Connect with Anthony

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

VC Uncovered's View

Meet Anthony

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

My favorite place in the world is probably Japan. I love going to Tokyo. I've spent a couple of weeks there in November and been there three times now. There's something peaceful and exciting about Japan. The people are amazing, the food is incredible, and the culture is different than out West. When you travel in Western countries, a lot of stuff feels similar, but everything is completely new in Japan. You're looking around, constantly amazed. It's easy to saddle up at an izakaya, meet people, have a beer, and walk around. It's the best place to travel.

I have enough nonfiction in my life, so I read science fiction and fantasy novels as an escape. I just finished the Stormlight Archives by Brandon Sanderson, which is quite exhaustive, and I'm reading a couple of his other things because the guy spits out words.

Meet Bukie

Original Responses (Lightly Edited for Clarity and Flow)

Background and Personal Journey

Experiences Shaping My Investment Approach

Two experiences shaped my approach to investing. The first was starting in tech recruiting at Riviera Partners. I was lucky because there were only eight people when I started. In the first month, the firm worked on VP of Engineering and CTO searches for Twitter, Zynga, LinkedIn. This was in 2010 when things were just starting to take off.

Over the next few years, I worked on numerous early-stage venture-backed startups in stealth mode, essentially building engineering teams of 5 to 10 or 10 to 20 people. These companies became Cloudera, Sumo Logic, Zendesk, Yammer, Groupon, and AngelList—now household names. At such an early stage, I saw the difference between good and great and understood how founders approached building their companies.

We were introduced to these companies and founders through investors, so I saw how human capital and venture capital came together to build amazing companies. This experience was incredibly influential.

Then I spent eight years in-house, first at AppDirect, growing to 600 people and a few hundred million dollar run rate, and then at Stripe, growing from 200 to about 2,000 people. When I started doing M&A work at Stripe, I saw many cool companies coming across my desk, cutting-edge things with impressive teams. I realized I was missing out on all this early-stage innovation.

So, I wanted to be part of that again, and coincidentally, Dan Portillo reached out about joining Sweat Equity Ventures as part of the founding team. Dan, our co-founder and now GP, has had an incredible impact on how we think about investing—as a talent and network business at the end of the day.

Unconventional Belief

Seeing a lot of change in a short time builds a type of rigor and endurance that folks who have never operated before don't have. It's like running a race without ever having pushed your pace. That's why we tend to invest more in seasoned entrepreneurs than young ones, particularly those who have undergone multiple step changes over a very condensed period.

It changes their ability to execute. That's the difference between being talented and being experienced and great. More often than not, I look for experienced and great versus just purely talented and knowing what market you will target.

I want to see folks who went from handfuls to thousands of people in a few years, built systems to scale, especially in complex environments that require immense rigor and detail orientation. I look for that experience in founders.

You Worked for Stripe, a Very Successful Company. How has that helped you?

I don't know if I could count how many ways working at Stripe has helped me. The rigor, to start. We obsessed over every sentence we wrote, every person we hired, and certainly every decision we made.

We consistently over-hired for roles, bringing in former founders and executives for mid-to-senior positions. I can't tell you how many conversations I had with people leading 40, 50, or 100-person teams, asking them to come take a 4 or 5-person upstart team.

It created the right kind of pressure to produce a great product and maintain a high-performance, rigorous culture. It was ambitious and honestly quite competitive—I think everybody there thought they should be two or three levels higher than they were. It was collaborative but competitive, like sports where everyone wants to be a starter.

Beyond that, I learned about building systems and teams to scale. Stripe is now one of the largest companies in the world. Publicly, it will process over a trillion dollars in payments this year—a number most people can't even conceptualize. And it's highly regulated—you can't mess up these payments because real businesses depend on them. If your payment system is down for an hour, that's a meaningful dollar impact. You can't lose that trust.

Philosophy and Insights

Values When Working with Founders

I don't have too many strict principles, but I need to see a couple of things. One is that founders have to be world-class storytellers. This produces three key benefits: they can fundraise, sell, and recruit. If you can do those three things, you're steps ahead.

