Demi Obayomi - Sapphire Ventures
"Success is the ability to make other people’s dreams come true."
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.
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