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The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified

6 Jul 2026 · 42m · 18 chapters

Episode artwork

512. Is SpaceX Over or Undervalued, Why Consensus Kills, How Chewy Beat Amazon, and the GameStop Saga from a Board Member (Larry Cheng)

In short

Larry Cheng (Volition Capital) discusses specialty e-commerce vs Amazon, how investors handle negative signals during diligence, whether software is “dead” in the AI era, AI’s impact on jobs and enterprise adoption, and capital allocation at GameStop. He also evaluates SpaceX’s public valuation as a venture-style bet and explains how consensus decision-making can kill good deals.

Guest backgrounds

Larry Cheng is co-founder and managing partner of Volition Capital (growth equity; investing from a ~$675M fund). Previously led investments at Fidelity Ventures and started at Bessemer. First investor in Chewy; has invested in U.S. Mobile, Rounds, and Global Trans.

Key claims

Chewy won by tailoring merchandising/pricing/fulfillment/customer experience to pet owners—Amazon couldn’t replicate the specialty focus. Great investments can have flaws; the key is “exceptionality,” not flawlessness. Software isn’t dead, but agentic replication raises risk; entrenched vendors benefit from customer AI spend. Job losses are likely but timing is uncertain due to metered adoption and possible displacement by AI-native firms. SpaceX is worth far more than traditional metrics, but still needs time to realize value.

Notable examples

Chewy vs Amazon; Pets.com as a “perceived risk” that later proved manageable; GameStop’s ~$56B bid for eBay and its shift to profitability/Bitcoin treasury; SpaceX’s Starlink and compute/data-center growth; Fable/agentic model rollout and regulatory/security concerns; Uber’s early negative gross margins; Akamai as a controversial-to-success VC deal.

Written by AI. May contain mistakes.

Chapters

1:04

Investing in Chewy: Insights and Risks

Larry discusses the investment rationale behind Chewy and the risks involved.

“So I'd love to start off and talk about some public companies.”
2:38

Overcoming Investment Challenges

Exploration of psychological barriers in investing and how to maintain confidence.

“that I'm investing in this company and Amazon's advertising for their own pet food store?”
4:31

E-commerce vs. SaaS in Today's Market

Discussion of the viability of e-commerce specialty players in the current market.

“in this AI-driven era we find ourselves in?”
7:01

GameStop's Transformation and Board Strategy

Larry explains GameStop's financial evolution and strategic board decisions.

“So I'd probably put those two in different categories as well.”
9:37

Evaluating SpaceX's Market Value

Insights into the valuation of SpaceX and its business segments.

“And so I think it was, it's a Charlie Munger who said that like great investors, they have opposite attributes paired together, which is you are both incredibly patient and incredibly decisive at the same time.”
12:00

The Future of Software amidst AI Trends

Discussion on the current state of software in the context of emerging AI technologies.

“What part of SpaceX's business do you think will drive the most value in the future?”
14:00

AI's Impact on Job Markets and Business Dynamics

Explore the dual nature of AI in job markets and company strategies.

“higher new bookings, those types of things in this era.”
18:40

Cultural Dynamics in AI Adoption

Understanding the cultural shifts required for effective AI integration.

“And we know, even from the companies that we work with, that there is a range.”
23:00

Investment Strategies in the AI Super Cycle

Discussing emerging investment themes amidst the AI transformation.

“What theses or themes, you know, really jump out as areas that you think are going to enjoy, you know, growth in the coming five to 10 years?”
28:00

Originality and Contrarian Thinking in Investing

Learn the importance of being original and contrarian in investment decisions.

“So you need to see something others don't see.”
Show all 18 chapters
29:16

Risk Perception and Market Dynamics

Understand how perceived risks can impact investment opportunities.

“If someone said 20 years ago that a primary mode of transportation will be you getting into the vehicle driven by a stranger, that would have been original and contrarian.”
31:19

Decision-Making Models in Investment Committees

Explore the effectiveness of different decision-making models in investment teams.

“but you have to weigh them appropriately.”
33:05

Perceived Risks vs. Actual Risks in Investments

Learn the difference between perceived risks and actual risks in investments.

“I wouldn't even necessarily advise majority decision-making.”
34:16

Innovative Thinking in Growth Equity

Discover how innovative thinking can lead to successful investments in growth equity.

“Like high margins, high recurrence, very diversified customer base, tons of upsell, great value.”
35:59

Board Structure and Management Insights

Gain insights on effective board structure and management for startups.

