Most of the companies I just mentioned, their view, as they've told me, is cursor is obsolete.
What we have with the tsunami happening is a wake-up call to move to higher ground.
Don't get caught on the beach when the damn thing hits the beach.
Move to higher ground.
You really don't know the edge unless you go over it.
If I have any wisdom at all, it's because I fucked up so much and I've learned from it.
Here's the secret.
Here's the real secret.
I never left the game.
I was lucky because I was losing money every year I've been in this business.
I failed.
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Jerry, I've known you for years.
I've wanted to make this happen literally since we first had that lunch.
So thank you so much for joining me today.
Hey, happy to be here.
Now, I think it's such an interesting time because bluntly, me and a generation of investors are going hang on.
A minute is everything that we've been taught for the last five to 10 years, completely irrelevant.
And now I get to sap on your wisdom for the next hour.
When we chatted the other day, you said about tsunamis as an analogy for where we are with the AI wave that we currently face.
What did you mean by the tsunamis?
Well, the first thing I think about a tsunami is that it's harmless. when it's out at sea.
It's only dangerous when it hits the beach.
That's number one.
Number two, it's messy.
You're going to get maybe an earthquake or two notifying you there's something possibly coming.
And it's not just one wave.
There's these pre-peak waves and post-peak waves.
But there's an event coming that is more than a single product.
And in this case, it's autonomous agents.
Autonomous agents is, in my opinion, what the tsunami is about, not just AI in general.
So autonomous agents is the big wave that comes.
And so where are we now?
We're in the anticipatory period where we can see it coming, and that's why we're seeing the sassica or the sasspocalypse.
Is that the case?
I'm not a doomsayer, but I am one to say look, change is coming fast and you need to anticipate that.
You need to be on top of that.
And, you know, the idea of, oh, I can just bolt on AI to my company.
It's possibly true.
You can maybe get an exit, but being AI native and thinking that way is going to make you a better company and thinking deeply about what is going on in the communities that are driving the tsunami right.
Those open source communities that are popping up in massive amounts.
They're the ones that are going to have the big impact.
We're going to get to the bolt on AI kind of strategies, but you have an incredible portfolio of companies.
You work with many incredible founders.
What do you see in the portfolio that we touched on when we chatted before on the call on Friday that maybe people aren't seeing today when they read the news or think about investing?
If I look at real, true AI startups like E2B or Eventual or Lotus AI, GetDynasty these are all native AI companies that are up and running.
Avins, another great one.
What's happening with them is they're all using OpenClaw, NanoClaw or one of their own homemade autonomous agents.
And I think that's not obvious yet in the marketplace, because it's only about two months old.
These guys have been doing it for anywhere from two weeks to six weeks roughly.
That have brought in autonomous agents to actually write code.
That's the thing that I think is mind blowing.
Okay, so they have autonomous agents to actually write code.
What does that mean for Cursor, a 27 to $30 billion company that's raised a lot of money?
Yeah, I'll tell you.
So most of the companies I just mentioned, their view, as they've told me, is Cursor is obsolete.
That's where the product is today.
Now, my view is, yeah, but that team is really smart.
They've got a lot of money and a lot of customers.
They've got time to embrace autonomous agents, which is what I think they'll do.
And they've got shots to pivot and figure out what the next direction is.
But, you know, in the AI business, you've got to be going where things are going to be.
You can't be thinking about yesterday.
So I think those guys are going to have to quickly embrace autonomous agents.
You mentioned utilization of OpenClaw.
What do you think is the impact of OpenClaw more broadly that we're maybe not considering enough?
Great question.
Look, first thing you got to do is look at OpenCon.
Look at the community, the commitment to open source and the number of people developing for it.
I mean you can look at huge companies like OpenAI and you can look at Anthropic putting massive resources, and then you look at open source and you've got sheer numbers of people doing integrations, massive amounts.
If that community keeps accelerating and growing, we're going to see agents do incredible things that they don't have today.
When I think of an autonomous agent.
First of all, we're going to have to come up with what we call a claw stack or some form of stack for the autonomous agent.
Back in, you may not remember, back in 2003, 2004, we were post 9-11.
The world was miserable.
People couldn't afford to build websites with Sun servers and Oracle databases, which were expensive.
But the LAMP stack came out, which was Linux, Apache web server, MySQL database and PHP front end development tool.
And that led to the explosion in 2004, 2005 of websites and ultimately commerce.
Google went public in 2004 and rode that wave, brilliantly.
And I think, in the same thing with autonomous agents, that you're going to find the open source community coming out with the stack right.
Right now you've got a reasoning layer that's dominated by Claude and Codex and Gemini.
I think what's going to happen with the autonomous agents is, ultimately they're going to have an orchestration layer where they can have multiple different LLMs.
You know that they can orchestrate on and triage workflows.
They'll triage workflows and say, hey, for this part of the workflow, let's use Claude.
They're expensive tokens, but they're going to get the job done better.
And then for this other part of the work, let's use an open source model like DeepSea Lama3, whatever you know, and they're going to start from a big picture.
Maybe this is going to happen as soon as orchestration gets solid enough.
They're going to determine where the workloads go for reasoning models, which is going to be super powerful.
And my guess is this will lead to the rise of open source models more proficiently, and that it's going to lead to the rise of ASICs chips, right?
