20VC: Is Seed Investing Dead Without a $1BN Fund? | Does Ownership and Price Matter When Companies Can Be $1TRN Exits | Are AI Revenue Numbers Real and What to Watch Out For with Venky Ganesan, Menlo Ventures
Venky Ganesan’s answer to an overheated AI market is to keep playing, but change position size rather than pretend anyone can time the turn. Firms that exited dot-com investing in 1996–97 missed 1997–99 and returned in 2000; today, each seed check is “an option to see if it’s an outlier,” with concentration added only after revenue and quantifiable evidence arrive. “A dot is not a line.”
Seed still exists, but core AI “neo-labs” and $10–20 million application rounds make traditional small-fund construction brutally difficult. Menlo uses some seed checks to buy a seat at the table and is therefore “somewhat indifferent” to the initial valuation, expecting the real capital deployment to come after winners reveal themselves. For $30–100 million funds that need $1–3 million allocations, the high-stack poker table is a punishing place—though exceptional managers can still win.
AI revenue must be underwritten as a business reality, not accepted as a fundraising artifact. Harry flags contracted “annual” revenue that is neither live nor annual and run rates extrapolated from the best day of sales; Venky’s rule is that “if any metric is measured by an investor and they put a lot of weight on it, it’s gonna be gamed.” The decisive distinction is whether founders optimize for terminal value or the next markup.
Price and ownership matter, but neither can be judged without outcome size, evidence and access. Venky would rather own 2% of a trillion-dollar company than 20% of a $100 million company; Menlo owns less than 2% of Anthropic yet has laddered its investment until Anthropic reached 20% of one Menlo fund. Once an outlier is obvious, “there’s no alpha there”—the game becomes access and position sizing—so early ownership remains valuable.
Outcome inflation cannot excuse weak portfolio mathematics because time and dilution compound against the investor. Menlo models a seed position falling from 10% to roughly 3.5–4% by exit, or about 60% dilution; slow companies also damage IRR and require more financing and option-pool expansion. Because AI companies pay economic “taxes” to Nvidia, hyperscalers and foundation models, Venky says private venture must beat the accessible “Mag Seven” by roughly 1,000 basis points to justify fees, carry and illiquidity.
Strategic-acquisition “downside protection” is dangerous because buyers have no obligation to protect the cap table. Venky compares today’s confidence with dot-com acquisitions of pre-product companies and asks why a strategic acquirer would honor the cap table when it might hire the founders directly. At 30–50x, he favors selling perhaps 10–15% to lock in gains and enable a longer hold, but Menlo generally will not sell its entire position while remaining aligned with the founder.
AI’s capital intensity can justify faster deployment, but it does not repeal vintage risk. Menlo Eight invested across roughly ten months in 2000–01 and remains the firm’s only fund that has not returned capital; its $1.5 billion Menlo Nine and $1.2 billion Menlo Ten also underperformed expectations and drove LP departures. LPs now want DPI, yet many also need AI exposure as a hedge against software-heavy private-equity portfolios threatened by AI.
The durable edge Venky claims is institutional humility: remove ego, allocate capital well and keep running. He will accept a smaller allocation or a higher-priced tranche if it can make money for LPs—“the rest of this is all noise”—and tells LPs to evaluate the windshield by interviewing founders, not merely study five-to-seven-year-lagging performance. His closing principle: “There’s no limit to what a person can do as long as they don’t care who gets the credit.”
1. You have to dance, but every seed check is only an option
Harry’s provocation is that venture no longer resembles venture when teams report that “we can’t find anything under $100 million”—not the valuation, but the round size. Venky concedes that core AI labs may seek billions and that the moment is “very disorienting, confusing,” but cautions: “A dot is not a line.”
The market-timing lesson comes from firms that made money early in the dot-com boom, stepped away in 1996–97, missed 1997–99, then re-entered in 2000. LPs had hired them to remain at the cutting edge. Venky’s conclusion: play the game, but vary selectivity, portfolio composition and position size.
His portfolio model treats every seed investment as “an option bet.” A fund needs enough at-bats to encounter an outlier, then should size up only when revenue and other quantifiable evidence support the designation. Concentrating before the evidence arrives is a materially different risk from laddering into a demonstrated winner.
Seed is particularly hard in AI “neo-labs,” while even application companies increasingly raise $10–20 million rather than the old $3–5 million. Large platforms worsen the distortion: Menlo is sometimes “buying ourselves a seat at the table,” relatively indifferent to seed valuation because its actual objective is the right to invest heavily later.
2. Metrics become theater when investors reward the theater
Harry’s pushback—worth keeping—is that the evidence itself has become murky: contracted annual revenue may not be live or annual, while a revenue run rate may multiply the company’s best day by 365. Venky agrees with the mechanism: any metric investors heavily reward “is gonna be gamed.”
The SaaS-era specimen is net revenue retention. A single $100 purchase order shows 100% retention; start with a $10 order and add $50 a week later, and the displayed expansion becomes 500%. Beyond metric selection, Venky invokes “the bezzle”—while unsure who coined it—to warn that booms also conceal creative accounting.
King-making is Soros-style reflexivity: genuine growth earns a markup; the markup brings capital, publicity and talent; those inputs accelerate growth. Copycats then mistake the markup for the cause, and investors assume one markup guarantees another. “All reflexivity will eventually stop”; leverage and a major debt default, rather than equity losses alone, may expose the break.
Tranche financing began with sound differentiation: raise lower-priced “build-with-me money” from investors who add value, then higher-priced capital from passive investors. But cycles move from “the innovators” to “the imitators” and eventually “the idiots”; once every company copies the structure regardless of quality, it becomes another fundraising technique.
3. Price is often a proxy for opportunity—and ego is an expensive filter
Paying up can mean merely paying whatever wins the deal, but it can also mean seeing a much larger total opportunity than competing investors. Venture’s asymmetry changes the calculus: invested dollars can go to zero, while a winner can return 10x or more. Consequently, “the most expensive mistakes venture capitalists make are the deals they passed.”
Venky’s haunting omission came while he served on Plaxo’s board. After Sean Parker left, Parker urged him to meet a Boston college dropout; Venky distrusted the situation and declined even the meeting, forfeiting the chance to write perhaps a $50,000 check. Parker’s tell was uncommon insight into virality, network effects and human behavior, communicated simply.
On later, higher-priced tranches, Venky refuses to be insulted because another investor—Harry’s example is Peter Fenton—entered more cheaply. He admits ego has previously affected valuation negotiations, syndicates and allocations that felt too small: “My one lead ego is to make money for my investors. If I can make money for my investors, who the hell cares?”
Founder diligence starts with the premise that “the company you build is the team you build.” Venky asks why these people chose each other from billions of alternatives, then asks how their five closest friends would describe them in three words. References test whether that answer reflects self-awareness; known weaknesses are manageable, while blind ones are dangerous.
4. Ownership matters most before the outlier becomes obvious
Venky rejects treating ownership as an isolated target: “I’d rather take 2% of a trillion-dollar company than 20% of a $100 million company.” Menlo owns less than 2% of Anthropic, demonstrating that low percentage ownership can still produce consequential exposure when the denominator is extraordinary.
Before an outlier is known, ownership preserves return potential as well as information. Menlo’s Higgsfield example paired a $5 million check with 15% ownership and then an opportunity to size up. Once everybody recognizes the winner, selection alpha has disappeared: access and position size replace discovery.
Menlo has taken Anthropic to 20% of one fund, but Venky stresses the sequence. The relevant question is not whether 20% entered in the first check; it is whether the firm laddered toward 20% as new evidence strengthened conviction. With even 10% company ownership increasingly difficult, that staged concentration becomes the route to fund-level impact.
Harry questions whether falling ownership is justified by a broad expansion of outcomes or merely a handful of enormous companies. Venky’s answer is portfolio insurance: the target remains a home run, but ownership lets a triple matter when the grand slam never arrives. Otherwise the portfolio offers only “grand slam home runs or strikeouts.”
