E1152: Keith Rabois on leaving Silicon Valley for Miami, Roaring Twenties 2.0, IPO spree & more

In this interview, Keith Rabois and Jason Calacanis discuss a wide range of topics spanning California’s political climate, the role of macro crises in driving policy change, the impact of high‑tax states losing wealthy residents, and the dynamics of the Prop 22 referendum. They examine the significance of IPOs versus acquisitions, noting that public listings often signal long‑term durability for companies like Palantir, Airbnb, DoorDash, and Square. Rabois shares his venture‑capital mindset, emphasizing the psychological reward of backing unpopular founders, the necessity of tolerating failure, and the shift toward larger funds that require multi‑billion‑dollar outcomes. The conversation also touches on the evolving landscape of SPACs, the migration of talent and capital to Florida and other low‑tax jurisdictions, and the cultural implications of tech leaders buying sports franchises. Throughout, Rabois reflects on personal anecdotes about founders’ eccentricities, the importance of founder‑investor chemistry, and how he stays sharp after years of investing. The dialogue blends political analysis, investment strategy, and personal philosophy, offering insight into the future of tech ecosystems and venture capital.
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Hey, everybody, welcome back to this Week in Startups. I'm your host, Jason Calacanis and fan favorite of the show, entrepreneur, venture capitalist and Social media rabble rouser Keith Littleboy is back on the program for his, his is like, we do a six month check in. We just check everything, make sure he's doing okay. How are you holding up?
Surviving, you know, like it's a tough world for everybody at the moment, but, we'll get through this.
It feels like, let's start with the pandemic. It's 2020, it's December. We are hitting a peak number of cases that are being found. Testing has really ramped up. You have 200,000 people. who are being identified with COVID Sadly, we're starting to hit records in terms of deaths again, 3,000 a day, which you would expect because nobody seems to want to stay indoors anymore. And 80% of travel was the same for Thanksgiving. That was a little bit crazy. But the good news is about 100 million people seem to have had COVID. If you believe the multiples on the 15 million have been diagnosed and then you have or confirmed, and then you have some multiple of that. Some number may be naturally immune, and of course, two vaccines, 95%, 96% efficacy for the first two. And we're going to be doing 40, 50, 60 million of those shots in December, January, February. How do you look at the end game here, Keith?
Well, obviously over a medium term time horizon, let's call it two to three quarters, one should be cautiously optimistic, which is great, because until very recently, let's say two, three, four weeks ago, it was hard to see it particularly specific light at the end of the tunnel. And I think people are, you know, optimistic once they can see light at the end of the tunnel, the proverbial light at the end of the tunnel. And right now, based upon the progress with vaccines and, you know, as you point out, the level of infections that have already occurred, there is reason to believe that by the second half of 2021, you know, we'll be able to live much more normally. Yeah.
I mean, I looked at it, and I think it's going to be actually Q2, because I think there's 100 million people who've had it. or somewhere in that neighborhood. And if you look at the infection rate now, if 200,000 people are confirming a day, it's got to be a multiple. So that's 1.4 million a week. You times that by five, four, something like that, who didn't get tested, I think is reasonable. You're at five, six million, and they're doing to deploy 10 million vaccines a week. It's 15 million. 150 million people in the United States don't have the vaccine yet. It's 10 weeks of vaccinations.
I think we're done. Well, it assumes a linear ramp in supply, which probably isn't quite true. And you need two doses of at least the first two vaccines. And so the math is a little bit more complicated. But in any event, barring some unexpectedly bad development with the vaccines, you know, by July, by the summer, things should be materially and meaningfully better, even though I've seen some reports today and haven't had the time to study them carefully that suggests the time horizon will be longer. Like JPMorgan put out a report that suggests we're going to see, you know, a pretty substantial infection rate over the next summer. But fundamentally, there is some light at the end of the tunnel. People should be cautiously optimistic and careful currently, but this isn't going to be a five-year problem. It should really only be a matter of quarters.
Which is what we're seeing. I think that would explain why the stock market, where people actually make bets and put skin in the game, has been on a tremendous tear. There's a number of reasons for that. Obviously, we're injecting a bunch of money into the system with stimulus. and printing money. But you gotta think people who are investing in the stock market in companies like Disney or Uber or Airbnb or whatever the company is, they see that light on the end of the tunnel and they're assuming, hey, cruises are gonna come back, hotels are gonna come back, Ubers are gonna come back, at least for riding in Ubers as opposed to getting food delivered. So does the stock market make sense to you in that regard that people are starting to price in We're going to be out of this soon?
Well, they've priced in the secular change from traditional industries into technology stocks for a long time. I mean, starting in late March, actually early April, you could see signs where the transformation in society was accelerating from old school digital, old school analog processes to modern digital tip processes. You can see it in home selling and buying with Zillow and Opendoor. You could see it in modern versions of food, entertainment with Peloton, Zoom, to some extent, displacing real world meetings. So there's a fundamental shift that COVID accelerated. And the stock market's basically been appreciating that since maybe two to three weeks into the pandemic. The thing that's accelerated recently is more old school, real world events. I mean, you can use something like Eventbrite. It's a pretty good proxy for what people in the public markets are betting about real world events resuming normal. Because fundamentally Eventbrite's basically been the business of ticketing in person, a relatively sizable events. And that is a, you know, area that's been most affected by the pandemic where there hasn't been a massive shift to online substitutes. And so I think that's a good tracker. I, you know, Uber and Lyft, that's a bigger bat because I think there is a shift towards more sub urbanization that Uber and Lyft are less well situated for. I think there is a shift to private ownership of cars because people have concerns about sharing space with drivers and other passengers. And so I'm not sure that I'd be betting on Uber and Lyft emerging nearly as strong as they were before the pandemic because there's some macro changes in consumer behavior that are underlying or inconsistent with the long-term hypothesis of those companies.
Yes, if people aren't living in cities and cities are where there was a lot of density for it, that would make sense. And then it seems like people are moving to other cities. So it is interesting that, you know, it might be New York and San Francisco have less Ubers, but maybe Miami, Austin and other places have more because they're going to have more density. Who knows?
Well, it depends whether people move to cities where there is density or suburbs where by definition there isn't. One of the advantages of DoorDash, for example, has been they've always been focused on second-tier cities and suburbs. And so they've already proven their model works in less dense environments. And so there's a macro shift to more DoorDash-like environments than, let's call it, Uber-concentrated GrubHub-like environments. And I don't think that's going to reverse immediately. immediately after the pandemic. I think there's a appreciation basically of space. Like people appreciate and value the space they have, the flexibility of their space, the ability to have detached calls, entertain indoors with family and friends, the ability to set up a home gym, whether it's Peloton or resistance training. And that probably doesn't just go away immediately just because people get vaccinated. I think some things will snap back when people get vaccinated. I think you know, the Roaring 20s, as other people pointed out, may not have been completely accidental that it followed the Spanish flu of 1917. When we were learning American history, you know, when I was growing up, I don't think any of our teachers really linked the two, but I think there's reasons to believe that we could see some excitement energy that resembles a bit of the Roaring 20s when people feel the license and the safety to engage with other people at some scale, like birthday parties, anniversaries, weddings, I mean, There's a backlog of weddings. Like, I can name seven.
I got like five weddings that have.
Been postponed two or three times. I have currently sitting on like seven weddings and, you know, I don't know.
When they're gonna occur. All of them are gonna occur next fall.
Like August, September, October is gonna be brutal. They're gonna try, but the venues can't handle that. You know, there's only so many attractive venues. Oh, right. So there's like things like that which will cause, you know, what feels like an explosion of activity when it's safe. It's perceived to be safe. It's politically safe to have large gatherings. I think there is some fundamental shifts around conferences. Not all conferences that used to occur are going to occur. Not all sales meetings that used to be transacted by flying across the country in a plane for a three hour meeting are going to occur the same way. I think people have shifted their, or basically figured out new ways of calculating the value of their time in travel. And so we may see less business travel, but there are going to be people who want to go to concerts. There's going to be people who want to see musicians, listen to music. and in a group, dance parties, things of that sort, when it feels safe, I think there's gonna be a resurrection. And I don't know if the movie theaters, like in contrast, like ever come back, because the fidelity of a home media system is so good, and the convenience is superior versus like a concert where realistically there isn't a home alternative. You cannot have the same experience of going to a concert at home.
Yeah, that just doesn't work. But that is really interesting. I interviewed so Warner Brothers or HBO Max, that whole conglomerate, they're like, you know what, fuck it, the whole slate is going out. Wonder Woman, everything's going into our HBO Max service. So they're, in a way, that's going to accelerate their competition with Netflix. And then Disney going all in on Disney Plus and being like, you know what? All this does is accelerate them to a better model. They're going to have a better growth trajectory. When we get back from this quick break, I want to talk to you about what other sectors are going to stick and which ones maybe revert back, especially the concept of going back to an office, which I am hearing a group, one group of people, I think it's people with kids who are like, I need to get back to an office. I can't take this anymore. And then I got another group of people who are like, I'm never going back to an office. I want to know what you think the standard becomes for the big companies and startups. When we get back on this weekend, startups. Listen up. We all know marketing budgets don't grow on trees, but the good news is right now LinkedIn is going to give you a hyundi $100 credit towards your first ad campaign. Over 78% of business to business markers, B2B, rate LinkedIn as the most effective social media platform for reaching their objectives. Think about that. And why do they say that? Because there are over 62 million million decision makers on LinkedIn and they mean business. Imagine you're about to launch a campaign. It tested well, your team's happy, everything is going according to plan, except you got that one thought in the back of your head. How do I ensure the people I want to target will be in the mindset to receive my message? Well, the answer is LinkedIn. Of course it's LinkedIn. When you market on LinkedIn, you reach people who are ready to do business, which means your campaign will work as hard as it can right as soon as you launch it. LinkedIn equals business, LinkedIn equals business, and LinkedIn marketing stands out because they have tools for brand building and lead generation. You can target people based on their job title, their company name, and their location. Get that $100 ad credit towards your first LinkedIn campaign at linkedin.com/thisweekinstartups linkedin.com/thisweekinstartups /this week in startups. No spaces, no dashes. Get the Hyndi now, linkedin.com/thisweekinstartups. Okay, let's get back to this amazing episode. Welcome back, this week in startups with your favorite guest. Yep, Keith Rabois here. We did a double episode back in 2019, 904 and 905. May, he did 1057, and in August he did 1093. So, three 20 20 appearances. The fans just can't get enough of you, Keith. Everybody's like, you're. I think you're going to be, like.
