The Twenty Minute VCDavid Tisch: Why No Manager Wants to Stay Small & Why Competing with Mega Platforms is a Losing Game
EVERY SPOKEN WORD
70 min read · 13,831 words- 0:00 – 1:25
Intro
- DTDavid Tisch
I've never understood trying to compete head-to-head against who I would deem to be the best VCs in the world. Every concentrated manager will say that we win 90% of the deals we wanna win, and I think that's total BS. I think it's, like, 20%.
- HSHarry Stebbings
Over the years, me and David Tisch have done many shows, and I've always questioned his model. Low ownership, very diverse portfolios. And do you know what? I was wrong. David has absolutely crushed it. He's one of the best early-stage investors of our time. This was a phenomenal discussion. I loved making this happen.
- DTDavid Tisch
I think the Lean Startup was a total fake. There's people to me right now, and this happens in hot market conditions, that are playing a short game. I believe the right to invest in subsequent rounds is earned. I work for our LPs, and my customers are founders. We don't allow grenades at early stage. You're not allowed to throw a grenade on someone else's deal.
- HSHarry Stebbings
Ready to go? [upbeat rock music] David, I'm so excited for this, dude. It's been two and a half years since you joined me. You very kindly reminded me of a debate that we had a couple of years ago, and we're gonna get into that. Um, but thank you so much for joining me first.
- DTDavid Tisch
Thanks for, uh, having me back. Nothing's happened in between the past two and a half years and now, so we can just sort of regurgitate all the old conversations.
- 1:25 – 2:49
Has Venture Capital Fundamentally Changed?
- HSHarry Stebbings
Has our job completely changed, David?
- DTDavid Tisch
In some ways, totally, and in other ways, not. I think, you know, I've been doing early-stage investing for 17 years now, uh, which makes me old. Um, and I think a lot of the times people try to relate the current moment to a historical moment. So, uh, you know, is this like 2021? To me, no. It has nothing to do with '21. It's a totally separate moment, and this one's funky and interesting and maybe frothy, maybe insane, whatever it is, but it's a standalone new market condition that you have to figure out in today's world. Because in '21, there were a bunch of other factors, macro, micro, that were creating that environment. And if you go back to, you know, '18 and, uh, '15 and 2010, each one of these moments are just different. And so I could argue our job has totally changed and equally explain that our job is just to do whatever the current market conditions present. Uh, and the actual job is, like, see, meet, get to know great founders, make a decision should we invest or not, and beg them to take your money. And that's the, the funnel
- 2:49 – 5:59
Why This Market Is Nothing Like 2021
- DTDavid Tisch
that we operate in.
- HSHarry Stebbings
In 2021, I think we can acknowledge it was just incredibly bubble-like. It was a good time to sell. It was a bad time to buy. There was no fundamental technology innovation. There was short-term behavioral change with COVID in different respects, communications, buying. Everyone says, "Well, now it's starting to feel like 2021." Are you in that camp of the craziness is real, or are you in the camp of, "No, we are so early, and there is so much room to run"?
- DTDavid Tisch
I don't think it's as simple as that. I think in each one of these moments, there are good companies and bad companies. And so as a VC generally, and especially as an early-stage VC, I think the macro is less impactful than the micro. Is the company that I am fortunate enough to be an investor in the good one? Is it the great one? Is it the, the most important one? That transcends the macro, and the macro to me is like a portfolio analysis. It's a industry analysis, but it doesn't come down to a specific company analysis. So do I think there are, you know, not perfect companies raising a lot of money at big valuations? Yeah. But I don't know that that's ever not the case, and I think you've seen it historically in our industry. There are incredibly public blowups of some of these companies that happen in, uh, catastrophically messy ways that sometimes create TV shows or movies or documentaries. Um, and then there's companies that die quietly in the night. Um, but I think underlying all of these moments of frothiness are probably a handful to a lot of great companies that are building, uh, high-quality businesses, and they're doing it in, you know, a, a long-term-oriented way. Are they raising money quicker? Are they raising money less dilutively? Are they, uh, you know, doing it at big valuations? Absolutely, but I don't think that that is a, like, industry-wide harmful, uh, set of conditions. It's just is this company a great company? Can this founder, can these founders navigate incredibly complex, uh, changing environments almost in real time today, um, to create an enormous amount of value that I think you are, to your point, in the early innings of a deployment of a horizontal new technology that will have tremendous impacts. But like all other technologies, what you see is this initial wave of impact, initial set of reactions, some version of plateauing, more innovation, plateau, innovation, plateau. The difference this time is those, like, cycles are, like, two to three months. It's the new model release. It's the new revenue growth of a vertical AI business. It's a huge M&A deal. All these moments create these mini cycles that feel like they have sort of waves across the industry.
- 5:59 – 7:11
Are $10–20M Seed Rounds the New Normal?
- HSHarry Stebbings
We've seen seed rounds be $10 to $20 million very consistently.
- DTDavid Tisch
Well, well also 50 or 100 or a billion.
- HSHarry Stebbings
Oh, for sure. But I'm saying kind of if, if we don't take the real outliers, like 10 to 20, it's really been quite normalized as a round size for good seed companies with, you know, pedigreed founders. I get that our job is just to find them and, and, you know, beg them to take our money. But does the business not really change in that respect? Suddenly, how do you think about sizing? You know, bluntly, that there's, there's nothing there and you're having to write a large proportion of your fund as an entry check. How do you think about that with the massive explosion of round size?
- DTDavid Tisch
You can either come on a podcast and complain about it, or you can do the thing, make a decision, yes or no. If you're going to play the game that's, that's in the market of deals, you don't get to change the competitive dynamics of a free market. So if great founders or potentially great founders are going to raise 10 to 20 because someone else is gonna do the deal at that price,
- 7:11 – 8:00
Why Bigger Outcomes Make Bigger Seed Rounds Rational
- DTDavid Tisch
you get to say yes or no. So I think if you think that is an important company and one that you wanna be part of, you have to say yes. And there's two conditions that allow for those starting points to not materially change the economics in venture if the outcome sizes are bigger. So if, you know, you, you think about 10 years ago, the idea of building a $10 billion company was far-fetched. Today, that is sort of like you have to sit and look at an early-stage company and try to squint and get there as a sort of normal outcome, um, versus a billion. So I think there's a change factor there, and then you see anomalies well past that in terms of valuation or even acquisition, um, or,
- 8:00 – 10:21
Why Lower Dilution Changes Venture Fund Math
- DTDavid Tisch
or our future IPOs. And then the second one is the lack of dilution. Um, so as an early-stage investor, to me, in the companies that tend to hockey stick very quickly, the Series B, C, D are dramatically less dilutive to the founders and the early cap table than in, in the past. They are raising these later-stage rounds at 3 to 8% dilution instead of 12 to 20%. And if you take that across multiple rounds, your early-stage investment just gets diluted less, and that is an economic factor. Now, we, BoxGroup, we invest in a, a wider set of companies, which you've criticized before many times for not an ownership focus. If our entire portfolio is filled with $20 million seeds at, you know, 200 million pre, do I think that the m- the business is fundamentally changed? Yes. And so you have to find in this market of, you know, a, a, in this market of varied entry points for early-stage investing, I think you have to have a portfolio balance, but not on an individual deal basis.
- HSHarry Stebbings
Totally get that in terms of portfolio balance, kind of on a blending entry price and making it a little bit more palatable. You said there about my criticizing your portfolio.
- DTDavid Tisch
I mean, uh, speaking about it. I didn't use the word criticize on purpose.
- HSHarry Stebbings
No, dude, I... Trust me, I, I, I think one of the most important things to look for in, in anyone, actually personal or professional, is like someone who's willing to, like, admit that they were wrong. Um, I have no problem admitting that I was wrong, and what I was wrong on very specifically, I think, is, like, not seeing outcome size expansion in the way that we have done, and that's very rigid-minded of me, which is my fault. But it's enabled incredible returns from companies with smaller checks and not having ownership, so to speak. Um, what, what... How would you characterize what I got wrong? Did I do a good job of it there? Like, you can own me for it. I'm very-
- DTDavid Tisch
I, I want, like, a soundtrack as you're doing that-
- HSHarry Stebbings
[laughs]
- DTDavid Tisch
... so if we could add post-production music in-
- HSHarry Stebbings
Oh, yeah, we will. It's like admit, admit
- DTDavid Tisch
... I think it will, it'll go a little-
- HSHarry Stebbings
Yeah, yeah
- DTDavid Tisch
... it'll go a little wider on the, on the, you know, themes.
- HSHarry Stebbings
It's kind of like Lose... You know Lose Yourself?
- DTDavid Tisch
Yeah.
- HSHarry Stebbings
The first kind of-
- 10:21 – 11:48
Why Ownership Matters Less Than Getting Into the Outlier
- DTDavid Tisch
Yeah
- HSHarry Stebbings
... 30 seconds beat.
