# AI Investment Strategy: Valuation, Durability, and Portfolio Nuance

**Podcast:** The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
**Published:** 2026-03-09

## Transcript

sometimes getting overly fixated on the financial metrics in this environment can leave you just like with an unsatisfying taste in your mouth.
Growth can obscure and blind you to a lot of underlying ills in the business.
I think you can actually be successful in this market investing in consensus.
Investing is an art and a science.
The science is understanding how to properly value a company and the art is understanding when to break the rules.
Focus on hitting singles and doubles and let the home runs take care of themselves.
This is 20VC with me, Harry Stebbings.
Now stay, I'm thrilled to welcome a dear friend to the show, Miles Clements.
Miles helps lead Excel's growth investing practice where he's backed some of the best in the business, including Atlassian, Linear, Cursor, and many more incredible companies.
Now, Miles is an old friend and so this was a very, how do I put it?
No holds barred discussion.
I think he put up with a lot of very pressing and prying questions.
And I don't think you've ever heard an Excel partner be quite as open and honest as this, which was just fantastic.
Miles really was very special to have on.
But before we dive into the show today...
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Miles, we are in person.
I love it when you're in town.
It's so lovely to see you, man.
And it makes it so much more special doing it in person.
So thank you for joining.
Yeah, thanks for having me.
It's always fun being here.
Now, I want to start with the core question that I think every investor is thinking about, which is how do we ascertain true value in an AI world where technology seems so transient and revenue seems so endurable?
I think in terms of evaluating these AI categories in companies, there's a pretty useful framework, which is basically trying to understand a company's time to value and then the durability of that value.
So I think that a number of these companies sort of shine on different dimensions.
If I were to look at legal AI.
accounting AI, a company like Basis that we just invested in.
I actually think these companies don't have immediately quick time to value.
And so when you look at like the deployment cycle and getting lawyers and getting accountants sort of sold on the technology, that can take a little while.
But once it is hooked, the durability of that value is like transformational to these firms.
On the other end of the spectrum, I would take some of like the very early vibe coding companies, right?
Very quick time to value.
Like you start vibe coding, all of a sudden you have a weekend warrior pickleball app ready to go overnight.
You can start using something very quickly, but the bottom just fell out for a lot of these apps because there was no durability of value.
The reason that I think coding has become like the vertical in AI is because it shines on both dimensions.
Like you can start using cursor in an afternoon and by that evening, you're 10 times more productive.
The time to value is very short.
And then the durability of that value compounds as the team starts using it.
QuadCode, Cursor, all of the great products out there.
Like, I think this is why coding has become the vertical that is the battleground in AI today.
Jerry Murdoch on the show said from Insight the other day, not me, but like overheard from my portfolio, no one's using Cursor anymore.
Everyone's using QuadCode.
We just saw Chamath tweet last night.
We're going to have to move off Cursor because it's just simply too expensive.
And the Twittersphere seems to have turned against Cursor with the Cursor is dead meme.
But then they hit 2 billion in ARR.
I'm trying to...
understand what is going on here?
I think there's a couple of things at play.
I saw the Chamath tweet.
I listened to the Jerry Murdoch show.
With all due respect to those guys, I think there's a few things at play.
First of all...
this market is growing enormously and i don't think a lot of these companies are actually experiencing success at the expense of the others take cloud code as an example first of all what an amazing product cloud code has absolutely captured the imagination in part driven by opus 4.5 opus 4.6 like i think the success of cloud code is also very much tethered to the success of the underlying model so it has captured the zeitgeist like that's unmistakable with that said I think these things are so market expansionary that it's not necessarily coming at cursor's expense.
And I think they're market expansionary on two dimensions.
First of all, they're bringing so many new cohorts of users online.
So people who would not have been software developers a year ago today can be software developers with these tools.
They're also expanding the market in terms of consumption.
You hear the ARR growth leaked for both companies.
A lot of that ARR is not like net new companies paying per seat pricing.
A lot of that ARR is consumption, which is off the charts for both tools.
I think that's one thing that's going on.
I think another is this sort of misunderstanding about Cursor being tied to the IDE.
In some ways, Cursor is a victim of its own success.
Like they were so disruptive and so innovative around the IDE like a year ago that people can't help but overmake the assumption.
What is happening, though, very clearly is like the world is moving to agents.
No one has been more vocal and thoughtful about that than Michael Truel from Cursor.
I just sort of look at the numbers.
According to like Michael's post, which was public on Twitter a few weeks ago, there are two times more people using agents in Cursor than using the tab feature.
90% of Cursor users are daily active users of the agent product.
The agent product grew 15x last year.
You know, the cloud agent product, which was new as of like October 30th, so it's only been in market for three months.
is now responsible for 35% of merged PRs and cursor.
Those are happening by cloud agents.
All due respect to Jerry Murdoch.
I think he said like, well, you know, I thought about this metrics, these metrics, and this company needs to pivot.
Like, all due respect, I thought about playing in the NFL, but instead I walked onto a college football team and was the fifth string inside linebacker.
You're not looking at any real metrics.
Like, who are these people to make these judgments?
So I get a little bit spun up about it.
The thing that's so cool about the team is like, they are focused, they are unfazed, and they're just building.
Do you think they are fundamentally challenged because of their reliance on, bluntly, Anthropic and their models and what that does in terms of cost inflation for end users of Cursor?
I don't think so.
I mean, I think in a number of dimensions, the beauty of Cursor is their ability to be multi-model.
I think it's valuable for a couple of reasons.
First of all...
We put this survey into the market.
You'll have to have me back on the show to give you the full readout because it's only 90% of the way complete.
We just wanted ground truth on what's going on with the mindset of developers today.
And one of the things that we're learning is 50% of developers switch model families on a daily basis, and 95% of developers switch models on a daily basis.
I think the world wants to be multi-model, and that experience is fundamentally enabled by Cursor.
The other thing that comes from being multi-model is you basically become like an index of AI.
innovation because you get this compounding product benefit where every new feature, every new enhancement that the cursor team makes, that obviously improves the product experience.
But every improvement with the underlying models also improve the capabilities of cursor.
And so you get this like compounding product flywheel that's very unique.
Was cursor wrong to focus on building their own models?
I don't think so.
I think what they're going to be able to achieve is incredible.
I also think we need to...
frame in the right context what their aspirations are with these models.
