In short
Summary of This Week in Startups - E1887: Unicorns: Now and Then with Aileen Lee
Podcast Overview Host: Jason Calacanis Guest: Aileen Lee, Founder and Managing Partner of Cowboy Ventures Episode Theme: Discussion on the evolution of unicorns, particularly focusing on Aileen Lee's insights from her original unicorn report and the changes in the venture capital landscape.
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Key Topics Discussed
- Aileen Lee's Background
- Journey in Tech: Aileen discusses her start in venture capital at Kleiner Perkins during the dot-com boom and how she coined the term "unicorn" in 2013.
- Challenges as a Woman in Tech: Overcoming obstacles in a male-dominated industry.
- The Unicorn Club
- Definition of Unicorns: Companies valued at $1 billion or more within 10 years of their founding, primarily in the tech sector.
- Growth in Unicorns: The initial list of 39 unicorns has expanded to 532, with a significant shift toward enterprise-focused companies.
- Shift from Consumer to Enterprise
- Market Dynamics: In the original unicorn list, the majority were consumer-focused. The current list shows 80% are enterprise companies, indicating a market shift toward businesses that offer more capital efficiency.
- Performance Metrics: Enterprise companies are showing higher valuations relative to the capital they raise compared to consumer companies.
- Impact of the ZIRP Era (Zero Interest Rate Policy)
- Investment Surge: Low-interest rates led to significant venture capital investment and inflated valuations.
- Current Market Correction: Discussion on how the market has shifted post-ZIRP, with many unicorns now facing valuation corrections.
- Future of Unicorns
- Predictions on Sustaining Unicorn Status: Aileen estimates that of the current 532 unicorns, approximately 350 may remain valued above $1 billion due to market corrections and performance metrics.
- Zerocorns: Aileen introduces the term "zerocorn" for companies that were once valued over a billion but have since dropped below that threshold.
- Democratization of Founders
- Diverse Backgrounds of Founders: The new cohort of founders is more diverse, with many not coming from traditional tech backgrounds or elite educational institutions.
- Importance of Experience: Aileen emphasizes that prior entrepreneurial experience is crucial for success, as seasoned founders can better navigate the challenges of building companies.
- Governance and Investment Strategy
- Board Dynamics: The importance of having a well-structured governance board and the impact of late-stage investors on company direction.
- Investor-Entrepreneur Relationships: How the dynamic between entrepreneurs and investors has evolved, particularly during the boom and subsequent correction.
- Conclusion and Future Considerations
- Reflection on Privilege in VC: Aileen concludes with thoughts on the responsibility of venture capitalists to foster diversity and address biases in funding.
- Advice for Founders: Encourage transparency with potential investors and emphasize the need for operational efficiency and long-term thinking in building sustainable businesses.
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Key Takeaways
- Unicorn Growth: The dramatic increase in unicorns reflects changing market dynamics, particularly the rise in enterprise companies.
- Sustainability Concerns: Many companies will face valuation corrections, and only a portion will maintain their unicorn status.
- Diverse Entrepreneur Ecosystem: The venture landscape is becoming more inclusive, with a broader range of founder backgrounds and experiences.
- Importance of Governance: Establishing strong governance structures is critical for navigating the current investment climate.
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Related Links
- [Cowboy Ventures](https://www.cowboy.vc/)
- [Aileen Lee on Twitter](https://twitter.com/aileenlee)
- [All Raise - Supporting Women in Venture](https://www.allraise.org/)
- [Aileen Lee's 2024 Article on Unicorns](https://www.cowboy.vc/news/welcome-back-to-the-unicorn-club-10-years-later)
- [Original Unicorn Article](https://techcrunch.com/2013/11/02/welcome-to-the-unicorn-club/)
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This summary captures the main themes and discussions from the podcast episode, providing a comprehensive overview for anyone interested in the latest insights into the venture capital landscape and the evolution of unicorn startups.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00entrepreneurial background, having done something, it doesn't almost matter whether it was jet.com or if it was like a lawn mowing business. It's like basically you have to have tried and have that fire to actually take risk. And failure, I think it's really important. I always tell my founders, getting your ass kicked is a precursor to kicking ass. Yeah. But I do think for the next generation of founders, like for my kids, I encourage them and their friends, like start businesses, talk about business ideas with each other. Why? As a parent, why are you encouraging them that now? The understanding the risk and all the things you just said about hiring, planning out the business, facing failure and disappointment, selling, satisfying customers, all those things.
0:36You kind of need reps. Yeah. And then you get better at it over time. This Week in Startups is brought to you by Ketone IQ is a clean energy boost without sugar or caffeine. Get 30 % off your first subscription order of Ketone IQ at hvmn.com slash twist. The paintbrush loan is the earliest startup financing on the internet. No pitch deck, no business plan, and no warm intros. Plus, you get to keep your equity. Visit getpaintbrush.com to see if you qualify for a $50 ,000 startup loan in less than two minutes. And Coda is the all-in-one doc for teams. Get started for free and get a$1 ,000 startup credit at coda.io slash twist.
1:23All right, everybody, welcome back to the program. Aileen Lee is here. She's the founder and managing partner of Cowboy Ventures. You can follow her on Twitter slash X, Aileen Lee, A-I-L-E-E-N-L-E-E. Thank you, Jason. Welcome back to the program. I don't know when the last time we talked was, but yeah. We've known each other for a long time though. Yeah, it's been, I don't know, 15 or 20 years. Probably, yeah. You knew me before I was investing in companies and I was just an entrepreneur. And back in 2013, you coined the term unicorn. You've done a lot of research on unicorns and you just updated the famous 20 was it the 2013 report you did yeah yeah and so i just wanted to talk to you about all that and then we'll talk a little bit about dei because i know you've been involved in a lot of those efforts here to and you were one of the people will stay tuned for that part and not be like yeah this is my part to check out when you started in the industry um correct me if i'm wrong but when did you start as an investor joined kleiner perkins the end of 1999.
2:21I was about to say it was during the dotcom era. So you've lived through one, two, three cycles now. That's right. I think you actually on X said, or some, didn't you say something about being a three cycle investor? We did a little series here about being a three cycle investor. And it's just so few of them now, because in our line of work investing, a lot of people, you know, if you hit a winner or two, you retire, right? People retire early, or they get aged out. You know, like Bill Gurley is no longer at Benchmark and Doug Leone, Michael Moritz. A lot of folks seem to age out or just, yeah, some firms, I guess, have that in their bylaws.
2:57Yeah. Well, I mean, I think there's different vintages at Sequoia, Roloff, and Alfred and I are similar vintage. Mamoun is similar vintage at Kleiner. So I have a lot of gas in the tank. I'm excited to make more investments. I find this job really invigorating. It's challenging, but it should be. it's an elite pursuit it should be challenging we are in a very important position in society where we get to place bets uh on who gets to you know try and change the world it's pretty heady stuff when you think about it you know it's a privilege for sure yes yeah and then you got vinod coast out here he's in his 70s exactly he's got lots of gas in the tank yeah yeah that dudes they're gonna have to drag him out of the building he's awesome i interviewed with when I was interviewing at Kleiner Perkins.