- DTDavid Tisch
Yeah.
- HSHarry Stebbings
Yeah. We'll, we'll get-
- DTDavid Tisch
Just like a little background music.
- HSHarry Stebbings
Yeah. [laughs]
- DTDavid Tisch
Harry getting deep.
- HSHarry Stebbings
[laughs]
- DTDavid Tisch
Uh, no, I, I think, I think that I've always believed that ventures is a pure power law dynamic industry. You have to be in the outliers. And the idea that me or you, to pick on both of us, are going to be able to find and buy 10 to 20% of a true outlier in the seed round and beat the rest of the market, which I truly think, you know, a lot of, not all, are great at their jobs. You're gonna fight them head-to-head and convince the founder to pick you, and that's the company that matters. I think it's a lot of steps that you have to believe to get that business right. And so I've never understood trying to compete head-to-head against who I would deem to be the best VCs, uh, in the world. And I think these are brands and these are people that have spent decades building, um, you know, w- what their organization stands for and attracting the best set of founders to want them, uh, in their deal. And I think those multi-stage firms that have, uh, been around for a long time are really, really good at seed investing. And so-
- HSHarry Stebbings
In a way that they weren't before,
- 11:48 – 14:13
Why Multi-Stage Firms Have Become So Powerful at Seed
- HSHarry Stebbings
huh? Like, I feel like they-
- DTDavid Tisch
They're more con- They're more con- they're more concentrated focused on it.
- HSHarry Stebbings
Yeah.
- DTDavid Tisch
Um, and they're more accessible and they're more efficient, and the market's more efficient. I think founders know how to reach them and know how to run a process very differently than in the past. So I think post-COVID, there's a tremendous efficiency in the fundraising market. Um, competitive deals It used to be three to five term sheets in an early-stage round can these days be 10 to 15, or it's purposely only three to five, but those three to five are really competing, uh, against each other. And I think that is, again, something you can complain about or just accept the market conditions. And so for us, the belief has always been we have to be able to invest in the people that we meet that we think are the best, and we can't let our business get in the way of it. And so to me, the thing that you got wrong is, is two pieces. One is the math. Our business math on our side as a venture manager that has LPs, that needs to return our capital to LPs at a outlier, uh, way, I think you didn't do the math right, and I think a lot of people don't appreciate that our business makes sense. And that's okay. We like what we do. We think it's really interesting.
- HSHarry Stebbings
And I specifically didn't do the math right because I didn't see the outcome size expanding. Is that, is that it? You've got the numbers.
- DTDavid Tisch
Well, the second part is, yeah, I, maybe that's it, or maybe the lack of dilution part that I made, uh, before is, is what you get at the beginning actually stays pretty consistent, whereas I think in the past you would probably put a, like a negative 80% on that number.
- HSHarry Stebbings
Well, with Jason Lemkin, who I do a lot of shows with every week, we do the weekly show, a- and he's like, "100%, 60% you'll be diluted." I- is that not true in your knowing the numbers?
- DTDavid Tisch
I don't think in the best companies.
- HSHarry Stebbings
Mm.
- DTDavid Tisch
Now, like not every company goes up and to the right and never sort of runs into bumps. I think the macro when you get big can cause some bumps in valuation. You're seeing it right now in some of the biggest labs going out and trying to raise rounds and sort of re- uh, reevaluating the, the price that they're raising at. Um, if you go back in history, like Uber, Facebook, um, [lips smack] Airbnb, uh, Ramp, which I think is one of the best modern
- 14:13 – 16:28
Why Concentrated Seed Funds Overstate Their Win Rates
- DTDavid Tisch
companies ever, uh, they've all had a bump, a down round. And so I don't think it's always just up and to the right, but I think in this specific sort of three-year window, there is a lot of continued momentum in terms of valuations. Um, but the second piece, which I think is related to the first piece, that I th- I think concentrated funds dismiss, is there is an adverse selection in the concentrated model of what gets in versus what you want to get in, [lips smack] meaning every concentrated manager will say that, "We win 90% of the deals we wanna win," and I think that's total BS. I think it's, like, 20%. And so in a given fund cycle, if you're funding 30 companies that you have this immense conviction in, concentration of 30 names with 10%, n- you need, obviously you need because it's vital, need 10% of the company in order to make the deal work. I think you actually offer that deal to upwards of 120, maybe 150 companies to get your 30, and I don't think people admit that. So I do believe that the best companies, the ones you're most excited about, don't always make it into the portfolio. And so just because you have 30 that you own 10% of, it doesn't mean those are the 30 that you would've liked to be in that portfolio. I think in our model, what we're able to do is get into more of the companies that we're excited about than other people.
- HSHarry Stebbings
I get that, and you know what worries me though so much, and I am asking here, but it worries me is I, I completely agree with you in terms of that supposed win rate. And what happens now though is they just say, "David, okay, fuck it, I lost to Sequoia and BoxGroup. [sighs] Let's do another round. I'll, I'll do it at 800. I know David just did the first tranche at 400, but I'll do it at 800 today." And for the founder it's like, "Well, good deal. Like, nothing's changed in the company. I get more money at double the price." [laughs] I think it distorts companies and really entirely-
- DTDavid Tisch
What are you worried about?
- HSHarry Stebbings
I'm worried about founders losing focus and becoming distracted with way too much money
- 16:28 – 17:15
Does Too Much Capital Too Early Hurt Founders?
- HSHarry Stebbings
way too quickly.
- DTDavid Tisch
That is, like, a babysitting problem. Sometimes that's gonna happen, for sure. But to attribute that fear to every founder, some founders are gonna tremendously benefit from having more runway, higher valuation, more momentum, more buzz in order to recruit people, in order to show that there are believers that think this can be huge so that they can justify to customers to get early partners. If you are a great founder, and it doesn't mean all of them are going to do it properly, you have to take all the conditions that you've chosen to take on, so if you took on two tranches, if you took on high valuations, if you took on a lot of money, you're gonna have to use those variables and execute your company building in a different way than if you're
- 17:15 – 19:19
Why David Thinks the Lean Startup Was “Total Fake”
- DTDavid Tisch
super capital constrained. I think The Lean Startup was a total fake. It was a, like, stupid, m- like, brainwash that happened for 10 years with, like, professors and books and tweets and blog posts that was just, like, totally awful. Um, and I think it sent people, like, the wrong message. Like-
- HSHarry Stebbings
Why, why was it totally awful, just because?
- DTDavid Tisch
Because name a company that actually ran the lean startup playbook that worked. One. Every company, if you're going to be actually successful, needs a lot of money, especially today.
- HSHarry Stebbings
But, like, 37signals is, is one that's not taken much-
- DTDavid Tisch
Yeah, some bootstrap companies, but if you, if you wanna get on the venture flywheel, lean is not the answer. Like, inevitably you're gonna be fat. You're not gonna be lean. You have to be. It doesn't mean undisciplined, right? What, what ... The, the difference between the word, like, lean and the word well-funded is not lack of discipline. It c- it, it's just not- Automatically attributable. Does that mean that every company that raises a ton of money is gonna be well-disciplined? No. There's gonna be, again, back to where we started, bad companies.
- HSHarry Stebbings
Well, you do tranche rounds. If-
- DTDavid Tisch
Yeah
- HSHarry Stebbings
... a founder says, so you're investing-
- DTDavid Tisch
I don't like them. It d- but, like, again, there's the, like, emotional reaction and the business decision, and those are very decoupled.
- HSHarry Stebbings
But, but you will do the second or third tranche?
- DTDavid Tisch
Don't put this on a- I don't want founders to know that we'll just rip checks into tranche rounds, but yeah.
- HSHarry Stebbings
Whenever... Like, I, I, I, I won't. I'm-
- DTDavid Tisch
I don't want to. I would like to invest at this, at the lower price.
- HSHarry Stebbings
I'm too... I, I'm fu- fuck off. This is a partnership.
- DTDavid Tisch
I get it, but that's your problem. Get a shrink.
- HSHarry Stebbings
I don't need a fucking shrink. This is a partnership, and you're saying you're inherently less valuable than them. Well, fine, just don't take me then.
- DTDavid Tisch
Okay. That's their choice. And, and guess what? They're not gonna take you, and you can go back, and you can choose that company is not gonna be... That's a yes/no decision. That's it. And so as a-
- HSHarry Stebbings
But you're happy then to
- 19:19 – 22:03
Why Founders Have All the Leverage in Today’s Market
- HSHarry Stebbings
just t- to take that?
- DTDavid Tisch
I didn't say happy. That's now an emotional attribute. But like-
- HSHarry Stebbings
But you will take it.
- DTDavid Tisch
[laughs] I will, I will be sad and take it. That's a-
- HSHarry Stebbings
[laughs]
- DTDavid Tisch
That's, like, a different thing. You will-
- HSHarry Stebbings
I will be sad
- DTDavid Tisch
... you will succumb-
- HSHarry Stebbings
And take it.