Guest of the year this year. Oh, wow.
We have to get three. Three in a row.
We need a big trophy.
I'm gonna get. Yeah, I'm thinking about getting, like, hoodies or Blazers or something with, like, the number of times you've been on the Pod. Oh, that'd be cool. I like this. Yeah, like a Blazer, maybe, you know, like five episode Blazer. Let's talk about work from home because we're now getting to the point where this thing is going to wrap up in the next three, six or nine months, depending on if you're optimistic or pessimistic. But it's getting done by Q3, Q4.
And.
People like Reed Hastings are like, we're going back to the office. That's how business works. Zuckerberg's, I think, going to tell people, you got to come back to the office. Maybe some exceptions here or there. What do you, how do you think this shapes up? Do the big companies force people to come back to work or not? What's going to happen?
I think that larger companies are more risk averse and the smaller companies are more likely to be co-located and work together. They have a more creative organization. They're typically creating, fusing new ideas from scratch. And the in-person dialogue, the spontaneity, sort of combustion that leads to innovative ideas is better done in person. I think as an organization scales, it tends to be much more predictable. The roadmap is more obvious with a longer time horizon. And so it may be easier to parcel things out, you know, and basically just measure people by their productivity because you're not really trying to get that spontaneous spark. So I don't think there's going to be, my first prediction is there will not be a one size fits all solution for size of company. It may depend by market, depending upon how linear is the plan in the strategy versus how much creative energy and how how many step functions, sort of innovation does the company need or does their culture support? So I think you're gonna see a diversity there. I also think you're gonna see some hybrid models emerge that we really haven't traditionally embraced. I think more companies were either like a remote only company, like think like GitLab, which has been very successful, or full time in the office all the time, think like Amazon, Apple, et cetera. And you didn't have too many of these hybrid models where people were at scale, like spending two or three days at home or two or three days in the office. I think the emergence of a hybrid model where people co-locate some of the time and try to fuse that sort of simultaneous synchronous dialogue and spark of originality. And then people are allowed to pretty much be wherever they want another two or three days a week. I think there'll be versions of that that emerge and have it really been tried before at massive scale. So, and then I think people will watch and learn, like, which is a value proposition in terms of recruiting people, which is a value proposition in terms of success of the company, like actually output, and then there'd be another generation of people that learn the lessons of this kind of writ large social experiment of like, how are we going to organize our work and productivity in the 21st century? This is going to unleash a lot of creativity. There's unleashing a lot of, there's already a lot of creativity around tools, software, products and services designed for, for this new world order, but nobody knows what the right answer is. Personally, I'm not the biggest fan of remote only. I think there are cases where it can work and be successful. I would typically like to see early stage and mid-stage innovative companies more co-located. I'd even be a bigger proponent of distributed hubs, sort of like what Stripe has, where Square Cash App uses this, where all the designers are in New York, the marketing team and product team is actually in San Francisco at the moment, and the engineering team is actually in Australia. So they have different hubs, but you're basically tied to a location with colleagues that practice the same craft.
That's fascinating. So if you happen to find the greatest designer in Miami or Nashville or whatever, and they got a bunch of friends in design, they're the most respected person, why not make them the center of excellence?
Yeah, center of excellence model. I think there's some merit to that because not all the centers of excellence are co-located in the same geographic region. There are areas where you can find depth of expertise way outside San Francisco or the Bay Area, and you might as well take advantage of that.
Yeah, and so I guess that takes us to our next super obvious conversation, which is your recent move to Miami, which you've been vocal about, and a number of other people have already, Chervins in Miami, a bunch of other people have moved to Miami. Obviously, Austin is the other premier destination for people leaving the Bay Area. We're seeing Reno, Seattle.
Seattle's pretty common as well. I don't know if the media has been tracking that, but as far as I can tell, a reasonable fraction of people I know professionally or socially that have left the Bay Area have also migrated to Seattle.
And it's really interesting to have been in the Bay Area for as long as you were. I've been here for five or six years. And to see this golden goose, this incredible well of innovation jobs and this tax basis overnight because of the pandemic and for the mismanagement of the city to go away. What is your estimate in terms of post pandemic, what San Francisco, the city, the government and the industry looks like?
Well, it's been, you know, to some extent there's been a trend against the Bay Area and against San Francisco specifically. for somewhere between three and five years. As I pointed out publicly before, when we look at our portfolio at Founders Fund of the most important companies, and I'd measure that by our carrying value or dollars invested, more than half of our companies over the last three to five years that are the most important companies in the portfolio are outside San Francisco and the Bay Area. And that's been true. So this lags. This is an indicator of- why do.
You think that happened? Was it just that San Francisco was filled up?
Well, no, I think there's some cultural reasons. I think there's some political reasons. I actually think there's some entitlement reasons, which sort of has been glossed over a little bit recently. But fundamentally, I think there was reasons that companies outside the Bay Area were thriving before the pandemic. I think it was harder for people who were sitting here, like myself, with strong networks here, to imagine abandoning the network effect of being here. Although we were making more and more investments outside the Bay Area and watching them succeed, it was still harder to imagine ourselves removing ourselves from the center of the network. And then obviously the pandemic caused a mental shift, if nothing else. People laughed voluntarily, sometimes on a temporary basis, but for a substantial amount of time, three, six, nine plus months, and realized that actually there are better places to raise a family, better prices to enjoy living. And they don't necessarily want to come back. And if a reasonable number of those people don't come back, then the argument for being in the Bay Area, which was always that there's a network effect of talent, basically atrophies or is completely eliminated. And so it did take like a massive tidal wave, a macro shift or an unexpected black swan, to clarify for people like me that were central nodes, you know, in a social graph, you know, of the Bay Area of Silicon Valley, that, you know, maybe things are changing faster and maybe they can be rebuilt elsewhere. I don't know if I would have had that epiphany, absolute, this, you know, extraordinary one-time event. But then once you see people leaving and then you study the data of how many people are leaving and how many companies are thriving outside the Bay Area, you start questioning all the assumptions you've had previously. So let's look at a couple examples. What's probably the most interesting company in the last year? Probably Shopify. Certainly.
Yeah. In Canada somewhere.
Yeah, not either. Certainly not in the Bay Area, not in California.
I mean, but they're not even in Toronto or Vancouver. They're in.
Yeah, they're Ottawa. Yeah. They have some people in Toronto. But it's not even like the classic Waterloo, you know, engineering culture. The most interesting company I've been involved in the last year, let's say, has been a company called Fair. I, you know, I made seed investment, been funding them for like three or four years. They're going to be a very successful 10 to $100 billion company. They've never had a single engineer in San Francisco. Headquarters is technically here, but they've never hired a single engineer in San Francisco. Then I take another company that we invested in February that we profiled before our LPs this year is in Berlin. It's called Trade Republic. So another one of the most high profile and important companies in our portfolio. Similarly, Founders Fund incubated a company called Andorra in Southern California very consciously to remove itself from the Bay Area to recruit different types of people to have a different philosophy and done phenomenally well. So you just start, and then I'm not even naming the companies that are a little bit more obscure, but doing really well. Like we have one in Houston called Rig Up, New Bank in Brazil, like.
All of these companies have been thriving. Palmer Lucky left, right?
He's his company. I know where his company is.
Yeah, that's Andrew. He's a co-founder of Andrew. And so, yeah, I'm trying to get him on the pod, but you got to talk to him for me. At some point, you know how I say crazy things on the pod? I said something and I might have derided him slightly, but I'm actually a fan. and I want to talk to him about his new company because I'm a fan of Defense Tech.
Perfect. Well, we can get him or his co-founder Trey Stevens, who's a partner of ours at Founders Fund. We'll be happy to join you. Or maybe both of them. Yeah, absolutely.
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I think some of this is just a function of the pandemic allowing you to take a step back and think. Yes, the pause. It's just a pause, a reflection. If nothing else, you've had more time to reflect because there's not much else to do versus day-to-day life. Traditionally, even for me, who tries to be somewhat conscious of what I'm doing. Day to day life is meeting with founder, go to board meeting, meet with founder, go to board meeting, rinse and repeat. And so, you know, the pandemic puts a pause on that and you have more time to just say, like, is this what we should be doing? Is this the best way to do this? Is this really ideal, et cetera? And so, you know, among a variety of reasons, decided to like escape the Bay Area. And once you start escaping the Bay Area, then you're unlocking like lots of interesting ideas of like, well, where could we go? Where should we go? what's the best place to go? What are the criteria even? How should one filter things? And so that was kind of a fun exercise over like two or three months over the summer is, you know, where, where does one want to be if one isn't trapped in the Bay Area? And I think a lot of people simultaneously went through that exercise. But what's more interesting in the network effect business is the more people that went through the exercise, the more likely people were to pull the trigger. The more people that pull the trigger like me, the more other people are likely to pull the trigger. Yes.