5. Time, dilution and public-market opportunity cost dominate venture math
Menlo assumes that 10% ownership at seed may become only 3.5–4% at exit—roughly 60% dilution from subsequent financings and option-pool expansion. As a working rule, Venky suggests expecting an initial stake to be approximately halved by the end.
Time is the hidden variable. A company that compounds valuation quickly can exit sooner, raise with less dilution and deliver higher IRR: “That’s a double win.” A long holding period inflicts two costs at once—IRR deteriorates while repeated financings and hiring grants consume ownership.
Velocity also changes employee-equity economics. A $200 million company might grant a senior executive 2%, a meaningful transfer of ownership; at $2 billion, it can offer the same $20 million of value through roughly 0.1%. Fast appreciation therefore protects existing investors from both financing and human-capital dilution.
Venky’s answer to “DPI or IRR?” is both, but today IRR requires explicit attention. AI companies pay a “tax” to Nvidia, a hyperscaler and potentially a foundation model—assets investors can increasingly access through public markets without venture fees or carry. Private funds therefore need about 1,000 basis points of excess IRR to justify their structure.
6. Downside protection can disappear before the company does
Venky learned liquidity through Avanex: a $5,000 IPO purchase grew to roughly $200,000, but he rejected his fiancée’s suggestion to fund a house deposit and eventually sold after a 90% fall for about $8,000–$9,000. Harry counters that selling Salesforce early would have destroyed Emergence’s defining return; Venky’s resolution is balance-sheet context, not a universal sell rule.
Today’s casual assumption that a strategic buyer will rescue a company at $1.5 billion resembles dot-com claims that success meant a multibillion-dollar sale and failure meant acquisition for the talent stack. Venky cites Nortel’s $3.5 billion purchase of Kairos and Lucent’s $4.5 billion Chromatis purchase as the prior-cycle pattern; it stopped working after March 2000.
More M&A may occur because permissive regulation, competitive reactions and elevated public-market equity create a temporary window. That does not protect investors: buyers care about founders and technology, not the cap table, and structured transactions already demonstrate that distinction. “Why wouldn’t they just hire the founders for the same package?”
At a 30–50x return, Venky wants the fund to ask whether it should sell perhaps 10–15%, ideally alongside founder liquidity. Locking in gains makes both founder and investor more willing to hold the remainder. Menlo generally will not sell everything unless the company itself is sold or it lacks a relationship with the founder.
7. Fast deployment is defensible only when vintage concentration is explicit
Menlo’s commitment model distinguishes passive seed exposure from a large check and board seat. In the Anthropic/OpenAI case, that is why it stayed with Anthropic rather than also investing in OpenAI. Venky presents this as Menlo’s authentic choice, not an industry-wide rule.
LPs simultaneously requesting smaller funds and slower fundraising are asking for incompatible outcomes if AI really is the defining platform shift. Unlike Google, which Venky says raised less than $50 million privately, current AI businesses require compute and scaling capital; if one fund withholds it, a competitor will supply it.
Yet vintage diversification remains real. Menlo Eight deployed during a roughly ten-month period in 2000–01 and is the only fund in the firm’s 50-year history not to return capital. Venky does not prescribe a dogmatic deployment calendar; he asks GPs to explain their reasoning, downside plan and concentration transparently to LPs.
Scale itself guarantees nothing: Menlo Nine was a $1.5 billion fund raised in 2001, and Menlo Ten was $1.2 billion in 2004; both underperformed expectations and many LPs left. Today LPs demand DPI, but AI exposure remains strategically attractive because their private-equity books are often three to four times larger and heavily exposed to software disruption.
8. Capital structure determines who still has room to act
Wealth makes investors less afraid of failure and more willing to “go to the hilt.” Venky’s poker analogy is blunt: the player with the largest chip stack can see more cards and bully the table. That makes $30–100 million funds especially awkward when they require $1–3 million allocations rather than easy-to-fit angel checks.
He resists turning difficulty into impossibility. Venky estimated Sarah Guo’s fund at around $200 million and cited her entry into highly sought-after companies; BoxGroup offers another counterexample. But these are “the best of the best,” not construction templates to extrapolate: “There’s no magic strategy”—exceptional managers out-hustle competitors and bring unusual grit.
A related control problem confronts 2021-era software. Private-equity owners face AI disruption but can use majority control to act; many venture-backed “zombie SaaS companies” have dispersed cap tables where nobody owns enough or cares enough to land the ship. Venky’s range is severe: the best result may be “getting spooned”—recovering capital—while the worst is zero.
9. Capital allocation beats charisma when the stakes compound
Asked to choose between product vision and capital allocation in a scaled founder, Venky chooses capital allocation because it subsumes product judgment: leaders must direct resources toward the products that matter and the returns they can generate. A product visionary need not possess the reverse discipline.
His comparison is Mark Zuckerberg—praised for Instagram and other capital allocation—against Evan Spiegel, whom he calls a product genius while noting Snap shareholders have not been rewarded for seven or eight years. Harry’s stock-based-compensation concern sharpens the distinction between creating an admired product and compounding shareholder value.
Venky is not worried that wealth automatically retires top performers: “Money doesn’t change people, it reveals them.” People who merely acted motivated may opt out, while A players treat money as scorekeeping because they love the game. He does concede that concentrated wealth changes the Bay Area and amplifies housing prices when constrained supply meets rising demand.
His LP advice is to “look at the windshield, not the rear view mirror”: reported performance lags current ability by five to seven years, so LPs should ask successful AI founders—even those who rejected the fund—which partners they respect. Internally, complacency gets the savanna rule: lion or antelope, “you just have to run,” and the next meeting, investment and board session matter most.
Full transcript
At this point in Menlo's history, right, we are going broke. We are going for the grand slam home run. We want to see everything. We want to win everything. Full stop. It is a very disorienting, confusing time.
Each seed investment is an option bet. You're buying an option to see if it's an outlier. You never want to let your ego come in the way. My one lead ego is to make money for my investors. If there's an opportunity to make money on an investment, we should do it. The rest of this is all noise. The game has changed. You have to focus on IRR. There's no way for venture to be successful in today's era without the Mag 7 participating in everything you're doing. There's no limit to what a person can do as long as you don't care who gets the credit.
You have now arrived at your destination.
Venky, dude, I am so excited to do this. I am such a fan of your tweets. Who would ever call them blowhard, right? That's terrible commentary on them, and I was so looking forward to this. Thank you so much for doing it in person.
I love this. Thank you so much, and I cannot wait to see if I pass your test.
Dude, you'll pass my test. I want to use this as a real learning discussion for me because I want to build a firm like Menlo, and I want to learn from the wisdom that you've had now, seeing multiple different cycles. You just told me a story that I loved, and it was from 2 decades ago, holding a certain stock. Can you tell me that story and your takeaway?
A little bit of the past: a few years ago, I was at a firm called Globespan Capital Partners, and we happened to be investors in a company called Avanex, which is—nobody knows about this company—A-V-A-N-E-X. I remember the stock symbol even now. I was an associate and did not have carry in the fund.
Avanex was a big winner and went public. They gave the associates a chance to own shares of the IPO, so I bought some shares. I remember putting in the princely sum of $5,000. At one point, Avanex got up to $200,000. It was such a big portion of my portfolio.
My wife, who's much smarter than me—she was my fiancée then, and we were getting married—said, "Hey, why don't you sell some so that we can have something for a down payment on the house?" I was like, "No, no, no. Avanex is going to go up. Optical components are a critical part of the Internet bubble. It's going to go higher. We're going to make $1 million on it."
You know how the story ends, right? It drops 90%, and I think I sell it for around $8,000 or $9,000. I call it the most important lesson I learned from a 90% loss: at some point, you should take some chips off the table.
I'm not sure what to take from that, because I remember having Jake Sapraun from Emergence on, and when he broke down Emergence's returns, you just saw this one meteoric outlier that returned 90 to 90-.
Viva.
Well, Veeva, yes, but it was actually Salesforce.
Wow.
If they had held it longer and longer, obviously it would've been even more meteoric. I guess my question is: what should we take from that? Because we also see the dangers of selling too early.
Agreed. A lot of this advice depends on the context of who you are as a person and what your balance sheet is. At this point in Menlo's history, we are going broke. We are going for the grand slam home run because we've had home runs before. We have a history of putting it on the table.