- DTDavid Tisch
Yeah. You will, you will just admit that this is sad and fall in line. I think it's our responsibility to earn the right to do what we want to do versus what a founder is offering us. And so again, beg. Y- you can beg to have a entrepreneur do what you're asking them to do. So if, if there's two tranches, I would like to enter in the lower tranche. I need to convince the founder to allow me to do that. And if I don't, it's a me problem.
- HSHarry Stebbings
I would like the lower tranche, please. [laughs]
- DTDavid Tisch
Yeah. Yeah.
- HSHarry Stebbings
Cake or-
- DTDavid Tisch
You have to ask for it
- HSHarry Stebbings
... cake or death. Cake, please. [laughs]
- DTDavid Tisch
Yeah. And then, and then they say, "No." And then you're like, "Pretty please." And then they say no again, and then you have to, like, beg differently.
- HSHarry Stebbings
Come on, please. I'm just a little-
- DTDavid Tisch
Yeah
- HSHarry Stebbings
... seed fund. Come on.
- DTDavid Tisch
Right. You have to use all your little sale tactics, and then you get rejected, but, like, is that an enjoyable market condition that's been emerging more and more in the past couple years? No. Do I... Like, if, if I am sitting there, and I view it as, like, not the founder that tranched us but the other VC, it's good to know, right? I also have a long memory.
- HSHarry Stebbings
Ooh, ooh, scathing. Ooh.
- DTDavid Tisch
But it is, right? Like, you have decided that I will pay another price, not the founder. You've created the structure of this deal such that I am not sitting on the cap table with you. I am pushed to a, a different product than you get to invest in. That means when we have early stage investments and are going out to market to help them raise capital, if I get to be a voice in the ear of a founder, I have opinions too.
- HSHarry Stebbings
Remember, I was on your side, David. It was-
- DTDavid Tisch
No, you weren't
- HSHarry Stebbings
... I was always on your side. I was on your side. Come on. [laughs] I was-
- DTDavid Tisch
But, but I mean it, right? Like, there's people to me right now, and this happens in, in hot market conditions, that are playing a short game, and there's people that play a long game. And I think one of the-
- HSHarry Stebbings
And sorry, just they're playing a short game because they're cutting people out, they're pushing them into second tranches?
- DTDavid Tisch
Yeah.
- HSHarry Stebbings
Yeah.
- DTDavid Tisch
It's like I just think, like, there, there's a set of relationships that you build in this business because we're all dependent upon each other in very different ways that ebb and flow in different times, in different conditions, in different companies, that if you're in the business of maintaining and building long-term relationships, you're gonna choose certain behaviors over others
- 22:03 – 23:55
How BoxGroup Invests Without Ownership Requirements
- DTDavid Tisch
in different moments. And the thing that we've done at BoxGroup that I think is different than a lot of other firms as they've built is we've stayed very true to who we are. We do early stage investing. We try to be there on day one. We don't take our problems and put them in front of founders. We try to be as helpful as we can be, and we try to be founder-friendly in every step of the way. Does that work perfectly every time? No, but that's the intention. So we write, we write checks that are not needing of ownership. We don't sit on boards. We don't write competitive term sheets. We are happy to lead a deal. We are happy to help a founder get in business with some money. We're happy to be totally creative in how we invest, but it's oriented around early stage and getting in at that dream level.
- HSHarry Stebbings
What is the average ownership?
- DTDavid Tisch
I don't know. I have to... That's a math question.
- HSHarry Stebbings
But, like, is it, uh, like, genuinely, is it, like, 5%, 2%?
- DTDavid Tisch
There are deals we do where we own, at the initial, uh, check, 1%. There's deals we do at 10% and everything in between.
- HSHarry Stebbings
But there's no too low?
- DTDavid Tisch
Again, that's an emotional thing, not a business thing. I, I'm sad if we have to write a really small check, but, uh, it comes down to, like, yes or no. When does that happen the most frequently? When we get to a deal late. When you, when you meet a founder, and the deal's in process, you're now begging for scraps, as you should, and that's a, that's our fault for getting to something late. And that's something we can do better as a firm, is meet founders earlier in their journey. And if we didn't do it, we need to figure out internally, like, what could we have done better to meet a founder before there was a company?
- HSHarry Stebbings
Can I ask you, what is your
- 23:55 – 26:06
Why Getting to Deals Late Is the Biggest Reason VCs Lose
- HSHarry Stebbings
win rate?
- DTDavid Tisch
So different market conditions, it ebbs and flows probably between, um, 70 and 90%. And I think the single factor that causes us to lose the most is getting to something too late. Like, speed of our decision-making and accessing the opportunity are the two factors that we control that hurt us the most. There's a subset of companies that just meet us and don't want us- But that's harder to, to course-correct because you almost don't know why they didn't like you. Uh, it, it's like a, I don't know, an, an EQ emotional outcome, or they didn't think you were valuable enough, or, uh, maybe they referenced you and they, they got something that said, like, not as good as you need them to be. I think we care a lot about those situations, but I think that happens sometimes. The ones that I think we organizationally, uh, can, can work on is how do we get to everything, uh, before everybody else? And I think that's the obsession. We're, um, a team of 10 investors. There are six, uh, partners at the firm. We've all worked together for a long time. We all like each other, and we all do the work. Like, our job every day is to wake up and meet the next founder that we're excited to back.
- HSHarry Stebbings
I think both of us having flexibility to not have to be lead. Like, you know, uh, I think, again, I, I admitted my wrongdoing. Like, I, I turned down, um, great businesses, um, over time because of ownership, and it was just terrible decisions. And so now we invest very differently. You know, we will absolutely do the 1 or 2% if we think it's an unbelievable founder and it's an amazing opportunity. So great. That means I, I never lose because I will just do a smaller check. Um, or not never, but you know what I mean. Rarely lose 'cause we-
- DTDavid Tisch
Yeah
- HSHarry Stebbings
But if I had to only lead, that would come down dramatically.
- DTDavid Tisch
Totally.
- HSHarry Stebbings
And so my question to you is [laughs] do the pure-play lead-only seed funds still have a business
- 26:06 – 28:54
Are Lead-Only Seed Funds Becoming Obsolete?
- HSHarry Stebbings
in a world where-
- DTDavid Tisch
What are the pure-play lead-only seed funds left?
- HSHarry Stebbings
I mean, I think you've got your, like, Uncorks, your Floodgates, your, uh... I mean, Susur, no. First Round?
- DTDavid Tisch
I think they've moved into a different style of investing and more flexible and play it a little bit later when necessary on pur- on, on, like, strategic purpose.
- HSHarry Stebbings
So what you're saying is that business doesn't exist anymore.
- DTDavid Tisch
I don't wanna be in that business.
- HSHarry Stebbings
And why, why is that?
- DTDavid Tisch
'Cause I don't think you can compete against the greatest firms in the world who are running that strategy as part of what they do.
- HSHarry Stebbings
With much less price sensitivity and much bigger checkbooks.
- DTDavid Tisch
Yeah, I don't even think that's a factor. They're great at what they do. I like very much Pedestal.
- HSHarry Stebbings
I, I, I do think it is a factor.
- DTDavid Tisch
The best firms-
- HSHarry Stebbings
We, we, we have, we have lost to, like, a GC of the world, and with respect, a junior there, and I don't mean that disparagingly, but someone who is more junior because they offer treble the price and treble the check. I, I agree with the founder for taking it. Like, [laughs] wholly within your right to do it, but that's why.
- DTDavid Tisch
Yeah, but I... Like, it's an offer in the market, a free market, and I think they take the majority of the air out of the room if you're trying to compete for, uh, you know, I'm gonna lead, sit on your board or not sit on your board, but I need 10 to 15% of your, uh, seed company. I just think there's a greater efficiency to access the multi-stage firms, and the multi-stage firms are happy, uh, to do those deals. I also think, like, what you've seen happen is it used to be a lot of firms would be like, "Okay, I'm not gonna do this. I wanna wait to see this at the A," or, "I'm not gonna do this at the A. I wanna wait to see this at the B." And what's happened is they don't get to see it. Like, that might've been your only shot to do the deal because there's an efficiency in the market, and there's other people that also [laughs] wanna do it at the B. And you might lose there, and you might lose at the C. And so what you're seeing is if Sequoia wins, it might mean that, um, you know, Andreessen or, uh, Kleiner or someone else needs to immediately come into the next round because they know that that's the best probability they have of getting a real check into that company, and they do it quickly, and they do it aggressively. And I think that if you lose head-to-head in a seed, in an A, in a B, you can either sort of put your tail between your legs and call it a day, or you can try to figure out a new entry point with minimal progress and minimal, uh, developments to get your check into that company if you believe that was an important
- 28:54 – 32:27
Why Pure-Play Seed Is One of the Hardest Venture Strategies Today
- DTDavid Tisch
one.