And I've even discovered there is a, they're inducing people because if they, there is a beer of irrelevance.
You leave the Bay Area.
You don't have, like, I met Vlad from Robin Hood at Antonio's Nut House. I went to some, my friend Adao's stupid Founders Institute, and he's like, let's go drink beer with Elon at Antonio's Nut House. And I'm like, why do we have to go to Antonio's Nut House?
Place to dive, it's so dirty.
You know the place I'm talking about? Oh, of course. I used to go there at Stanford. Can we go to a place Just that, yeah, anyway, we go and this kid walks up to me. He's like, oh my God, you're Jason Calacanis. I said, yeah, tell me about your startup. He goes, we're quants, we're going to create this thing where millennials can trade stocks. I was like, millennials don't want to trade stocks. They're on their parents Netflix plan. He's like, yeah, that's the opportunity. I was like, what's the business model? He's like, free. I was like, listen, kid, are you be drinking? You want to let people trade stocks for free? who have no commitment to anything. They won't even sign a lease, get married, and you want them to trade stocks. He's like, yes. I'm like, there hasn't been a retail investor since the dotcom boom. He's like, that's the opportunity. I was like, all right, fuck it. Here's some money.
Go.
Fine. If you're that passionate about it, take my money. But that's the fear, right? You have that fear. But now you're in Miami, and every board meeting that you and I would get our asses on flights, we fly. Listen, and it would be nice. We fly business class, whatever. We get nice hotels. well, but literally every board meeting when we had to fly to them is what, 48 hours of our lives?
Yep.
Sometimes 72. It's nice. It's nice to see another city, but it becomes exhausting to do that, what, 20 times a year you were doing it?
Well, I mean, I was concentrating historically concentrated most of the board meetings in the Bay Area to minimize that. I had several board commitments in New York, but they were able to be batched together. And then in February, I added one in Berlin, which Very substantial commitment because hadn't really ever committed to doing something like that before. Um, so you could tell the quality of the company just by the level of commitment, the number of miles. Literally the, the, the time and distance to travel to board meetings was an indication of we had found the best founder we'd ever met from Europe and said like, look, if I have to get on a plane, you know, twice a year, three, well, four realistically four times, we're just going to make this work because it's that important.
Um, yeah, but Berlin's pretty dope.
Berlin's, I've heard it's cool. I've never been. It's kind of cold. My tastes are warm, hence Miami. Yeah. Now, it's gonna be a lot easier to visit Berlin from Miami. So I'm kind of excited about that. And, you know, maybe that means we'll do more investing in France or Germany or, you know, somewhere in South America. Yeah, South America definitely. New York is certainly easier, especially in a hot response to be fast responsive. You know, like it's much easier just being in the same time zone. And so I think there's opportunities that transcend just Miami, Quad Miami, although if you look even recently, just this week, we announced a pretty material round where we led a major investment of $31 million into a company called Storied in Atlanta, founded by Teal Fellows. So the quintessential type of people that would move to Silicon Valley, 23-year-old Teal Fellows, founding a company that's growing in high velocity, 5-10 years ago, they would either be told they had to start the company here or they must move it here. Yeah.
And they gotta live within, like, I don't know, how close to the Presidio Founders Fund office can you be?
Right. That was the canonical advice from all top-tier investors. And when we met the company, it was actually a feature, not a bug, that they were in Atlanta. And so, you know, Miami also makes finding investments in Atlanta at Open Door. or we basically built out our engineering team in Atlanta and had a great success. At Square, we had a component of our engineering team in Atlanta that worked on some of the more complex problems in engineering, the technically deep infrastructure problems. So I think there's opportunities to find new investments way outside the Bay Area and maybe being located in a different time zone with closer proximity will allow us to be more successful, more competitive.
If you think about it, like you have so many companies who they want to come to the Bay Area because they want to be near the locus of power and the network effect. But the cost is so overbearing for founders, you know, like for you and I as investors, like it's annoying how expensive the Bay Area is. It's a nuisance, but we get through it. But for a founder who's paying themselves a 5k a month draw and they've got 400k in angel funds, They're going to just burn through it in three months. They go to Miami. We have maybe five or six investments in Florida and they can hire people for 40 or 50 grand a year to do operations. You can't hire somebody in the Bay Area for less than 60 or 70.
No, and even if you could, you wouldn't want to because they would be so stressed out about meeting their bills and budgets. And that's not very productive for them to be focused on work. So I think you want to pay people a salary where they can actually focus. And if you're trying to be too cheap for any environment, it's really counterproductive. So I think that's true in the Bay Area, but I also think there's other reasons like you find a greater work ethic often outside the Bay Area. There are exceptions. There clearly are high tempo, high alacrity, strong commitment to work Bay Area companies. But you find on average, maybe a better caliber of work ethic outside the Bay Area these days. It's really, and that is flipped because.
When it was the 90s or the 2000s here in the Bay Area, there were VCs who there, there's some famous VCs that I can't remember, but it was like before our generation. They said they could tell if the company, maybe it was John Doerr or someone like that, they said they could tell if the company was going to succeed when they drove past the office on a Saturday or Sunday and they look at how many cars are in the lot. lot.
Yep. Well, you may have seen Mike Moritz has published a few years ago a couple essays in the Financial Times.
Yeah, really good.
Comparing Silicon Valley to China in the work and particularly highlighting some of the work ethic degradation. And I think he made some of those points and they're pretty stark. So I'm excited to find people that might be more tenacious with more grit, with a more consistent work ethic than on. Less entitlement.
Yes, definitely less entitlement.
Now, there's one perverse argument that actually a very smart founder was texting me yesterday that's pretty positive about the Bay Area. And he basically said, look, the people leaving the Bay Area are all the people you want to leave the Bay Area because the quality of life in the Bay Area is actually very mediocre. And so they're leaving to Denver or wherever and, or Austin or wherever. And the people that are going to suffer through the quality of life degradation here are the people that actually really are ambitious. And see why you may wind up with a positive skew. That's actually the best most intellectually honest argument of heard for being, being sort of positive about the future of San Francisco.
So basically, if you're a masochist and you're willing to deal with the pain and suffering of a three thousand dollar apartment that gets broken into and your car windows get broken and you have to step over people who've overdosed and who are being given a, you know, being put in an ambulance because they're overdosing intentionally.
Yeah, you're probably sufficiently crazy to start a company. So that was his argument. And I was like, actually, you know, there's something Internal logic there. It's actually not at all wrong.
It's intellectually, it's intellectually, it's the best.
Argument in three months I've had with anybody about the potential of the Bay Area. I was like, oh, that makes actually some sense.
But I'm having the same exact experience you had, which is, I hate it in person. I like meeting people, you're social, I follow you on your Insta, I see what's going on. You like to go out, sometimes you hit the club a little bit, you like a little dance music maybe once in a while, you got to have dinners.
And you're way overrating my social life. life in my.
All I know is that once you come up on my Instagram once every.
Six months and you're out of club. That's right.
I actually go out about once every six months. So the other time is two times a day going to Barry's boot camp.
That, that's true. The Barry's is definitely something I do.
Wait, is there Barry's in Florida?
There's three locations in Miami, two very conveniently located. And even better, they don't have London breed in Miami, so they're actually open.
They're OBS London. I mean, talk about insanity, but I had the same experience you had, which is, okay, now I'm stuck in my house. It's great that I get to spend time with my family, but I don't need any alone time. That's not who I am. And I am so much more productive right now because I am popping off a board meeting with a New York company, with a Miami company, with an Austin company in the same day. and when you're on Zoom, people just get to the fucking point, I find. Like, these long meandering board meetings with the board dinner and the pre-board lunch and the next day, it was like a two-day or three-day thing, every board meeting when you went somewhere. It has been an amazing year for IPOs, and I bet you wish you were in on some of those best performing ipos of 2019 and of course 2020. With our crowd, accredited investors can invest directly, easily, and most importantly, early in these great startups. Our crowd investors have benefited from companies going public like Beyond Meat or companies that have been bought by Intel, Nike, Microsoft and Oracle. Our crowd is an investment platform and they have investment professionals there who leverage their extensive networks to review some of the most promising private companies and startups in the world. OurCrowd's investment team has already invested hundreds of millions of dollars in over 200 companies with dozens of exits. Accredited investors can participate in single company deals for as little as $10k or one of OurCrowd's funds for as little as $50k. Today, you can join OurCrowd's investment in BlueGreen Water Technology, a startup that keeps our water safe. Global water supplies are under attack from toxic algae blooms making some water undrinkable. Blue Green's proprietary EPA approved technology eliminates the toxic algae poisoning the world's water resources. You can get in early on Blue Green and other unique opportunities at Rcrowd.com/ twist, Rcrowd.com/ twist. If you're an accredited investor, go ahead and join for free at O-U-R-C-R-O-W-D.com/twist and review their current deals. I think I'm gonna get in on this one. Blue Green Water Technology seems like a really interesting one. You can review all those current deals with no payment involved until you decide to invest. So you can read all the deal memos for free and get smarter. You might as well go do that.