There are generalists and there are specialists.
Cursor is going to build specialized coding models that are going to serve specialized coding tasks, especially for a lot of enterprise users.
They don't need for their models to be good at poetry or teach you how to make an apple pie.
Their models are there for professional coders to do professional work.
And I think that that's very powerful and will continue to make the product experience really differentiated.
When you were investing at, what was the first round?
price 9.5 when we're doing like a 9.5 and a 27 what are we underwriting it to like if i was your partner i'd be like totally get it and this is super exciting but like what's the upside here how did you think about that there's a couple of ways to frame the upside one is that you think about like platform companies that are publicly traded that own their domains there's very few of them out there so salesforce historically has been like the go-to-market platform company crowdstrike and maybe palo alto are like the platform cyber security companies there has never been a platform company for engineering as a vertical And engineers are like, I mean, this is the fastest growing, most dynamic vertical there is, and no one has ever owned that.
Now, you've had companies that have built tremendous value biting off pieces of the stack.
Atlassian, hugely valuable company that we love, began around issue tracking, Datadog around monitoring.
These have been like 50 to $100 billion companies built over time addressing like one portion of the engineering product stack.
No one has built a platform company to own it all.
And we think they have that aspiration.
So that's one thing.
The other is like, we were also joking before the show that I think sometimes getting overly fixated on the financial metrics in this environment can leave you just like with an unsatisfying taste in your mouth.
Actually, this company is growing so quickly that on a multiples basis, our first investment was at four times, five times year-end ARR.
That wasn't like anything that we talked about or part of the underwrite.
Because now it's at two billion and you did it at nine, essentially.
The company said, I think a week ago, or it was leaked, that they passed two billion.
So yeah, that's a fair assumption.
What was it when you did it?
Just because you need to have that mental plasticity.
We had a conversation with Michael where we sort of said, where is the business today commercially?
And he told us, and it was, I'm not evading the answer.
I don't specifically remember, but maybe it was like a hundred of ARR.
Give or take, yeah.
You know, we said, what do you think is realistic for the end of the year?
He said, I think maybe like our aspiration is, you know, these assumptions go right and these are the products we're going to launch and then we can get to 500.
And Andrew Braccia, who I was working with, you know, Andrew and I sort of looked at each other and we were like, I think we should haircut and call it 300.
Like getting from 100 to 300 would be extraordinary for this kind of a company.
You know, they ended last year somewhere in the billions, I think has been reported.
But it really never was about and still is not about financial metrics.
The financials of this company, to me, are purely a reflection of the product market fit.
And it's unlike anything I've ever seen.
When you are so off in your ability to predict revenue at year end, how does that change your go forward investor mindset?
Do you just place no value on revenue predictions?
How do you think about that?
I think revenue predictions are important in that they sort of encode a lot of business assumptions.
If we get this product right, if our pricing here is correct, if our penetration of this customer segment works out.
we should be at this rough revenue scale.
But the idea of having a budget so that you can go hold the founder's feet to the fire quarter after quarter is just not really relevant.
So to me, the less important thing is if a company finishes 10% below plan, 10% above plan, we're not public market investors.
We're not managing to earnings calls.
We care a lot about the inputs that go into the assumptions, but the output is a little bit less important.
When we think about that and the revenue numbers that you see there it makes other things seem quite boring it does like i mean this is the sad case are we in a world where triple triple double double is dead when you can have a company like cursor going from 100 to a billion Absolutely not.
I mean, send me all of your triple, triple, double, double companies that you're not interested in investing in.
So I was thinking this last night.
Everyone says this on the show.
I guarantee you'd be like, no.
No, no, no.
Here's why.
I think you can actually be successful in this market investing in consensus.
And I think you can actually do really well investing in non-consensus.
I think you get hammered sitting in the middle.
You know, a company that's not growing.
15x year over year, that's fine.
There's all these other really important inputs that go into it that I think can make for a really interesting investment outcome.
I'm sorry, I still don't quite understand.
If you have a pot of money and you can put it in companies that are growing 15x, to then put it in companies that are growing 3x, 3x, 2x, 2x, the opportunity cost of your cash is real.
As your partner, I'd be saying, why are we doing that?
Yeah, but this is where we're ignoring all of the other important inputs, right?
Quality of the founder.
What market are they in?
What ownership are you getting in the investment?
All of these other things factor in too.
So I think one thing that's happened in our market is like investors have tended to just flock to the extremes.
Either like...
We're AI maximalists.
We're going to buy the basket.
Ownership valuation, be damned.
We want everything.
Or like, we hate the valuations.
They make no sense.
We're going to sit on our hands and wait until things cool off a little bit.
The reality is like the best funds in the world, the best investors in the world embrace the nuance.
The right answer is always somewhere in the middle.
Constructing a basket of companies where maybe some, they were undisputed breakout leaders and you...
didn't get the ownership that you wanted, but you wanted to be a part of that company and you wanted to be partnered with that founder, there's room for that in the portfolio.
But there's also bootstrap companies in Little Rock, Arkansas, where you can have a different ownership threshold and work with a really special founder and build the company in a different way.
And you can do very well that way too.
We don't really run from the nuance, like we embrace the nuance.
And there's a lot of benefit to being a multi-stage, multi-strategy firm.
That's wonderful, but your funds are too big to embrace nuance, dude.
How so?
I'm sorry, you need to have $50 billion plus companies to return your fund sizes.
I think we will.
I mean, think about this.
Like a decade ago, how many trillion dollar companies were there in the world?
No, and you're right.
I use this stat too and like the expansion of outcome sizes.
But like, dude, they're very, very rare and they take 17 to 20 years when you look at the majority of them.
But this is the cycle repeating itself.
And like to answer my own rhetorical, which nobody asked me to do, you know, a decade ago, there were zero companies worth a trillion dollars.
Five years later, there were six public companies worth a trillion dollars.
Today, there's a dozen companies worth a trillion dollars in the public market.
Plus, you have the labs, you have SpaceX and companies in the private market.
So the sizes of the outcomes are enormously bigger.
And I absolutely think that firms can make substantial returns in the late-stage business given those outcomes.
And I will say it's really hard if that's the only thing you do.
If all you're doing is buying late-stage momentum companies, I do think that's hard.
There are people that do it well, but it's hard.
I think being a multi-stage, multi-strategy fund where you also have a really focused early-stage effort and a growth effort, I think you can absolutely continue to support companies at every phase of growth and make a lot of money.
