The Exchanges

Q Can I ask your advice here, Joe? The ego checking elements, one that I often contemplate as a very, very young individual in the ecosystem, and, you know, hugely lucky to have support, and in, in some cases, the confidence of great people behind me. How do you ego check efficiently and accurately, and what really brings you back down to earth, so to speak?

A It's really about finding people who will tell you when you're wrong, you know, and being a One thing I've done in the past that has been really successful is actually offering a reward to like prove me wrong. So for example, there's been big initiatives that we talk about taking and they're, they're going to, you know, we're going to put a whole team on it and it's going to take a quarter and that's like a really big investment. So offering like almost a bounty of, you know, let's say, 10,000 dollars to somebody who could concretely say why this is a bad idea and why we'd be better off Putting our resources somewhere else is like a small price to pay to avoid taking that wrong turn. So that's like a big example, but the small examples are just, I'm lucky I have somebody like Hunter who I talk to weekly, if not every couple of days, and he has probably 80% of the time a different opinion than me, and I can hear that opinion and make a decision if I want to, what impact that's going to have on me, but I'm always open to feedback from the folks around me.

AI assessment note: “It's really about finding people who will tell you when you're wrong”

Q Well, I'm sure it's paid off now, but we're kind of talking about kind of your communication with the board and the investor base there. I'd love to hear, we chatted before about investor update emails. I'd love to hear, how do you approach investor update emails, Joe?

A So at Cloud, I never sent an investor update email, and I always found something more important to do, and it was something that was just, like, not on my priority list in any way. Cloud was mostly in San Francisco, so I also always saw my investors. They would always stop by. We Get coffee. You know, they were kind of in the loop kind of in general. Joy mode is in LA, so being in LA, I don't see my investors much, and in fact, they can't even use our product because our product is only in LA. I use investor update emails to replace the fact that I don't see them, but I found that was kind of the initial intention, but it's turned into so much more than that, and I write really in-depth investor emails, like spend 6:08 hours on one, They're all archived on a Google doc that is like almost 200 pages long. Now I take it from the standpoint of it's not at all about spin. It's not at all about like making them feel comfortable that they put all this money in the company. I want them to be terrified that they put money in this company. Like we are all in the same boat. So I feel really empowered to tell them what I'm afraid of and what I need help with and focus on those things. And it is somewhat therapeutic and just getting it out there. But it also then mobilizes and focuses the investor base on the stuff I'm trying to work through, and that is my focus. And it's been super helpf…

AI assessment note: “I take it from the standpoint of it's not at all about spin.”

Q with an obsession of mine, which is a theme of transferable learnings from kind of entrepreneurial endeavors. You're a serial entrepreneur, as we said, co-founded and founded Clout prior to Joy Mode, a company that ultimately didn't survive, but I want to start on the immensely hard question, but one from one of your investors in Craig Shapiro, which is, What's the single greatest learning from the experience with clout?

A Clout was a really intense experience. I went into that having, you know, been an entrepreneur, but never at any real scale. Like, the biggest company was only, like, four people, and at clout, we raised nearly fifty million dollars. We had Kleiner Perkins as our main investor. We had IVP. We had Microsoft as investors. We grew to, like, a hundred people. You know, it was, like, a pretty big deal. Machine at the pinnacle, and through that process, basically did everything wrong at some point, and the biggest learning I had was mistakes generally don't kill you if you are proactive about correcting them, and I like to think that we were intellectually honest and faced reality and made changes as we need to. There was one mistake that was really basically impossible to fix, and it was raising too much money at too high of a valuation, and I'd heard that a million times before, but it was always something that wouldn't happen to me. That was something that happened to other companies and eventually it caught up to us and it was really challenging to break through to the next plateau that you have to get to at like a, you know, a super high valuation. We were fortunate to be able to see it through to a successful outcome and an acquisition, but ultimately I think we cut short what the real opportunity could have been by putting so much pressure on ourselves.

AI assessment note: “the biggest learning I had was mistakes generally don't kill you”

Q Can I ask your advice here, Joe? The ego checking elements, one that I often contemplate as a very, very young individual in the ecosystem, and, you know, hugely lucky to have support, and in, in some cases, the confidence of great people behind me. How do you ego check efficiently and accurately, and what really brings you back down to earth, so to speak?

