The Exchanges

Q What can you do to enforce exercise routines? I've followed you on Snap. I've followed you on Instagram. Exercise is core of your life. What do you do to enforce the routines?

A That's a great one. I work out every day. And so what's worked for me Is if you read this book called Atomic Habits by James Clear, it's a pretty good book. The streak tracking mechanism has worked really well for me. So I have a streak app on my phone. It's called streaks. And every single day I have to check off workout and I just need to do it, like do something. Even if it's like 60 pushups, I just do one thing a day. And I think my long, my streak has been going for 25 days now. Worked out 25 days in a row. Be a bunch of different things from lifting to yoga to Getting on my running machine, but every day I want to do something. And now, you know, if I don't do it one day, I'm like, well, I have to abandon this 25 day streak I've invested in. That's like, like horrible to me. So I'll just get down and like do my 60 pushups or whatever. So the streak psychology, I think that's worked incredibly well for me for exercise.

AI assessment note: “The streak tracking mechanism has worked really well for me.”

Q I do want to talk about that because it relates to something that you said before, which is kind of attaching yourself to outcomes will only cause your own suffering. What do you really mean by this? And does this disregard maybe for attachment to outcome? Does that not go against what we're always told about the mission and vision of having that real North star stay with your company?

A Yeah. So it sounds at a surface level, like a contradiction. I'll say to Harry that I'm also similarly have Always been driven by these external outcomes and trying to achieve them. And so I think I've had a very similar path to what you've experienced. The way I think about it is that basically the idea that you can drive lasting happiness from something that happens externally, like some sort of milestones, whether it's number of subscribers, amount of revenue, valuation, exit, those events are always fleeting and just you re-normalize them as the new normal once they occur. So, you know, when we sold Twitch, Almost a billion dollars. Like I was very happy for one day, two days, even a week. But after that, I was just, I remember, you know, kind of just went, okay, that's the new normal. And now I'm back here at my baseline. The way I think about it is if you expect yourself to be have lasting happiness driven by an outcome in the future, two things. One, you won't actually change your baseline when you get it. But more importantly, number two, you will accept unhappiness in your present. And you'll kind of say like, that's normal. And the problem with that is that will create an unsustainable situation for you. And I think that's the reason why you shouldn't do it. People think that it's contradictory to actually having a goal, which is not what I'm saying. I think that as a…

AI assessment note: “People think that it's contradictory to actually having a goal”

Q I do want to talk about that because it relates to something that you said before, which is kind of attaching yourself to outcomes will only cause your own suffering. What do you really mean by this? And does this disregard maybe for attachment to outcome? Does that not go against what we're always told about the mission and vision of having that real North star stay with your company?

A Yeah. So it sounds at a surface level, like a contradiction. I'll say to Harry that I'm also similarly have Always been driven by these external outcomes and trying to achieve them. And so I think I've had a very similar path to what you've experienced. The way I think about it is that basically the idea that you can drive lasting happiness from something that happens externally, like some sort of milestones, whether it's number of subscribers, amount of revenue, valuation, exit, those events are always fleeting and just you re-normalize them as the new normal once they occur. So, you know, when we sold Twitch, Almost a billion dollars. Like I was very happy for one day, two days, even a week. But after that, I was just, I remember, you know, kind of just went, okay, that's the new normal. And now I'm back here at my baseline. The way I think about it is if you expect yourself to be have lasting happiness driven by an outcome in the future, two things. One, you won't actually change your baseline when you get it. But more importantly, number two, you will accept unhappiness in your present. And you'll kind of say like, that's normal. And the problem with that is that will create an unsustainable situation for you. And I think that's the reason why you shouldn't do it. People think that it's contradictory to actually having a goal, which is not what I'm saying. I think that as a…

AI assessment note: “People think that it's contradictory to actually having a goal, which is not what I'm saying.”

Q infrastructure around it, which, which makes it partly so incredible. I do want to touch on one element where we chatted before, because a lot of guests on the show said to me, I've got to read the school takes care of itself. And you mentioned it before the episode. What were your big takeaways from reading the school takes care of itself that really kind of stayed with you?