3:43And I fortunately didn't really know what a big deal he was because I came from Gap. So I didn't really... I had heard of venture capital. I was an analyst at Morgan Stanley in San Francisco office, actually. And the people from banking who went to venture were all guys. And I just figured... And all the people who were hiring them were guys. So I just figured I'd both never get a job and I also would have no friends at work. So I never tried to get a job adventure even though it sounded like such an interesting job and one that i would love so i got lucky when i went to kleiner that i interviewed and i wasn't really intimidated by the folks who interviewed me because i i didn't know they were well and yeah you came into it with the idea that hey maybe i'm not welcome here right um yes and then you were probably correct me if i'm wrong in the 90s in finance there was a bit of gender i was the only investor at kleiner in 99 who was a woman right and when you think about it there were most firms were all male at that time yeah and it managed shockingly changed in the last 10 years with so many women starting firms and all raise the non-profit that's really driven representation in the space but let's talk about unicorns what was the state of unicorns when you first wrote that report we then went through this 10-year crazy period yeah i would say unprecedented but we did have something similar at the end of the dot-com boom, but nothing like this.
5:03So what are the stats now that you've done the report show? Let's get right into the stats. Yeah. So in 2013, I had a relatively new fund. My cowboy's one years old. So basically we had a couple of investments and I had a little more time on my hands. And so I thought, let me just do some research and figure out... Because at Seed, especially back then, but still now, at least for us at Cowboy, it's your first institutional round. So no one's heard of your company before. Many cases, you don't even have a website, right? You haven't even change your profile on LinkedIn. So there's not really signal and you don't have any traction.
5:33So how do I... I moved from being a series A, B, C investor to being a seed investor. So I wanted to learn, if I had started 10 years earlier, what are the best possible companies I could have invested in? And let me make that list and then figure out how could I have found them? Where did they work before? What was the original idea? What did the founders do before? What do they have in common that might give me some sense of signal? And so I basically just started hand curating this list. I was like, well, let me just use reached a billion dollar in valuation in private or public markets within 10 years.
6:01That's pretty good progress. And so that list wound up being 39 companies. I posted it as a guest post on TechCrunch and I came up with a shortener for Unicorn. So it's basically a company, US-based company that's venture backed in the tech sector, less than 10 years old, worth at least a billion dollars in private or public markets. So you're not going to write that over and over again in any kind of report. So I tried to come up with a shortener and home run, monster hit, out of the park. you know like you could and like all of them wound up sounding like both annoying and a little douchey yeah for sure and so yeah totally it just sounds horrible and i think it also um it doesn't convey how special it is how much work goes into it it makes it quite crass and i think pretty empty and so a unicorn was the word that i felt like captured that it's special and kind of rare special and rare for sure yeah it takes a little magic so and then so that report uh back then basically wrote up what they had in common, what I found from the analysis.
6:57And so basically, it was just the 10-year anniversary of that analysis. So this past summer, actually, we said, well, it's going to be 10 years. Why don't we go back into the data and see what we can find? And there just wound up being so many more and so much more to study. It actually took us a couple of months because we went from 39 to 532. The first list was majority consumer. So this is the age of Facebook and Groupon and LinkedIn and Twitter and Airbnb. There were a couple enterprise companies, Workday, ServiceNow being among them. But the 80 % of the value, the aggregate value, if you added up the valuations of all the companies in the list, was consumer and enterprise was a minority.
7:36And so when you look at this new list, the pendulum has swung to enterprise massively. It's 80 % enterprise companies. Wow. So that's a big change. And I should say, we only look at US-based companies. We invest at Cowboy in the US only. And also, it just constrains the list a little bit more. But usually, I think if you're an international listener, hopefully, there are a lot of parallels And the list is probably the US historically in the last decade is about 50 % of the list usually. So it'd be about double, I think, if you were looking at it internationally. So we went from high 30s to 500.
8:07Yep. So 14X. 14X, the number of them. Let's stop there for a moment. What do we attribute that 14X? And then I want to get into sustainability. I don't know if you've gone back and looked at the original 37, was it? Yes, we did. The first 39, we looked at what happened to them. Yeah. So I think that's a really important discussion because it's one thing for us here in the industry to dub something a unicorn, but we all know Groupon and some other companies have had a hard time. Right. I don't know if they're still a unicorn or not, but I know they're still around. So yeah. What does the data show about those original 39?
8:42So the original have had mixed fates. The other thing is 60, I think 66 % of them had exited. So they had either been bought or gone public. So a lot of them like Airbnb, some of the networks affects companies like X, like maybe actually became quite a lot more valuable and Facebook turning into meta. Yeah. A lot more valuable over the past 10 years. And then some of them out of business, not worth nearly what they were before, worth less. So it's definitely a little bit of a mixed bag, but for the most part, the majority are worth more. That is, I think, one of the key realizations Roloff had at Sequoia, which was, or I think Michael Moritz and Doug Leone had it as well.
9:22Man, if we hold on to our companies when they go public, one form of exit. That's right. They did much better as investments after they went public. Now, I don't know if we could say that today because SPACs kind of threw a wrench in there. Some things went out too early. And then we have overpriced companies going public. So on a sustainability basis, that group had a lot of sustainability and staying power. But this new group, that's a big question. Like, did we... Yes, totally. So of those original 39, the enterprise companies tend to have had more consistent performance and held up in value than the consumer companies.
9:55And the other thing that was a big takeaway and might have been to your question about why are there so many more and so many more in enterprise is the capital efficiency of the enterprise companies in the first batch was much higher than the consumer companies. So the consumer companies on average were worth 11 times the amount that they had raised. The enterprise companies were worth 26 times the amount they had raised. Ah, so if we pause there and explain that. That's pretty awesome. Yeah. So they raised a million. Yeah. If you raise a dollar and you wind up becoming worth$26, that's a pretty good return.
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11:40If you raise a dollar in year one, and then you sell the company for$26 in year four, I think that's a 40 % annual rate of return, which especially when interest rates are 1%, you'd much rather get 40 % a year than 1%. I guess one of the big topics during Zerp, money became free. There were lots of funds, lots of investors. people started dipping down into what we do, like Masayoshi-san, you know, and SoftBank or Hedge Funds, Tiger, hedge funds coming down and putting in those last couple of bets. Some of those were perhaps not as efficient, right? Well, not even last. I mean, they started doing A's and B's.
12:16Yeah. And without really being thoughtful about them, I think was, I think the criticism that seemed viable. When you look back on that time, what's the lesson now that we've started to look at the data? What's the lesson from that peak mania, which probably lasted 2019 and 2020 and 2021 and then ended, obviously. A lot of founders at the time, and obviously, this is a conversation because I know you have a lot of experience and points of view on this too. So I think at the time, because there was so much money swishing around in the system, if you had a new... And there was a real war for talent.
12:50So people had more money than people in a lot of cases. So they were like, well, let me solve this with technology. I'll just buy more software. And so a whole bunch of venture-backed software companies found selling their products quite easy. And so everything was, as they say, up and to the right. It's like you start, you sell, and everyone wants it because they've all got fresh venture rounds. And so I think a lot of founders were like, this is not hard. I should just take money. I don't need guidance. I just need money. I'm going to optimize for valuation and build a war chest to scare off competitors because I know exactly what I'm doing.
13:20I've been in business for a year. I got this. And times have changed. so i think a lot of founders out there know that that's not going to be the case for the next five years and so i think the amount of help that you bring on to your cap table early on is going to be you're going to need different help yeah when i was on a couple of boards and i watched these late stage c's and d's occur during that time period you know people asked me what my advice was and i was like well you've already got a board you've already got product market fit this feels like a financial transaction why don't we look why don't you present to the board i said to one founder these five offers you have and just give us a google sheet and put them next to each other what price per share they're paying what terms and what the you know pro forma tap table would look like what would this look like in the case of an exit what would their ownership be yada yada um and just don't even tell us the names of the firms just look at it completely as if you were getting a mortgage do you care when you get a mortgage for your home right if it's you know, from this, you know, firm named after one tree versus another one, Oak tree versus this tree versus that tree.