But can you do vertical SaaS growing triple, triple, double, double?
I wouldn't write off a company purely because that's the growth profile.
Now, I see the point.
You have to focus on large outcomes.
And I agree with you there.
I'm like to the team, we need to do two things.
One, we need to replace seats.
We're replacing labor.
And then two, I need to see a billion in revenue.
Before it was like 100 million and we can sell it for a billion or IPO.
A billion dollar exit doesn't...
doesn't do shit for us now.
Yeah, I agree with you.
As much as I enjoy sparring with you, I agree with you on this point.
If you can't articulate the big outcome, and if the founder can't articulate the big outcome, that is probably a sign that you don't want to be involved with the company.
But I think that what you're describing is basically the mistake that we made on a company like Service Titan.
We had fallen in love with R&V.
We were chasing this round.
It was going to happen in the...
$250 or $300 million range.
And, you know, we had these rigid rules about like, you definitely can't pay more than six to eight times forward for vertical SaaS.
And you definitely can't pay more than 10 times forward for vertical SaaS.
We lost it because we sort of got queued on price.
And then that went on to be a $9 billion company.
If you really understood the depth of the market, and if you really understood what they were disrupting in that era, you would have done it even though it was a vertical SaaS where you might have otherwise historically thought it was constrained.
When we said about Cursor, I liked your description of the platform company for engineers.
And I see it and I see that grand play.
But then it kind of goes against something that we kind of noted down before you said, who will win is a narrow-minded framing of the market.
Are they not paradoxical?
Like if you think about Cursor being that engineering platform company, totally get that.
And I believe in that view of the world.
But I don't believe the who will win is narrow-minded view.
I think Cursor will win.
I think there's huge value to being the winner in these markets.
But the reason I think the conversation is like the framing is overly simplified is people forget we don't operate monopoly markets in this country.
Like the forces of capitalism don't permit it.
And if they did, then the federal government wouldn't permit it.
So like I think the best software company in the world is AWS.
AWS has like 35% market share.
Everyone aspires to win.
And you get into business with these founders because you believe that they can win.
But I also think the way that a number of these verticals are going to play out in a number of the AI categories, there's going to be a couple of really big companies in several of them.
Do you not think we do legitimately operate in monopoly markets?
I mean, let's look at like NVIDIA.
Let's look at Apple for consumer hardware.
You know, Salesforce for CRM.
You know, Salesforce is a $250 billion business.
Yeah, but I think it's different when you get into, like, the mega cap companies.
Like, there are monopoly conversations, and that is, you know, what the federal government is there for.
Some would argue.
I would not argue, but that's what the federal government tends to do these days.
You know, I think in the private markets at the scale of companies that we're talking about, I just don't think so.
And, like, I'll give you one framing for, like, the winning conversation.
We've talked about, and you talk on the show a lot about deal.
People say like, deal has won the market.
Alex is phenomenal.
Deal has won.
We're not investors in the company.
I think it was published that they passed like a billion dollars of ARR.
It's incredible.
It's like, welcome to the big leagues.
ADP has $20 billion of ARR.
Like you are 120th the size of ADP.
And by the way, in this market, you've got like Paychex is a $60 billion company and Paycom and Paylocity.
And I think the venture framing of this company, one, is not always, you know, I think it can be a little bit oversimplified.
Do you reflect on those two?
You're not in deal or rippling.
Separate conversations.
We're not in deal because we're in remote and I'm thrilled that we're in remote.
I think Job and Marcelo are like very special.
I think their product vision is very different and unique.
The rippling one, yeah, I think about this one a lot.
I mean, this one stings.
Why?
I think a lot about like the physics of these businesses and like the product mechanics behind a lot of these companies.
And what I mean by that is I think a lot of investors tend to look at like.
what's the product, what's the growth rate, et cetera, et cetera.
No one really has an appropriate appreciation for what I think of as like the marginal ease of ARR accumulation.
What are the downstream levers that you're putting into place that you can pull on in the future that will allow you to grow at these crazy growth rates in year four, five, six, seven?
And how do you build this growth mechanism that is better than like, I put in a marketing dollar and I get out a dollar and 20 cents of revenue?
I think nobody in the world does that better than Parker Conrad.
So the first time he sort of outlined the vision, I was like, this is really compelling.
I think that's what he does.
He has this innate sense for pockets of margin that other people wouldn't go build companies around, like laptop provisioning and physical IT leasing.
That would be a tough standalone business, but as a revenue line item for a company like Rippling, it's really interesting.
I just think that Parker is a generational founder and we don't get it right all the time, but he's certainly someone I wish we were in business with.
Why are you not?
Was it because of the remote situation or price?
I think it was a couple of things.
Parker previously had a reputation.
I'm not going to opine on whether it was deserved or not, but he had a reputation that I like to think he's now totally overcome.
That just came up in the conversation and in a market where Mamoon was moving very quickly and other people were moving quickly, it probably made us a step slow.
I think this is also one where we stuck to our knitting on the investment framework, the ownership thresholds.
The opportunity to get involved was going to be at a high valuation.
And maybe there was, I don't remember the specifics, but there was a mechanism where you could invest more over time.
And it would have required us to break a lot of rules.
And I think, I don't regret not breaking the rules in general, but this would have been a time when it could have been worthwhile.
Exciting.
confused right now as to whether we should break the rules on series a's the prices have gone from 20 on 100 to 20 to 40 on 200 to 400 and i'm forced every day to question should we break the rules on ownership for these incredibly fast growing hot ai companies and we go back and forth on it we're friends sitting in a coffee shop what would you say to me if i was debating that Yeah, I'm chuckling because there's this funny quote that comes to mind.
I've been very lucky at Excel to learn from a lot of really great people.
One of them is Jim Breyer.
Jim used to say this thing, which I think he was paraphrasing from somebody else, but it was basically that like investing is an art and a science.
The science is understanding how to properly value a company and the art is understanding when to break the rules.
I just think in this market, like you got to do that constantly.
Generally speaking, sticking to your rules is a good place to be.
Now I do think...
You know, the vocabulary around what a Series A is in this market is just very different.
And so I would actually, you know, I think there's like multiple subcategories of investing that goes on in Series A land.
And you just have to decide what you want to participate in and what you don't.
It's okay to say no.
Like you don't have to be in every single round.
