TRANSCRIPT
slava (00:02.027)
Hello and welcome to the next episode of Smart Humans. I am super excited about today's guest. I've known him for well over a decade, but only more recently got to collaborate with him. Many of you listeners will already know him as he's a media influencer out there and a super angel. Jason Calacanis, welcome to the show. Absolutely, well, we always start in the same place, which is asking, how did you even get into alternative investments at all?
jason_calacanis (00:22.582)
Thanks for having me.
jason_calacanis (00:32.042)
Well, I was a journalist and then an entrepreneur in the technology industry. And after hosting a bunch of conferences where people launched products, the first of which was in 1995, if you can believe it, it was called ready set pitch in New York, Ted Leonsis from AOL was there and we had people pitch five ideas. Ever since that time,
Uh, people said, wow, you're good at picking companies and as a journalist and putting people on the cover of Silicon Island reporter magazine or doing engadget, auto blog joystick. We just had a good editorial sense of which companies to focus on. Well, the job of a journalist, very similar to the job of an investor. You're meeting a bunch of people trying to figure out who's going to change the world, who's the most interesting, who's not full of BS and
Sure enough, it turned out Sequoia Capital, a venture capital firm here in Silicon Valley asked me to be a scout for them and the scout was a new concept. We'll give you some money. You invest it. We'll split the returns 50 50. And so I started doing that with Sequoia, hit a bunch of hits like Uber, Thumbtack, Data Stacks, great companies. Then I started some small funds and I now have a 21 person.
investment company that does a bunch of podcasts you may have heard of like this week in startups and all in, and conferences. And then we have an investment team and we invest about a hundred million dollars a year now in startups in the early stage.
slava (01:55.643)
Amazing. What year was that Sequoia effort that you were working with them as a scout?
jason_calacanis (02:00.894)
I guess 2009, it started right at the, you know, tail end of the Great Recession, which is paradoxical considering we're probably in a recession right now.
slava (02:10.107)
Yeah, we want to talk about the market and how that influences. Sounds like that was the springboard for you. Is that right?
jason_calacanis (02:16.118)
Well, you know, I always tell people like fortunes are made in the down market, they're collected in the up market. So the best time to be investing is in a down market. You know, people know the famous quotes about blood on the streets and investing when people are scared and being scared when everybody is greedy. So you know, when you're investing in a down market, there are less people starting companies and less people investing in them.
This means you can take your time, get to know companies, make a really thoughtful investment, not out of fear or FOMO, but out of really doing your research. And then the people who are active during down markets tend to be the most resilient, the strongest, the crocodiles, the sharks, the cockroaches, the people who don't die. In a down market, a lot of the people who are playing the part of founder or investor,
but who aren't really committed to those roles and they don't do them for a living, they tend to go away. So it's been tourist season in Silicon Valley and startup land for five, six years. And I've seen this movie before the tourists come in, oh my God, I wanna live here. This is the greatest life I could ever imagine. And then they eventually go home. And so they're all heading home now. Some of them licking their wounds. And it's just back to work for the people who do this for a living professionally. And so I kind of enjoy the down market.
slava (03:40.235)
Tour season. No, that's a good line, tour season. I'm gonna have to remember that one. So you obviously know a lot about startups, angel investing, venture, et cetera. How much do you know, how much do you participate in the other segments of alternatives? For example, real estate, debt, collectibles, art or crypto, feel free to pick any.
jason_calacanis (04:02.706)
Yeah, we made a good trade with crypto by Bitcoin when it was like 100 bucks. So, you know, we did well there. But I'm not active in crypto. I'm really active in startups because I like to evaluate the product, as well as the team and talk to customers and in crypto, you typically have a team, and you don't have a product. You may have a white paper, an idea of what they want the product to be maybe some basic bones or some rails of the product that they forked.
But it's very rare that you're investing in a crypto project when they have customers. In fact, most of the products, if you look at them, outside of money transfer, speculation, and store of wealth, you don't really see a lot of products out there yet. And the products you do see are really clunky and nascent. So it's not for me. I have access to the greatest asset class available, which is startups. And so I try to focus on those. I am crypto curious. And I keep my finger on the pulse of it. And I have a handful of investments. But.
It's just not for me because I'm a product person. So I like to look at the product and talk to the customers and that's just not possible in 99 out of 100 crypto investments. I do have some collectible cars. I have the 16th Roadster ever made by Tesla and I just got offered to put that on Rally Road for $250,000 and other people are buying them for 250k. Those early ones, the first 100, which were called the signature series. And then I have the first Model S ever made.
slava (05:17.119)
Nice.
jason_calacanis (05:30.95)
called the first signature ever made. There were a series of founder series and prototypes made before the public. So I have signature number one of that. And I guess that's worth a million bucks. So I have two collectible cars and I love that. And I would invest in more. I have bought paintings on Masterworks and have bought into companies on Republic, Seed Invest and R-Crowd. I think those platforms do a solid job. All four of those in fact.
I think do a real good job of curating. And that's really what I look for in those alternative platforms. I have a Basquiat. I own a piece of from Masterworks as an example, and probably gonna buy a fractional ownership. I don't own an actual real Basquiat. I wouldn't want to own, I mean, I could afford to probably buy like a modest painting, maybe in that range, but you know, a six or low seven figure painting, but I wouldn't know what to buy. I don't have an advantage there. It would be, I'd be too weighted in one.
slava (06:06.719)
Basquiat you have fractional ownership or a whole owner.
jason_calacanis (06:24.906)
investment. So like the people who angel invest with me at the syndicate.com, the average investor is putting in $7,000. And there's an average of 100 150 of them per deal. So, you know, I like the idea of making a lot of small bets, learning about different asset classes. And then when I have an affinity for them, and dexterity, or some inside line, maybe doubling or tripling down on the things I have some
good firsthand knowledge or some conviction on. And then really startups is the bulk of that. At Real Estate, I own three properties, including my primary residence, and I buy those basically for utility and enjoyment, primarily and secondarily as a hedge against how deep I am in tech. So, I mean, unfortunately, they are also in the Bay Area and Tahoe, so that at San Francisco, so those properties are tied to tech, I guess, arguably.
Um, but I like real estate because you can use it, you know, I think that's pretty great, but I don't speculate on real estate at the current moment, uh, for like an Airbnb or through reets or anything like that, but I'm curious about those and I might do more. I was pretty curious about, um, the fractional ownership of homes like Picasso does and some other platforms are doing, I wouldn't mind doing that with some friends, like creating an LLC and having 10 friends by, you know, in a state in.
Tuscany or something and then splitting the cost and then having a management company run it for profit and then us getting, you know, whatever two weeks each, you know, a year or something or.
slava (08:05.655)
Do you think you would do that on your own with your friends or you think you would go through one of those platforms that you just mentioned?
jason_calacanis (08:12.498)
I would have to do the math on it. You know, if you did it with your friends, obviously that can get complicated, but I do have a couple of friends who have shared a plane before, like a Pilatus, like these little regional planes, and they're not expensive and they're easy to operate. So they're perfect for like, you know, going from San Francisco to Truckee to Vegas to San Diego, LA, that kind of route, you know, the Pilatus PC-12. So I have a group of friends who share one of those.