Right now, ourcrowd.com/twist while you're listening to the show. I think that's true, that there is one big downside. And so I think for information sharing, a Zoom board meeting is incredibly effective. and efficient, like for all the reasons you just identified. I think though for a complex debate about a controversial topic, a Zoom call, whether it's an executive team Zoom call or a board meeting call, just does not work because there's just enough lag. Like when you're having a vigorous debate with someone, it's the handoff in the comments from a variety of people that gets stitched together into an interesting dialogue. And that's extraordinarily difficult to do on Zoom. So I actually find myself as a.
Fair- you- got an example of one that you can sort of anonymize a bit of in a conversation that didn't go well over Zoom?
Yeah, actually what I actually wind up doing truthfully in Zoom-based board meetings is I'm actually quite passive viS-A-Vis the level of participation I'd probably have in a real world board meeting because I actually take sort of stock before I make a comment of, is this point sufficiently succinct enough that if I make the point, people will understand it without having to go through several iterations and distracting 15 people. Whereas in person, you can kind of look at people's eyes, you can time the comment correctly, you can get in and out of a conversation pretty artfully. And so I've just found that I learn a lot through board meetings sometimes. on Zoom. But in terms of driving a conversation, debating something with the team, really highlighting something a little less intuitive, I'll do it maybe at 30%, 33% frequency that I would have in a traditional board meeting. So what I'll do instead, fortunately, is I typically spend time one-on-one with the CEO anyway. And in so far as I have feedback that's a little bit more complicated. I'll actually just provide the feedback either before or after the board meeting directly. And there's some virtue to that anyway, but there's some disadvantages, which is the other board members don't hear it and the CEO doesn't hear like a stereo surround debate nearly as frequently as they might be accustomed to or what might be ideal. So that's a disadvantage. So when we do return safely to real world board meetings, I do intend to, whether it's getting on a plane or whatever it takes, to attend board meetings in person, not by Zoom, as soon as other board members are also there. Yeah.
It's really hard to have that, like, you can't have that quick side comment or just like, you know, just as an aside bank.
It distracts people, becomes a major candidate. I actually find the same thing is true of investing. So obviously I prefer to invest as early as possible in seed rounds, you know, before there's even a product, certainly before there's metrics. And it's still easy to do on Zoom for people I already know. which fortunately there's a reasonable number of people that are in some concentric circle of activities and investments I've already made. However, meeting someone from scratch and trying to assess them is extremely difficult on Zoom because you can't have this dialogue, the really fast interactive dialogue, which is allowing to see the person's processing speed. What do they focus on? What do they get? What do they grok? What do they not get? What questions do they ask? Extremely difficult to have that fast-paced conversation. on a Zoom call. And so I'd like to get back to real world first meetings with founders of seed companies, but it's going to be difficult in the Bay Area because it's going to be politically unacceptable for at least three, four months.
Yeah, you can't have meetings, you can do a walk and talk, but you lose that ability to sort of, I call it like in tennis when you're volleying, you know, or ping pong, you're volleying back and forth and you kind of get a vibe for the person, I can't get it on Zoom. What I can get on Zoom is if they've got really good metrics, they got their cohort data, we can drill in, we can share a screen. My little secret that's been working well because I do like to talk and have vibrant debates and conversations in board meetings or everything is I'll just slide into the chat section of Zoom, which I know is ephemeral and goes away, and I'm just like, you know, quick QQ, quick question, and I just put it there or just QC, quick comment, and I just put in a little quick comment, this sounds great, or you might want to consider looking into this, or here's a book I read about this, and I just leave it there for the founder. And then the founder who's leading it will say, oh, Jason, you commented on that book. Yeah, I actually did read that, but it doesn't break their rhythm.
No, that's a smart idea. I actually think that's a really good, like, sort of pseudo best practice for like Zoom-based board meetings with multiple people. I think the volleying metaphor I really agree with. I think that's the best metaphor I've described. of how typically I would like to have conversations with CEOs, potential founders, and I found it incredibly difficult on a Zoom call. It's unfortunate. Even a walk for me is not the best because I like to take notes and it's really difficult on a walk. Also, like to watch people's expressions and eyes and really can't do that while you're walking. So walks for me are very effective for people I know well. because I can tell the things I can hear in their voice and I expect certain things and read between the lines. Same thing for boards, where there's a board meeting where there's a pre-existing relationship among all the board members. It's not quite as bad on Zoom versus you're working with a new executive, a new VC, somebody who doesn't have these deep social ties. So there's some board members who I've worked with over a decade. And I think we can have a dialogue with the CEO on a board, on a Zoom call relatively successfully because we can kind of read each other pretty well. And we may also use the chat function. Sometimes we screw it up and send it to everybody. Be careful.
Yeah, sometimes you just send it to one person.
Yeah, I haven't really done it badly yet, but I've definitely been in board meetings where it's been.
I think like the Jeffrey Toobin, like nightmare scenario is like one nightmare scenario at Zoom that is just insane. But there is a more practical one.
Yeah, the more practical one is like, oh, this board deck's awful. And they just sent it to Andy.
Oh my God, why are growth is flat? Didn't he, what are they doing here?
How come they can't get this graph to go up? I've definitely watched a few of those. Good.
It's like, oh, we're going through our fifth sales leader in seven years. Wow. What does this tell us about the CEO?
Yeah, I did. I made a comment yesterday or today, last week, that went to everybody, but fortunately it was the most innocuous thing ever.
Thank God. You're like, have you seen Queen's Gambit?
A little bit like that, yeah.
Yeah, that's, I mean, that's the other problem I'm getting the sense of is like, are people actually, what actually are people doing when people are talking on Zoom in the other windows on their screens?
That's, I mean, that's part of the problem too, is just because of that, you know, distraction. like when I go to a normal board meeting, I just put my phone upside down on the table and don't pick it up. And sometimes don't pick it up for three or four hours, depending on the pace or whatever. I put it on airplane mode. That's my little secret. That's even better. That's even better. And, you know, in Zoom, nobody does that.
So I think the concentration level also decays to some extent.
Yeah.
But then you add the multitasking level. So when somebody's like, hey, you know, blah, blah, somebody else is, like, looking at the company page and, like, literally, I was on a board call and they had fired somebody. and they had taken documents with them or some bullshit like that. And then I was like, you know, I just Googled him and he's updated his LinkedIn and he's working at a competitor. And they were like, it was almost like real work detective work while we're on the call. Like, holy shit, this guy stole stuff and he's working for a competitor. Time to drop like- yeah, there are.
Definitely are some activities that you can do. Like, for example, I think sharing a screen on a Zoom call or board with a board member or executive team can actually be fairly effective because unlike when you're presenting and you kind of have a base presentation, if you want to change and show someone some actual data, it's much more artful and less distracting when you're sharing a screen to just pivot to a different page and then have everybody see exactly like what cohort data you're looking at. So I found that to be pretty effective, but there are a lot of downsides.
It's nice because you're six inches away from or 12 inches away from like the deck as opposed to it's being projected on the wall. You know, so you kind of get this more intimacy on the numbers. Let's talk about the IPOs that are going on. It's been pretty amazing to see the world we grew up in over the last decade where nobody would go public. Airbnb and Uber taking their time, taking their time. Yuri Milner and everybody else throwing late stage money. Don't go public. and then lo and behold, my bestie Chamath and now Reid Hoffman and Mark Pincus and everybody else is doing SPACs. And now there is a way to get public quicker. You did Open Door, right? And was that with Chamath or?
Yeah, so Chamath and Adam Bain really worked on bringing Open Door into their SPAC, which, you know, is a transaction that that hasn't technically closed, but you can sort of see the market cap because you can buy the whole thing. Yeah, IPOB. It should close hopefully next week. And it's been a very successful experience both working with Chamath and Adam and then B just the public market reaction. I think as of today, we're probably valued at like 13, 14 billion. So Chamath got a great deal at five.
Yeah. And when you go through this process, I don't want to talk specifically about anything that would get you in trouble, but just talking about the SPAC process, putting aside open doors process, just SPACs in general, keep you out of trouble. Make sure you don't disclose any, you're not supposed to, but tell us about the process and the window of companies that it's best suited for rather than a direct listing, like say, Spotify did or waiting like Uber and Airbnb did like waiting 11 years.
So let me start with first principle. First principle is I think waiting was always terrible advice is one of the worst pieces of advice that anybody in Silicon Valley has given for the last 15 years. And fortunately, some of the companies I've been involved in didn't listen to that advice. I think realistically only Bill Gurley and me were like sitting publicly critiquing the people dispensing this advice. I believe strongly that companies should go public as almost as fast as possible. I wrote a whole chapter in a book that I highly recommend to founders called High Growth Handbook published by Eliot Gill. The whole entire chapter is why to go public, why to go public as fast as possible, and why everybody doesn't do that is like really sacrificing their company's potential. But that was a controversial view. Fortunately, in the last six months, it's become a very conventional view. SPACs are a process really for companies that suddenly realized that Keith and Bill Gurley were right and hadn't really prepared for traditional IPO, whether an IPO or direct listing, and they wanted to accelerate the process and find a way to do that. A SPAC can be a good vehicle to accelerate the process where the management team hadn't really prepared properly. That isn't the really best feature of a SPAC, truthfully. The best feature of a SPAC at the end of the day is that legally or a hardcore technology company that's really innovating on a deeply technical solution, they can guide years into the future about the revenue potential of the business. Whereas through an S1 process or traditional IPO process, it's extremely legally precarious/virtually impossible to guide future years revenue. And so as a result of that, if you have a breakthrough technology that will have a market, it's much better in many ways to be able to convince and articulate the market size to potential investors through a SPAC process than you would be able to do in a traditional IPO. Now, that said, it's not that different than a private fundraising. People have always done this in private fund raisings. So when people pitch us at Founders Fund, even when they're reinventing a rocket or reinventing manufacturing a space, reinventing genetic sequencing, they're talking about the revenue potential in the slides in the presentation. So this is very similar to what you'd see in a private fundraising process. It's just now possible to do it publicly. Right.
