The Exchanges

Q Final, final question for the quickfire round. Hearing that, do you think that actually capital efficiency and aggressive scaling are mutually exclusive, given the fact that one has to kind of peel back, stop scaling, get the business in order before one can regain scaling again, so to speak?

A It can be achieved, but it's pretty difficult, and I'm not sure it's necessary. Like, certainly you never want to light dollars on fire unnecessarily, but in most cases I would say if the land grab reason is strong enough, You shouldn't be concerned about optimizing every dollar spent. Like, if the opportunity is big enough, then you can justify optimizing for speed over IRR on each dollar spent, and I don't think that there's anything to be ashamed about if you're pursuing a big enough opportunity. That being said, I have seen other businesses scale aggressively, capital efficiently, with strong ROI justification, so it is possible. I'd say it's getting harder and harder in a world where everybody's employing the same AB optimization on Facebook, Instagram ads, Google ads, When everybody's employing similar tactics on social referral type marketing and affiliate marketing. So the channels are getting a little bit more saturated and there's still nothing like viral organic growth to feel your business, but I'd say it's getting a little bit more expensive to, to juice your growth through paid channels. And so I'm seeing less and less companies with an ability to hyperscale, you know, while being very ROI driven, I think you can be ROI driven. Wish is one of my best angel investments. And those guys are probably the best performance marketers on the planet. And that company, a lo…

AI assessment note: “It can be achieved, but it's pretty difficult, and I'm not sure it's necessary.”

Q Can I ask, did you have a mentor who, who kind of taught you the fundamentals as you progress through the angel investing?

A Not really. I mean, I would say a bunch of us were just figuring it out together as we went, you know, I kind of started and Hank was separately investing. And so we kind of got going and then we brought a bunch of friends along and a bunch of friends were also just kind of figuring out how to do it at the same time, whether it was Charlie song or Adrian who were up with us in Seattle and starting to invest or the S The angel guys were really the only ones that I, in the very beginning, started that had been doing it for a long time, so they were certainly helpful in giving, you know, me a little bit of personal advice about how to do it and sharing deals, but others like Mike Marquez and Ash Patel at Murado were starting to invest, and, you know, several of these seed funds and friends were doing seed funds, and so I think a lot of us in the industry back in 2010 were kind of starting and figuring it out together. We were kind of a class of vintage behind the Chris Saka's and the You know, two vintages behind the Ron Conway's of the world. Um, so we were able to benefit a bit from what those guys were figuring out in terms of their mistakes and their successes. And in the case of Chris Saka, I figured out that you can create these SPVs and your winners and stuff, but we're all figuring it out as we went. And I think it's continued to evolve tremendously and YC and other others…

AI assessment note: “Not really. I mean, I would say a bunch of us were just figuring it”

Q Can I ask, with so many facets of your career and kind of activities, what would you like your legacy to be?

A You know, I don't really think too much about my legacy. I think about it as I'm very internally motivated. I want to leave it all on the field. And when I die, I want to say that I came as close to reaching and achieving my potential for impact on the world and interesting, rich, rewarding work and interesting, rich, rewarding social and family life as I can. I think legacy, that's a dangerous thing to, to get obsessed with. That's probably why I'll never be Jeff Bezos or someone, someone like that, you know, Bill Gates, who's literally cured a few diseases, you know, with his wife on their own. I'm not as driven by that as I am sort of the personal challenge of I've got some talents, and I'd like to make sure that I leave it all in the field.

AI assessment note: “I don't really think too much about my legacy. I think about it as”

Q Can I ask an off the bat question here, but you said about over allocated to the asset class. How do you think about your own asset allocation today, and has that changed since those early, more enthusiastic days?

