Ep37: Venture Studios & Conscious Leadership; w/ Jesse Pujji Founder & CEO @ Gateway X

Hey, Jesse, welcome. I'm so happy to have you on today.

Thanks for having me on. I'm excited.

Yeah, there's so many things that I want to talk to you about— Startup Studios, e-commerce and performance marketing, your journey in conscious leadership, etc. But I was thinking, where do we start? You had written a tweet about a 2005 meeting you had with Mark Zuckerberg. You and a college roommate had started a Facebook competitor and ended up meeting with Mark at that time. I bring that up because Threads obviously is all over the news. In 36 hours, they've achieved 70 million signups, which is incredible. So walk us back to that meeting, what you thought, what that taught you about vision and leadership from Mark, and what your thoughts are on the Threads app.

Yeah, I mean, look, at the time, we had launched a high school version of Facebook. And had heard through we actually there was this domain hsfacebook.com. We had tried to buy it three months earlier, and the guy asked for ten grand, and we were like no way. And then it was August of 2005. We were going to be seniors in college, and we get a call from the guy, and he's like, "Hey, Mark Zuckerberg wants to buy this." So like, are you sure you don't want it? And we didn't care about the domain anymore, but we were like, "Oh no, is Facebook launching?" Into high schools, like and and I think we had made a there's lots of mistakes and miscalculations. But one of them was we thought you know Facebook's never going to launch out of colleges. Like it's it would lose all its brand, and so there's going to be this opportunity to have different social networks, which was totally wrong in retrospect. But a lot of it goes to your point around vision. He had a huge vision, and I always tell my my Ampush co-founder Nick. I always credit him as being more of the visionary between the two of us because at that time him and I would debate this, and he goes, "I think it's going to be like your license." like, it's going to be your online identity. And I'm like, no, it's never going to get that big or whatever. And so we had to find out for ourselves. And, you know, we, we were very resourceful. And so we like said, prove it, you know, we asked the guy, hey, prove it. So he forwards us an email from Mark Zuckerberg that has his phone number. And so we call Mark Zuckerberg. And I didn't say this on Twitter, but like, we didn't really identify ourselves, you know, we weren't being perfectly transparent. We were like, oh, yeah, decoy. Little coy, like, yeah, this guy said he has this domain. And, and, you know, he spends like 45 minutes telling us his whole strategy about how it's going to be colleges and workplaces, then it's just going to open up. And, and so yeah, I think, I mean, I actually don't think he gets enough credit as a visionary. And he certainly is one. And I think the other thing is like most entrepreneurs who achieve big outcomes, they have, or any outcome for that matter, have vision. Like it's an important thing. It's actually something we teach at the Venture Studio. We call it DFS, Desired Future State. And we use the example of John F. Kennedy in 1960 saying, I'm going to land a man on the moon. And that one, it's such a good example because it was so impossible. The idea of asking how you were going to do it at that point made no sense. You could only say, we're going to land a man on the moon, and then everyone had to kind of figure out how to get it. I teach entrepreneurs and CEOs at the studio, like, it actually, you want your DFS, you want your vision to be divorced from reality. Because the whole goal is to like build to that vision and figure out how to build to that vision. So yeah, I think it's a very important data point that it wasn't an accident. It wasn't random. Like, he really had the vision for what they ultimately built.

You need vision, execution, and luck. You kind of need all 3. Yeah. So today, as we're recording, it's 2 days after Threads was released and they're at 70 million users so far. I believe you are user 300-something or some crazy early number. 1,500, still crazy early. And very smart growth hack that they put that number on the Instagram profile so that people have that kind of, that status symbol. So talk to me about your initial impressions there. achieved pretty broad success on Twitter in terms of followers and reach. What are your thoughts on Threads?

Yeah, I mean, look, when you see what happened with Reels and Stories, you know, I think they've proven kind of like Microsoft, the ability to take something working well for someone else and replicate it and make it better and work better. It's gonna be interesting to see, you know, I think they have a the chance of, of taking a lot of share and figuring out how they get those conversations shifted over. It's so early. I think the one other thing people are underestimating is like how much they have the ability to invest in it, but also the just like the patience and the knowledge to get it right. It's not like they're— it's not, you know, in the high list in our little high school Facebook. Facebook launched in high schools within 2 months, we were interviewing for jobs. We didn't have that commitment and dedication. And I think they have the maturity, the dedication, the commitment to actually see it through in an interesting way and get it to a certain place. So, you know, I actually asked the question on Threads. I was like, what do you think they have to really get right? And there's a ton of different answers for it. I think it's going to be scale initially, which I actually don't think they have a problem with. But then I think it's almost like, how do you shift the conversations over? And, you know, for me, like I said this very clearly, like I have 170,000 followers on Twitter. I think now I have 1,000 on Threads. It's been an interesting experiment, by the way, to see like Jay Shetty, he already has 600,000, like people who truly have audiences. Like, it'll be interesting to see how much of my audience kind of carries over or how that plays out. But like, if I had a bunch of my followers on Threads, like, you know, I might start to just focus there. And so it's hard. I mean, what they're doing, I think, is super hard. I do think there's other features like DMs and stuff that are missing that feel like a really important part of the Twitter experience. But I mean, if I were Elon, I'd be pretty nervous right now.