- HSHarry Stebbings
I think it's an amazing point that there was a willingness to wait before that's now gone. I, I think that's absolutely right and very pertinent. Can I ask you though, I speak to so many LPs, um, as we said, they love to talk. Uh, and every LP wants one category of venture. We want the pure-play seed investor in Silicon Valley, small fund, under 100 million, pure-play seed. And I go, "That is the single worst fucking segment to be in. Like, that's the one segment you don't wanna be in." And they all kind of look at me rather horrified. What advice would you give an LP when they look at the segments today and go, "Ah, I want pure-play seed in San Francisco as my bucket"?
- DTDavid Tisch
I think there are three different stakeholders in our industry, and their incentives and m- and current conditions are very decoupled for, you know, probably the, the, the most frustrated each... Like, like, we're in a founder world. I think GPs are struggling to have a very static and focused strategy because of we're in a founder-friendly world, and I think LPs are frustrated because they want certain versions of exposure or, uh, portfolio construction that basically aren't available. I don't think there's an easy solve for the LP problems, and I don't think there's a clean way to operate as a GP in a ever-changing market that is very complicated right now. And so I think founders get The leverage, they get to raise capital from people they like at prices that they like. And, uh, you as a GP can say yes or no. And on the LP side, they're gonna look at your portfolio construction, your entry point, your ownership. And then a lot of the multi-stage funds have multiple products that LPs, uh, will tell you and me that they don't like to do, but yet it's gonna be the majority of their allocation into ventures going to go to the multi-stage firms that are established, that, uh, are a way to get scaled capital into the industry. And frankly, like, exposure to some of the best companies in the industry through that. So your question is around, like, the LP conditions. I believe my relationship with our partners, uh, is one of truth. Um, we invest out of a $275 million seed fund right now. It will invest in around 150 companies. So we are pure play seed with lack of a focus on ownership and concentration. There is a large cohort of LPs that are confused by our math and don't th- doesn't think it works, and that don't believe in our model.
- HSHarry Stebbings
You do 50 companies a year.
- DTDavid Tisch
A little more probably.
- HSHarry Stebbings
David, do you remember them all?
- DTDavid Tisch
Yeah. I don't know what the other people who do one to two deals a year do all day. That-
- HSHarry Stebbings
Podcast
- DTDavid Tisch
... that also confuses me.
- HSHarry Stebbings
Podcast too. [laughs]
- DTDavid Tisch
Yeah. Uh, like, it sounds, sounds lovely. Um, there are LPs who don't believe in our math. Our math works. Like, I know our math works. I see our math, and I think our, our partners also believe our math works, and that's awesome. Uh, because our, our model's terrible if the math doesn't work.
- HSHarry Stebbings
From a liquid returns basis, what has been the single best investment?
- 32:27 – 33:30
How Cursor Returned the Fund Multiple Times
- DTDavid Tisch
Um, we were fortunate enough to have met Cursor, uh, sort of before, uh, they were working on, uh, the, uh, business that scaled. And, um, my partner, uh, Claire, got to know Michael when they were, uh, investing on Dorm Room Fund together. Uh, and we, uh, were in the earliest round of Cursor, um, which-
- HSHarry Stebbings
Did that return the fund?
- DTDavid Tisch
Yes.
- HSHarry Stebbings
Multiple times.
- DTDavid Tisch
Multiple times. Yeah.
- HSHarry Stebbings
I told you this model doesn't work, David.
- DTDavid Tisch
I know.
- HSHarry Stebbings
But you didn't, you didn't listen. You know-
- DTDavid Tisch
I know. I gotta, I gotta do better math
- HSHarry Stebbings
... you, you, you were stubborn
- DTDavid Tisch
Or our Excel sheet broke. I tried to update it one day and-
- HSHarry Stebbings
Do, do you know what's astonishing with that? And I'm really pleased you chose that actually as an example, which is the speed to that enterprise value. So, at four years. I thought, thought every LP was moaning that venture's taking too long. Now we're seeing OpenRoader. Was OpenRoader one of yours?
- DTDavid Tisch
It was not.
- HSHarry Stebbings
Oh, bugger. It wasn't one of mine either.
- DTDavid Tisch
I know. Next time.
- HSHarry Stebbings
Yeah, next time. Um, but, like, you know, this was, whatever, two, two years
- 33:30 – 35:21
Why Company Creation Is Moving Faster Than Ever
- HSHarry Stebbings
to $8 billion?
- DTDavid Tisch
I think the speed of company creation growth explosion, uh, is different. And I also think underlying... Like, blessed to have been in, in early part of the Cursor, uh, story. And I think, you know, what they did and accomplished is, uh, truly sensational and, uh, it's a, it's a generational outcome. It's the biggest venture M&A deal in history. We were just lucky to have, have been there early. I think underlying, like, in the fund that Cursor sits in, in the early-stage fund that Cursor sits in, for me, what I love is there's 10 other companies that are fascinating. And they're just taking a slightly more reasonable timeline to grow and compound. Do I think any of them, like, will get to the accomplishment of, of how big and great Cursor was? I don't know. And that's not, like, a binary they did, they did it or didn't. But I think what, uh, you have to appreciate in this early-stage investing is it, things take time. We were the earliest investor in a company called Clay. Clay is a bumpy four-year road to explosive growth, and now is growing and compounding what they're doing in an amazing way. But it's not a clean, perfect story. And I think it takes learning and it takes iteration and developing their go-to-market that got them to where they are at today. Baseten, we're, we're in the seed round of Baseten. You needed inference to sort of become a space. And Baseten today is a full outlier company, and they're running at full speed and, and sort of hitting that hockey stick, uh, fully. Uh, but it wasn't this just
- 35:21 – 39:00
Are the Best Companies Obvious From Day One?
- DTDavid Tisch
start up and to the right.
- HSHarry Stebbings
Do you think the best companies are generally immediately obvious? Or do you think actually the value is generally actually in the messy middle and the ones you don't expect?
- DTDavid Tisch
I think there are signs early on that a founder, uh, is running the experiment at a world-class level. Um, and that is either they are hiring total outlier people to join them quickly. They are finding customers that are inaccessible early. Uh, and you're almost confused as to how they're getting so far ahead so quickly, and it's, a lot of the time, some combination of the product and the go-to-market conversations that they're having, um, or they pick the right idea. But I think there are always challenges and bumps, and sometimes those are prolonged and sometimes those are immediate. And so what you're really, uh, identifying is, can this founding team navigate? Again, like, I think the market is so complicated today. I, I, we, we spend time and we ask young people, uh, we go to college campuses a lot. We were up, uh, at, at Harvard and MIT recently, uh, and talking to undergrads. And I asked, like- Raise your hand if you have a vision for what the world is in 10 years. Which is our job, and which if you go back in time, young people, old people, there was, like, "I can see what the world's like in 10 years," or, or some guess of it. No hands went up. And I'm like, "Five years?" One hand. "Two years?" That's when you started to get some hands. And I think that's what people are feeling today, is uncertainty as to the timelines of what the future looks like. And when you're in this moment of AI and you have people saying we're all about to die from AI, and you have other people saying we're entering an age of abundance and free-flowing markets, uh, that will change the way labor forces work. Like, that's a pretty wide gap between the prediction of the future. And then you have the models rolling out frequently with major innovations that in some way are important to a subset of companies. But in the end, not every company's gonna need the cutting edge, bleeding edge model, and so you're watching this age of AI deployment, AI adoption, and it's gonna impact people differently at different speeds. So it's complicated. And then you're seeing AI impact the physical world, science, all these spaces that felt hard to access before that are getting opened up because of this horizontal technology shift. So there's just a ton of uncertainty. I think you feel it in the public markets, you see it with compute access, compute pricing, energy, data centers, the politics around all of it. This is complicated. And so when you're asked to predict the future, I don't know that anybody sits here today and actually has an answer. And it's cool that people come on podcasts or tweet or do whatever they do and say, like, "I know where the world's going," and you're like, "No, you don't." So I think what you're looking for in today's founders are people that are capable of real time navigating ever-changing conditions that are insanely fast and insanely complicated. And so to your question of, like, do you fund somebody and know it immediately? No, because I think the world's changing too quickly today for that to be
- 39:00 – 41:53
Why Today’s Winning Founders Are More Technical—and Better
- DTDavid Tisch
a condition.