A Well, you know, a lot of my close friends laugh at my over allocation because I don't really adhere to the portfolio diversification theory that most people adhere to, which is probably approach. So, I'm basically all cash or Hyper speculative early stage technology equities. And those are either equities that I've earned or kind of created by companies I've started from scratch or, you know, got advisor shares into by helping entrepreneurs get off the ground or the majority of cases, their equity stakes that I've purchased. And the reason that I'm so heavily allocated is first, I'm just so incredibly long on tech. You know, I think that this is a sector that is going to be the greatest source of wealth creation opportunities for the next 50 years as quote unquote software eats the world and yada yada, all the, all the taglines that, you know, your listeners will all be aware of, but also because of two other reasons, which is first, aside from just being bullish, like everyone else who's writing checks into tech, I think I have kind of two different things, which is one, I believe that I have sort of unique deal flow, unique access and unique experience here that gives me an advantage. I've been very humbled by the public equities markets. And so I think I, I know this industry pretty well, and I don't know many other investment areas very well, and so I've always found that j…

AI assessment note: “I'm basically all cash or Hyper speculative early stage technology equities.”

Q with you more on logistics, and Ryan at Flexport from your portfolio is a personal favorite of mine, but I do want to discuss, you mentioned the angel investments there, and it's easy to look at your angel portfolio and the many home runs in it, But I'm intrigued. When starting, how did you think about portfolio construction, check size consistency? Was there an academic kind of thesis around this?

A No, I was the worst ever. I wrote my check into Square straight out of my personal checking account, and then I teamed up with this guy, Hank Vigil, who was one of my mentors at Microsoft. He's a prolific investor and dealmaker, and he was figuring out his next chapter after a long, super successful career at Microsoft. And we were so naive. We just created an LLC, you know, and parked some money in it. Like we, we didn't know anything about fund formation, let alone portfolio construction and tax optimization and you know, how to do, how to do this thing. And so I started off very reactively and just kind of picked up the trade from there was lucky enough to have some wins. And in this business, the more wins you have, the better deal flow and the easier it is to get into deals. And so there's a nice positive reinforcement loop that I and he and others have been able to benefit from, but I had absolutely no idea what I was doing. When I started.

AI assessment note: “No, I was the worst ever. I wrote my check into Square”

Q Can I ask, did you have a mentor who, who kind of taught you the fundamentals as you progress through the angel investing?

A Not really. I mean, I would say a bunch of us were just figuring it out together as we went, you know, I kind of started and Hank was separately investing. And so we kind of got going and then we brought a bunch of friends along and a bunch of friends were also just kind of figuring out how to do it at the same time, whether it was Charlie song or Adrian who were up with us in Seattle and starting to invest or the S The angel guys were really the only ones that I, in the very beginning, started that had been doing it for a long time, so they were certainly helpful in giving, you know, me a little bit of personal advice about how to do it and sharing deals, but others like Mike Marquez and Ash Patel at Murado were starting to invest, and, you know, several of these seed funds and friends were doing seed funds, and so I think a lot of us in the industry back in 2010 were kind of starting and figuring it out together. We were kind of a class of vintage behind the Chris Saka's and the You know, two vintages behind the Ron Conway's of the world. Um, so we were able to benefit a bit from what those guys were figuring out in terms of their mistakes and their successes. And in the case of Chris Saka, I figured out that you can create these SPVs and your winners and stuff, but we're all figuring it out as we went. And I think it's continued to evolve tremendously and YC and other others…

AI assessment note: “Not really. I mean, I would say a bunch of us were just figuring it out”

Q No, I'm adding it to the list, but what motto or quote do you frequently revert back to, Fritz?

A I think it's fortune favors the bold. Like, every time I've had to make a big decision, I've tried to take the Option and just put myself out there. And I think just being in the arena is like a lot of, you know, highly differentiating yourself. Like so many people get held back because of fear of failure and fear of the unknown. And, um, it's always just served me well, especially since I left Microsoft, because I was in the big comfortable cocoon there and had an incredibly rich intellectually stimulating job and financially rewarding job with great colleagues. But, uh, since I left, I've just increasingly taken, you know, bold risks and I've had a lot of Mega face plants, and the resiliency that you develop, the thick skin, the sort of wartime mentality that you drive has made me interested in taking bigger and bigger risks and bolder and bolder bets.

AI assessment note: “I think it's fortune favors the bold.”

Q with you more on logistics, and Ryan at Flexport from your portfolio is a personal favorite of mine, but I do want to discuss, you mentioned the angel investments there, and it's easy to look at your angel portfolio and the many home runs in it, But I'm intrigued. When starting, how did you think about portfolio construction, check size consistency? Was there an academic kind of thesis around this?