Yeah. So you see it as a potential Twitter killer?

Yeah, I think, I think it's a— it's hard to imagine that they're gonna like split the world. Maybe they will. You know, like maybe, maybe this short-form written content will become big in the celebrity circles on Threads where like the business stuff stays on Twitter or something like that. Because like business Twitter feels like a pretty big thing. The rest of Twitter doesn't feel— maybe, maybe it is. I'm just not in those, in those discussions. But I generally think it's a one or the other kind of thing. It's a binary thing.

Right. One of the points I saw made about Threads, the building on top of Instagram is a huge unlock, right? It gave them immediate audience and not just the user adoption, but also they're coming with their graph. The problem is that people's social graph isn't the same from network to network. So the people I connected with on Instagram aren't the same people I follow on Twitter or connect with on LinkedIn or whatever. And I have different circles, you know, kind of going back to the Google+ idea of like circles, literally.

Yeah.

So it'll be interesting to see if people kind of want that, where it's melding into one kind of social network, so to speak, where you have your Instagram connections are your Threads followers. definitely helped them unlock that kind of that day one challenge of you come into a network and there's no content, there's no followers, there's no conversations happening. So they were able to overcome that.

Yeah. Well, you know, Austin Allred is on Twitter and he's kind of like a Twitter friend of mine. And he made this post that was like, you know, all of my friends hearing the unfiltered thoughts of all of my friends from high school is like kind of a special place in hell. Like, I'm not sure I want that. Versus like you said, Twitter is like, you know, business luminaries and people on there. So, you know, I was in super early before it opened up before everyone. And there was actually another interesting moment because there was all of these influencers, like all these people, and everyone was responding to each other. And at one point, someone, I think Mark Cuban said to Mark Zuckerberg, like, are you sure we want to open this thing up? Like, it actually made me think like there could be an idea for like a, you know, influencer-only, like social, like you have to have a 100K or more on some platform to join this other social network. Because it was interesting to see how people were, you know, at that stage, prior to it opening up for public release, how, how people were engaging. It was very intimate and very positive.

Yeah, you're— what's the name of that dating app? Raya, which is like for celebrities and influencers only. Clubhouse kind of followed that trajectory as well, where early on it was, you know, they had a really diehard Very small cult following, but as soon as they opened it up, it was the beginning of its downfall where it just became too noisy and everybody left aside from, you know, COVID factors, et cetera. It's fun though. You know, we were in 2010, going back to you, 2005, you know, seeing what's the new social media network, what's— and, you know, who would've thought 2023 would be having the same conversations about, you know, similar topics. You talked about your venture studio earlier, GatewayX. I'm very curious about the business model of a venture studio, and also your thought process around why launch this type of platform as opposed to kind of like a, like a tiny, right, where you're acquiring existing businesses or, or an accelerator, kind of venture investor? Why the studio model? How does it work? And why did it appeal to you?

Yeah, yeah. I mean, I, you know, there's so many of these different kinds of models out there. There's holdcos, you know, there's holdcos that buy failing startups, there's holdcos that buy mechanics businesses, there's venture accelerators, there's venture incubators, there's venture studio, like, you know, there's so many of them, like, even kind of explaining it to people is different and can be more challenging. And they all seem very interesting. I think You know, for me, I, a lot of my journey to get to starting GatewayX was really a personal journey. Like, I don't, I don't know that it's the right answer, quote unquote, or the one that's going to maximize value or whatever. But it's the thing that I think gets me most excited to wake up every morning and go build and go do things. And so, you know, when I was kind of post-Ampush, I was thinking about what to do next. I was like, oh, should I be a VC? Should I go start another company? And there's just something in between that started to appeal to me. I was like, I love the process of like getting my hands dirty, getting the thing going. I love that first 12 months. I love ongoing strategic involvement in things. I don't necessarily love after the first year or so the nitty-gritty of what it takes to run a business, having the weekly meetings and checking on everyone's to-do list and making sure it's all getting done and building that machine. And I'd spent 10 years, you know, running a business where I was doing a lot of that. And, and I love coaching and teaching people. And really like being able to share and see other people learn and grow. And so I'd been exposed to all these different models. And, you know, being an investor felt a little too far away from the action. Being the CEO of a, you know, early startup also felt like, oh, that's too much. I don't know if I want to do that. And this ended up kind of becoming a happy medium for me where, you know, and I'm friends with the founder of Atomic and Redesign, like some of these studios, and I like, I would meet with them and kind of go, oh, this is super cool. You're You guys think about the world, you come up with ideas, you develop them. And then I wanted to kind of think about what my unique spin on it would be, sort of how do I make this my own or my own orientation? And so there's at least 3 things that kind of make us unique. I'd say one of them is we have a common cultural operating system across every business. That's really things I feel strongly about everywhere from how do we run a meeting to how do we give feedback to each other. And as a part of that, like, I'm very involved early on with the— I'm like essentially a co-founder. You know, some of the studios operate where the person's a little bit more removed and they give money and they give a check and then they have an idea. I'm like co-founding the businesses with the CEOs, at least now. And I plan to keep doing that. And I don't necessarily want to build lots of companies. I want to build one, one good one every year sort of thing. So that's the first thing is that they all kind of have a similar cultural operating system. And we kind of run it almost like a holding company in the sense that they're all You know, sitting in the same building and so on and so forth. The second thing is all of the ideas tend to be kind of capital-light ideas. And what I mean by that is like they don't need a lot of money to get profitable. They should be able to kind of stand on their own two feet within six to twelve months of launching. And so that limits all the ideas we go after. But it also I think there's a big opportunity kind of in the space between the mom-and-pop and the venture outcome-oriented businesses. And I think there's just not enough businesses being built in that space. And so that's kind of the space we play in. And then last but not least is, is every business has to answer the question of sort of like, why should we be the one starting this? What's our unfair advantage in building this? Which typically means for me, it's either, you know, customer acquisition, heavy customer acquisition orientation, or a problem that marketers or brands are having, or something that I know, an issue entrepreneurs are dealing with, like it has to be an issue I know and understand well and/or have Unique distribution, kind of unfair advantages around. And so that's kind of the three things. Then we have a million ideas. You know, we're constantly. We probably have ten exciting ideas at any given moment, and we're having ten or fifteen conversations with potential CEOs. And we don't really force it. It's not like we say, okay, we must start this idea. Let's go get the CEO. We always kind of say, oh well, we have a lot of interesting ideas. Hey, let's pair you two and let's go work on this a little bit, and let's see if there's something there. And that's kind of how something gets going and gets started.