“The only thing that means to me is that we have missed something in due diligence because there is these are all young companies and they all have to have to be some flaws around it.”
37:50

Advice for Founders on Board Management

Learn valuable advice for founders on how to manage their boards effectively.

“And so, you know, in the private company role, you want to stay under like even five becomes the larger size, but seven is large.”
40:06

The Power of Consistency as a Superpower

Understand how consistency can be a key factor in achieving success.

“You know, the Dale Carnegie book, How to Win Friends and Influence People, is a classic.”
41:27

Connecting with Larry Cheng and Volition Capital

Learn how to connect with Larry Cheng and follow Volition Capital.

“And so, so I think consistency is, is the superpower that I hope to have.”
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Transcript

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0:00This episode is brought to you by Ramp, the spend management platform we use here at TFR. They're offering listeners$150 just to take a demo. We've never had an offer quite like this. Claim your$150 before this offer is gone at our partner link, ramp.com slash partners slash TFR. Now on to the episode. Welcome to the podcast about venture capital, where investors and founders alike can learn how VCs make decisions and reach conviction. Your host is Nick Moran, and this is The Full Ratchet. Larry Chang joins us today from Boston. He's the co-founder and managing partner of Volition Capital, a growth equity firm currently investing out of a$675 million fund.

0:48Before Volition, Larry led investments at Fidelity Ventures and began his venture career at Bessemer. He was the first investor in Chewy and has invested in companies including U.S. Mobile, Rounds, and Global Trans. Larry, welcome to the show. Great to be here, Nick. So I'd love to start off and talk about some public companies. Let's do it. You know, we've got some interesting public news on the forefront, so we'll put a pin in that for a second. But you were the first investor in Chewy. Correct. And, you know, what I'm curious about is, you know, what made you believe that they could build a standalone e-commerce winner in the pet category when so many categories, you know, had been or would be sort of slips in by Amazon and eBay?

1:35You know, Amazon is the everything store. And what I saw in the pet market was a large segment that was moving online, but the customer wasn't going to be taken care of well in a superstore and an everything store. And what Chewy had done was focus their experience and their merchandising, their pricing, their fulfillment, everything around wowing the pet food customer, which is something that Amazon couldn't do. So it was the classic sort of specialty, super tailored experience against the generic experience. And the pet category in and of itself is it's an emotional category. People really care about their pets and the humanization of pets was expanding.

2:12So we thought Chewy had a great chance to win in the category. their customer retention was like phenomenal, like Amazon Prime level retention. And we saw the math and the business was working. So we thought they had a shot. And I'd be lying though if I said I wasn't worried because when I was in due diligence on the company, I was getting Amazon boxes that were advertising their pet food store called Wag at the time. And I thought, am I freaking insane that I'm investing in this company and Amazon's advertising for their own pet food store? Like, but it worked out well. So how do you overcome those hiccups, right?

2:49Late in a deal, you've written about this a bit, but there's like a psychology thing going on here, right? If like the financial situation, personal financial situation is difficult. Yes. If the markets get rocked and drop substantially, if you get bad news about a portfolio company, if colleagues start talking about the downsides of an investment, there's all these factors that can creep up late in a diligence process. How do you kind of, you know, use sort of selective memory or, you know, compartmentalize these things and still push forward, you know, with confidence? You know, every good investment, there should be someone saying something negative.

3:30There should be an alternative perspective. And so I think I'm used to that at this point is that you're not looking to hit the finish line of investment and hope everyone around you is cheering you saying, this is fantastic. Please do this investment. That is not the case. That's usually a recipe for just saying you've missed something in due diligence. And so the question is, for any great investment, and this took me years to learn, there are going to be very, very good reasons to pass at the time of the investment. Because you could have passed on any number of companies. Think about the one that was in public, SpaceX.

4:01Like, there are probably a thousand reasons to pass on that at every round. And so you have to become accustomed to that and understand, like, what is the true exceptionality of this business? is that exceptionality in my head or is that real and demonstrated in some way? And will that carry them through some of the risks that might be in any business? And so it's sort of having that true north mentality around exceptionalities are what carries a great investment, not the absence of flaws. Love it. Do you think an e-commerce specialty player like a Chewy can be built in this AI-driven era we find ourselves in?

4:41I don't think Chewy could be built right now, to be honest. We invested in Chewy in 2013, and it's a public company today, but we held that business for five years before we sold it. And we kind of snuck up on Amazon. I remember seeing market research reports saying that the percentage of online spending in pet food was a certain amount, and that amount was less than the revenues of Chewy. And so we snuck up on the entire market. We snuck up on the big box retailers and we built a differentiated offering. I think it'd be hard to do that today. That being said, if I were to counter that, we invested a ton in customer service and there's still our verticals where I think the leading players could do a better job in service.