A It's really about finding people who will tell you when you're wrong, you know, and being a One thing I've done in the past that has been really successful is actually offering a reward to like prove me wrong. So for example, there's been big initiatives that we talk about taking and they're, they're going to, you know, we're going to put a whole team on it and it's going to take a quarter and that's like a really big investment. So offering like almost a bounty of, you know, let's say, 10,000 dollars to somebody who could concretely say why this is a bad idea and why we'd be better off Putting our resources somewhere else is like a small price to pay to avoid taking that wrong turn. So that's like a big example, but the small examples are just, I'm lucky I have somebody like Hunter who I talk to weekly, if not every couple of days, and he has probably 80% of the time a different opinion than me, and I can hear that opinion and make a decision if I want to, what impact that's going to have on me, but I'm always open to feedback from the folks around me.

AI assessment note: “It's really about finding people who will tell you when you're wrong”

Q Absolutely. I mean, a question from Satya Patel at Homebrew, he asked, given that experience, how did you fundraise differently with Joy Mode?

A With Joy Mode, I've been really Focused on getting the right people in and doing that at the expense of valuation. I'd rather have homebrew and the pleasure of working with folks like Satya and Hunter and, you know, the collaborative fund and 10 one 10 and all these great investors we have. I wanted to make it easy for them to say yes and not spend time going in circles trying to raise and squeak out a couple extra percentage points here or there just to get back to work with the people I wanted on my team. And that, so far, has served us really well. I'm fortunate to have the folks around the table that we do have.

AI assessment note: “Focused on getting the right people in and doing that at the expense of valuation.”

Q Absolutely. I mean, a question from Satya Patel at Homebrew, he asked, given that experience, how did you fundraise differently with Joy Mode?

A With Joy Mode, I've been really Focused on getting the right people in and doing that at the expense of valuation. I'd rather have homebrew and the pleasure of working with folks like Satya and Hunter and, you know, the collaborative fund and 10 one 10 and all these great investors we have. I wanted to make it easy for them to say yes and not spend time going in circles trying to raise and squeak out a couple extra percentage points here or there just to get back to work with the people I wanted on my team. And that, so far, has served us really well. I'm fortunate to have the folks around the table that we do have.

AI assessment note: “getting the right people in and doing that at the expense of valuation”

Q Not at all, but I want to kick off today by discussing a little about you. So how did you make your way into the world of startups and come to realize that the world of ownership is now over with the starting of Joy Mode?

A Yeah, Joy Mode is a really exciting new venture. Funny thing is, I actually was working on this Before clout, I had moved to New York city and was in a really small apartment. I met my, my girlfriend there. We moved in together, eventually later got married, but the place was so small that just a function in it. Anytime either one of us bought something, we had to get rid of something. So I got really obsessed with the notion of ownership, but I couldn't figure out what to do with it and how to make this a company and had the idea for clout and started that and kind of had that adventure and came back to join mode. But I've always been an entrepreneur going all the way back to Kind of middle school days, and buying and selling used video games, and a kind of bunch of graveyard of bad ideas in between.

AI assessment note: “I got really obsessed with the notion of ownership”

Q In terms of that kind of benchmark setting, I'm intrigued. What's the internal decision making around the actual kind of creation of OKRs, so to speak?

A We are really focused on setting one or two high-level company goals, and then making sure every team has a goal that flows into those company goals, and every person flows into their team goals, so that it's easy for everybody in the company to know what they're working on and how it impacts the overall growth of the company. And we spend a huge amount of time, three weeks, a month, working through those OKRs, making sure we're setting them in a way that is both achievable and a stretch, and because there's nothing worse than setting an OKR that day one everyone knows you're, like, have no chance to hit, or setting one that you hit, you know, halfway through a quarter. So it really is an investment in planning and resource allocation and the math equations behind your business and making sure you've got top of funnel and Paid acquisition lined up and all the different pieces that, that actually give you a chance to hit whatever goal you're trying to set.