A Yeah. The one that stayed with me a lot is that Bill Walsh was so successful, but then he just burned out and it's almost like a cautionary tale. And that really resonated with me. You can be burned out no matter how successful you are, and you can be unhappy no matter how successful you are. And that's something that I have experienced. A lot of times when you are early on in your career, or even in the middle or even late stages of your career, you think, if I just get to this other milestone, X, you know, I have a billion dollar company, I have a two billion dollar company, I have a, you know, or I get a VP title and my job or whatever it is. Right. You think you'll finally be happy and you know, you kind of accept unhappiness in the present, but the problem is that that's not like a sustainable strategy for actually achieving happiness. And if you're not happy, you will not want to do what you're doing for an extended period of time. And I think that's actually very toxic in startups because in startups, you are a very important actor as the founder or, and or CEO of your company. You are a very important component. And if you burn out, you are not doing yourself or your investors or your employees or your customers any favors. You need to like retain yourself. And so you need to create a situation inside your company where you are going to be retained for a long time. I th…

AI assessment note: “The one that stayed with me a lot is that Bill Walsh was so successful”

Q things that jump out to me from there and and one of them most definitely is the interview process you mentioned in 2005 going pitching uh and talking about applications uh with your co-founder how have you seen the interview process then change at yc i've seen your snap Chas, uh, you, you do a lot of, uh, YC interviews now. How's the process changed over the 11 year period?

A So the interviews when they started off were 40 minutes long, which I'm sure to the interviewers felt exhausting. Uh, now they're only 10 minutes long and they still feel exhausting. However, I think they're actually pretty similar, which is three or four partners in a room asking questions about the business to the entrepreneurs. You know, questions like, Why are you starting this company? And what's your insight here? And then digging into the model or digging into product and trying to determine are these the people that are going to take this product to be a multi-billion dollar company? You know, it's, it's a shorter amount of time, but it's, uh, the same process pretty much since, since the beginning. I think PG and Jessica and Trevor and Robert got a lot of things correct in the beginning. Uh, you know, the interviews, uh, Funding companies as a cohort, uh, demo day, um, doing these like weekly check-ins through weekly, you know, kind of this weekly dinner. So there was this heartbeat of, uh, of your company in the early days. I think all those, you know, were key insights in the beginning that have persisted to the till until today.

AI assessment note: “interviews when they started off were 40 minutes long... now they're only 10 minutes long”

Q things that jump out to me from there and and one of them most definitely is the interview process you mentioned in 2005 going pitching uh and talking about applications uh with your co-founder how have you seen the interview process then change at yc i've seen your snap Chas, uh, you, you do a lot of, uh, YC interviews now. How's the process changed over the 11 year period?

A So the interviews when they started off were 40 minutes long, which I'm sure to the interviewers felt exhausting. Uh, now they're only 10 minutes long and they still feel exhausting. However, I think they're actually pretty similar, which is three or four partners in a room asking questions about the business to the entrepreneurs. You know, questions like, Why are you starting this company? And what's your insight here? And then digging into the model or digging into product and trying to determine are these the people that are going to take this product to be a multi-billion dollar company? You know, it's, it's a shorter amount of time, but it's, uh, the same process pretty much since, since the beginning. I think PG and Jessica and Trevor and Robert got a lot of things correct in the beginning. Uh, you know, the interviews, uh, Funding companies as a cohort, uh, demo day, um, doing these like weekly check-ins through weekly, you know, kind of this weekly dinner. So there was this heartbeat of, uh, of your company in the early days. I think all those, you know, were key insights in the beginning that have persisted to the till until today.

AI assessment note: “when they started off were 40 minutes long... now they're only 10 minutes long”

Q after the demo day. Uh, I've been lucky enough to attend the demo day, uh, recently, actually the last one, and they're very considerable now, stretching several days. Uh, so I want to talk about batch sizes and scaling YC in terms of sheer number per batch. So how do you approach the scaling of batch in terms of retaining the same quality of mentorship and tuition within each batch?

A So you might've heard from other partners, but we shard YC. Uh, we have four different groups at YC. I, uh, run one of the four groups with Adora and Kasser right now. So we have three group partners in my group. They are kind of the first line of defense for our companies, which is, you know, somewhere between 26 and 30 companies. Our companies, you know, basically if they have questions about fundraising or hiring, you know, getting the product market fit, come to us first. It feels like a much smaller, it's like a business school section, I guess. Um, Like a smaller group that you can, you know, more intimate and a long connection with your partners.

AI assessment note: “we shard YC. Uh, we have four different groups at YC.”

Q I totally agree with you. And you said that about the ego element, and I actually got told by someone the other day, they said, Harry, you're so enraptured with what you do that you've almost become the company and you're not the company and you have to segregate yourself. How do you think about detachment from self and company and you are not your company, so to speak?