A No, I was the worst ever. I wrote my check into Square straight out of my personal checking account, and then I teamed up with this guy, Hank Vigil, who was one of my mentors at Microsoft. He's a prolific investor and dealmaker, and he was figuring out his next chapter after a long, super successful career at Microsoft. And we were so naive. We just created an LLC, you know, and parked some money in it. Like we, we didn't know anything about fund formation, let alone portfolio construction and tax optimization and you know, how to do, how to do this thing. And so I started off very reactively and just kind of picked up the trade from there was lucky enough to have some wins. And in this business, the more wins you have, the better deal flow and the easier it is to get into deals. And so there's a nice positive reinforcement loop that I and he and others have been able to benefit from, but I had absolutely no idea what I was doing. When I started.

AI assessment note: “No, I was the worst ever. I wrote my check into Square straight out”

Q No, I'm adding it to the list, but what motto or quote do you frequently revert back to, Fritz?

A I think it's fortune favors the bold. Like, every time I've had to make a big decision, I've tried to take the Option and just put myself out there. And I think just being in the arena is like a lot of, you know, highly differentiating yourself. Like so many people get held back because of fear of failure and fear of the unknown. And, um, it's always just served me well, especially since I left Microsoft, because I was in the big comfortable cocoon there and had an incredibly rich intellectually stimulating job and financially rewarding job with great colleagues. But, uh, since I left, I've just increasingly taken, you know, bold risks and I've had a lot of Mega face plants, and the resiliency that you develop, the thick skin, the sort of wartime mentality that you drive has made me interested in taking bigger and bigger risks and bolder and bolder bets.

AI assessment note: “I think it's fortune favors the bold.”

Q bad times was his takeaway from that. But I do want to touch on ClassPass today, the incredibly exciting times ahead, because we've seen a period of hypergrowth in recent years, expanding pretty aggressively into the UK, Australia, and 34 other markets, according to my research. I have to ask, how do you think about the right time to really pour fuel on the fire, so to speak, with ClassPass?

A So we're actually up to 50 cities now in four countries, Australia, UK, Canada, and the US, and we are just beginning to pour fuel on the fire again. And so in our case, class passes, the Netflix of studio fitness, but the dream is actually to become the Netflix for all interesting experiences in your life and to go way beyond studio fitness and add gyms and wellness stuff. So you can get massages and cryo treatments, but then even to take it a step further and to connect you to other inspiring experiences, whether that's volunteering at a homeless shelter on a Saturday afternoon to taking your partner on a cool pop-up chef date night thing. Taking your kids to a cool experience, et cetera. So it's a pretty ambitious vision, and so, you know, I think in terms of when you hyperscale, you need to think about a couple of things. The first is, what is the reason to hyperscale? I think there's two reasons, at least in my experience at ClassPass. The first has been competitive. We invented the market. Pyle invented this category of this, this indirect subscription aggregator, and there's been a lot of ClassPasses for XYZ. Well, there were a lot of just straight-up ClassPass clones, and early on in our company's life, I called up the guys, Emil and Travis at Uber and asked them, you know, what is their opinion? We feel like we invented this business model and it was working really wel…

AI assessment note: “in terms of when you hyperscale, you need to think about a couple of things”

Q Can I ask an off the bat question here, but you said about over allocated to the asset class. How do you think about your own asset allocation today, and has that changed since those early, more enthusiastic days?

A Well, you know, a lot of my close friends laugh at my over allocation because I don't really adhere to the portfolio diversification theory that most people adhere to, which is probably approach. So, I'm basically all cash or Hyper speculative early stage technology equities. And those are either equities that I've earned or kind of created by companies I've started from scratch or, you know, got advisor shares into by helping entrepreneurs get off the ground or the majority of cases, their equity stakes that I've purchased. And the reason that I'm so heavily allocated is first, I'm just so incredibly long on tech. You know, I think that this is a sector that is going to be the greatest source of wealth creation opportunities for the next 50 years as quote unquote software eats the world and yada yada, all the, all the taglines that, you know, your listeners will all be aware of, but also because of two other reasons, which is first, aside from just being bullish, like everyone else who's writing checks into tech, I think I have kind of two different things, which is one, I believe that I have sort of unique deal flow, unique access and unique experience here that gives me an advantage. I've been very humbled by the public equities markets. And so I think I, I know this industry pretty well, and I don't know many other investment areas very well, and so I've always found that j…

AI assessment note: “I'm basically all cash or Hyper speculative early stage technology equities.”