Because what's going to happen with ASICs is you're going to put the model on the chip.
You know, ASICs is going to be a lot cheaper, a lot more tunable for a specific workload than an expensive chip from Jensen.
So I think that we're going to see massive development of autonomous agents influencing open source models and ASICs chips.
From the big picture, that's a revolution.
One of my dear friends is Rory O'Driscoll from Scale.
And the thing I love about Harry is the statement, that's great, Jerry, but what about me?
Which I specialize in as a venture capitalist.
I have a shitload of NVIDIA.
And I'm thinking through as I listen to you.
Can you just play out for me that migration from Jensen chips to ASICs chips and just like how that actually plays out in reality?
Well, it's the thing that wasn't mentioned as to why he bought Grok.
He needs that capability so that he can handle A6 chips eventually, right?
I mean, because Grok, those guys know how to put memory right on the chip.
And so that's automatically an A6 chip today.
And so I think Grok is not just about handling different types of workloads and getting memory on the chip.
It's about making sure that CUDA can also support ASICS chips.
They know it's coming.
They absolutely know it's coming.
And so I think the Grok acquisition is going to help them make sure that CUDA is viable for the ASICS explosion that's coming.
If the ASICS explosion comes and CUDA does migrate with it, does NVIDIA retain their value or does it still denigrate because they have a leakage of value with the ASICS chip expansion?
Depends on execution.
This is the thing about the game, you know?
Who's going to out-execute?
Who's going to get it more?
A lot of people like to criticize Meta here and there about being behind the game, but they had the balls to say no to Jensen.
Sorry, Jensen, we don't need you.
So why did he do that?
Because he's betting on A6 chips.
No question about it.
You also mentioned the routing and the triaging between different models.
It makes me think a couple of different things.
One is that not just like a commoditization of models, where it's a race to the bottom on price and who can deliver the cheapest, fastest.
Two aligned to that.
What if then, we just see models do what we are seeing, which is eat into the application stack?
How do you think about those two elements?
To answer that question is going to be decided by the autonomous agent, not developers.
The agent is different than a developer.
If you and I are developers, we're going to go and do something based on what our experience tells us, what we think.
Okay, let's go build something here and we're going to use an ASIC chip or whatever.
The difference is an autonomous agent is probabilistic.
So the probabilistic nature of an agent is going to say I don't know which is better ASICs or use one of Jensen's chips.
Why don't I just go out and get 10 Python libraries, run them in 10 different sandboxes, write the workload and then to see which one performs better?
That's what's going to happen.
And so look for autonomous agents to have more of a say in that.
But when I think about it again, that's great.
But what about me?
Jerry, I'm investing in the agent layer today, like many other investors are.
And I'm also seeing Anthropic release incredible application layer products very quickly, whether it's legal, whether it's their co-work.
How do we determine between safe for us to invest versus in the path of an Anthropic product update?
That's why you get paid the big bucks, Harry, is that no one's going to tell you what's safe.
I thought that was the point of this, Jeff.
I'll tell you, about 80% of the investments I've made have returned less than 1.3x.
So it's the 20% that made all the money in my life and made all the impact.
Money is just a sort of batting score for how much impact you had as an investor.
That's the way I see it.
And so there is nothing safe right now.
You're going to have to watch who's going to execute the best.
Do you think public markets over-rotate when it comes to price responsiveness on these updates?
You saw Cloudflare and CrowdStrike hit like 10% on the back of an anthropic security.
Is that an overreaction?
To answer your question about the markets and they over-rotate.
If you go to Wall Street, you'll see the giant bull that's there in the statue.
It's because of a herd mentality.
And yeah, I think investors are like, hey, I'm not a technologist.
I'm just going to sit back and watch this.
Someone panicked, maybe the others are just sitting on the sidelines.
What you're seeing is less about panic selling because it'd be down a hell of a lot more than it is.
And what you're seeing is cautious on the sidelines, buyers that are saying hey, I don't see a deal here.
I'm not sure I have enough information to jump back into CrowdStrike and bring the stock price up.
So is it an over-rotation or is it just a pause where a lot of investors are sitting back saying, hey, let's get more information about who's going to be the winners and who's going to be the losers?
That's the way I see it.
Is there a parallel to a prior time where you can remember this whoa whoa whoa, immense uncertainty.
I do not know what happens.
I'm better to sit out and watch because I don't want to see Monday drop another 40%.
Yeah.
So March of 2000, almost 26 years ago, tech stocks dropped between 30 and 40% across the board.
And then if you missed a quarter, you were down over 50 or 60%.
And we lived in that malaise March through the summer.
And, by the way, We were still able to get a couple IPOs out, but at lower multiples, during that time.
And we just sat in misery until 9-11, which what I would call was the coup de grace to finish us off.
And the market got destroyed.
And we were thinking, hey, you know, we don't do dot-com investments and insights.
We're going to be fine.
Because we knew in 99 that there was a bubble, and we knew that dot-coms were going to blow up.
We said, look, it just can't be sustainable.
There's not enough commerce.
There's not enough people on dial-up.
You can't do commerce on dial-up.
There's not enough fiber in the ground.
So sure enough, there was a burst.
However, the tsunami came in, took out the dot-coms, and then took out all software.
