founding partner @gamechangersvc @iaventures. investor @AlpineF1Team @marlins @detroitwnba @motorcitygc. graduated @umich @columbia_biz. family man. wolverine.
Joined February 2008
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Missing Plaid remains one of the more painful parts of my venture career, a lesson underscored by a similar miss with Chainalysis. In both cases, I realized I made the same fundamental mistake.
I was focused on underwriting the specific idea itself, rather than simply trusting the great founders behind them. My error was not writing a check and allowing them to figure out the path.
At the earliest stages of investing, it is always about the people first. Truly exceptional individuals will adjust their missions to achieve the ultimate vision.
What's your biggest takeaway from this insight?
Founders shouldn't be too malleable; they need to absorb input without completely adopting your perspective. This distinction is crucial for building a resilient venture.
My role isn't to teach them about their industry. Instead, I guide them on effective communication with employees and how to strategically position their message.
The best founders already possess an encyclopedic understanding of their field, often teaching me new insights. Their unique, orthogonal viewpoint is invaluable.
What qualities do you value most in founders?
#newyork
I invested $2.2 million across four checks in The Trade Desk before it even had a product in the market.
What stood out to me was the combination of a massive market opportunity, an industry that was still in its early stages, and a founder who understood the space inside and out. Jeff Green had the knowledge, the experience, and the determination to build something better.
At the time, many VCs believed ad tech was already overfunded and the market didn’t need another demand-side platform. I saw it differently.
Sometimes, the best opportunities come from looking at a market everyone else has already dismissed and having the conviction to see what it could become.
What is different this time is the percentage of venture dollars going into a small number of companies by an even smaller number of venture firms. This concentration of capital is unprecedented.
So where does this leave the rest of the industry with a smaller quantum of dollars but a larger n of firms? Feeling squeezed at both ends. The cost of entry in the consensus companies is beyond reach while the access to capital to support non-consensus businesses is sharply constrained.
Only the strong, the visionary and those with unwavering conviction in the non consensus will survive this super cycle. Thousands of firms will be the walking dead, while a small set will survive and emerge from the ashes of the inevitable washout even stronger.
So which group are you in? Unless you know you’ve got what it takes to win and can sell this vision to LPs and founders alike, you’re toast.
Welcome to early stage non-consensus venture investing c.2026.
@gamechangersvc
Pricing in venture is wilder than ever.
$100M pre-seed is now normal.
Bessemer just raised $1.75BN for “early” and $4BN for growth.
So can you even do seed today without $1BN?
- Is capital truly one of the last remaining moats?
- Do all small seed funds and mid-sized firms just fade into irrelevance?
- Does entry price matter anymore when there are $TRN companies…
- Is this real or a bubble that is about to burst
I sat down with @spdholakia to discuss this and have added my notes from the discussion below.
1. This Is a Supercycle Like Never Before
Sameer has spent 31 years in software and has felt magic only a handful of times. A trillion-dollar supercycle followed every one of those moments, and he notes that it does not happen very often.
What is different and what is similar to prior cycles @altcap @infoarbitrage
2. Capital Is a Moat Today
Markets pick winners and the choice becomes a self-fulfilling prophecy, as it did when developers settled on SendGrid and Twilio. In legal AI, big law firms name just two major providers. Capital lets leaders scale at an extraordinary pace and build a brand, which draws talent and customers in a reinforcing flywheel.
Do you agree with this @venkyganesan @dafrankel
3. Who Wins and Who Loses in the Future of Venture Capital?
As industries professionalize, firms must be either a giant global platform that consolidates or an extreme specialist, such as an early-stage AI investor in San Francisco. Sameer counts Bessemer as a big global platform. Firms caught in between face a hard world to make money.
Is it go big or go home @rodriscoll @rabois @chetanp
4. The Rationale for Why Anthropic Would Compete With the Hyperscalers and Why We Invested
As in the cloud era, AI would be massively capital intensive, so it would consolidate to a handful of players with hundreds of apps on top. Microsoft had partnered with OpenAI and Google was building Gemini, while AWS had an undistinctive internal model and had just invested heavily in Anthropic.
5. Why Price Does Not Matter in a World of AI and the Metric That Truly Determines Value
Bessemer invested in Abridge at $5M of ARR for a $700M to $800M valuation, in Anthropic at roughly 150 times current ARR, and led Legora's $1.8B round at $20M of ARR. Sameer judges these deals on what the company can become in the next twelve months.