14:25You probably don't care. Right. You know, which tree it is for that late stage round or for the mortgage. And so they did, I think make some decisions like that. And in some cases they didn't even take board seats, which was. Yeah. Right. That was a weird moment too. Like you're putting a hundred million into this company or 200 million to this company. You're not involved in governance. Maybe you could speak to how governance has changed. I mean, I think that's a, that's a whole nother topic. Uh, Why you're here, Aileen, you've seen this. How lax we got in governance. And I think people now realize that having a board can be a very constructive thing, but who's on your board and what experience they have.
15:02And I think people didn't really want accountability. And so there was a feeling like, don't have a board, just, you know what you're doing, just go for it. But I think we're paying the price now of not having proper feedback or proper dashboards or KPIs or being open-minded to different points of view. And I think when you take on a fund that has... You're one of many bets. And it's a very large fund. And they've got a portfolio. And they are basically... There's a bunch of flowers that they've pollinated. And they just need a couple of them to grow really, really tall. And everything else doesn't matter.
15:38So I think the incentives when you take on money from large funds, you just have to really understand that they want you to have a giant outcome. that you may at that period of time, I think it will change in the coming years. But at the period time, it was like, you know, spend as much as you can get as big as and fast as fast as you can. Let's see if it works. So I can see if I can have the big outcome that I need for my giant fund. I think there's risk associated with that. To your point, if you were to get in on these companies at a billion, 2 billion, 3 billion, and you had any of the ones, you know, from Airbnb over here, and you start seeing the enterprise value of these, and this is the original enterprise value anybody getting in at these and these companies became very large right i mean if you took something like airbnb yeah uh which here was it looks like it's at about three or four billion on this chart yeah that became an 80 billion dollar company uber i don't see it here on the chart alto networks huge huge yeah these are 50 billion uber much bigger yeah there's a lot of folks uh on this chart that have gotten a lot bigger over i mean facebook i think is more than 7x in the past 10 years yeah so you know that's a very important thing to understand about your investor if they are placing you know 30 bets on 30 unicorns you know they're looking for one or two of them to go more than 30x and then they've doubled their returns and that's what late stage investors are looking for and this is where strategics also become problematic or challenging because they don't care about the returns on a financial basis primarily yeah what have you seen in your career with strategics i'm curious uh i mean like a lot of things it's a mixed bag i mean sometimes they can be very helpful uh and with door opening customer introductions validation but then yeah sometimes they they say they're going to be helpful and then they're not they also can screw up and exit potentially yada yada so you have to be thoughtful about where you take the money from.
17:35Now, what's happened to, because you did this at the 10-year anniversary, which means you got those seven years of just up and to the right, but then you got these last two years of everything constricting. So what have we learned about paper corns? Yes. Okay. So that was one of the things that we did. So basically we looked at this new set, wow, there's 532. I think what's really interesting is obviously the 14X, and then also just how many sectors they cover. So when you look at the OG list, as you mentioned, like Meta, right? It's kind of a horizontal company. Anybody around the world can use Facebook or WhatsApp or Instagram.
18:10You've got now all kinds of companies serving many more... In the original list, I don't think there were any healthcare companies. And obviously, enterprise companies were really the minority. In this new list, we basically mapped out 19 different sectors. There are unicorns in logistics, in mobility, in healthcare, in climate, in vertical SaaS, in horizontal SaaS, in HR tech, in learning tech, in ed tech, consumer marketplaces, B2B marketplaces. So they basically fanned out to serve many more sectors and kind of more verticals, if you will, of society, which I think is really exciting. When you think about it, the iPhone is less than 20 years old, which is kind of crazy, right?
18:50Yeah. I think things like the iPhone, where people now have incredible UX and storage, and processing power in their everyday life. Then they got to work and they were like, God, why do I have to wait for this shitty software to load this ugly page? And then I have to click 20 times to get to, or why do I have to use this clipboard and fill it in and deal with these operator errors and people inputting information into mainframe systems? So I think it just basically every kind of business, whether you're a fintech or a doctor's office, people have gotten a lot more comfortable with modern technology and they see how powerful it is.
19:26And so then when a vendor calls and says, hey, I've got the software that can fix your doctor's office and make it really magical and on your phone, they're like, show me more. Yeah, because if you think about it, the expectation of consumers now has risen so dramatically that they're like, hey, this is not as elegant as Instagram. It's not as efficient as Airbnb, you know, or Uber or DoorDash. Yes. I want a DoorDash experience. And if I can get food delivered and a burrito is at stake, well, when my healthcare is at stake, why am I filling out a piece of paper that you're retyping in? This makes no sense.
20:02Or when I'm procuring for my company, why should I wait 60 days to get this order? They've had the Amazon experience. And that's actually is very interesting that it went consumer to enterprise. The consumerization of the enterprise is a theme. Make it easy. Make it simple. Yeah. And then this speaks also to entrepreneurship and the efficiency of capitalism. If you just think about what happened here over the last 15 years or 10 years, when you and I were active and placing bets, entrepreneurs just took those lessons. They saw Uber, Facebook, Instagram, everybody do really well, DoorDash. And they just said, well, where can I apply this?
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21:13Monthly repayment is a flat, predictable amount, which makes cash flow planning really simple. So here's your call to action. If you're a founder in the US, go to getpaintbrush.com to see if you qualify for a$50 ,000 startup loan in less than two minutes. That's getpaintbrush.com to see if you qualify in less than two minutes. And also, I think what was exciting about that is, so it's modernizing a lot of industries that haven't had the benefit of mainstream technology. And when we looked at the founder backgrounds and the geographies, it also democratized quite a bit. So in the original analysis, the majority of founders went to highly selective schools.
21:49And they also worked in tech and they tended to know each other from their tech jobs. Yep. The new founder crop, first of all, we moved from, I think, about 100 co-founders that we were studying the backgrounds of to 1 ,300. Oh, wow. So kind of by definition, you're going to see a lot of change. And so we did. Most of them were not technical. and most of them did not work as a software engineer before. So people, different backgrounds, different schools, the leading market share school for where these founders went to school was Stanford, but it was 5%. Right. So it's a big change. It used to be that VCs would just camp out near the dorms or in the cafeterias at Stanford, just hoping to meet computer science students.
22:29I think that's important, but it's not the majority anymore. And you witnessed that. I mean, John Doerr actually had a famous quote. he said oh yeah i just i i mean it's a cringe-worthy quote now but at the time he didn't mean it in a bad way he's just like listen if you want to be good at venture capital just hang out at stanford like you're saying and you know two or three white dudes come along in khaki pants he was kind of giving them a little bit of a fashion dig but it was true that that maybe was the majority of you know the teams coming out was stanford's computer science or whatever now you've you know i watch um the team at yc that they're obsessed with waterloo you know and yeah other universities that you know really produce great computer science students in israel like it's i mean another topic is immigration we didn't actually it's hard to understand the immigration statics there's a bunch of dimensions whether you're in the military you know like what's your sexual orientation a bunch of stuff that's just obviously very hard to capture but my guess is if we were able to get the data a high percentage of the founders would still be immigrants i know on the first set that was the case.
23:28We didn't see as much progress as I hoped on gender mix for founders. So that's slow. We got a lot of work to do on that. But I think what was consistent was most of the founders were in their mid thirties when they founded their companies. And most teams were co-founding teams of three, both 10 years ago and now. These are two very important facts. There is a bias from people. They think everybody who's going to be successful dropped out of college and they started their company when 19 and 20. Yeah. That's not actually a case. that is a bias that people remember those uh stories because they're such iconic stories whether it's gates or zuckerberg or elizabeth holmes you know it's it's almost like this pattern recognition oh if you quit the ivy league you're dope right so much so that peter teal created an intercepting thing called the teal fellows to try to manifest more of those people and you would expect that from him since he did so well on facebook he literally made a program for that.
