect with Edwin

https://www.linkedin.com/in/edwin-andrade/

Edwin Andrade grew up in the San Fernando Valley without a clear line of sight into venture capital. Nobody in his immediate world worked in tech. Nobody explained what a VC did. When he arrived at Princeton, a first-generation college student who had initially planned on UCLA, he was not just crossing a geographic boundary. He was entering a world that had never been mapped for him.

That experience of discovering what he did not know existed has, by his own account, become the core logic behind how Edwin invests today. “The vast majority of my life has kind of been about uncovering things I didn’t even know existed but were obviously there,” he says. The orientation shapes everything from where he looks for deals to the kind of founder he backs to the physical distance he keeps from the Bay Area’s gravitational pull.

Going on eight years at Core Innovation Capital, he is asking the questions most people are not.

The Uncovered Profile: Edwin’s Ideal State

Edwin lives in Santa Monica with the Pacific in his backyard, but Rio de Janeiro hits differently. His wife is Brazilian and the rhythm of life along Rio's beaches has taken on particular weight since their August wedding. The ideal day begins at the water, chairs small enough to carry, time loose enough to stay a few hours. By evening, sushi and wine, an admittedly unconventional pairing, he has no intention of reconsidering. Then, salsa dancing, which he and his wife have committed to with enough consistency to call themselves genuinely good. The combination, beach by day and dancing by night, is less about luxury than about presence.

The Logic of the Lead

Core Innovation Capital concentrates on seed and Series A, with a bias toward the seed. The fund has stayed deliberately lean, a team of four partners, and has resisted the pull toward later-stage expansion that has reshaped many of its peers. The mandate centers on financial services, healthcare, and insurance, with a specific orientation toward the everyday American consumer, a category that has broadened over time as the financial pressures once associated with lower-income households have steadily moved up the income ladder.

“I don’t need to be the loudest person in the room to stand out,” Edwin says. “I focus on asking the right questions and building conviction.” He is, by his own description, an introvert who has made peace with the demands of a relationship-intensive business by leaning into what that posture actually enables. Listening longer. Synthesizing more carefully. Building trust at a pace that compounds.

The founders that Core backs frequently mirror that quality. Edwin calls them “silent killers,” founders who do not bring the conventional high-voltage energy many investors use as a proxy for conviction, but whose ambition becomes unmistakable if you stay in the conversation long enough and ask the right questions. “I prioritize the ability to inspire and build great products over the desire to chase the title of a venture-backed CEO,” he says.

He was a devoted Kobe Bryant fan growing up. The Mamba Mentality, he says, maps directly onto how he works and what he values in founders.

“It’s about putting in the hours, trusting that they compound over time, and never worrying about someone outworking you. That mindset of quiet, consistent execution is exactly what I look for in founders today.”

Capital as Culture

Core’s stated mission is to unlock wealth and health for the everyday American. Edwin draws a clear line between that orientation and conventional impact investing. Returns come first. In the markets Core targets, that priority and the broader social outcome tend to move together rather than pull against each other.

The reasoning runs through lived experience. Edwin watched his family interact with financial products designed for consumers like them in theory, but rarely in practice. When he joined Core, several portfolio companies were already names his family recognized. That proximity between thesis and personal reality has not faded. If anything, it has sharpened.

The current wave of AI investment is where Edwin parts ways with much of the prevailing narrative. He is skeptical of how evenly the benefits will land. “As this AI wave has kind of hit us all, it’s easy to lose sight of what the typical American is dealing with day to day,” he says. He believes the wealth gap is more likely to widen than narrow in the near term, and he frames that as an investable observation rather than a pessimistic prediction. The companies Core is backing are building toward a world where financial decisions can be automated for people who lack the time, tools, or background to optimize them manually.

One of the portfolio companies, Abode, addresses property taxes. The workflow is nearly entirely automated: a homeowner agrees to engage, the system identifies grounds for a reduction, and the savings arrive with minimal friction on the consumer side. Edwin describes it as a first step toward something larger, a platform that treats the home as a manageable financial asset rather than a static one. The analogy he reaches for is Credit Karma, applied to homeownership.

The broader concept he returns to is agentic automation, technology that does not merely surface information but executes decisions within appropriate guardrails. He is also tracking SMB enablement, specifically how small business owners, many of whom are not highly tech-fluent, can now access tools that remove operational friction at a scale previously unattainable.

The View From Santa Monica

Edwin’s most useful distance from the consensus is geographic and intellectual. Being based in Santa Monica rather than San Francisco is not incidental to his process. “I think the ecosystem would benefit from being less tied to the Bay Area’s craziness,” he says.

“Being based in Santa Monica allows me to step back from the echo chamber and stay grounded when evaluating opportunities. Focusing on fundamentals is where the most meaningful innovation will happen.”

His thinking on fund construction has evolved alongside AI. He is more bullish than ever on small teams. AI has fundamentally changed what two or three people can build and how fast they can move. But he has pulled back from the more extreme version of that thesis.

The solo founder locking up a generational, category-defining company is a harder story to tell today. A lean team can absolutely build a billion-dollar business, but holding the category is a different challenge. The moment you prove out a market, someone will find the capital you left on the table.

“The venture business has never been better structured to fuel outsized outcomes with breakout companies able to access unprecedented amounts of capital.”

Getting to a billion is more achievable than ever. Staying ahead is the bigger problem.

The Founder’s Advocate

One of the less visible dimensions of Edwin’s work is narrative support. The founders Core backs are frequently not the ones building loud public profiles. They are building products. “Many amazing founders are executing well, but are not the first ones to post on LinkedIn because they are focused on the product,” he says.

“As VCs, part of our role is to help them clearly tell their story to other investors, whether that’s refining their narrative, sharpening their deck, or supporting them through diligence.”

There is something specific embedded in that commitment. If your edge as an investor comes from finding founders others overlooked, part of your obligation is making them legible to the next investor in the round. You found them because you ask better questions. Now you have to help them answer the questions others will ask.

Edwin has been asking better questions, in one form or another, since he sat in high school in the Valley, wondering where else to look. The answer has remained consistent: wherever the crowd is not, and wherever the problems are real.

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Connect with Charles

https://www.linkedin.com/in/chudson/

Charles Hudson has a simple theory about where venture capital goes wrong. The best opportunities, he believes, are not hiding in plain sight. They are standing outside the room, unable to get a meeting.

Charles founded Precursor Ventures in 2014 after leaving Uncork Capital, then called Soft Tech, where he had helped back Fitbit, Poshmark, Postmates, and Eventbrite. The financial returns from those early funds gave Uncork the runway to scale significantly, eventually reaching a fund size near $400 million. But as the firm grew, the model changed. Concentrated checks, more board seats, and founders further along. Charles understood why. He just did not want to do it.

“In order to do the kind of work I wanted to do,” he said, “I was going to have to be in a much smaller firm focused on writing those early checks.”

So he left, set up Precursor with a target of $15 to $25 million, and started writing 75 checks per fund to companies most institutional investors would not touch. Eleven years later, the math, as he puts it, feels like it has worked out.

The Uncovered Profile: Charles’s Ideal State

Picture Charles somewhere in Hawaii, a glass of white burgundy nearby, or a Chablis if the afternoon has that kind of ease to it. A Chelsea football match is on a large television, loud enough to feel like you’re right there. His family is around him, his nine-year-old son somewhere in the house, most likely settled into one of the audiobooks he plays through the Sonos system Charles has come to rely on for keeping the household running without interruption.

During the workday, a physical device called Brick sits between Charles and the apps that would otherwise compete for his attention. LinkedIn, Instagram, Threads, and anything else he describes as “doom scrolly” are blocked during working hours by a hardware profile he cannot easily override in the moment. He did not realize how much time he was losing to mindless scrolling until he removed the option entirely. The same intentionality runs through how he thinks about capital, people, and time. Nothing idle. Everything placed with care.

The First-Time Founder Thesis

Charles’s most consistent conviction is one that much of the industry has moved away from: first-time founders are worth backing, and backing them early is worth the ambiguity.

Roughly 70 percent of Precursor’s portfolio companies are started by people who have never done this before. They have not managed budgets. They have not hired or fired anyone. They may not have a product. What Charles is trying to assess is something harder to observe directly.

“How much latent managerial upside and entrepreneurial talent does this person have that hasn’t been utilized in their previous career?” is the question he asks himself when a founder is in front of him. He is, by definition, making forward projections about people who have not yet been tested in the role they are about to take on.

The trait he values most is prior experience in a zero-to-one environment, though he is careful about what that means. It does not require a previous startup. He has backed people who started nonprofits, who led community organizations, and who built things informally. The relevant variable is whether they have opted into the chaos of creating something from nothing, and whether they are prepared to opt back into it.

Domain expertise is relevant roughly half the time. The other half of Precursor’s companies have been started by what Charles calls naive outsiders, founders who looked at an industry without the accumulated assumptions of someone who grew up inside it. In regulated markets, he finds this particularly valuable. People who know all the rules have often internalized those rules as constraints. People who are only vaguely familiar with them sometimes find creative paths that insiders never consider.

The portfolio example he returns to most often is Pair Eyewear, an eyeglasses company he backed when its two founders were 22 years old and freshly out of Stanford. A decade later, they are still running the company, which has scaled to a meaningful revenue level. No management changes are planned. Charles describes this arc as emotionally satisfying in a way that is distinct from a rapid return: finding someone raw and watching them build a sizable business over 10 or 15 years.