5:29And that's what Shuey did was just exceptional service. And I think those opportunities can still exist, But we might not be as under the radar today if we tried it again. It feels like on the surface, there's a lot of nuance to this, but it feels like on the surface, e-commerce and marketplaces are more durable than pure SaaS in this environment. Depends. I think that's general. It's kind of funny because two years ago, you would never have said that. and I do think there are certain categories of software that should not be brushed with the software as dead stroke and SaaSpocalypse and all of that that are deeply entrenched into their tech stacks of their customers.

6:12They're deeply entrenched in the data mode and the data elements of their customers and their customers might not be your Silicon Valley startup that's on the bleeding edge and they will have the first right of refusal, if you will, on the AI spend of their customers And if they can't win it, you know, that's their fault. Shame on them. There are other software companies that are lighter workflow that I think are more easily displaceable in an area of agentic coding. And those I'd be more concerned about. But there's a mix, I would say. E-commerce is a hard business. I'm not going to lie. It's not easy to build Chewy.

6:48So I wouldn't say if you launch an e-commerce store and you're somehow immune, you still have to fight Amazon. You have to fight all the retailers. It's not an easy business. Marketplaces, if you can get to scale, can have more moats in e-commerce businesses. So I'd probably put those two in different categories as well. Got it. So another public company that I'd like to chat about is GameStop. You happen to sit on the board. Most people listening remember GameStop from the meme stock days. But a lot has happened since. The company's built up billions of cash. They started buying Bitcoin for its treasury.

7:21And then this spring made a real surprise move, roughly$56 billion bid to buy eBay, a company several times the market cap of GameStop. eBay's board turned it down. You were part of the board that put that offer forward. What did you all see in that combination that made it worth pursuing? Well, I'll make general comments if that's okay on this topic. I think Ryan Cohen, the founder, not the founder, but the CEO of the business and chair is the best spokesman for GameStop's plans. And we have a significant balance sheet today and we want to do some transformative actions with that balance sheet.

8:04The GameStop business is now quite profitable. It's a very strong business, particularly compared to when we first started getting involved with the business and when Ryan first invested in the business. And so it's a completely different ballgame today. And so you're seeing a very strong foundational business with a very strong balance sheet that's open to transformative ideas. And obviously, this is one of them. You know, something that strikes me is GameStop has become pretty multifaceted, right? It's still a retailer, but it's also one of the larger corporate holders of Bitcoin. It's now, you know, considering acquisitions.

8:43How does one think about the best use of, you know, balance sheet or the next dollar when it comes to, you know, a business like this and the trade-offs involved? I mean, it all comes down to one of the fundamental tenants or roles of a leader, especially a CEO, is capital allocation. And the question is always like, where can you optimize return on every dollar that you have to spend, whether that's, you know, issuing a dividend, investing in your own business, you know, Google invested in SpaceX and, you know, those types of things. There's different ways to optimize a balance sheet. And I think that's what we're doing is basically thinking open-mindedly about capital allocation and everything's on the table.

9:28I will say as a board and as a leadership team, we're patient and we are now looking to do things that are incremental. And so I think it was, it's a Charlie Munger who said that like great investors, they have opposite attributes paired together, which is you are both incredibly patient and incredibly decisive at the same time. And hopefully we can embody that. And were you on the board during that sort of historic run up and situation? Thankfully, I came on, I joined the board right after that. I see. So I was watching that from a bit of a distance. But that was quite a wild ride when I think GameStop was breaking internet brokerages everywhere and the markets were not working.

10:18So wild. So wild. But now you can come from a position of strength and potentially do a lot more. So the other company I wanted to touch on here, Larry, is SpaceX. They just went public. Are they worth$1.75 trillion? I didn't even look today. It's over two, right? Is it? Is it over two now? I mean, it closed over two on Friday. But not by any traditional measure is it worth$2 trillion right now. You're in Google and Amazon territory overnight with that type of market cap. And notwithstanding the potential in the business, I think Bill Ackman actually framed it sort of well in my mind, which is that SpaceX is kind of like a venture bet right now.

11:05You know, you have probably the most mature business is the Starlink business, and they're looking to have a sort of a global communications platform in the celestial sphere. And then a very high growth business is their compute and data center business, which they've signed recent deals with Anthropic and Google that are massive in size. Ironically, the space travel satellite rocket business is like that's the emerging business and all of it feeds on itself. But when you add it all together, there's a long way to go and there's risk in all of them to sort of warrant the current market cap. That being said, it's Elon Musk.