24:22But the truth is, people in their 30s who've worked at two or three companies are the ones who create the most value on average. Yeah. And that's actually one of the reasons why I published the first analysis was because in 2013, Mark Zuckerberg was the most aspirational entrepreneur in the world. And VCs were saying, like, I pattern match, I'm a pattern matcher. And basically, I'm looking for white guys in hoodies who dropped out of Harvard, who've been programmed since they're kids, that's who I'm going to back over and over again. And so I was having meetings with founders who had great ideas and they would come in kind of sheepishly and being like, I know I'm kind of old for this, but I just can't stop thinking about it.
25:01And I think it could be a really good business. And it'd be like someone who was 32 years old. And it's like, no, it's great that you have experience and that you can't stop thinking about this and let's have a deep conversation about it. You could be a great founder. So I think that's encouraging. Yeah, I mean, Uber was Travis's third company. Tesla, SpaceX were Elon's third and fourth or second and third. He had Zip2, PayPal, it was a third and fourth. So, you know, pretty obvious there's something like third time's the charm. That exists for a reason. Like, you really start faster because you've all the blocking and tackling.
25:39I mean, really silly stuff, but cap tables, accounting, HR, your first five hires, all of that goes so much easier when it's your third time. That takes two years of mistakes out of the process. I totally agree. And in the first analysis, and in this one, we found entrepreneurial background, having done something, at least one co-founder has started a company, but it doesn't almost matter whether it was jet.com or if it was like a lawn mowing business. It's like, basically, you have to have tried and have that fire to actually take risk. And failure, I think, I wish I could capture or quantify what percentage of the people have had prior failure, but I think it's really important.
26:14Getting your ass kicked. I always tell my founders, getting your ass kicked is a precursor to kicking ass. Yeah, but I do think for the next generation of founders, like for my kids, for example, we have three kids and two of them are girls and I encourage them and their friends, start businesses, talk about business ideas with each other. Why? As a parent, why are you encouraging them that now? The understanding the risk and all the things you just said about hiring, planning out the business, facing failure and disappointment, selling, satisfying customers, all those things. You kind of need reps.
26:44Yeah. And then you get better at it over time. Literally having sold or done customer support at a pizzeria or at my dad's bar, being able to sell people the specials. My dad would be like, hey, veal chop, let's get some of those moving. Wait, where was this? This is in Bay Ridge, Brooklyn. My dad would be like, hey, listen, we got these veal chops. to$36. Like, let's get the double stuffed veal chop going here, you know? And dessert is all margin. Your mom made, my mom would make the chocolate mousse. Chocolate mousse was, and then he had a cappuccino machine, which by the way, in the late 70s, early 80s, to have a cappuccino machine was a very rare thing.
27:18And I remember this was like one of my first entrepreneurial lessons, Aileen. I was in the kitchen and I was watching the dishwasher and the dishwasher would take the espresso cups and he would go like this and he'd say, buck 50. then he would do the cappuccino cup and he would say 250 and he would be counting up how much money my dad was making and he'd be like 275 like tonight on espresso and cappuccinos before starbucks my dad had figured it out and i was just like wow holy cow that's how money works these are unit sales and this press this i have three daughters i am obsessed with teaching them about entrepreneurship i let them listen to the podcast i talked about it and explain it to them and then i started taking my 14 year old to uh parties here in silicon valley and like i just hey what do you do and the person like i work in human resources and culture i'm like can you explain to my daughter 14 what you do here because if they get access to that in this next wave what's going to be left because if you look at chat gpt and you look at like what skill is going to be needed i'm unsure which skill will still be around is being a developer going to be that important in the future it might not be i think being able to learn being curious being able to connect with people and being a critical thinker i think those are like the things that can enable you to morph because yeah the puck's gonna keep moving and we might have called those soft skills right we might have called those like you know oh those are you know the softer skills you need hard tech skills and it's like do you need hard tech skills because this didn't take your study here didn't take into account the international ones.
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28:57But the thing I'm seeing over and over now is the companies on your list, many of them are having more employees outside the US than inside the US. We did a little bit like in the new list, we know I think at least 22 of the companies of the 532 actually have a completely distributed company and no physical office headquarters. That did not exist 10 years ago. And a lot of them are multi-hub. So I think that is completely. I mean, kind of to your early question about like, why did this happen? It was a combination of like interest rates were super low. We had cloud and mobile and security and AI and all these exciting things that were basically giving lots of entrepreneurs ideas and opportunities.
29:39And like you said, it was easier to develop software. It's easier to adopt software than ever. So it kind of made the adoption curve a lot easier. And then we had COVID, right? Where people could work in lots of different places. We were surrounded by technology all day and all night, like we were basically running our work and our personal lives through these new delivery services through zoom and things like that. So it kind of created this perfect storm. But I think it also planted lots of seeds for people to start companies in different places, which is exciting. What do you think about public markets and the stagnation we have there?
30:07What happens to all these companies if they can't get public? What's happening to them now with the paper corns? So let's get back to paper corns. So not indigestion going on in the system. Totally. So another big change in the past 10 years is going from 66 % kind of exited to 93 % of this list being private still. So only 7 % of the companies have had exits. And I think it's only 3 % that have gone public and 4 % were bought. So 4 % were bought. So it's a really tiny percentage. And so 93 % of these companies and 60 % of them are what we call zerbicorns. I was talking to someone this morning, Samir Khadji, he called them, some of them are COVIDicorns.
30:45In other words, that would mean they got very big artificially and then came back down to reality. They raised money when interest rates were really low and public tech companies were flying high and trading at incredible multiples. And there was so much money in the private markets that so much more money had gone into venture capital funds. And they were looking to deploy because they looked at public companies and they're like, wow, tech is a great place to invest. You make so much money. These companies can trade at 50 times revenues. And founders were like, well, this company's trading at 50 times revenues.
31:13I should be valued at 50 times revenues. So a company, well, even more, a company doing$1 million in revenue was raising money at at least a 50 pre during those times. But it was really that time when interest rates were quite low. So 2021 in particular. And so 60 % of the companies on our list basically got their unicorn crowning or valuation during that period of time. Listen, I got a lot on my plate. I got a couple of podcasts I do, you know, all in this week in startups. I run Founder University. Man, we had over 2 ,000 people apply. We got 250 teams in there right now. The list, it goes on and on.
31:51And I'm able to manage it all with an amazing piece of software called Coda, C-O-D-A. It's the all-in-one platform that combines the best of documents with spreadsheets and apps. Here's an example. We use Coda to run our Founder University. Remember I talked about all those founders applying? Well, after they get accepted to the program, every week we ask those founders to submit a progress update. How is your company doing? How's your startup doing? Well, we built this application in Coda, and now we have a database of all those weekly updates. And we can look at all the changes, graphs and charts, all that builds right into Coda.
32:22And this week-to-week tracker has given me the ability to look at thousands of startups we've invested in and invested time in and then pick the best ones to give money to. So if we see strong growth, we invest. And it's certainly changed my world. So if you want a platform that empowers your startup to strategize, plan, and track goals effectively, well, you can get started with Coda for free today. And not only that, they're going to give you$1 ,000 in credit at coda.io slash twist. That's C-O-D-A dot I-O slash twist. Special, limited time only for startups. That means you can start planning and build these apps at no cost right now.