Q Final, final question for the quickfire round. Hearing that, do you think that actually capital efficiency and aggressive scaling are mutually exclusive, given the fact that one has to kind of peel back, stop scaling, get the business in order before one can regain scaling again, so to speak?

A It can be achieved, but it's pretty difficult, and I'm not sure it's necessary. Like, certainly you never want to light dollars on fire unnecessarily, but in most cases I would say if the land grab reason is strong enough, You shouldn't be concerned about optimizing every dollar spent. Like, if the opportunity is big enough, then you can justify optimizing for speed over IRR on each dollar spent, and I don't think that there's anything to be ashamed about if you're pursuing a big enough opportunity. That being said, I have seen other businesses scale aggressively, capital efficiently, with strong ROI justification, so it is possible. I'd say it's getting harder and harder in a world where everybody's employing the same AB optimization on Facebook, Instagram ads, Google ads, When everybody's employing similar tactics on social referral type marketing and affiliate marketing. So the channels are getting a little bit more saturated and there's still nothing like viral organic growth to feel your business, but I'd say it's getting a little bit more expensive to, to juice your growth through paid channels. And so I'm seeing less and less companies with an ability to hyperscale, you know, while being very ROI driven, I think you can be ROI driven. Wish is one of my best angel investments. And those guys are probably the best performance marketers on the planet. And that company, a lo…

AI assessment note: “It can be achieved, but it's pretty difficult, and I'm not sure it's necessary.”

Q I'd love for you to kick off today with a little bit about you, so tell me, serial entrepreneur, active angel investor, but how did you make your way into the world of startups, and then second, come to be CEO of ClassPass?

A Yeah, good question. My foray into tech was actually straight out of Undergrad. I was graduating from Yale in the heart of the dot-com crash in, uh, 2003. And, you know, most of the jobs that come to campus to recruit are banking, consulting firms. It wasn't exactly the best time to do that. Microsoft was starting a program to hire undergrads onto the business side, and I was in the inaugural class of that. So I went there, and I was a product manager for a few years, and then I switched into corporate strategy and had a bunch of years doing that at Microsoft. Kind of learned not only how to ship software at scale and a lot about Sort of how you manage business model evolutions, but we also did some fun deals. Like I led the deal team on the Facebook investment that we did way back when in 2007, uh, almost a quarter billion. So it was really that experience of being at Microsoft, leading some investments, getting to know the startup community that then compelled me to become an angel investor. I started writing small checks personally, and then with a partner, a guy named Hank V Hill got pretty lucky with some of the early bets. It was a seed investor in Square and Pinterest and Wish and a couple other great ones. Probably got overconfident, overallocated to the asset class, but ultimately angel investing was what then kind of compelled me to leave and strike out on my own as a…

AI assessment note: “angel investing was what then kind of compelled me to leave and strike out”

Q I'd love for you to kick off today with a little bit about you, so tell me, serial entrepreneur, active angel investor, but how did you make your way into the world of startups, and then second, come to be CEO of ClassPass?

A Yeah, good question. My foray into tech was actually straight out of Undergrad. I was graduating from Yale in the heart of the dot-com crash in, uh, 2003. And, you know, most of the jobs that come to campus to recruit are banking, consulting firms. It wasn't exactly the best time to do that. Microsoft was starting a program to hire undergrads onto the business side, and I was in the inaugural class of that. So I went there, and I was a product manager for a few years, and then I switched into corporate strategy and had a bunch of years doing that at Microsoft. Kind of learned not only how to ship software at scale and a lot about Sort of how you manage business model evolutions, but we also did some fun deals. Like I led the deal team on the Facebook investment that we did way back when in 2007, uh, almost a quarter billion. So it was really that experience of being at Microsoft, leading some investments, getting to know the startup community that then compelled me to become an angel investor. I started writing small checks personally, and then with a partner, a guy named Hank V Hill got pretty lucky with some of the early bets. It was a seed investor in Square and Pinterest and Wish and a couple other great ones. Probably got overconfident, overallocated to the asset class, but ultimately angel investing was what then kind of compelled me to leave and strike out on my own as a…

AI assessment note: “angel investing was what then kind of compelled me to leave and strike out”

Q Can I just interject there and say, where do you find startups most to draw your help and require it? Are there commonalities?