As a 24-year-old with very little in your bank account, when you have that kind of, for me, Avanex game-changing money, it just makes economic sense to take some off the table. I do think the advice is that there's no one-size-fits-all for these things.
Did you say you're going for broke? All hands to the pump. We are going for this. Does anything change with that mindset internally? Is it more aggression, more willingness to pay up, or more willingness to have less ownership? What changes with that?
What we mean is that we are going to fight and try to be in the defining AI companies of our era. We want to see everything. We want to win everything, full stop.
I want to start with a concern, which is that I don't know what business we're in anymore. Venture's not venture anymore. I have my team come to me and say, "Hey, we can't find anything under $100 million." I said, "Wow, that's a high price for a pre-seed or seed round." They said, "No, no, no, Harry, that's the size of the round." Thank you. This is not venture. What am I to do in this world, and can you invest without a billion-dollar fund?
Venture has changed, but I also think that you can't take a snapshot in time and draw a conclusion. A dot is not a line. Right now, you're right: every AI company wants to raise hundreds of millions of dollars, and I'm surprised they only said $100 million, because there are some new labs that want to raise billions of dollars.
Yeah.
They all have arguments for it. It is a very disorienting, confusing time, I will admit that, but I also think these things change quickly. You don't want to necessarily draw your long-term strategy from a snapshot in time.
These things change quickly. Do you play the game on the field, as Bill Gurley says, or do you call time out and say, "You know what? I learned from 2021. You know what I wish I'd done in 2021? Less."
This is a really hard conundrum for professional investors. You're referring to my tweet, right? The Chuck Prince quote is, "When the music is playing, you gotta dance." As a professional investor, the danger of not dancing is that you do not know when this ends.
I'll give you a story. There were a bunch of really smart venture firms during the dot-com boom that got in in '93 and '94, made money, and decided to step out of the game in '96 and '97. When they stepped out of the game, they missed out on '97, '98, and '99, and the LPs were like, "What happened? We invested in you because you're going to be at the cutting edge. You stepped out." They stepped back in in 2000.
Timing markets is really, really hard. I think you have to play the game, but I think you can play the game differently. You can choose to be more selective, and you can hopefully think about portfolio composition and position sizing as a way of mitigating what happens when the cycle turns.
Portfolio composition and position sizing: what do we do with both of those in a market like this? How do we change them?
I think you have to think about the venture portfolio as a bunch of options. Each seed investment is an option bet. You're buying an option to see if it's an outlier, and so you want to have enough of those to make sure you have an outlier. Then, when there is true quantitative evidence based on revenue and other quantifiable metrics that something is going to be an outlier, you position-size up.
To me, you have to think, “What is my fund size? How do I have enough at-bats?”—to use a baseball analogy—and make sure that you have enough at-bats. Then you only position-size up on the things that are already proven.
Do you think seed still really exists today?
If you want to go into the core AI world with the neo-labs, I think seed is hard.
But even AI application companies are raising $10 million to $20 million. The old $3 million to $5 million days, which were still quite large seed rounds, are gone.
Honestly, I think there are 2 things that impact seed investing today. One is the size of the round, and then you have this other sort of externality, which is these large funds—maybe including us—being somewhat indifferent to seed valuations because they're using that as an option check.
Because you are, aren't you? I didn't mean to put you on the spot, but—
Yes. We are trying to buy ourselves a seat at the table. At the cost of buying that seat at the table, we are somewhat indifferent to at the seed stage because our real goal is to size up and invest in them if they become outliers.
Thank you for making my life harder in that respect. You said you place these bets, so to speak, and then, when you see discernible traction, you can double down. I completely agree with that logic.
We're seeing strange numbers: contracted annual recurring revenue that's not actually annual revenue and isn't really live. You're seeing revenue run rate that's extrapolated from the best day in history, and then we multiply that by 365 days. There's a murkiness to this revenue that we've never seen before, which makes me feel quite icky in a lot of cases. Do you share that, and how would you advise me? What do internal discussions look like around that?
If any metric is measured by an investor and they put a lot of weight on it, it's going to be gamed, and that's just the nature of it. Maybe they should coin a law for it.
There are 2 elements going on. One, I'm blanking. I don't know if it's Keynes or another famous economist who coined the term “bezzle.” When there's a boom, the bezel is high, which means, like, it's, it's a notion that the embezzlement of things will be... It's not just that people are going to pick metrics. People are also going to have some interesting accounting techniques, which, by the way, will happen every cycle, and it's probably happening in this cycle. We're going to find out in the next few years exactly the accounting creativity of some of our founders and how some people gamed the metrics.
One good example of that during the SaaS wave was that a lot of investors put a lot of weight on net revenue retention. One way to game net revenue retention is to get a $100 purchase order—but it's better to get a $10 purchase order and then get a $50 purchase order a week later, because if you just got a $100 purchase order, your net revenue retention was 100%. But if you got the $10 purchase order and the $50 purchase order, it's now 500%, and the net revenue retention looks much better.
Once a metric is measured, it can be gamed, and that happens. To me, a lot of this comes down to whether the founders are really focused on building a business. Are they focused on terminal value, or are they focused on markups? I think you want to find founders and investors who are focused on terminal value.
Do you believe in kingmaking? I know that sounds like a strange question: the theory that multiple successive and quick rounds led by strong investors can really help increase the chances of a company being successful.
To me, that is a great example of Soros's reflexivity. What I mean by that is you have a company that does well, and because it does well and the revenue is growing really fast, it gets a quick markup. Because of the quick markup, it gets more capital, it gets to come on Harry's show, and then it gets more notoriety that allows it to bring in more human capital along with the financial capital. It grows faster, and that's all because of the markup.
These are good things as long as the revenue is happening and the core business is being built. But someone—a copycat—can look at that and say, “The secret is to have a markup.” A copycat investor might look and say, “If it's marked up, it's going to be marked up again.” Then reflexivity kicks in, and everybody starts acting that way.
This explains how market cycles work until they stop. One thing we know from Soros is that all reflexivity will eventually stop. We just don't know how or when. Until it stops, a lot of people can look very smart.
We don't know how or when, but we can play the game of predicting how and when. If you were to predict how, what are the first signs of this cracking?
I think usually the first sign comes with some major debt default. Generally, equity is never the reason why these things crack, because with equity, you write it down and just take the loss. Debt, on the other hand, comes with the expectation that people are going to get paid back.
Most of the cycles I know break because people lever themselves. If you see what happened with Leopold and Core Investor, when you have 4x leverage, it doesn't matter if you're right. You also have to get the timing correct.
He missed his risk-management class in high school, didn't he? Poor old Lehman.
When the music's going, I completely get you there. How do you feel about multiple-tranche rounds happening so quickly? I'm meeting founders very often who say, “We're doing a round this week at a $100 million valuation, but then we'll be opening up the second tranche later next week at $200 million because we've got so much demand.” This gives me the shivers. I feel like I'm in We Buy Any Gold or We Buy Any Car.
I feel like in every cycle you get the innovators, then you get the imitators, and eventually you get the idiots. I think the innovation of tranche financing was the notion that I can get “build-with-me” money, use that build-with-me money at a lower valuation to get just money at a higher valuation, and then eventually transition to pure dumb money.
I don't need all money to be the same. I will bring in some investors who are actually going to build a company with me, then I'll also bring in some capital, and eventually I'll bring in some very low-cost capital. That was the intention.
But, like everything else, now everyone's doing it, and it's no longer tied to the quality of the company. It's become another technique for people to use. These things initially start with the core of the idea, which is actually a good one: “I want to raise capital, but I want to distinguish between capital that adds value and capital that doesn't add value.”
Will you do it as a firm if you come in at the latter tranche?
It absolutely depends on the situation. We have been on both sides of this situation, and I think if the company is interesting and the founders are special, absolutely.
Really?
Yes. At the end of the day, I never care about what other people invest or what they do. I'm looking at this round and saying—
Are you not hurt by the fact that they're saying you're legitimately less valuable than Peter Fenton, who we're letting in at half the price?