So I think that like breaking the rules is something you should do very, very rarely.
You said that kind of brilliantly wanky phrase, the marginal ease of ARR accumulation.
I'm going to give you five tequilas and then ask you to say that again.
Sounds wonderful.
Where did you think there was marginal ease of ARR accumulation where there maybe wasn't?
And what did you not see?
I think as the market has gotten more competitive, the pressure to be right.
to pick correctly has never been greater.
It causes you to extrapolate.
You have to extrapolate from early data points.
There have been investments where a company went from, they had a million dollars of ARR.
And then in the period before they fundraise, they had like a $4 million quarter.
And it's like, they've got it.
Like the product market fit snapped.
Like this is it.
This is the time to forward invest.
And you can extrapolate these trends.
And then it turns out sometimes they just had an anomaly quarter.
I have fallen into that trap before.
You have that more and more now when we see companies being maimed by others so significantly.
Yeah, yeah, definitely.
I agree with this.
I mean, I think this is why the benchmarks that used to give us all comfort are largely...
obsolete now.
And so like you have to be really clued into the usage intensity of your product and really understand how people are using it because growth can obscure and blind you to a lot of underlying ills in the business.
So I do think that being clued into like how people are engaging with the product, whether you're an enterprise company or a consumer app, it's more important than ever.
Do you find it hard, the binary nature of this world?
Honestly, we come into work sometimes and we're like, what the fuck are we doing?
I'm being serious.
I was talking to my dear friend Jason Lemkin the other day, and he's like, fuck this.
I've had enough of this.
I just want to do an anthropic SPV and go home.
I don't want to pick the winner in a SaaS company.
Oh, my God.
We feel so unimportant.
I have to be honest with you.
No.
I fucking love it.
To be really honest, I'm so lucky to be in this industry.
And the competitive thrill of chasing down these founders and chasing these deals, it's awesome.
How lucky are we to get to do this?
So no, I understand where you're coming from, but I love it.
When we look at the big exits this year, you've got Databricks, you've got Anthropic, you've got OpenAI, and you've got SpaceX.
As a partnership, do you guys lament that you're not in them?
Of course.
I mean, we are in some of those companies, but we, yeah, absolutely.
Nobody is harder on us than we are.
We want to know where we went wrong.
We also, though, we do that in the interest of getting it right going forward.
And when we look to the future, there's a lot of things that we're really excited about.
A lot of companies where we are sort of the investor of record, we intersected them very early, continued to buy up all the way through the growth stages, and we're excited about those.
But absolutely, we hold ourselves accountable when, you know, we miss companies.
I spoke to one of your LPs before and they said, help me understand why we're not in any of the foundation model companies.
Why are we not in Anthropic and OpenAI as an Excel LP?
Was that just like a miss or was that a belief that they wouldn't be good companies?
A lot of firms miss the model companies early and we're guilty of it.
Nobody has looked in the mirror harder than we did and course corrected.
Can I ask, when you did, is it like a partnership meeting?
Hmm, have we fucked up?
Or is it like an unspoken rule like the British people when it rains and we just pretend it doesn't rain and we walk anyway?
No, like it's the most important conversation there is.
So it's a global offsite where every partner at Excel sits in a room together and we say, how did we not get this right?
And how do we fix it going forward?
What are the 50 best private companies in the world right now?
And for how many of those companies are we not just a passive shareholder, but like the investor of record?
And what is our score?
And then what do we think is the next set of 50 companies and how many of those are we going to win?
And like, if we're not getting better, no one will beat us up more than we will ourselves.
So that's what the conversation is.
I mean, it's the most important thing for the entire partnership globally.
Are you playing a coverage game?
You know, when we had Anish from Andreessen on the show, he was like, 100% we are playing a coverage game.
We get split up fiefdoms and we get split up stages and split up categories.
And you are expected to see 100% of yours.
And if you miss, it is not acceptable.
For me, for example, we play a different game.
I don't have to see 100%, but I need to hit one of the big ones.
Yeah.
We're organized a little bit differently, but of course we hold ourselves to the same standards of coverage.
I mean, the aspiration is 100% coverage, 100% win rate, right?
No one in the industry does 100% of both, but if we're failing on one dimension or the other, we're going to talk about it and understand where we need to be better.
What was your win rate today?
How would you measure it?
When you go for a deal with a term sheet put down.
Mine individually or as a firm?
As a firm.
I think a healthy win rate would be like 80%.
And the reason it's not 100% is because...
Dude, no one's going to have 100%.
Some people have come on this show and said that they have 100% win rate.
And you should.
Andreessen.
Well, I wasn't trying to call him out specifically, but I've just heard it said before.
Well, no, no.
If I said I never lost a deal, I'd be happy if someone said it to me.
I don't mean to be combative about it.
I think my polite and professional response would be, I think if you're not...
putting yourself out there and losing sometimes.
You're not chasing competitive enough things.
I really like sticking my nose in a competitive fight, like that I have no right to win.
I really like doing that.
But I also really find a lot of joy in finding these founders who are just doing things a little bit differently.
Maybe they've bootstrapped the company.
Maybe they're located in some geography that's far away from Silicon Valley.
And having these non-consensus ideas that other people might think are silly or they might not really have their heads wrapped around, I think that's great too.
Is that kind of growth equity technology venture not inherently the most fucked in this AI world?
I think that business has gotten harder.
And I think that was like, frankly, that was the core of our early growth strategy.
Unbelievable.
Like the bootstrap, like one password, Qualtrics.
Totally.
Mike and Scott.
From bumfuck nowhere.
Amazing.
I love this.
Absolutely.
And that is still out there.
And we still do a lot of it.
And we aspire to be the best in the world at it.
Is it still out there in the world?
It is.
This is the funniest thing.
Every time we have an offside or a strategy conversation, we keep saying like, there's no more bootstrap.
There's no more bootstrap.
And then like.
you find a Laravel.
Like they are still there.
They're really hard to find.
And I think we're like the best in the world at finding them.
And it makes sense from opportunity cost of capital to put your money there versus just putting another 100 million into Cursor.
Nuance in portfolio theory.
A part of our business will always be doing that.
It's very distinctive.
How big is the growth fund?
At the moment, we have a $1.4 billion growth fund and we have a larger sort of later stage pool of capital.
No, 100% is like 1.4 and then you've got leaders, which is like three or four.