AI assessment note: “We are really focused on setting one or two high-level company goals”

Q We've chatted before about the benefits of naivety for first-time founders and what that can do. I'm intrigued in terms of that. How do you think about the balance between maybe product vision and that belief in the mission versus the realism of maybe when something isn't working? How do you balance the two?

A It's a real challenge, and as this quote-unquote serial entrepreneur, like, I find myself always trying to check if I'm overcorrecting for something that happened in the past that isn't really happening now, or Kind of letting that scar tissue dictate how I act, but specifically around knowing when to keep pushing versus, like, when to face reality. I think it's more about knowing what hill you're willing to die on, for kind of lack of a better analogy. Like, there are things in our business, for example, we have this notion of a membership, which is kind of controversial in our structure, that I'm willing to basically kill the company to prove It is right, and I believe so strongly that that is kind of a core function of the value prop that we will keep iterating on it until we die. There are other things that clearly aren't that high. Don't rise to that level of just something we're going to protect and, you know, being really willing to face reality when those things are wrong and change them.

AI assessment note: “I think it's more about knowing what hill you're willing to die on”

Q We've chatted before about the benefits of naivety for first-time founders and what that can do. I'm intrigued in terms of that. How do you think about the balance between maybe product vision and that belief in the mission versus the realism of maybe when something isn't working? How do you balance the two?

A It's a real challenge, and as this quote-unquote serial entrepreneur, like, I find myself always trying to check if I'm overcorrecting for something that happened in the past that isn't really happening now, or Kind of letting that scar tissue dictate how I act, but specifically around knowing when to keep pushing versus, like, when to face reality. I think it's more about knowing what hill you're willing to die on, for kind of lack of a better analogy. Like, there are things in our business, for example, we have this notion of a membership, which is kind of controversial in our structure, that I'm willing to basically kill the company to prove It is right, and I believe so strongly that that is kind of a core function of the value prop that we will keep iterating on it until we die. There are other things that clearly aren't that high. Don't rise to that level of just something we're going to protect and, you know, being really willing to face reality when those things are wrong and change them.

AI assessment note: “I think it's more about knowing what hill you're willing to die on”

Q In terms of that kind of benchmark setting, I'm intrigued. What's the internal decision making around the actual kind of creation of OKRs, so to speak?

A We are really focused on setting one or two high-level company goals, and then making sure every team has a goal that flows into those company goals, and every person flows into their team goals, so that it's easy for everybody in the company to know what they're working on and how it impacts the overall growth of the company. And we spend a huge amount of time, three weeks, a month, working through those OKRs, making sure we're setting them in a way that is both achievable and a stretch, and because there's nothing worse than setting an OKR that day one everyone knows you're, like, have no chance to hit, or setting one that you hit, you know, halfway through a quarter. So it really is an investment in planning and resource allocation and the math equations behind your business and making sure you've got top of funnel and Paid acquisition lined up and all the different pieces that, that actually give you a chance to hit whatever goal you're trying to set.

AI assessment note: “setting one or two high-level company goals, and then making sure every team has a goal”

Q Not at all, but I want to kick off today by discussing a little about you. So how did you make your way into the world of startups and come to realize that the world of ownership is now over with the starting of Joy Mode?

A Yeah, Joy Mode is a really exciting new venture. Funny thing is, I actually was working on this Before clout, I had moved to New York city and was in a really small apartment. I met my, my girlfriend there. We moved in together, eventually later got married, but the place was so small that just a function in it. Anytime either one of us bought something, we had to get rid of something. So I got really obsessed with the notion of ownership, but I couldn't figure out what to do with it and how to make this a company and had the idea for clout and started that and kind of had that adventure and came back to join mode. But I've always been an entrepreneur going all the way back to Kind of middle school days, and buying and selling used video games, and a kind of bunch of graveyard of bad ideas in between.

AI assessment note: “I got really obsessed with the notion of ownership, but I couldn't figure out”

Q No, absolutely. You spoke about the benefits of second time around there, which seems paradoxical considering my next statement that you told me before, and it's serial entrepreneurship is maybe overrated. With such a bold statement, how can I not start with it as a serial entrepreneur yourself? What makes you say this, Joe?