- HSHarry Stebbings
Do you think the founders that succeed today are different to those in the past? Yeah, if I look at the founders, so, I mean, so they're inherently a lot more technical. There's a lot fewer, uh, sales-led founders today than there are-
- DTDavid Tisch
You're in a moment of that, right? And so the question to me is, like, if you're an early-stage investor, is there two years out when actually sales matter again in some way and go to market becomes a differentiator? And if that's the answer, you should fund those people today because their exposure to the bigger markets is not gonna be as purely relevant for, like, one to four years when their company is a bit further along, their product's ready. And so if that is your bet, it actually makes sense to start rotating a little differently today than sort of... You, you can't as an early-stage investor solve an immediate opportunity or need. Nothing goes fast enough. And so, um, but I do. I think the founders today are more technical in, you know, a non-offensive way, smarter than ever before. I think there's, like, less opportunity for mediocrity to succeed. And you can't just, like, identify a gap in a business market and go attack it with, like, laissez-faire approaches. You have to be so good in order to win right now. And, you know, you saw, I don't know if you saw the Scott Wu video that went viral where he's doing counting a c- You're like, "I can't compete with that. I can't compete with that," right?
- HSHarry Stebbings
I saw a great one which is cognition is just a wrapper around Scott Wu. [laughs]
- DTDavid Tisch
But, but you have to, if you look at every company right now that to me is, is becoming an outlier, the founder quality of each of them is really, really impressive. And I think that that, like, there was an era where, like, everybody was told you should start a company. Everybody should start a company. And I don't think we're there anymore. I think it's, i- like, can everybody start a business? Sure. And I think that's okay. And I think the word company and business are in some way different. And venture capital for probably 10 years was funding a lot of categories that were not capable of becoming as big as maybe you thought at the beginning because what they were aiming for was, uh, a bit smaller. I think today the appetite for scale from the venture product, um, is uncompromisable because you need to get, uh, huge to make the math work. And I think the founders' ambitions today are, like, A, huge, and B, the opportunity set feels
- 41:53 – 44:00
Why BoxGroup Stopped Investing in Consumer Brands at Seed
- DTDavid Tisch
unlimited.
- HSHarry Stebbings
I don't want to, like, single out a com- but it's a, a company that we both know and everyone will know, which is testament to its success. But, like, would you fund, like, a Harry's today?
- DTDavid Tisch
I think Jeff and Andy from Harry's are, like, world-class founders that if you put inside of any company, uh, they would build something of importance and of meaning. We at Box Group have stopped funding brands, not because I actually think they're small. I don't think you can fund brands at Seed. Because brands to me are built off of your initial data set of, like, does the brand resonate? Does the product resonate? Do people buy it? Do you have, like, customer LTV or CAC to LTV ratios that make sense? And you don't get any of that data at Seed. I think one of, like, the more interesting investor products out there is, like, doing brand investing at Series A. I don't think it fits in your traditional venture firms today, but I think there's a subset of investors that fund brands. If you look at the beverage industry as a great example, if you look at some of the QSRs, um, if you look at, you know, uh, personal care, there are scaling brands that are fascinating businesses. I just don't think where we sit today, we're equipped to invest pre-momentum.
- HSHarry Stebbings
Can I ask one thing that I see? You said it's very much a founder's market earlier. They can choose the price they want with the people they want.
- DTDavid Tisch
Yes.
- HSHarry Stebbings
Um, uh, to me it's like a real haves and have-nots.
- DTDavid Tisch
Yes.
- HSHarry Stebbings
Which is like there are three categories where if you're in that category, how 50 friends-
- DTDavid Tisch
There are three categories of haves and have-nots? That's ... You only named two.
- HSHarry Stebbings
No, three categories of interesting company that a- investors just go nuts for. And then obviously it's more than three, but a small number. And if you're not in that, even if you are in AI for X, investors are like, "Nah, not interesting. Not in compute, not in inference. Nah, not in data centers, not in chips," whatever, and you're instantly dismissed. Do
- 44:00 – 48:24
How Rogo Went From 39 Passes to a Consensus AI Winner
- HSHarry Stebbings
you see that too?
- DTDavid Tisch
But I, again, come back to founder quality and founder ambition and execution. So we were, uh, in the earliest round of a company called Rogo. They were building AI for finance. Um, Gabe, uh, finally told this story, uh, but after the seed round, I helped him go out to try to raise an A. Uh, I put my name behind this company fully, and I'm like, "Rogo is going after something huge, and Gabe is sensational." And I sent it out to, make up a number, he said 40, we can say 40. 40 Series A lead investors. He got fully passed on by 39 of them.
- HSHarry Stebbings
Did Keith do that round?
- DTDavid Tisch
Keith did that round. So 39 nos. This is now a consensus company. It has now been funded by, uh, Keith led the A, Sequoia, Sequoia did it, Kleiner did it.
- HSHarry Stebbings
Do you doubt yourself-
- DTDavid Tisch
Yeah
- HSHarry Stebbings
... in that app? You do, or you just think, "God, the mimicry of this market's ridiculous"?
- DTDavid Tisch
Both. Well, I just get sad. I'm like, "I'm ... I, I've, like, done this a long time. I'm, like, telling you to spend time here" And some of the passes were quick, of like, "We don't think this is interesting," or like, "We don't know that this could get big," or, "They don't have enough traction," whatever they were. But I just think there are companies in this moment of your, your point of, like, king-making haves, have-nots that are misread at different stages and then become one of the other categories. And so that to me means, uh, as, as it should be, early stage is not a perfect market, and there's not perfect information. There are gonna be companies that are not in the zeitgeist, off the radar, that compound value, compound momentum, and build something that's very important before, uh, or, or outside of the immediacy of, of those funding conditions. And I think Rogo to me was, like, totally misinterpreted by a series of investors at a specific point in time, kept building, kept getting better, and then I think in the right way, uh, rewarded for, um, you know, the, the execution of what they've done.
- HSHarry Stebbings
And you do follow-on checks into just the next round, next two rounds?
- DTDavid Tisch
No, so we, we operate today two funds. Uh, they're both $275 million. Uh, so it's a core seed fund. Uh, and then we do a follow-on fund. Um, we write sort of 20 to 30, uh, lean-in checks, uh, into companies almost all from our portfolio.
- HSHarry Stebbings
And the lean-in checks are 5 million bucks, give or take.
- DTDavid Tisch
5 to 30.
- HSHarry Stebbings
And that's across the A and the B, the next couple of rounds?
- DTDavid Tisch
Yeah.
- HSHarry Stebbings
What's the most you've ever invested in a company across the two?
- DTDavid Tisch
Probably $40 million.
- HSHarry Stebbings
Which company was that?
- DTDavid Tisch
I mean, we've, we've written substantial checks into Ramp, into Clay, into Baseten, into Rogo, into Tandem, um, into-
- HSHarry Stebbings
Which did you not, and on reflection, what did you not see?
- DTDavid Tisch
Oh, we don't, uh ... Which did we not write a big check into? Um-
- HSHarry Stebbings
Yeah, like you did a first check.
- DTDavid Tisch
Well, sometimes you can't, sometimes you can't get more than your pro rata in companies, and that's a fight for allocation in future rounds, and that might be the founder choosing not to take a bigger check from you. Um, so that's one condition. And then the other condition is, like, we mis- we misread, uh, the company and didn't lean in hard enough when we, uh, could have. And I think we're not a perfect ... We don't make perfect decisions. I wish we did. Uh, so I look back and there are so many opportunities of great companies that we were fortunate enough to be early in that we, uh, were too slow to react to. Um, and, uh, I think-
- HSHarry Stebbings
Is there, is there one that you think of first there, and what did you not see?
- DTDavid Tisch
I think of a lot, but I, uh, I think we're, like, incredibly fortunate to be in business with that founder at the earliest stage. And, um, I think our job is to, like, continue to help them in the ways that they ask us to help them and, uh, make our customers,
- 48:24 – 52:30
Are Pro Rata Rights Actually Worth Anything?
- DTDavid Tisch
who are the founders, happy.
- HSHarry Stebbings
David, is pro rata a right? We saw this-
- DTDavid Tisch
No.
- HSHarry Stebbings
Is it-
- DTDavid Tisch
No. Like, do I think, do I think a bunch of the VCs that are, the early-stage VCs that are out there saying, like, "We don't need pro rata. We're gonna, like, give it up"? Like, it's all marketing garbage. It's just nonsense. Like, I can write a blog post too. I just don't believe that that, it's that black and white. I believe the right to invest in subsequent rounds- Is earned. So whether you have it in the documents or not, it's earned. There are multiple factors that go into it, so having it in the documents, to me, is more helpful for the founder than for you as a firm. If you as a firm are asked by the founder to step back for whatever reason, that is up to you to say yes or no, knowing that if you say no, you are getting into a fight that you are likely going to lose in some form. You are either gonna lose it financially in that you're not gonna get your pro rata because of whatever mechanism can be used to remove your pro rata, or more importantly, you're gonna lose it because of reputation. You are gonna piss off the founder, and they are not going to like you anymore. So if you say no to a founder, and you wanna take reputational risk, that's on you. So why is it important to have it in the documents? Because I think that funds that follow you into rounds, in the A and the B, they are happy to squash you in any way they can. And the more that you have it in the documents, the more leverage a founder has to negotiate the terms of their next round. So if a firm comes in and says, "We want 22%," and you look at your cap table and you're like, "I have 6% of my cap table that needs pro rata," you're able to actually create more leverage with your follow-on investor to say like, "I- that math doesn't work for me. I would like to redo this." And then you can use that in, in help of your negotiation.