The Fund Within the Fund

Precursor’s model is built around a simple but underserved gap. About 60 percent of its activity goes into classic pre-seed rounds, defined as a company’s first investment of $1.5 million or less. Another 25 to 30 percent covers seed rounds in the two- to four-million-dollar range. The remaining 10 percent is a buffer for deals that are simply more expensive, such as a recent investment into a company raising a ten million dollar round at a 40 million dollar valuation, led by an unnamed multi-stage firm, alongside a founder Precursor had previously backed.

The fund’s investment team comprises five people: Charles, three principals, and an associate, with support at any time from two graduate interns. Charles is the sole general partner.

What makes the structure unusual is how he uses authority. A few years ago, Charles gave each principal a dedicated pool of capital they could deploy without his approval, subject to the fund’s LPA guidelines. The explicit goal is to filter for taste, not to teach a framework. If a principal wants to write a check larger than their individual ceiling, they involve Charles, and the deal requires his input. Otherwise, the call is entirely theirs.

“Whatever you pick is what you pick,” he told his team. The result is that the portfolio reflects genuinely distinct sensibilities. One team member turns over high volume, meets many founders, and moves quickly. Another is selective, rarely takes a first meeting, and moves slowly. Both are producing results.

No Standard Mold

Charles has never run a conventional fund and shows little interest in starting. Precursor’s portfolio includes an infant formula company, a women’s ski wear brand, a dog boarding concept that inverted the traditional hotel model, a space communications investment, a nuclear energy company, and what he describes as a “dating glow up” company started by someone he has known for years.

He connects this openness partly to a career that has moved between very different organizational contexts. Before and alongside Precursor, Charles has been involved with In-Q-Tel, the San Francisco Opera, and his alma mater, Stanford, among more than 40 listed engagements. He is candid about not being especially good at stepping back from commitments once he has made them.

What this breadth has given him, in his telling, is a better understanding of how non-startup organizations operate. When portfolio companies sell into universities or government agencies and find themselves frustrated by the pace, Charles can explain why. Those institutions are not broken. They are optimized for different things.

He extends this sensibility to software at large. His view on AI is more restrained than the current enthusiasm suggests. He is long-term constructive on the technology, but believes many of the first-generation application companies are paving a road that others will travel rather than capturing the bulk of the value themselves. His more pointed concern is structural. AI, in his view, is deflationary for software. It shifts value from vendor to consumer in a way the industry has not had to account for before. Products that cost $1,000 today may cost $100 in two years and perform better. Pure software businesses, he believes, face a harder long-term equation than most current valuations reflect.

Playing Their Own Game

Charles is direct about the deliberate choice at the center of Precursor’s model. The current moment in venture has concentrated an unusual share of the industry’s capital in the hands of a small number of large firms. Andreessen Horowitz, Sequoia, Index, Lightspeed, and their peers effectively anoint which companies matter, and a meaningful portion of the industry calibrates its judgment by what those firms choose to pursue.

Precursor sits outside that system by design. The companies Charles is writing checks into are nearly always too early, too unconventional, or too outside established networks to attract attention from large funds whose minimum ownership requirements and fund sizes require a different kind of opportunity. He is clear-eyed about what that requires from him and his team.

“You’re just going to be unpopular for long periods of time,” he said, describing what it means to operate outside the current consensus. “Because many of the things we’re doing are not in the sweet spot of the biggest firms in our industry.” The key, in his view, is understanding which game you are actually playing. Strategies that work for a 250 million fund do not necessarily translate to a multi-billion-dollar platform, and vice versa. Copying a model without understanding its underlying mechanics is a risk in itself.

His advice to the founders he backs mirrors his own position. Have a point of view. Exercise good judgment about what actually matters in a fast-moving environment. Stay adaptable without treating every announcement as a signal worth chasing.

The people he is looking for, at whatever stage they are at, share something simpler. When he asks whether they have found product-market fit, he does not reach for a metric. He asks whether they are up at 11 p.m. because they are anxious and searching for an answer, or because the demand they have created can barely be managed.

Chasing a rock downhill, he calls it. That is the feeling. You can barely keep up.

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Connect with Rachel

https://www.linkedin.com/in/rachelstern/

VC Uncovered’s View

Most venture capital is a race for velocity. Rachel Stern’s work is a study in friction.

At GovTech Ventures, the risk is not that a company fails to find a market; the risk is that the founder lacks the endurance to survive the procurement cycle. In the state and local government sectors, growth is not measured in viral loops or weekly active users. It is measured in the legislative sessions, committee hearings, and the slow, deliberate movement of municipal budgets. Rachel is betting on the “sticky” reality of infrastructure.

Rachel does not view government technology as a subset of defense or federal contracting. She believes that framing ignores the five thousand cities and three thousand counties that manage the actual mechanics of American life. Capital in this space is not a tool for blitz-scaling. It is a strategic input designed to navigate the distance between a pilot program and a multi-year contract. In a market where adoption lags by nearly a decade, Rachel believes durability is the only true competitive advantage.

The Uncovered Profile: Rachel’s Ideal State

The setting is Napa, California, where the light is soft, and the pace is intentionally analog. Rachel is in the kitchen; the air is filled with the scent of fresh vegetables being prepped for a dinner for 10. Her husband is chilling a bottle of champagne, waiting for the precise moment to pour. At her feet, two large, aging doodles are asleep, undisturbed by the music playing in the background. This is a scene defined by hospitality and conversation. There is no performative networking here; there is only the quiet satisfaction of sharing a meal with people she loves, far removed from the theater of the boardroom.

The Geometry of the State Capital

Rachel Stern spent 15 years operating in the fractured landscape of state and local government before she decided to formalize her expertise into a fund. She did not arrive at this niche by accident. She previously founded a firm that transformed a network of state-level lobbyists into a strategic asset for category-defining companies. When Zoom, Lyft, and Square needed to navigate complex regulatory environments, they hired Rachel. She has seen, firsthand, the power of a state to create or destroy a market.

The launch of GovTech Ventures in late 2025 was a response to a specific hole in the venture ecosystem. While billions of dollars flowed into “frontier tech” and federal defense contracts, the mundane systems that manage trash pickup, school funding, and streetlights remained underserved. Rachel is raising a $15 million Fund to address this gap. She is a solo GP focusing on pre-seed and seed stages. She closed the first portion of the fund in December; a second close followed in April.

The logic of her investment thesis is rooted in the customer's “stickiness.” Once a technology is integrated into a government workflow, the churn is remarkably low. Rachel targets companies selling products to state and local governments, where the total addressable market is limited, but retention is nearly absolute. She looks for 80% margins and net revenue retention exceeding 100%. In this corner of the market, a company does not need to be a “unicorn” to be a success.

The Logic of the Lead

Rachel maintains a contrarian stance on federal contracting. She avoids the Department of Defense and the federal government entirely, viewing those markets as governed by fundamentally different buying mechanics. The federal government operates on a 50-year horizon of global dominance. State and local governments operate on one to five-year election cycles. They are concerned with the city’s immediate functionality.

This distinction shapes her fund’s architecture. Because the sales cycle in GovTech can range from six to 18 months, the capital must be patient. Rachel provides her founders with what she calls “optionality.”

“As an investor, I would love to invest in another billion-dollar company; I’ve done that, and I have that track record. But what I’m looking for now is a conversation with my startups that says my goal is to give you the optionality to sell at any point you want. There is no unicorn pressure. If you want to build a billion-dollar company, I will do my best to enable that. But if you want to build a $50 million, $100 million, or $500 million company and sell in the next three years, we can do that too. There are different decisions those companies have to make early.”

The exit environment in GovTech has shifted significantly over the last four years. Large incumbents, such as Cox Media, which acquired OpenGov for $1.8 billion, are actively looking to buy innovation. They are often willing to pay double-digit multiples for startups with less than $10 million in annual recurring revenue. For Rachel’s LPs, many of whom are existing GovTech founders and family offices, this model provides a faster return on invested capital than traditional venture funds.

Capital as Culture

Rachel describes herself as a hands-on investor. She does not merely write checks; she “beats up slide decks” and coaches founders on the nuances of go-to-market strategy. She often spends a month working with a founder before committing to an investment to ensure they are coachable. This is a requirement born of experience. The mistakes in GovTech are expensive and time-consuming; a founder who cannot hear strategic feedback will rarely survive the bureaucracy of a state capital.

Her advice to founders is rooted in a specific metric: 50 conversations. Rachel believes that a founder must talk to at least 50 potential government customers before building a product. She is looking for the “grit” required to navigate systems that are not designed to be navigated. In her view, early traction is defined by three pilots or one solid contract. Once that repeatable motion is found, Rachel uses her network of LPs to help the founder scale from one contract to 20.

This people-to-people approach is a departure from traditional B2B SaaS, where scale is often driven by marketing spend. In government, people buy from people they know. Success in one city often creates a network effect, with neighboring municipalities seeking the same solution. A happy government customer is a founder’s best salesperson; they want to tell their peers about systems that actually work.

The Messy Middle of the AI Era

Rachel has lived through three major cycles of government innovation: the cloud adoption of 2011, the mass digitization of the pandemic, and the current AI era. She is skeptical of “pure AI plays” in the current market. She believes government data is currently too messy for AI to be transformative on its own. Much of the critical data remains trapped in filing cabinets, legacy Microsoft 2003 systems, or analog forms.