And it's, these are going to be earlier companies. We think year 5, 6, 7 is the, is the window for these, which is what it used to be, right?
I mean, before our time, but isn't.
That what happened in the 90s?
Well, the 90s is actually last. It reduced to like 3, 4, 5, which may be a little fast. Yeah.
5 million, 10 million in revenue sounds.
A little too young. That might be a little bit the low end, but somewhere between 4 and 7 feels pretty good for a high growth company that has predictability and it has medium scale. To me, medium scale is somewhere between 35, 40, 50 million in revenue with predictability where you can talk in an educated and accurate way about the likely revenues one, two, three, four quarters out, then you should be a public company for the most part.
But they don't have to be, correct me if I'm wrong here, absolutely certain and robust with 10 billion in revenue like an Airbnb or an Uber or something where you've got this massive footprint so that people can have an opportunity to have their public shares accelerate. When people bought Uber or when they buy Airbnb, some of these companies are very fully richly valued and there's not as much growth available to those retail investors.
Well, to start- Probably speaking. I mean, that's both true and false. I mean, like for example, if you had bought Shopify in the public market, you'd be very happy with your returns. If you'd bought Tesla in the public markets, basically anywhere along the way, be phenomenally satisfied with your returns. If you'd bought my old company, PayPal in the public markets, oh, my God. You know, as someone pointed out, like, well, even, even like recently, like, I, I, to show you how much I haven't touched my LinkedIn profile on my LinkedIn profile, it cites like PayPal being worth 40 billion. It's only worth like 6x that. It's the last time I edited my LinkedIn profile. So, you know, so like, there's lots of opportunities for growth potential in the public markets. So I don't know if that's a real reason to prefer a SPAC. I think some of the other reasons are much more structural and fundamental, especially from a founder's perspective.
When you lower the bar of entry, you make it more fluid to go public. You also get, let's face it, some people maybe who shouldn't be running companies are going public, putting products out there. We saw Nikola, Fisker, basically anybody who does anything that's in any way tangential to what Elon has done is able to ride his coattails and say, we're going to be the next Tesla. And you might have some product being put out there that, let's face it, these are not great companies or they're massively speculative. How does the, are you concerned the SPAC space, you know, for every Chamath run or Reed Hoffman and Mark Pincus run and, and people who are super qualified, you might have this like, kind of, I don't know, low quality inventory maybe is a generous way to say it. Yeah, sure.
But there's been low quality inventory available in the public market for a long time. Whether they're large market cap, mid market cap or small market cap companies, I don't know if that's new. And I think there'll be a flight to quality. I think there'll also be a way of gauging the reputation. I mean, one of the things you can do with a SPAC is the SPAC sponsors are sort of endorsing a specific valuation. whereas the old school investment bankers are really not doing anything truthfully. And so it's not like if you take your company public through Goldman Sachs and I'm not picking on Goldman Sachs, particularly just the quintessential investment bank, they are not really doing anything. They're not taking real risk. They're not putting their brand behind your valuation. Whereas a SPAC sponsor is explicitly saying in a memo form, We believe Open Door is worth X. Here's why. Here's our logic. Here's our investment logic. so I think there'll be sort of a sorting, a reputation sorting and ranking of SPAC sponsors based upon both their historical performance of other things they've sponsored in the public domain, and then B, the quality of their work because their work is going to be public, their intellectual work is going to be public for everybody to consume and debate and critique.
Yeah, that makes total sense. And then going back to the movement of capital and the movement of folks It's been amazing to watch Florida specifically, the mayor is engaging on Twitter as people are asking questions about, you know, which city they want to move in. And the mayor of Miami is literally responding to investors and venture capitalists at the same time that California folks are telling, you know, Elon Musk to fuck off. You have the mayor of Miami doing that. And then I just saw an alert come up in my feed that Goldman is planning on moving asset management from New York City to Florida. When we look at the taxation in the United States and talent moving, what are your thoughts on what happens to the New York City and the California's?
Well, I think this is a very healthy thing. I think competition for government policy and quality government is a very good thing. It's called voting with your feet. This is an old concept that Alexander de Tocqueville wrote about, the founders in the Federalist papers wrote about. So this is like centuries old as a concept. It's just actually much more feasible right now. It's also happened typically in Europe. Europe's always, because of the proximity and the cultural similarities of some countries, had a bit of this sort of amenable ability to competition by citizens voting and immigrating. Whereas in the United States, at least by industries, it's sometimes been more painful and challenging But with new world order and a transnational society driven by the internet, I think it's a lot easier and you're going to see states and cities are going to have to compete for the best people for the most talent. So it's very exciting that the politicians, whether the mayor, the governor, the secretary of commerce in Florida, they want high paying jobs. Most people actually really want technology. Technology is extremely popular outside certain pockets of California. Yeah, they want the jobs, they want the growth, they want the high paying wages that technology companies can afford, and they want the innovation because innovation benefits the citizens around them. And so it's refreshing to see this. This is true in Texas too, maybe not quite as publicly, but privately. The governor of Texas is quite supportive of entrepreneurs, VC is moving there. I'm sure that the culture there and the environment politically is much better than in California and San Francisco specifically. But in the modern world order, you see like the social media presence of politicians is an important way that they compete for votes, attention and money. So like you see on the Democrat and liberal side, you have someone like AOC, who in many ways is an obscure, you know, 28 going on 30 year old who has like crazy views on most things, is pretty influential in the Democratic Party because of her ability to proselytize really and frame things through social media. And so you're going to see other politicians competing on that that basis as well. I think this is the future. And I think you'll see it internationally, cross borders. But this is a very healthy positive thing. I think it is going to be difficult for very high tax jurisdictions to contain their talent. I mean, basically, this has happened with athletes. I know you're a big basketball fan, but for a very long period of time, athletes, when they become free agents and decide which teams to go to are very consciously aware of the various tax rates in Canada versus United States of this state versus that state. Some states have tried to tax visiting athletes to try to avoid some of that sort of advantage. That's hilarious.
So an NBA player who's situated in, for the San Antonio Spurs, Houston Rockets, or Dallas Mavericks is paying 13% less tax or whatever it is, more probably 15%.
Well, if you talk to any other agents, this is a very important important consideration of both where they prefer to go to and how they negotiate their contracts. So for people who've had mobility and are, you know, clearly recognizable Talent where there's options, they've always competed on this basis, and you continue to see that, you know. So I think many people are doing the LeBron James thing of taking their talents to South Beach.
Yeah. Steph Curry would be making, like, five or 10 million more a year if he was in Miami and then Just amazing to see there was Mayor Francis from Suarez from my hammy was getting into it with is it Delian, the guy over?
Yeah, Delian is a principal of ours at Founders Fund.
Yeah, and he loves to mix it up on the Twitter. You guys have a real mix it up culture, I guess. I think you can get in trouble for that at another firm. But he was basically saying how, you know, they don't have, There's an issue with non-competes, I guess, in Florida. I didn't realize they were enforceable in Florida. He's like, yeah, they should make those non-enforceable. And the mayor's like, yeah, that's state laws. Let's discuss it next week.
It's like, oh, okay. And then you have- yeah, the history of Silicon Valley was clearly affected by California's historical legacy of non-enforcing non-competes. If you read any of the histories of Silicon Valley, versus Massachusetts and Boston, which had really dominated a technical innovation in the 1950s and '60s. So I think this is a legal regime that could be changed, should be changed. I do have some questions on whether it's still true, is still as important. So as I mentioned, one of our best companies is in Germany. They have a lot of non-competes. I don't know how it works in Australia or where there's been a lot of successful companies at last year. Afterpay, et cetera. I don't know, you know, in, in, in most of these European countries, I think are actually pretty stringent. So there has been a lot of success, I think, Audie and or Spotify in markets where there are non-competes enforced. So I totally buy the historical argument. I've read books that are, you know, basically almost exclusively dedicated to the history of Silicon Valley and, you know, non-competes are clearly influential in that history. But, I, and I think it's obviously a good thing to change the law in Florida and other places. that currently, Epstein Theory could enforce a non-compete, but I'm not sure it's like indispensable as or as indispensable as it was in, let's say, the 1970s.
Yeah, it would be really interesting to see if a company even asked, because, you know, employees are getting more sophisticated now. They know what they're signing on the high end employees. So sure, exactly.
Executives are definitely familiar or another to critique this view is Washington State actually does enforce non-competes. And last time I looked, two of the four most influential tech companies in the planet are in Washington.
Yeah, I mean, and I think Microsoft and Amazon have some basic rules of the road around this. Like they probably limit your non-compete to a specific period of time, to a specific vertical. And if you are going to enforce it, you have to get paid, I think, is the thing.
And they actually have sued people and tried to sue people. So, you know, with that example of Washington, you know, being a great tech corridor, really. Yeah. I mean, Zillow's based there. Travel companies like Expedia, they've clearly had a lot of success with technology in Washington. So I'm not so sure that it has to be reformed, but it certainly would be a good thing from my perspective. But I'm less convinced that it's indispensable.