The other thing is being ruthlessly commercial. We meet a lot of really technical founders, and we tend to invest in engineers or very technical product people. But they must also be great storytellers who can articulate their vision and know where they're going—something that comes with earned expertise.

I want founders who know their customer, who they're selling to, and the value proposition. They should be constantly networking and trying to sell their product and vision. When we look at our most successful portfolio companies, these are the two factors that stand out.

Approach to Risk

I think investing revolves around three things: can you get access, do you have good taste, and can you win? When you start, your access is probably less good than it is now, your taste is probably less developed, and your ability to win deals is perhaps less. This can create a more conservative strategy or adverse selection when you first start investing.

You might default to the very generic pattern: star founder who went to a great school, worked at Stripe or OpenAI, building something in fintech or AI. That's an obvious choice.

But maybe the real risk now is not trying to hit the ball on the fairway but trying to jump the trees a little bit—looking outside the obvious patterns. For us, it would be a mistake not to take more risks by going after founders who want to tackle very large markets with entrenched incumbents. We want to support founders who can solve pain at the edge of large markets, where it’s most severe.

Trends and Future Vision

Exciting Trends and Technologies

As soon as I mention a trend, it will change in a week or two so I try to avoid focusing too much on them. There are many interesting problems to be solved and potential new ecosystems to be built that could become meaningful companies, but are they venture-scale companies?

Recently, we've certainly seen a lot of vertical AI applications—taking traditionally offline businesses like professional services, legal, and finance, and trying to increase their margins from 25% to 40% or 50%. I think that's interesting, meaningful, and probably good for the economy but venture-scale, not sure yet…

One strong theme for me is that I believe developers need better tools to do their jobs so we should continue to invest in them as a core audience. The other is that more transactions will continue to move online, therefore fintech will keep growing across all layers: payments, anti-fraud / AML, new payment methods, wallets, rails, and stablecoins.

We're only at about 20% digital payment penetration globally (of $100T), so many decades of growth are ahead in a $20 trillion market.

More services will be delivered and consumed via APIs, which is why we invested in Stainless—developers need better SDKs to deploy these solutions.

The big question is how much time developers spend in IDEs versus writing in human language. This new trend of vibe coding (humans + AI) – is that the future?

I see many orders of magnitude more code being written over the next decade, whether by humans or AI, which means we'll need better tools to manage it all. This is a big reason why we invested in Graphite.dev.

We tend to look at where value accrues over time. More code, great transaction volume, more services deployed via API – this means more emphasis on data and infra.

Challenges for Early-Stage Founders

One obvious challenge is whether OpenAI or Anthropic will just build the solution themselves. The stuff they shipped recently, with reasoning capabilities, probably destroyed a bunch of startups. And we’ve seen it happen before.

User acquisition costs continue to climb. We're in a deflationary period for software development, which means it's much cheaper to build and launch faster. It's not perfect, but with the right team, you can get more done with fewer talented builders.

This means more companies are starting, creating more competition and making user acquisition more difficult. We're also seeing fewer job openings for junior and mid-level engineers. Does that force them into entrepreneurship? I hope so, but I don't know yet.

In this period, when writing software is becoming less expensive and less human-capital intensive, can larger companies be more nimble than before? Does that reduce the startup advantage? How do you think about customer acquisition, and how do you do it effectively? Does that mean you must build a better brand or be more creative? These things should keep most founders and their investors up at night.

Is There Anything Else You’re Working on You’re Particularly Proud About?

I run the Stripe investment syndicate. Our alumni group is pretty big now—about 2,500 people in Slack, and our investment syndicate has around 600 members. At this point, we probably make three to five investments per year.

We've gotten this thing to an effective place that is strong for the community, educational, and fun for people. I'm now talking to other companies at a similar or one stage earlier about whether they want to do something similar. And I’m always looking for more people who want to start one at their company.

I want to give other companies a framework, show them how to do it, and help them understand the value of spending five to ten hours a month on it. It's been valuable for me—we've made investments and kept me in the deal flow.