Interesting. So how does that play out practically? Are CEOs or potential CEOs coming to you with, you know, an idea, a project? Is it the other way around? You have ideas and you're recruiting the CEOs?

It's more the second one. But what I would say is like, I so far, again, like I'm trying not to force this, I guess is like an easy way to say it. Like I I have a lot of ideas. And I'm constantly meeting interesting people who want, you know, look to do something entrepreneurial. And a lot of times my conversation is like, hey, here's a bunch of ideas and areas that I'm interested in. Why don't we go, go explore one together? And hey, why don't you go talk to these few people who I know and come back in a week and tell me what you learned? And so it tends to be more like that. And then it tends to kind of come together organically, because Because, you know, starting a business, it isn't the same as— it's not the same as taking a job, in my opinion. It's something that really, you have to be ready for, you have to— your family has to be ready for it, there's an emotional element, ready for it. And so I found a lot of those conversations suss out very quickly if the person is truly ready to make that leap. But yeah, I think it's more of my ideas, my areas of interest, and then talking to interesting people. And then when the stars align, we do it.

What are the key qualities that you look for in those CEOs?

Yeah, such a good question. You know, one of the big challenges that every studio or holdco has— the challenge, the key challenge is talent, right? And there's this common refrain, which is like, well, like, you know, if someone's willing to take 20% of a company or 30%, like, they're not a real founder, they're not this. And that's kind of the refrain, a lot of like, kind of criticism of studios. And, you know, I started my first company, obviously, in a, in an open format. I didn't start it with a studio or anything like that. And so I get that, that discussion. But I think there's a lot of people out there who want to do it, but don't necessarily know how to do it, and are looking for that kind of guidance and that kind of help. And so I think the first thing we look for is coachability, that the person's open to learning, they want that feedback, they want to be a part of it, because it is, it isn't like on an island. I'm, I meet with every CEO every single week. We're talking about the businesses. I'm involved. Like I know what's going on with each of them. So coachability is number one. I think number two is on like ownership. That's like a kind of hard one to put your finger on. But I think one way I've found it as I as I've cycled through, you know, we've we've had one you know one or two folks who haven't worked out is for the like problems. Are they in front of me? Like I know as like my my type is like I like to think about the big dreams. I don't really like to sweat the details, but I have a lot of ownership, and so I will sweat the. Details when I need to. And so if I'm sweating the details and the CEO isn't, that's an immediate sign to me that there's a problem, that that person needs to be sweating the details more than I am. So that's an easy way for me to tell kind of, are they owning it? Do they own the problem? Are they owning the challenges associated with it? Then I have this very specific framework I've created, created actually with my old co-founder from Ampush. We call it entrepreneurial rigor. And so if you can imagine a 2 by 2 You know, there's, there's being entrepreneurial, which is like being bold and moving fast and being resourceful and being creative. And then there's rigor, which is like being data-driven, being logical, looking at information to kind of make your next decision. And the reason we actually made it as a 2x2 is a lot of people, they tend to say like, oh, I can either do a lot of analysis or I can move fast. And our argument is actually the best people do both of those. So they're able to move fast, triage, and sort of zoom in on what matters, get the next thing done, and then so on and so forth, kind of iterate from there. And so we look for signs of what we call entrepreneurial rigor. And then the last thing is, is, you know, I've said it already, but unfair advantage. And so I don't, you know, I have my unfair advantages in starting businesses. I also want this person to have some kind of unfair advantage in what's going to make us more likely to be successful in the business.