A Yeah. I think it's really hard for entrepreneurs. I remember in the early days of Justin TV, I would see my friends posting on Facebook. They'd be like, Oh, I'm having fun. I'd like, and the summers, especially going on vacations and I'd be sitting in our office programming. What am I doing with my life? The thing I told myself was at least I'm an entrepreneur and I have my own company. They might be getting paid more and on a career trajectory and actually having fun, but at least I have my own company and you know, I'm an entrepreneur. And so my entire identity was wrapped up in my company. And being an entrepreneur. And so the problem with that is that when things go badly, you feel badly about yourself. You transpose those feelings that you might have about what's happening in your company onto yourself. And that's a recipe for being depressed, feeling super bad every day, and ultimately burning out and quitting, which doesn't serve the interest of your company. And so I think that's the way to get out of that. Well, I don't think I have all the answers, but some of the things that have worked for me are Really focusing on your own mental health and wellbeing. I have a timer on my phone every day that actually reminds me to meditate on attachment specifically and to remind myself that, you know, if I achieve the thing that I want, I think I want, actually, I'm not going to …

AI assessment note: “meditate on attachment specifically and to remind myself that”

Q I do want to ask one thing is, when we chatted before, you said about the analogy of a board game, especially to the attachment thinking. Can I ask what's the analogy of the board game for everyone listening? I thought it was a fascinating one.

A Sure, so people are like, why, what's even the point then, Justin? Like, if there's no point in having these goals, or if you don't, like, really care about the goals, then what's the point of existing or having goals or doing anything? And the way I think about it is, I kind of think about like your goals in life or your company or as an entrepreneur or even your entire life as playing a board game. You know, you can imagine a rainy Saturday afternoon. I'm saying rainy because you're in London and I'm in San Francisco, so it's probably rainy. And then playing a game, you, your friends come over and you play this, break out this board game. And when you're playing the game, if you're like me, you're really engaged in it. You know, you're paying attention. It's engaging your mind. You're like, how do I make a strategy that's going to win? Talking about one of these, you know, fancy German board games, like settlers of Catan or something, not monopoly, but you're really trying to engage, be engaged in winning and you want to win and you try your hardest. But then when you put away the game, you know, the game's over and the next week, do you remember or even care what happened? Not really. You know, you accept it's in the past. It's actually not that big of a deal. And that's kind of how I think about how you should approach all of your goals and situations and circumstances in l…

AI assessment note: “kind of think about like your goals in life... as playing a board game”

Q it your air tables, be it your zooms of the world. And PG wrote a phenomenal piece about why this is such a great business and business model to operate. I'm really interested. How do you think about actually when the majority of your customer base and customers are Similar to you, high growth tech companies. And do you think that really is a viable model over the long term?

A That's a good question because, you know, there is a question of, is this, where are we in the business cycle? And if all, you know, if there's a downturn, do all these companies go away or they start cut costs? I think that when I was thinking about selling or building a company that sold Startup community for a long time, you know, had the YC connections and other investor relationships in Silicon Valley. Atrium itself has raised money from over a hundred VCs and angel investors in Silicon Valley. So I felt like that would be a really good initial bootstrap to get access to a lot of different potential customers, which it was. So it kind of made sense for where I was in my career. And obviously it was a really quick way to get out the gate. I do think that with legal specifically, it's one of those things that it's really, you know, you use it in good times and use it in bad times. That's part of what attracted me actually to this industry is that I was a customer, a client of legal over my 15 year entrepreneurial investor career. And, um, I'd use kind of legal services no matter what was happening, whether they were, you know, it was good or bad, or like, you know, no matter what you want to do in America and in business, you end up, it's a big transaction. You end up paying attorneys, whether it's, you know, selling your company or raising money or signing a major commercia…

AI assessment note: “I do think that with legal specifically... you use it in good times and bad”

Q in such a close-knit society that we have in terms of the tech ecosystem, do you think you really can be as transparent as, you know what, We're kind of fucked. We just lost our biggest customer and our head of sales just left because we live in a fundraising ecosystem. We live in a momentum-based society. Do you think transparency is possible given the tight-knit nature of the ecosystem?

A Yeah, you know, that's really hard, and I think that what's important is that people who can take risks, take risks publicly so that people can see that behavior, and we move the bell curve more towards, you know, normalizing vulnerability, and so that's something that I try to model when I And even I can't advertise like super things that might be perceived as super negative events. It's really tough to do in our society. And so I think another important thing is for people to form a group, form connections, people around them that can be where they can be really truly vulnerable. You know, you might not be able to do it publicly, like truly publicly, like broadcasting on Twitter. Hey, we lost our head of sales. Like, I feel like I'm super fucked. Maybe you can be great to be able, it's really great to be able to have a support network that you can talk to about it. So I, I've done this recently, this other program called leaders in tech, which is a fellowship basically where they add founders and entrepreneurs from different companies and they form various learning groups that are facilitated learning groups where you are able to be very, very vulnerable about what is going on in your life and in your company. And I think that having some outlet for that to be truly vulnerable is really important for people.

AI assessment note: “You might not be able to do it publicly, like truly publicly”

Q I totally agree with you. And you said that about the ego element, and I actually got told by someone the other day, they said, Harry, you're so enraptured with what you do that you've almost become the company and you're not the company and you have to segregate yourself. How do you think about detachment from self and company and you are not your company, so to speak?