Peter's amazing. I think the biggest thing I've learned over time is that you never want to let your ego get in the way. My one and only goal is to make money for my investors. If I can make money for my investors, who the hell cares?
Have you ever let your ego get in the way? I have.
100%.
What happened?
I think you get caught in ways of negotiating around valuation or being in a syndicate. Sometimes you're offered an opportunity where you think you're being offered a small piece, and you say, “Well, I'm too big for that piece.”
I think in this business you have to have a high degree of humility, because every week I get hit and punched in the face by things I don't know. The biggest mistakes are when we get too caught in our ego.
Look, the reality is simple. We raise money from institutional investors with one and only one goal, which is to return more money to them. If there's an opportunity to make money on an investment, we should do it. The rest of this is all noise.
I think too often, because venture capital tends to be dominated by personalities, people get caught in these things. You probably don't know a lot of people at Goldman. Everybody can say David Solomon, who's the CEO, but the idea is that Goldman makes a ton of money and those people just go do their jobs. Too often in venture capital, because there are so many personalities, it becomes more about who we are and our egos as opposed to just doing the job.
I think that's forced by the fact that we're fighting for constrained supply there.
If you're looking at, say, Goldman's public markets team, you can buy Nvidia, I can buy Nvidia, and they can buy Nvidia. It is a free market. Here, we are both competing for Max at Ligora, and if he takes your check, he won't take mine because there's 1 lead check. So we have to have personality. We have to sell ourselves because there is a constrained supply, no?
Yes. What you say is absolutely true, which is that you have to have these 2 dualities and manage them. One is you have to have a personality. You have to be able to project a sense of differentiation, right? Because why does someone choose Harry and not me? It's because they like Harry.
And good looks and charm.
I see that in person even more so.
Yeah.
But I think if you get caught in that and get so immersed in it, then you lose a sense of what the core purpose is, right? The core purpose of having that personality and charm is to make money for your investors. That's why it is, right? If there's a time for you to make money for your investors where you have to let your ego take a backseat, you should do it. That's the right thing to do.
I'm not saying it's easy to do. I'm not saying I've done it. But it's the right thing to do. It's kind of like, I know I've got to eat right and exercise. I know that. I don't do it often, but I know it's the right thing to do.
Yeah, but Gymkhana is so good. Some things in life are worth it, like butter chicken.
I'm a Dishoom.
Oh, you are?
Ah.
Oh, well done. Don't worry, I like Dishoom, too. We said about price: we're a little less focused on it when it's early. There comes a time when it does matter. With the greatest of respect—
Oh, say it. Say it, man.
Well, men, they kind of pay up.
And for all you entrepreneurs out there, we definitely pay up. So definitely call us.
Yeah, you do, and every time I'm like, “Pff.” Man's paying up.
Mm-hmm.
And you proved me right. You're right, and I'm proved wrong when I'm like, “God, they're not disciplined on price.” So I guess I'm questioning: do we just need to completely reshape how we think about terms and market sizing?
Let's think about when people pay up. People sometimes pay up to be able to win the deal. Sometimes people pay up because they're able to see a bigger tab than the other investor. In those cases, you're not actually paying a higher market price; you're able to see that the opportunity is bigger, and therefore you're willing to see that possibility.
Sometimes you're going to be right, and sometimes you're going to be wrong. So to me, I don't necessarily think it's just price. Sometimes you don't see the tab, you're just trying to win the deal, and that's the price it takes. You're just a clear price taker. That happens, too.
The problem is, venture is an asymmetric game. You can lose the dollars you invest, but you can make 10X if you're right. That asymmetry means the sins of omission are way higher than the sins of commission. What I mean by that is, you only see the deals we do, right? You don't see the deals we pass. But the most expensive mistakes venture capitalists make are the deals they passed, not the deals they did.
When you say that, what's the most memorable pass that haunts you? What is it?
My most memorable pass was that I was a young board member on a company called Plaxo, which had an incredible board: Mike Moritz, Ram Shriram, Tim Koogle from Yahoo, little unknown me, Sean Parker, and Todd Masonis and Cameron Dren, who were the founders.
Sean had some challenges on that board and was asked to leave. Because I was the only person within 10 years of his age in that group, he was telling me he was going to Boston and was going to work with this college dropout. He said, “You should get involved.” And I'm like, “Sean, you just got booted off this board, and I have no idea what I'm doing.” I didn't even take that meeting.
I probably had the opportunity to write a $50,000 check. Those seed rounds were different. They were $1 million seed rounds.
That's a tough one. What was Sean like back then?
The way he described Plaxo, his vision worked out. He understood virality and network effects, and his thought process around what happened with Napster.
My rule of thumb is I'm always looking for people who are incredibly good at communicating very complex concepts in a simple manner and just have insight. Sean had insight around human behavior and complex concepts, and could boil it down in a simple way. He was a very good communicator.
What a character.
And he gets to have Justin Timberlake play him, so it must be all right.
I mean, it's a pretty cool one. Drops the “the.”
Yeah.
Love it. And we actually did that. We were the 20 Minute VC—
Oh, good. There you go.
—now it's just 20VC. Yeah, yeah, yeah. Thanks, dude. I was talking to Amy beforehand, speaking of the founders you backed there.
Amazing partner of mine.
Amazing partner of yours. She said that you care a lot about understanding what brought founders together. Hearing you talk about Sean there made me think of this. Why do you care about what brings founders together? And are there any patterns or signals that excite you?
I think the company you build is the team you build. So much of the DNA of a company is set by its founding team. What brought them together, why they thought, in a world of 6 billion people, they should be the people to do this, and how they think about each other's strengths and weaknesses—I think these things are like a precog from Minority Report that tells you how they're going to make decisions and how they're going to build the rest of their team.
I think it gives you a clue about who these people are. Ultimately, I think a company's culture and DNA are going to be shaped by the founders.
You can ask 1 question that you find most revealing of a founder's qualities. Doug Leone's, to me, was the one I remember most, and he always says, “What's your worst reference?”
That's a great question. I generally ask: imagine your 5 best friends are in a room, and if I had to ask them for 3 words to describe you, what would those be? That's a question I normally ask people.
I'll tell you, I listened to Mike Moritz in an interview, and he asked a question—his favorite question is, “If you could go back in your life and change 1 thing, what would that be?” I think that's a pretty interesting question.
If I were to ask you what you think about yourself, it's harder. But when you think about your friends, you can externalize it, and that gives you a clue about how the people around you think about you. It also tells you your self-awareness, because usually after I do that, I also do references, and I'm going to try to see if the references match someone's self-awareness.
It's actually okay if you know your weaknesses, because then you have a much better chance of managing them. It's the people who are blind to their weaknesses who usually have challenges.
Don't worry, my weaknesses are revealed in the comments section of every interview, so I see them glaringly. One thing that's been uniform across the industry is that we've seen ownerships go down. Even the vaunted Benchmark now takes less than 10%, and—
I thought they said 20%, 20% or bust.
Maybe they still stick to that message. I love the Benchmark guys, absolutely. But does ownership matter as much anymore?
Of course it does. Ownership always matters, but I think you have to think of that relative to the opportunity, right? What I mean by that is, would I love to have 20% of a company? Sure. But I'd rather take 2% of a trillion-dollar company than 20% of a $100 million company, right?
So you'll do deals now for 2% or 3%?
Well, we do. Anthropic—we own less than 2%. My point is that when you think about ownership, you can't think of that in isolation.
But I think you're either in the ownership game or you're in the money movement game.
I disagree a little bit. I think when you're making your option bet, you want to have ownership, because then it's not clear. Let's say you know it's an outlier. If it's an outlier company, then you're in the capital-invested game. Prior to it being an outlier company, you have to be in the ownership game.
Your best situation is that you are in the ownership game in an outlier company, and then, because it's an outlier, you go into the money-movement game.
No, I thought you said the ownership doesn't matter before it becomes an outlier, because you're there for the information. When it does become known, it becomes a money-concentration game.
You want to have enough ownership, though. I mean, you look at Higgsfield with my partner Amy. She killed it. She got 15% of the company for a $5 million check. You had Alex on your podcast—an incredible entrepreneur and an incredible business.