We all went down.
We were in misery for years.
Do you think we are in that same pattern?
Do you think there will be a depressed public markets atmosphere for years?
Or will it be different now?
Well, it's always going to be a little bit different.
What's happening now is the speed at which things are changing.
Like we have this company, E2B, and you think, okay, they do sandboxes.
Great.
If you talk to most technology people, they don't particularly put much of an emphasis on differences between sandboxes.
It's just a thing to keep your agent safe or keep whatever code you have safe.
In reality, it's also a productivity tool.
And for the agents.
If you're making sandboxes for an agent, it's going to have a qualitatively different speed.
For example, about 400 milliseconds is about a time period that humans can recognize a delay.
So a lot of systems from mobile on that 400 millisecond timeframe and that's what most sandboxes are.
Well, E2B has sandboxes that respond in 80 milliseconds.
I'm like, wow, no one will ever notice it.
He said, the agents notice it.
And that's what matters.
When an agent spins up literally 100,000 sandboxes in seconds, that response time is critical.
We've spoken a lot about autonomous agents.
When you have autonomous agents, do they make your systems of record valueless or do they make them much more valuable because they have existing distribution which they can incorporate those agents into and leverage?
Which one?
Well, it depends.
I'm an investor in Carta and have been for a long, long time, and that's a system of record of sorts for stocks and it has a lot of potential.
And I believe they're doing the right thing on all fronts.
But if tokenization of stocks come and they use Carta, then Carta is going to be infinitely more valuable, right?
Because they have the cap table, they can help manage the tokenization.
However, if tokenization comes and they bypass Carta and a new system of records get built, then there's not much to say that that system of records is going to be worth much in the future.
So it depends on execution of the Carta management team and their ability to go capture the trends that are coming forward.
If you were to look at a Salesforce today, which camp would you put it in?
There's a lot of companies that sit on top of it, like Encino.
There's dozens and dozens of companies that have built on top of the Salesforce system a record.
So the real question is, let's look at their health.
Let's see how they do.
If those guys start getting knocked off one by one and enough of them get knocked off that the underlying value of Salesforce becomes less, Then you're going to say Salesforce is going to be worth less.
But in the history of companies, Salesforce is like a Mount Everest, right?
It's an 8,000 meter peak sitting there.
It's not going to melt overnight.
That thing is going to be around for a long time.
The question is, how valuable is it?
And the way to look at it, that question, the way to analyze it, is how valuable are all those companies that build themselves on top of it?
If those guys start going down, well, then you're going to see some issues.
Our job is to ascribe where we see value and where we think there will be more value.
And the things where we used to ascribe value revenue, growth rate margin have become transient slash questionable.
So in that time, how do you think about where you ascribe value?
It depends on what the timeframe is.
If you look at most software companies that are out there.
Normally when a new technology comes it sort of expands the market before it contracts, because people are already in their momentum.
They're doing what they're doing.
I wouldn't expect to see normal software companies, to see software just fall off the radar.
That's not going to happen.
I think what happens is that people get fearful and prices change.
And then the underlying quality of the business changes based on how well the management team adapts to the situation.
You can imagine some companies that have system of records that have great context could actually increase value if they're able to put that context to work with agents, with autonomous agents.
And then you have other people that, oh, They don't really adjust fast enough.
They don't really understand what the new market's like.
And then their system of record or their software declines because they haven't really moved fast enough.
What we have with the tsunami happening is a wake-up call to move to higher ground.
Don't get caught on the beach when the damn thing hits the beach.
Move to higher ground.
And that kind of adapting of your business, some people will do it, some people won't.
You said that move fast.
You've been doing this a long time.
I've shockingly been doing this 10 years now, which shows on my wrinkled face.
Really, it does.
But no, my question to you is we're seeing growth rates like we've never seen before.
I mean, zero to 100 million in revenue quite frequently or semi-frequently in some of these cases.
Is triple, triple, double, double dead?
Have we completely had growth expectations blown out of the water?
Well, think about this.
Right now, all software is eventually purchased by human beings.
Software is going to be purchased or used by agents.
And what's gonna happen is an autonomous agent becomes an employee.
You give it credentials, you give it identity, and then it's up to the agent to make the decision.
You will review them like an employee and say, hey, what did you buy?
What did you spend?
What did you accomplish?
And you will manage that autonomous agent just like an employee.
You need to prepare for that.
If whatever you got invested in, is that future going to be done and controlled by agents?
And am I in the right position for that or not?
How does the world change when you're not selling to people, but you're selling to agents?
How does that interaction change, the interface?
What changes when there's that core change in buyer?
First of all, it's never happened before, so it's happening now.
My guess is the way pricing models will work better, and it's been in process for a few years.
One of my companies Docker, has been moving dramatically toward this as they move into AI, which is a consumption-based model.
So if the agent has the access and has the authorization to use something, say a sandbox, You're just going to pay based on consumption.
The sandbox is nothing more than you're buying memory or buying compute.
And so you just open it up.
It's free.
Start using it.
And then you ultimately have to pay.
And the agent will come and tell you, hey, we've reached our limit with the sandbox company here.
What do we need to do?
And that's how it's going to work.
Going back to what we said earlier about bolt-on AI strategies, there's a lot of public SaaS companies I don't want to name any of them who are trying to move, not public, actually even kind of late private who are trying to bolt-on, who are trying to pivot.