32:55Coda.io slash twist to get started for free. You can't beat that price. Not only is it free, they're going to give you a grand. That's 10 hundies. All right. I love the Coda team. They're constantly giving me new features to make my business more efficient. Thank you to the team at Coda. If you had to guess what percentage of 500 and change would, or raw number, will maintain their unicorn status here? So our prediction, we basically triangulated it a couple different ways. We looked at how are people trading in the secondary markets. So for the companies that we have data on, 40 % of them are trading below a billion dollars in the secondary markets.
33:28Oh, wow. So they're already took the haircuts. Yeah. So that would, well, people who are like, let's say someone who worked at the company who's trying to sell their shares or they're willing to take at least half the valuation. And then the other thing that kind of happened is that the distribution of valuation skewed downwards. So I think 20 % of our list was valued at just a billion dollars. Right. And 40%, I think, is trading at two or below. So if you kind of take those companies and say, well, they probably raised at at least double the valuation that they would have today in today's market.
34:00maybe even four or five times. So you kind of pull those people out of the list. So we basically triangulated a bunch of different ways and said, okay, this list of 532 is probably going to shrink, let's say to 350. But there's a lot of, I mean, 350 is still almost 10X growth from 39. So it's still a huge change. And I think all the things like the moving to enterprise, the number of enterprise companies, the numbers of sectors, the democratization of the founder backgrounds and 10Xing in 10 years is still quite impressive. And the capital efficiency is something I don't think we've talked that much about, but that was the other thing that really fell quite a bit in 10 years that i think is something we have to be pretty careful about yeah and just to look at sectors when we get to capital efficiency i was just ripping through the deck and i said wow oh my god two dozen crypto companies and like coinbase was able to go public but my lord i mean talk about a sector that you know i mean essentially the whole sector has gotten wiped out except for bitcoin solana and maybe coinbase one or a couple of players so you know we silicon valley doesn't always get it right we are capital inefficient in venture and that's part of the magic isn't it uh and i think this is well the risk taking may be the way to say it you know we're so risk taking that i think people who don't understand the job like why would you bet on these companies well because they don't understand the power law yeah there are plenty of companies i think amazon's probably the best example of companies that know that they're losing money and are willing to lose money for a long time because the pot of gold at the end of the rainbow is very big.
35:30And they have a strategy to basically be willing to lose money on categories for up to 10 years because once they get dominant market share, they can start to creep up prices and figure out and work on profitability and margins. And they've washed out the competition. So I think Amazon has been masterful at that. If you look at their history of how much they raised. And I mean, they went public very quickly and they raised a lot of money because that was the only way they could actually access capital. And then they raised a lot of money as a wildly unprofitable company for many years. So this is not saying that every company has to be like Viva, where they got profitable on$4 million and then went on to be worth billions of dollars.
36:11But that is a really great way to build a company that has sustainable value is that you know you're not spending too much on marketing. You know that you're being really efficient with your people. You know you're building and shipping a product that customers like because you have very low churn. You have high margins and a very healthy P &L. So that is, I mean, a really nice, sustainable way to build value. And here's the chart for average capital efficiency. Valuation divided by the equity raise, 2013 versus 2023. Maybe walk us through what we're seeing here with the two bar charts. Yeah. Yeah.
36:43So you can see on the right-hand two bar charts is 2023. and you can see that enterprise companies basically went from 26x to 7x. So basically being worth, let's say if you raised$100 million and you're worth$700 million, that is a big decrease. And enterprise and consumer being the same is kind of very surprising. Because when you look at what's going on in the public markets, I think, didn't Microsoft just pass$3 billion or something crazy? They just dipped above it. Yeah, you're correct. And the Dow hit a high. I mean, to make 7x in 10 years, in many cases, you would have been better off picking a basket of public stocks, which are liquid and freely tradable.
37:23And you can decide every day whether you want to hold or sell versus locking your money up in a private company where you cannot sell freely. So with three decades of experience doing this, having watched three cycles, you come to the conclusion that the industry got too big. There was just too much money chasing too few high quality deals. and so then efficiency goes down. Is that the reasonable conclusion? I wouldn't say, I think quality is so, I mean, there are a lot of quality companies that I think are gonna get screwed up or quality ideas that when you raise too much money and then you can't grow into your valuation, you put yourself in a big zone of risk.
37:59And they might've been quality opportunities that kind of got screwed up by the fact that they raised too much at a high valuation. We lost discipline around valuation because we had like a, I guess, yeah, it was too much demand. There was too much money in the venture ecosystem. in a way it's a boutique business isn't it and well it's not anymore yeah well so then should it be you know or can it be a scale business like you know because it seems like we try to scale this business um or at least the the private equity folks dipping down thinking oh well this is easy i just look at what sequoia and andreason and whoever kleiner have invested in and we just double it and we give the founder more money and we're the next round so we don't have to due diligence.
38:41We don't have to have a board seat. We'll just double or triple their valuation and give them, you know, a hundred million bucks. And that's it. We punched our ticket. That doesn't work. It's, it's funny. Aaron Griffith in the New York Times just published something today about how like everyone always says there's like many times in the history of the tech and venture industry where people are like, there's too much money. It's a bubble. It's going to pop. And like, it just never does. And I have to agree with her. Like I don't, the genie is not going to go back in the bottle. Like we have delivered fantastic returns in the past.
39:08You and I are both very excited and bullish about the power of software. And I think believers of how many more great software companies are yet to be built. And that will deliver great returns for people. And there's still so much money out there that doesn't have venture exposure. There's sovereign wealth funds, there's pensions. I think this is going to be a great time because the next couple, I think people are going to have learned a lot of hard, painful lessons. They're going to be more disciplined in the next five years. Valuations are going to be lower. People are going to raise less and be more disciplined with how they use their money.
39:38So the next vintage is a venture, I think should be much better than the past three years, like the past ventures. So it's going to be a great perspective for people to actually get into venture because we're going to be better. Yeah, this would be the best time to do it. The valuations I'm seeing are the same valuations I saw back when I did Uber and Vemtac and Com and companies with products in markets that are valued in the seed round between five and 15 million, as opposed to 15 and 100 million before they even have products launched. So where do you think the opportunity is? If you were to look at it in venture, you're in seed, I'm in seed and pre-seed.
40:13Then there's Series A, seems super competitive. Series B and C seem to be a commodity. Where is the opportunity in venture today? I think there's opportunity across the board. Okay. I mean, I think at every round there's opportunity. I am a little worried. I've heard from some multi-stage firms that they're just... One guy at a multi-stage firm recently told me he's just doing seed and B, and the fund is a$1.5 billion fund. Like that doesn't make any sense to me. I do think founders, we do a lot of seed, right? And we're telling our founders to just be, a lot of the people who could do A's could also do B's and C's.
40:50And so they've gotten pretty conservative to look at the A and be like, this is kind of promising, but it's not perfectly de-risked. I'll wait for the B and be willing to pay a higher price and invest in a bigger round because I have a really big fund and I'd rather wait and see more cards turned over. And so I think it's creating a little bit of a gap in A. So I think, and A's are, you know, when you're a board member for Series A, you're carrying the water for a long time, you have to be willing to sign up to really be committed to this company for 10 years. We've added a lot of people to the venture business in the past five years, but not that many people who have training to be great board members.