But they don't do it for, you know, like NetJets. They just did it themselves. They created an LLC. And so, yeah, it seems like this is fractional ownership of assets are gonna be a thing. I wouldn't wanna have to do the work. So I guess that's where using a Picasso or I'm sure somebody will come up with a white labeled version of Picasso or you could use an attorney to do it, I guess, but who's gonna manage cleaning it, maintaining it, and then the scheduling issues. I think those are the big three things that those platforms manage for you.
slava (08:59.915)
episode.
slava (09:10.74)
It sounds like a majority of your alts are really more about appreciation, more speculative, as opposed to yield orienting. How do you think at all if more than zero about trying to get some sort of yield out of your alternatives and getting income generation, or is that not something you think about?
jason_calacanis (09:29.91)
You know, I live in this very, I'm lucky to have this very bursty, you know, pursuit I do have angel investing. And so when something hits, you know, every couple of years, something big hits. And so that's really nice. And then I have the consistent revenue of my media business, this week in startups that you know, does well. So I have not looked at the investments for distributions, because I have those two steady state revenue opportunities already dialed in.
I did have an Airbnb we were running for a little bit, our previous home in our neighborhood we kept for a year and we did the Airbnb, it was a little bit too much to manage personally, if I did and people wanted the house so I just sold it. And I didn't want to be the guy in the neighborhood. We live in a fancy neighborhood and want to be the guy in the neighborhood. Running an Airbnb because one night somebody threw a party in it. And I got them and they did five $6,000 worth of damage which Airbnb took care of and
their insurance and they billed the person for throwing a party. But you know, like, just basically for the neighborhood, which is a small number of homes, having somebody throw a party and your neighbor's calling a local police department is not fun. So I didn't want to be that guy. Um, and it seems like, you know, getting people to not throw parties, even though I had cameras up in the place and it's like, we told them and they signed the agreement, like no parties and then 40 people show up and they share it on Instagram and another 20 people show up. And it was like, literally I'm getting these like.
Nest cam alerts like somebody's in the driveway. Somebody's in the driveway. Somebody's in the drive. Yeah, wake up. My phone is like 50 alerts. It's like, why are people in the driveway from midnight till 5am? It's pretty good fucking party. Sorry, pretty good freaking party. So yeah, the police were not happy.
slava (11:13.569)
So when you buy like the Tesla Roadster or the model signature number one, if I'm saying it correctly, are you buying it thinking that, oh, this is gonna be worth a lot one day or is it this is just awesome, I want to own one of these because it's interesting or, you know, my buddy is doing the company or running it so I just want to see.
jason_calacanis (11:21.239)
Yeah.
jason_calacanis (11:32.39)
Yeah, it was because I'm friends with the founder. But in that case, I kept them I could have sold them early on. And a lot of people I know who did have early versions did sell them. But I did understand having number 16 and number one was very significant. If the company thrived, or if the company didn't make it, and let's face it, the company didn't, you know, almost went out of business three times, two or three times. So either way, those cars are super valuable, and they'll be more valuable in 10 years than they are now. So they'll probably be worth
you know, low millions each in the coming years, I would think, in the next decade. So.
slava (12:06.799)
And are you thinking that you're gonna hold it quote unquote forever and pass it to your kids? Or do you have some sort of number in mind when you want to sell the signature number one?
jason_calacanis (12:13.81)
I, it really is, you know, for the real issue is having garage page for them is like super pragmatic and also having to, you know, have the custodianship of these. So like what I like about, you know, the little piece of a Basquiat that I own from Masterworks is I don't have to deal with it. They deal with it. They store it. So I might give Rally Road the Roadster, the 16 Roadster.
just so it sits somewhere and somebody's maintaining it and making sure it's plugged in and all that kind of good stuff. And then I get one of my parking spaces back. But the Model S number one is just such a collector's item. I might keep it till I'm 70 or something. Yeah, nothing.
slava (12:55.975)
Yeah, that's I mean, they both sound amazing, but that sounds like it's super special.
jason_calacanis (13:01.302)
kind of super special. I'm trying to feel how emotionally I would feel if I were to sell these and then somebody else were to sell them for a lot more in 10 years or 20 years like the idiot insurance. That's one of the nice things about Raleigh Road is they said I could sell half of it. So it's worth 250K. So if I sold half of it, I get 125K right now I paid 150 for it. I'm not sure how that works on the tax basis. I have to understand that but I would be able to recoup some of my original investment while still owning half of it.
So if it did become worth 2.5 million and they sold it, or if they chose to sell it in five years and it doubled in value, I would get another 250. So I would still be in the game, right? Which I think is why some of these platforms are gonna do particularly well. With the Picasso example, the home I bought, my ski house, Picasso wanted to buy it, wanted to, with the original owner, give them like two shares.
and sell six shares or take half of it and sell half of it. They wanted to do that with me possibly. And I didn't want to have to fight to get ski week and Christmas with the new buyers and being a lottery for it. I bought it specifically for those moments in time. But eventually, when my kids are grown, yeah, maybe I'll put them in the Picasso pool and keep one eighth of it. That's possible. I think it's an interesting way to liquidate assets while still maintaining some ownership in them. If you owned a Picasso,
and you gave it to Masterworks, I suppose they could sell shares in it and you could keep 10% of it or 20% of it. I don't know if they do that, but that's actually a really interesting thing about this alternative asset class is that for people who have an affinity or a love for what they own, they can keep some equity in it and keep some skin in the game.
slava (14:44.455)
Yeah, I would totally agree with you. I think actually the most expensive car just sold recently, like a Ferrari for, I think from the 50s, for about like $140 million. So there's definitely some upside.
jason_calacanis (14:54.358)
Wow. Isn't that crazy to even think about $140 million? That's like you could buy a jet and then
slava (15:00.219)
Yeah, yeah, and then a Warhol just sold for 195 as a painting, both setting the records.
jason_calacanis (15:06.442)
I mean, it's like, I just think about that. And I think about other assets, you could buy the most expensive private jet, a global 7500 or 7000, whatever that is for 70 million, you could operate it for years, for 10 million for your pilots and fuel, or 20 million, that's 90 million. And then you could buy 10 $10 million homes around the world or whatever 5 $15 million homes and staff them. And it would be the same as that painting.