A Yeah. I think it's really hard for entrepreneurs. I remember in the early days of Justin TV, I would see my friends posting on Facebook. They'd be like, Oh, I'm having fun. I'd like, and the summers, especially going on vacations and I'd be sitting in our office programming. What am I doing with my life? The thing I told myself was at least I'm an entrepreneur and I have my own company. They might be getting paid more and on a career trajectory and actually having fun, but at least I have my own company and you know, I'm an entrepreneur. And so my entire identity was wrapped up in my company. And being an entrepreneur. And so the problem with that is that when things go badly, you feel badly about yourself. You transpose those feelings that you might have about what's happening in your company onto yourself. And that's a recipe for being depressed, feeling super bad every day, and ultimately burning out and quitting, which doesn't serve the interest of your company. And so I think that's the way to get out of that. Well, I don't think I have all the answers, but some of the things that have worked for me are Really focusing on your own mental health and wellbeing. I have a timer on my phone every day that actually reminds me to meditate on attachment specifically and to remind myself that, you know, if I achieve the thing that I want, I think I want, actually, I'm not going to …

AI assessment note: “reminds me to meditate on attachment specifically and to remind myself”

Q question to you is, sometimes it takes a mental and personal journey to get to that psychology. In terms of external aids, you know, some suggest therapists. I personally am a big believer in the power of therapy. You said before, actually, that it was a lifesaver. Can I ask, why do you think therapy works so well? And maybe for someone contemplating therapy, what would you advise them, Justin?

A Yeah, so I think I first started seeing a therapist seven years ago, something like that, when I was really stressed out about being a Founder, and I was feeling a lot of guilt, so I was like, finally broke down, I found someone, and it's very helpful to me, and I think what's really helpful is that you have someone who can, it's like a coach for dealing with what's going on and discovering more about yourself. I used to think that you could learn everything yourself, and now I'm a huge proponent of just surrounding yourself with the best coaches and mentors possible, because that's a way that you can just like expedite and speed up your learning and your self-improvement. With regards to therapy, I think it's very cathartic, To have someone to talk to, it's effectively a mechanism or construct that we've created in society to, like, make you feel like you have someone you can talk to, and you're not alone, and that can be very cathartic, I think, when working through any sort of problem that you have, and so now, today, you know, I have a therapist, I have a CEO coach, I actually have two CEO coaches, I have different conscious leadership groups that I'm part of, and so, from my perspective, you want to figure out who are those best Mentors and coaches and people to talk to who you can learn from and really surround yourself with them.

AI assessment note: “With regards to therapy, I think it's very cathartic, To have someone to talk to”

Q No, I'm going to download that one for sure. Listen, I spoke to your co-founder at Twitch, Kevin, before the show, and he said, investing, starting startups, advising founders, ranch life, family soon. How the hell does he balance it all?

A You know, I think what I'm pretty good at is really focusing on what's in my zone of genius. Like the thing that I'm really, the stuff I'm really good at and care about and love doing and gives me energy and then delegating the rest. So I really try to delegate everything that is not in my zone of genius. So for me, what does that mean? Like at Atrium, it's really focusing on our culture, focusing on the business strategy. It's all the sales like functions. So, you know, selling, whether it's fundraising, recruiting, maybe high profile clients. And that's Pretty much it. And then I try to build a team that can support me doing the rest of it. And the same is true on everything else. I'm actually not really investing very much at all because I'm busy at Atrium, but, um, actually my brother investing on, you know, on behalf of our kind of like a con family office, you know, kind of just out the delegating, I guess that's a form of delegation. And then advising founders, you know, it gives me energy to be able to like, I have some of my closest friendships are people who maybe we advise each other to be honest. Like I get feedback from them. They give them feedback. And we can talk about where they're at in their company. And so, you know, it doesn't feel like work to me. It just feels like a friendship. And I guess that's how I kind of balance some of these things.

AI assessment note: “focusing on what's in my zone of genius... and then delegating the rest.”

Q I do want to ask one thing is, when we chatted before, you said about the analogy of a board game, especially to the attachment thinking. Can I ask what's the analogy of the board game for everyone listening? I thought it was a fascinating one.