Does that work?
How do you think about the bolt-on strategy as an effective strategy?
Look, I was just at the Olympics and there's a lot of people trying to win a gold medal and not many people do.
And so you know you can try all you want, but you better be world-class at what you're trying to do if you're going to get the medal.
I have the CEO of monday.com on the show tomorrow.
When you think about the question.
I'm not picking on Monday, but I'm saying the question of will enterprise software and will software just be entirely vibe coded personalized, customized?
How do you think about that?
Because that is the kind of eradication of a lot of their market caps.
Well, first of all, autonomous agents, and it may take a year or longer for most enterprises to actually enable and get committed to autonomous agents, but they're going to write software faster, cheaper than any human being on the planet.
They already are.
And so again, it's this thing of like if you're making your software for autonomous agents and they have a reason to use it and it's valuable great, you're going to do fine.
But if you're not making your software for autonomous agents, you're going to be challenged in the future.
Maybe it's six months, maybe a year, maybe 18 months, but you're going to be severely challenged if you still think human beings are going to buy your software.
And so we have agents buying software and we review their decisions.
I didn't have to deal with sick leave.
I didn't have to deal with entitled millennials.
I sound incredibly old school, but this is the truth.
As you know, are you worried about what happens to labor forces, given what you said, most importantly being the speed of change, is so fast.
You know, I'm glad you brought that up.
We're about two and a half years from the next presidential election.
I'm here to say that that is going to be a major issue on the next presidential election.
It could decide the election.
It'll be one of the most important things because there's no easy answer.
There's no question that anyone that inputs data into a computer that does scheduling, you know like an executive assistant or people doing marketing.
Those jobs are ultimately going to be better done by autonomous agents.
White-collar jobs.
People have been saying that for years.
I mean, this is nothing new.
The question is, when was it going to happen?
And now, with the advent of OpenClaw and NanoClaw and all the other autonomous agents that are coming, there are the direct threats happening.
First of all, not to the people with the job.
First of all, to the next person in line, the next junior developer.
You want to hire, the next executive assistant, the next marketing person?
So the first thing you see is people stopping or slowing down hiring of white collar employees that input data and use a computer.
That's the first thing.
Second thing, depending on the speed at which these autonomous agents evolve, because there's a lot that they need to do.
They've proven it exists, that they can write code and they can do anything you want from a scheduling perspective for your life.
So they're already... can replace a human being, they will.
I think that the job market's very uneven.
I think the first companies that are gonna go with us are gonna be small, medium businesses, because they're the ones that wow.
One secretary makes a huge difference in their two three, four person company.
You don't need humans doing it.
You've got the autonomous agent doing it.
So I think we have to look at what's the speed at which the autonomous agents grow in three sectors consumer, small business and enterprise.
My guess is enterprise is last.
This whole AI revolution, there have been last.
They may catch up in a year or two.
We'll see.
That's going to be what I think ChatTPT and Google and Anthropic are absolutely going to be focused on is getting their own version of the autonomous agents adopted by enterprises rapidly.
When this happens... we're gonna see dramatic change.
And I think politically, the minimal viable income may become a reality, or at least a ballot question, in two and a half years.
What does that mean, a minimum viable income, UBI?
It means that you know what you're going to go and get effectively a certain amount of money guaranteed to you every month.
And so if you're a white-collar person, they'll change the unemployment program, because no administration is going to want to sit there and say yeah, I've presided over 10 15 of the country unemployed.
What they'll do is give an option to put them into a program, And we retrain people to do something different, maybe to have a better quality of life.
If you take the optimistic view, you know those jobs that are going to be going away are not going to be jobs that gets you a vacation in Brazil anytime soon.
They're the jobs that are you're suffering at every day making a living, and you're struggling as to whether you can pay your health care or not.
And so maybe those people say I'm going to move out of the city, move out of the suburb, and maybe I'm going to move back to the country and grow food.
You know, I'm going to get this grant to do so.
There's already innovative businesses in Wyoming where they're taking veterans and giving them branches to lease, because now, with technology, one or two people can run a massive branch instead of eight people.
And so there's new things like that happening.
Does this labor displacement, does it help or hurt the Trump administration?
Depends when it happens.
In the next two years.
I think we both agree that customer support we're already seeing bookkeepers, legal would be the three and coding would be the kind of four really vulnerable areas.
I think health care may hit that before the labor market hits it because it's going to happen.
We'll find out this fall what's the impact of health care on the election.
And if it's a big impact, then you can assume that labor will be a major impact on the you know, on any administration.
When we think about the impact of agents on companies.
I had Seb from Klarna on the show and he said that at their peak they were 7000.
By 2030, they're going to be less than 2,000.
Is headcount a bug, not a feature now in companies?
You know, look, people never really talk about it, but it's all about culture.
What's your culture?
If you're looking to have a culture of A players and Steve Jobs talked about this at Apple you want.
How do you just continue to grow with A players?
You're going to have a hell of a lot more agents than people.
So it depends on what those 2000 people are doing at Klarna that are left.
What's their culture like with those 2000?
If they're all able to have a greater quality of life, have more time with the kids, maybe it's an awesome win.
You know, but I'm not there.