Is the growth fund subscale then?
Because David George has got six or seven to play with and Josh has got nine to play with.
Is that subscale or should we think of leaders as the growth fund in the same way?
In many ways, the market today is like what the venture market was in 2000, but inverted.
So the idea was like, I'll do my series A, I'll get 30% ownership.
I'll take a bunch of dilution.
And when the company goes public, I'll own 20% of it.
That was like roughly the math.
Today, you have to back into 20% the other way.
You do what the market will allow in the earliest possible investment.
You sponsor a tender.
You do a growth round.
You do an IPO round.
And you can ladder your way up to 20% ownership.
You have to be a multi-stage fund to do that.
Or you hope and pray that the expansion or like the multiple or the size of the exit, sorry, is so much bigger than it was.
It's not a billion to 5 billion.
50 to 100 that actually having five percent is actually just as meaningful as having 20 of the prior Sure.
I think you won't be surprised to find that, like, I don't think hoping and praying is a great strategy.
Dude, we are all fucking hoping and praying right now.
I'm sorry.
That is an absolute, like, Figma is an $11 billion company.
The unbelievable, unwaveringly brilliant founder of Dillon and this was the swan song of software is $11 billion, which is incredible and incredible and incredible.
But, you know, it doesn't return your growth fund.
But we're arguing two separate points, and I agree with you.
on the Figma case study and all these like fundamentally incredible businesses out there that have gotten beat up.
That's a separate point that we should circle back to.
The other point is like, do you have to swing for the fences?
You know, I go back to Arthur Patterson, co-founder of Excel, always says this thing, focus on hitting singles and doubles and let the home runs take care of themselves.
And what he means by that is if you're just constantly stepping to the plate and trying to, I can see at the series A that this is going to be a hundred billion dollar exit.
You will just over swing and you will fail.
No, but isn't that what I'm deliberately being, I'm not actually, I'm actually just fundamentally disagreeing with that.
That is like not what venture is about, especially at the series eight.
You want to have a diversified portfolio enough that you have one or two of them hit, but you want 30 swing the fuck out of this and it could be a hundred billion.
We're not here to do the singles and doubles.
I think different ways to practice the craft.
I do think the market has evolved a little bit and a single and double today might look different than it did in the year 2000.
I think what he means is like, know what you're good at, focus on founder relationships, stick to whatever your particular strategy is and just try to do that really well.
Don't just go sling it into things that are momentum chasing opportunities where you're not going to be any better than the next investor.
I think that advice is fair.
Do you not think we're all momentum chasing?
I mean, if we look at the AI entry for you guys and then the defense entry with Helsing, we're all slightly momentum chasing.
I would go back to nuance, subtlety, portfolio theory.
There are absolutely companies where it is justified to chase momentum.
We don't like to use that vocabulary, but we see a company like Anthropic and how valuable they are as a technology partner to every other company in our portfolio.
The momentum is very obvious, but the business logic and sort of the business intrinsics are also very obvious.
So does it make sense to have a relationship with Anthropic?
Absolutely.
So guilty of that.
You did the 180 round?
We've invested in a few rounds of Anthropic.
Can I know what was the first round you did?
The 180.
When you were doing that as a team...
How did you think about outcome planning that and sizing that?
I think that company and a small handful of companies in the private market today are operating on a different plane.
I think it is not bombastic to say that some of those businesses could be trillion dollar companies.
You know, people who are underwriting these rounds believe that.
So I think that is like a different category.
But the danger in this.
business is ascribing the characteristics of an Anthropic or an Andrel or an OpenAI or a Stripe to like the things that don't really fit the paradigm at the Series A.
But when you're doing an Anthropic round at 180, are you saying we fundamentally think this can be a $2 trillion company and a 10x?
Implicitly, yeah.
What do you need to see to write the check?
It's like, you know what, 3 to 5x is enough on growth.
There's never a partnership conversation where we sort of say, hey, we've built a model and squinted our way to a 3x outcome.
Like, that's just not exciting.
The reality is that...
I do think a lot of these funds revert to the mean.
If you can generate 3x net funds, that's a pretty good business to be in.
But if all you do is aim for 3x investments, of course, that's not really the math that gets you there.
If we can have a conversation about this company is special, its reach is unprecedented, its founders are very, very different, the comps for this business would be platform companies like Google and Microsoft and Amazon, then of course you want to participate in those companies in the private markets.
You said about Spice.
Do you feel better or worse to be an Anthropic shareholder post-Anthropic versus the Pentagon?
Yeah, you were definitely going to give me some spicy ones.
I can feel your compliance team just shit themselves.
They're just crying.
Look, I don't want to answer this question.
How can you not admire the founders for sticking to their knitting on and sticking to their conviction and sticking to their principles?
Now, I have no idea how this is going to shake out, right?
I mean, like...
Did you not write Dario's memo for him?
Ghostwritten.
I'm definitely not intelligent enough to ghostwrite anything for Dario.
I think this is an opportunity for, you know, a lot of these companies, they signal virtue and they believe in a world where AI is going to be a force for good.
Then there are commercial opportunities where that gets put to the test.
Can you really blame a founder for saying, I'm sticking to the mission?
I get it and I respect it.
I mean, we're seeing it bluntly play out for him in terms of loyalty, in terms of talent.
Totally.
Consumer adoption.
Mike Krieger put there doing a million a day in that new consumer sign-ups.
Yeah, I mean, they passed GPT in the App Store.
Isn't it ironic that this is what was needed for them to surpass?
No, I don't actually believe that they were doing it for that reason.
I don't think they did it as a calculated business move.
I think this comes down to...
No, I think it was an accidental bit of luck.
I agree.
It's worked out well.
I think it comes down to like ethics and principles and call me old-fashioned, but if you...
the right way, you will be rewarded.
Are you in OpenAI as well?
There are a lot of businesses today that we're in historically, which I don't know what's going to happen.
I love Sneak.
I love Mirror.
I love 1Password.
But it was done at such high prices.
And the new reality is very real.
How do you opine and think about businesses like that when you sit in the partnership meeting?
The market has gotten so humbling.
The greatest companies of three, four, five years ago, many have gotten totally beat up in the public markets.
I believe many are oversold.
I think this is where it comes back to this being a human business.
Who is the founder that you've gone into business with?
What is that founder going to do when their back is against the wall?
If you look at a sneak, I'm in Guy's new company, but he ain't there.