A Sure, so people are like, why, what's even the point then, Justin? Like, if there's no point in having these goals, or if you don't, like, really care about the goals, then what's the point of existing or having goals or doing anything? And the way I think about it is, I kind of think about like your goals in life or your company or as an entrepreneur or even your entire life as playing a board game. You know, you can imagine a rainy Saturday afternoon. I'm saying rainy because you're in London and I'm in San Francisco, so it's probably rainy. And then playing a game, you, your friends come over and you play this, break out this board game. And when you're playing the game, if you're like me, you're really engaged in it. You know, you're paying attention. It's engaging your mind. You're like, how do I make a strategy that's going to win? Talking about one of these, you know, fancy German board games, like settlers of Catan or something, not monopoly, but you're really trying to engage, be engaged in winning and you want to win and you try your hardest. But then when you put away the game, you know, the game's over and the next week, do you remember or even care what happened? Not really. You know, you accept it's in the past. It's actually not that big of a deal. And that's kind of how I think about how you should approach all of your goals and situations and circumstances in l…

AI assessment note: “I kind of think about like your goals in life... as playing a board game.”

Q And what do you like? What would you like to add or amend? Say you're Evan Spiegel for the day. What would you change about Snapchat?

A If I were Evan Spiegel for the day, what would I change about Snapchat? I actually think the thing that Snapchat's missing the most is a way of discovering new accounts. At the same time, I actually think that might be intentional. I haven't really talked with any of their product people about it, but I, I feel like it's almost better that there's no way of discovering accounts because then it doesn't dilute the attention from the followers you already have or that your actual friends, you know, people get like start following too many things on social media and then they like, it dilutes the power of all of them. Massive prisoners dilemma or tragedy of the commons, right? And so maybe it's good that there's no discovery. I don't really know. Their product teams are like pretty good and they've Really built a, what I think is the most compelling product I've seen in the last 10 years.

AI assessment note: “the thing that Snapchat's missing the most is a way of discovering new accounts.”

Q And what do you like? What would you like to add or amend? Say you're Evan Spiegel for the day. What would you change about Snapchat?

A If I were Evan Spiegel for the day, what would I change about Snapchat? I actually think the thing that Snapchat's missing the most is a way of discovering new accounts. At the same time, I actually think that might be intentional. I haven't really talked with any of their product people about it, but I, I feel like it's almost better that there's no way of discovering accounts because then it doesn't dilute the attention from the followers you already have or that your actual friends, you know, people get like start following too many things on social media and then they like, it dilutes the power of all of them. Massive prisoners dilemma or tragedy of the commons, right? And so maybe it's good that there's no discovery. I don't really know. Their product teams are like pretty good and they've Really built a, what I think is the most compelling product I've seen in the last 10 years.

AI assessment note: “the thing that Snapchat's missing the most is a way of discovering new accounts.”

Q What about the seven hundred million later stage growth fund that YC have raised? Is that a competition to the VC market? Because that's looking for a much later stage financing option. So, so what form of kind of synergy is there, or is it a competitive element?

A It depends on which, you know, life cycle you're talking about. The, the continuity fund originally was conceived of as a way to compete with, uh, more of the growth stage investors that were coming into the market in the later stage. So that's people who weren't actually classically VCs. I think as you've seen like tech companies, not IPO, uh, in the past, you know, six years has been this bull run in tech, but the companies have remained private for the vast majority of them. Uh, as a consequence, a lot of people were Traditional public market investors now, you know, in order to get returns have been coming into the private markets, and so I think that, ah, the continuity fund is much more competitive with those investors.

AI assessment note: “continuity fund is much more competitive with those investors.”

Q Well, that is very kind of you, but I do want to start saying, maybe for those that missed our first episode, how did you make your way into the world of startups, and what was that founding moment for you with Atrium today?

A Yeah, well, it's been a long road. I think I started my first startup in Kind of like the Gmail equivalent. Some are very similar to Google Calendar. It's called Kiko. The only really notable things about that startup were it was very early on in this online web application world. And we got into Y Combinator because of that, which kind of set me off on my start career, kind of run through it really quickly, but eventually that company failed and we desperately sold it on eBay. And then we ended up starting a new company called Justin TV, which was an attempt to To make our own live reality show on the internet. And that was also a terrible idea that mostly failed, but fortunately we launched this show, turned it into a, uh, eventually a platform for anyone to broadcast their own live video. And then from there, we eventually pivoted that after a couple of years into Twitch. And so in 2014, you know, sold Twitch to Amazon. I had actually started some other companies, including this company called exec, uh, at the time that was kind of like an air running service. Sold that to Handy in 2014, so I was kind of burned out of startups after about 10 years and decided to go join Y Combinator and be a partner at YC. And after a couple years of investing in YC startups, I decided being an investor full-time wasn't really for me. At that point in my life, I felt like I wasn't learning a…

AI assessment note: “And we got into Y Combinator because of that, which kind of set me off”

Q And I want to move on to a second segment of the show, just discussing your own brand now, uh, as a, as a VC with YC, uh, and, and how you've approached the personal brand. So how important do you think a personal brand is for investors in today's environment?