I'm not him.
So I can't comment.
Do you think we will have billion dollar single person companies?
It's often said, do you think it's actually a realistic?
Yeah, absolutely.
I mean, it's all about how smart is your agent?
How smart are you to deploy the agents and how well are you willing to listen?
I think the thing that's shocking is that autonomous agents work, that OpenClaw worked.
And that's why so many developers are so passionate about OpenClaw, because it's something that's working on its own without having to be reviewed.
It's an employee.
You've gone from an assistant to actual employee.
Think about that.
That's major, major difference in life.
And I think those kinds of changes are gonna be really important to notice.
I am Orlando Bravo and I'm sitting looking at my book and I've got Anaplan and I've got Cooper and I'm not picking on him, but I'm picking on him.
Right.
How does it impact me?
I need these assets to go out.
They're 15% to 20% typical enterprise SaaS companies.
What happens to traditional PE tech in this environment?
Well, let's go back to 9-11.
There was several of these traditional.
Now they're called something more sophisticated, private equity, but they were kind of buyout shops.
Teddy Forsman, who I knew, ran a great one, except in 2000 he went all in on telcos, virtual telcos.
Then it was over for him after 9-11 done.
No more Forsman Little.
And so there'll be stories like that.
I don't know about Bravo or anybody else, but there'll definitely be e-firms that end up like Forsman Little.
And then there'll be other ones that had the right bets and did the right creativity, and they'll be bigger and better and more important than they were before.
Life is basically a... set of experiences you have and the total sum of the decisions you make.
Any of these firms is about the decisions you make.
And now we're at a point in time when you need to review what your assumptions are and what decisions you're going to make going forward.
If you were to make a decision about where you would place a firm today, seeing the atmosphere and the landscape that you have, where would you choose your investing shop to be?
The problem is you got an old man here who's going to want to have it up in the mountains in Aspen or in the Alps.
That's my new thing.
I'm not like Elon or Jensen that are going to do this for the rest of their life.
I'm just doing this for impact.
I can't even imagine going out there and doing it for the same reasons I did it years ago.
It's like Bob Dylan got interviewed and they asked him what was it like for you back in 1964 in Newport?
He says, I don't even know who that guy was.
And I feel the same way.
I don't even know what that guy was like back in 1995.
It's moved on.
I was always into this business for the creative impact and to play a very small role on a team that was doing something meaningful.
So I want to do that.
That's going to be important.
But it's just a matter of having the right amount of wisdom about how the change is going to impact people and how you're going to do it.
I mean, VC firms should have their own autonomous agents.
Everybody should.
I mean, can you imagine the analytical work?
Certainly, the PE firms are all going to have autonomous agents analyzing markets, analyzing where the opportunity is.
So if I was starting from scratch, the one thing I could imagine is having incredible data.
I could vet on a new opportunity for the white space, for where these new AI companies are going to go and say wow, the data says this guy's on the right market.
He just needs to execute.
And then you evaluate not just the person, but the quality of how they use autonomous agents.
That's going to be the deciding factor for venture capitalists and startups.
We're going to be on the same level playing field.
How well do we use autonomous agents in our job?
Going back to I don't remember that and Bob Dylan and that I think actually money makes people better investors.
I've spoken to some of my most successful friends and I say has becoming rich made you a better investor?
I'm intrigued to hear your answer.
Have you become better the more money you've made?
Well, if we use money as a proxy for success, it's funny, you know, with some of our mediocre companies.
We thought about swapping out the CEO and it's like.
Well, the problem is it's a mediocre company and anybody we would put in would have to already be worth, you know, a couple hundred million bucks.
So why would they do it?
And so you would force to sort of limp along with the existing team, because they're you're just not going to recruit someone better.
They wouldn't be successful.
There's no validation unless they've made a lot of money.
So number one, it's a proxy for success.
And success is the combination of experience and validation of when and how to make decisions.
For me, there's two components to every decision.
There's the logic and the second is the intuition.
And you need the intuition.
And so the one thing that the autonomous agents aren't going to have is intuition, not anytime soon.
And so we need people.
We need good intuition to make good decisions.
And without that component, you're not going to succeed.
So, in my humble opinion, maybe I've got better intuition and that's the reason I've been more successful.
When's your intuition been most wrong and what did you learn from it?
Good question, the first thing is how do you know it's really intuition and not wishful thinking?
So that's the first thing i've.
I've learned over time that intuition was almost never wrong.
But what i was wrong was me thinking it was intuition.
It was nothing but wishful thinking.
When did you wishful think too much?
When I found an entrepreneur that I liked.
It was smart, but maybe too comfortable.
Maybe a person I liked as a human being more, and they weren't crazy enough.
They weren't really driven enough.
They didn't have that chip on their shoulder.
They didn't have that obsession.
You know, because, you know, you want to work with people you like.
And so most of the people that I liked were the ones that let me down and let themselves down.
It's the people that you struggle with, that are a little sharp edge, that are a little aggressive and that you may not like as people that are like wow okay well, but they might be the ones that succeed.
And you have to find that core of humanity in them. that you can like them and help them.
But most of the most successful people are going to be challenged socially.
Peter Fantamon's told me the best founders make you feel uncomfortable.
And I think that's very true.
Have you changed as an investor, Jerry?