And that could be a specific skill, it could be a network, it could be anything.

Yeah, yeah, exactly. They know something just about a bunch of other people don't know. That could be they've, they've done a lot of these kinds of things in the past. Like, you know, examples would be for Growth Assistant, you know, for Adrian, like she had, she had been an HR recruiting ops person for 14 years prior to starting the business. So the, there's a lot of focus on my Twitter and my network and getting, getting that business growing. But she had to have the ability to stand up recruiting organizations, place the right people, match the right people, like that was critical and has been critical to the success of the company.

Yeah. And we had Adrienne on the podcast. I loved my conversation with her talking about Growth Assistant and the advantage you get from outsourcing. I'm actually getting close to getting my first Growth Assistant. So I'm excited for that. I've been pushing it off a while because I'm— I have trouble delegating, but we're gonna do it. So, so back to the model of the, of the venture studio. So, so the CEO is getting what you said about 30% equity, you're putting in capital, operational support, marketing support, get them off the ground, but they're running the business day to day, you're, you know, kind of more of like a chairman role, right?

Yeah, like a week to— I would think of it as week to week. I mean, I'm meeting with everyone every week, reviewing kind of how we're progressing against the plan. Helping them figure out what's going on, you know, where we can play in, where not to, and then on a regular basis kind of planning. And then there's various places I'm digging into the companies, might be helping with marketing initiatives, maybe helping with sales. So it's sort of, I think of it almost like the football analogy is like the free safety, just kind of like, where am I needed on the field? Where do I need to go to?

Got it. So why with Kahani specifically, you took a CEO role You've stepped in there. Also, it's the only company I think that you've taken outside venture funding as well. You've traditionally with Ampush, with Growth Assistant, with other companies, you've bootstrapped. And with Kahani, you took venture funding. So what's special about that opportunity? Tell us about Kahani. And also why, why did you see that as more fit for venture-type business as opposed to bootstrap?

Yeah, yeah, that one's actually been a pretty interesting learning. I don't— I'm not sure we've talked about it much publicly yet. But, you know, the answer initially to your question is we, we saw it as a very compelling SaaS opportunity where we thought there was a big, big opportunity if we cracked the code on it. And, you know, meaning we said, like, look, vertical media, the way that, the way that current e-commerce experience works is very dated. Look at how we use TikTok, look at how we use Instagram, the experience should look and feel more like that vertical media, pictures, video should be a rich experience. And we said, gosh, that feels really real. And, and at the same time, I don't know exactly what's going to work and what's not going to work. And so it's going to take money, it's going to take time, it's going to take real experimentation to kind of figure out if there's a there there. And that was the initial reason we said, you know what, this one feels like one we should raise money for, because there's a big, big prize. But more importantly, like, we don't actually know, you know, it doesn't have product market fit. And it's not obvious from the get-go that it's just going to work. Which is very different than say Growth Assistant. Interestingly, like as a part of the fundraising process, you know, originally I went into the fundraising process saying, well, I'm not going to be the CEO, we're going to have a CEO, we're gonna find a CEO. And then through that process, everyone's like, well, hold on, we're not going to invest in this unless, unless someone's the CEO. And so I was like, alright, alright, I'll be the CEO, I'll be the CEO. And I said, oh, you know, that's fine. I've done it before. And, you know, we haven't talked about this publicly. But in the last few months, I've sort of had this I've kind of been honest with myself around like that's not actually what I want, and eventually honest with the investors and and said, "Hey guys, I know I said I would do this, but I this is not. I'm not. My cup is not being filled by my day to day here," and we've actually gone through a pretty big restructuring process. And and so we are we are you know Kahani's going to continue to operate and run. We are shifting the business a little bit. We did find a CEO for it, but we've sort of changed the way it's structured. From what the original idea was for it. So that's a.

So tell us about the new Kahani.

You know, the the first version of it was like bringing stories like Instagram stories into into the e-commerce experience, and I think it was a little bit of a of a solution chasing a problem. I think one of the things we learned as we went through that was oh, a lot of people want like influencers are really important part of the business. And that's how people buy ads. And a lot of the brands seem to want to integrate their influencers a lot more with their, their actual site experience. And so the Kahani 2.0 is essentially, hey, imagine almost like an influencer microstore, but using vertical media. So you still have the thesis of like, hey, you land, you see the ad that says, hey, this is Jesse's water bottle company, come check it out. And then you land and instead of just landing on the brand page, it's Jesse's page and Jesse's still there and he's saying, Hey, it's me. Look at the button. Just buy it below. So almost it's like a landing page slash influencer microstore solution that we think can perform really well. And that's sort of the reboot idea that we're playing around with now.

Fascinating. So would that be for influencers that are launching their own branded products, or would it be for companies that are leveraging influencer marketing, or both?

It's more the second one.

Okay.