So it is really amazing what exactly, I mean, this is.
slava (15:35.675)
The people love their rare assets. Having what other people don't have is special, like you have that signature number one.
jason_calacanis (15:43.326)
Exactly. Well, when you think about it, you'd say, Well, why would anybody do that? If they if they could have either or what's like they already have that they already have the plane and they overbought that for 195 million. They're like, but I already have a plane and I already have 10 homes. So why would I do that? Like, I don't I've already got those things. I've experienced that. I want to experience owning this.
slava (15:51.418)
Right.
slava (16:01.855)
So transitioning to the market overall without picking a specific vertical, just really getting the hot takes from Jason, what do you think of the market today? And take it wherever you'd like.
jason_calacanis (16:14.07)
Hmm. So market obviously got overheated. We had a ton of stimulus. We talked about this a lot on this week in startups and the all in podcast. And market got overheated, we printed too much money. COVID created a bunch of indigestion in the system and a lot of weird things that all occurred in a very fast fashion. You know, we're talking about like a 30 month period here, where people didn't leave their homes and had money dropped on their heads like unemployment, extra unemployment, stimulus.
PPP if people forget that like companies got six months of revenue, you know, if they didn't fire people So there was just money dropping from the sky. What did that do? Well, you know a balance sheet has you know You know revenue and your costs. Well, they got all this money coming in Stimmy checks, etc, and they didn't spend any money because they were stuck at home So there was no going to the movies with your family and buying a bunch of popcorn and parking and all that stuff There was no Disneyland trip
Disneyland was shut down. There's no going to a Warriors game because they were playing in the bubble if people remember that. So people had these record massive cash balances on average. Now, of course there are people who are suffering and people died, but just looking at it economically, we printed far too much money. And thank God we didn't do that last couple of trillion dollars in stimulus. But low interest rates and a massive amount of spending set us up for assets.
to become overvalued, you know, Peloton, whatever, you know, we were trying to figure out if Peloton was worth it. And I was like, they're getting 30,000. I think if you just at one point, I did it, it was like $30,000 per subscriber. And I was like, well, you'll never make that back. So we're betting that they're going to have, you know, whatever, 10 times as many subscribers, which might not be a bad bet. But we're giving people a lot of credit in startup land, and in public markets, for work not done, right? We're valuing companies.
for executing perfectly for the next five years. And so I sat out a lot of deals because I couldn't justify paying $50 million for a startup that wasn't launched worth 25 million for one that had 500K in revenue. So, you know, and you and I talked about this when you were raising money for Vincent. And so, you know, you have to be disciplined as an investor. You have to think about entry price. Entry price does matter. So people were looking at, you know, these crazy outcomes. I was lucky enough to be part of the Uber outcome.
jason_calacanis (18:36.47)
But people are looking at the Coinbase outcome, which has since gone down, whatever 80, 90% or the Peloton outcome. And, you know, if you didn't get to liquidate your shares at the peak in time, it perfectly, you know, you maybe didn't do so well. So, long story short, you know, the pandemic and all the stimulus created a very weird environment. So then we have this hyperinflation. Nobody's ever seen anything like it. Then you have Ukraine and.
you know, the supply chain issues, China on lockdown, you start putting all these macro events together and you get crazy inflation at a time when we also have a record number of jobs and a record low unemployment. So when you talk to people who claim to understand what's going on here, you know, recessions are based on people not having jobs. Well, we still, even though we started the layoff train now, people still have multiple offers coming out of their layoff.
we still have 10 over 10 million jobs open, we still have record low unemployment. So this is going to take a weird series of quarters, where we're going to see inflation going up, layoffs happening, but the number of job openings still being high record low unemployment, but asset prices getting crushed speculative ones like Bitcoin or speculative ones like some
jason_calacanis (19:59.49)
the market and individuals are just going to have to rebalance and reprice everything. And so it's like the great repricing and the great reapplication of people going to work. And I think the silver lining is there's a lot of bad projects out there, whether it's crypto, or startups, there are weak companies, there are individuals who are weak and not working and should get jobs and should, you know, be productive in society.
So when you have these recessions, and I've lived through two really intense ones, createrecession.com as a professional, it tends to make everybody focused on what matters and it tends to be super healthy. So this is a great flush that's happening. A lot of stuff's gonna get flushed out and what will be left will be the strong companies and the strong individuals and the talent dispersion that's resulted in a lot of average projects. You know how hard it is to hire people.
Instead of people having 10 offers, you know, a mediocre person having 10 offers, you're going to have a great person with two and a mediocre person with none, and instead of having to sit there and negotiate a pay package that you as a CEO or a founder are like, this doesn't make much sense, you're going to be able to say, Hey, this doesn't make much sense. And, you know, what do you think about this package? This would make sense to us. And, and then people were like, you know what? I don't have anything else going on. So yes, I'll do it.
you know, that's what it was like after the dot com bus and after the Great Recession is people are like, I have nothing else going on. Sure, I'll work at your startup. And when that happens, great magic happens. People are like, I might be able to get a good job at IBM or GE or Google, but they're on hiring freeze. That might be a crummy job. Yeah, I'll take a flyer on a startup. And I'm super talented, by the way. And I'm ready to go, you know, so that's the thing I'm excited about. I'm probably going to invest more in startups in the next year or two than I did the
previous two years, because I was kind of taking a pause on investing in overpriced start, I definitely took a pause on overpriced startups. And I was being very strategic in ones that are, you know, let's just say, aggressively priced.
slava (22:03.535)
So you've implied a couple times that pricing has come in. Can you give some perspective? Are we talking 5% in, 50% in? Are we talking across the rounds? Is it only seed money? Is it the pre-IPO? Where and how much?
jason_calacanis (22:17.138)
Late stage companies are cut in half. So you know, what would have been a billion dollar valuation is 500 million. So if somebody was getting 100 times revenue for a SaaS company, or 200 times revenue, so they hit 10 million, and people said this is worth a billion where they hit 20 million percent is worth, you know, a billion five or whatever, that's over. So that got cut in half, people might say it's worth 3040 50 times, you know, revenue, top line in a SaaS company.
And then in private markets, people were raising at 25 to 50 million without a launch product, that's over. And then those companies are now if they did raise, and they had, you know, 10,000 a year in revenue, or they just launched their product had no revenue, and they were worth 50 million. Hopefully, they have enough money to work for three years to get to five to 10 million in revenue, so they can be 10 times revenue, right? Or 20 times revenue, something like that, to be more realistic. So
That's where you're going to see a lot of pain and suffering at the early stage. We used to invest in companies for 5 million was like a standard seed stage. Um, and then it went up to 15 to 20, and now it's coming back down to six to 12. So it'll be normal again. Um, you know, the, the idea that like a bunch of dentists and whatever, go to a Y common or demo day, they place 25 K bets, you know, after seeing a two minute presentation and a high pressure, like the rounds closing FOMO that's over. Uh, the FOMO.
hard driving startup investing has stopped. The people who I was talking to six months ago who didn't close market are now coming back with valuations that are much more realistic, plans and growth plans that are more realistic. And I don't wanna say humility, but more realistic expectations of what it's gonna take to build value. There's been a lot of entitlement, but across the board, employees have become entitled, VCs have become entitled.
public market investors, crypto investors and founders, everybody got entitled. Everybody thought this was easy. It's never been easy. And the people who were like Coinbase investors were like, I'm the greatest venture fund ever. I'm the greatest investor ever. I said, I know that with the Uber investment, like you can get a lot of adulation for making some great investment.
jason_calacanis (24:37.838)
you also have to be able to capitalize on that investment. You have to be able to realize it. And a lot of people were locked up in a lot of these investments, they never realized it. And so, there's a lot of lessons here. I was always selling on the way up as an angel investor. If I get an opportunity to sell, if I'm investing at five or 10 million, and an opportunity to sell in secondary comes along at 250 million, 500 million, a billion, you can be sure I'm gonna take that or at least consider it deeply and sell 10%, at 250.
