Episode summary
Why the Best VC Investments Look Wrong Early
How I Invest With David Weisburd
· · 47 min · Hosts: David Weisburd · Guests: Maya Bakhai
Summary
Maya Bakhai argues that the best venture outcomes usually look wrong at first because they are built before a category becomes obvious. Her path into VC came through 35 Ventures with Kevin Durant and Rich Kleiman, where she saw how a celebrity-backed platform could create access, but also how easy it is to mistake access for insight. That experience taught her to build conviction instead of copying tier-one consensus.
She says early-stage investing is a game of taste, while late-stage investing is more about sales and access. In her view, too many investors chase narrative premiums, reacting to whatever is hot in a given quarter instead of asking whether a business is real, capital-efficient, and rooted in demand. She points to examples like Crocs, Hugging Face, medical tourism payments, and Girl Beer to show how companies can look eccentric or premature before culture and usage catch up.
Bakhai also emphasizes that founders and investors need unconditional conviction. The founders she backs keep building when the market is indifferent, while the best investors keep reassessing their thesis without becoming slaves to the latest blog post or meme. Her core advice is simple: trust your own gut, avoid overreliance on others’ opinions, and look for boring, hard opportunities where real edge can compound.
Key takeaways
- Maya Bakhai says early-stage venture is mostly a taste game, while late-stage venture is more about access and sales.
- She argues that tier-one signaling can trap investors into following consensus instead of doing independent work.
- Bakhai says narrative premiums and discounts distort pricing, creating opportunities when a category is ignored or suddenly fashionable.
- Her Crocs and Beehive stories are examples of cultural arbitrage: being early to behaviors that later become obvious.
- She believes the strongest founders build unconditionally, even when they cannot yet get perfect financing or validation.
Notable quotes
“the less you try, the the easier it becomes”
How the episode opens
So my you've invested into 72 companies at Spice Capital. You're on your third fund, but before then you started in 2017 with Kevin Durant on a startup investments. Tell me that story.
It was pretty non-traditional of a backstory or entry into investing. I had this crazy opportunity to work for 35 Ventures which was started by Kevin Durant and his agent Rich Kimman. Rich had the like kind of fortitude and I would say the guts to, you know, when Kevin was working for the Warriors, um, to start making relationships with some of these tech founders and it was a really interesting moment in time where side was like the best networking you could you could ever go to.
There were like billionaire CEOs, tech CEOs,
Boritz, Yuri Milner.
Yes. Exactly. And there it was almost like you could run up and down the court and be doing deals.
And I think credit to really Kevin and Kevin's agent, they were opportunistic. They took advantage of that. So they were saying yes to meetings.
They were like attending all the things. They were speaking at conferences. Like Kevin and Rich were at Techrunch Disrupt and really putting themselves out there as like open for business in a way that most athletes had not done in from an investment perspective.
Mo most of them had done it from an endorsement. And so I got hired to help manage this, you know, deal flow and be almost like a chief of staff. Um, and that's how I weasled my way into venture capital.
And just to take a step back, — You make it sound easy, but tell me the story about how you actually got hired. — I grew up in South Florida. I really wanted to leave Florida and move to New York.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- venture capital taste
- narrative premium
- tier one signaling
- cultural arbitrage
- creator economy investing
Companies and tickers mentioned
- CROX
- Spice Capital
- 35 Ventures
- Crocs
Watch the episode
Watch “Why the Best VC Investments Look Wrong Early” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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How I Invest With David Weisburd, this episode and its artwork belong to David Weisburd. Octagon is not affiliated with the show; this page is an independent summary.