11:43And if he hits on them in a meaningful way, you know, there's some folks who think it would be undervalued at this level. But that would take, you know, a while to come. So I would never bet against Elon Musk, but there's a lot more that needs to come to make it all worth it. I see. I see. What part of SpaceX's business do you think will drive the most value in the future? You mentioned a couple of them. Some are nascent. I mean, the near-term cash flow driver will be obviously their Starlink business, but I don't know that that's the long-term value creator. When it comes to moving compute into space, moving, I mean, Elon even talks about harnessing the power of the sun to have lower-cost energy.

12:30if supply chains can move into space and they are the corridor to make that happen. Like this is before we're even talking about colonizing Mars. Like those could be massive, but they're much more speculative in nature. And so Starlink is the early meat on the bones on this one. Got it. So AI, infra, deep tech, space, all amongst kind of the hottest categories at the moment. Is software dead? Oh, no. Software is not dead. I will say this. When Opus launched and the software is dead, nomenclature emerged. It happened quickly. The markets corrected. And everyone kind of jumped on that notion. And then the market sort of improved a little bit for software in the last six weeks or so.

13:23And then now people are saying software is not dead. And I think it's too easy to jump on either side of that bandwagon. There is real risk and there's real opportunity for software. The good news about software, for software companies today is if you're sitting in that position where you're entrenched, there's going to be a substantial amount of AI demand and spend coming from your customers. And you're sitting there as an established vendor that's already tied into the ecosystem of that company. Like that's going to drive growth. So it's not surprising to me at all that you're seeing some existing software companies actually have higher, you know, new revenue, higher new bookings, those types of things in this era.

14:03But there's also this thing coming up the back, which is anything you build can be replicated and it's getting easier. And even with the Mythos launch that happened last week that lasted for like 48 hours. Yeah. Fable 5, like that was even a step function improvement in terms of agentic engineering. And so I think both are happening. The opportunity is bigger for those software companies that are entrenched, but the risks are coming as well. And you got to see both sides of that coin. Why do you think they pulled Fable so quickly? Do you think it was the security breaches? Do you think it was generalized AI fear and too many voices, you know, in the government's ears about that?

14:41Like, what do you think were the core reasons? My guess is it was related to security concerns. And I mean, I'm reading what you're reading. So that's above my pay grade. But there's an interesting question about regulatory dynamics around LLMs and so forth that this is raising, but my guess is that would have to be the precipitator. Were you surprised that it was Amazon? You know, I can't say when it first came out that I think, oh yeah, that must be Amazon. I did not think that. But in some respects, that's not entirely surprising either. Why do you think? Just because there's a battle royal happening amongst different players, and, oh gosh, there's new acronyms emerging that replaced the FANG acronym of the players in AI, but some of them are not suitable for work.

15:32But Amazon, Anthropic, and others being in the mix of that, they're all going to be pressure testing each other along the way and I suspect that this won't be the last time. Should we anticipate significant job losses with the development of AI? The battle royal on this topic as well. I think probably the initial reaction was, and this was anthropic-led in many respects and others, that there's going to be massive job losses in the very near term. That's proving out to be somewhat overstated right now. Then you have this whole other side, which is saying, hey, in every single innovation cycle, we thought we were going to lose jobs, and we didn't.

16:14So this is going to be another one of those. And I think that's a little bit overstated as well. I think what's mitigating job reductions for a lot of companies is their adoption of AI is actually quite metered. Not every company is a Silicon Valley startup with no compliance and no rules and no heritage in their tech stack, nothing. And what you're seeing out there is very metered, methodical, slow adoption. And one of two things will happen. Either those companies will eventually figure out the right AI tech stack for their business. and there better be some reduction in jobs because you're going to have an increase in token spend.

16:51Or those companies will be obviated by other companies that were more AI native out of the gates and can move faster and produce more quickly. And so I actually think there will be pretty meaningful job losses, but the timing will be interesting. Probably given the way the world works, when everyone has declared there will not be AI job losses, see, because all of all this data, that's probably when it will happen because at that point in time, the stack will have been built. Interesting. Yeah, how do you think about, you've talked a couple times now about large entrenched players and their ecosystems and how they can leverage AI to their advantage and users are pretty sticky.