So in that case, we got the ownership. And then we also had the opportunity to size up.
Did you?
Yeah. We invested.
Do you get my rationale, though, that it doesn't matter if you have ownership in the first place?
What you're buying is the information to size up.
I get that. If you're asking me whether it's better to be in the company regardless of ownership or not be in the company, yeah, it's better to be in the company. But it's even better to be in the company with ownership because now you've actually gotten your ownership that's gonna drive real returns.
The problem is, once it's an outlier, everybody knows about it. It's no longer a selection game. It's just, okay, can you get access, and can you—it's a position-sizing game. There's no alpha there, and that's the truth. In the AI greatest hits, everybody knows these companies.
How much of your fund will you put in a single company?
I don't think we would put more than 20% of—
Have you gone up to 20% before?
We have hit 20% on one company.
Whoa. What company?
Anthropic.
I mean—
But it—
Fair enough. Yeah, yeah, yeah.
It's gotta be an exception, right?
Yeah. I bet that was a hard conversation: “We 10x'd this year. We 10x'd last year.” “Okay, Venky, let's do it.”
But I do feel that you have to think about the question of ownership and concentration as one. What I mean is, where was the company? What information do you have? How much conviction can you have as an outlier company?
The thing about position sizing is you want to position size when the data is there. If you position size it ahead of the data, then you're taking a lot more risk. So the question is not, did you put 20% of the fund into a company in one check at the beginning of the fund, or did you ladder up to 20% on the basis of new data? Obviously, it's much better to ladder up on the basis of new data.
I think in an era where venture capitalists are gonna have ownership come down—I mean, I wish we could get 10%. Even 10% is hard, right? The way you're gonna win is you're gonna establish a position and then size up as a company does well, so that you have sized it commensurate to the outlier opportunity.
Totally get you, and I get that. Everyone says that ownership doesn't matter so much because outcome sizes are so much larger than they've ever been. They are. That is a valid answer.
My question is, are they on the whole? Do we just have a breadth of companies that will be much larger, or is it really just a handful of Anthropics and SpaceX and cursor on the small end at 60 billion, which is still enormous and amazing? But is that a good enough justification for ownership going down?
I think the problem comes down to your portfolio composition, right? If you are in one of those outliers, I think you can survive with low ownership. But what happens if you are not in these big outliers?
Essentially, you're playing a game, to use baseball analogies, where there's only grand-slam home runs or strikeouts. There's no singles, doubles, or triples, right? In cricket terms, it's like only scoring sixes and not having ones and twos.
The problem with that is that if you don't score a six and you don't have the ones and twos, that's gonna be a tough fund. Part of getting ownership is giving yourself some insurance that if you missed out on the outlier, the mid-sized outcomes can still move the needle for you.
But will you do singles and doubles?
No. The goal is always to score home runs, right?
Yeah.
But sometimes you strike out. If you strike out all the time, that's gonna be a tough fund. So the idea is that you wanna at least say, “Okay, I went for the home run and I got a triple.”
But I just don't think founders are aware, and I say this and people always get at me. I think they kind of miss the point because I say it lovingly, for awareness, for founders: the game has changed. Going from $1 million to $4 million, then $4 million to $8 million, then $8 million to $16 million, and then, Venky, in 5 years' time, we're gonna hit $30 million—that's an amazing achievement. But it is just not enough to get venture excited today. Do you agree with that?
Yes, I agree with that. Again, it's a snapshot in time because you're seeing companies—
But do you think venture will ever go back to being excited about that?
Well, they're not excited about it today because they're seeing companies go from $1 million to $10 million to $50 million to $100 million. They're getting to $100 million in 3 years, or in some cases they're going from $0 to $1 billion in 18 months, right?
When you see those kinds of companies, of course you wanna do those. But that's because we are in a moment in time where there are certain trends allowing you to do it. I don't think this continues forever.
This is where I think you have to take the long, long-horizon look at this. There were companies who grew fast, but there's a combination of things that make these companies grow fast today that may or may not continue.
When they grow as fast as they are, the rounds come thick and fast and the prices are high.
Yeah. I mean, you look at Instinct. God bless. I wish we were in. They've gone from, I don't know, $250 million to $10 billion in 10 weeks.
Would you have done that round at $10 billion?
Smart people have done it. We are in Town, which we love and think very highly of, and we're excited about that. I think there's something going on there. There's a true phenomenon. What I don't know is their data, what it costs for them to keep growing their user base, and how the Muse launch affects their growth.
Can I ask you, everyone kind of goes into a lot of investing now with the idea that there's downside protection? No is incredible. It's in a very strategic space for the incumbents. Worst case, one and a half billion McPRAF. It's a no-brainer for Microsoft to do it as an addendum to Copilot, or for Apple to do it. Jesus, Apple, please do it. Do us all a favor and save us from Siri.
Do you think that downside protection—“Ah, don't worry, the incumbents will buy it”—is okay to have, or quite a dangerous mindset to have?
I think you can easily rationalize a lot of things if you take that mindset. The problem is that, again, you threw out this $1.5 billion number casually because we are in this environment where AMD is buying a company for $8.5 billion, Nvidia bought Hugging Face for $14 billion, and Stripe bought OpenRouter, allegedly, for around $8 billion.
Allegedly.
Allegedly.
Allegedly.
Allegedly.
Yeah.
I think we have to say these are points in time where companies are doing it. It may not be that way. Today, it feels like $1.5 billion is, “Oh, no big deal. If I'm right, it's gonna be worth $100 billion or $200 billion. If I'm wrong, someone's gonna pick it up for $3 billion or $4 billion.”
By the way, that's what you're referring to with my tweets. I wrote this thing about how, if you go back and look at the dot-com era, Nortel bought Kairos for $3.5 billion. Lucent bought Chromatis for $4.5 billion. These were companies with no product and no revenue, just teams, and they bought them with their stock.
It felt very similar. In fact, I believe Jeff Yang from Redpoint, a legendary investor, had this quote in The Industry Standard, which is a magazine that's no longer in existence. He said, “You know, there's no risk in venture capital. If the company's successful, it'll be sold for billions. If not, it'll be bought for the talent stack.”
It didn't quite work out that way on the other end of the cycle, after March 2000. So I go with trepidation, but I just wouldn't take the mindset that some large strategic is gonna buy my company for the talent stack because they don't care about the investors. They care about the founders. Why would they do that? Why wouldn't they just hire the founders for the same package?
Well, in a lot of cases, they kind of are in these structured deals—
Right.
Let's be honest, and screwing the investors.
So you've seen that, and you can't take that—there's no reason for them to take care of the cap table.
Do you think about the dilutive nature of businesses today? What I mean by that is that we are suffering more and more dilution as an investor class than ever before, and it's a better time than ever to be an employee, given the levels of stock-based compensation, or SBC, for people. Do you worry about that? Do you think about that? Should I worry about that and think about that?
For sure. We look at whatever we invest in at the seed round, and we assume that by the time we sell or exit the company, if we own 10%, we would have 3.5% to 4%. We expect 60% dilution from the point of our first check, right?
That's a combination of dilution from financing, but it's also dilution from option-pool expansions. You have to really think of yourself as, whatever ownership you bought in your first check, it'll only be 50% by then, at the end.
The interesting thing is that it's very common in a lot of companies we're seeing today. The other interesting thing is that companies are sometimes scaling so fast, à la OpenRouter—Alex, a friend of both of ours—that they actually don't take that much dilution because they scale so fast and so efficiently. You suffer much less dilution. So it's almost a tale of 2 dilution worlds. Do you know what I mean?
Yeah. It's a function of time.
Yeah.
So the way to think about it is that—and I don't think we spend enough time in venture capital thinking about that.
We should say, “What is the time horizon you’re going to hold the company for?” Because the time horizon will determine your dilution. Part of the reason your dilution is lower in some situations is that companies have quick exits. They grew their value quickly, and they have quick exits.
That’s a double win. When your time horizon is long, there are 2 hits: your IRR gets hit, and you’re going to have meaningful dilution.