A Well, I think investors have to have, you know, there's three qualities of investors that I, or of investors or firms that I think are important investing. I've thought about this a little bit. The first one is a platform that generates leads for them or reasons why people want their money. Right. So an example could be me of like trying to put out a lot of advice on Snapchat and Or it could be Sequoia having a really great, or Y Combinator having a really great reputation and name. Or it could be, uh, something like Jason Lemkin, uh, who just raised his seventy million dollar fund with SaaS there, and he has a community, um, that's all about a specific vertical, right? SaaS software. Number one is a reason why people want your money. The second thing is picking good companies with, like, based on a strong thesis. And the third, I think, is being relentless in pursuing companies that Once you've decided to like, make sure that they take your money and not someone else's.

AI assessment note: “The first one is a platform that generates leads for them or reasons why”

Q No, I'm going to download that one for sure. Listen, I spoke to your co-founder at Twitch, Kevin, before the show, and he said, investing, starting startups, advising founders, ranch life, family soon. How the hell does he balance it all?

A You know, I think what I'm pretty good at is really focusing on what's in my zone of genius. Like the thing that I'm really, the stuff I'm really good at and care about and love doing and gives me energy and then delegating the rest. So I really try to delegate everything that is not in my zone of genius. So for me, what does that mean? Like at Atrium, it's really focusing on our culture, focusing on the business strategy. It's all the sales like functions. So, you know, selling, whether it's fundraising, recruiting, maybe high profile clients. And that's Pretty much it. And then I try to build a team that can support me doing the rest of it. And the same is true on everything else. I'm actually not really investing very much at all because I'm busy at Atrium, but, um, actually my brother investing on, you know, on behalf of our kind of like a con family office, you know, kind of just out the delegating, I guess that's a form of delegation. And then advising founders, you know, it gives me energy to be able to like, I have some of my closest friendships are people who maybe we advise each other to be honest. Like I get feedback from them. They give them feedback. And we can talk about where they're at in their company. And so, you know, it doesn't feel like work to me. It just feels like a friendship. And I guess that's how I kind of balance some of these things.

AI assessment note: “I really try to delegate everything that is not in my zone of genius.”

Q So I am interested in discussing kind of something we don't often discuss being mental health. Before we dive into maybe specific strategies around that, I'd love to set the background. Why did you maybe engage in this Series of habits really based around self-improvement. And you mentioned the burnt out on startups. What does that really look like? Because burnout is often used, but what does that really mean?

A Yeah, I think people are starting to talk about it, which is really great. When I was in my first section of my entrepreneurial career, you know, building Justin TV and Twitch, I remember that every summer I would want to quit and go get a job or do something else. And I was always distracted by other things. New ideas. You know, those were all kind of escape fantasies in a way. Realization that, wow, I'm in a lot of pain right now, or I'm like stressed out right now, which is a form of pain, and I need to get out of this situation. And so you're like thinking about new things or different things or whatever. Very good in that 10 year period. I think I, uh, mostly just white knuckled it through it. And then eventually when I did get out with exits, I was like, oh my God, I'm never going to do that again. And the time at YC was nice because YC is very stable as an organization. It's a brand. People want to go there. You know, you kind of like can't fuck it up really. And so the kind of mental burden was like way off by comparison to startups. And then, you know, when I got back into Okay, I have 10 years of experience now. I know what I'm doing. And after the first, for the first three months, I was like, wow, I really figured it out. I know what I'm doing. This time, I'm like, great. And then, of course, you know, anyone who's started a startup knows that reality kicked in. And…

AI assessment note: “those were all kind of escape fantasies in a way”

Q Well, that is very kind of you, but I do want to start saying, maybe for those that missed our first episode, how did you make your way into the world of startups, and what was that founding moment for you with Atrium today?

A Yeah, well, it's been a long road. I think I started my first startup in Kind of like the Gmail equivalent. Some are very similar to Google Calendar. It's called Kiko. The only really notable things about that startup were it was very early on in this online web application world. And we got into Y Combinator because of that, which kind of set me off on my start career, kind of run through it really quickly, but eventually that company failed and we desperately sold it on eBay. And then we ended up starting a new company called Justin TV, which was an attempt to To make our own live reality show on the internet. And that was also a terrible idea that mostly failed, but fortunately we launched this show, turned it into a, uh, eventually a platform for anyone to broadcast their own live video. And then from there, we eventually pivoted that after a couple of years into Twitch. And so in 2014, you know, sold Twitch to Amazon. I had actually started some other companies, including this company called exec, uh, at the time that was kind of like an air running service. Sold that to Handy in 2014, so I was kind of burned out of startups after about 10 years and decided to go join Y Combinator and be a partner at YC. And after a couple years of investing in YC startups, I decided being an investor full-time wasn't really for me. At that point in my life, I felt like I wasn't learning a…

AI assessment note: “we got into Y Combinator because of that, which kind of set me off”

Q things I was super intrigued to ask you, because another of the books that you've been super excited by is the 15 commitments of conscious leadership and looking to roll that out at Atrium and other companies you're associated with. I guess my question to you following that is, what's required to roll it out? What are the core principles that you really want to instill within the organizations, Justin?