10% and 500 10% and a billion. Well, I look stupid if it goes to 10 billion, maybe but I got to redeploy that money and more startups that could also go on an attorney. Exactly, you know, you take a little downside protection never hurt anybody. I mean, if you lost 90% of your Peloton invest 95% of your Peloton investment, your Coinbase 90% of Coinbase investment, whatever it is not picking on any particular company, but you know, the valuations got too high, they're probably too low now. But let's just say you lost 90 cents on the dollar. Well, if you had sold
slava (25:15.237)
Right now you're playing with house money.
jason_calacanis (25:36.502)
20% of your investment, you would not be down 90% right now. You'd have that 20% as a flaw, and you'd still be at 30% or whatever, or so of your peak investment. So it really is important to have some downside production and lock in a win. And a lot of people don't do that.
slava (25:54.619)
Now that you've gone through those other down cycles, recessions, bear markets, et cetera, what do you tell yourself or what do you tell somebody who hasn't gone through those things as to how to navigate this as an investor?
jason_calacanis (26:09.758)
I think having a great process and a strategy and a plan is very important. So process, I meet with a lot of companies, discipline. We like to invest in a certain Goldilocks window, not too cold, not too hot. So that's our strategy. And then we have a second strategy of when they're a winner and they break out and they're growing three or four X year over year to invest more until we get to about a 15% ownership position. And so if we're consistent with that.
And we do our job and meeting a lot of companies, investing in the ones executing at the highest level, and then quadrupling down on our investment, starting with the three, four, five, 6% investment size. And you know, and there might be exceptions to that when we find an amazing founder, we might want to go right to 10%. But if you start with a 5% investment, and then the valuation goes up, and the revenue triples and the valuation triples, and then you go to 10% ownership, and then it doubles again, and you go to 15% ownership.
you probably, you know, have optimized pretty well. Now, it would have been better to buy all those shares at the lowest valuation, but you wouldn't have known if they were going to make it. So I really have fallen in love with over my 1112 years as an angel investor, the milestone based process we have here in Silicon Valley, you don't need to buy all the shares in the seed round. You just need to be a great partner to the founder. If we're a good founders to you, and you do another round, and I ask you, Hey, listen, I'd like to put a little more money in.
chances are you're gonna let me and I probably have, if you at least do your documents well and you come to reasonable agreements with your partners, you'll have pro rata or even super pro rata depending on what kind of agreement you can come to. So I think I really am obsessed with the process because you can't determine the market, you can't predict the outcome. So what is in your control? And that's really what I focus on. So how many companies, how many people
you know, apply for us, you know, and reach out to us to get investment from us. How many do we meet with? How many do we sort? How many do we meet with? How many take second meetings with? How many do we follow up with? How many bets do we place? How many bets do we double down on? And how many bets do we double down on again? And then how many opportunities do we have to liquidate those shares ultimately, right? And get a return for ourselves and our investors. So, so, you know, a lot of folks, um,
slava (28:24.659)
What was that Goldilocks window you're referring to?
jason_calacanis (28:30.594)
do not have a strategy of where they want to invest. They just fall in love with the founder who's charismatic. And if the team's charismatic and it seems like a really good story, the narrative works, they kind of get taken by the narrative and the performance of the founder. And narrative is important, right? Telling a story about, hey, alternative assets are going to play a role in the world. And we think we're good at that, and we're going to create opportunities for people to invest. It's a great story. I fell for it. I was like, oh, yeah, I'm taken by that story.
But I also need to see execution, right? And I need to invest in a certain window. So too cold for me is you have an idea, you've got passion, and you've got a white paper. Too hot is you're at $20 million in revenue and a $200 million valuation, and you're selling 1% of the company, and you have a quarter percent available to me. I'm not really going to be able to build a position there. So what's just right?
Okay, you've got your product launched, you're at 250k in revenue, 20k a month, 30k a month, last month, I times it by 12, we come to a reasonable valuation multiple on that. And we get to buy 5%. With the understanding we're trying to build a 15% ownership position. So in future rounds, we're definitely taking our prorata. And if things are going well, we're likely to ask for super prorata. So we have that discussion with folks, you know.
If it goes sideways, are we going to want super pro rata? No. Will we take our pro rata? Probably. If it's going poorly, will we do bridges and take pro rata? Probably not. Your job as the founder to make sure this thing is growing if you want to get additional funding from us. But if you do, if you are growing, we're going to want to put more money in. And that's just straight up portfolio management. So that's the Goldilocks zone for us. And the valuation matters. So people who want to have a $10 million valuation,
and do a pre seed round, which I don't even know what that means. Like that's friends and family or sweat equity where you like actually you put skin in the game. It's like I want you to put skin in the game. We haven't made anything yet. You're gonna give me the money to quit my job. I'm like, I think you save money and then you quit your job. And where you get friends and family you quit your job or you build on the weekends and then you quit your job. Like, it's not my job to give you the 250k to quit your job and hire a dev shop and you know, for you to go to some conferences or
jason_calacanis (30:51.726)
crypto parties, you know, like, I think that's in the entitlement level, you know, like, I'd rather see people just work, you know, as a consultant, three days a week and do their side project four days a week, work seven days a week and get the product to 10k a month in revenue or launched and then raise a proper seed round, it's better for them to not dilute. So a lot of people wanted to skip steps on both sides, by the way, there were investors who wanted to skip steps. They didn't want to do diligence, they didn't want to talk to customers, they didn't want to have to
go build a network and a podcast or whatever or do meetings, they just wanted to look at whatever Sequoia did in the last round or crafted or Jamaf did and then dump, you know, $20 million on the head of that company. Like, you know, I like someone like the Tigers were coming in, you know, I didn't have too much exposure to all of them. But these hedge funds or public market investors dipping down into private is always, you know, challenging, especially if they're not like doing the work, you know, my understanding is and
all cases they weren't they were relying on other people's reputations for investing in these companies maybe not doing you know, a really good enough job with diligence.
slava (31:58.503)
your consulting story is actually what I lived, which is when building Indiegogo, I was a consultant during the day and at night, helping to create Indiegogo. So I hear you. Exactly.