Did you think of that when investing? What really is the ramp? There are businesses in the ERP space where they’re like, “Ah, but the revenue’s such high quality, Harry. I get you. It’s not as fast as your Higgs Field or your Ligora, but it’s so high quality.” And I’m like, “Yeah, fuck, it’s slow.” Am I wrong to think that?
No. I think the velocity of the business is very important for venture capitalists, right? The velocity will determine a bunch of things. The other reason why your dilution goes down is that if you have a fast uptick in valuation, the amount of ownership you have to give for your next set of human capital is a lot lower, right?
You’re a $200 million company, and you’re giving 2% of the company to hire a senior executive—that’s pretty meaningful. You quickly become a $2 billion company. You don’t need to give that much; you’re going to give RSUs, and you give the same person $20 million, which is 0.1%.
DPI or IRR?
Both. Maybe, if you can. I do think, actually, that you can’t have IRR without DPI. I think what you’re trying to ask is, “Hey, will you settle for a larger DPI over a longer horizon, or do you want quicker DPI with a faster IRR?”
I think the reality of venture when I joined—this is now dating myself—28 years ago, people didn’t focus on IRR. People focused on cash-on-cash return because IRR took care of itself. I think in today’s venture, the game has changed. You have to focus on IRR.
You know why? Because there’s no way for venture to be successful in today’s era without the Magnificent 7 participating in everything you’re doing. Every venture company is writing a tax to Nvidia in some way, shape, or form, writing the tax to a hyperscaler in some way, shape, or form, and possibly writing a tax to the foundational model in some way, tax or form.
So if you’re going to be successful, you're gonna be writing a tax to all of them. All of them are available in the public markets, or they will be soon, for someone to invest in a no-fee, no-carry index fund. You have to think about your IRR as, “I’ve got to beat that by 1,000 basis points to justify anyone giving you capital in the private markets.”
You mentioned Town. I had JD on the show. I really like him. I’ve known him since the cloud days. I’m pissed off about that one because he started the company when he left. I remember talking to him about it when he started, and he was doing something in some terrible space. No offense—he’ll agree with me. And then he obviously pivoted.
In tax. I think they were doing something in tax, and then—
Thank you. I’m too old for this shit.
If you’re too old, what am I? I’m ancient.
You’re a spring chicken. And for anyone watching, they’ll see that you look much younger than me.
But my question to you is, we obviously know what happened with the Town round in terms of the competitive nature and dynamics there. I don’t want to go into that. What I want to go into is: does competition matter for VCs to invest against now? It seems like Andreessen has 3 companies all doing the same thing, and many big platforms do. Does it matter if there are many players in the same space anymore?
I mean, this is a personal preference, right? Culturally, for Matt, Shawn, and me, we like to be committed to the entrepreneur. The situation has to be specific. If we take a board seat and write a big check, then we want to be committed. If you’re investing in the seed round and you have a small check and you’re a passive investor, that’s a different issue, right?
But when we make a commitment to the entrepreneur, we want that to feel like a 2-way commitment. We expect them to put the interests of their shareholders first and commit to it, and we as shareholders need to commit to them as well. That’s why we didn’t invest in OpenAI. We only stayed with Anthropic.
There’s no shade. Again, venture is changing in a way that multiple people are doing different things. I think you just have to figure out what is authentic to us and our values and live by those. For us, when we make a big commitment to the founder, we think of it as a 2-way street. They commit to us; we commit to them.
One thing that we see a lot today is the compression in deployment timelines. In other words, people are investing much faster. All the LPs that I speak to are just saying, “God, Harry, Jesus. Everyone is coming back to market so much quicker. They’re bigger.” Is that okay, or is that a sign of a peak bubble?
Yeah, you know, it’s very interesting. LPs want smaller funds, and then they want you not to come back quicker. The problem is that 1 of those 2 things can’t be true. If the opportunity we have is real, and AI is the biggest economic platform shift of our lifetime, and you want smaller funds, they’re going to come back quicker.
There are also large funds that are coming back quicker, so that’s a different issue. But I think the time we are in is 1 in which you’re seeing companies grow so fast and they need capital to grow. This is not a situation where you can grow without capital.
This is not Google. Google, if you go back, probably raised less than $50 million in the private markets. You can’t do that today in AI. You need compute; you need to scale. To me, because you’re seeing them grow so fast, the capital needs are growing. If a venture firm doesn’t provide it, they’re going to get it from their competitor.
So, actually, if managers are deploying a fund in 18 months, LPs should forgive them.
I think the LPs should ask questions and say, “How have you thought about it? How are you managing it? What’s going to happen if things go wrong?” Vintage diversification does matter. People have to be conscious about that.
When I look at Menlo’s history, the 1 fund that wasn’t successful in Menlo’s history—we have a 50-year history—we only had 1 fund that didn’t return capital, which was Menlo 8, invested in a 10-month period between 2000 and 2001. That was not quite the outcome we wanted.
Menlo 8.
Menlo 8. But I bring that up because I do think time diversification matters. By the way, Menlo 7 was 1 of the best funds in Menlo’s history.
Yeah, but do you remember Accel 2005, just before the Facebook fund? They had massive LP churn because they went and did a load of cleantech and biotech, and it was not good. And then came the Facebook fund.
So to me, I just bring it up as, look, as GPs, you’ve got to take the fiduciary duty you have to your LPs very seriously, and you’ve got to balance that decision. What I do know is that you can’t have dogmatic rules. You have to play the game on the field.
Then you’ve got to communicate what you’re doing in a transparent way to your LPs and tell them what’s happening. Some LPs are going to be like, “Okay, I agree with you. I want to play.” Some people are not, and you’ve got to respect that. But the point is that you might have no choice but to play the game this way.
Did you ever scale out of an LP class? What I mean by that is, the funds now are reasonably sized. They’re not egregiously sized. You’re not David George asking for the U.S. Treasury, but you’re $3 billion. It’s a lot of money.
For some LPs, they’re like, “It’s a lot.” Was there a time when you scaled out of endowments, say, and suddenly you had to be pension-fund invested?
Our anchor tenant has historically been the Washington State Investment Board, which is the public-sector pension fund of the State of Washington, from an SLP, by the way. I highly recommend them to anybody. They’ve been our anchor tenant since 1981, so we have never had a reason to scale out because public-sector pension funds have been a part of our LP base.
It’s a little bit of a cultural dynamic. I think the founders of Menlo came from very humble beginnings. They both grew up in a house with no running water or toilets. I think John was orphaned very early. He was a scholarship student at MIT.
They love the idea of working for public-sector employees because that felt like working for their parents, and these people look more like their parents than their children.
Love that. So there wasn’t a fund where LPs went, “Oh, Venky, you’re getting pretty big now. I think you’re just scaling out of our sweet spot”?
No, that wasn’t the case. We raised our first billion-dollar fund in venture capital. Menlo raised Menlo 9 in 2001. It was a $1.5 billion fund. Menlo 10, which was raised in 2004, was a $1.2 billion fund.
Those funds did not perform as well as we would have liked, and many LPs did leave us.
You manage a lot of the LP conversations today, correct?
I do. Matt and I do a lot of them, yes.
What do you hear from them? As I said, I hear deployment time is down: people are investing much faster, and the funds are just getting bigger. And then I also just see mimicry, which is—I’m calling this out because it’s a compliment to her.
I never shit on people other than LPs.
That’s okay.
But every LP just wants Sarah Guo’s fund.
Yeah.
I completely agree: Sarah Guo is incredible, and you should want her fund. But there’s this complete herd mentality.
Sarah and Mike are amazing—
Amazing.
—and there’s no question about that. I spend a lot of time with them and with LPs, and I think, first of all, a lot of LPs have 2 complaints. One, they’re like, “Enough TVPI. I need to get some DPI.” So I think if you deliver DPI, you’re already on the right side of the table. I think it’s easier to come back to them to ask for more capital when you deliver DPI, right?
Second, I don’t think people can afford not to be in the AI economy, and I’ll tell you why. Most of them have much bigger private equity portfolios than they have venture portfolios. In many cases, they have 3–4x exposure to private equity. A lot of private equity over the last few years has been software, and those positions are directly impacted by AI. If you want to hedge against your private equity portfolio, you’ve got to be in the AI economy.