A I mean, I definitely benefit every day from the worshipping of serial entrepreneurship in this industry. You know, the benefit of the doubt you get as a serial entrepreneur is awesome, both from investors who kind of will believe more of what you say, and from potential candidates that want to get on the bus with somebody who has a proven outcome in the past. The challenge, though, and why I say serial entrepreneurs can be overrated is I'm not a different person than I was on day 99 of clout. Like, we signed a deal, we got acquired, it was a reasonable outcome, but I'm not a different person, but the way people perceive me and the interaction with people act like I am, like I've totally done something that's never been done, and it's just kind of strange to me, and I find that it creates a danger in myself to Of believing my own hype, and I have to be really careful not to think I know it all. And I try to find ways to break that. And then it also, when I don't know it all, which is all the time, it makes me really stressed of like, why I should know this. Like I'm a serial entrepreneur. I've been through this. Why don't I know this thing? Why is this hard? And startups are just hard. And I don't think it matters how many times you've been through it. It's gonna going to be hard. And some of the, the serial entrepreneurship stuff, I think, is inflated, though I appreciate the b…

AI assessment note: “The challenge, though, and why I say serial entrepreneurs can be overrated is”

Q said about kind of dying on the hill and which hill that you're willing to die on, so to speak, because we chatted before on one of your leading principles is to make big bets to win. I'd love to unpack this. What do you mean by making big bets to win? And it's kind of startups and founding startups, not all making big bets to win, so to speak.

A You know, one of the challenges as a founder is it's so hard when you're starting, especially if you, you know, haven't been through it before, and you've never raised money, you don't have those connections, just crawling into the game, so to say, like meeting the investors, getting that first round done, you know, you've probably been living on no salary for a while, you're begging, borrowing, stealing, everything you can do to just squeak by, and you just want a chance, and you finally get that first investment, and you're got your little bit of a paycheck, and like, It feels like a real company, and you're starting to feel, like, legit. It is really scary to then think about, like, throwing that away. So you start getting into this, like, play not to lose, and I think that is where a lot of companies stall out. A lot of companies, CEOs, founders, founding teams, it is so hard to make it up that first hill that they can't accept the fact that what got them there won't get them to the next stage, and there's fear in making bets that feel like they could risk the company.

AI assessment note: “So you start getting into this, like, play not to lose”

Q with an obsession of mine, which is a theme of transferable learnings from kind of entrepreneurial endeavors. You're a serial entrepreneur, as we said, co-founded and founded Clout prior to Joy Mode, a company that ultimately didn't survive, but I want to start on the immensely hard question, but one from one of your investors in Craig Shapiro, which is, What's the single greatest learning from the experience with clout?

A Clout was a really intense experience. I went into that having, you know, been an entrepreneur, but never at any real scale. Like, the biggest company was only, like, four people, and at clout, we raised nearly fifty million dollars. We had Kleiner Perkins as our main investor. We had IVP. We had Microsoft as investors. We grew to, like, a hundred people. You know, it was, like, a pretty big deal. Machine at the pinnacle, and through that process, basically did everything wrong at some point, and the biggest learning I had was mistakes generally don't kill you if you are proactive about correcting them, and I like to think that we were intellectually honest and faced reality and made changes as we need to. There was one mistake that was really basically impossible to fix, and it was raising too much money at too high of a valuation, and I'd heard that a million times before, but it was always something that wouldn't happen to me. That was something that happened to other companies and eventually it caught up to us and it was really challenging to break through to the next plateau that you have to get to at like a, you know, a super high valuation. We were fortunate to be able to see it through to a successful outcome and an acquisition, but ultimately I think we cut short what the real opportunity could have been by putting so much pressure on ourselves.

AI assessment note: “the biggest learning I had was mistakes generally don't kill you”

Q What would you most like to change about Silicon Valley and VC?