17:36How do you think about sort of innovators dilemma in this context? Pricing models are changing. You know, we're moving from seat-based to, you know, usage-based or tokens or outcome, you know, in some cases if it's a services model. And Benny Off has talked about this a bit. You know, he's trying to migrate Salesforce from seat-based to more of a metered plan. But with it comes risk, right, because you're cannibalizing a lot of your own business. Not to mention the cost side, you know, eats into your margins because you've got computes. So, you know, how do you think about sort of the large entrenched players and their benefits, but also, you know, some of the things working against them from a cash cow and cannibalization standpoint?

18:26It's one of the things that I'm really trying to assess, particularly now, any company that we're investing in, which is softer, which is what is the culture inside this company as it relates to AI? Everyone in my world is going to come in and have a pitch deck that says something about AI. But what's for real? And we know, even from the companies that we work with, that there is a range. There are some people that are like, burn the boats. We have to go here. We have to reinvent. And there's no stone unturned in this journey. And we're going to do it right now. That is one segment. And then there's another segment at the other end, which is like AI is basically slideware and nothing has changed inside.

19:10And there's everything in between. And boy, like I do think there are some larger, particularly tech companies that are more into this, into the first range. The Silicon Valley startup companies are existing and have been living in that range. But there's a lot of companies that are sitting in a culturally sort of paralyzed space. and it's very hard to move on from how you know how to do, how you've been doing things as a company, as a person and so forth. And if that reinvention does not happen, you might not feel it right now, but you as a company or you as a person will lose your relevance and value in the economy that is coming because the capacity of what you can do with AI is accelerating, which means the delta in value with someone who knows how to use it versus you is going to expand.

20:05And that's on a personal level and a corporate level. Before we move on from sort of the jobs question, what do you think about young folks, though, coming out of university? How do you think this impacts them? Because I just know from personal experience, like, you know, I'm spending all weekend using agents to automate a bunch of the workflows at the firm that typically an analyst would help me with. um yeah so i i actually think the the young people might be in a better spot than the older people in some respects um i mean they're we are seeing uh kids who are coming out that are truly ai native like they their their whole educational path especially in the coming years we'll we'll have an ai rapper in the middle of all of it and um and you know what it's there is this there is this element that's underappreciated when it comes to adopting AI, which I think the emerging set wrestles with less, which is how to think creatively about what can be done.

21:05Sometimes there is this limitation in our own minds, which is we can't even conceive of it. So we don't try it and we don't try it and we don't, it doesn't factor into our systemic view of what can be done and not exclusive to young people. So just to be clear, but that creativity can exist more in people who've grown up natively with it. But I will say this, what also matters really importantly in AI utility is context. And what younger folks don't have is context. They don't have the seasoning, the experience, the knowledge. And so if you can marry someone who has like the burn the boat, AI all in native mentality with a ton of context and experience and wisdom, like that is a great marriage.

21:48And, you know, you like hold onto that with all you got. Yeah, I was thinking, you know, as I'm doing terminal and clog code work this weekend, I'm thinking, you know, in another world, I might have wanted a young person that's more savvy with these tools. Like if I hadn't been a developer myself. Yeah. And I'm not writing a bunch of code, but, you know, it's in the terminal. It's a little different, right? And I would think, you know, I bet in another context, had I never been a developer, I would just want a human co-pilot alongside me where I could give them the requirements and they could kind of run all these cycles themselves.

22:24It's kind of funny. They often say, like, use AI so you can up-level to a higher-level role and have AI do kind of your mundane work. I am at a higher-level role. So ironically, what I feel myself doing is like the last two weekends, I'm actually doing like engineering work, product management work, product design, QA of like the stuff that I'm building. And I just I think it's comical that I'm I'm doing all this stuff on various things that I'm building and and because it's so easy and it's so fast. And so I think it may work in both directions. That's so funny. So, you know, as you think about Volition's thesis, you know, where you're going in the future, not just like a sector or stage or check size, but what other axes of investment are interesting to you, whether in the AI context or not?

23:23What theses or themes, you know, really jump out as areas that you think are going to enjoy, you know, growth in the coming five to 10 years? I mean, what's interesting is we're at the early innings of another super cycle. And it's so much fun at the beginning because if you think about the transition to dot-com, cloud, mobile, and so now we have AI, which might be dwarf all of them. The early innings are where you have very big market opportunities. Let's be clear, like this is bigger right now than the 20th year of the SaaS cycle, right? At the end of the cycle, you're like battling over smaller markets.