- HSHarry Stebbings
Do you see large firms be more ownership-hungry or more willing to accept less ownership?
- DTDavid Tisch
Haves and have-nots. So I think there are firms sometimes that need 20% in a deal, and then you're like, "But last week you did a deal at 5%." And I see it, 'cause I'm in that deal, too. Uh, and so I always think that's funny when the word need comes up in venture [laughs] and you're like, "I, I know what need means, and it does not mean need." Uh, it means I'd like, like I hope for, but it doesn't mean actually a binary, uh, need. Um, I think within the big firms, there are very different style actors. I think there are, uh, people who are on the way up or competitive inside of their firm that behave one way, and there are people that are very confident in their position at a firm and their standing and their success that behave a different way. And, you know, you can say junior or senior, whatever terminology you wanna use, uh, for that, but I think that, um, you know, relationships matter. There are times when we send a deal to a multi-stage firm and they write the term sheet and then [laughs] try to squash us. And I'm like, "That's weird." Like, those tend to be, again, this orientation towards short-term decision-making versus long-term and not appreciating the, the consistency of a relationship. And I think in my... Again, I've been doing this a long time. There are people that you build great relationships with that tend not to have overly sharp elbows with you, and then sometimes you catch a elbow out of nowhere and you're like, "Ooh, I didn't see that one coming."
- HSHarry Stebbings
Who, when they send you a deal, do you pay most attention to?
- DTDavid Tisch
Great founders. That's who I pay the most attention to. When founders inside of our portfolio, and I don't think it's the best ones only. I think it's the founders who we believe have high-quality taste bars and high-quality networks. When those people send you someo- someone they know, someone they like, that's when
- 52:30 – 57:29
When Should VCs Take Money Off the Table?
- DTDavid Tisch
you pay the most attention.
- HSHarry Stebbings
When you look at one part of our business that's investing, another part is also bluntly making money for our LPs and, and selling, and we have very liquid secondary markets today. How do you think about that and taking cash off the table when there is so much demand for some of these names?
- DTDavid Tisch
I work for our LPs, and my customers are founders, and that, I think, is a totally, again, dislocated, uh, two sets of relationships. My job is, as you said, to give the people who believe in us and invest money in us as much money as I possibly can. And one way to do that is to try to get out of positions at different times, and there's a risk to it. Uh, and there's a financial risk to it and a relationshi- a, a, a sort of reputational risk to it. And I think that's a really important thing to balance. So on, like in general, we don't sell early. We believe we are investing at the seed stage to join the founder for their journey. And that could be 15 years. It could be 20 years. It could be four years. Uh, but selling early to me risks two things. One is, like, if a founder doesn't want you to sell early, you're risking reputational risk and relationship with that founder. In this market, a lot of founders are taking secondary, so you could argue, like, "If you're doing it, I can do it." I don't think that's necessarily, uh, the right framework. I really don't. Um, and I can talk about why. But I don't use that framework, um, to think about it. Uh, and then the second one, I think the best companies compound the most at the end, right? Going from, like, a $2 billion to $4 billion to an $8 billion company is easier than going from zero to a billion. And if you believe that you are in a company that's great, I don't see why you would get out early. I think you're leaving the most money on the table by getting out of something early, and I really don't wanna do that. I wanna see it through. And if I still believe in a company or one of my partners believes in a company, I don't think de-risking it is the right answer. We're in the business of risk, and we should, uh, stay investors in the companies that are gonna keep compounding 'cause every turn you have at the end- Is a, is a big win for your LPs and for your firm and for the founders
- HSHarry Stebbings
Why do you not think that if a founder's taking money off the table, investors should maybe do the same?
- DTDavid Tisch
'Cause I think founders have a different set of economic conditions that are d- are, are not related to what investors have. Let's say a founder has debt. Let's say a founder is living in a place that creates stress and overhead cognitively for their life. And in reality, having some money to improve some things outside of work allows them to be better at their company. Or knowing that I have $10, $20, $30 million in my pocket, I am now willing to see this through. I'm willing to, to have bigger risk appetite, to, like, go for it because I feel some safety net. I don't think that that is the same risk analysis that a VC uses to be like, "I need to take, you know, 20% of my position off here to, like, make my fund math look good or tell my partners I, you know, took some money out of this thing." I just think they're totally different. Or giving early employees, like, a tender offer and allowing them to have some early liquidity, I think it could help with retention. Um, I think it could keep a lot of those employees happy and engaged and, um, you know, excited to, to work at a company knowing that they offer tenders every couple years. Um, we have a bunch of companies in our portfolio that are regularly doing tenders to the employee base, and I think that that's an incredibly, uh, valuable culture to set and, uh, a retention tactic. And so I just don't believe that they're always related.
- HSHarry Stebbings
What did you believe about venture that you now no longer believe, David?
- DTDavid Tisch
It just took a while to see, right? Every firm thinks you're in the top decile, right? In, in an industry-
- HSHarry Stebbings
I've, I've never heard any firm be like-
- DTDavid Tisch
[laughs]
- HSHarry Stebbings
... "No, we're bottom, bottom quartile."
- DTDavid Tisch
Right. So I'm, I'm, like, waiting to meet all the bottom three quartile firms in the, in the venture industry. When you hear all the LPs explain that, and you look at the, the data and it says, you know, all the returns in venture are aggregated to the top 5, 10% of firms, uh, I just, m- I don't, I haven't met the, the others yet.
- HSHarry Stebbings
Do you think we'll have more or less VCs in five years'
- 57:29 – 1:02:23
Why Venture Is Consolidating Around Fewer Winning Firms
- HSHarry Stebbings
time?
- DTDavid Tisch
Less. There's less noise in the venture market than ever before, and there's more competition.
- HSHarry Stebbings
What do you mean less noise and-
- DTDavid Tisch
And so you had asked before... There's less new firms.
- HSHarry Stebbings
Really? There f- it feels like there's more spin-outs than ever before.
- DTDavid Tisch
I think there are less. Like, I think on a... I think if you actually look at the data, you know, it takes a long time for firms to go away, even if they're still alive. They become irrelevant. They're not investing a lot. They might not have raised a new fund. Nobody's sort of taking them off the map. So the names remain, but the activity goes away. Um, you know, you had asked before about, like, sub $100 million in San Francisco concentrated seed funds. I think I, like, didn't answer that fully. I don't think very many people get into venture s- and want to stay consistent in doing what they do. Meaning, the starter VC is a seed fund, right? You get, like, if you're new, if you're sort of unproven, you'll get a 20, 40, $80 million fund, whatever it is, to start. But your goal is to raise a way bigger fund one day. And when you raise a bigger fund, when you scale your business, when you have partners and scale AUM, your investment style, your stage, your concentration, your check size is all going to fundamentally change. So when I meet new investors, I always ask, like, "What's fund four look like?" Because fund four is actually your vision. It's the same as when you meet a founder and you ask, "Okay, what's the big vision?" So I wanna know not what fund one is doing today. I wanna know where you're going with this. Because to me, the advice that you give that person should be in line with how do you get to your actual ambition, not how do you execute your starter fund. And I think what you see in the new firms today is a big ambition. They wanna start with something small and get bigger and do something different really quickly. And I think what's I, I love about what we do here is this is who we are. This is who we've always been. We are an early-stage firm. We write checks at the very early stage, and we don't have any ambition to do anything else.
- HSHarry Stebbings
No, but the r- but, but, like, to be clear, like, you did just raise, what, 550 across two funds. I mean, the, the, I get you-
- DTDavid Tisch
We've scaled.
- HSHarry Stebbings
Yeah, the scale has changed.
- DTDavid Tisch
We've scaled the, the, the... Sure, but the same exact investment style. And I think we see founders today come to us and say, "You're doing the same... Like, you're, you're exactly where you were 10 years ago when I started my last company." Maybe the check size is different, but we are not... We as a firm, our DNA, our craft, is oriented towards being there at the very beginning, at the dream stage. And that to me is, like, what I wake up and get excited about. And I think that, uh, when you look at n- new venture firms, their, their ambition is to be a multi-stage firm for the most part. And that's a very competitive part of the market.