What do you do?
It's 300 million ARR growing 15%.
His last price was seven.
I think this is in some regards, like as the founder of the company, we lose sight of this.
That's not a great setup for people who might've invested at $17 billion, but it's a great business with a great product, with a great customer base.
You know, there will be an outcome for that company.
It is humbling relative to, you know, the valuations of the 2021 era.
But again, who is the team that you're in business with and how are they behaving?
And how are you behaving more importantly as an investor when the teams?
back is collectively against the wall.
What happens?
Do these businesses go public?
Do they get taken out by M&A?
What do you think is the route for them?
I think it's probably a good time to be in the LBO business.
I think it's probably a good time to be in the Toma Bravo, Vista, Blackstone, KKR business.
There will be homes for a lot of those companies who get themselves to a sustainable place and they will find homes.
These homes for a lot of companies will be different than what the aspiration was when the founder started the company.
That's just a reality of this market.
I totally agree.
Are you with me in the camp of when the founder goes, my conviction goes?
Now, when Andre's at Miro, I'm like, Andre's still batting.
If Andre's still batting, I'm still there.
There is unmistakably something special about a founder-led company.
Mike being at Atlassian, when I interview him, I'm like, I still feel that you've, and his passion is still there.
Never bet against Mike Cannonbrooks.
Absolutely not.
But when the CEO's there, I'm like...
It's not that it can't work.
There are incredible professional CEOs.
Like, if I could have...
If I could have Frank Slootman come be the CEO of a number of companies I work with, I bet the founders would say, yeah, that's a great trade.
I mean, there are incredible professional CEOs.
What have you changed your mind on most in the last 12 months as an investor?
I believed this thing a year ago that in hindsight, I feel very stupid for having said.
I believe that all of the generational investments in AI had been made.
I looked at...
My partner, Dan Levine, incubating scale AI, building a relationship with Alex Wang in 2016 and making that investment.
You know, the early investments in the labs, I sort of thought, listen, the bets were made eight years ago and it's too late.
And now we're all sort of.
fighting for what's left over.
That was a really stupid thing to say, and I no longer believe it.
That's probably the thing that I've fundamentally changed my mind on, both because those companies will be bigger than the outcomes that I probably envisioned a year ago, and there is still time to be a part of some of them, and because the innovation flywheel is just getting started.
We are barely scratching the surface.
When you had the scale exit for context, $14.9 billion, amazing exit.
Dan was like unwaveringly the first investor there from like, you know, the dorm room style moment.
Epic.
When you had that, so the company's got an offer for $14.9 billion.
Is there like high fives and this is awesome around the table?
No, there is an appropriate congratulations and acknowledgement to Dan.
There is a huge, loud, full-throated thank you to Alex.
And then everybody gets the fuck back to work.
It's a humbling industry and you are only as good as the next thing that you do.
How do you analyze that market stakes?
There's one that I really struggle to get my head around in a way that not cynically, not paranoid, I just don't know.
There's so many different providers that are all at very meaningful revenue scales.
Yeah.
The scale Mercos market?
Yeah.
As we said, with your Mercos, with your Turings, with your, I mean, there's 10 or 12 of them, micro ones.
I probably struggle with services, businesses in general, getting valued on like extreme, extreme ARR multiples.
You said about kind of the value of different revenue multiples.
And we've spoken a lot about Mike at Atlassian before.
There are clearly things that Mike is not able to do because he's public that private company founders like the Collisons are able to do.
How do you think?
about the benefits of public versus private today and given the liquidity so inherent within secondary markets like we're seeing with even as early as your linears where you're doing tenders for them clay has tenders and then stripes on bigger scales has obviously much more liquid markets why would anyone go public well the reverse is true too there are things that mike can do as a public ceo and the public companies can do that private companies cannot but i think you're asking the right question I mean, I think there's a reason a lot of these founders are staying private longer.
What are the things that you typically needed to access the public markets in order to do?
Liquidity for employees.
You can certainly do that now as a private company.
M&A currency and just increasing your valuation benchmarks or your valuation mark.
You can totally do that as a private company.
So I think that is all true.
With that said, I think that applies to like the 10 best private companies in the world.
Like Databricks can do those things.
Stripe can do those things.
There's a lot of companies that just do need to get public.
The trouble is those companies need to get public, but they're in the like $2 to $10 billion range.
Does anyone care about the $2 to $10 billion range?
I think you've seen this phenomenon where I would actually...
peg the range a little bit lower.
These companies that have gotten public in the like two to four, $5 billion range, and then they never really break out.
I think that's a difficult, that has been a difficult threshold for a lot of these companies to break through.
And I do think this is why you see a lot of good companies waiting.
People say, oh, it's because the investors will be underwater.
I don't think that's actually the reason.
I think it's because generally speaking, you want to go public and you want to be able to have like...
fairly clear line of sight to hitting the $5 billion threshold and trading beyond that because it's murky below that.
Is the SaaSpocalypse an overreaction or is it actually the fact that we were just bluntly valuing them far too highly on actually relatively mediocre 18 to 20% growth rates and this is a realization of that?
Fundamentally, people are valuing the future cash flows and the future terminal value of these companies differently.
And I don't think that's wrong, but I do think this has been an over rotation.
What is the most oversold stock?
We are not a part of Figma, but have a lot of respect for that company.
But I know that Dylan is a generational founder, and it's a very important company with an incredible financial profile, and it just feels, for a lot of ways, for a lot of reasons, oversold.
We mentioned the liquidity inherent within companies now as it goes later and later stage.
How do you think about when's the right time to take chips off the table?
I think you have to operate from the first principle of, What is best for the company?
Now, if the company is saying, hey, we're going to do a big tender and a secondary round that it's okay if investors want to sell, I think in those circumstances, it's generally wise to diversify.
But I think that it's got to be the right thing for the company and for the founders first and foremost.
Can I ask you, I'm sorry to be so annoyed.
I used to be so nice.
You should have done the show five years ago when I was a sweet little boy.
That's just not true.
When you look at, say, a WeWork.
Benchmark were fantastically smart to get out of it.
When you look at Lightspeed and Jeremy Liu selling with Snap, they were very wise to get out of it.
We're seeing prices so far ahead of company traction now.
It's not in their interest for the investor to sell.
Jesus, we're paying four years ahead of time.
It's in our interest.
But it's so situational.