41:23So I'm a little worried about that. But I think there's opportunity across the board. Cowboy, we're very excited to make some new investments this year. I think the founders know that it can be potentially a marathon. And it's not a get rich quick scheme. and they the people who are down for it and they're like i don't care i just really want to help build something substantial that stands the test of time the next three to five years we're going to see tons of great founders like that see this i think is so important we talk about venture tourists there were a lot of people who are trying on being a venture capitalist you really have to have a certain personality for it my friend uh david friedberg got incredibly frustrated running the production board and he's been very public about this i wouldn't speak about it publicly if he hadn't but he's been on a bunch of pockets talking about how frustrated he was trying to get founders to do what he wanted he wasn't and then now he's ceo of his own company again and so and he's much happier because he can come in and make that change the people who you did also have founder tourists people who might have been a great i don't know cto cmo vp of sales whatever it is they would have been a great number three four five on a team and then they were put in the slot and it's not for everybody right and and i think now we're starting to see people who are built for it when i hear your description of the grit tenacity and what people are signing up for that to me is like yeah people who are built for war and let's just face it you know these these companies we've seen it up close and personal they're always on the verge of flipping over going off a cliff even the public ones are you know always uh have somebody looking to disrupt them.
43:02So you need to have a certain amount of grit that maybe we didn't see in the peak era, did we? Another combo is, I mean, there was just a lot more budget five years ago. And then there was so much money that these new venture-backed high-growth companies had in their bank accounts, and they could buy one of everything. And so as we've seen as the recycle investors also, that economies tend to move and go in cycles and enterprise budgets also kind of do. So I think I've seen, you've probably seen this too. It's like you, people used to, there used to be the saying, you never get fired for buying IBM, right?
43:38There were like certain vendors that everyone was like, yeah, it's not the best, but like it's safe. And so people had bought software and they had a rep who had a relationship, but they would buy software from the same vendors over and over again. It was very tight. And then something changes. there's some new technical innovation or something that the incumbents are a little slow to grasp. And some new software companies are like, I've got best of breed for this problem that you're trying to solve. And I've got the new thing that IBM doesn't have, like buy this new package. And then you kind of move into this best of breed cycle where you wind up having a bunch of kind of point solutions or smaller software vendors who solve very acute problems, but then you wind up having a lot of vendors.
44:18And then you might have a security breach or your company misses a couple quarters and you need to get back on financial plan. And where we are right now is because of the refocus on margins and profitability. And because public market multiples are compressed, everyone's cutting, people are cutting budgets, cutting vendors, also their security risks. So the CIO, the CTO, the chief security officer, the CFO, they're all like, hey, we spent way too much. this whole like byo a like bring your own app just like you know sure you can start using dropbox or slack or whatever just expense it like no more right we need too many vendors we need to cut back and so that's a there's a lot of headwinds right now selling to the enterprise big time and so i think to your point about like everyone thought they could be a founder like you have to be a founder who has an idea that actually can break through the headwinds of today's enterprise market yeah the the benchmark is much higher for what people would say you know what we have this built into our office suite over here or we're getting this from google docs or you know notion and coda have this built in you know and i had this happen somebody wanted to introduce a certain project management software that they had and i was like so we got to train 21 people in our venture firm how to use this and we've got to pay per seat and in notion and coda which we're already paying for there's a template for project management and we only have four projects that really need project management right so what are we doing here yeah like just even the idea of stopping everybody's day to have them log into a new piece of software learn it you know forget about the ten thousand dollars just that part to me is what i'm worried about and then you know so let's keep everybody in notion and coda and whatever and that's what we wound up doing and i i see it in my portfolio of enterprise software companies where they're saying yeah we lost this customer why did we lose it oh they loved it the people who are using it loved it but you know the cfl and the cto cio all conspired to say we're going to get rid of we have to get from 20 vendors down to 15 and we were one of five that got cut so the benchmark's higher one of the great things i want you to talk about talent here in the valley um the bay area is just unbelievably magical in terms of the density here i mean people ask me if i could change anything in my life what would i do i might have had a great run in new york city but i might have just come here in the 90s uh that might have been like a better thing for my career to get here a decade earlier or something i think you're doing okay i think i did okay and the kid from brooklyn did okay but um shout out to dara and uber hitting another 52 week high that's like the crazy thing about investing is like i talk to investors like they hit some home run you hit some great company and then they sell their shares and i'm like my thesis about uber has not changed since i made the first bet and i keep getting rewarded for not selling shares just by hanging around and i was talking to somebody who had google shares and another person of facebook shares at a dinner and they both sold their positions and they were just sitting there lamenting like why did i ever sell my positions i know but there's so many counter examples to that yeah people who held on to peloton people who you know just i i love that product so i don't mean to trash talk them i think it's no product is incredible but yeah the valuation did get wonky i do think selling half is like where i've come to i'm very i feel very good about selling half and then putting it somewhere else for safety yeah and putting or putting it on a regular program like every quarter you sell a certain percentage regardless of where the price is yeah and then you could just you have some downside uh protection seems to make sense but the thing i want to talk about was talent here in the valley uh things are much more diverse we have founders coming from anywhere but i do see a correlation between people who come here kind of wanting it more or maybe they're more serious or maybe they're able to deal with more pain or maybe it's a self-fulfilling prophecy you're here and then people projecting to you that you're more seriously and then they invest in you and then you know the flywheel just gets going your top of mind i don't know what it is about this place that's so magical i think it's a super magical place too i will note in our analysis so in our first analysis the bay area silicon valley and san francisco were the hands down winner for being unicorn central right like 70 of the companies were here and all the other geos i think new york had three unicorns and that was like the number two so it's a huge gap between San Francisco and New York, and then everyone else had none, or maybe one.
48:37So that changed a lot. San Francisco lost a lot of ground. We went from 70 % to 45%. Now, the list is a lot bigger. So there's a lot more unicorns in San Francisco, but we lost a lot of ground. And New York jumped to 19%. Wow. It's almost half FinTech, and you showed the crypto slot, crypto on Web3. So we'll have to see how it plays out. And then Denver, Austin, Southern California, Boston, all now more than 10 unicorns. And so I think the Bay Area, I mean, I love it. So I hope we get it. It's an expensive place to live. Public schools are not consistently excellent. Living in San Francisco, my sister lives in San Francisco.
49:15Her car has been stolen and broken into like three times. And we got to clean up our act if we want to be as compelling a place in the future as we were in the past. Yeah, it's definitely the safety, security in the city is an issue. And yeah, the doom loop is very real and yeah the areas around it still doing great but there's not a lot of space here and we're so nimby and anti yeah building housing it's just unbelievable if somebody was like expensive place for if you want to be a teacher or it's like we have a lot of things to fix and so i'm hopeful that maybe people who are paying attention will look at the number and be like we had 70 and now we have 45 we better get on our game yeah i you know watching the people who are very passionate about san francisco the city and because we we live in the wider bay area we say here like there's a bay area and then san francisco is part of it seven by seven mile part of it you know michael moritz and gary tan and his brother and just any number of people in the city who are really committed to changing the political landscape there to maybe have more will to keep up with this change and if not you just you lose the companies to new york which is a dope place to live and Austin, which is also a dope place to live.
50:28And you got a lot more room to move around. And Utah is amazing. Totally. Some of our most valuable companies were not based in the Bay Area and also founders that didn't work in traditional tech. So we love when you're asking about where the opportunity is. I mean, we at Cowboy, we invest a lot pre-product. So founders need the money to actually build the product. We are a great place to call. And also founders who don't come out of central casting. I mean, we invest in both, obviously, and we've got lots of people who are experienced CTOs or came out of Coinbase or Google, but we've had a lot of success investing in people who just have a great idea and have a ridiculous amount of hustle and intelligence and learning mentality, but maybe never worked in tech before.