“Bad data in, bad data out,” is her guiding principle. She is currently focused on the “messy middle”: companies that help governments digitize analog data sets to prepare for an AI future. She prefers traditional SaaS platforms with integrated AI functionality over speculative AI tools. While governments are eager to keep pace with the private sector, they will always require a “human in the loop.” They cannot simply automate their way out of their workforces.

Rachel also monitors the growing tension between federal and state regulations. While the federal government attempts to prevent states from passing anti-competitive AI legislation, states like Colorado and New Jersey are already moving forward with their own rules. This regulatory vacuum creates a challenge for founders; they are often unsure what they are legally allowed to sell. Rachel’s role is to help them navigate this friction while ensuring their tools remain secure and constituent data remains protected.

The Aesthetic of Durability

Rachel Stern’s work is entirely focused on the tangible. She values the durability of the systems that keep a city running. Her measure of success is not just the financial return for her LPs, but the increased visibility of state and local markets. She wants constituents and investors to pay more attention to the city councils and state senates that dictate daily life.

“Our day-to-day lives are impacted by state and local decisions in a much more profound way than anything happening in Congress. When’s the last time you thought about your city council or who is going to be in your state Senate? We have a level of control over those processes as constituents that we simply don’t have at the federal level. Success for me is getting people to think about those markets as a user, because these are the places where our lives are most directly impacted.” Her personal tools reflect this blend of the digital and the physical. She uses a mix of AI models such as Gemini, ChatGPT, and Claude, to refine her weekly video series on GovTech go-to-market strategies. She finds that bouncing ideas between models helps her maintain her own voice. At home, she is a proponent of Tesla’s Full Self-Drive technology, viewing it as a profound shift in how we interact with our environment.

Ultimately, Rachel is looking for a specific type of person: someone who wants to transform a legacy system that is slow and paper-based. She admires the patience required to work in a market that lags the enterprise by a decade. For Rachel, the work is about more than technology; it is about the grit required to make government function better for the people it serves.

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Connect with Mercedes

https://www.linkedin.com/in/mercedesbent/

The Logic of the Leap

On Sand Hill Road, where nearly every firm markets itself as founder-friendly, Mercedes Bent is building something far more exacting. As the co-founder of Premise, a venture capital firm launched last year, Mercedes is not merely writing checks, she is engineering a community-first ecosystem designed to solve the isolation of the technical founder.

The move comes after a distinguished tenure at Lightspeed and a career that spans the Federal Reserve, Goldman Sachs, and senior operating roles where she helped scale companies to $100 million in annual recurring revenue. Mercedes is a generalist by trade but a behavioral economist by training, possessing a rare ability to identify the irrational heuristics that govern market cycles. While the industry remains fixated on B2B infrastructure, she is looking toward the “new real estate” of AI, in voice-driven consumer applications, prosumer tools, and B2B that spreads bottom-up.

Mercedes is part of a new vanguard of investors who view venture capital as a product rather than a service. Alongside her partner, Vanessa Larco, she is betting that the next generational companies will be built by “spiky” technical founders who prioritize product craft over consensus. In an era of groupthink, Mercedes represents the “discovery” moment for LPs seeking an investor who understands that the highest returns often hide behind the most unpopular opinions.

Meet Mercedes

If you want to understand Mercedes, look to the water. Her ideal day is a split-screen of high-energy connection and literary escapism.

“My happy place is somewhere waterside, Tahoe or Italy, on a boat or a lake house where people are running around and talking.”

Mercedes is a pragmatist who values efficiency, whether she’s using AI to structure voice data or outsourcing her wardrobe to Rent the Runway to avoid the mall. This tech-forward mindset allows her to protect her downtime, which she fills with active mornings on the trail and long-form sci-fi series like Red Rising. For her, a perfect day is defined by community; it starts with a hike, followed by lazing together by or in the water, then cooking a group meal with family and friends, and ends with falling asleep on the couch while watching something together.

The Architecture of Conviction

Premise is built on the belief that venture capital is currently failing the technical founder. Mercedes and her partner have structured the fund to stay small, focusing on pre-seed and seed stages with the intent of becoming a generational firm. The “value-add” here is not a generic platform team, but dedicated IRL communities, such as the engineering and research community called Surreal.

By treating community as a product, Mercedes has created a flywheel for deal flow that bypasses traditional application processes. Surreal brings together future founders and industry leaders, including executives from Anthropic, Roblox, and Character AI, in intimate dinner circles. This architecture reflects her “Hierarchy of Metrics” thesis, which places “customer love” at the base of the pyramid. To Mercedes, product craft is the ultimate signal. She targets founders whose products feel magical on first use, leveraging system design and embedded workflows to create defensibility in an increasingly commoditized AI market.

Market Friction and Contrarian Beliefs

Premise is a generalist firm, however we think the most unpopular opinion Mercedes holds is that firms that ignore consumer are not true generalists and that the consumer software market is not dead. It is being unleashed again thanks to AI. She argues that new technology waves require “new real estate” to thrive. While the mobile wave matured by 2015, resulting in saturated ad networks and algorithmic gatekeeping, AI has opened a new frontier. She identifies voice as a primary new input that expands the surface area of human-computer interaction, creating opportunities that “herdy” investors, blinded by recency bias, are currently overlooking.

This bias extends to the founders themselves. Mercedes points to a systemic failure in the venture ecosystem where investors often make decisions based on whether a founder “looks like a fundraiser.” This groupthink is a significant driver behind the stagnant statistic that only 2% of venture-backed CEOs are women. Mercedes views this not just as a social friction, but as a market inefficiency to be exploited. She prefers to ignore the consensus, instead focusing on “spiky” potential and visceral gut feel, a skill she has honed to avoid the “anti-portfolio” of missed unicorns.

"Most of investors' role is actually making clear non-emotional logical decisions consistently. Those are some of the biggest skills you have to master if you want to be a great investor."

The “Why Now” of the Portfolio

The Premise portfolio is being assembled at the precipice of an AI washout. Mercedes is vocal about her desire for the current AI hype cycle to “pop” sooner rather than later. Her reasoning is tactical, she wants to wash out the “herdy” capital and “hype driven opportunistic product ideas”, leveling the playing field for founders and investors who rely on first-principles thinking and solve real customer problems, rather than looking for a money-grab.

She is currently deploying capital into AI-native tools that serve “power users,” those who demand high-fidelity execution and magical user experiences. Her investment in research labs and prosumer tools is a bet on the “system of record” of the future. By investing in founders who ship fast and obsess over the emotional pull of their products, Mercedes is positioning Premise to lead the post-bubble recovery where utility and craft will once again outrank speculation.

The Capital Horizon

Mercedes is currently focused on identifying the next $100 million in opportunities within the prosumer and AI-native application layers. She remains a software generalist, moving across fintech, dev tools, and B2B app layers, provided the founder exhibits the technical “spikiness” she craves. As the market recalibrates, look for Mercedes to double down on voice-first interfaces and decentralized research labs, areas where she believes the “new land” is still waiting to be titled.

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Connect with Selina

https://www.linkedin.com/in/selinatroesch/

Selina Troesch grew up in Redwood City in the 1990s, when the early internet era made entrepreneurs feel larger than life, and technology felt both nerdy and electric. That proximity to innovation mattered. So did her instinct for numbers.

At NYU, she studied economics and mathematics, with a focus on behavioral economics. She was drawn to where models break down, where bias creeps into financial decisions, and where human behavior disrupts neat theoretical assumptions. That curiosity led her to mortgage-backed securities during the financial crisis, where she was pricing risk at a moment when financial models were under extraordinary strain.

The work was rigorous. It was also clarifying. As intellectually engaging as structured finance was, it did not feel close enough to how individuals and small businesses actually experience the financial system.

She decided to pivot.

Business school became the bridge. During her MBA, she met one of the co-founders of Touchdown Ventures, a firm that partners with large corporations to design and manage venture capital programs. She joined early and spent eight years working across corporate partners, including 20th Century Fox and ScottsMiracle-Gro.

One lesson crystallized during that time. Venture inside a corporation is its own discipline. It is not M&A. It is not business development. It serves a distinct role within an innovation strategy.

That foundation brought her to Intuit Ventures, where she joined a team of three and helped grow the program into a portfolio of nearly 20 companies.

Meet Selina

Q: You can be anywhere eating, drinking, reading. Paint the scene.
A: I’m in a coffee shop in a comfy chair, reading a mystery novel with hot chocolate. If my two-year-old is sitting calmly next to me, that’s even better.

Intuit Ventures

Intuit Ventures focuses primarily on Series B companies, with some flexibility around A and C. Selina is deliberate about why that stage matters.

“For us, Series B is really about companies that have established a solid revenue base, that have evidence of repeat customer behavior where we can assess just how resonant the solution is with customers.”

At that stage, she evaluates expansion behavior, reliance, and whether the product is solving a truly painful problem for consumers or small to mid-sized businesses.

The mandate aligns with Intuit’s broader mission of powering prosperity for consumers and small businesses. Some areas are too close to core products like QuickBooks, TurboTax, Credit Karma, or Mailchimp. Others are adjacent but non-competitive, such as a property tax solution for homeowners. The question is whether the company serves the same customers and advances financial well-being without overlapping directly.

Strategic and financial considerations sit on a spectrum in her view.

The team first evaluates whether a deal works on its own financially. Does the revenue trajectory support a credible return? Only then do they build the strategic case. The investment committee will not approve a deal that fails either test.