Yeah, I remember the last time I remember even reading about, I was so fascinated by this in my early career when I was a journalist. I researched it and tried to find examples. And the example I found, the most prominent example that went to bat was a hairdresser who had signed a non-compete. She couldn't work within 50 miles of the current hairdresser. And so she literally had to, when she left the job, get a job, get a job over 50 miles away, and it was actually enforceable. I was like, yeah, that's crazy.
That's crazy.
For a hairdresser, like how vindictive and stupid are you? So when you, on a go forward basis, how do you think you'll be able to meet founders? And do you think it's still going to be the Zoom culture for the early call and then the relationship building on the other end. Have you started to think about that? Because I certainly am thinking about- yeah. How do I go back?
I don't know. I mean, I prefer to do more real world meetings for the reasons we discussed, but I actually think founders are starting to enjoy the Zoom call because they can create efficiency in their process, which yields a competitive dynamic. So typically, the proverbial trip to Sand Hill Road, it was very difficult to schedule and align various firms and partners so that you could meet them all at the same time and all that. It just never really happened. Maybe you could get half your VC pitches on the same schedule, but the other half just like logistical constraints. So in the Zoom financing post-March, everybody raises money in the same week. And it creates a very, positive feedback loop for the entrepreneur where they get more term sheets, higher valuations, faster process. And so I'm not sure the founders are going to let us go back to real world meetings as a default. But I strongly wish, you know, I hope and hope that we can.
What are the reasons?
For later stage money at companies, I don't think it'll matter as much. I think at that point you are looking at like more like metrics, financials, spreadsheets, and that can be you know, remotely.
What about LP meetings? You know, when, and I don't know if you were involved in Founders funds fundraising process, and I know that they have, I think you guys just kind of say we're doing a new fund and it comes in. I don't even know if Brian Singerman's got to go on a roadshow anymore. Right. But what are LP meetings going to be like? Because I, I've talked to people who closed funds during this and they said it was amazing because, I mean, when you go ask an endowment or somebody to give you 10 or 50 or $100 million for your fund, it takes a visit with a team and you meet with their team and now that's occurring over Zoom too.
Yeah, I mean, so we raised our last series of funds prior to the pandemic. We did do our first annual LP meeting that occurred post COVID in October and we did like a high production, pretty thoughtful approach to it. I think people were very satisfied. I think our LPs were actually delighted with both the content, the quality of the content, the quality the production. And they did find it very efficient because they typically have to travel. And so I think all around it went very well. I don't know if we really want to do that every year. It might be good to have a mix of, you know, sort of a remote LP meeting and an in-person one where you can have a cocktail party, chatter, you know, like the kind of soft gossip stuff. Like, like, so there's thing, there's benefits that we didn't really have. This is a very formal. very efficient process. It got people very educated about our portfolio, about our investment strategy, about what was working and what we thought about the future. But I'm not sure that it's a complete substitute and that we'll stick with it permanently. Maybe we'll mix it up a little bit, one year a little bit more remote, one year maybe a little bit more in person. I don't really know.
Prop 22 got voted down. and Newsom is on the brink of being recalled based on the number of signatures. I'm not sure where the number is at today, but there's, they were at 800, 000 or something and they needed a million and change to actually recall him. Does it look like the hysterical, insane socialism in California anti-business is getting maybe some pushback?
Well, the Prop 22-1, I think is a function of pushback. I think had that gone the other direction and Uber, Lyft, DoorDash, Instacart either suspended or significantly curtailed operations here, I think normal American citizens of California would have been furious and they would have taken out that wrath on politicians. But because the court stayed the impact until there could be this referendum, and because actually these companies decisively win the referendum, I think that has alleviated a lot of pressure from normal people not being deprived of services that they depend upon and actually love and or depend upon. On the recall, that's going to be interesting. I think it will take an earthquake like some catastrophe or some unexpected incumbent being voted out of office. before there's a significant change in the political culture in California. So if Gavin were to get recalled and to lose, that would be a dramatic earthquake. If he runs for re-election in 2022 and loses, that'd be a dramatic earthquake. Things of that sort. Then everybody says, Holy cow, the sky's falling. We need to change our behavior. But outside a macro crisis like that. So in New York City where you grew up, we had this macro crisis around crime in the 1970s and '80s. New York was completely unsafe. Like my parents wouldn't allow me to take the subway past 5:00 p.m. when I was growing up.
Oh my God, it was seriously dangerous. You get off the wrong stop, you die.
No, it was absolutely ridiculously dangerous. And the city was in decay. We did have like blackouts and like ridiculous things that only third world countries in California have. And, you know, we, it took that level of crisis though before people were willing to vote for a Republican for mayor. and as soon as they did, though, everything got better very fast, like crime, prosperity, everything changed. And so I think California is going to have to go through, unfortunately, more of a crisis before there's an epiphany, and that may lead to a better future.
Yeah, it does seem like having all of one party running the show leads to a certain direction. And it's really amazing how out of I think the people in office are with the actual desires of the citizenry. I mean, people in San Francisco would like it to be a law and order city. And you have this person, Chesa Boudin, who just does not want to arrest the fentanyl dealers. And you could be completely compassionate about, you know, drug related crimes and still have the common sense to realize fentanyl is a entirely different level of death than smoking cannabis or taking mushrooms or whatever is legal in Oakland. They won't even arrest basic fentanyl dealers.
Yeah, I mean, that's what I mean. I think you need a macro crisis before there's a transformation. And that's unfortunate because it's a very crisis by definition is very painful for everybody involved. But I think that's when things will start getting better is when there's a revolt. The revolt is generally caused by things being like Just completely intolerable.
Do you think that people leaving and losing the tax base has got a chance of being that? Because I'm seeing a lot of people I know who pay a lot in taxes leaving. And then I see the cost and the budget keeps going up. So my basic knowledge of a P&L is like, if you don't have the profits from the taxes and your costs are going up, this could, the burn rate could get significant. Is that going to happen, you think?
Yeah, no, I, I, I, I think because because of COVID some of this is masked and the state's going to have a hard time predicting it correctly. There's a lot of these people are leaving it but aren't coming back. And then hence the tax revenues are going to be very different. And California, because it has such a high tax rate, a lot of levied against wealthy people, has a disproportionate share of their state budget that's predicated on very wealthy people paying these ridiculous rates. And so when those people vote with their feet, they're no longer here, it's going to have a tremendous effect. and typically what happens in Europe is the government has to go to an austerity program because the state isn't allowed to run a deficit and some European nations aren't, especially as a function of the EU. And because of that, basically you have to cut services. That's what austerity basically is. But in a progressive political regime, you can't cut services because all your constituents, all they want is more services. And so this is why I think California is headed for crisis. The only question is really the pace.
Of that you've had like six or seven companies, either IPO or, or go IPO at this point. And then we just saw something incredible happen in SAS. Slack get bought by Salesforce. Slack getting bought by Salesforce. Is that a win because it was at $27 billion as $800 million company, or is it a missed opportunity because they weren't able to grow and be independent and, and build the 250? $1 billion company. And I don't know if you were an investor in or had any exposure to it.
Yeah, I'm not really an expert in enterprise software tools and all the competitive dynamics there. I think it's typically unfortunate when a company isn't independent. I think most companies sell out of fear. It depends what the fear is, but it could be fear of lack of growth, fear of competition, fear of internal morale, but fear generally drives sales. I don't think that's a good thing. That said, obviously they're acquiring a significant premium. So it's hard to tell like what was driving that. That's really not an area I pay all that much attention to. I'm not an investor in Slack. I did invest in Yammer back in the day.
Yeah.
Unfortunately, David Sacks sold that one a little early. That could have been much bigger, obviously. But it was also significantly earlier in terms of time. And some of this may have taken more time to bake culturally when a tool like this was more popular. But in any event, I think the IPOs, are more interesting milestones. I think typically once a company has an IPO, it stays independent for a very persistent, very long period of time. I haven't done the math recently, but it's probably something like 10 to 30 years, you know, in that zone of like once you're public, how long do you last? And so I think it's a very big milestone. It's not just a fundraising milestone. It says something about the permanence and durability of a company. So yeah, I've been fortunate that in the last quarter, I've had like six or seven companies Palantir was a big one, yeah? Palantir is that was a very long time. That was one of the companies that subscribed to the advice of don't go public forever. You know, fortunately, and you can look at the evidence right now, I mean, the public markets absolutely appreciate Palantir. They've been trading phenomenally well. Whatever fears they had, clearly, you know, were fiction. So, but anyway, Airbnb is the same thing.
You have exposure to that and that's.
Going, when is that going out? it's this week. Airbnb shares this week. Yeah, yeah. DoorDash prices today will trade, I think, tomorrow even. And then Airbnb.
Can't wait for DoorDash as an Uber, as an Uber investor. Having DoorDash public now creates this two, two horse race is going to be.
Great for both companies. Yeah. Yeah. Well, I mean, I think door dash, you know, door dash is pricing, you know, at a very high price, meaning very popular, like investors really want door dash. And it's because they've been dominating. They been generating market share, contribution margin, retention metrics are phenomenal. So it's a really good, it's an extremely well-run company. People appreciate that. I think they announced the pricing today.
So it'll- But it's gonna be like.
A $15 billion company when it goes out? No, it's gonna go out at $37, I believe. What?