So as a principle, do I think it's good to get liquidity back when it's available?
I do.
But it's so situational.
You use the WeWork example, like we were not a part of WeWork, but had I been a shareholder in that company when it was worth like $50 billion, I don't know a whole lot about the commercial real estate market and the office space market, but I probably would have been seeking liquidity.
Like that just feels rational.
But does it not seem rational to seek liquidity at Miro at $17 billion?
I think that was, you know, we didn't take liquidity out of Miro at $17 billion, but again.
What was Andre doing?
What was the founder doing?
What did he, you know, what was the course that he wanted for the company?
And that's like the only thing that matters.
The example I would point to is CrowdStrike.
Samir Gandhi and John Locke intersected CrowdStrike when it was, you know, there was like a million dollars of software revenue and there was a nine million dollar consulting business.
And like that was the company.
And I think they invested in 2011 at 160 post.
Now, there have been nonstop opportunities to diversify and sell CrowdStrike stock.
It's a public company.
You could do that today.
But Samir and John led the next round.
They led the next round.
They bought the IPO.
And, you know, it's a $100 billion company today.
We're sure glad we didn't take chips off the table.
The question there of, like, you mentioned obviously buying into the IPO and kind of the decision to hold thereafter.
You know, obviously, Sequoia have that evergreen vehicle, which there's been a lot of talk about.
Do you think that venture firms should...
have the responsibility of managing the book into the publics?
Or do you think it should be a distributor LPs and it's discussed from there?
Yeah, I think fundamentally we're in the business of identifying outlier founders.
If you're a multi-stage fund that gives you the flexibility to stick with some of those founders for the long run, you should definitely do it.
I think in the George Kurtz case, Absolutely worth doing.
In the Mike Cannonbrook-Scott Farkar case, absolutely worth doing.
But not every company has the mechanics to compound for a long time.
You can't just do it as a blanket rule.
I don't like public markets right now.
And I think it's just a bad place to be because you're seeing the casinoization of public markets where a Citrini report can wipe billions of dollars off.
Anthropic doing a security release impacts CrowdStrike?
I think the public markets are no longer rational.
Yeah.
To me, it's not good or bad.
It's just a different asset class.
And it's stick to what you're good at.
And I don't think we would be excellent stock pickers.
But I think we're pretty good at what we do in terms of early stage technology investing.
So I just think it's an asset class that I'm never going to be best in the world at understanding public stocks.
And I think that's OK.
Who's the best sourcer inside Excel?
Sourcer is finding.
Great companies.
Christine Esserman.
Really, really good eye for companies.
And she is relentless in getting in front of founders.
She's great.
Who's the best picker?
Andrew Bracha, by far.
Andrew is wise.
Andrew has seen success at incredible scale.
He's our best picker.
When it comes to winning, core part that we don't talk about enough, I don't think.
Who's the one you're like, okay, we need to win the deal.
We need to bring in.
I think Samir Gandhi is incredibly compelling and hits it off with founders in a very special way.
Do you think the best founders need your help?
I was going through the pillars of venture there in terms of sourcing, selecting, securing, and servicing.
And I was like, do you think the best founders actually need your help?
I think need our help is an overstatement.
I think of the role of a good investor.
There's basically these bumper decisions that come up a couple of times a year.
Like if you're a founder, your life is a bunch of little decisions and then a couple of really big decisions.
The little decisions are like, you know, design decisions about the product and pricing and should we dial up CAC and should we make this higher?
You don't need an investor micromanaging you through all the little decisions.
I do think every year there's probably a couple of like...
big decisions where having a good sounding board can be really useful.
Should we do this partnership?
Should we make this acquisition?
Do we need to pivot?
And there, yeah, I think having a good investor or just a good partner to the business can be really useful.
It's all about striking the right balance.
You like being a board member.
Yeah, I love it.
Who's the best board member you sit on a board with?
The best board member I've ever seen in action, my friend Ravi at Sequoia is a very good board member.
He was at Sequoia, now he's doing his own company.
He's done a lot of different things.
He's been an operator.
He's been a buyout guy.
He's been a growth equity investor.
But I think it's more about his demeanor and the humility with which he delivers feedback.
He has this way of sort of saying, let me politely make an observation and you can sort of choose to accept it or reject it.
There's just sort of like wisdom and humility in how he communicates, which I appreciate.
If you're a founder listening to this, what advice would you give them on how to observe for potentially not helpful behavior from a board?
There's a lot of bad board members.
I think there's generally an inverse correlation between how vocal somebody is and how helpful they actually are.
So the person who just...
has to get the first and last word in and shows up at the board meeting and has to teach you something that you didn't already know.
Like, I don't actually think that is the model for wisdom as a board member.
It's a brilliant one.
The coin box that rattles loudest has the least in it.
And another one that a fan told me the other day that I thought was helpful is like my lesson from boards is VCs are great at identifying when to hire someone and they're awful at identifying who to hire.
Your buddy is probably like the CRO of Atlassian.
That's not great for my 10 million ARR business.
That's not a good thing.
That's exactly right.
So yes.
Dude, I'd love to do a quick fire with you.
I'd love it.
So seed firm, series A firm, and growth firm that you have to invest in.
And it can't obviously be, obviously you put all your money in Excel.
Yeah.
Yeah, of course.
Seed fund, I really like the guys at Liquid too.
Nate and Matt Mulvey.
Those guys are prolific.
They have an incredible network.
They have great taste in companies and they are kind, enjoyable people to work with.
So when they send me something, I take it very seriously.
Series A?
The vocabulary on what a Series A is these days has evolved.
So I'm not sure how you would bucket these guys.
I really like the team at Meritech.
I think they have very good taste in companies.
They do some Series B and later stage things also, but great taste in companies.
And they are gritty and they hustle.
I would say it's not coincidental that Max and Alex were also trained at Summit Partners.
I really respect that part of their pedigree, but I really like those guys.
Growth.
How can you not acknowledge how successful Josh has been at Thrive?
I really admire the way that they have scaled a business that not only can initiate investments and invest across funds, but like really reflect their conviction at the late stages.
So, you know, we compete with them fiercely.
We also work with them.
I've gotten to work with Miles Grimshaw through the cursor board, which has been a great experience.
Miles is amazing.
He's great.
He is my much more articulate, intelligent VC alter ego, the other Miles.
But we have a lot of competitive respect for those guys.