Yeah. Yeah. So the idea is like, you know, a brand like Boll& Branch, for example, has Tens of influencers, and they notice that when they put the call out the influencer on landing page, they they see a big improvement in conversion rate. So how do we make that more of a tool and automation? And then the vertical media. One of the challenges with like the the idea of the observation of vertical media needs to be integrated into the ecom websites. Like that's a it's a good observation, but you have to peel the onion many more layers than that. And it's kind of like well what content is going to be the content that gets people to buy? And everyone in e-commerce they need to know how their needle is going to be moved or they're not going to buy something. And so that was sort of, I think, one of the challenges we ran into is everyone's like, oh, it's a cool idea. But it hasn't, you know, it's not quite hitting my pain point the way I want it to.

Fantastic. Well, not uncommon for companies to have to go through that trial and error kind of learning journey to find product market fit. And it sounds, it sounds great. You're built on top of Shopify as a Shopify plugin, or is it—

The Shopify app?

Yeah. So the next question actually comes from a listener, Sam. He's a repeat or serial entrepreneur, and he's considering acquiring a Shopify plugin business and wants to know, are they different fundamentally from a typical SaaS business? What else do they need to keep in mind thinking about valuation and/or kind of growth potential of a Shopify business or Shopify— sorry, not Shopify business, Shopify plugin, as opposed to traditional SaaS business?

Yeah, yeah, sure. I mean, I have a couple thoughts. I'm not sure I'm the expert on it. But, you know, one thing I would check is like, do you really want to be in the business of acquiring something? And kind of like, the analogy I always give is like, if I were to build my dream home, I wouldn't buy someone's house and renovate it, I would start it with a you know, plot of land and blueprints. And that was a big thing for me in making my decision. Like I thought about rolling stuff up and some of these other things and then decided, no, I want to, I want to build stuff from scratch. I'd first say just double check, you know, if you're an entrepreneur, do you want to, you know, rehab someone's house? Or do you want to start your own house from fresh? Because sometimes there's definitely things that can accelerate when you buy something. But there's also a lot of other stuff to work through when you do that. And then, you know, Shopify is great in the sense that it gives distribution initially and works across a bunch of things out of the box. It doesn't The Shopify store is not as powerful as it once was. You are, you have to understand their APIs, obviously, like, you know, when you're building on someone else's platform, when they, when they sneeze, you get a cold. So you have to stay really on top of that stuff and figure out exactly what's, you know, what's what around that. And then the last thing I would say is, you know, again, I said it earlier, but like ecommerce, you really ecommerce more than most customers are very, very pain point oriented. So you either have to find a way that you convincingly make them more money without any doubt, or you have to be solving a really annoying pain point. And so I'm not sure I would buy it, or, you know, if you've already bought it and you're trying to build it, I would make sure that that's how you're thinking about what you're doing.

Yeah. So let's talk about e-com and I guess performance marketing or direct-to-consumer marketing. You did a lot of that with Ampush. You guys were at one point one of the biggest Facebook spenders. Helping some of the biggest direct-to-consumer brands. There was a huge boom in D2C, both in terms of number of companies launched, the amount of venture financing they were getting. But I saw a stat that there were, out of all of the D2C companies that raised over, I think it was like $20 million or $30 million, there were only 2 or 3 that have achieved, that have sustained the unicorn status or unicorn valuation above $1 billion. Most of them have struggled to kind of maintain that valuation. So what are your thoughts there? I guess going back to the conversation around like VC financing and venture-backed versus bootstrapped or whatever you want to call sustainable business model, is D2C just not fit for Venture funding? What do you see that going?

Yeah, that's a great question. I mean, you know, if I had a gun to my head, you didn't ask that question, I'd say it's not a fit. I think the reality of it is a little more nuanced, which is it's for the amount of money a lot of these companies raise, they just raised way too much money. And, you know, when you think about how venture financing works, like, The consummate examples of a venture-funded business are on the consumer side are Uber or Facebook. On the enterprise software side, maybe something like Snowflake. But really on the consumer side, it's something where every time they get money, they're likely to become monopoly businesses or businesses that are going to own an entire market. And every time they get more money faster, even though they're losing a lot of money, They it's gonna it's gonna contribute to them becoming like a tens of billions or hundreds of billions type of business. And gosh, it's just there's so few of those actually, right? In the actual world, enterprise software is a little bit more interesting because you don't actually have to have a monopoly to build a multi-billion dollar business. But they to different degrees enterprise software has had this issue. And then you go to D to C and you go well, you know the only like. 8 and 9 billion, you know, or whatever, tens of billions or hundreds of billions of our businesses are like P&G, you know, or, and those are a conglomerate of, I don't know, 100 brands or something like that. And so I think the reality of it is, the idea that any of those things are going to become true venture outcomes was very rare. Now, what's interesting is like, if you were Casper, or you were Allbirds, or any of these guys, and you raised only $10 million, You would be a huge success. But I think this is where really the important issue is, is like, well, raise $10 million, then figure out how do you get profitable. But I don't know if it was, you know, it's always a mixture of entrepreneurs, their boards, they all kind of said, well, hold on, let's go, let's go for broke. And everyone's very short-term oriented. They said, well, everyone's, our valuation keeps going up, let's, let's lose more money, let's grow faster. And then, you know, the market turns. And everyone who's never lived through the market, a lot of these entrepreneurs, a lot of the VCs even had not lived through a market downturn, they just don't know what to expect. And the market turns, and then it's not. You know, I don't know if you're a finance guy at all, but like if you do your DCF and you double the discount rate, like your valuation gets cut more than in half. It can come down a lot, right? And so, if you lose profitability and that's valuable, then you lose growth. You just end up in these situations like you know the Allbirds or whoever of the world where they went public or Warby, and they're just worth a fraction of even what they raised in venture. So they just raised too much money. I think that's the— that's what I would say about them. Like, I think, is there a model where you can fund, I don't know, I'll make up a number, $2 to $10 million, and something turns into a $100 to a billion dollar type business, or $50 to $500 million? Yeah, I think, I think that's a very common thing. But I think one of the hallmarks of those businesses, they got profitable early on, they got very good at customer acquisition early on. And they were able to scale, you know, profitably.