24:04But it's almost like the world is your oyster. If you look at every single industry and you say, like, they're all going to be transformed by AI. If you look at every single horizontal function in the enterprise, those will be transformed by AI. If you look at every single consumer service and experience, those will be reinvented with AI. And you can almost think about every hardware category and think about, for many of them, there will be an AI layer on top of that. And so what you're looking at is it's all about durability and market opportunity. And I almost asked simpler questions today, which is, will this be an important company in five or 10 years?

24:43And will it be a durable business to get there? And because everything is in the state of being transformed, and that's what makes so much value creation possible when these types of cycles happen.

25:16$150 just to take a demo. No need to sign up. Head to ramp.com slash partners slash TFR to claim your$150 before the offer expires. Now back to the interview. So Larry, you've written about these two different investor mindsets. The first that prioritizes the absence of flaws, the second that prioritizes the presence of exceptionality. I think if you're an investor, you're always trying to do the second, but you may be disqualifying certain opportunities because of the first. So my question for you is, my first question is, what flaws do you feel like are acceptable that many might consider disqualifying?

26:04This is a terrible answer. I, almost every flaw could be acceptable in the right situation. Perhaps the one unacceptable flaw is a lack of integrity in the founder. But from a business perspective, listen, you know, if you wanted to invest in Uber in the early days, you would have had to accept negative gross margins. Okay. Usually that is bad. Negative gross margins might be a flaw that would scare 90 % of investors. Yep. Well, that would have cut off something like that. I mean, Chewy's gross margins when we invested were 9%. That was almost unacceptable to the world of growth equity when you can invest in 90 % gross margin software businesses.

26:43We've had businesses where, you know, the flaw might have been that there were lots of failures in this business model in the past, and therefore the capital markets are scared of it. Like, that's an acceptable flaw. There are flaws like geographic risk and so forth. But in business model, you're uncomfortable. That could be another flaw. But those flaws can all be managed, not in a compounding way. You don't want all of these together. But if there's something truly exceptional on the flip side, absent founder integrity. I see. I see. What do you think are some of the standout qualities of a great investor?

27:23Sorry, standout qualities of a great founder, investor? Investor, not founder. Oh, yeah. Oh, investor. Okay, gosh, you know, I've thought about this, and I think Peter Thiel said something along these lines, which I very much agree with, which is the capacity to look stupid for a long period of time until hopefully you're right. That's the quality of a great investor. I mean, if you think about it, to have a disproportionate outcome, you probably need two things to be true. you probably need to have an original perspective because if you don't, then it's a commodity perspective. So you need to see something others don't see.

28:04And by original, that literally means like no one else in the room has your perspective, which is hard to do, or no one else in your market or your asset class. And the other quality is to pair with originality is you need to be willing to be contrarian. Meaning if you told everyone in the room your original perspective, not only would they not have it, they would think it's stupid. And that is the reaction. And then you need to be able to persist in that space until your thesis plays out to be correct. And the reality is most people are not wired that way. And if you're not wired that way as an investor, then what you're going to end up to is investing in things that are unoriginal, that are non-contrarian, and that is not how you generate disproportionate returns.

28:47And the reality is if you are original and contrarian, a couple of things could happen. One is you could be completely wrong, and everyone who thought you were stupid is correct. And that makes it hard to come back and be original and contrarian again. Or you could be right, and not to overemphasize something like SpaceX, but if Elon Musk sat in a room of investors 20 years ago and said, listen, I want to colonize Mars, that would have been original and contrarian. If someone said 20 years ago that a primary mode of transportation will be you getting into the vehicle driven by a stranger, that would have been original and contrarian.

29:28Or sleeping in their home. Or sleeping in their home. And so you need to be able to sit in that space where the world doubts you, if not even mocks you, and persist through it. That's what a good investor can do. And, you know, that also implies like you are going to suffer some zeros and maybe a number of them along the way. Like how does one keep the contrarian original confidence, you know, as companies are failing left and right? And you're saying, well, that's that's the intent, you know, like you should have some companies going to zero. The loss ratio should exist. You know, in my world of growth equity, which is different than venture, we hate to lose money.

30:10I hate to lose money. You know, venture capital loses money about 70 % of the time. In my world of growth equity, it's probably about 20, 25 % of the time. And so it's not to say that you're contrarian, therefore you throw out all risks. But there are risks that I think are more perceived than actual. Well, as an example, I mentioned if you, investors are often scared of companies that have failed predecessor business models. Like in Chewy's case, it was, what was the sock puppet company? Pets.com. Oh yeah, Pets.com. Yeah, so Pets.com was the biggest failure in the dot-com bust. And they had that sock puppet ad and everyone was like, when we reconciled dot-com bust, that was the pinnacle of stupidity.