A Yeah, so the 15 commitments of conscious leadership is this book that I read. So I can't remember who recommended it to me, but it was, oh, I actually, it was Steve Huffman from Reddit. He recommended me this book, and I read it, and it just really resonated with the personal journey that I've been on in the last year to be more self-aware and improve myself, take really more ownership for myself. This is kind of like the company version of that. It's like, how do you bring those types of cultural values into your company? And so there's 15 commitments, which is a lot, and I think their first ones are the most important, and then it kind of gets into the kind of the wild, hippie ones at the end of the book But the first three really resonated with me very deeply. I'll just go into those ones. So the first one is radical responsibility. And I think that one was very easy for me as an entrepreneur to internalize because I've always been, you know, had this radical responsibility in a way because you're an entrepreneur, you're, there's no one else coming to save you if something's not working or something bad about your company, right? You have no one else to blame. And so that really was true to me, you know, kind of resonated with me immediately. Number two and number three were more interesting because I think I learned a lot from reading them. The second one was radical curios…

AI assessment note: “The first one is radical responsibility.”

Q No, I do agree with you there. I do want to finish there on Atrium itself. Such an exciting time ahead. But tell me, what are the next five years look like for you and for Atrium? What's that exciting roadmap?

A Yeah. So, uh, I mean, it's pretty simple. You know, we just want to continue to build the team of incredibly talented individuals. And I think we've done a good job so far. We're about a 150 people in San Francisco hiring a lot of roles right now, but continue to build the team, continue to serve the clients in better and better ways. I think there's a lot of details I could go into, but that's a lot of innovation on the operations side. It's a lot of innovation on the technology side, both in tools that the clients use themselves, but also our internal team uses. And then I continue to build a brand as the, um, as one of these companies in Silicon Valley, that's very invested in founders being successful. You know, I think I learned a lot from YC there, and I think we're kind of making progress on all those things. We just need to execute and I'm feeling pretty good about our prospects there. You know, for the first time we have an exec team that I really trust and have empathy for and care about. We really work well together. They're kind of really vibing. And it's a great feeling because I think that all of the execution on all those things I kind of mentioned will flow from that. And at the same, I guess the last thing I'll say is I really am invested in the culture and how do you build a conscious company where people take radical responsibility and they have a growth mind…

AI assessment note: “continue to build the team of incredibly talented individuals... serve the clients in better”

Q it your air tables, be it your zooms of the world. And PG wrote a phenomenal piece about why this is such a great business and business model to operate. I'm really interested. How do you think about actually when the majority of your customer base and customers are Similar to you, high growth tech companies. And do you think that really is a viable model over the long term?

A That's a good question because, you know, there is a question of, is this, where are we in the business cycle? And if all, you know, if there's a downturn, do all these companies go away or they start cut costs? I think that when I was thinking about selling or building a company that sold Startup community for a long time, you know, had the YC connections and other investor relationships in Silicon Valley. Atrium itself has raised money from over a hundred VCs and angel investors in Silicon Valley. So I felt like that would be a really good initial bootstrap to get access to a lot of different potential customers, which it was. So it kind of made sense for where I was in my career. And obviously it was a really quick way to get out the gate. I do think that with legal specifically, it's one of those things that it's really, you know, you use it in good times and use it in bad times. That's part of what attracted me actually to this industry is that I was a customer, a client of legal over my 15 year entrepreneurial investor career. And, um, I'd use kind of legal services no matter what was happening, whether they were, you know, it was good or bad, or like, you know, no matter what you want to do in America and in business, you end up, it's a big transaction. You end up paying attorneys, whether it's, you know, selling your company or raising money or signing a major commercia…

AI assessment note: “pretty Confident that this will exist in a downturn.”

Q So I am interested in discussing kind of something we don't often discuss being mental health. Before we dive into maybe specific strategies around that, I'd love to set the background. Why did you maybe engage in this Series of habits really based around self-improvement. And you mentioned the burnt out on startups. What does that really look like? Because burnout is often used, but what does that really mean?

