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Larry Cheng

Larry Cheng

Sep 17, 2026

1:00
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.
1:08
Believe it or not, and this is true, most of my time and experience with my founders has been very positive.
1:15
The joy of this business for me has been working with founders who are trying to change the world.
1:19
And as an investor, I have a wide aperture, and I think you have to, for how founders want to do things.
1:25
Because if you want them all to fit into a box... then you're almost taking away what's special about them.
1:30
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.
1:37
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.
1:00
Larry, if you could share one piece of advice with a young new investor, what would you tell them?
1:04
Tough question in this day and age.
1:05
I do think a couple of thoughts.
1:07
I think it's ultimately important to do something that you enjoy and you find fun.
1:12
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.
1:20
It's really hard to win a competitive world.
1:23
The other people you're competing against
1:26
than you
0:59
Larry, what's the biggest mistake or the hardest lesson you've learned, and what's the story behind it?
1:04
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.
1:16
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.
1:27
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.
1:34
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.
1:39
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.
1:49
It sucks.
7:15
Now back to the interview.
7:16
On today's special segment, we have Larry Chang of Volition.
7:19
Larry, can
7:20
you tell us about an exceptional founder you've worked with and the specific thing they do that's unique?
7:25
Not to go back to Chewy, but Ryan Cohen, the co-founder and CEO there, his exceptionality is amazing.
7:31
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...
7:38
the amazing customer experience would be for his customer and really differentiate it.
7:43
Like really out there, he worked backwards.
2:01
Larry, can you tell us a story about a startup that you passed on, your anti-portfolio?
2:07
In my early days as a young investor, I went to Harvard.
2:10
I was at Battery Ventures at the time.
2:12
And I went back to visit a school club that I was involved with.
2:16
And I asked the students, what's going on on campus at school? And they said, there's this new website called Facebook.
2:22
And I said, oh, what is it? It's like a social network that had been started by Zuckerberg and Eduardo Saverin.
2:28
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.
3:49
Now back to the interview.
4:47
Larry, what is the best question you've been asked by an LP?
4:50
Believe it or not, I think the LPs should spend more time understanding the dynamics between the partners.
4:59
And sometimes, and I think we make this mistake as investors looking at companies as well, that is where the magic is made.
5:05
It's the intersection and interplay of the people.
5:08
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.
5:35
And it's kind of like us torturing the financial model of a business.
5:38
and ignoring whether the management team is working well together.
5:55
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.
27:28
Investor.
27:29
Oh, investor.
27:29
Okay, gosh.
27:29
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.
27:46
Like, that, that's the quality of a great investor.
27:49
Um, I mean, think-- if you think about it, to, to have a disproportionate outcome, you probably need two things to be true.
27:56
You probably need to have an original perspective, because if you don't, then it's a commodity perspective.

10 MINS LATER

37:35
... distill that down from your experience?
3:08
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.
3:15
Yeah, so let's go there.
3:16
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.
3:23
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.
3:33
And when we first started this firm in 2010, it was two years post-financial crisis.
3:39
No one wanted to invest in a new emerging firm.
3:41
They wanted to even cut their allocations to this asset class and only stick with the firms that they knew.

12 MINS LATER

16:11
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?

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