jason_calacanis (32:08.97)
Yeah, here we go back to the future. I mean, that's what the next couple years would be like. And then you know what that does? It sorts the founders. If you meet a founder and they're doing that, like a tough founder, like they're not going to give up. And if the founder needs you to give them the 250k, and they want to go to parties and to loom and expense them and pay for their apartment and go crazy and you know, they don't have any revenue. It's like, okay.
slava (32:21.149)
Absolutely.
jason_calacanis (32:36.77)
tells us everything we need to know. It's probably not an investment for me. I'm looking for serious people, serious company builders. It's like what I've learned is like, if you're not serious about it, this isn't like a hobby, it's a vocation. You have to really be into it.
slava (32:39.839)
So you've invented.
slava (32:43.795)
Right.
slava (32:54.547)
Off the top of your head, how many companies do you think you've invested in?
jason_calacanis (32:58.152)
Well over 300 now.
slava (32:59.687)
So you've invested in over 300, lots of amazing hits, Uber, Com, Robinhood and others. Now that you have all this data, what can you share with the listener to just give them the cliff notes to have lived your last 20 years, to not make the mistakes and have got the learnings that you have? What does a unicorn founder or company look like at that early stage? And can you tell?
jason_calacanis (33:27.73)
Yeah, so the truth is you're not in all likelihood going to be able to tell. You might have some survivorship or confirmation bias afterwards where you think you can tell. So since that's the case, you really need to get to 20 or 30 bets. You need to monitor those bets. You need to get to know those companies. You need to get updates for those companies and look for signals that they're breaking out. The signals will be undeniable. They've got a lot of hiring
jason_calacanis (33:57.122)
they're probably meandering and doing okay, negative growth, obviously, that's not a good sign. But if they're over 10% month over month growth, that means they're doubling every 72.7 point two months. If they're tripling every year in revenue, kind of undeniable. When you see those
almost, you know, at least my philosophy is to, you know, double click and, you know, take a deep look at why that's happening. And if you don't even have the time, if it's me, and I'm doing portfolio construction, I'm probably going to make the bet. So and you, you want to look at product velocity. Companies are really about three things, the team that builds a product and the customers who consume that product. And if you get that flywheel going, and you're thoughtful about each step along the way,
it'll work out fine in all likelihood. What happens is people get focused on things that are not those three things. So they're not hiring better and better people, they're not doing professional development and training. They're not executing in terms of the product having new updates and regular cadence. And they're not talking to their customers or delighting their customers.
So you got to really delight those customers. You really got to build a great product to delight customers. And to build a great product that delights customers, you really need to have a good team. It really is like at its essence, those three things. People will get distracted by, you know, their total addressable market, their competitors, culture, you know, there's a lot of things that people can get derailed by. And so what I've learned is to focus on those three signals. And
you know, if the person's product is not being updated while you're talking to them during the investment period, like they should be pushing a new release every two weeks if it's software. And so, Hey, when was the last update? Can you share with me the release notes? Like if you've got a software company, you've got a platform, you have release notes, right? And you could pull them up right now. If I asked you to, if you want to see inside.com, we didn't, we did a, a
jason_calacanis (36:00.554)
Republic recently raised I think 700K from our users mainly. And I love this equity crowdfunding and you know, I could raise from venture capital, but I like equity crowdfunding because it gets your users involved. It kind of forces me to be super disciplined, right? Like I like the discipline that having $100 investors puts on me, I feel really serious about it, like invest venture investors who can afford to lose the money have a portfolio strategy. Great. But man, if I had
you know, a million, about 100,000 people put $100 in, I would take that, you know, like, I wouldn't be able to sleep at night. And then if a VC who's got a billion dollar fund puts 10 million into your company, and they lose it, who cares? Like, it's, it's not even 1% of that. What is it? Is it 1% of the fund? Yeah, it's 1% of the fund. So
slava (36:44.412)
How many investors did come into that round?
jason_calacanis (36:46.914)
Couple hundred, it's typically a couple hundred. So, I love that stuff. And I did see it invest before that and that was really great.
slava (36:49.403)
Nice.
slava (36:54.543)
And you're big into crowdfunding as it is, because in addition to launch your fund, you also have the syndicate, right? So you wanna tell the audience about that?
jason_calacanis (37:00.31)
Yeah, yeah, we have the syndicate.com. We were the first, I was the first syndicate on Angelist actually, a little known fact for scout for Sequoia first syndicate on Angelist. And now I went and got the domain name, the syndicate.com. I worked with a company that powered Angelist in the early days called the sure fund management, they did all those SPVs and whatnot. And I'm an investor in that company. In fact, and we've done over 250 of these SPVs. I don't think anybody in the startup space has come close to that. My friend Zach Coleus, I think has done 100.
25 or 150. So actually, he's probably number two. And our first deal was calm.com is still our best deal. We invested 376,000 at a four or $5 million valuation, the company's worth over 2 billion. It's a very large position for us, a nine figure position, I guess. And we've been actually able to sell some of those shares over time to give some, you know, incredible returns to those
investors and still have the majority of our shares. So it's been pretty great. And I love syndicates because I send them a note. Hey, here is why I'm investing in the company. Here's the DL memo. We did our diligence. Do you want to invest? Here's a webinar where you talk to the founders. You went through this process. So you know how thorough we are. And we take it super serious. Yeah.
slava (38:17.083)
Well, just to clarify for folks, you are a big investor into Vincent, which is the platform which brings forward this podcast.
jason_calacanis (38:24.97)
Right. So, you know, the syndicate also, I think makes me a better investor, because I have to write that deal memo. I have to write a deal memo if I'm investing. But if I'm going to, you know, share the deal with the syndicate members, I think there's 11 12,000 of them now. And I wanted to, you know, I wanted to be good. I don't want there to be a spelling error. I don't want to, you know, if there's a logic that doesn't make sense, and you're sending it to all those accredited, accredited investors.
who many of which are more successful than me or equally successful or smarter certainly, they are going to tell me when I'm wrong and they're gonna take a deal member from two years ago and tell me when I'm wrong. So it's like being in the NBA on the big stage. Like if I turn the ball over, they're like, remember when you turned the ball over three times, you know, it's like, yeah, I do. That was a bad game. You know, like it makes your performance go up when you're on the big stage. And I like that. I like being on the big stage. I like being the number one syndicate. I like that people are
waiting to dunk on me and seeing if they can beat me. And so it just makes me more attuned to what a winning company is. And so I'm not as freewheeling, loosey goosey as I might be playing, not in the world's greatest arena, not in the NBA finals. It's just like, if I was just bawling in the street, am I worried about like playing in the park? I'm not worried about a turnover here or there, or who won, or if I took a bad shot. But in the NBA finals, like
You're going to care about every single play, every play matter. So I just try to live with that level of focus.
slava (39:53.363)
And then you get a lot of information back from your syndicate investors based on here how they're reacting. Are you seeing many changes given the macroeconomic climate that they're kind of pulling back or in the reverse because now you're getting multiples come in and pricing getting better that people are getting a little attracted to these better entry points.