How has your relationship to price changed in a world of AI @mignano @mmurph
6. Why the Rise of Open Models Does Not Denigrate the Market for Closed Models
In a market this large, predicting the mix between closed and open tokens with any precision is irrelevant. Consumers, enterprises and governments will all want different flavors of intelligence. Bessemer has invested in both Anthropic and Fireworks to hold exposure to closed and open tokens.
Love to hear how you think about this @lqiao @bernhardsson
7. Why It Is a Permanent Structural Shift That Companies Will Stay Private for Longer, but Why It Will Open in 2028
With more dollars and more firms in private venture, companies will stay private longer, and most of the run-up in this boom will happen in private markets. Sameer still expects an unlock in IPOs later next year and in 2028.
Love to hear your thoughts on this @bgurley and how you see it evolving in 24 months?
(links in comments)
There’s nothing more exciting to me than helping founders realize what they’re capable of.
At the earliest stages, you get to help someone find their lane, build confidence in their vision, and finally say, “I’m all in on this.” That kind of transformation is incredibly fulfilling.
I’ve worked at the highest levels of Wall Street and run billion-dollar trading businesses, but nothing compares to helping one or two people build something great.
And from an investment perspective, early-stage investing has tremendous leverage. One exceptional outcome can make up for many investments that don’t work out. That combination of purpose and potential is why I’m focused on early-stage founders.
#newyork
For me, the biggest milestone wasn’t getting rich when The Trade Desk went public.
It was proving that our investment thesis was right.
That first major success validated what we believed about ourselves: that we could pick great companies, identify promising sectors, and build strong partnerships with founders.
It gave us the confidence to move beyond wondering if we were good at what we did and start thinking more strategically about what came next.
Once you’ve proven your approach works, you earn the freedom to ask a better question: What’s the smartest way to manage liquidity for the long term?
#newyork
The best founders I know have a clear vision, but they’re also willing to listen.
That doesn’t mean they take every piece of advice they receive. It means they’re open enough to consider different perspectives and use them to make better decisions.
I think there’s a big difference between having strong convictions and believing you already have all the answers.
Founders need to be intentional about who they let into their inner circle. There are plenty of people willing to offer advice, but only a few who genuinely make you think better.
At the end of the day, the founder makes the final call. The right people around them should help sharpen their thinking, not replace it.
I see time horizon and risk tolerance as two of the biggest advantages an investor can have.
But here's something I've learned about myself: I wasn't born with a high tolerance for risk. Both of my parents were very risk-averse, and over time, I deliberately pushed my own comfort zone.
In investing, volatility can create opportunities for those who have the conviction and staying power to endure it. But you have to be willing to sit through the uncertainty long enough for your thesis to play out.
For me, that's a learned skill. And developing it has fundamentally shaped the way I invest.
One thing I look for in great founders is a strong sense of product aesthetics.
And I don't just mean how something looks. I mean understanding where the product ends and the customer experience begins.
Whether you're building an API for engineers or an app for everyday consumers, you need to understand the person on the other side of that product.
What do they need? What frustrates them? How can you make their experience better?
To me, that kind of empathy is a critical part of building something people genuinely love to use.
Key words: sick shit 😂.
We’re so excited to deepen our partnership with the @AnvaraHQ team!
Bringing programmatic plumbing to sponsorship.
They said it couldn’t be done in advertising: wrong. They say it can’t be done in sponsorship. Wrong again.
LFG team! @gamechangersvc
We just raised another $2.5M @AnvaraHQ, bringing us to nearly $7M raised.
We’re building the marketplace for sports and live event sponsorships, helping brands like @Kalshi and @micro1_ai do sick shit IRL.
@gamechangersvc @infoarbitrage
People often see venture capital as a glamorous career, but if you're doing it right, it's an incredibly demanding job.
You're not just investing money. You're investing in people, their dreams, and the future they're trying to build. Especially in the early stages, founders are navigating uncertainty, difficult decisions, and the fear of failure.
I've had founders call me in the middle of the night from halfway around the world, and I wanted them to know they could reach out when things got hard.
To me, being a good investor means showing up when it matters. But it also means learning how to set boundaries, because the line between work and life can get very blurry.
At the end of the day, venture capital is as much about people as it is about capital.
The founder <> investor relationship is a partnership when it's done right, especially when it starts early in a company's life. Times are rough, sleeves are rolled up and trust is developed.