The Firewall

One structural feature matters deeply inside a corporate venture unit: the firewall.

Intuit Ventures reports to the same senior leader as corporate development, but sensitive startup data does not cross teams without explicit consent. Financial information shared during diligence stays within the venture team unless the entrepreneur agrees otherwise.

If corporate development expresses interest in a portfolio company, Selina brokers the introduction. She does not serve as a conduit for private information.

The separation protects trust. It also clarifies that the ventures program is designed for insight and collaboration, not acquisition leverage. In her view, the ventures program provides a high-volume, credible signal about what is gaining traction in the market. It is an addition to the innovation toolkit, not a substitute for M&A.

Investment Philosophy

Selina anchors on two dimensions: the customer and the founding team.

On the customer side, she asks whether the company delivers something customers cannot find elsewhere or solves a need in a meaningfully better way. At Series B, execution matters deeply. It is less about pedigree and more about whether a founder’s experiences uniquely position them to tackle this problem at this moment.

The most compelling founders can clearly articulate what they have seen fail before and why today's technology enables a different outcome.

During due diligence, she supplements references with public review platforms such as G2 when appropriate. In direct customer conversations, she listens not just for praise but for hesitation, especially around renewal or expansion. Tone often reveals more than language.

How She Thinks About Risk

As a corporate investor, reputational risk carries particular weight.

If a company could plausibly face regulatory investigation, especially in lending or consumer finance, the bar rises. Intuit’s name will appear prominently in any negative headline. That reality shapes diligence.

She also guards against overcorrection. A failed investment in a category can create internal scar tissue. The harder question is whether that failure reflects structural risk in the category or execution issues specific to one company.

Speed presents another tension. Rounds close quickly. Lead investors move fast. Intuit Ventures does not lead deals, which means Selina often operates on someone else’s timeline.

Her stance is clear:

“I would prefer to miss out than to give up on doing the work that I think is important to understand the risks and opportunities that I am putting capital behind.”

She would rather miss a deal than relax her standards.

Signals and Success

Success at Intuit Ventures is measured across multiple dimensions.

Yes, the team tracks financial metrics such as IRR and MOIC. But they are also evaluated on how effectively they disseminate insight across the organization.

That can mean introducing business units to potential partners, helping corporate development understand a landscape, or flagging patterns such as a cluster of seed-stage companies building in the same space. Even if those companies are small relative to Intuit’s scale, the pattern itself is a signal.

Trends and What’s Ahead

In fintech, Selina sees a post-hype phase. The overinvestment of 2021 and 2022 created a reset. She is wary of products that blur the line between investing and gambling. She believes regulation in financial services exists for a reason.

When companies deal with people’s money, respect for that framework matters.

What interests her is a reframing of personal finance.

Personal finance, she argues, is not an individual sport. It is a team sport.

As financial lives become more intertwined across generations, she is watching companies that help families coordinate and protect their financial well-being. That includes tools that prepare families for children, platforms that support financial literacy for kids, and services that help adult children monitor fraud risks for aging parents.

These companies may be small today. But they reflect a deeper shift in how financial well-being is managed collectively.

Advice to Founders

The window for figuring things out is narrowing.

If a founder intends to build a venture-funded business, the bar for revenue, metrics, and clarity is higher than it was several years ago. Rounds close quickly for companies that hit the right pressure points. When a round lingers, investors ask why.

For founders still refining product-market fit or customer segmentation, that dynamic creates additional pressure. Selina finds it frustrating at times. It also makes her job harder, particularly when operating on compressed timelines.

But her position remains steady. Diligence matters.

A Final Thought

Selina describes herself as someone who sits between cultures. As a first-generation American with parents born in Europe, she is comfortable in nuance. She sees context before absolutes.

That instinct shapes how she invests. Different business models demand different benchmarks. Patterns evolve. Metrics that defined a breakout SaaS company five years ago may not apply today.

In a market that often prizes speed and certainty, Selina moves deliberately. She weighs financial and strategic dimensions carefully, maintains clear boundaries inside a corporate structure, and keeps her attention fixed on the customer.

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Connect with Sherman

https://www.linkedin.com/in/sherman-williams/

The Calculus of Command

In the volatile landscape of deep tech, where the horizon between a laboratory breakthrough and a market-ready product can span decades, Sherman Williams is building a different kind of ledger. As the co-founder of AIN Ventures, Sherman anchors the fluid, often chaotic world of early-stage venture capital with the military's rigid discipline. While the broader market frequently chases the latest SaaS iteration, Sherman is looking toward the stars and the microscopic, anchored by a proprietary internal intelligence system he calls the AIN Brain.

The transition from a syndicate model to a fully institutional fund in 2024 marked a pivotal shift for the firm. Sherman, a Kauffman Fellow who sharpened his financial teeth in M&A investment banking after serving in the military, has designed a fund architecture that treats human potential as a quantifiable asset. By focusing on dual-use technologies, those that serve both government interests and commercial markets, he is betting that the most significant returns lie where national security meets private sector productivity.

Meet Sherman

Sherman Williams lives at the intersection of data-driven discipline and a deep-seated optimism for the future. When he envisions his “happy place,” Sherman is happiest being at the beach with his partner.

However, the true centerpiece of Sherman’s perfect day isn’t the scenery; it’s the dialogue. His mind is rarely far from his core mission: the power of innovation. “I believe technology can change the world,” he says, a mantra that appears on his LinkedIn and drives his career. To Sherman, a day well-spent involves sharing great food and deep conversation with “amazing people,” debating how science and technology can be leveraged to improve the human condition. It is a philosophy of being “present in the present”—recognizing that life is a gift and using his time to ensure the world is better for those who follow.

The Logic of the Lead

The architecture of AIN Ventures is built on a foundation of “data-informed” conviction. Sherman is quick to distinguish this from being purely data-driven, a distinction that allows for the “serendipity of the outlier.” At the pre-seed stage, the firm’s internal weighting is aggressive, assigning the overwhelming majority of its investment decision to the quality of management. The market size and technological differentiation, while important, make up the rest of the investment decision-making calculation.

As a company matures into the seed stage, Sherman shifts the calculus, placing much more emphasis on the market's expected growth and technological differentiation. This shift reflects a belief that, by the seed round, a founder must transition from a visionary to a technician of market penetration. The AIN Brain, the internal AI platform Sherman developed as his Kauffman capstone project, tracks these metrics across hundreds of deals, seeking to identify and eliminate the unconscious biases that often cloud human judgment in the high-stakes world of deep tech.

Market Friction and the Dual-Use Pivot

The “Contrarian Signal” at AIN Ventures is a rejection of the traditional skepticism surrounding government contracts. For years, the venture community viewed government funding as a “kiss of death,” suggesting a lack of commercial viability. Sherman views this as an outdated relic. He argues that dual-use capability is a potent de-risking tool, providing non-dilutive capital and a stable, albeit demanding, anchor customer.

However, Sherman maintains a “commercial-first” philosophy. He expects his portfolio companies to eventually derive the majority of their revenue from the private sector. He treats the government-commercial split not as a balance, but as a series of tactical priorities. Much like the work-life balance debate, he believes that at any given moment, one side must take precedence to ensure the survival of the whole.

“What attracts me to founders are those who can clearly and concisely articulate a gap in a market, why they are uniquely qualified to build for it, and how they will go to market. You have to be able to recruit talent to join you on a crazy, Don Quixote-type experience. That is a skill.”

The Convergence of Space and Life

Sherman is currently deploying capital into two primary frontiers: the orbital economy and the automation of drug discovery. In space, he sees a complete greenfield, driven by the collapsing cost of launch and the rise of on-orbit compute power. He isn’t just looking for rocket companies, but for the infrastructure that will support a multi-planetary species, from lunar logistics to asteroid mining.

Simultaneously, Sherman is focused on the “marginal cost of labor” approaching the “cost of energy.” He believes that AI-driven automation in wet labs will rescue failed drug discoveries and create massive, proprietary data sets that were previously impossible to aggregate. By investing in technologies that increase productivity exponentially, he is positioning AIN Ventures to catch the wave of price deflation that typically follows such massive efficiency gains.

The Capital Horizon

As Sherman looks toward the next $100 million in deployment, he is focused on the global race for Artificial General Intelligence (AGI). He views this race as more consequential than the development of nuclear weapons, with the potential for far greater humanitarian benefit. His focus remains on “FLOPs per second, per kilowatt-hour, per dollar,” seeking the efficiency gains that will allow the United States to lead in AI without compromising the environment. For Sherman, the goal is clear: building the world he wants to live in, one data-informed investment at a time.

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Connect with Demi

https://www.linkedin.com/in/demiladeobayomi/

VC Uncovered’s View

While the common narrative portrays the investor as a central decision-maker, Demi Obayomi operates under the conviction that the actual work is that of a recruiter, community builder, and/or product person. To Demi, the investment is the byproduct of a well-maintained network.

The hardest part of Demi’s day is maintaining a high-velocity filter while navigating the B2B spectrum at Sapphire Ventures, where he evaluates everything from Series B startups to pre-IPO companies. The pressure lies in distinguishing "spiky" outliers from the noise of a saturated market; if he defaults to safe, structured resolutions, he misses the unconventional founders who drive outsized returns. In this high-stakes environment, getting it almost right but failing to take raw action results in the loss of a deal to more agile competitors; movement matters more than a perfect plan.