jason_calacanis (40:12.79)
think it's too soon to tell. I do suspect some people will want to take a pause while they digest what they've already invested, especially if they were loosey goosey, because I'm not the only syndicate they're investing in. But I think there'll be a flight to quality and discipline and that would be us. So we have been criticized for maybe not doing some of the big crypto deals and you know, I passed on them or something because I said, you know, I'll totally take a look at this again when you launch the product, but there's no product here. I'm not investing.
you know, in file coin or whatever, until there's a product, you know, and I, the file coin's a cool idea, you know, I love the idea, but for me, I want to wait till I see the product and I can talk to a couple of customers. Right. And so, you know, but other people want to be more aggressive and like, I think angel list or was it coin list or something? I think one of these, you know, folks, they did file coin. I remember I had the file coin people on my podcast or coin list or whoever it was, and they were having like, uh, they were like doing a SAFT.
slava (41:07.595)
Probably coinless yet.
jason_calacanis (41:12.202)
you know, a future agreement for tokens. And I was like, well, this seems
slava (41:15.591)
Right, simple agreement for future tokens as opposed to a safe, which is a simple agreement for future equity.
jason_calacanis (41:19.302)
Yeah. You know, maybe I sound like a dinosaur, but I was like, yeah, I think I want to wait until like this is more than a white paper to sell a token that nobody knows the value of. And you know, maybe that was a losing trade, you know, for much of the last five years. I don't know. But you know, I like to have this discipline. I like to press the advantage I have. I understand startups. I understand products and customers. That's where I understand teams.
crypto and some of these other projects, all I could get was the team. And if the team was focused on fundraising, not product, that to me is a red flag, maybe not like a huge red flag, but it's, you know, submitting red flag for me. And I think, you know, even with the regular startups, non crypto ones, there was a just a whole generation who are better at raising money than building products. And, you know, so they could convince investors to give them money at a higher rate than they convince customers to give them money. That's a major red flag.
slava (41:51.401)
Right.
jason_calacanis (42:18.29)
Now, it's not an insurmountable one. If you can convince a really group of smart venture capitalists to give you money, you're probably going to be able to convince people to use your product. So let's shift the focus here. And this generation, the hardest thing they did was get into an accelerator, or Techstars, launch accelerator, or a Y combinator. That was the toughest. Their seed round was easy. Their seed extension was easy. Their series A was easy. Series B, people started throwing money at them. Series C, nobody did any diligence and gave them this crazy, opportunistic term sheet.
And then now what? Like, now it's like they're, they have the traction of a series A firm, or they're did a series B, and they have the traction of a seed firm, they don't have product market fit yet. Or they have light product market fit. You know, this dangerous place to be. Because you got to fill in all of that credit you got in advance. So if somebody says, Hey, listen, you're good enough to be in the Olympics, and you're not. And the Olympics is like 18 months away, like, you got to get to work.
Is there enough time for you to be an Olympic caliber swimmer? I don't know. You know, you might get to the Olympics and just you might not even make it to the Olympics. Like, so that's the challenge right now in the market. But I do think there'll be a flight towards quality, a flight towards reasonable valuations and traction. We've been valuation sensitive, and traction focused since day one, we never changed that. And this is you asked me earlier, like, what can I teach people? Process, have a process, write it down.
slava (43:25.299)
Yeah, because I-
jason_calacanis (43:43.89)
evaluate your process, if you have people you're working with, compare your process with your friend's process, and then hold each other accountable. So if you were investing in cars or art, you know, hold yourself accountable, write down why you bet on one and why you didn't bet on the other. Like there's a book called Super Forecasting. And part of being a good forecaster is like, writing down why you said no, writing down why you said yes, going back and looking at that decision making process.
And asking yourself like, well, why did we pass on this investment in Airbnb? Okay. We thought that this was a niche behavior. Okay. What didn't we get? What did we miss? What can we learn from missing on Google? Right? There's famously a firm that passed on Google and maybe it was more David out or something. I can't remember the name of the firm, but it was some firm passed on Google and wound up like almost killing the firm because it created so much animosity between the partners I heard like.
You really need to look back on your decisions and say, did I make a good decision like poker players do, right? They look back on that decision. Okay. How many outs did I have? Did I study the hand? How, what was my expected value here? Was there money behind that could have got in if I did hit the nuts? Like, you know, you just gotta be thoughtful and, um, you gotta assess how you made decisions and really refine that process. And literally I was on a call today with my investment team for two hours and a call yesterday for two hours, looking at our process, refining our process.
How many companies are we meeting with? What questions are we asking them? When are we getting back to them? When do we say no? When do we say not yet? How many days? I literally was having a debate today about how many days, if we email somebody like a Calendly link, like to book a meeting, if they don't book a meeting, how many days do we wait before we tell them, hey, do you still wanna meet? And it was like, well, we don't wanna be annoying and do it in one or two days. And we don't wanna wait a week because that seems too short. So we're like sitting there on a.
zoom call going day three, day four, day five, or day six is the number. Which one should we do? The answer was any of those days would work. So, but when I, when I get to thoughtfulness, like we are so far, just to give people an idea that we're now debating if a founder doesn't take a call. Well, maybe we're in their spam fold or maybe they missed it. Uh, maybe it bounced or maybe they got COVID and now they don't remember. And it's in there, you know,
slava (45:38.227)
What was the answer?
slava (45:51.668)
Good.
jason_calacanis (46:03.914)
When do we respond to them? And then how do we respond to them? Is it the original person? Is it a automated response? That's the level of neuroses and OCD I have about the process. So if you want to get good at something, you better be a fucking maniac, because you're competing against people who are fucking maniacs like me. Like, I'm a maniac about this. Like, I don't want to lose a deal. I don't want to lose a great deal. I don't want to miss a company that emails me. If the company's awkward and they're not ready now, well, you know.
maybe when do I follow up with them? You know, and we follow up with almost every company we pass on, or at least we will, they don't even know we're following up, we're checking to make sure we look for signals that, hey, this company we passed on, how are they doing? I mean, you went through the process with me, and we went through the process within Indiegogo, and I had no team. So you actually have a front row seat, where I passed on Indiegogo when we met in South by Southwest famously, I was only writing 25k checks at the time. And then look at like now like
I have a process now I have a team I'm really trying to think it through you have a team and Vincent you're trying to think we're gonna buy these Michael Jordans or this action comic or this you know, crypto project or this NFT or this painting like you got to have a process you got to be rigorous you got to be thoughtful and you've got to keep going back to that process and saying what changed and is this really the best process because that's what you have control over right
slava (47:04.287)
For sure.