What would you change about the venture world for to solve for this or in general?

Um, I mean, whatever, I, who am I to tell the world how to behave? But like, I think, I think there's way too much money in venture. There's just not enough great entrepreneurs and great truly sort of like game-changing ideas out there that require as much capital as there is in venture. Or maybe a nicer way to say it is like, some more innovation around the business model. Like, like, you know, the, the way Sequoia— the business model of venture. Yeah, yeah. Because like the way Sequoia invests, you know, Sequoia says yes to 1 out of 5,000 things. They expect themselves to make billions off of every investment they make, and a bunch go to zero. And that works. And then someone will turn around and start a VC firm doing D2C stuff. And they'll have the same approach to it, the same business model. And you go, well, no, hold on, that's not going to work. Because that business model is just a very different— you're investing in different types of assets. And I think I recently saw this thing that General Catalyst is offering for SaaS, some kind of like, almost like a revenue-based financing source where to grow your— they'll fund your sales and marketing. they'll, they'll take a portion of the incremental revenue you get from sales and marketing efforts. Like there was some innovation, whatever it was. And to me, I look at it and I go, yeah, there's a lot of different types of ventures out there. There should be way more innovation in the, in the, you know, in the capital structure and the types of capital that are given and for what they are. So I think there could be a version of, of in D2C where, you know, again, you gave a few million in equity financing, you found debt for these companies, And you helped them grow to 9-figure or in rare cases, 10-figure valuations. And that would be a great business for everybody. That would, like, it wouldn't make the entrepreneurs have to raise too much money. It wouldn't, the VCs would get good returns, but it's just, there's not enough innovation in the business model there.

Yeah, there definitely are a lot of companies that were being funded that didn't deserve funding, but I think that there's There's certainly a need for different types of funding. And what you mentioned, getting creative with how these businesses are funded. And, you know, SaaS businesses now have the opportunity to get basically cash advance on ARR for subscription revenue. So there are other models.

Yeah.

So you sold Ampush last year, right? That was— I don't know if the amount was disclosed, but it was life-changing money.

Yeah.

What was the day like when that wire hit your bank?

It was actually kind of a funny day. Because, because, you know, you do these closing calls, and you have a bunch of people on a call, you've like, the signatures have been signed the day before. And they're like officially released on a call, and then the lawyers, you know, give them to each other, and the deal's done, and the wires get sent. And then it was a little like, you know, we popped whatever pop—I don't drink—but we popped bottle and said yay. But the wire, you know, funny enough, the wire hadn't hit my bank account, and so like all day I was like I was like excited to celebrate, but I wasn't—it wasn't like done until it was done, you know? And that's kind of the classic thing. And so. I think it was around 2 PM where then I like looked at my— finally looked down. I was like, oh my God, that's crazy. And then I like, I was with my main co-founder Nick and I called him and I was like, oh my God, I can't believe this. And then it was really— so we did this closing, we went for a walk, we were both kind of waiting. I think there was a lot of anticipation and then it finally hit and it was just like a really like a huge release. And it was interesting what I've told people after that deal, like I stopped being the CEO in 2020. And if you'd asked me between 2020 and 20, you know, end of last year, I'd say no, I was on to my new stuff. Like, I, you know, I was in good hands. I was involved like as a board member. But I think now that it's done, I realized how much kind of RAM, RAM I had running in the background for Ampush. Because it was really the first company I had started. I'd run it for 10 years. And there's just, it's not even about the money. It's like, there's something about wanting all your efforts to be able to have shown for something. And so I think once we finally got it across the finish line, it was just like a ton of weight off the shoulders, relief, excitement. And yeah, and I think it was great for everyone else who'd been on that journey with us. It was just, it was, it is, it was much more validating and much more uplifting, I think, than I had given it credit for the idea of selling the business.

So it lived up to the hype, wasn't anticlimactic.