Yes.
If you don't change, you die.
Changing is what allows you to adapt to the world.
I mean the most interesting thing if I look at feature stuff is Fei-Fei Li's new startup about technology, this visual representation of the world.
I mean, what she's clearly articulated is that language is a very subpar descriptor of the world.
It's just limited.
So for autonomous agents we need a new system where we can visually recognize the world, to be able to have an objective view of reality for the autonomous agent.
That's why we have poets, Because we can't really describe the world in enough detail with language.
But we can give you a feeling about it.
I think that what we have to do in the world is to definitely be aware that we have limitations in understanding it with language.
I think limitations is interesting, dude.
I often reflect on regret.
I love being in Europe.
I have family.
I make a lot of money in Europe, which is great.
But I never tried to go to Hollywood as the actor.
And I'm just wondering if I'll regret that.
What would you say to me as a wise OG?
You know, there's a great British actor I had lunch with once, named Kenneth Branagh, and he was reflecting on exactly that question.
He said he's made Hollywood movies, but he's done a lot in theater, a lot with Shakespeare.
And he said you know, I could have been more like Olivier that went to Hollywood and did Hollywood films late in life, but I didn't.
I chose a different path.
And for Branagh, I think he was very happy he didn't move to Hollywood.
He could have had that career.
And he's 65, 66 now looking back.
And he's saying, yeah, I could have been that.
But you know what?
I'm really happy I didn't do that.
So maybe you're like Kenneth Branagh.
You're going to be happy you didn't do Hollywood.
I didn't.
We started in New York.
I've never left Aspen.
I lived in New York part-time.
I never moved away from Aspen.
Jeff and I found an insight in New York City and I cover the West Coast because it was a lot quicker for me.
But Jeff and I just lived on airplanes for the first 10 years, you know, and that's how we handled it.
Back in the day, that was pretty revolutionary.
Remember?
Silicon Valley was all about people walking down the street.
There was VCs that said, I don't invest in anything more than five miles from my office.
Dude, if you can't cycle there, it's not a deal.
That was the thing, I think.
Yeah.
Yeah.
I mean, look, you choose your life, you choose your path.
You shouldn't regret it if you're getting what you want and you're growing as a person.
The most important thing looking back is what have you learned about yourself?
When I would talk to our younger partners like you had Jeff Lieberman on your show and some of our other partners I'd say hey guys, it doesn't help to get super rich early, like you have, unless internally you have a sense of self and you're comfortable with the decisions you make.
Because that's the key thing.
You know you can become super successful early.
But you've got to internalize that success, recognize where the failures are.
If I have any wisdom at all, it's because I fucked up so much and I've learned from it.
I made money very young.
And I was also an alcoholic.
And the combination of failing badly and passing out drunk many times and my mother being disappointed in the drunk son that she had actually showed me, like what life's really about.
I'm so grateful almost for failing and being like that.
Absolutely.
You've got to go.
Hunter Thompson was a writer that lived near the Aspen area who I used to love.
Hunter Thompson's works.
He said, you really don't know the edge unless you go over it.
And clearly you did.
Oh, dude, I've been over it so many fucking times.
So knowing the edge, Harry, that's what it's all about.
We've got to all go over the edge and hope to live to tell about it.
That's what gives you the sense of knowing, that gives you joy in life and gives you a sense of ease and comfort as you move through it.
When did you go over the edge?
Well, I did a different kind.
At 19, I got accepted to the United States International University in Nairobi, Kenya.
So 1977 I get on a plane, go to Europe, hitchhike around for a couple of months and then I go spend six months in Africa.
I spent weekends documenting traditional dances with the director of BOMAS.
I was out in the, you know, 13 major tribes with 76 individual clans and dialects, and we wanted to document it all.
And going out and living with these people on the weekends was going over the edge.
I mean, I ate things I'd never believed I'd eat again.
I mean, I had lived in little huts with goats, you know, it was not a pretty sight.
Dude, you've built a firm that many, and including me, would aspire to.
I just want to understand some wisdom.
Knowing all you know now.
What strategy did you do with Insight?
Or product did you do with Insight that, with the benefit of hindsight, you maybe wish you hadn't done?
What did you learn?
Oh, we hadn't done.
In the early days of Insight, the big mistake, we hired some famous guy to start Insight Europe.
And after six months, we shut it down.
It was a mistake and a half.
We were not mature enough. to do that.
And Europe was something, you know, we loved Europe early on.
Fun One had an investment called SLP in Paris.
Fun Two had a company called MetaQuattro in Spain.
It went public.
That was a big win.
We did deals in Portugal.
We did deals in the Czech Republic in the 90s.
So we thought, oh, let's do a fund.
Big mistake.
Too much difference.
Too much.
We needed to stay in New York together.
We needed to focus.
We needed to learn from each other.
Having people in Europe was too challenging.
That was a mistake that we made.
So I always say the product that we sell our LPs is the quality of our investment decisions and that reduces with remote decision making.
Do you agree or do you think that today remote decisions work just as well?
That's a function of the team.
That's a function of who's involved and then a function of experience.
You know overall, if I were to invest in a company, I would be very suspicious of the remote management, because human beings today need it.
As we move to autonomous agents in human beings, that's a good question.
You know, that's a very good question.