jason_calacanis (47:31.434)
You don't have control over the fact that, you know, some, you know, maniac in China decides that this is the greatest wine ever, and I need to corner the market on this specific vintage. Those weird things happen, where all of a sudden Basquiat becomes something or, you know, Jonas would become something and like, everybody's got to own his artwork. Okay, that's not under your control, you know, or like this Marvel character, Doctor Strange suddenly becomes like awesome because Benedict Cumberbatch is
you know, cast as that person and all the Dr. Strange comic books, which cost a dollar and now worth a hundred. Like who can actually predict that? Well, maybe you could because you're watching the castings. And the second you saw the casting, you bought all the Dr. Strange you could. Like, I thought about that, you know, if I was like buying comic books, like I would be looking at the fan boards of who they want to see cast next and just whatever the Reddit maniacs are saying, like I would be just, yeah, buying, you know.
slava (48:21.451)
Absolutely.
jason_calacanis (48:29.494)
who that which characters they are talking about the most.
slava (48:32.831)
So you mentioned Google, and then obviously you've invested in like Uber and many other great companies. Is there an industry that you think one of the great next companies is coming from that you're going to invest from into?
jason_calacanis (48:44.354)
Well, B2B, you know, SaaS, subscription-based services as a business model is really, really powerful and founders are very aware of it. So whether it's consumer subscription where people pay for Netflix, Spotify, com.com, et cetera, and they pay for it every year, that's really powerful, like they did for newspapers or Disney Plus, Netflix, whatever. But SaaS specifically, business is paying on a subscription basis, very powerful because it's very affordable and you get a ton of value. And then I would say,
you know, industrial stuff hasn't popped yet, but we have an investment in a company called blockable, which builds homes and factories. And you know, people saw Uber and Airbnb operating in the real world. And there are other companies that are, you know, flexport is considered like a company of the future. Stripe is considered like Stripe and flexport. I think people right now think will be the next big IPOs in the coming years. And if you look at the Yeah.
slava (49:37.759)
As a matter of fact, as a matter of fact, just so you know, the vault fund actually has flex port shares.
jason_calacanis (49:43.222)
Perfect. So if you look at those two as being two of the company, I didn't know that, two of the companies of the future, they are a logistics business to business company and a finance business to business company. These are not consumer companies. What were the last big ones? Airbnb, Uber, and Google and Facebook. So the last, you know, and Tesla, the last really big ones were consumer facing companies.
And the next group are not going to be. They're gonna be business to business industrial ones in some cases, right? This doesn't mean that consumer's going away. I think tech is just getting so good and the entrepreneurs are getting so bold that they're tackling logistics, education, insurance. They're gonna tackle things that you didn't think they were gonna tackle, payments.
slava (50:12.841)
Interesting.
slava (50:34.095)
Absolutely. You mentioned journalism and media in the beginning as to how you even got into this and now you're so well known for your podcasts and your shows. How does that influence your deal flow, your decision making, your access, etc.?
jason_calacanis (50:49.79)
Yeah. It happens to be that talking is my superpower. I talk too much people say, they told me my whole life, but I love having great conversations and talking. So it's very easy for me to do I don't think every investor needs to do it or should do it. They should do it if they love it and it works for them. Some people are better writers, some people are better at going to conferences, some people are better at doing research and just doing one on one meeting. So I don't think there's one
path, although a lot of investors have been following my path. And it seems like if you're an investor, you have to have a podcast right now. But podcasts are great for developing relationships you and I are catching up here, it's an excuse to catch up for half an hour an hour. And then other people get to be in your orbit. So I have done 1300 episodes of this week in startups, 80 or so episodes of all in. And so you meet a lot of people, I get to have people on as guests who have invested in already, I get to people have people on as guests who I want to invest in.
And I learned a lot because I have smart people on I asked them basic questions and I listened deeply to the answer. So for me, it's like getting an MBA every year. Uh, so I probably have like 11 MBAs on my wall, just from doing all these meetings. Uh, I'm sorry, all these podcasts and a bunch of people get to sit on them and appreciate it. My Lord, it's like amazing. I go skiing or I go to Miami or, you know, to, you know, uh, my kid's school or whatever and.
Five people will ask for a selfie or bring up an episode or ask to be on the pod. It's a great joy for me, if I'm being honest. It's awesome to meet people. I love people, I love meeting people. So it's absolutely fantastic. And anybody I invest in, in all likelihood will be on the podcast at some point. And so although it's not like guaranteed, it's pretty much guaranteed. Like if your company does well, like I need to have guests on, so at some point you'll be a guest. So just sit tight. And I think people get that.
because they see me have people on the pod who we've invested in. And I say, Hey, I invested in this company. You should know about it. Here's what is why I invested in. Here's an interview with them. And that helps them, right? You've probably experienced that yourself.
slava (52:51.675)
Yep, no, that was super helpful. We're coming towards the end of the episode here, but just a couple of last questions. One, what is the outside of your own content? What do you like to watch, read, or listen to?
jason_calacanis (53:04.642)
Good question. I am, you know, on a purely entertainment basis, absolutely in love with the golden era of television and streaming right now. There's like too many good shows to watch. So my wife and I have, you know, just pick off different shows. And, you know, the Disney stuff has been great with my kids, the Obi-Wan series, the Mandalorian, Book of Boba Fett, the Marvel stuff has been great. And then I love audio books. And I love
slava (53:33.16)
Anyone you would suggest?
jason_calacanis (53:34.95)
Oh my god, way too many to suggest but let's see. I like to be thoughtful about it. I'm looking through what I'm listening to right now. I just listened to putting the rabbit in Brian Cox, the actor's book, putting the rabbit in the hat. It was really good because he read it himself. I love that.
slava (54:01.002)
Nice.
jason_calacanis (54:04.726)
Let's see. Man, I listened to so many of these books, but they're also average. On writing by Stephen King as a writer, I think is like one of the best books on writing I've ever read. Born Standing Up by Steve Martin. Also incredible. Grinding it out by Ray Kroc is an extraordinary one. The person who bought McDonald's and made it into the modern day McDonald's. Bird by Bird by Anne Lamont is another writing book that I love.
slava (54:28.351)
McDonald's, yep.
jason_calacanis (54:34.086)
I'm writing my next book. So it's gonna be about money and wealth. Yeah. So broadly speaking, it's not like how to make money kind of thing, but just about the concept of money. And I really enjoyed there were two books about Netflix, No Rules Rules. And then there was another one by Patty McCord. I can't remember right now, but they were good as like a pairing. I really enjoyed
slava (54:37.491)
What's that gonna be about?
slava (55:02.515)
She was the people officer, is that right?
jason_calacanis (55:04.202)
Yeah, she was a chief people officer, Patty McCord and hers might have been better actually. Slightly better. Kent Langones I love capitalism was very good. He was the investor and famously in that Home Depot, I think. And it says really good to go through these alchemy by Rory Sutherland was quite nice. He's a really interesting cat. The ride of a lifetime with Bob
was very solid, not as good as Michael Ovitz's book, who was Mike Ovitz, but both of them were really interesting. You could hear a theme of, I like biographies. I'm like literally going through my audio. I'm literally scrolling up in my audible right now. And let's see, you know, old school, good to great, was awesome.