A Three areas. One is general strategy because I, you know, led a corporate strategy team at a big tech company that had 17 different billion dollar businesses. So I'm never going to be as good as somebody who's such a domain expert as a founder in their area, but I can kind of bring framework thinking, structured thinking, and pressure test their assumptions and see if I can help identify any gaps in their logic or theses. The second is typically on fundraising, and this industry always says we shouldn't celebrate financings, and I say bullshit to that. The reason is that a financing is a lagging indicator of whatever you've done over the last six, 1218 months, and so it's a reflection that you did something good, that you made some good progress and momentum. The second reason why I celebrate financings is because Half of the battle is just earning the opportunity to play the game. And it's like the hedge fund private equity industry, or even VC for the last 30 years. Like, if you were just in the asset class, you were going to do well. If you had a bunch of other people's money stacked behind you on a two, two percent management fee, 20% carry investing structure. Like, you didn't even have to be that differentiated that much better. You know, and as Warren Buffett and others have pointed out on the hedge fund side, you know, you didn't even really have to beat the S&P 500 or …

AI assessment note: “Three areas. One is general strategy... The second is typically on fundraising”

Q Can I just interject there and say, where do you find startups most to draw your help and require it? Are there commonalities?

A Three areas. One is general strategy because I, you know, led a corporate strategy team at a big tech company that had 17 different billion dollar businesses. So I'm never going to be as good as somebody who's such a domain expert as a founder in their area, but I can kind of bring framework thinking, structured thinking, and pressure test their assumptions and see if I can help identify any gaps in their logic or theses. The second is typically on fundraising, and this industry always says we shouldn't celebrate financings, and I say bullshit to that. The reason is that a financing is a lagging indicator of whatever you've done over the last six, 1218 months, and so it's a reflection that you did something good, that you made some good progress and momentum. The second reason why I celebrate financings is because Half of the battle is just earning the opportunity to play the game. And it's like the hedge fund private equity industry, or even VC for the last 30 years. Like, if you were just in the asset class, you were going to do well. If you had a bunch of other people's money stacked behind you on a two, two percent management fee, 20% carry investing structure. Like, you didn't even have to be that differentiated that much better. You know, and as Warren Buffett and others have pointed out on the hedge fund side, you know, you didn't even really have to beat the S&P 500 or …

AI assessment note: “Three areas. One is general strategy... The second is typically on fundraising”

Q bad times was his takeaway from that. But I do want to touch on ClassPass today, the incredibly exciting times ahead, because we've seen a period of hypergrowth in recent years, expanding pretty aggressively into the UK, Australia, and 34 other markets, according to my research. I have to ask, how do you think about the right time to really pour fuel on the fire, so to speak, with ClassPass?

A So we're actually up to 50 cities now in four countries, Australia, UK, Canada, and the US, and we are just beginning to pour fuel on the fire again. And so in our case, class passes, the Netflix of studio fitness, but the dream is actually to become the Netflix for all interesting experiences in your life and to go way beyond studio fitness and add gyms and wellness stuff. So you can get massages and cryo treatments, but then even to take it a step further and to connect you to other inspiring experiences, whether that's volunteering at a homeless shelter on a Saturday afternoon to taking your partner on a cool pop-up chef date night thing. Taking your kids to a cool experience, et cetera. So it's a pretty ambitious vision, and so, you know, I think in terms of when you hyperscale, you need to think about a couple of things. The first is, what is the reason to hyperscale? I think there's two reasons, at least in my experience at ClassPass. The first has been competitive. We invented the market. Pyle invented this category of this, this indirect subscription aggregator, and there's been a lot of ClassPasses for XYZ. Well, there were a lot of just straight-up ClassPass clones, and early on in our company's life, I called up the guys, Emil and Travis at Uber and asked them, you know, what is their opinion? We feel like we invented this business model and it was working really wel…