Demi believes that AI is not an efficiency tool, but a structural shift that will eventually require every individual to operate as their own small business. He believes the most significant transformations will occur when this technology is integrated into the core backbones of the economy like real estate, healthcare, and supply chain; this integration will effectively flatten the ecosystem so that geographic proximity to major tech hubs no longer dictates a founder’s access to capital.

Meet Demi

Q: You can be anywhere. Eating, drinking, and reading your favorite thing. Paint the scene.

A: Some of my happiest moments are always outdoors. I remember a trip to Tahoe with a couple of friends where we skied all day, no breaks. Even though I’m not an amazing skier, the high from that exertion and being outside all day was just incredible; it was a very visceral high.

Key Quotes

“Success is the ability to make other people’s dreams come true.”

“At this point, what I really care about is instinct. I care more about inputs than I do about outputs.”

“The ideal way to practice venture is as a side job. Your main job is being a recruiter, an amazing connector, or a product person; venture is just the way you monetize that network.”

“The very act of doing something and moving yourself closer in that direction is much better than not doing anything at all.”

“I’m looking for the outliers. There’s always been something spiky, or something different about the business, the founder, or the market that we’re invested in.”

Background and Personal Journey

Experiences Shaping My Investment Approach

My transition from Nigeria to an international school in Canada at age 16 gave me a sense of agency that was not as prevalent in a more regimented society. This experience, followed by starting a chocolate company at Johns Hopkins and interacting with the Dorm Room Fund, gave me an appreciation for student-led initiatives and access to capital.

Moment Inspiring Venture Capital Career

The butterfly moment occurred when I drove from Baltimore to Philadelphia to pitch my student startup to the Dorm Room Fund. I was struck by the idea of students making investment decisions to back other students’ ideas. This led me to start A-Level Capital at Johns Hopkins to provide similar access to capital for my own campus community.

Unconventional Belief

I have moved away from being overly structured and rigid towards valuing instinct. I believe that after putting in the proverbial 10,000 hours, following your instincts and trusting your intuition is what ultimately distinguishes you.

Best Advice Received

The idea that raw action solves everything is the best advice I have received. I believe that taking any action to move in a certain direction, even if it does not always work, is better than doing nothing at all. I recently put this into practice by cold-texting alumni of my university to kickstart a tech community event, proving that movement matters more than a perfect plan.

Philosophy and Insights

The Full Spectrum of B2B Growth

I joined Sapphire in 2021 because I wanted to continue pursuing my interest in B2B software, while also having the ability to invest across multiple stages. Now, I look at everything from Series B companies doing single-digit ARR all the way to pre-IPO companies doing hundreds of millions in ARR. It was a logical decision for me to move to a place where I could see that full spectrum of growth.

Identifying Spiky Grassroots Outliers

One great example is Clay.com, which we invested in last year. We’ve seen many go-to-market companies; however, with Clay, there was this incredible grassroots adoption and community love on LinkedIn that we had not seen before. Another is EliseAI; they are doing a fantastic job of bringing AI to specific verticals. They’ve seen great success in the real estate industry and are now expanding that same transformational technology into healthcare.

Investment Philosophy

I would say outliers. I focus on identifying what's spiky or different about a business or a founder. The venture business model is built on finding these unique founders and convincing them to work with you.

The Perfect Founder Pitch

The perfect pitch requires infectious energy from the founder and the ability to clearly verbalize what is unique or different about the business compared to everyone else in the space.

Measuring Success Beyond Returns

Success is the ability to help make other people’s dreams come true. I find fulfillment in helping young, ambitious people realize their visions, such as the students I mentor at A-Level Capital.

Trends and Future Vision

Exciting Trends and Technologies

I am an AI maximalist. I believe AI will eventually require everyone to become their own small business. I am specifically excited about AI applied to verticals like real estate, healthcare, and supply chain, where the technology can transform the core backbones of the economy.

Misconception About VCs

I challenge the idea that venture is a main job. I view venture as a side job used to monetize an excellent network, while the main job is helping founders with recruiting, business development, strategy & insights, etc.

Improving the VC Ecosystem

I want to improve access to capital for those outside of major hubs. Access is not evenly distributed. I want to flatten the ecosystem so that the best ideas can win regardless of whether a founder is in the right circles.

More from Uncovered Media

Connect with Daniel

linkedin.com/in/daniel-ramirez-maz/

VC Uncovered’s View

Investment in deep tech and biotech is not a high-risk gamble on isolated scientific breakthroughs. It is an exercise in platform engineering. For Daniel Ramirez, the goal is not to fund a single "lucky" discovery, but to back underlying transformational technologies that can expand across multiple use cases and markets. The same principle applies to software. 10VC operates on the reality that large value pools lie in the creation and development of transformational platforms. 

The operational reality at 10VC is defined by high-touch concentration rather than high-volume betting. In the early institutional stage, getting it "almost right" is often a prelude to failure; a founder who lacks the muscle memory to pivot based on feedback or fails to de-risk key milestones quickly will hit a wall that capital alone cannot fix. Daniel acts as an "agile athlete," moving across verticals and business problems, leveraging his international exposure as an investor, management consultant, and corporate executive. The hardest part of his day involves the intensive work of "making the decision right" after the check is written, engaging with founders bi-weekly to navigate the friction of early-stage growth where any lapse in alignment can stall a platform’s momentum.

Daniel holds a conviction that the current hierarchy of the tech stack is nearing a total inversion. He believes that the massive, standalone platforms dominating today’s headlines are destined to become mere features of the more specialized, integrated mega platforms of tomorrow.

Meet Daniel

Q: You can be anywhere. Eating, drinking, and reading your favorite thing. What is it?

A: My favorite moments correlate with family; we are a family of four, and when we share time and everybody is fully present, the energy that can be felt in the air fills me up. California nature also fills me up significantly. I also enjoy traveling, engaging with people from different backgrounds, and learning what they like.

Key Quotes

“Our philosophy -and I think this is pretty important: try to make the right decision and then try to make your decision right. That changes a lot the way you invest. Once you invest, you have to work on it.”

“We get as involved as possible. We believe we can de-risk or help the companies de-risk their own business. For that reason, we dedicate a lot of time to founders.”

“AI is changing the whole thing. One trend that excites me a lot is that the platforms of today are going to be the features of the platforms of tomorrow.”

“What we want to see is platform thinking. They know already where to expand and how to expand. The more you know your customer, the more likely you are going to have PMF.”

“Interconnectivity is the biggest area for improvement in the Venture Ecosystem.”

Original Responses (Lightly Edited for Clarity and Flow)

Background and Personal Journey

Experiences Shaping My Investment Approach

My path started as an industrial engineer. Upon graduation, I joined McKinsey and Company, where I spent time working with banks, petroleum firms, and insurance providers. Later, I served as an innovation director at the Coca-Cola Company. My journey eventually led me to a Danish pharmaceutical company where I helped create digital health startups in Copenhagen. This journey naturally opened the door to an invitation to lead a small venture capital fund; I view every experience as a source of growth and value.

The Moment That Inspired My Venture Career

Life usually takes me to new places rather than me following a strict, intentional plan. The opportunity to start 10VC alongside Ben Patterson arrived at the perfect time. Ben possesses an extraordinary track record and a wonderful personality. Silicon Valley felt like the ideal landscape for this mission; there is no better place on earth to build a fund of this nature.

Influences on My Worldview

Close family ties shape my perspective. Happy moments are almost always tied to time spent with my wife, daughters, parents,siblings, in-laws,etc. Nature and travel also provide significant energy. I enjoy engaging with people from various backgrounds and learning about different ways of life; this openness allows me to connect with founders from all walks of life.

An Unconventional Belief

In the world of corporate venture capital, success comes from identifying things that are low cost for the corporation but high value for the startup. Problems arise when firms promise high-cost initiatives that they will rarely risk for a minor equity stake. When you focus on low-cost synergies that provide massive value to the founder, the model works beautifully.

The Best Advice Received

Our core philosophy is to try to make the right decision and then try to make your decision right. This mindset shifts how you approach an investment; you cannot simply write a check and walk away. Once you commit, you work alongside the founder to ensure the partnership reaches its full potential.

Philosophy and Insights

Investment Philosophy

We focus on the very early stages. We are typically the first institutional partners to join a round; our strategy centers on investing in platforms rather than isolated products.

Why We Choose Concentration Over Volume

We chose a concentrated model because we believe in getting as involved as possible to help companies de-risk their own business. Unlike a typical pre-seed fund that might spread bets across many companies, we write larger checks and dedicate significant time to our founders. We view our investments as long-term partnerships; once we invest, we work like crazy to pave the way for the founder. We believe that if we can help the company succeed through this high-touch approach, everyone wins.

Defining the Boundaries of a Generalist Scope

While we are generalists covering B2B, B2C, deep tech, and life sciences, we do have clear limitations. We avoid areas like crypto and NFTs, and generally stay away from VR or AR. We also avoid single-point or single-asset solutions like a pharma company with only one asset or a single-use medical device. We are looking for platforms with an expansive mindset rather than isolated products. If it is just business model innovation without a unique underlying technology, we typically pass on those opportunities.

Values When Working with Founders

We prioritize de-risking the business through deep involvement. We dedicate a significant amount of time to our founders; most of our portfolio companies choose to chat with us every other week. We want to be the support system they rely on during the early days of building.