It stands to reason that as a company achieves success and it's financing rounds become "hot" that the issue of pro rata rights can become contentious. This is but one of several points in a company's life where founder<> investor alignment can be strained.
I believe a lot of the talk about this issue has been pretty binary, as much of the discourse in society today. Black and white with no nuance. This is, however, a very nuanced issue regardless of the legalities, especially in the context of a trust relationship.
What is not OK is for founders to accept out of hand that earlier investors should capitulate to demands of later stage investors, or for early investor to be insensitive to the pressure put on founders by later stage investors. There can be collaboration, joint problem solving and ethical treatment between trusted parties. When one of these elements breaks down, you get the kinds of conflicts you've read about for the past week.
I will profess that one of the reasons I've enjoyed building my firms outside of SV is because of the crazy ass shit and zero sum mind-set of many inside the echo chamber. It has been this way during every supercycle during my 20+ years in the business.
Bottom line, there isn't one right answer. There is one right condition for handling an admittedly challenging and stressful situation: founder <> investor trust and respect. End of story.
@gamechangersvc #vc #prorata
One of the most important lessons in investing is understanding your time horizon.
David Swensen built Yale’s endowment around the idea that when you’re investing for the long term, you can take a very different approach. He committed significant capital to alternative investments when many people thought it was unconventional.
What made that strategy work was the ability to stay invested over long periods and let the portfolio compound.
I think that’s a critical advantage. If you have the right capital base and the patience to match it, you can invest in opportunities that shorter-term investors simply can’t.
Your time horizon can be one of your greatest advantages as an investor.
I think one of the biggest advantages a smaller investment firm has is the ability to go where everyone else isn't looking.
We've seen this cycle play out before with cloud computing, machine learning, and now AI. When a theme gets hot, large funds pour in because they need those massive wins to justify the amount of capital they're deploying.
But that also creates opportunities elsewhere.
If I were investing in pure tech today, I'd spend far less time chasing the hottest AI opportunities and more time looking for overlooked markets with enormous potential.
You don't have to compete for every deal. Sometimes, the best opportunity is in the market everyone else is ignoring.
In 2021, I went through a period that changed a lot for me. During COVID, I lost both of my parents in a relatively short span of time, and honestly, I lost the passion I had for my work.
When I built IA Ventures, I made a promise to myself: if I wasn't going to be all-in, I was going to step aside.
I'd seen what happens when leaders hold on to ownership long after they've stopped doing the work, preventing the next generation from stepping up. I never wanted that for my firm.
So when the time came, I did what I'd promised myself I'd do. I handed the keys to my partners and gave them the opportunity to carry the firm forward.
For me, leadership isn't just about building something. It's also about knowing when it's time to let go.
A very well-written and insightful post from @kwharrison13.
I clearly have deep respect for Benchmark and USV (where I’ve been an LP for almost 20 years), but at @gamechangersvc we’re still taking the road less traveled (similar to the path we took and my partners are still taking at IA Ventures).
I am confident that the gap Kyle described is real and will persist for a generation, and that it is small, dedicated early stage practitioners that will capture the value overlooked and uninteresting to most of the capital in the industry.
But it will require funds with enough capital to carry companies until their progress is legible to a subset of downstream providers of capital.
One thing I’ve learned in venture capital is that backing a great founder isn’t enough. You also need to be looking at the right market.
An exceptional founder in a limited market may still have a ceiling on what they can build.
And even a massive market can go to waste if the founder can’t attract exceptional people and build a great team.
For me, it comes down to both: A-level founders and A-level market opportunities.
When you get that combination right, the potential outcome changes dramatically.
One question my partners and I talked about for years was: How do you identify exceptional founders early?
I don’t think the answer is always found in what they’re building.
Sometimes it’s something completely unrelated. Maybe they built a guitar, became an incredible musician, started a business, or simply pursued something they cared deeply about and became exceptional at it.
What I’m looking for is evidence of a mindset: If I set my mind to something, I can become exceptional at it.
The problem they’re solving may change. The market may change. But that drive, grit, and willingness to put in the work can be incredibly difficult to teach.
One of the qualities I look for in great founders is what I’d call a non-negotiable vision with highly negotiable missions.
The best founders I know have incredible clarity about the company they want to build and the impact they want to have.
But they’re not dogmatic about how they get there.
Markets change. Customers give you feedback. Sometimes the path you thought would work simply doesn’t.
The founders who stand out are the ones who stay unwavering about the destination while being flexible enough to change the route.
That balance of conviction and adaptability is incredibly powerful.