AI assessment note: “when you hyperscale, you need to think about a couple of things”

Q start with something that Adrian Ioun said on the show recently, and he said that it's phenomenal to be on the other side of the table and see how investors act behind the scenes. I'm intrigued, given your kind of operational in the trenches stance today, how have you seen investors act on the other side of the table when you're co-investing with them? Have there been some learnings there?

A There have, but I think if you're playing with reputable investors, and again, you kind of figure out who Has similar style and culture as you. And cause as an angel, you know, our business is dependent on having these great alliances with many different types of investors. And part of my proposition is that I can help a founder build their cap table with the right investors. So certainly you kind of learn a lot about investor psychology and you learn how to read when you're raising money yourself, you learn how to read an investor better and you know, how interested they are. You can read their concerns pretty well. And certainly it's made me better at pitching because I think about what is the investor? How do you create your thesis as an investor? And how do I answer those talking points? Adrian sounds like he was alluding to some bad behavior, which certainly I hear about a lot. I've seen on very seldom occasions. And you know, the people that I co-invest with don't sort of adhere to those types of practices.

AI assessment note: “certainly you kind of learn a lot about investor psychology”

Q start with something that Adrian Ioun said on the show recently, and he said that it's phenomenal to be on the other side of the table and see how investors act behind the scenes. I'm intrigued, given your kind of operational in the trenches stance today, how have you seen investors act on the other side of the table when you're co-investing with them? Have there been some learnings there?

A There have, but I think if you're playing with reputable investors, and again, you kind of figure out who Has similar style and culture as you. And cause as an angel, you know, our business is dependent on having these great alliances with many different types of investors. And part of my proposition is that I can help a founder build their cap table with the right investors. So certainly you kind of learn a lot about investor psychology and you learn how to read when you're raising money yourself, you learn how to read an investor better and you know, how interested they are. You can read their concerns pretty well. And certainly it's made me better at pitching because I think about what is the investor? How do you create your thesis as an investor? And how do I answer those talking points? Adrian sounds like he was alluding to some bad behavior, which certainly I hear about a lot. I've seen on very seldom occasions. And you know, the people that I co-invest with don't sort of adhere to those types of practices.

AI assessment note: “you kind of learn a lot about investor psychology and you learn how to read”

Q truly next rich vein to explore. I'd love to hear, given kind of your excitement around the Facebook deal, and really some of the Stellar Angel investments that you've made kind of in the space, how would you respond to this suggestion from Elad on the end of this tech cycle, maybe considering Snap being one of the biggest and most recent consumer exits now quite a long time ago?

A That's true. You know, I talk a lot about the veins of innovation and looking at companies that correspond to them. I used to be a thesis driven angel investor where I would come in and I had a thesis about a given sector and I'd look for a company that fits that thesis and then I'd invest in it. But I very quickly learned that it's too hard to model the world and all of the potential opportunities. And so many of my best angel investments ended up being in spaces that I knew little to nothing about. I mean, my first one was square and I had looked into payments a bit for Microsoft because, you know, we had so much cash in the balance sheet that one of the things we could have done was become a bank. And we could have gone after digital currencies and stuff. And we had really interesting conversations about that, but ultimately I didn't know much about the space and I met Jack and decided how many chances in your career do you get to bet on somebody like that? And so, you know, I kind of made that bet without really understanding the payments industry or Pinterest is another example where I had never been using catalogs and stuff. I'd collected butterflies as a kid and done some of these things that I think work well in terms of this digital form of Pinterest, but really it was only until I went to my wife and And saw her as one of the very first users of the product because I …

AI assessment note: “That's true. You know, I talk a lot about the veins of innovation”

Q truly next rich vein to explore. I'd love to hear, given kind of your excitement around the Facebook deal, and really some of the Stellar Angel investments that you've made kind of in the space, how would you respond to this suggestion from Elad on the end of this tech cycle, maybe considering Snap being one of the biggest and most recent consumer exits now quite a long time ago?