That’s the piece that forces them to come back. If you are someone who has given people DPI, and you can credibly make the case that you’re going to be a player in the AI economy, I think you can raise money from LPs.
You’ve got to have given DPI. We see companies scale faster than ever, as we’ve said. We see prices that are very high. How do you think about the internal conversation of, “Whoa, X company is now valued at $10 billion. Can we take some chips off the table?” What does that discussion look like, and what are the lessons on how to sell successfully?
I think you have to step back and look at any situation in which you have a 30, 40, or 50x return on your dollar and ask yourself, “Should I take some off the table?” I think the right time to do that is when the entrepreneur is thinking about taking some right off the table. If you were to work in conjunction with them—
What if it’s not material? I’m using this as a consulting lesson. You can invoice me later. I have a company where we’re 40x up.
Yeah.
You’re like, “Wow, fantastic.” You’ve got $100,000 in there. Return $4 million back to the $100 million fund that it’s in.
I don’t think it’s a size issue. To me, it’s just, look, lock in the gains. If you go back to the SaaS portfolio in 2021, there were valuations done at, let’s say, pretty high prices. If people had taken 10–15% off the table, even if it’s small, it locks in gains and allows you to go long.
The other thing I tell entrepreneurs is that, just like when you take some chips off the table, you’re more likely to go long, so are we, right? We can now afford to go long with you, and so it aligns. To me—
Will you ever sell all of your position?
Generally, no. Not unless the company is being sold. I’m not interested. I think that’s a different situation. The only time I think it’s different is if you do not have a relationship with the founder. But as long as you’re in, you’re going to ride. We ride and die with our founders.
Jason Lemkin says on the show, “Whenever a founder leaves, I ride it to zero. When a founder’s gone, zero, zero, zero.” Do you find that to be the same when the founder leaves? You’re like, “We’re supportive, of course, and we’re still here,” but mentally you’re like, “That’s a zero.”
My friend and your friend, Nikesh Arora, would disagree with you and say he goes on founder mode. Look, there are people like Nikesh and Jeetu Patel at Cisco. They go into founder mode as executives. It’s sort of an insult to people like that when you say, “The founder leaves.” Look at the situation. Who replaced them?
Founder mode is a mode of working. It’s not tied to anyone personally. I think anyone can be a founder in terms of working in a founder mode, and I think some people do. Frank Slootman joined Data Domain, Snowflake, and ServiceNow. In each of those places, he acted like a founder. He didn’t act like an executive.
By the way, Nikesh, please don’t kill me. I love you more than ever, and I’ve always loved you, and it was Venky who said it. It wasn’t me who said it. I’ll give you Venky’s address later. I’m going to go get a brick through my window.
You’re definitely getting it from Nikesh.
I’m terrified of Nikesh. Are you kidding me?
Can I ask you, then? We see so many sales now. Fei Fei Li sells for $8.2 billion. It’s amazing—a phenomenal exit. Well done to everyone involved. Yesterday’s news. I mean, OpenAI is so yesterday’s news we’ve all forgotten about it. I don’t mean this glibly or anything. I know that sounds so much like a child of this ecosystem, which I’m not, sadly. Are we just going to see a load more exits now?
Yeah, I think you’re going to see more because I think there’s competitive pressure. There’s also this notion that we have a regulatory regime that will let you do M&A, right? There’s been a backlog of M&A that was supposed to happen. It didn’t happen because we had a different regulatory regime. There’s a notion that this may not continue forever, so, one, you have a window of time.
You also have competitive pressure. When AMD buys a real-world model, does Nvidia need to do something? Do other people need to react? I think every acquisition forces a bunch of competitive dynamics that we have to consider.
Then people have equity prices, right? AMD is now a trillion-dollar company. $8.5 billion is still, I think, less than point one percent of the company, right? So you can do stuff because of this combination of things. There’s also the notion that anything that lets you catch up in the AI wave is very highly valued. Did Meta do a good job paying up for scale? I think they would say yeah. If you look at the market cap add of Muse to Meta, maybe that fifteen billion seems cheap now.
I’m also so happy for Zuck. It feels like he’s almost got a co-founder in Alex Wang who he can delegate some of the shit to. Do you know what I mean?
Zuck is a great capital allocator. Go back and look at the history of his capital allocation; it has been phenomenal.
Best of CEOs.
He bought Instagram for $1 billion. He has executed.
He bought Navo for four hundred million, which allowed him to see everything that went. So smart.
I think they’re incredible technologists, but I think there are very few people who are incredible technologists and good capital allocators. Zuck is right up there.
If you could choose 1 skill for a founder at scale between capital allocation and product visionary, what would you choose?
I’d choose capital allocation. By the way, capital allocation by itself also captures product vision, because you’re allocating the capital to the things that matter. In some ways, part of the dynamics of deciding on capital allocation is which product direction you need to go.
But the other way is not true. There are some people who can be great product visionaries but who might not think about what the return on that is going to be.
Evan Spiegel, love the dude. I mean, free candy every year. SBC through the roof. Are you a shareholder of Snap?
We are not a shareholder of Snap, but Ev is a product genius. There’s no question about that.
Genius.
Right? His vision for Snapchat and what he executed—I think it would be fair to say you have not been rewarded for being a shareholder of Snap, at least for the last 7 or 8 years.
Not been rewarded?
I was trying to be polite here.
That’s like giving Titanic an 8 out of 10 in the holiday review book. That’s incredible.
Not being rewarded.
Not been rewarded. Blowhard. Yeah, no, that’s a good way to put it.
Are you worried by how much money is being made by people? I’m seeing researchers at OpenAI walk out with $30–40 million.
Here’s the thing: I’ll always believe this—money doesn’t change people; it reveals them. People think money and power change people. No, they only reveal them.
If you’re an asshole before, when you have money and power, you reveal that. What I have found is that the people who are really motivated are going to be motivated even if they have lots of money. The people who are not motivated, who are acting like they are, will opt out when the money shows up.
To me, it won’t change for the A players, because for the A players, money is just a way of keeping score. What they love is the game.
So you’re not worried about house prices in the Bay Area and the inflation that we’re going to see with IPOs from SpaceX, Anthropic, and OpenAI? That worries you, or not?
Of course it does. It changes the character of the place. But the real issue we have—and this is an issue in California, hopefully not in London—is a question of supply. It’s not a question of demand.
At the end of the day, we have tremendously increased the cost of, and the process for, building a house. There’s no supply coming in, so any uptick in demand results in prices going up. The way to address that is not to worry about the demand, but to increase the supply of housing stock. We just do not have the collective willpower, and this…
For a progressive state, there's more NIMBYism in California than I expected, and the NIMBYism prevents you from building more housing stock.
I saw a tweet where you said something. You responded to Brian Armstrong: “I do my work.”
Okay. All right. This is dangerous.
Yeah, it is dangerous, but I'm joining you on this side if this is where you're going. You said, “I appreciate your leadership through the woke times.”
I think what I particularly appreciated about Brian is that he laid out his principles of what he believed, and he told people, “Hey, if you really want to engage in political activism, then Coinbase is not the place for you because we do not want to have political dialogue here. If that's important for you, you should go and find a place in which you can do it.”
I think that takes courage to say, but it's being true to what he wanted to do. To me, that's the most important thing: try to be authentic to who you are. I appreciated him being authentic when I think it came at a cost. He was castigated in the press and maybe on Twitter, and he had people leave.
But I think he ultimately said, “We want people who are authentic to Coinbase values articulated by me, the founder.”
Have you ever been inauthentic to yourself?
I think there are times when you say certain things to founders because you want them to like you or you want to win a deal that may not be truly authentic. What I'll tell you is that I have dealt with my own insecurities and feeling like an imposter, and I've gotten more comfortable in my skin now. I just don't do it.
If it means I have to say something inauthentic to me to win the deal, I'd rather not win it. But that's easy to say because I'm at the point in my life where that win doesn't matter. Of course I like to win, but it's not going to change my life.