- HSHarry Stebbings
It is. I don't actually think they know what their dream is. And I know, I, and, and what I mean by that is, like, you know, one thing I would say to young people, and I sound really old, is, like, be careful what you wish for because you might just get it. And I think the truth is if you know the people at the multi-stage firms, a lot of them are not happy, the ones who are running it, and wish they were the smaller firms. [laughs]
- DTDavid Tisch
Yeah, but I think, I think, I think there are different form factors of the multi-stage firm. I think you see Benchmark scaled today, USV scaled today, and the DNA inside of those firms and the relationships inside of those firms are very different than some of your other scaled- Firms. I think what Conviction has done is amazing and scaled. I think what Ribbit's done is amazing and scaled. And then, then you go to Thrive. Like Thrive has created a generational venture firm in a different flavor in a rapid amount of time and challenges at the very top of venture. And I think the way that they've built that firm is so different than, again, your traditional multi-stage firms. And so I don't think it's as simple as categorizing every firm as the same. I think you have to look at each firm individually and the execution of how they've done it. I think, like what Daniel and, and Nat had done for the moment, that was incredible, and what Alad has done is incredible. And so I think if you... All those firms I just mentioned are new, right? In, in the grand scheme of things, I guess Benchmark and USV are not. The, but the other ones are new. And the speed at which they've gotten to where they've gotten is incredible, and the, the quality of what they've built is incredible. And that was ambitious. And I think when you look at the new firms today, I think the, the ones that are great are gonna execute great and have real ambition and make a real space for themselves in this industry, and the rest of them are gonna
- 1:02:23 – 1:05:57
Finding vs Picking vs Winning: What Actually Makes a Great VC?
- DTDavid Tisch
go away.
- HSHarry Stebbings
When you think about finding, picking, and winning, if I were to ask you to review yourself one through three, one being best, two being mediocre, three being worst, how would you review yourself?
- DTDavid Tisch
I just think we're mid constantly. Uh, no. [laughs]
- HSHarry Stebbings
[laughs]
- DTDavid Tisch
That's what the kids say. Um, our obsession at our firm is to, to see things. We all wake up every day and try to see. I think we see somewhere between 50 and 75% of what we wanna see. Hard to know, but we can always be better there. There's like always something out there that we didn't see that we want to see, and getting in front of people, finding a way not just to get in front of them, but for them to take you seriously, um, that's like what we wake up and obsess over. Winning, when you don't win, it hurts. Like that, that is like a, that's like a, a what could we have done better? It is the area in venture I think you can tactically work to improve. You can try different things. You can like figure out what you can do better. Uh, and I think we spend a lot of time on that.
- HSHarry Stebbings
What has that led to? You spent a lot of time on that. What have you changed as a result?
- DTDavid Tisch
Everything. I mean, you, you have to know what tactics to bring to the fight, and that's like reading a room and guessing which playbook of really relationship building that you want to use. What does a founder want from you? What are they looking for, and how do you convince them that you are the answer to what they're looking for? And it really is so founder-dependent. Each f- like there are certain founders that don't want to talk a lot. There are certain founders that want transactional help. There are certain founders that want a friend, that want a, like, set of experience, that want somebody who is around all the time to balance things. Like y- it's a services industry. And so the win condition to me is selling your service to the point where a founder wants it, and that's complicated, especially in this market. The picking is the art of this business, and it's so hard. You can look at our firm from afar and assume we say yes more than other firms. I don't, we don't. We are hyper-focused on saying yes when we should, but that's a really, really hard thing to do at the early stage in real time. And I, I like want to tell you I know how to get better at that, or we can get better at that, and yet, like there, there comes a point when you're in your career and you've seen enough reps that your taste is your taste. And you're gonna say yes. You're like butterflies show up, you're gonna say yes. They don't, you're gonna say no. You can convi- like we think about how to make the right decision a lot and don't know the tactics to get better at it.
- HSHarry Stebbings
David, how many companies do you meet a week as a firm?
- DTDavid Tisch
A lot. 50 to 100.
- HSHarry Stebbings
So people are meeting 20 companies a week.
- DTDavid Tisch
Yeah. At least.
- HSHarry Stebbings
Okay. And then every Monday you come for an IC and you talk about the five best? Like w-
- DTDavid Tisch
Tuesdays and Thursdays.
- HSHarry Stebbings
Tuesdays and Thur-
- 1:05:57 – 1:09:56
Why BoxGroup Doesn’t Allow “Grenades” in Investment Committee
- DTDavid Tisch
Twice a week.
- HSHarry Stebbings
Twice a week. Okay, different-
- DTDavid Tisch
We use Mondays for work. We are agile with our decision-making. I think groupthink is terrible. We don't vote. Somebody here has to wanna do a deal if we're gonna do it. Somebody needs to be like, "This is something that I am excited about and I think we should do." And so I think decisions start with a human on our side being excited about something, and whether that happens inside or outside our meeting is not important. And so if we get to our meeting and one of my partners is like, "I did a deal yesterday," great. And equally so, like, "I'm leaning into this. I wanna talk through it," great. We internally don't allow negativity in making early stage decisions.
- HSHarry Stebbings
What do you mean by that?
- DTDavid Tisch
If you aren't the person that has spent time with the founders, you aren't allowed to be negative about it.
- HSHarry Stebbings
Right. But what if you know something about the market that you feel the-
- DTDavid Tisch
Sh- it... I don't think anybody knows anything about markets at the early stage. Markets evolve. Um, if you know something about the founders, but we've probably diligenced that before we're taking meetings and leaning into something. Like, if there are, like, ethical issues, if there's reputational issues with a founder, I think that is an important thing to share. We don't allow grenades at early stage. You're not allowed to throw a grenade on someone else's deal. Our job is to get to yes. It's... I- if you name a company at early stage, I can tell you why it's gonna fail. Any company. Here are the f- five risk conditions, and here's why it's gonna fail. It's the easiest thing to do. If you've done this for, like, a year, you can guess why a company's gonna fail. Your memos that every firm writes are very obvious why it's not gonna work. That's not the job. And by the way, on a probability basis, it's not gonna work, 'cause 70, 90, whatever the number is, percent of early stage companies don't work. So you explaining why something isn't [laughs] gonna work is incredibly obvious and incredibly irrelevant. What the magic of our business is, is squinting and seeing why something is going to work, by believing in the thing that you see, that the founder sees, that you are aligned with the founder in seeing is going to work, and saying yes. Our job is to say yes to the right things, not to be fearful of saying yes to the ones that don't work.
- HSHarry Stebbings
Totally get that and understand that. I always love that Google will just build it or the, you know, OpenAI or Anthropic will build-
- DTDavid Tisch
Whatever it is
- HSHarry Stebbings
... yeah
- DTDavid Tisch
But, but, like, you can't hire. You don't know how to hire. You're not gonna get... Like, it's not big enough. All these things, they're just not factors for the win. Why is it gonna work?
- HSHarry Stebbings
You said that 70 to 90% don't work. Keith Rabois said before that's dramatically overestimated, and in fact, if you're investing in great people, actually, your loss rate, in other words, it actually really not working, being at a zero or close to a zero, is much lower than people think.
- DTDavid Tisch
I think at series A, that's true. I think at seed, it's, it's some real scale of, of numbers.
- HSHarry Stebbings
You do?
- DTDavid Tisch
But I think, I think you go one stage ahead, and that number is dramatically lower.
- HSHarry Stebbings
Hm.
- DTDavid Tisch
I also think Keith is a generationally talented investor, and if his loss rate is, I don't know, a 10th of everybody else's, that wouldn't surprise me.
- HSHarry Stebbings
Yeah. No, I, I totally get you. Um, listen, David, I wanna do a quick fire. So I say a short statement. You give me your immediate thoughts.
- DTDavid Tisch
How short?
- HSHarry Stebbings
Does that sound big?
- DTDavid Tisch
I'm long-winded.
- HSHarry Stebbings
Like, s- 60 seconds per one.
- DTDavid Tisch
Let's go.
- HSHarry Stebbings
I'm gonna set a timer.
- DTDavid Tisch
All right.
- HSHarry Stebbings
You can choose one seed fund, one series A, and one growth fund to be an LP in. Which
- 1:09:56 – 1:13:06
The Best Seed, Series A and Growth Funds in Venture
- HSHarry Stebbings
one?
- DTDavid Tisch
I think Y Combinator has invented the only product in our industry, and I think for all the people that say anything, you know, critical about them, it's probably just rooted in some version of jealousy. I think what they've built is a world-class brand, a world-class attractor of great talent, and I think run the best business model, uh, in our whole industry. Uh, so seed fund, like YC.
- HSHarry Stebbings
Series A.
- DTDavid Tisch
I think there are five to seven equally impressive, like, multi-stage firms that just continue to find themselves in the best companies. You can choose Benchmark. You can choose Sequoia. I think the machine Andreessen's built, I think what Thrive has done. You know what, what Lee Fixel does at Addition is, uh, fascinating and off the radar in an interesting way, and sometimes is a great series A investor. So I think, uh, you know, I think what Ribbit has built over the years, if you look at what they've done, is incredible, and so I don't think, uh, I, like... And then you have Founders Fund, which operates in their own world and is incredible, and I think, you know, we, we said Keith, Keith Vekosla has done generational level investing. So I ju- I actually don't think at series A it's easy to isolate, because you're looking at this combination, if you put your LP hat on, of, like, fund size, accessing early stage versus growth, these blended products, uh, and I don't think it's a black-and-white answer. Like, I think the two funds that were just very narrow focused for series A over a historical period were USV and Benchmark, and I think they've changed their fund size today, um, but not really the partnership dynamic.