A I remember one of the first rounds of funding we raised for Clout, going to an investor meeting, and it was, we were doing a partner pitch, you got all the way, you know, that's the last step before you get the check, and the investor who was sponsoring us, right before we walked in the door, I said, like, hey, what do you think the biggest pushback is going to be from your team? And he said to me, you're not from the Academy. And I didn't know what that meant. And I was like, what do you mean? He's like, oh, well, you know, you didn't go to Stanford. You didn't work at Google. You're just not from the Academy. And we've never invested in someone like you. And he didn't mean it in a bad way at all. They ended up investing and being great and super supportive. But like that comment really shook how lucky I was to like make it to that room, but how unfair it was that like, So many people don't, and I think diversity and, you know, this is the theme of the moment of finally and appropriately is diversity and the venture space and giving people chances who didn't go to the academy is something I'm really passionate about.

AI assessment note: “giving people chances who didn't go to the academy is something I'm really passionate”

Q And you mentioned Hunter there from Homebrew. He asks, what do you look for in hires at Joy Mode, and how's that maybe different from the team building and hiring strategy with Cloud?

A The early days of Cloud was a really ragtag crew. When I started the company, I'd literally never met anyone who worked at Google. I knew nobody in the startup world at all. So, The bar to get hired at Clout was like willingness to quit your current job. If you were basically willing to quit your current job, you were on the team. So, you know, we got some really lucky diamonds in the rough that we found that went on hugely successful at Clout and hugely successful after. But when I look back at Clout, the team is what I'm most proud of, but there's really four or five generations of team that as we were able to kind of raise our profile and You know, attract a different level of candidate. We were able to continue to up-level the team. The pleasure of building Joy Mode and kind of having that second time around network and notoriety around that is, from the start, we've been able to really pull the best possible people and kind of have a top one percent team.

AI assessment note: “we've been able to really pull the best possible people and kind of have a top one percent team.”

Q What would you most like to change about Silicon Valley and VC?

A I remember one of the first rounds of funding we raised for Clout, going to an investor meeting, and it was, we were doing a partner pitch, you got all the way, you know, that's the last step before you get the check, and the investor who was sponsoring us, right before we walked in the door, I said, like, hey, what do you think the biggest pushback is going to be from your team? And he said to me, you're not from the Academy. And I didn't know what that meant. And I was like, what do you mean? He's like, oh, well, you know, you didn't go to Stanford. You didn't work at Google. You're just not from the Academy. And we've never invested in someone like you. And he didn't mean it in a bad way at all. They ended up investing and being great and super supportive. But like that comment really shook how lucky I was to like make it to that room, but how unfair it was that like, So many people don't, and I think diversity and, you know, this is the theme of the moment of finally and appropriately is diversity and the venture space and giving people chances who didn't go to the academy is something I'm really passionate about.

AI assessment note: “giving people chances who didn't go to the academy is something I'm really passionate about”

Q Yeah, absolutely. I love that analogy to boxing, but tell me the next five years for you and for joy mode, what's the exciting roadmap ahead?

A You know, it wasn't that long ago when I would walk into somebody's house or apartment and stumble on their CD collection or their DVD collection. And it was this really interesting view in Into their world and their interests. Now, when that happens, it's weird, and I'm, you know, I ask them, like, do you not know about Netflix? Do you not know about Spotify? Like, why do you have this stuff? And our goal with Joy Mode is to make access better than ownership, and I want it to be weird when you go into somebody's house, and you see things that are used less than weekly. Things that are super common now, like, I don't believe you need to own, and I want to Help create a world where what you do is more about what you can imagine than what you own. So that's what I'm excited about, and making that world a reality.

AI assessment note: “our goal with Joy Mode is to make access better than ownership”

Q And you mentioned Hunter there from Homebrew. He asks, what do you look for in hires at Joy Mode, and how's that maybe different from the team building and hiring strategy with Cloud?

A The early days of Cloud was a really ragtag crew. When I started the company, I'd literally never met anyone who worked at Google. I knew nobody in the startup world at all. So, The bar to get hired at Clout was like willingness to quit your current job. If you were basically willing to quit your current job, you were on the team. So, you know, we got some really lucky diamonds in the rough that we found that went on hugely successful at Clout and hugely successful after. But when I look back at Clout, the team is what I'm most proud of, but there's really four or five generations of team that as we were able to kind of raise our profile and You know, attract a different level of candidate. We were able to continue to up-level the team. The pleasure of building Joy Mode and kind of having that second time around network and notoriety around that is, from the start, we've been able to really pull the best possible people and kind of have a top one percent team.