I always say it's very different when you're 25 years old and you're trying to build your career. You do whatever it takes to win. In some way, morality is a privilege of the people who already succeeded. It's easy to be moral now when you already have the things you have.
The question is, will I be a moral person if I were to go back 20 years ago and start there? That's the real test, and I don't think I lived up to that test as much as I would like.
Are you a better investor now that you're richer?
Yes. You're not as afraid. You're not afraid of failure. You're willing to go all in and go to the hilt, so you can go for broke more easily.
Think about it on a poker table. The guy with the big amount of chips has so much leverage to win, right? They see more cards. Ironically, this is why I think the way our capitalist system is set up, the rich are going to get richer, because they have more opportunities to be the bully at the poker table.
Does that mean emerging managers are just in the old starvation game? Forgive me for this, but I don't like binaries. I'm fucking media, so you kind of have to do binaries. “It depends” doesn't sell. The $30 million to $100 million funds are just the worst place to be.
Yes, they are today. That's a tough place to be because you're playing at a poker table where people have such high chip stacks.
I think they were five years ago, dude.
I think what happens is, if you're lucky enough—and I don't know if this is true, but I'm sure if you were to go and look at the cap table—there was some small investor who wrote a check. Anjan wrote a check into Anthropic. Maybe he didn't have a fund then, but he wrote a check. You wrote a 30 to $50 million check. You wrote a check into the Anthropic round—not the $4 billion round we did, but much earlier. You're doing fine.
Yeah, but he was an angel, not competing for rounds. What I'm saying is that the $30 million to $100 million funds, where they need to move $1 million, $2 million, or $3 million, are kind of a pain to fit into rounds. Anjan putting in $100,000 or $200,000 is sure in.
Yes. Your principle is right, but I'm just trying to think about counting. Think about conviction. How big was Sarah's fund? I want to say it was a $200 million fund, and she found a way to be in some of the most interesting companies out there. It can be done.
And then you've got Dave Tisch, who I think would be a really good example as well, with BoxGroup. It goes against the portfolio construction that all LPs love: high ownership and a concentrated portfolio.
There are always people who figure out how to play against the odds, right? But they are the best of the best, so you don't want to extrapolate.
In general, those are tough places to be unless you're exceptional. I was reading a tweet between Sarah and Patrick Grady, and Sarah was telling LPs, “My strategy is I'm just going to work harder.” That's probably the truth.
Everybody wants to have some magic strategy that nobody else is going to do. There's no magic strategy. Everybody in the venture industry is smart. You have to out-hustle and have grit to make it through, and Sarah definitely has that.
Final one before we do a quick-fire. We mentioned private equity being challenged in a lot of ways by a lot of AI companies. We're seeing the keys being handed back at companies like Medallia. You're seeing a lot of struggling companies in the books of these private equity providers. Is private equity structurally fucked?
Look, they're smart guys, and they know how to figure out and operate these companies. They also have majority control.
In some ways, the venture-backed companies—the SaaS companies where people paid high multiples—add tables and mirrors, and they got spooned, as I say. I think those are in a tougher situation.
Don't get me wrong; I think private equity is a challenge too. But the reason I say the venture-backed companies are in an even tougher situation is that, at least with private equity, you have a majority owner who controls the company and can do things.
You have a lot of zombie SaaS companies where nobody owns enough to be able to do anything. Nobody cares. How do you actually land that ship? At least with private equity, they can do something with it.
Landing that ship is going to be hard for everybody, but I think in that class of 2021 SaaS companies, the best outcome is getting spooned, which really means getting your capital back. The worst outcome is going to be zero.
Good old Bending Spoons. European. Just going to put it out there.
The quick-fire is a combination of mine and Joff's questions—he's on your team.
Joff. My partner.
Yeah, he came back with some bangers.
Why do you love pocket squares?
When I was growing up, I didn't care about how I dressed, and I didn't put any effort into it until I had this one conversation with my dad, when he said, “Listen, when you dress, you're not dressing for yourself; you're dressing for others. You're showing them that this is an important meeting, that you're expressing the importance of what you're doing to them.”
I know my partners make fun of this, but I dress up for partner meetings because it's a self-message to me that the people I'm meeting are very important, and what I'm going to do is important. I need to take that very seriously.
Now I feel guilty. Oh, Christ. Way to make me go. Yeah, Joff teed me up for that one, didn't he? I like that. It's really nice. I should probably think about that more.
You can invest in 1 seed fund and 1 growth fund that's not Menlo. Which funds do you invest in?
I have tremendous respect for the Bessemer folks. I was a co-founder with Byron, and I've known David Kahan. I think they are super disciplined. If I could invest outside of Menlo, I would invest in Bessemer.
That's for the growth fund.
Yeah.
What about the seed fund?
I'm looking for people who are going to be in interesting AI companies. There's this group of guys called E14 out of MIT, and I find them to be in interesting AI companies. They seem to really understand the MIT ecosystem.
Who, when you hear you're competing against them, are you like, “Oh, fuck”?
I think of more people than firms, but I would say Benchmark is super hard to beat.
Is Benchmark harder to beat than Sequoia?
I think so. Obviously, they're both great firms, but Benchmark is super hard to beat. Whatever they do—the combination of Eric, Chaitan, Avereh, and Jack—they are just a beast.
What would be your single biggest piece of advice to an LP allocating into venture at this time?
Look at the windshield, not the rear-view mirror. The results and financial performance are rear-view-mirror calculations, and they're good at telling you what they did in the past. They don't tell you how a firm is going to do.
Performance is a lagging indicator, and it's actually a 5- to 7-year lagging indicator. My advice would be to call a bunch of entrepreneurs from successful AI companies and ask them who the partners they respect are. My aim is they didn't take the money.
And if the firm you're talking to doesn't have a few of those partners in the mix, then that's your windshield.
How do you stop your team getting arrogant? You guys have got the winning hand.
You're only as good as your last investment. It doesn't matter if you're the lion or the antelope in the savanna. You wake up in the morning: if you're the lion and you don't run, you don't eat; if you're the antelope and you don't run, you don't live. You just have to run.
I feel like you have to think about the most important meeting being the next one. The most important investment is the next one. The most important board meeting is the next one. If you don't spend time in the present thinking about it, I think you lose in this game.
What's the secret to marriage when you scale wealth over time together?
Oh, wow. Well, you gotta marry someone better than you, which I did. Thank you. And you gotta convince her to stay with you—or him, whatever your preference might be. Finding a life partner who inspires you to be the best version of yourself and supports you in being that is, I think, critical.
If you can do that for each other, I think that'll work, because I think at the core of a long-term marriage is real respect. It's love and real respect, but I think respect is super important. That comes from inspiring each other to be the best version you can be.
What's the best advice you've ever been given? You mentioned Mr. Steve Sloan and his father-in-law. His father-in-law is one of my closest friends, and he once said to me, “You're never wrong to do the right thing, but the right thing is very often the hard thing.”
Yeah. I think the best advice I've gotten has really centered around being around people. I think Ronald Reagan has a quote that Tom Reilly, who's a CEO of Trigger, told me once: “There's no limit to what a person can do as long as they don't care who gets the credit.”
When I was early in my career, I was very focused on getting credit. I really thought, “Am I gonna get credit?” Then I let go of that and focused on just doing what's right and not worrying about whether I'm gonna get credit. That's actually been pretty freeing, and I think that's made me a better teammate.
I love that. I don't think there's a better way to end it than that. Your humility is astonishing. It's really just—one, you're very calming. I almost feel like you should be on Headspace or Calm. And two, it's a wonderful humility that I rarely see in a venture investor. But thank you so much for doing this, Venky.
You have too many successful people on your show. I'm trying to lower the bar for you.
I've so enjoyed this. Thank you for doing it. And you see with shows like this why it's so much better in person. You can't have this virtually, so thank you for doing it.
Thank you, Harry. I have to say, my colleague Claire was coming with me, and she said, “I watch Harry all the time. He has become my favorite show.” Especially the one you do with Rory and Jason. She said, “Oh, this has trumped the All-In podcast as my number one show.” So I have to say, you're getting fans all over the place.