I don't know how the feature is going to play out, but in the past remotely managed situation I know for me cause I didn't live in New York.
As a co-founder, it was really hard on my team for me to fly in, fly out, fly in, fly out.
And because you have to make decisions remotely.
You have to sit with an entrepreneur.
You're in San Francisco and you have to commit now.
And you've got a whole team in New York.
You know, it's really tough now. being that remote guy.
If you're all local and you're all sitting in the same office, you got to make a decision tomorrow.
It's a lot easier.
So I would argue that remote decision-making is very difficult.
You mentioned momentum and the importance of momentum in some ways.
Critics have suggested that momentum was a challenge for the 20 billion fund and the speed with which it was deployed and the high prices.
Just with the wisdom and experience you have, Jerry, I'm fascinated.
How do you reflect on that fund?
One correlation you can look across all VC funds and look at their vintage, whether it's a 99 vintage or 2004, 2005 vintage.
And the one correlation you can make to success was timing.
If you did a fund in 2005 2006, you were in great shape to take advantage of the mobile thing.
That started happening in 2008 when Steve Jobs got 10 million subscribers from ATT.
That's when mobile became real.
So if you had an 05, 06 fund, you had a chance to get some of the best, most iconic companies there.
But if you start a fund in 2009, you're going to miss being early in Twitter.
You're going to miss being early in Facebook.
You're going to miss being in Uber.
You're going to miss all that.
So timing is the most important thing, whether you're early stage or late stage.
You can't apply it to just an overall general strategy.
Depends on the timing of when you did the investment.
Do you think now is the best time ever to be starting a new fund?
Absolutely the best time.
You're in a sea change.
Humans are no longer going to be the decision makers about software.
It's going to be autonomous agents.
This sea change, this tsunami, is so different than anything that's come in the past that people that embrace this new model can embrace it from scratch right now and have a huge advantage over people that have been successful with older models that don't quite move fast enough.
Because they were already rich.
They already made a lot of money.
Hard to get old dogs to move fast.
How do you feel about getting back in the game then, Joe?
You're doing this show with me.
You're talking about authorizations.
Like, seems like you're an old dog moving quite fast.
Here's the secret.
Here's the real secret.
I never left the game.
I retired from inside.
I retired from negotiating term sheets.
I retired from board seats.
I retired from internal investment committee meetings.
I retired from having dinners with LPs and answering LP phone calls.
But I didn't retire.
I haven't done a single investment on my own. that someone didn't bring me that I love and I trust.
Every investment that I've done, which is over 100, has come from someone close to me and said Jerry, I need your help to help me think about this thing.
And through that process of trying to help someone else, I end up in it.
And that's been fun because it's an experience that you're not doing on your own.
Your experience you're doing with people you care about.
Final one before we do a quick fire.
Do you believe the future of venture is like the go big or go home?
We see Andreessen raise 15.
We have Insight, a mega platform.
We have the mega platforms of GC and Lightspeed.
Is it go big or go home now?
That's the only way I played the game.
And I mean I went big on my things.
You know, when I invested in Twitter in 2009, there was 30 something.
People, no revenue.
My fund were like, are you kidding me?
It was a watershed moment that my partners allowed me to make that investment.
What did you see?
What I saw, and this is really interesting.
Like our early investments, the idea that of Twitter, which I called the status update for the world, was so brilliant so, over the top, it was far better than anybody on the team's ability to execute against it.
So I think Twitter could have been infinitely a more interesting company, But VCs got involved and created politics and they fired Jack Dorsey early and they created issues.
And the company was pretty messed up from that trauma of firing one of the founders.
And at the same time, they were very excited and the community was growing.
The community was helping it.
And for me, I saw an incredible idea that wasn't easily replicated.
And there was enough momentum to it that This was for me a no-brainer, and it was a bet that I put my entire reputation on the line.
I got Jeff Horne and Devin Parekh to jump in with me on this, and I pushed really, really hard.
We did that investment less than 30 days from the time I met the team and the time we closed and it turned out to be a watershed investment for the company and got us into lots of things like consumer and things we weren't doing at the time.
That was just because the quality of that idea was insanely great.
Did you ever have a trough in confidence?
I was lucky because I was losing money every year I've been in this business.
I failed.
I was always, you know, balanced in that I knew I was going to fail.
I knew it was going to be miserable, but I knew I was going to win some, you know, and we were fortunate to do what we did.
You know we were very, very fortunate, but failure to me was always part of my job and I had to just suck it up.
And so there was nothing that came down the pipe that caused me to lose confidence, because I'd been taking and dealing with it from day one.
Listen, I'm going to do a quick fire round with you.
So I say a short statement.
You give me your immediate thoughts.
What advice would you give to a graduate entering the workforce today, looking for a job for the first time?
I would have him go buy a Mac Mini, have an open claw and go to the job interview with his open claw.
Who is the best sourcer?
When they bring you a deal, you pay most attention to it.
Oh, that's easy.
The partners at Insight.
I mean, what we've really built is one of the great sourcing engines of the world.
I mean Mike Triplett, Jeff Lieberman, Devin these guys all just were focused on sourcing and managing their teams.
And to get through the gauntlet of Insight, due diligence and get to something that could be funded was a pretty big accomplishment.
I think that those guys were the absolute best sourcers in the world.