Betting on High-Efficiency Academic Founders

Since we do deep tech and biotech, we often work with PhDs and scientists who may not have traditional entrepreneurial muscle memory yet. What we look for in these individuals is a hyper-efficient mindset and a big ambition. We love to see founders who have made massive progress no matter what, even before they have incorporated or raised money. That drive to keep moving forward, combined with a willingness to listen to external feedback, is a great predictor of success.

The Perfect Founder Pitch

The perfect pitch is the one that clearly conveys this message: unstoppable team building an interesting solution to solve a really big problem. In our context,a perfect pitch also demonstrates platform thinking. I want to see that a founder understands how to expand into new use cases, markets and technologies. Platform thinking implies deep customer knowledge, which leads to a higher likelihood of finding product-market fit. I also value founders who listen to feedback. Startups move through short life cycles, and those who can incorporate external perspectives avoid hitting the same wall twice.

Approach to Risk

We look for companies that can do a lot with a little (capital efficient). Their goal should be to find paths to growth that require less capital to reach major milestones; this efficiency often allows companies to become sustainable and enables an exit to happen sooner.

Measuring Success Beyond Returns

We serve as a bridge between our LPs and the entrepreneurs. Success means serving both groups effectively; when a company succeeds and changes its industry, everyone involved finds satisfaction. That is our primary mission and this is my first priority. My second priority is that I should become a better person while executing the first priority.

Trends and Future Vision

Exciting Trends and Technologies

Artificial Intelligence is redefining every industry. I believe the major platforms of today will become the basic features of tomorrow’s systems. These systems are what we call the giant vertical or horizontal automation platforms. In addition, we think that the combination of multimodal AI with other breakthrough technologies can rewrite the rules of each vertical allowing new challengers to gain significant market share in massive industries.

Misconceptions About VC Innovation

A common misunderstanding involves the nature of synergies in CVC. Corporations will not risk their multi-billion dollar brands for a startup where they hold a minor stake. Real innovation happens when CVCs facilitate access to assets that are low-cost for the Corporation but provide breakthrough value for the startup.

Improving the Venture Ecosystem

Interconnectivity is the biggest area for improvement. Many founders struggle because they lack access to the right investors and sometimes enter suboptimal partnerships just to survive. On the other hand, we -as investors- would love to meet more companies. If we could strengthen the links between these two groups, the entire ecosystem would benefit.

Challenges for Early-Stage Founders

The Early Stage landscape is going through deep changes and founders need insiders who are willing to share the necessary insights that will help them navigate successfully. There are a lot of bad outcomes that can be avoided by making the right decisions early.

More from Uncovered Media

Atlas Berry (M1C)

Read the VC Uncovered Profile:
https://www.vcuncovered.com/p/atlas-berry-m1c

In this Episode

Drew Glover talks to Atlas Berry from Mission One Capital (M1C) on the “physical AI” revolution and the industrial infrastructure required to power it.

Atlas, the founder of M1C, explains that the U.S. power grid is facing a “comfort crisis,” currently unable to meet the massive energy demands of AI. He positions M1C as a specialist partner focusing on three pillars: energy, industrial resilience, and earth systems. By prioritizing “behind the meter” power generation and Virtual Power Plants (VPPs), the firm aims to build a decentralized, resilient power landscape that can operate independently of the traditional, strained grid.

The conversation takes a compelling turn as Atlas shares his transition from high-stakes investment banking in South African mines—where meetings required security sweeps for explosives—to managing the global footprint of Linkin Park. These high-pressure environments, coupled with early venture experience backing companies like Lyft and Snap, shaped his “performance protocol” for evaluating the next generation of industrial founders.

The episode is particularly insightful when he discusses the “Misogi”: an annual challenge with a 50% chance of failure designed to recalibrate a founder’s mental and physical endurance. Atlas argues that building in hard-tech is an endurance sport, requiring “battle-tested” individuals from military or elite engineering backgrounds. He cautions that in an infrastructure-heavy future, specialized VCs must act as more than just capital providers, serving as deep value-add partners for those solving tangible, world-scale problems.

Sponsor:

This season is supported by SVB. Silicon Valley Bank, a division of First Citizens Bank. Member FDIC. SVB is a trusted collaborator for the founders pushing boundaries and the investors who back them. We’re proud to have them as our sponsor.

Please note, this podcast is for informational purposes and is not investment, financial, or legal advice. The views expressed are those of the speakers and do not necessarily reflect the position of SVB.

More from Uncovered Media

Connect with Itamar

https://www.linkedin.com/in/itamarnovick/

VC Uncovered’s View

Success in the current AI cycle is not about participating in the infrastructure gold rush; it is about identifying the application-layer survivors. While the common narrative suggests that the real value lies in the massive capital expenditures of AI infrastructure, Itamar Novick and Recursive Ventures operate on the reality that we are currently navigating an infrastructure bubble; one that mirrors the 1999 Cisco era before the inevitable correction. For Itamar, the goal is not to fund the "routers" of the AI age, but to back the "services-as-software" platforms that will emerge from the burst with exclusive, defensible data moats.

The operational reality at Recursive is defined by the high-velocity precision of a "solo capitalist" model; a structure designed to eliminate the friction of committee-based decision-making. In a market where founders now "seed-strap" companies with lean teams and agentic workflows, getting it "almost right" means backing a team that lacks the architectural foresight to build a "winner-take-most" dynamic. The hardest part of Itamar's day is the rigorous filtering of execution risk; he leans heavily toward repeat entrepreneurs because he understands that the "trail of fire" inherent in scaling to a $5 billion IPO leaves no room for first-time muscle memory errors. If a founder cannot demonstrate a marginal cost that trends toward zero while owning a unique data set, the business fails the "venture scale" test.

Itamar holds a sobering conviction regarding the immediate future of the ecosystem; he anticipates that the current AI infrastructure bubble will burst in 2026 or 2027. He believes this correction will fundamentally erode the advantages of old SaaS systems of record, giving rise to a new frontier where AI accounting firms and automated enterprises do 99 percent of the work with near-perfect accuracy.

Meet Itamar

Q: You can be anywhere. Eating, drinking, and reading your favorite thing. Paint the scene.

A: I am a huge traveler. I spent a year in India backpacking; another six months in Latin America with my wife; and months backpacking in Australia. We skip the Four Seasons; it is about the experience and genuine connections with people. When I am not traveling, I tinker. I am a geek who wrote my first line of code at 11. I have over 250 connected devices in my home and I love playing with everything; installing it, fixing it, and sending bug reports.

Key Quotes

“The ones that really go big are companies that get to a one winner take most dynamic.”

“AI can eclipse SaaS and take over a lot of what SaaS is capable of doing; it is a pivotal point for venture capital.”

“If you’re talking to Recursive, you’re talking to me; a person who just finished building a 5 billion dollar company.”

“I believe we are in an AI infrastructure bubble. I think it will burst in 2026 or 2027.”

“Go dig up the unsuccessful companies that shut down and ask those founders what happened. That is when people expose their true face.”

Background and Personal Journey

Influential Experiences

I have been in startups for 25 years on all sides of the table. I am a serial entrepreneur and executive who took my last company, Life360, public at a 5 billion dollar market cap. I started as VP of Product and ended up as the CFO who took it public. I even borrowed 2x my net worth to buy out a co-founder early on. Before that, I was at Gigya, one of the first SaaS companies. Having built engineering, product, sales, and support teams from scratch gives me a superpower in supporting founders. I have a high-level understanding of every single thing they need to build to be successful.

The Inspiration

My VC career actually started on Sand Hill Road as a senior associate at Morgenthaler Ventures, which is now Canvas Prime. I was there from 2010 to 2012; a storied old-school firm where we were in companies like Lending Club, Evernote, and MuleSoft. That is where I really landed the role of venture capital. From there, I started angel investing and set up an accelerator called UpWest to bring Israeli companies to the Bay Area. I have been deploying capital for 15 years now.

The Solo GP Superpower

I believe solo GPs are the best partners for founders. When you talk to Recursive, you are talking to a single decision-maker who has actually built something real. In bigger partnerships, the dynamics can be negative for founders; you show up to a Monday morning meeting where four other partners who do not know your business throw random questions at you. As a solo GP, I can make a decision in a day. I can make contrarian bets on crazy ideas that a committee would turn down; and those often end up being the best investments of my career.

Unconventional Belief

I believe venture capital is under threat by AI. The whole model is going to change completely. We are entering an era of seed-strapping where founders can raise 1 million or 2 million dollars and build what used to take a 100 million dollar check. With vibe coding and 10x engineers, you do not need 50 engineers and 20 salespeople anymore. This is a fundamental shift in technology that erodes the advantages of old systems of record.

Intuition vs. Data

I am institutionalized in the sense that I have a rigorous process, but I live for intuition. There are three things that are a absolute no-go for me: Team, TAM, and Moat. If I am not blown away by the people, I am not doing the deal; everything else is secondary. In pre-seed, your ability to diligence only goes so far because there are typically no customers. I rely on soft signals; who sent me the deal, what have they built, and what is their founder-market fit.

Philosophy and Insights

Principles for Founders

I am a little bit of a unique VC because I do not pretend to know how to run a founder’s business better than they do. I am friendly, helpful, or I get out of the way. I do not take board seats. My founders call me when “S hits the wall,” whether it is founders fighting or board issues. I have raised over 500 million dollars and built a public company board; I use that experience to be there for my founders when things get aggressive.