Yep. I think it's priced the last private.
Was like $15 or something? Yep. It's a good deal for those people. It was very obvious that this company was phenomenal. phenomenal, but a lot of people didn't appreciate it. But I'm pretty sure I read, I at least read press reports about the pricing. And I think it trades tomorrow. So it's going to be early this week. And then I believe 24 hours later, Airbnb will price and trade, you know, at this point, barring a nuclear war, these companies, you know, are going to be public companies this week. And then, you know, a firm and open door are falling behind, you know, falling about a week behind on that kind of racing. So I'm hoping to have those, you know, out trading plus or minus a week from, you know, tomorrow or so.
So I just added to, like, you can actually add Airbnb to your watch list on, on, I, I didn't know you could do stocks that were not yet public, but I guess the NASDAQ put a, b and b, and they also put door Dash up on so you could, you could actually put them on your ticker without them being trading yet. Cool. Four Dash is just, yeah, yeah, that's pretty cool.
Well, IPOB is up 18 today.
So, you know, incredible. Well done on that one. I remember when you first told me the idea.
I was like, wow, people always start like 2005. But, yeah, the, the, the, the Market's definitely appreciating some of these companies, which is really nice and refreshing to just looking at the stock ticker now, see if I can add them. But yeah, so it's very exciting for these companies, for the founders, for the teams. Obviously, the investors are thrilled too. That's part of the job of being an investor is to give people money, generate returns over that 10 years later. I mean, that's the funny thing about venture is even though this quarter's been in some ways amazing, all of these are decisions I made seven to 10 years ago.
It's so weird, isn't it? Like, it's surreal to like, I had Uber, desktop metal, Robin Hood, Wealthfront, DataStax, you know, and you have all these other ones. We made these decisions in 2008, 9, 10, 11.
Even the VC ones like Affirm, Open Door, DoorDash are all things I invested in 2013. Wow. So it's like seven, seven plus, you know, seven solid seven years later. So, you know, it is an interesting job and professional role in life when, you know, your true gratification in some ways comes seven years later. And then, you know, you wonder about all the stuff in the middle. Like, it's kind of a very unusual human sort of process.
It's like playing a hand of poker or playing like a chess game. You get like halfway through do it. And they're like, Yep, come back in seven years. If you go to the movies, you watch Half of the Godfather, you're like, yeah, you'll see the end in eight years.
Come back and you'll figure out the rest. Yeah, read a book, put it down halfway through and then pick it up off the shelf seven years later with the two chapters. Yeah, I try to remember everything. Or start writing a book, maybe in a different way, is like writing a book, finish it half, halfway, put and like forget about it for like seven years in some ways. I mean, but in any way, it's just a very long process. And it reminds you of how long the feedback loop really is to build an iconic company. And then you also do have to find ways to challenge yourself in the middle. To know, like, I went on a walk on Saturday with one of the CEOs of one of these four companies. And we're kind of reminiscing, but also talking about the future. And the thing I was debating in my own mind is how do I challenge myself to make sure I'm still finding the same caliber of founders, same caliber of companies in 2020, 2021, 2022 versus the compounding effect of running a company. I was jealous of his job as CEO actually gets easier. because the company develops momentum, it develops competitive advantages. So actually, in many ways, there are challenges to his job, absolutely, but it actually does get incrementally easier. Whereas, like, I'm sort of only as good as my last investment or last year's investment.
Exactly.
I gotta find a way to stay sharp and compete and even measure just, am I, am I making good or dumb decisions? Obviously, the decisions we made seven years ago were pretty good. But who knows what, does that mean that the decisions in 2020 or 2019 even, or 2018 were good?
Well, and then you think about like the open mindedness and the optimism and the raw just boldness of believing in people. And then you have wins and the wins become so big. I think one of the challenges is sometimes you look at a company after you've had such a colossal win, whether it's Palantir, or Airbnb or Uber or whatever it happens to be. then you have to go look at a new two or three person company, and it's a mess. And they don't even have their incorporation documents done. They didn't sign their IP assignments. If fucking thing is a disaster, their diligence would be like vomit producing. If a lawyer looked at it and you're like, how do I get up for this entire, you know, restart? And, you know, that is the, the challenge you have as an early stage investor is you, you have to find meaning and joy. This is what I've come to in this great pause, Keith, because you and I are friends. Like, we have this, like, therapy session we do every three, four, five months about our jobs. I realized it's the joy of meeting a founder and placing a bet before anybody else and then watching and just being supportive. And then, man, when it hits, it is so wonderful to be the person who believed in calm, which 40 people said no to, or when we did Uber out of 21 investors, me, Cyan and Saka. Saka met them on their own. Me, Cyan and first round did that five million dollar round. It's just like it's so out of 21 people were at the open angel forum. How do you find meaning and all? Like when you've obviously become post economically, you know, dependent on this, how do you find meaning in it?
I think there's a couple of things that are really important. One is you remember the companies that nobody else liked and that your decision to fund made a meaningful difference in their potential of fulfilling their dreams. There are some companies when you invest and truthfully, there's a lot of other people that would have, should have, could have invested. And it's not as if necessarily your money made a material difference. There's some companies that nobody appreciated that people really strongly disliked that your ability, momentum, connections, dollars actually did fundamentally allow the company to prove some things and validate some things and become more of a consensus opinion. Those are the more psychologically rewarding companies by far, even if other companies might produce large returns. If they're super popular, super hot, but you happen to win an investment, it's less psychologically rewarding. There's other ways that VC where you can get psychological rewards from first class of companies where they're popular. It's by being a good consigliere to the founder, helping the company hire fire, strategize, prioritize. Like, there's definitely other ways to help the company. So, for example, I led the series a for our firm, Maxellens company. It's gonna go public probably about a week from today. There are a lot of people who want to invest and lead the series a for Max's company. And think about, you know, Maxellens. I mean, Max had already been extremely successful as a company in financial services. Like, the only question was not like, should we invest as a question? So it's like, you know, how much can we get? Yeah. And how do I convince him to take, you know, KV, my money and, you know, appoint me to the board versus, like, other choices?
Yes.
So it's not like me giving him the, you know, whatever, 15, 16, 17, whatever, million dollars made it possible. He was going to get the money from somebody, period. He's going to get the money on better terms from other people. So what I could do then is be useful and remember certain conversations. that I had with the executive team, either holistically or with him, that may have helped clarify things and made the company a little bit better, a little bit sharper, a little bit more resilient in certain places. And that is psychologically rewarding, but it's not because I gave him money. So you don't have to remember versus when Airbnb, when I committed to invest, literally there was nobody in the planet that liked the company, period.
I think I think I do.
Ryan introduced me to the company twice, the entire company, as the only person who actually liked Airbnb. Like Paul Graham and the YC people love the founders, which is very good judgment, clearly historically brilliant, but they didn't actually like the idea. Actually, I obviously was impressed by the founders, but actually as soon as he articulated the idea, I believed in it. And they could, in the founders, you know, that's where Joe, Nathan and mind could tell the difference of like, no, no, you actually really like what we're doing. And so the same thing was true of Palantir, even though I actually wound up funding, investing later, when Joe Lonsdale and Peter first articulated it to me, I was like, oh my God, this is so obviously good. And Joe has publicly said before that I was the first person that wasn't a founder. I actually thought it was a good idea to try to do this. So those are obviously, you know, psychologically rewarding, or I did write the first check and wish, and wish, and wish nobody, like, everybody loved the founders, but they wanted social commerce. Well, they wanted these guys to chase an ad network because that was their background. Both Peter and his co-founder had had significant success at both Google and Yahoo building ad networks, and everybody's like, you should build an ad network. And I was like, no, I want you to go chase a consumer product that's predicated on leveraging some of your learnings. And if it fails, I'm fine. if you can't make it work and you want to regress back into an ad network. But I'm giving you money explicitly to go chase this. And everybody else was like, no, no, no, no, no, no, no. We'll only give you money if you.
Promise not to chase it. So obviously that- what the world needs.
Is like another ad network. Yeah. Yeah, 100th. Right, exactly. But anyway, so like that's obviously- so meaningful. Yeah.
That's obviously rewarding and cool. How do you deal with the losses? Are you, do you get angry when you lose and it could have been avoided, you get frustrated or just, are you able to sort of like, you know, compartmentalize the losses even when the founder screwed up or, you know, is bad execution? Can you compartmentalize it? Or like me, do you get crazy and grind your teeth and have a hard time with losing?
I, no, I don't get frustrated. I think there's an art to being an early stage investor, which is if you're not failing a certain amount, you're probably not taking enough risk. You're not chasing ambitious enough things. Because by definition, let's start from first principles. The idea that two kids in a proverbial garage are going to change the world or change an industry, think Elon and Tesla, or one of these companies like Square, Stripe, et cetera, changing financial services or Robinhood and brokerage or Trade Republic in Europe. That's a pretty ridiculous concept and fair the irrational per state. A certain fraction of them absolutely should fail. It's like saying you have a kid who's seven years old and your goal for that kid or the kid's goal is to play, you know, be an NBA All-Star yeah. A reasonable number of people that have that goal and actually have a lot of talent and a lot of dedication are not going to become NBA All-Stars and if you just sit around bemoaning not becoming an NBA All-Star that kind of loses sight of, like, how, how tall and it really goes the odds are versus enjoying the experience of becoming a world-class athlete. Like, you can be a very proficient athlete and not, you can win. Nobody can stop you. You can win. You can win the NCAA championship and still not be an NBA player or not be an NBA All-Star and so I think you want to fail a certain amount. And it's like baseball, which I'm a big fan of, is nobody, like, nobody plays baseball, like, thinks they're gonna bat a thousand for the season. Like, that's, like, I'm very happy at 40%.