- HSHarry Stebbings
Yeah, absurd punting there. Uh-
- DTDavid Tisch
Yeah
- HSHarry Stebbings
... growth-
- DTDavid Tisch
I weaved in and out of your forced question.
- HSHarry Stebbings
Uh, growth fund, you got one growth fund.
- DTDavid Tisch
Again, like, I think there... Like, I think Spark Growth comes to mind as a amazing, slightly off the radar, just, just unique outlier, uh, decision-making. I think what Meritech did for a while, I think what Menlo's done, these are new, like, names in my, uh, weaving of your answer that I wanted to get at. I think what Coatue's doing or Dragoneer's doing right now, uh, I think are interesting-
- HSHarry Stebbings
You are a fucking... You're fucking-
- DTDavid Tisch
Yeah
- HSHarry Stebbings
... Switzerland.
- DTDavid Tisch
I, I am Switzerland.
- HSHarry Stebbings
Yeah, why are you-
- DTDavid Tisch
But, um, but I, I mean it
- HSHarry Stebbings
... sh- show us your tubelord, David. Come on.
- DTDavid Tisch
And I'm probably forgetting, like, a hand- but I mean it. I think there's a tier... Uh, Green Oaks, right? I could easily just say Green Oaks is the answer to your question.
- HSHarry Stebbings
No, because I, I'm asking you, I want money. Dollar for dollar, where am I gonna make the most money?
- DTDavid Tisch
I think it changes in every mar- like-
- HSHarry Stebbings
Yeah, but I can give you mine. YC, I agree with you for ownership. No one gets the ownership they get for the dollar.
- DTDavid Tisch
But I think YC is the only differentiated product in venture.
- HSHarry Stebbings
Uh, and then I think Benchmark for series A, and then I think Sequoia for series B and beyond. That's mine.
- DTDavid Tisch
So you're discounting Sequoia's early stage investing? I'm not.
- HSHarry Stebbings
I'm su- I, I'm suggesting that-
- DTDavid Tisch
I'm giving them credit for both
- HSHarry Stebbings
... I would, I'm su- I'm suggesting I would rather the B and YCs than Sequoia
- 1:13:06 – 1:16:43
Why the Best Venture Firms Will Keep Compounding
- HSHarry Stebbings
seeds, yes.
- DTDavid Tisch
So I think, I think the real answer to your question is you're in a period of consolidation in venture, and the best firms are gonna continue to compound in every which way, because they're gonna access the best founders, they're gonna access the best scaled LP capital, and it's gonna turn into the best set of returns, and there's gonna be a haves and have-nots in venture. And, uh, I think there's probably, you know, 20 to 30 names that are competitive and probably 10 that are, uh, outliers amongst that 20 to 30.
- HSHarry Stebbings
What was the single most memorable founder meeting in the last 12 months? F- first founder meeting.
- DTDavid Tisch
Like, in our firm, uh, my partner Greg, you know, got to spend time with Noah from Instinct, um, early. And I think for him, that was the, like, mind-blowing initial meeting and conversation, and we were lucky enough to be part of, uh, that early round.
- HSHarry Stebbings
Whoo, baby. Well done.
- DTDavid Tisch
I, I think for me, the things we've done in the past 12 months are not mature enough yet to talk about because they're coming. And-
- HSHarry Stebbings
But just, like, whi- which, which founder did you find most mind-blowing where you were like, "I left, like, wow"?
- DTDavid Tisch
I have to be as excited every time I say yes. So I actually, I don't operate like that. I operate like this. And if something rises above this, you lean in. And if something doesn't, you lean out. And so I view my job as a continuum of, like, steadiness in order to make the right decisions. And so it's not f- I, I think what to this point satisfies me the most, to answer your question, is, like, the relationship that comes out of it. Do you click with a early st- Like, we funded this 22-year-old who's building a game that's gonna release, uh, in like two months. Like, a single game. Level of difficulty, one trillion, right? To win a game business. But, like, he has been thinking about this game [laughs] for a long, long time, and we're gonna see if it, like, hits. And if it hits, it's gonna be awesome. But, like, low probability of market. All these factors are negative, but he's awesome. And then I met this woman who's building this really cool piece of hardware that goes in, like, your home. It's a point solution that's, like, huge market. Everybody has a need for this. But, like, again, level of difficulty, impossible. And then you meet, like, veteran founders who are building a foundational model for, uh, you know, a physical world application. And you're like, "Well, that's crazy, and you guys seem like totally the right people to do this." And then you have someone in science who's doing something. Um, so I really do believe you have to be excited about everybody in some form equally. Who do I like hanging out with? I like, I like ... I'm a consumer mindset. I find the consumer founders the most interesting 'cause they're nuts. 'Cause [laughs] they're, they're going after the biggest con- most confusing end user. And I think, uh, you know, that, that's ... Like, I learn from them. Uh, we're an early investor in a company called Triumph. I think spending time with Jake, uh, is, like, an amazing, uh ... I- I love talking to him. I love hearing about what they're doing. Um, I think they'll start making a lot of noise in the coming year, uh, and
- 1:16:43 – 1:20:31
What David Is Most Excited About for the Next Decade
- DTDavid Tisch
sort of be one of those haves.
- HSHarry Stebbings
What are you most excited about in the next 10 years?
- DTDavid Tisch
I think seeing this play out, right? Like, where, where are we going? Where is the world going? It's, like, such a curious uncertainty right now. And, uh, like, that's what makes this job a special opportunity, is you get to meet the people who are gonna answer that question, um, and get to be part of their journey. I don't know.
- HSHarry Stebbings
What is certain in the next five to 10 years?
- DTDavid Tisch
What should be? Like, autonomous driving. That should be. Like, it irritates me that it's not today. Like, it would save lives. It would save ... It would. Like, the data on autonomous driving would save hundreds of thousands of lives worldwide if we just mandated it. But yet, like, freedom and all these other factors go into holding that back, but the technology is a solved thing.
- HSHarry Stebbings
Well, I, I mean, I'm not gonna, I'm not gonna be-
- DTDavid Tisch
I, I think it's a society-
- HSHarry Stebbings
The tech- the tech- the technology's not, like, quite a solved thing for ambiguous cities, for challenging weather conditions.
- DTDavid Tisch
It's pretty solved. Pretty solved. Like, from a, from, like, a safety profile perspective, it's pretty solved. It's not perfect, but pretty solved. Like, if I told you pretty solved equals decrease of 80% of the deaths that automobiles cause, pretty solved. But freedom, like, I don't like that as a society we don't adopt future things because we hold on to, uh, the wrong establishments.
- HSHarry Stebbings
Well, it's 'cause incentive design is, is skewed in a lot of frameworks, and there are existing incumbents-
- DTDavid Tisch
I think, I think modernizing society long term is the, the, the right way to, to think. I think, like-
- HSHarry Stebbings
And do you know what? Do you know what? I, I agree with you, and I, I think it's kind of like the roll-up play versus an entirely new company play. I think it's much easier to create an incredible AI-first school from nothing than try and incentivize innovation in stale architectures.
- DTDavid Tisch
Or we should do both.
- HSHarry Stebbings
You should ... No, you can try both, but it's much easier to do the first.
- DTDavid Tisch
But, but, like, just move forward, right? And I think, I think, like, the politics, the social dynamics, the economic dynamics of all of the challenges in the world would be best served with, like, practical decision-making than charged, uh, decision-making. And that, I hope, uh, is where we find ourselves over time. Because if you end up in the age of abundance, I think it's important to figure out, like, how does that benefit everybody and not just a few? And I think technology generally is a equalizer and a positive force. And I think, uh, hopefully AI can move in ways that impact health, impact science, impact, uh, every industry such that it benefits a, a global population, um, in, you know, great ways.
- HSHarry Stebbings
Dude, I, I think this was probably the most low-friction conversation we've had. There wasn't, like, a dramatic dip-
- DTDavid Tisch
Should we fight at the end?
- HSHarry Stebbings
Well, I don't know. I feel like we should at least try. Yeah. Like-
- DTDavid Tisch
What do you ... Well, we f- we fought over you deciding benchmarks for the only good VC fund.
- HSHarry Stebbings
It was the most nerdy venture fight when you actually ... We, we fought about ownership versus diversification in portfolios. You're like, "All right, guys. Calm down." Um, dude, I, I love chatting to you. I, I have so much res- Regardless of me being wrong, I have so much respect for the business that you've built.
- DTDavid Tisch
Thanks for having me. I, uh-
- HSHarry Stebbings
No, dude. No, not at all
Episode duration: 1:20:41
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