Practical Back-Channeling Tactics

My word of advice for founders is to never take money from a VC without back-channeling them first. Do not just talk to the successful companies they give you as references. Go dig up the unsuccessful ones that shut down and ask those founders what happened. How a VC deals with the downside when things are bad is the only way to understand who you are actually partnering with.

The Perfect Pitch

I look for a strategic long-term advantage; a moat. If you are building a product, can you generate unique, exclusive data sets that help you continuously improve your AI? I want to see a business where the marginal cost of servicing one more user trends to zero. If you can show me a path where, 10 or 20 years from now, you are making 500 million to a billion dollars in revenue because you own the market, that is venture scale.

Approach to Risk

I do not like taking execution risk. That is why two-thirds of my deals are with successfully repeat entrepreneurs. There is so much risk in startups already; I cannot back people who do not know how to build stuff. I also lean away from “blue ocean” projects that might have a market 10 years from now. I would much rather invest in a disruptive business model that caters to an existing large market where I know the TAM is real.

Trends and Future Vision

Emerging Trends

I am operating under the assumption that we are in an AI infrastructure bubble that will burst in 2026 or 2027. We are in 1999; Cisco was worth a trillion dollars for building routers, then it blew up, but Google and Amazon came out of it. I am focused on the application layer. I see three big areas: consumer AI rewriting human-machine interaction; agentic automation in the enterprise; and services-as-software. We are going to have AI accounting firms that do 99 percent of the work accurately. That is the next frontier.

VC Misconception

VCs get too much credit. I give all the credit to the entrepreneurs. We are just here to finance them and make sure they do not do really stupid stuff. The general audience thinks VCs help these companies come together and win, but that is a misconception. It is the founders doing it; we just need to give them money and get out of the way.

Systemic Improvement

I would kill preferred shares at the seed stage. It is controversial, but preferred shares make it more complicated for everyone. Venture is governed by the power law; if I get my 1x back on an investment, it does not move the needle for me or my LPs. We are really there for the 100x returners. By slapping on protections that you do not need at the early stage, we are just slowing things down.

The Founder Challenge

The biggest challenge for first-time founders is the “trail of fire” they have to go through. They have to learn everything from scratch; like how to let go of half a team or manage a board. Second-time founders have already gone through those ups and downs. VCs can help by being the first call when things go wrong and providing a narrative for subsequent funding rounds. I have supported over 25 startups in graduating to Series A because I know what the next level of investors is looking for.

More from Uncovered Media

Connect with Ahmad

https://www.linkedin.com/in/ahmadjtahir/

Ahmad Tahir didn’t arrive in venture capital chasing the role. He arrived after watching how companies actually behave when conditions change, and realizing that most investment theory only makes sense once you’ve lived through a few cycles yourself.

He began his career in investment banking in the shadow of the financial crisis. Like many people graduating at that moment, the path he imagined didn’t exist in the form he expected. Wall Street roles were scarce, and opportunity looked different than it had just a few years earlier. Ahmad took a banking role in Cleveland, not because it was the destination he had planned, but because it was where the work was. That decision, taking what was available and committing fully to it, set the tone for much of what followed.

From banking, Ahmad moved into corporate development roles across multiple industries, including energy, IT services, and technology. He joined companies at different stages, in different markets, and across very different points in the economic cycle. He experienced what it feels like to operate inside an organization when markets are expanding, capital is flowing, and optimism drives decision-making. He also saw the other side: what happens when conditions tighten, priorities shift, and leadership decisions suddenly matter a great deal more.

Those experiences fundamentally shaped how Ahmad evaluates businesses today. Rather than relying on abstract frameworks, he looks for patterns he has seen repeat over time. He has watched strong management teams adapt and survive downturns. He has also seen organizations with early advantages slowly lose ground because they failed to evolve. That kind of pattern recognition doesn’t come from spreadsheets alone, it comes from proximity to the work.

At Moderne Ventures, Ahmad brings that operating awareness into every investment conversation. He tends to focus first on the people. Ideas matter, but only in the hands of teams who can execute under real-world constraints. Having spent years in corporate development seats, Ahmad understands the complexity of aligning product, engineering, finance, and go-to-market teams, especially as companies grow. That vantage point allows him to identify not just what a company is doing well, but what might break later if left unaddressed.

His emphasis on multivertical businesses emerged naturally from that background. After seeing how cyclical industries like real estate, energy, and finance behave during downturns, Ahmad became cautious of companies built to serve only a single market. In his view, products that can apply across industries offer more than growth potential, they offer resilience. When one sector slows, flexibility can mean survival. Multivertical design buys founders time to adjust, refine, and continue building even as conditions change.

Geography plays a subtle role in how Ahmad operates. Based in Chicago, he sits outside the intensity of the Bay Area while remaining closely connected to it. He spends significant time in San Francisco and New York, but values the distance enough to preserve independent judgment. Being in the Midwest allows him to slow decisions down, pressure-test assumptions, and avoid the momentum-driven dynamics that can emerge when everyone is chasing the same companies at the same time. It’s not about avoiding competition—it’s about maintaining clarity.

One of the most defining aspects of Ahmad’s approach is how he treats relationships. Venture, in his view, is a deeply human business. If he can’t invest in a company, he introduces the founder to someone who might. He keeps a running list of investors he trusts and shares opportunities openly. That generosity isn’t transactional, it’s how he operates. Over time, it creates better conversations, stronger deal flow, and mutual trust with founders and peers alike.

For Ahmad, venture capital isn’t about having the perfect answer or predicting the future with precision. It’s about being honest about what you’ve seen, being thoughtful about risk, and staying close enough to operators and founders that your advice is grounded in lived experience.

Meet Ahmad

Q: You can be anywhere eating, drinking, reading. Paint the scene.

A: I’m with my wife and kids at a restaurant on the beach in Kauai.

How Ahmad Thinks About Venture

Experiences Shaping My Investment Approach

Ahmad’s interest in investing was first sparked during his freshman year when his cousin gave him Warren Buffett’s autobiography. He found the process of evaluating businesses fascinating, noting that it closely resembled solving a puzzle.

The turning point occurred during his junior year at Indiana University while enrolled in an investing class. Ahmad entered a stock investing competition, applying the frameworks he had learned from Buffett’s book to his own evaluations. After his use of these methods resulted in a competition win, the experience of seeing those frameworks lead to successful stock selection solidified his interest in the field.

What He Looks for in Founders

Ahmad starts with execution. He looks for founders who can take something from zero to one, who understand the problem they’re solving, have a credible reason for being the ones to solve it, and can sell the vision to customers, employees, and future investors. Ideas evolve. Teams determine outcomes.

How He Thinks About Risk

Having seen how quickly conditions can change across multiple industries, Ahmad favors companies designed with flexibility in mind. Multivertical products reduce dependence on a single market and give founders room to maneuver when external forces shift.

He’ll lean into uncertainty if he believes the team, market structure, and timing give him a shot at a power‑law outcome, but avoids avoidable risks like weak founding teams, misaligned incentives, or unclear ownership.

Advice He Gives Most Often

“Investors don’t just back ideas—they back traction, learning velocity, and ability to execute under uncertainty. It’s not about having the perfect plan; it’s about testing hypotheses fast, learning faster, and adjusting direction before the market moves.”

Unconventional Belief

Ahmad observes that some VCs still underprice or stay away from "hard pivots." He finds that founders who cleanly kill a prior idea, remain open and honest with their teams, and rebuild around a sharper wedge illustrate sharp decision-making skills. In many cases, he views these founders as more investable.

Trends and What’s Ahead

Ahmad is particularly interested in:

• AI tools that dramatically accelerate research and internal workflows.

• Payment infrastructure built on crypto and stablecoins, especially for large transactions like rent and mortgages.

• Cybersecurity, as the rise of generative and “shadow AI” introduces new vulnerabilities into legacy systems.

Across all of these areas, he looks for practical adoption, not just technical novelty.

A Final Thought

The most common misconception about venture capital is that it’s purely intellectual. In reality, it’s relational. The best outcomes come from trust, collaboration, and sustained engagement, not just sharp analysis.

Ahmad believes the ecosystem would benefit from more openness: more conversations, more shared ideas, and more willingness to slow down and think together. Venture works best when investors stay grounded in experience and remember that behind every company is a group of people trying to build something durable.

More From Uncovered Media

Connect with Natan

https://www.linkedin.com/in/natan-reddy/

VC Uncovered’s View

The world of making and moving things often feels invisible to the everyday person. But for Natan Reddy, this world is at the forefront every day at industrial-focused VC fund, Ironspring Ventures. Before Ironspring Ventures, Natan was at CB Insights tracking how blockchain might revolutionize maritime shipping or how sensors could optimize a factory floor, eventually establishing and leading supply chain innovation research at the firm. 

Now a Principal at Ironspring Ventures in the NYC office, Natan represents the nimble, sector-focused investor who chooses depth over breadth. Ironspring operates as a specialized VC fund  for the digital industrial world; the firm focuses on the backbone of the global economy: manufacturing, construction, transport & logistics, and alternative energy.

He understands that you cannot simply apply a software-as-a-service playbook to a construction site or a factory floor. These industries have slow sales cycles and long-standing ways of working. Success here requires what Natan calls “industry DNA.” By investing in early-stage rounds, Ironspring acts as a catalyst across legacy industrial industries and pioneering founders taking on complex challenges to modernize these critical sectors

The relevance of Natan’s work today is clearer than ever. With nearshoring trends bringing manufacturing closer to home and the urgent need for supply chain resiliency as well as increasing physical infrastructure and energy demands fueled by the AI boom, the industrial sector is the new frontier for bold capital. Natan is not just writing checks. He is navigating what it takes to succeed commercially in the ruggedized real-world with out-in-the-field operators across heavy industry.