slava (55:40.916)
This is great.
jason_calacanis (55:59.422)
get in the game by Nassim Taleb and Black Swan are always classics. I've re listened to some of those his stuff is great. Michael Lewis's stuff is obviously really good. I've enjoyed all of his and I enjoyed also powerhouse which was like the oral history of CIA. So if you pair that with Michael
jason_calacanis (56:29.962)
Uh, Bob Iger, you get a really good history of how, you know, Disney became everything. Uh, it was really good. Um, yeah, I think that's, that's a good group of books to get people started in the Jcal collection.
slava (56:37.375)
Mm-hmm.
slava (56:43.643)
I mean that's, that was 10x more than we usually get, so that was awesome. My last question for you.
jason_calacanis (56:50.378)
Yeah, I mean, I literally for every book I gave you, I scroll past at least 10 or 15. Another good one actually for what we're talking about is thinking in bets by Annie Duke. It might be a little too basic. The poker player, yeah. It might be a little too basic for some people who are into poker, but for people who are venture capitalists who are trying to understand why is poker and venture capital so aligned? It's because making.
slava (56:55.839)
That's good.
slava (57:02.256)
Oh, the poker player.
jason_calacanis (57:14.762)
you know, decisions and putting probabilities on them. So she does, she's a, she's a good writer. She's good at teaching people stuff. So I really liked it. I mean, I really recommend it. Oh, another really good one is the checklist manifesto. And it just teaches you how checklists are really important for discipline, for process, and how checklists help like things like planes stop falling out of the sky in surgery or stop people from killing each other, killing people in surgery.
and working backwards the Amazon principles of like writing first and six pagers and all that stuff I really enjoyed. So, you know, I read notice is very good by Bill Broder. I have like a group of things I like cause they're biographies. I find them inspirational and there's some tactical, and then there are some that are tactical that, you know, you can just apply, you know, piecemeal what you like. So the Netflix books.
were the two Netflix books, Patty McCord and the other one. Those were very good because you kind of really start learning about culture and stuff like that. It's very tactical. Check this manifesto, very tactical, good degree, very tactical. Thinking about it's very tactical. And then there are ones that are inspirational, like Ovetz's, but you can find the tactics within them. And so I find with those two series of books, I can, you know, Stephen King on writing and Born Standing Up by Steve Martin combined with Anne Lamont, Bird by Bird.
you kind of get this like tactical plus storytelling of like, you know, the anecdotes, I really like that combination. When I did my book, Angel, it was a lot of my anecdotes combined with my philosophy. And so by Angel, or get it at your local library for free.
slava (58:48.915)
Perfect, it's almost like using two sides of your brain. Last question, to put you on the spot, and you're gonna say this is an investment advice and we're gonna wanna have a specific idea, which is, that is where I'm headed, which is what would be one investment, and I ask every guest that you would make today or that you would suggest to the audience that they look at making, that they can do today, that we'll look back three years from now, that we think that was a good investment, and it could be anything in any all-terrain investment space.
jason_calacanis (58:54.434)
Okay. Sure. Amazon buy stock in Amazon. Uber. Oh, okay.
jason_calacanis (59:19.506)
All right. So I'm still a very largeholder in Uber and still the company that gave me the most success. I think it's unbelievably undervalued. I'm still very long the company and to the in a network based economy, that the network effects really affect the winner. So if you look at what's happening with Lyft versus Uber, you're starting to see this sort of bifurcation of like, what a network effect can do on either side of the equation. I think that's worth looking at. But putting aside that
Gosh, I can't give you a specific startup because those would all be private. Well, I think, you know, yeah, startups are all, but I am very, I very much like startups. I'll just give a name of one, which you can't invest in because they're privates, but as an example, consumer subscription, which we had great success in com. Com's already a $2 billion company. If you could buy shares in it, you know, I'd certainly tell people to take a look at it.
slava (59:52.479)
But you could do that if you want.
That isn't alt any private company.
jason_calacanis (01:00:17.282)
That'd be a later stage investment, but we have an investment in a company called FitBot as but one example of these consumer subscriptions and it's a fitness app. But it's so well done. And it's so singularly focused that, you know, you don't need a lot of people to build these singularly focused, you know, Netflix of or Spotify of meditation, Netflix, Spotify of working out to really become, you know, highly profitable or
high growth or very stable businesses because they're subscription based. So I think looking at subscription based consumer products, uh, musician is another one we're in. Steezy teaches dance tone based teaches, um, classical music. So that group, I went on a little research project and we found a couple in each category and we really went to town on those. So calm for meditation fit bod for working out Steezy for dance.
musician for popular music and instruments, tone bass for specifically doing classical music, fluent forever for learning languages, you know, all these kind of subscription things that make you better. I didn't invest in masterclass. I thought that's a really interesting company. I wish I had. I passed on the first series. I based on valuation was one of those times it was a miss where like, you know, valuation was too high. I didn't follow up. I should have followed up because I thought it was going to be a one trick pony like
slava (01:01:32.843)
Too hot.
jason_calacanis (01:01:38.53)
The founder knew Dustin Hoffman through his family. Dustin Hoffman did it. And I was like, I discounted that when I should have actually not discounted it. I should have taken that as, oh, he took advantage of an opportunity to build this thing. And then he did, you know, then he got everybody else because he had Dustin Hoffman. I thought, well, like how many times can you do that? Like, does your dad know everybody? And it turned out maybe he didn't need to know everybody because he got Dustin Hoffman. And you know, like Dustin Hoffman doing a class on acting and you know, whatever, it's just extraordinary. So that's a stupid mess again.
jason_calacanis (01:02:08.418)
But you're defined, you don't have to hit everything. And you typically get defined by a small set of winners in your career, especially in the alt and startup investing space. Process, process. It is a great discussion. I really like thinking about my betting strategy. And so I appreciate you taking the time.
slava (01:02:27.611)
Absolutely. Thank you for covering all of this. This has been a great roller coaster of conversation. We covered so many topics. Taurus... No, no, no. This is long for us. I mean, you had some really good sound bites. Taurus season is over. The great repricing is in. Valuations are cut in half. What sounded like a 20 in the early stages now is six to 12. You got in because you like the things like the 16th Tesla or the model signature number one. You target your Goldilocks window.
jason_calacanis (01:02:51.916)
Yeah.
slava (01:02:56.167)
Not too hot, not too cold. You love Equity Crowdfunding, you love the transparency, you love getting put on the big stage. And I can definitely say you use the word process the most of any word on this episode, which is follow the process. If you need some help, get Checklist Manifesto, because that's a book you love. Thank you, Jason, for being on the show. We look forward to having you back.
jason_calacanis (01:03:06.262)
That's what I'm thinking about.
jason_calacanis (01:03:14.302)
I'm Jason on Twitter and Jason on Instagram. If you follow me in those places, I will probably follow you back.