30:59Well, it's 13 years later when we invested in Chewy. And so that would still feel contrarian because you're staring at the failure. But is it really like the world has changed? There are a lot more internet users, et cetera, et cetera. And so sometimes the hardest risks to get over are actually perceived ones, not like actual fundamental flaws in the business model. So it's not like in our mentality that we throw risks out the door, but you have to weigh them appropriately. It's tricky, right? Because I think the deal we made, we've done 55 some odd deals, but the deal we made that I took the most heat for from my peers was a defense tech deal in 2018.

31:38And everyone's just like, this is not venture. And now it's become like the hottest company in the portfolio, you know, that's scaling the fastest and et cetera. And so sometimes these cycles just have to come around and you kind of have to, you know, deal with the heat until it does. You know, in all of our, we've all worked at different firms, the partners here, and pretty much without fail, when we look back at our very, the very best investments of our predecessor firms, and you go back to the decision making at the time of that investment, those were the most controversial deals that turned out to be the best.

32:16And, you know, in my early days in the business, when I was at Battery Ventures, Akamai Technologies became the biggest venture-backed hit of that era. And that's located here in Cambridge. It's a content delivery network. And that was a deal that three or four partners passed on internally at Battery. And, like, the fourth or fifth one actually did the deal. And these types of stories abound. And what you realize is your investment decision-making process, it absolutely has to account for dissension in the investment team decision-making. Otherwise, you're going to regress to the mean, or people won't say what they really think.

32:52So you have to manage the cultural dynamics about that. I mean, does that suggest that democratic decision-making on investment committees is not something you would advise? I wouldn't advise unanimous decision-making. I wouldn't even necessarily advise majority decision-making. There's sort of the champions model and the consensus model. And there's been a lot of studying about this. And what consensus-driven decision-making does in investment committees, first of all, it actually doesn't open up conversation. It limits it. Like people don't want to block your deal because you might block their deal type of thing.

33:27And so it becomes very political. And what the champions business decision-making model does is, yes, there are risks. And yes, your investment committee will point them out. But the champion may see the exceptionality in taking account of the risks. But the exceptionality might ultimately carry the day. But again, if you're in this majority decision-making model or unanimous, then you could just focus on all the risks till the cows come home. And you may miss on some of the best ones. And that's what we have seen in some of the both MIT and HBS research on the topic. What risks do you love leaning into and which ones do you not like taking?

34:09I like what I call perceived risks. I love, and we talked about this earlier, but listen, I would love for a business model that's perfect. Like high margins, high recurrence, very diversified customer base, tons of upsell, great value. I love all of that. But you may not get all of that. But where I feel like I have a bit of a DNA advantage is just when there's a perceived risk that everyone thinks like that's not possible or that's stupid or that's failed before or that's an uninteresting sector or that's not the type of customer we'd want. That's where I feel comfortable. Like a good business, a good fundamental business with some perceived flaw around it is a beautiful thing in my mind.

34:57What would you say is your competitive advantage at Volition? Um, it is, it is sitting in this area of willing to do deals that others might not. The growth equity industry as a whole is pretty homogeneous in its thinking. It's why the industry has centered around software for so long. Most growth equity firms, a majority of them are pure play software and with good reason, which is the software business model is phenomenal and has been phenomenal. You have high recurrence. You're paid up front. You have super high margins. You're mission critical. That's a beautiful thing.

35:35But I've leaned more towards transactional internet businesses, more mass market, more consumer. And in that space, you have to think a little bit differently. And sitting in the discomfort of thinking differently than others, sitting in the discomfort of not having consensus, sitting in that area of perhaps even people thinking this deal is stupid or whatever. Like that's my comfort zone. Where I get quite honestly nervous is when everyone loves it. The only thing that means to me is that we have missed something in due diligence because there is these are all young companies and they all have to have to be some flaws around it.

36:13So does that suggest you're doing investments in atoms as well as bits, as they say? Tell me more what you mean by that. Well, I mean, like hard businesses, physical AI, robotics, you know, not just AI software. We do. We have a mix of hardware and software. But what's interesting is I've spent most of my time in sort of scalable internet business models where no one thought the website was the barrier to entry. So the idea that you would have a barrier to entry that is not in the technology platform itself is kind of a world that I've lived in. So we're used to network effects being a barrier to entry.