A Yeah, I think people are starting to talk about it, which is really great. When I was in my first section of my entrepreneurial career, you know, building Justin TV and Twitch, I remember that every summer I would want to quit and go get a job or do something else. And I was always distracted by other things. New ideas. You know, those were all kind of escape fantasies in a way. Realization that, wow, I'm in a lot of pain right now, or I'm like stressed out right now, which is a form of pain, and I need to get out of this situation. And so you're like thinking about new things or different things or whatever. Very good in that 10 year period. I think I, uh, mostly just white knuckled it through it. And then eventually when I did get out with exits, I was like, oh my God, I'm never going to do that again. And the time at YC was nice because YC is very stable as an organization. It's a brand. People want to go there. You know, you kind of like can't fuck it up really. And so the kind of mental burden was like way off by comparison to startups. And then, you know, when I got back into Okay, I have 10 years of experience now. I know what I'm doing. And after the first, for the first three months, I was like, wow, I really figured it out. I know what I'm doing. This time, I'm like, great. And then, of course, you know, anyone who's started a startup knows that reality kicked in. And…

AI assessment note: “every summer I would want to quit and go get a job”

Q So when you look back to that time in 2012, 2013 starting, and you see your transition just as a kind of individual, Within the industry, having worked as a partner at YC for that time, uh, how have you seen your investment decision-making change and your kind of approach to pattern recognition change?

A Well, I would say that I have learned a lot. I think that the fundamental thing is that you want to invest in founders who are talented people. I think everyone kind of says that, and I really think that's true. Like for me, like all the, you know, I guess if you look at my angel investing portfolio, the angel investments I've made The good ones are like Zenefits, Cruise, which was started by one of my co-founders from Justin TV, Kyle, and my brother, Daniel, and, uh, was just acquired by GM for over a billion dollars. Tilt. I think those are the best companies. Oh, and Ginkgo Bioworks and Bella Beat. A lot of them are like, uh, more recent. So, you know, they had less time to grow. So if they weren't named, there's a lot, you know, doesn't mean it's not a good company. It just means that it's probably early, later in the portfolio. Um, and I guess the commonality among all of these is really the founders were really good. Oftentimes I invested in things where the founders actually weren't that good. And it became apparent, you know, like pretty quickly within the first year, it's very hard to know day one, I think of, of investing, but retroactively it's much, much easier to tell. And then, you know, so now I try to look more actively on like, are these people actually going to take this all the way instead of just like, is this a big idea in a big space? I think before I was …

AI assessment note: “before I was much more Driven by the size of the market... now... by the founders.”

Q So when you look back to that time in 2012, 2013 starting, and you see your transition just as a kind of individual, Within the industry, having worked as a partner at YC for that time, uh, how have you seen your investment decision-making change and your kind of approach to pattern recognition change?

A Well, I would say that I have learned a lot. I think that the fundamental thing is that you want to invest in founders who are talented people. I think everyone kind of says that, and I really think that's true. Like for me, like all the, you know, I guess if you look at my angel investing portfolio, the angel investments I've made The good ones are like Zenefits, Cruise, which was started by one of my co-founders from Justin TV, Kyle, and my brother, Daniel, and, uh, was just acquired by GM for over a billion dollars. Tilt. I think those are the best companies. Oh, and Ginkgo Bioworks and Bella Beat. A lot of them are like, uh, more recent. So, you know, they had less time to grow. So if they weren't named, there's a lot, you know, doesn't mean it's not a good company. It just means that it's probably early, later in the portfolio. Um, and I guess the commonality among all of these is really the founders were really good. Oftentimes I invested in things where the founders actually weren't that good. And it became apparent, you know, like pretty quickly within the first year, it's very hard to know day one, I think of, of investing, but retroactively it's much, much easier to tell. And then, you know, so now I try to look more actively on like, are these people actually going to take this all the way instead of just like, is this a big idea in a big space? I think before I was …

AI assessment note: “before I was much more driven by the size of the market... now... by the founders.”

Q And I want to move on to a second segment of the show, just discussing your own brand now, uh, as a, as a VC with YC, uh, and, and how you've approached the personal brand. So how important do you think a personal brand is for investors in today's environment?

A Well, I think investors have to have, you know, there's three qualities of investors that I, or of investors or firms that I think are important investing. I've thought about this a little bit. The first one is a platform that generates leads for them or reasons why people want their money. Right. So an example could be me of like trying to put out a lot of advice on Snapchat and Or it could be Sequoia having a really great, or Y Combinator having a really great reputation and name. Or it could be, uh, something like Jason Lemkin, uh, who just raised his seventy million dollar fund with SaaS there, and he has a community, um, that's all about a specific vertical, right? SaaS software. Number one is a reason why people want your money. The second thing is picking good companies with, like, based on a strong thesis. And the third, I think, is being relentless in pursuing companies that Once you've decided to like, make sure that they take your money and not someone else's.

AI assessment note: “The first one is a platform that generates leads for them or reasons why”