Who is the single best picker that you know?
They see value where others don't.
I don't want to build egos up, but Peter Fenton, John Doerr, early on, those guys were astounding at picking deals.
What is the single most memorable first founder meeting you've had?
Oh, wow.
I had the founders of Truecaller in Sweden come to Aspen.
I said I'm not going to invest in them, but they took their last dollars to get a plane ticket to Aspen.
And they came to me and it was.
This was written about in the information by Amira Frati, the story about it.
But basically these guys were nice guys and I couldn't let them down.
I didn't want to, I told them, I don't want to invest, but I'll help you.
And I ended up helping them and giving them some money and making it a successful company.
And it went public a few years ago.
And It was a great company for a number of years, but that's one I did not want to go into.
I didn't want to go to Sweden, but I liked the guy so much and they came out and asked and I said okay, I got to do it.
What's the difference between a used car salesman and a software salesman?
The used car salesman knows that he's lying.
I love it.
You've got OpenAI, you've got Anthropic, and you've got Grok.
Which would you most want to be in as an ambassador?
It depends what stage you get me a shot in.
I'm getting you a shot in OpenAI at 500, and I'm giving you Anthropic at 380.
I take them both.
I take them both, but I think for me, it's OpenAI because I got 800 million people using it.
You've got 800 million people doing it.
When you cross a billion, then you're there.
I'm not that big a Bitpoint fan.
I'm big in a couple of crypto things.
But until you get to a billion users, I'm suspicious of any consumer technology.
I get you.
But do you not think Gemini and Google can still wipe the floor with the distribution advantage that they have than this and the speed that they're moving?
They can.
And they are long-term better assets.
They've got.
If I have an autonomous agent business and I've got Gmail, you're going to have a phenomenal asset that OpenAI doesn't have.
But the issue is who's got 800 million people getting to a billion first.
I mean look, you can say there's a billion users on their other properties, like YouTube and things, but If you can convert OpenAI's chatbot to my own Jerry Murdoch autonomous agent from chat TPT which I think what Peter Steinberger is going to do you're going to have an insanely great business.
What do people not know about having money that they should know?
Very easy answer.
Money does not come with instructions.
What does that mean?
Well, everything else you buy, you get, you know, you got a Rivian, it comes with instructions.
You get an iPhone, it comes with instructions.
Money doesn't come with instructions.
So you need to learn to respect it.
It's energy.
Money is the equivalent of energy and you need to respect it.
You know you don't just leave the lights on at home and the air conditioner on your home all day long while you're gone.
You respect energy.
You treat it with respect and you use it for good and use it to make things happen.
And you don't waste it foolishly being an idiot.
You don't want to go to Las Vegas and hand out $100 bills to just random people.
Take that energy and do something great.
I mean, I don't know.
As Larry Page has said, if he had extra money he'd just give it to Elon to let him build things to change the world.
I think that if you've got money, you've got energy, you can give it to entrepreneurs.
They'll do amazing things.
You had kids quite later in life.
Yeah.
You wish you'd had them earlier.
Well, you know, it's like if you've had a fantastic life, you look back and you say it's already great.
Why would I change it?
You know, number one.
Number two, that guy, when I was younger...
He wasn't ready for kids.
All he was doing was building a business.
He was building insight.
Would it be possible to build insight if you'd had kids during?
I would have been divorced and a pretty sad character probably.
Look, when Jeff and I went out to raise money and we were getting sand kicked in our face, He was 30.
I was 35 or 36.
We both had acne.
I mean, nobody wanted to give us money.
Me, that guy with kids, I can't imagine him.
You know, I imagine he's a disaster.
What was the breakout moment?
You said that you know sand kicked in face money and then you raised 20 billion funds now in single moments.
What was the breakout?
Was it a Twitter?
Was it a... You know, it was the fact that we survived 9-11.
I mean, if you want to know...
Insight had incredible funds.
You know fund one, these incredible successes, fund one and two are still some of our best funds ever.
And then fund three or 99.
Fund was like all challenged and it did pretty well all things considered.
But the fact that we survived that collapse.
A lot of VC firms were zombies walking dead, partners splitting up people going different directions.
We hung in there.
We hung in there and survived.
That's the breakthrough moment.
What's the biggest parenting advice you'd give me now knowing what you know as a papa?
I would say your kids are always, always watching you.
So use that as an opportunity to be your best self.
Put your heart first and be your best self every moment of the day that you can with those kids.
Final one.
What are you most excited for in the next 10 years, Jerry?
I like optimism.
We sit in this incredible moment in technology in terms of development and adoption.
What are you most excited for?
There was a movie in the 1950s called The Long Hot Summer and the character Big Daddy was dying of cancer.
And at the end of the movie, things were working out with the family.
And he says, I feel like I'm going to live forever.
And I think about autonomous agents and AI, and maybe it's going to help me live forever.
That's what I think.
I actually do think it will increase longevity significantly in the next 20 years.
Do you agree?
Yeah.
Yeah, I mean.
What I've heard is, if you can live another five years, you're going to extend another five years.
So if you're, whatever state of health you're in today, if you make it five years, you're going to at least get five years on the back end.
Jerry, you're a star.
Thank you so much for this.
Oh, it's great.
And great catching up with you again, Harry.
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