36:57We're used to data modes being a barrier, distribution partners, brand, community, et cetera. Those can all be barriers, and they have been for some of the Internet businesses we've invested in. And now those are elements that you'd want to see in a software business as well. And so I think it's almost like the worlds are merging in some respects. Maybe a few wrap-up questions here. Larry, you've sat on a number of boards, both public and private. If you were giving advice to a founder on structuring the board, effectively managing a board, how would you distill that down from your experience?

37:39Oh, that's a great question. I think you want to have a range of opinions, a range of expertise in a narrow box. So I think boards become less effective the bigger they get. And so, you know, in the private company role, you want to stay under like even five becomes the larger size, but seven is large. In the public company world, it can expand well beyond that. And then it just, it becomes a bureaucracy, not an actual governing, active governing body. And so, and I think you want a range of perspective within that. And, but probably most importantly is that body needs to be able to speak truth into the leadership of the team.

38:26And they, it can't just be, it can't be a passive sort of rubber stamp type of body. that you need to be able to have people who will tell you as the CEO, I disagree with you. I think this is your blind spot. And good CEOs should actually do the inverse, which is ask the question of the board, like, what am I missing? Where are my blind spots? And so you want that in your board. And then perhaps most importantly is you want your board to be owners and operate as owners. Like there's a lot of boards that are set up these days where they're just not aligned with their shareholders. And they never purchased the stock of the company that they're on the board of.

39:11They're granted stock, but they don't purchase it. On all the boards that I'm involved with in the private world, like we've invested in the company. That's the only reason I'm on the board is because we are owners. But you get into other areas where the board are not owners of the business in the truest sense. And that's a misalignment in my view as well. Larry, if we could feature anyone here on the show, who do you think we should interview and what would you like to hear them speak about? You know, it almost goes back to who would you want to have lunch with? And I'm sorry if this is a commodity answer, but I would love to hear from Warren Buffett or Elon Musk.

39:48That crew would be certainly quite interesting in the world of business and investments. They're truly exceptional talents at what they do. So if lunch with either of those goes up for option on eBay, let me know. Larry, give me in the audience one book, article, or video that you would recommend. Oh, boy. One book, article, or video. You know, the Dale Carnegie book, How to Win Friends and Influence People, is a classic. And I always pay attention to classics that still are on the bestseller list, you know, 50 years after they were written. and that book is about, it's well-titled, I guess, because it's self-explanatory, but there are some classic principles in that that I still apply today and it's not a hard read, so I recommend that book.

40:44Larry, do you have any habits or behaviors that are a secret weapon? Maybe it's the meta habit or the meta layer, which is, I think the superpower that is above all other superpowers is consistency. And it's very hard to maximize any superpower if you're not consistent with it. So over time, I've sort of appreciated the compounding benefit of doing even something small consistently right. Like if you even read 10 minutes a day or 15 minutes a day, like that will compound over time. If you eat healthier in a slightly different way and you do that consistently, that will compound over time. And so, but if you're inconsistent, it kind of doesn't matter how talented you are.

41:30It's, that's going to get in your way. And so, so I think consistency is, is the superpower that I hope to have. And I think is, is the enabler of everything else. And then finally here, Larry, what's the best way for listeners to connect with you and follow along with Volition? Oh, I'm on X at Larry VC. And then I'm also on LinkedIn at just my name, Larry Chang, C-H-E-N-G. And obviously the Volition website's VolitionCapital.com. All right. He is Larry Chang and the firm is Volition Capital. Larry, thanks so much for the time today. This was great. Thanks so much, Nick. Take care.

42:11All right. That'll wrap up today's interview. you. If you enjoyed the episode or a previous one, let the guests know about it. Share your thoughts on social or shoot them an email. Let them know what particularly resonated with you. I can't tell you how much I appreciate that some of the smartest folks in venture are willing to take the time and share their insights with us. If you feel the same, a compliment goes a long way. Okay, that's a wrap for today. Until next time, remember to over-prepare, choose carefully, and invest confidently. Thanks so much for listening.

From the publisher

Larry Cheng of Volition Capital joins Nick to discuss Is SpaceX Over or Undervalued, Why Consensus Kills, How Chewy Beat Amazon, and the GameStop Saga from a Board Member. In this episode we cover:

  • E-commerce and AI-Driven Era
  • GameStop's Transformative Moves
  • SpaceX's Market Cap and Future Value
  • AI and Software Industry
  • Impact of AI on Jobs and Companies
  • Volition Capital's Investment Thesis
  • Investor Mindset and Risk Management
  • Board Management and Advice for Founders

Guest Links:

The host of The Full Ratchet is Nick Moran of New Stack Ventures, a venture capital firm committed to investing in founders outside of the Bay Area.

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