Yeah, I mean, look, I think the the day of or like the moment of is pretty anticlimactic, but I think like the the week of was not, if that makes sense. Sure. I flew home that night. I was in New York for the closing, and my wife had like you know all the kids had had ambush apparel on, and then she did like a celebration. So there was a lot of fun, exciting moments to it. And it's funny because we you know we we had a chance to sell the business in 2015. We actually you know between 2015 and 2022, we didn't the valuation didn't go up all that much. And so sometimes I'd be like, oh, why, you know, why'd we spend another 7 years on this when we didn't really change the valuation that much? One of the cool things that happened, though, was like, you know, my son was born in 2015. And, you know, now he's 7 or 8 years old, like, it has been really cool for them to truly see it and be a part of it. And that's like one cool versus being born. And all of a sudden, I had already sold my first company. And that's like in the history books from their vantage point, like, getting to celebrate it with them, I think was one of the cool aspects of waiting and doing it later.

Amazing that you found that silver lining in that. You've— you're actually, you know, I follow you for your entrepreneurial acumen, but also your advice on leadership. And I don't know what it's called, if it falls under the rubric of conscious leadership, this framework that has helped you kind of center yourself in your life, become a better leader, become more present. It's funny because I was just having this debate in my family WhatsApp group yesterday about self-help versus therapy and kind of like the efficacy and stigma of both. You and I think your wife as well have been, you know, in coaching for a while. Tell me about kind of how you approach that and you know why why coaching as opposed to therapy and what do you take from it? Yeah, yeah.

I mean, we could that could be a whole another podcast. You know, for me, I think there in 2017, I remember very distinctly feeling really stuck. You know, we had we had had a partial exit, so we had sort of a win. I think we were tired and sort of done. And, you know, but we were still running the business. And I just remember, like, I had this period, probably like 6 months where I just wake up, cancel my morning meetings, show up to the office at 11 o'clock, leave at 3:30. And I just was not feeling motivated and excited. And it got to like a pretty extreme level and started talking to people about it. And, you know, one of my mentors, he's just kind of like, you're like one of the luckiest guys I know. You know, you're young, you've made a good amount of money, your family is healthy and doing well, you're your own boss. And he was basically saying like, you've got it pretty good. The fact that you're feeling this way must mean like, he's like, there's some inner work for you to be doing. And he's like, go talk to a coach. And, you know, I did it open in an open mind. I said, yeah, that sounds like a good idea. Like, let me go talk to someone. And it was a very life-changing journey for me. I think I thought of myself as self-aware prior to that. And then I realized, like, there's like self-awareness within the month, you know, like, oh, last week, I was feeling pretty bad. And then there's like self-awareness within the moment, which is like, oh, in this moment, I'm feeling angry, or I don't think now's a good time for me to talk to someone. And I didn't, you know, I was self-aware, but not in that sort of minute-to-minute or hour-to-hour orientation. And That was a really big thing as a part of the coaching journey is like developing that kind of self-awareness, noticing my body, noticing energy, just all these things that I hadn't really done. The other big thing that I, you know, one of the first things that my coach said to me is we talked for a little while and he said, you know, you really use fear to motivate yourself. And at first I pushed back pretty hard. I'm like, what are you talking about? I'm not scared. Like, I don't— there's no fear here. And he slowly kind of broke it down for me. He's like, have you— you've used the word should 12 times in this conversation. You know, you said I should do this, I should do that. I, you know, this should have been this way. And he started slowly pointing out how I would, you know, it was really a revelation for me that, oh, wow, I constantly was sort of like, never letting myself fully enjoy a moment because I was like, oh, no, I should be doing this. I mean, next thing, what, where do I need to get to? And, and sort of how damaging that was. So that was just like a kind of blew my mind and like really, really got me curious about Why I do that? What other ways can you be motivated? So on and so forth. And then the last thing was actually this motivation, you know, question, which was like, why all of a sudden after so many years of working, you know, and I was questioning like, oh, do I really want to be doing Facebook ads? Do it? Did I want to be doing a, you know, tech-enabled services business? Like, I kept all these, like, you know, what he would call content versus context. He was like, I think what really happened is you were totally motivated by success to try to get, you know, Millions of dollars through an exit. You got it. It wasn't as good as you thought it was going to be. And now you're sort of lost. Like you have, you have, you don't have that same motivation because you've, you know, you kind of hit the goal you thought you were going to hit. And I think he kind of nailed it. And I was like, yeah, you're right. And so I was like, in some ways it's great. I was 31. I was like, oh, what do I do now? But it was really a moment of like kind of revelation. And so I've worked with him pretty consistently, you know, since then. And it's been a really, really, you know, I think the biggest benefits of it, I think, definitely, like, just self-awareness, being present, kind of all that stuff has gotten a lot better. I think I've become a much more capable communicator. And a lot of life is about clear communication, having a clear agreement, being able to share what you're feeling without attacking someone. And then I think last but not least, really being able to kind of like know purpose, like have a very clear sense for why I'm doing what I'm doing, and aligning my, my why with my what, if that makes sense. And so yeah, I couldn't, you know, I, it's one of the first things I tell any CEO or founder, or anyone really is like, go get a coach, build that self-awareness.

Yeah. My therapist has told me, stop shooting yourself. So I can relate to what you're talking about there. And it's— you've talked about it helping you feel better in your day-to-day life. How has it changed you as a leader specifically as you're developing your employees and also the CEOs that are in your Venture Studio?