He's also like a marathon runner in like two hours, 10 minutes.
This guy is like a specimen of a human being.
I could finish a marathon in two hours and 10 minutes like on a motorcycle, but it's different.
Honestly, I see miles and I'm like, oh, I need to be better as a human being.
Different strikes.
I totally agree.
I could win in an arm wrestling match.
If you could add one person to your team.
Who would you add?
This can be completely hypothetical.
It can be Pat Brady.
It can be Josh Krishna.
It can be Eli Gill.
They are going to most move the needle in our ability to win.
I'd probably try my very hardest to talk Mike Cannon Brooks into retiring from operating into being an investor.
He would never do it.
If I could go to war side by side every day with somebody, it would be Mike.
Never bet against Mike.
What about other VCs?
I agree with you.
I think it might be amazing.
I'd probably take Neil Mater.
I don't know anyone who has the investor breadth that Neil has from doing Windsurf's first round and sticking with them throughout many pivots to doing Carvana in the public markets and having that breadth of aperture.
This is actually a really fucking good question.
Or Mickey Malka.
Mickey Malka's ability to see trends so early is just exceptional.
I'm going to answer this one, but it's a really good question I hadn't thought about.
Do you ask this one a lot?
This is a really good one.
Thank you.
I saved it for you.
Thank you for that.
This is great.
I'm jet lagged, discombobulated, and I didn't prepare for this.
I think somebody who I not only have a lot of professional respect for, but somebody who I personally dislike a lot is actually Matt Bornstein at Andreessen.
Do you know Matt?
He works with Martine.
He's...
Deeply technical and very thoughtful was instrumental in their finding the cursor investment.
Matt doesn't like admitting that he also has an MBA from Harvard, but we sat next to each other for a semester at school.
I really like him.
I enjoy spending time around him.
I think he's really, really smart.
What advice would you give to someone starting their career and venture today?
I would give the same advice that Arthur Patterson gave me and says all the time to us as a firm, which is it's just about professionalism.
Arthur says this thing that anybody, any firm can be professional over short periods of time.
But his aspiration in starting Excel with Jim was to maintain a standard of professionalism over long extended periods of time.
That means respecting the process, respecting the partner meeting, respecting the portfolio review, respecting the rituals of the firm and going about the job in a professional way.
I would give that same advice.
Tell me, what deal did you not do?
that you wish you'd done in the last 12 months?
I think 11 Labs is a clear company that we wish we had been a part of.
We haven't spent enough time with the founder, which is our loss.
I think we really regret that one.
Did you try and do the 11 billion round?
We didn't.
We didn't.
You know, as I said, nobody has a perfect success rate.
Like this is one that at the next offsite, we will beat ourselves up over.
But as I understand it, very special founder, very clearly an important part of the modern AI stack.
So that one stinks.
What's worse, losing or not seeing it?
Because losing, everyone says not seeing it, not seeing it, but losing really sucks.
They're equally bad, but losing stings more.
Having had the opportunity and failed, stings.
Can I ask which loss hurts the most?
I don't know that I would characterize it as we lost, but the company that I really, really loved, the founder, and we didn't get there, was Shiv and a bridge.
We actually hosted this AI dinner a couple of weeks ago, and I was like, I'm going to manipulate the seating chart and get to sit next to Shiv because I think he's generational and very good, and I regret that we didn't get to work with him.
What win feels the best, that moment of jubilation?
There was one where I was going through some personal things and happened to be able to compete for and ultimately win the opportunity to work with Linear.
That one on a personal level was maybe the best week.
It had been the worst couple of months that I'd experienced in a long time.
There was this very surreal week where it felt like Kari might decide to raise capital.
I basically decided that I was going to go park myself in Southern California.
You know, he lives in Del Mar outside of San Diego until he basically decided, you know, whether or not he was going to raise money.
When you say park yourself there, I didn't mean as badly, but like he literally parked outside of his apartment.
No, I like got a hotel room somewhere and I would like get up and go for runs and see if he wanted to hang out and try not to bother him.
But in the event that he said, yeah, I'd love to get lunch.
Like I just wanted to be nearby.
It's a little bit creepy as I say it out loud, but at the time, it seemed right.
And I had a lot of stuff going on at home.
It was my best friend, my best friend Craig's birthday.
Craig, by the way, is the only reason I got into this industry to begin with.
He got me my first job and then my second job.
And I was flying back and forth.
go home, see my kids, go to San Diego, sit there, try to hang out with Kari, go home, attend Craig's birthday, which he wouldn't have cared about, but he's my best friend and I needed to do it.
Go back down to San Diego.
And there was just a lot coming to a boil in my personal life.
And when Kari called and said that, you know, he wanted to work together, like it was pretty euphoric.
I will always remember that week and it's been a special company to work with, but on a personal level, that one felt pretty good.
The two companies that I've never had more requests for intros to is that I had just carry every growth investor wanted to meet him before that round.
It was like, it was annoying, to be honest.
And then Lovable was really annoying.
That was really annoying.
Pre the round that Xenia did, because we were in the round before, it was just embarrassing.
I mean, like five to ten a day.
And it is very awkward.
Who else are you getting bothered about right now?
I should go see them while I'm here.
yeah there's two or three and it's so funny you see the ambassador wins where it's just like yeah you don't bother sending it to the founders because it's like i'll send you a list of names of people who want to yeah And it's even worse for me because I often have them on the show.
And so people assume that you're great friends.
I just met whoever it is when we did the show.
I just assumed you were best friends with everyone who comes on the show.
Best friends.
Final one for you, dude.
What are you most excited about when you look forward?
I think it's really important to be optimistic.
Optimists make money, pessimists are right.
What are you most excited about?
Honestly, the thing that I'm the most excited about is watching the younger team at Excel flourish.
I'm not smart enough to predict where the world is going to be a decade from now, but I can tell you that Christine Esserman and Ben Quazzo and Josh and Rohan and a bunch of folks on the team, Gonzo and everyone who's going to be mad that I'm leaving them out, we have such a talented team.
They are the unsung heroes of the firm that don't get necessarily the attention that they deserve.
I'm so excited to see what they're doing a decade from now, and I'm proud to know them.
Dude, it's such a pleasure to have you on.
It's so nice to see you in person.
Thank you so much for joining me, dude.
This is a blast.
Thanks, Harry.
But before we leave you today...
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