AI assessment note: “from the start, we've been able to really pull the best possible people”

Q pick your battles. I think you mentioned that one area of kind of keeping at it I spoke to David Weissman at 10 One 10, one of your investors, and he said the special thing about you is your process for testing and learning. So I'd love to hear, how do you look to kind of implement, and what's the framework for that testing and learning in a lean way?

A In a consumer startup, the So the pace that you can learn is ultimately a huge, huge factor in your long-term success. So we've spent a lot of time as a team being very methodical about what questions we needed to answer that gave us confidence to move forward. And clarity around these waypoints let us then devise tests, and with a specific goal of making those tests as easily actionable as possible, to Build our confidence that we were on the right path. So again, just being really methodical about understanding those questions and what proving them gave you confidence around and then moving really aggressively to do that. We tool everything. We measure everything that is startup table stakes at this point, but asking those questions and really from the start, having a sense of what you need to learn to feel confident that you're investing your time in the right place has been critical for us.

AI assessment note: “being very methodical about what questions we needed to answer that gave us confidence”

Q Yeah, no, absolutely. I mean, I completely understand the courage and risk-taking ability it must take to do that. I mean, what are the core challenges, though, to implementing this? In some cases, kind of the burn the boat strategy.

A I think you should always have an initiative that you are working on that a huge portion of the team and investor base is afraid will kill the company. Like, that is a good barometer of, like, are you being daring enough? And most people are Are going to tell you just the same way when you start your company, most people tell you it's a bad idea when you're like in the process of building your company, people are going to tell you that stick to these paths that are kind of clear and have been paved before you and where you have traction and it's easy to fall into that. I think being willing as a founder CEO to look at that data and think about your big vision and where you're going to get need to get to and continuously being willing to risk it all to make that next jump. Is absolutely critical factor in, you know, these companies that kind of go on and become staples of our daily life was their stories of them doing what it wants to do.

AI assessment note: “a huge portion of the team and investor base is afraid will kill the company”

Q pick your battles. I think you mentioned that one area of kind of keeping at it I spoke to David Weissman at 10 One 10, one of your investors, and he said the special thing about you is your process for testing and learning. So I'd love to hear, how do you look to kind of implement, and what's the framework for that testing and learning in a lean way?

A In a consumer startup, the So the pace that you can learn is ultimately a huge, huge factor in your long-term success. So we've spent a lot of time as a team being very methodical about what questions we needed to answer that gave us confidence to move forward. And clarity around these waypoints let us then devise tests, and with a specific goal of making those tests as easily actionable as possible, to Build our confidence that we were on the right path. So again, just being really methodical about understanding those questions and what proving them gave you confidence around and then moving really aggressively to do that. We tool everything. We measure everything that is startup table stakes at this point, but asking those questions and really from the start, having a sense of what you need to learn to feel confident that you're investing your time in the right place has been critical for us.

AI assessment note: “being very methodical about what questions we needed to answer that gave us confidence”

Q Yeah, no, absolutely. I mean, I completely understand the courage and risk-taking ability it must take to do that. I mean, what are the core challenges, though, to implementing this? In some cases, kind of the burn the boat strategy.

A I think you should always have an initiative that you are working on that a huge portion of the team and investor base is afraid will kill the company. Like, that is a good barometer of, like, are you being daring enough? And most people are Are going to tell you just the same way when you start your company, most people tell you it's a bad idea when you're like in the process of building your company, people are going to tell you that stick to these paths that are kind of clear and have been paved before you and where you have traction and it's easy to fall into that. I think being willing as a founder CEO to look at that data and think about your big vision and where you're going to get need to get to and continuously being willing to risk it all to make that next jump. Is absolutely critical factor in, you know, these companies that kind of go on and become staples of our daily life was their stories of them doing what it wants to do.

AI assessment note: “most people are going to tell you that stick to these paths”