Meet Natan

Q: You can be anywhere. Eating, drinking, and reading your favorite thing. Paint the scene.

A: I’ve been enjoying time on the water and in nature again. I am climbing Mount Kilimanjaro shortly, and that will be a big milestone for me personally. I’m also a huge history and architecture buff, so anything related to that is very interesting to me.

Key Quotes

“Industrial tech winners will be determined, not only on their speed of entry, but by how adept they are in their commercialization strategy.”

“Small Language Models excite our team. I am looking for sector-specific data for ruggedized equipment and factory floors where generalized models often fail.”

“Something that might look hot one day is also guaranteed to go through something tough at one point... remembering ‘this too shall pass’ is very helpful for getting through the ups and downs inherent to venture.”

“After years of leading research on industrial supply chain tech at CB Insights, I wanted a bigger stake and more of a hands-on approach, shy of being an operator myself, in the companies I was researching.”

“Is this someone I want to work with in the long run? When things invariably get tough, is this someone you want to be at the table with?”

Background and Personal Journey

Experiences Shaping My Investment Approach

My path into the industry was a mix of personal happenstance and the people I met along the way. Growing up in Palo Alto with parents in tech gave me a natural inclination toward the industry; however, my specific focus was shaped by an intersection of interests. While I was a generalist at CB Insights, my lifetime love of everything nautical led me to explore the link between blockchain and maritime supply chain back in 2017. Joining (and then helping to run) the New York Supply Chain Meetup community before the pandemic unlocked my passion for industrial tech. This eventually set my path toward an industrial focus and led me to Ironspring Ventures.

Moment Inspiring Venture Capital Career

The move to venture capital was less about the title and more about the depth of involvement. After years of leading research on industrial supply chain tech, I wanted a bigger stake and a more hands-on approach with the companies I was already researching across the industrial space.

Best Advice Received

I often rely on the advice that “this too shall pass.” I apply this to the volatility of venture capital; it provides helpful context for both the high and low points. Something might look hot one day, but it is guaranteed to go through something tough at one point. Remembering that the difficult times will also pass is very helpful for getting through the inherent ups and downs.

Philosophy and Insights

Values When Working with Founders

Integrity is my number one priority when working with founders. I always ask myself if this is someone I want to work with in the long run. When things invariably get tough, I want to know if this is the person I want to be at the table with. Additionally, I look for clear communication. I believe the ability to communicate well and provide consistent updates is highly correlated with a company’s success.

Approach to Risk

I view distribution and go-to-market strategies as two of the primary ways to de-risk an industrial investment. Industrial tech has extremely slow sales cycles; you cannot move at the same pace as other sectors. The major risk is whether a company can outlast the time it takes to break into the industry from a cash perspective. I also look to de-risk by ensuring there is industry DNA on the founding team to navigate specific personas, such as general contractors versus owners in the construction world, for example.

Measuring Success Beyond Returns

I measure success through three tiers of relationships. First, do the founders trust Ironspring enough to refer other founders to us? Second, have we stewarded the capital appropriately to maintain the trust of our LPs? Finally, I look at the ecosystem. I want Ironspring to be the ecosystem glue in the digital industrial space. Have we been able to foster that connectivity for folks even beyond our portfolio?

Trends and Future Vision

Exciting Trends and Technologies

Small Language Models excite our team. I am looking for sector-specific data for ruggedized equipment and factory floors where generalized models often fail. I am also very bullish on Mexico and the Latin American industrial market due to many macro tailwinds. There is a massive opportunity to apply established playbooks to white space in those markets. Finally, I am watching data silo integration. We need technology that actually connects disparate systems such as Warehouse Management, Transportation Management, and ERPs.

Misconception About VCs

A common misconception about the industry is that supply chain or industrial tech is no longer relevant following the collapse of a few high-profile companies. The underlying need for digitization in the physical world is unquestionably a necessity. The winners will be determined by how they are capitalized, execute, and approach go-to-market, not just because a category is deemed exciting or not.

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Connect with Monique

linkedin.com/in/moniquewoodard/

VC Uncovered’s View

Monique Woodard is an investor who sees the world through a wide-angle lens. While much of the industry is busy pattern-matching the past, Monique and her firm, Cake Ventures, are underwriting the future. She is a prime example of the independent, forward-thinking investors we celebrate at VC Uncovered, approaching venture capital with the technical precision of a researcher and the lived experience of a two-time founder.

The math behind her thesis is undeniable. We are currently witnessing a "three-layer cake" of massive demographic shifts: a global population aging at an unprecedented rate, a $30 trillion wealth transfer to women over the next decade, and a shift toward a much more diverse population, with Gen Alpha already leading that charge. Cake Ventures targets these shifts at the pre-seed and seed stages, focusing on the forward momentum of these groups rather than relying on what the internet user base looked like a decade ago.

Ultimately, Monique’s work is about measurably improving the global quality of life by investing in technology that meets human behavior where it is going. Whether she is backing "silver economy" solutions or tools for the deskless workforce, she is proving that the internet’s user base has outpaced the industry’s imagination. Her approach reminds us that the most significant value is created when we stop "artificial gating" and start building for the massive, universal markets of tomorrow.

Meet Monique

Q: You can be anywhere. Eating, drinking, and reading your favorite thing. Paint the Picture:

A: My happy place involves a mix of art, nature, and community. I find joy in looking at amazing pieces of art, specifically the work of artist Scherezade Garcia, and enjoy riding horses followed by sharing a glass of Pinot with my friends.

Key Quotes

“I believe that the future is really about this intersection of technology and demographic shifts, because demographic shifts reflect changes to the internet user base.”

“We’re investing where we’re going, not where we came from.”

“I wish there were more independent thought in a lot of the [VC] ecosystem. We’re all focused on AI in the same ways and trying to shove the same dollars into the same types of companies.”

“I track specific trends like the $30 trillion wealth transfer to women, the global aging population, and the increasing diversity of Gen Alpha. These are the forward-looking forces that create value.”

“I view an investment like a stack of layers, similar to a cake. Data and demographic trends inform the basis of my thinking. On top of that, I layer the team and their ability to execute.”

Original Responses (Lightly Edited for Clarity and Flow)

Background and Personal Journey

Experiences Shaping My Investment Approach

I have been in tech and startups for most of my career; I have been a founder twice and started a community of founders. My early career in investing at 500 Startups (now 500 Global) was where I began realizing I was investing in demographic change. I saw this clearly through early investments like Blavity, which is a media platform for Black millennials, and Silver Nest, which focuses on home sharing for the aging population.

The Path to Venture Capital

Moving into venture capital was a logical progression from my time as a founder and community builder. I love spending time with people working on their life’s work; I realized that building a new type of business in venture capital was the best way to stay close to builders while satisfying my own desire to create something new.

Worldview and Decision Making

I am heavily influenced by demographic shifts and the intersection of technology and human behavior. These shifts reflect the evolving internet user base. I track specific trends like the $30 trillion wealth transfer to women, the global aging population, and the increasing diversity of Gen Alpha. These are the forward-looking forces that create value.

Philosophy and Insights

Investment Philosophy

I focus on investing at the intersection of technology and demographic shifts to capture forward momentum. This approach grew from my observation that the internet user base is evolving rapidly. We have to look at what the forward momentum is rather than what we have seen in the past.

Unconventional Perspectives

I believe in investing in where we are going rather than where we came from. I avoid the practice of artificial gating, which is the idea of building a specific version of a product for a specific demographic (e.g., “Coinbase for Women” is just, well, Coinbase). Instead, I look for category-defining companies that use demographic shifts as a beachhead to build massive, universal markets.

Balancing Intuition and Data

I view an investment like a stack of layers, similar to a cake. Data and demographic trends inform the basis of my thinking. On top of that, I layer the team and their ability to execute. Finally, I use my gut to decide if I would go to war for a founder. Sometimes the best investments happen when you drop the thesis-driven portion and follow your intuition.

Working with Founders

I value the team piece heavily; I look for founders I feel I could go to war for. I view my role as building a partnership that satisfies my entrepreneurial itch by being hands-on with a portfolio. Success in venture capital involves having a big impact and finding other investors to walk alongside.

Specific Fund Mechanics and Targeted Sectors

I invest primarily at the pre-seed and seed stages. While I describe myself as a thesis-driven generalist because demographic shifts impact every category, I specifically focus on digital health and wellness, the future of work (particularly deskless or non-office work like healthcare and manufacturing), consumer tech/brands, and the evolving enterprise workforce.

Trends and Future Vision

Exciting Emerging Trends

I am excited about the silver economy and the aging of Gen X into retirement. I am also focused on the deskless workforce, including healthcare, infrastructure, and manufacturing. I want to see how we can put AI into the hands of these workers who make up the majority of the workforce. While developers have been the early beneficiaries of these tools, we must now expand that focus to include AI-driven innovation for these other critical industries.

Improving the Ecosystem

I wish there was more independent thought in the venture ecosystem. Everyone seems focused on AI in the same ways, shoving dollars into the same types of companies led by the same types of founders. We should be applying technology to diverse categories like the deskless workforce. I write white papers and research reports to share my thinking; I do this to find people who see these big opportunities.

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