A That's true. You know, I talk a lot about the veins of innovation and looking at companies that correspond to them. I used to be a thesis driven angel investor where I would come in and I had a thesis about a given sector and I'd look for a company that fits that thesis and then I'd invest in it. But I very quickly learned that it's too hard to model the world and all of the potential opportunities. And so many of my best angel investments ended up being in spaces that I knew little to nothing about. I mean, my first one was square and I had looked into payments a bit for Microsoft because, you know, we had so much cash in the balance sheet that one of the things we could have done was become a bank. And we could have gone after digital currencies and stuff. And we had really interesting conversations about that, but ultimately I didn't know much about the space and I met Jack and decided how many chances in your career do you get to bet on somebody like that? And so, you know, I kind of made that bet without really understanding the payments industry or Pinterest is another example where I had never been using catalogs and stuff. I'd collected butterflies as a kid and done some of these things that I think work well in terms of this digital form of Pinterest, but really it was only until I went to my wife and And saw her as one of the very first users of the product because I …

AI assessment note: “That's true. You know, I talk a lot about the veins of innovation”

Q No, I'm absolutely with you. Public expertise gives me goosebumps, but I do want to slightly delve back into the world of serial entrepreneurship that you slightly touched on there from founding Livestar and Doppler. I'd love to hear what were some of the big takeaways that both worked and maybe didn't work? That you've taken with you to today as CEO of ClassPass?

A Too many humbling lessons across my various entrepreneurial ventures. So, ClassPass is my fourth company. It's the only one that I wasn't, that I've operated that I wasn't a co-founder in. My partner Pyle and her partners had gotten the company off the ground, and I led the seed round when the company was pivoting from a previous incarnation into ClassPass. And then I, six months later, led a Series A for the first and only time into the company. And became the chairman. And that was really a way for me to kind of buy a piece of the business to justify becoming a chairman, becoming really the extra, the new partner for the founders who then pile ultimately asked me to step in and operate the business because our skill sets were very complimentary. And as the job was getting bigger, she was spending less time doing the things that she wanted to do. So this one kind of worked out nicely in terms of the previous three were live star, which was sold to Pinterest Doppler, which was not exactly a great outcome, which was well publicized. And can read about Wired Magazine. Did a big deep dive on kind of how that company, which was very hot, very promising. We built a lot of really cool stuff, how it didn't work. And then the third was a company called Download, which pivoted into reverse, which was Greylock backed, which was picked up by Dropbox. So the lessons as an entrepreneur, you…

AI assessment note: “my operating of startups has actually made me a much sharper investor”

Q No, I'm absolutely with you. Public expertise gives me goosebumps, but I do want to slightly delve back into the world of serial entrepreneurship that you slightly touched on there from founding Livestar and Doppler. I'd love to hear what were some of the big takeaways that both worked and maybe didn't work? That you've taken with you to today as CEO of ClassPass?

A Too many humbling lessons across my various entrepreneurial ventures. So, ClassPass is my fourth company. It's the only one that I wasn't, that I've operated that I wasn't a co-founder in. My partner Pyle and her partners had gotten the company off the ground, and I led the seed round when the company was pivoting from a previous incarnation into ClassPass. And then I, six months later, led a Series A for the first and only time into the company. And became the chairman. And that was really a way for me to kind of buy a piece of the business to justify becoming a chairman, becoming really the extra, the new partner for the founders who then pile ultimately asked me to step in and operate the business because our skill sets were very complimentary. And as the job was getting bigger, she was spending less time doing the things that she wanted to do. So this one kind of worked out nicely in terms of the previous three were live star, which was sold to Pinterest Doppler, which was not exactly a great outcome, which was well publicized. And can read about Wired Magazine. Did a big deep dive on kind of how that company, which was very hot, very promising. We built a lot of really cool stuff, how it didn't work. And then the third was a company called Download, which pivoted into reverse, which was Greylock backed, which was picked up by Dropbox. So the lessons as an entrepreneur, you…

AI assessment note: “The lessons as an entrepreneur, you know, you learn a lot.”