51:09I was about to ask you what you look for pre-product because you don't have the product to play with. And obviously, if the product doesn't exist, you don't have metrics. So, you know, people who are doing Series A, Series B, they're going to be looking at some early metrics, talking to some customers, seed. You might have product, you might not. You can kind of talk about the product, but pre-product, pre-seed, kind of, what do you look for at that stage? It's a conversation. And I think that's one of the good things about things slowing down a little bit, right? In the boom-boom time when there was so much money, everyone was like, nice to meet you.
51:39Can you tell me this afternoon if you will give me$5 million? Like, that's not, I think, a good way to build a relationship. No. You want to meet over the course of meetings for both sides. It's harder to get someone off your cap table than to get divorced, as they say. Yeah. And so for founders, if you're going to have choices, which hopefully you will, meet your investor a couple different times, ask them questions, do references on them, and see how they handle things. But also for us, we want to see how you process information. We want to understand how you learn. When you are hit with both, what do you figure out when you have very little resources?
52:14How ingenious can you be? Or when you get thrown a curveball, how do you take in the information? How do you respond? Because I think one of the things that we found is we use this term learning animal, the people who we've backed to have actually survived and thrived and scaled also because I think what was really impressive was of the companies that have had exits or, you know, gone public or been bought in the most recent set, similar to the old set, the prior set, it takes about seven years to get to an exit. whether you get bought or go public, but 70 % to 75 % of those founders scaled from being the person with no money and just an idea to being a public company CEO or a multi-billion dollar company leader.
52:49You have to live through so many different phases from basically being an infant to being an adult in all the stages of development over those seven years. It's really impressive. So you're trying to look for both, is the idea innovative enough? Is it going to deliver really significant measurable user or customer value and time and a quick time to value is you know how big is the market uh and then you know the founding dna and kind of the hustle and ingenuity of of the founders are the things that we're looking for you use that term learning machines i think learning animal yeah learning yeah i love it uh because we have one internally because we do also do precede pre-product or while they're in this mvp stage and we say we just we like this product velocity and then people say what's product velocity i'm like yeah well you know when you meet with them last week and then you meet with them this week and they shipped a new product and you saw the app was updated in the app store or you looked at their corporate blog and they had a new blog post up and then this other company was outsourcing you know their tech to some place you know halfway around the world and you know they ship every six months like people who i have some people in the portfolio i've watched them ship you know every couple of days and man the the learning that's right that you become learning animals when you ship because you then hit the customer you yeah you make contact with the ball there's nothing like getting punched in the face or making contact with the ball to to sort of drive learning yeah yeah totally i'm just fascinated by you know people in the early stage and how they try to figure these things out and i too have seen now the funding cycle feels like we're we're back to you know for seed stage you know six 12 weeks of running a process and man is that so much better than six hours or six days it was so weird to for people to say like get off a zoom call and be like are you in and i'm like in what interested i'm interested yeah yeah let's have another call and then i just took the same approach because i i am old school i think like you and they would say like well i have to know today i'd say okay well then obviously the answer is no um but would still love to meet next week can keep hearing about the product and i would just keep the meeting on the books a lot of times i've been watching people are not clearing market so i i i've taken to this um rolol kind of taught me about this not yet kind of thing which is like i like everything you're doing it's a not yet for us yeah and i've been training my team like let's explain to them what we would need to see that's right for the next meeting uh kirsten green told me uh at forerunner they they basically are have COVID taught them to become more transparent with, I think she wouldn't mind me telling you this, with founders about the reasons for not yet.
55:36And so we've been doing the same thing of kind of being like, here's where I'm stuck. And these are the questions I have. Almost like, let us show you what's in our memo. Yeah. And let's work through it together. And through that process, you start to get a feeling of what it would be like to work together and how they think. Ah, this is because you want to have a great relationship. And if the person can handle, hey we're not convinced yet yeah it's a sign of maturity of it and if how they respond to it like you know what you're right we we do need to have a customer that's not a friend of ours we do need to earn a customer through a cold call right that's what i always tell them like i like the two customers you have right now how did you get them and they're like i worked at that company and that's my brother's company yeah i'm like i've seen this trick before you know like with yc companies replicable yeah yc companies had this great trick and one of them explained it to me i said where'd you get these 12 customers like oh it's great you go on to bookface you say that what your company is and then you trade customers so i buy your product you probably might i'm like and they literally explained to me yes that this was like a process that people were and i'm the i'm not i don't want to get into it with the yc founders i don't i'm not saying everybody did this but it was like build your roster of customers through the yc you know ecosystem and it's if you even double click just on but two customers before an investment you'll find this out where did you source this customer and you know look at their link page how many employees so i think some of it is the transparency it's like if the founder tells you right away like look i have these 12 and i did kind of like bootstrap in this way but i learned a lot through the process and i had to start somewhere so here's how i'm thinking about when i cold call someone that i don't have a warm intro to here's how i'm going to do it like that is a great conversation to have but if you pretend like no these you know that then you are starting to be like well this person isn't honest with me about this what else they're not going to be honest with me about exactly and this is where sometimes founders make a mistake the opportunity for us to invest at the early stage is that it's not perfect is that you are figuring it out if you had figured it out you would be raising a series b that's right and we'd be having a totally different comp you know we'd be doing comps versus public market whatever uh let's end on this you know you've been at it for a little bit um and i you know i well listen i i'm saying it out of respect because every time i talk to you i learn something i'm like writing stuff down as you talk it's one of the great things about having a podcast as i get to learn um what and i was i was talking to brian singerman about this like um from founders fund what do you think now that you've watched a couple of different archetypes over three cycles succeed adventure and you're part of the bill gurley analyst mindset i would say right you were an analyst okay well you part you were an analyst right um not like bill girly kind um but i was a financial analyst yes i was an m a analyst okay so yes that requires like creating mental models and architectures and really you know thinking strategically and then of course we have people who are operators and growth hackers and there's relationship people What archetypes really work in venture in your experience that just create massive value for founders and for LPs?
58:50Yeah. I mean, I guess the beautiful thing is I don't think there's one archetype. I did actually, when I was at Kleiner, we were really small. There were eight GPs and three associates. That was the whole firm. And what was really cool about that is we had one partner meeting for everything, whether it was chips or medical diagnostics or routers or consumer internet. So I got exposed to a ton, but all the GPs had a lot of operating experience. And so that was, we had a belief that you kind of had to have walked in the shoes of the operator or the founder. So actually, when I was at Kleiner, I was a partner.
59:23I think I was a GP, but maybe not yet a senior partner. And I had always felt like I was, I had operating experience from working at Gap after business school and before moving to Kleiner, but not like in tech. And so I actually went and ran one of our portfolio companies for two years. It was in between Series A and I actually raised Series B. And it was actually a really interesting time to do it because it was between 07 and 09. Things were really good. I learned a lot because it was enterprise software. I became a sales animal with two twin one-year-olds. I basically lived on a plane. And then we did well enough to raise a$20 million Series B in 2007, which was really big back then.
1:00:01And then 08 hit and I had to lay off half the company. um but we kind of because we had done a kind of financing strategy we had basically conserved all the cash we had a lot of cash in the bank and we lowered our burn significantly and then we wound up acquiring our two closest competitors and then ironically that company went after i left and replaced myself that company went public in spec um but uh but i would say like that's just it's not the same as being uh like a true i had a job at kleiner still so it was a little different than the average uh founder but i mean you see people like martin casado right who was a very successful enterprise infrastructure structure, technical founder, ran a company, now a partner at Andreessen.