Give me people who are swinging for the fences now, right? The whole game has changed.
It has changed that way. And that's changing a little bit of venture because of the size of funds. Like, you know, the proverbial success when we were growing up was like a billion dollar company.
Yeah.
These days, you know, truthfully, the funds, the funds that, you know, I, I've worked out and the funds I could be with, they really need 10 billion outcomes to meaningfully move the needle. Well, if you had a $600 million.
Fund, a billion dollar fund, and you're buying 20% of a company, typically, or 15%. I mean, it's got to hit 2 billion and now you've returned half the fund. Yeah.
Congratulations. You ideally want to return the whole fund on, like, on your, now you.
Need a five or $10 billion one.
To get past the hurdle. So, so you do have to kind of swing for the fences a little bit more like the baseball change where people are much more, you know, where.
The basketball three point shooter. Yeah, three point line.
I'm actually Daryl Moore is going to come on the pod. Oh, cool. I'm talking to him right now. I definitely want to, I definitely want to to listen to that. But so in any event, I think that the things that probably are more frustrating to me are actually not failures. It's the successes that don't achieve.
The.
Ambition or the size or magnitude that could have. So it's more like a company's pretty successful, but it could have been incredibly successful.
Okay. So yeah, when you would pay pal and Yammer sell for a 1100 of what they would be worth, that's, that's hard to swallow.
Not hard to swallow, but definitely a little bit more mentally, you know, sort of frustrating. It's like, oh, well, maybe we could have made this bigger, better. You know, if we just changed this or done that or not hired this person versus the ones that actually fell. Like, that's just part of the process of trying to change the world.
Yeah. Failed experiment versus not selling too early and not having the outlier success or.
Not being willing to reinvent yourself and take the next stage. Like, you know, you see some of the afterburners like kicking in at Square and that's a function of Jack's leadership and willingness to take risk.
It's crazy. I was in a fund on Square and they distributed this. What did Square go out at?
$15 or something? Yeah, like 3.5 billion or so plus or minus. It was like 15 bucks or something. Maybe even a little less at pricing because there's some stress.
Like 13 to 15 bucks, let's say. So then it got distributed to me at like 50 or 60. I sold half because the venture fund that I had it, I was an LPN. I guess they held it to distribute it because they knew that it was still growing. So I get it at 50, I sell half of them and then I leave half of my account. And then I woke up the other day and looked at it and I was like, what is happening to Square where you worked? It's all Cash App, right? That's the thing that's changed our face.
Cash App has really propelled the company's valuation. And that was a big, bold innovation that really was top down that both bottom up, there were some champions in internally, they're at proselytizing, but it's really Jack's commitment to bold, ambitious bets and his desire to create a consumer success that led to that. And so that's why Square is so valuable in some ways. And so there are companies that win, there are leaders and companies that wouldn't have taken that risk, that wouldn't have embraced the team, that wouldn't have created the cultural like sort of conditions to enable a team to execute on a creative app. And so that the companies that don't do that, that could have, should have, those are maybe a little bit more.
Of a What's the story with Jack? You worked with him. People think he's a little weird. You know, he's got the beard. He goes to these, like, he seems to show up for every time the government calls him. He actually goes. He's very thoughtful, but some people think he's a little out there. And, you know, the Twitter guys were giving him a hard time in one of the books that he wanted to make dresses or something. He's eccentric. Is that an, is he's eccentric but brilliant. He's eccentric but a great executor. how do you describe Jack?
Well, I've never met a very successful founder who's not a little eccentric. I think the people who change the world are like, I have an old expression adage that only disruptive people create disruptive companies. And so I think to some extent, if you want to transform the world, and he's done that at least twice so far, you need to have like a different perspective than at least most normal people, because most normal people people don't see things, can't see things are too rational in their own ways. And so I think everybody we know that's been successful has some of that. And what yields success for people who are extraordinary founders is typically they learn to complement themselves with other people who have different skill sets and different interests. And it's the collection as a whole. Think of Elon certainly is not your standard you know, almost none of the great founders I've ever worked with or the famous ones in history, whether, you know, you read about Steve, all these people have, you know, quirk, quirk, they're eclectic to quirks to, you know, like very extraordinary at some things and less, you know, well-rounded and other things, but they learn to appreciate their strengths and compliment things that they're not so interested in.
What is his superpower? Jack Mercer.
Jack's superpower is he actually he's a first-rate design engineer and business strategist. So it's the combination. He actually understands all those domains quite well. And so when you have that ability to triangulate between design, design experience, software, technical innovation, and business strategy, you can create a lot of things. Almost no one has the Venn diagram overlap of all three. It's actually, usually you're pretty good as a founder if you've got the Venn diagram overlap on two of them.
Yeah, he's. He's a very unique and special guy. All right, well, you gotta go, but I just got to ask you, our Knicks seem to have got a new regime in there. We're drafting very well. We got a ton of picks, but no Superstars came. But we got OB. Mitch seems. Mitch Robinson seems to be improving. RJ seems very good. I'm looking at this front line of. Mitch and RJ and thinking this feels like we're projecting in the right direction, but we do have an owner who just can't seem to get out of the way. What are our thoughts on the Knicks?
Yeah, I mean, my, I'm still, you know, moderately skeptical only because it's a top down problem is if you're going to build bottom up, which is kind of like the way you were describing and then, you know, complimenting with a superstar at some point, you need to stay consistent with your strategy for a bit of time. time. This is, there are fixes, it's hard to do a seller counts, but there are fixes that are more immediate with an inpatient owner. They, as you're getting progress against the strategy, they tend to rip it up and shroud and you go back to square one, which is why the Knicks have basically not been very good since 2000. I mean, maybe me going back to the East Coast will be good for the Knicks. Absolutely. Last time the Knicks were good, I was on the East Coast. So to some extent maybe this will fix things.
I'm hoping. I mean, basically it's the only reason I'm working. I'm just like, if I can just get like 10 more Ubers, just keep.
Working for 10 more Ubers.
You could buy the Knicks, but the.
Problem is- you- want to syndicate the Knicks. The owner still needs to be willing to sell.
I mean, you can only buy what's, you know, you can't buy what's for not for sale in some ways.
That's the problem is I think Bezos would buy it.
I mean, that was the rumor was that Bezos wanted to buy the Knicks.
And he could buy them.
Can you imagine Bezos So sitting courtside, he would be like, yes, spend what you want. And yeah, I think you guys make decisions.
I think it's a great idea. I think he should retire from Amazon.
And buy the Knicks and fix the Knicks. And then look at Utah. Jazz just got bought by Ryan.
So yeah, more technology people will be buying sports teams. I mean, I think Sacramento, just because you can create wealth. And you know, traditionally, sports teams were owned by car dealership owners. Like that was actually the most common occupation of people who own sports teams. And so I think the modern technology Trophy World, you know, you have, obviously, Steve Balmer, Etc. There'll be more. Yeah, there'll be, there'll definitely be more of that, which is a good thing. But, man, yes, I would, I would be very, very, very, very excited to have Jeff buy the Knicks. I can just, I can't wait. I can't wait to read the memos. They're gonna have a writing culture all of a sudden.
I need a memo on how we're gonna deal with Club. seats. And I'll fly up.
If he buys the next, I'll commit to flying up for half the home games.
Absolutely. You and I will split some court sides. All right, my friend, Keith, thank you so much for coming on the Pod. Being so honest and candid, we could have gotten into a hundred other things, but I took you for 90 minutes and you're a great guest and just great at what you do. Keep it up and enjoy Miami.
I'll see you there soon. Say hi to Pitbull.
Thanks. I'll say, hopefully I'll get to say hello to Pat Riley. Yeah, exactly. Oh, yum, yum. I mean, that's quite a team. The heater, man. What's that kid? The. Who's the guard over there who was derided? And then he just overperformed. Who's the guard? Jimmy Butler. Yeah. Butler is just a beast. I mean, they were like, this guy's a malcontent. It's like, oh, no, he just wants to win and is telling everybody around him to work harder. I mean, what a run they had.
I love that. I mean, Pat Riley was one of my heroes sort of growing up and I've never met him and hopefully moving to Miami, hopefully moving to Miami will help.
No, that's easy to solve. Hey, somebody who's listening to Pod knows Pat Riley.
Can you put him to just somebody get me on a CC list?
I actually know who does. But now that I'm there, hopefully we can arrange this. The mayor definitely knows Pat. Pat's the greatest. I loved Pat Riley as a coach. He was so hardcore, so serious and like, man, whatever he did to get to create the first super team and get, you know, LeBron and, you know, Wade to play together. Oh my Lord, he's old school. One of the books that I read.
In high school that was really inspirational for me was Pat's book, the Winner Within. And there's a lot of lessons in there that I kind of interwove into my own life. Any big takeaway?
What's the big takeaway?
Yeah, the biggest one is he has this great quote that I sometimes recite, which is, you don't want to be the best at what you do. You want to be the only one who does what you do. Which he actually was quoting, paraphrasing from Jerry Garcia of the Grateful Dead. But I remember reading this junior year in high school and it becoming like the mantra for myself.
I love it. Well, you are one of one, that is for sure. We'll see you soon, my friend, and we'll see you all next time on this week of startups.
Pleasure to be with you.
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