
Larry Cheng
8
APPEARANCES
2
PODCASTS
012
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Sep 17, 2026
Investor Stories 493: Founder CEO Removal, Acquisition Pressure, and Co-Founder Conflict — Lessons from Investors at Volition, Notable, and Fika (Cheng, Solomon, Chen)
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Nick MoranHOST
Larry, without revealing specifics, talk about one of the highest stakes conflicts you've faced as a VC, why the issue occurred, and how it was resolved.

Larry ChengGUEST
Believe it or not, and this is true, most of my time and experience with my founders has been very positive.

Larry ChengGUEST
The joy of this business for me has been working with founders who are trying to change the world.

Larry ChengGUEST
And as an investor, I have a wide aperture, and I think you have to, for how founders want to do things.

Larry ChengGUEST
Because if you want them all to fit into a box... then you're almost taking away what's special about them.

Larry ChengGUEST
But still, maybe my box is wider, but there have, you know, obviously a type of conflict is if the founder is not working out.

Larry ChengGUEST
And I remember when I was younger, actually, and I was a board member with a partner on a company and we had to replace the founder CEO at the time.
Investor Stories 490: Investors from Volition, Acadian Ventures, and Interplay Ventures on Building Competence, Operating Experience, and Investing with Purpose (Cheng, Black, Peter Davis)
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Nick MoranHOST
Larry, if you could share one piece of advice with a young new investor, what would you tell them?

Larry ChengGUEST
I think it's ultimately important to do something that you enjoy and you find fun.

Larry ChengGUEST
And I know that sounds a little bit trite, but maybe the reasoning is not, which is when you're in school, you may not realize how competitive the world really is.
Investor Stories 488: Losing Conviction, Overpaying for Discounts, and Selling Too Early — Lessons from Volition, Acadian, and Interplay (Cheng, Black, Peter Davis)
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Nick MoranHOST
Larry, what's the biggest mistake or the hardest lesson you've learned, and what's the story behind it?

Larry ChengGUEST
When you look at the history of investments, when you completely lose money on an investment, which I've done, the hardest thing about that experience isn't that I've lost money on an investment or Volition has lost money on investment, although that is hard.

Larry ChengGUEST
I, I guess what's hard about that is anytime an investor like myself or even a VC loses money, that means the founder, the management team, all of the employees have probably lost as well.

Larry ChengGUEST
And, and I don't know if that's totally internalized when people and founders look at their companies, uh, look at, look at prospective investors.

Larry ChengGUEST
Like, when there's a sixty or seventy percent loss rate, that means everyone who worked in those companies, they lost, every one of them.

Larry ChengGUEST
And so I think seeing that early in my career, seeing that a couple times, uh, here, um, it just makes me hate the idea of losing, not for me, but for everyone involved.
Investor Stories 486: The Traits of Visionary Founders: Ecosystem-Scale Thinking, Data-Driven Truth-Seeking, and Relentless Customer Experience Design (Blank, Demaree, Cheng)
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Nick MoranHOST
you tell us about an exceptional founder you've worked with and the specific thing they do that's unique?

Larry ChengGUEST
Not to go back to Chewy, but Ryan Cohen, the co-founder and CEO there, his exceptionality is amazing.

Larry ChengGUEST
And I think what he did at Chewy that others don't do is probably driven by his paranoia, was that he had in his mind what...

Larry ChengGUEST
the amazing customer experience would be for his customer and really differentiate it.
Investor Stories 485: Inside VC Anti-Portfolios: Missing Whatnot, Facebook & MongoDB (Dillon, Cheng, Black)
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Nick MoranHOST
Larry, can you tell us a story about a startup that you passed on, your anti-portfolio?

Larry ChengGUEST
And I asked the students, what's going on on campus at school? And they said, there's this new website called Facebook.

Larry ChengGUEST
And I said, oh, what is it? It's like a social network that had been started by Zuckerberg and Eduardo Saverin.

Larry ChengGUEST
And so I spent some time with Mark and Eduardo, and I actually brought them back to my firm that I was working at and explained to them what a term sheet was and socialized the term sheet and so forth.
Investor Stories 483: Best LP Questions from David Ulevich, Eric Ries, and Larry Cheng: Mission, Partnership Culture, and Enduring Institutions (Ulevitch, Ries, Cheng)
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Larry ChengGUEST
Believe it or not, I think the LPs should spend more time understanding the dynamics between the partners.

Larry ChengGUEST
And sometimes, and I think we make this mistake as investors looking at companies as well, that is where the magic is made.

Larry ChengGUEST
And so sometimes I think the best LP is really ask softer questions like, what did you and your partner argue about most recently? What's something that your partner thinks that you think is totally wrong? Like what are those types of things? And what have what's been something that you guys have disagreed on for the last 15 years that you haven't totally figured out? Like those types of questions that get into the relational dynamics rather than sort of torturing the return spread issue, which I mean, you have to do.

Nick MoranHOST
How does a partnership group coexist when they're in, let's say, significant opposition over some issues in tech and investing? but also, you know, appreciate each other, like each other and are willing to let, you know, their partners do some investments that they just think are fundamentally bad ideas.
512. Is SpaceX Over or Undervalued, Why Consensus Kills, How Chewy Beat Amazon, and the GameStop Saga from a Board Member (Larry Cheng)
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Larry ChengGUEST
You know, [sighs] the-- I've, I've thought about this and, um, and I think Peter Thiel said something along these lines, which I very much agree with, which is the capacity, uh, to look stupid [chuckles] for a long period of time until hopefully you're right.

Larry ChengGUEST
Um, I mean, think-- if you think about it, to, to have a disproportionate outcome, you probably need two things to be true.

Larry ChengGUEST
You probably need to have an original perspective, because if you don't, then it's a commodity perspective.
10 MINS LATER
200 Rejections to a Billion-Dollar Exit: Larry Cheng on Resilience and Growth
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Ryan HanleyHOST
Um, and just interesting where that came from and kinda how that applies to both the businesses you run and the, the businesses inside your portfolio.
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3:16Larry ChengGUEST
When we re- when we started Volition Capital, we're a private equity firm, uh, specifically focused on growth, and we had to raise a, a fund.
L
3:23Larry ChengGUEST
And, uh, a, a fund is made up of different investors, very institutional, like university endowments, big charitable foundations, wealthy family offices, and so forth.
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3:33Larry ChengGUEST
And when we first started this firm in 2010, it was two years post-financial crisis.
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3:41Larry ChengGUEST
They wanted to even cut their allocations to this asset class and only stick with the firms that they knew.
12 MINS LATER
Ryan HanleyHOST
So like how do they start to think through or, or is there maybe a, a framework that you would recommend for figuring out which type of partner is the best for you and, and what you want to achieve with your business?