1:00:38So I think you've got lots of former operators and former CEOs, and you've got people who basically have been brought up in venture their whole lives. And Michael Moretz, who you mentioned earlier, was a journalist before he became a venture investor. Same path as me. Right? Yeah, exactly. Yeah. So I think all kinds of people can be successful in venture. I don't think there's one answer. The ability to be a learning machine uh seems to be part of it when you look at journalists and what we do or what i used to do like rebecca kate and at union square as an example she was a journalist we have to ask questions and what i what i was trained was you're going to ask these questions you got to look them in the eye and figure out if they're bsing you or not or what the spin is and what the actual truth is and then you got to find other people who you can ask the same questions to and get the same recounting of events yeah and then triangulate the truth and then now you do that i talk to competitors.
1:01:29I talk to customers. You kind of triangulate the truth. That's right. Yeah, totally. So I feel like we're very lucky to be in this job. And I guess we can end with, I think with privilege comes responsibility. So I think we have a lot of opportunity as people with privilege in the tech ecosystem to watch out for its future and to make sure that we do more good than harm. How do you think we need to do better or what should we focus on in that regard? I think we still have a lot of bias. There's still not a lot of diversity. So I think we can do a lot better there. The people who control the big funds and manage most of the money in the industry is still pretty much the same and tend to look for themselves and their successors.
1:02:14But I also think when it comes to obviously AI, I mean, when we look at the impact that social media has had on society, I think we probably could have done a lot better than we did. Absolutely. Yeah. And so for the stuff that's coming down the pike next, I hope we will learn those lessons. Yeah, it's been pretty great to see some change in regards to diversity. I often joke, like when I go to my poker game now, I'm part of like the last white guys at the poker table. We were seeing a lot more diversity. But is it all guys still? And that is part of the challenge. But yeah, at the poker table, yes.
1:02:51You guys have access to great deal flow, lots of insights. When you're trading information or you've got a company that's doing really well and you want to invite people to take a look, just think about who you're inviting and broaden your networks. Yeah. We're on this pendulum now. I don't know if you saw the fearless founders. They got sued. And I was just like, huh, that's interesting. Alice has been sued by the same group. there's this group that basically has a war chest that is going to try and sue the people who are actually trying to make things a little bit better right some past wrongs yeah it's very f***ed up it's very screwed up i'm sorry if uh no it's okay i can just bleep it out put a beep but no it's it's i i thought it was kind of strange to pick like the one tiny you know seed fund that was like you know what there's not enough black women who are funded and they're like you know what we should do we should sue that fund it's like yeah that's why they that is why they did it yes yeah and they want to scare the shit out of people and they should know it is not going to scare us yeah oh and if people want to learn more about that all raise is this incredible organization always.org just check it out i mean if you're a woman who and you want to learn about venture capital you can come to one of these all raise events and hang out with 50 women who have the job already and are supporting the heck out of each other and just telling you how to, you know, basically hack the system or get into it without, you know.
1:04:15Yep. And if you're a man in venture or in tech and you want to be a great ally or you want to hire new people, meet new people, we are also here for you because I think, you know, it's something when we started All Raise, 75 % of venture firms had not a single woman partner. That's wild. Now, I think hopefully to some of our efforts, we're doing better. So now only 65 % of venture firms have not a single woman. But so if you are a founder and you're going to have choices, you can make choices with who you invite to invest in your company. Make money for people whose values you are aligned with.
1:04:44Yeah, I think that is well said. And just go check out allraise.org. It's a great organization to support. And we'll see you all next time on This Week in Startups. Thank you, Jason. Hey, everybody. I talk to a lot of founders here on This Week in Startups and as an investor. And they tell me the same thing over and over again. They want two things from me, more FaceTime and money. They want me to invest in their companies and they want to spend time together. So we've been working here on a new meetup program. We call it Founder Fridays and Founder Fridays are an event by founders for founders.
1:05:18This is an event that is hosted in cities by people like you. If you're listening to This Week in Startups, you're a founder. So what are you going to do at Founder Fridays? You're going to get together with other founders in your community. It could be four or five of you. It could be maybe up to 30 of you in a location. Pick a cafe, pick a co-working space. I like to go to a great Mexican joint or maybe a dim sum restaurant, you know, where you can do shared food, have a couple of cocktails maybe. You do it on a Friday, you get together, and you host it. Now, why is it important for founders to get together?
1:05:48Shouldn't you be at home just focusing? Shouldn't you be in the office just focusing on your startup? Well, if you get together with other founders, true founders who are in the arena, building like you are, you're going to get a lot of value from that because you can trade notes with that other founder about what's working at your startup and what's not working. The truth is, if you're facing a problem, there are hundreds of founders out there who have probably solved it already. And instead of you banging your head against the wall, when you sit there and you talk to three or four founders, you're having some dim sum, you're splitting a quesadilla, some fajitas, somebody's going to say, oh, you know what?
1:06:20I had that same human resources problem. Oh, I had that same technical problem. Oh, I had that same marketing problem. And they might tell you about a tool or a service that'll solve that problem for you. This happens over and over and over again when I do founder Fridays with our portfolio companies. Now we're going to give you that same experience, but here's what I need you to do. I need you to host this in your city. So you're going to go to thisweekinsartups.com slash meetups. That's it. And you'll see a landing page where you can sign up and you can say, I want to host in my city. Now your city may already be hosting, so you can just join that person.
1:06:52And what if you go to this event and you learn some go-to market strategy that 10x is your growth that might unlock funding or you might be talking to somebody and they say hey i'm a marketplace too i'm not a competitive marketplace your marketplace is for used cars my marketplace is for hairstylists whatever your jam is whatever you're working on but they give you some technique that you didn't know about to increase your supply side or get more demand in your marketplace and you 10x your business i see this happen all the time and founders are like mutants right and i'm like professor x here i'm trying to put on cerebro and find all the founder mutants in the world, and then have you get together and do your own little meetup.
1:07:29And here's what you're not going to have to deal with. You're not going to have to deal with a bunch of service providers trying to sell you software or services. And you're not going to have to sit through a bunch of passive speakers. You can listen to This Week in Startups and get the greatest speakers in the world on your own time. And you're not going to have to pay for a ticket to a conference or get on a plane or fly somewhere. No, this is about having an intimate experience with five, 10, maybe two dozen other founders in your city, please go to thisweekinstartups.com slash meetups if you are a founder.
1:08:00This is for founders by founders only. If you are not a founder, this event is not for you. You can start your own meetup for lawyers, accountants, recruiters. This is for founders by founders. We vet everybody to make sure you're a founder. And if you host it, it's a non-commercial event. Our first Founder Friday will start on February 2nd. So please mark your calendars and we're going to do these on a rolling basis. You can join an existing meetup if it's already occurring in your city, or you and one or two other founders can start your own. We're using a wonderful piece of software that we've invested in called River.
1:08:35You can sign up for a River account just by going to thisweekinstartups.com slash meetups. We've already got hosts and attendees lined up in San Francisco, New York City, Toronto, Los Angeles, Las Vegas, London, and even in India. So this is your chance to connect. And if you didn't hear your city name, you can start your city, go to this week in startups.com slash meetups.
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Today’s show: Aileen Lee join Jason to talk about her origins and overcoming challenges as a woman in a male-dominated tech space (2:12), the Unicorn Club and the effects of the ZIRP era (11:51), predictions on which startups will maintain their unicorn status (33:09), and more!
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Read Aileen’s 2024 article here: https://www.cowboy.vc/news/welcome-back-to-the-unicorn-club-10-years-later
Read Aileen’s original Unicorn article here: https://techcrunch.com/2013/11/02/welcome-to-the-unicorn-club/
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Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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