Yeah, yeah. I mean, tactically, we have every CEO get a coach. We have internal forums. We really spend a lot of time on kind of developing the whole person, the whole leader. I think for me, you know, there's a lot of different ways. I think, I think the— it's a very well-worn discourse that like the ups and downs of entrepreneurship are unbearable, and they're really challenging. And I think one of the things I try to do is help people see that it's actually not— entrepreneurship is not about ups and downs. It's really our own mentality that creates that feeling of ups and downs. Because we just constantly extrapolate, oh my God, I got this email, the biggest client in the world, they're going to close. Okay, I'm really excited. Okay, no, now my best employee quit. Now I'm really sad. And it's, you know, there's, this is one of the frameworks is facts versus stories. And it's like the fact that what's the fact versus what's the story you tell yourself. And it's really the stories that create those ups and downs, not the facts. The facts are kind of benign actually. And so that's a big thing for how I help kind of coach the team and work with them. I think it's also made me a much better listener. And like, you know, more— I'm not naturally very empathetic. That wasn't a skill I developed as growing up. But, you know, a lot of the times when I, for example, when I was the CEO of Ampush, if one of my employees came and said, oh, I'm frustrated, and this is happening, this is happening, I'd be like, oh my god, oh my god, I gotta fix this. I gotta— okay, well, what if we did this differently? What is it? And, and sometimes you'd have the conversation with the person, they'd be like, well, yeah, I guess you could do that. And like, It was just clear they weren't getting satisfied. And one of the things you learn through coaching is like most of what 90% of when someone says something or is complaining, they just want to feel heard. And I've become a significantly better listener where someone just says something to me and I'm like, oh wow, sounds like this is really frustrating. You know, here's the thing I'm hearing you say, is that right? And not only do they feel better, but I also actually understand them better. And I'm not always just jumping to solve the problem or fix it. And like everyone just needs an outlet sometimes to have those conversations. And I think One of the things that makes me a good partner or that makes the studio unique is like, I'm able to kind of be there for people emotionally. And I think that's such not a normal thing. And so it's been a unique part of the journey for me.

Amazing. Last question before we go on to our exciting lightning round. Digital advertising today, I know that you haven't been directly involved with Ampush for a couple years, but you're still Very heavily involved in customer acquisition, performance marketing. How is digital advertising going to change in the age of privacy as well as in the age of AI?

Yeah, that's a good question. I mean, I think there those two in some ways are are opposites of each other or like gonna counterbalance each other. You know, it's funny there was such a big concern around Facebook. I mean, it's funny because I get all these calls through these expert networks for for Wall Street guys like oh what's gonna happen whatever. And then if people forget now, Facebook stock dropped to $90 a share. I mean, there was a time when we were joking saying that like, Ampush has a higher valuation than Facebook. I mean, Facebook was trading at 6 times cash flow. And it made no sense. I mean, it's one of the best businesses ever in history. And the only reason was because people were freaking out that privacy and this Apple stuff. And look, I love both companies. But make no mistake, Apple is being strategic. They're, they're, you know, they're trying to take this ad market, and they're trying to fuck Meta and Facebook over. There's no— in my mind, there's no question that that's what's happening under the guise of like privacy. But this AI stuff, you know, it's, it's, it just, it was really a disruption to Facebook's business, but not a long-term, you know, thing that would hold it back as long as a lot of people are using their platforms, as long as they're getting all the signals they're getting at a high level. They can kind of continue to deliver great results, and advertisers are trying different ads and testing different things. And so, you know, now Facebook is close to $300 a share, and like nothing has really changed in their business other than people realizing like, oh yeah, the AI, like the newsfeed algo and all these other things, it kind of learned and it got better and it oriented around it. And so I actually think a lot like TikTok. I think a lot of these platforms will be just fine regardless of how the privacy stuff changes. They still have a lot of first-party data. That I think people don't realize. Like Facebook knows, did you stop on the ad? Did you click it? Like it? Did you? They have the pixel. Like there's still plenty of data even in a world where the connections aren't as strong. And then I think AI in general, you know, I'm not an expert or anything. I we are using it across every single business in some way or the other. For Kahani, we you know we're using Copilot to code. For Unbloat, we're using Jasper and writing copy with it. For growth assistants, we're training certain growth assistants in the AI tools like ChatGPT. So to me, it's almost like the internet. Like it's just a thing that's going to take over every part of the business or like software or computers. Like you're going to not live in a business without that AI. I think there's going to be lots of opportunities created on the back of it. We, I think of it very much as the kind of thing that it's going to make the end products a lot better because the first drafts are much easier to create. And, and that's kind of the way we've approached it so far. So that's sort of my hot take on AI.

Yeah. Jesse, if there was ever a time where I was tempted to do like a 4-hour Lex Fridman-style podcast, it's with you because I want to go down each one of these rabbit holes, but I want to be respectful of your time. So we're going to close out with our exciting lightning round. I'm going to ask you a few questions. Tell me the first thing that comes to your mind. Sound good?

Yep.

All right. What's the book, newsletter, or podcast that you find yourself recommending most often?

Probably 15 Commitments of Conscious Leadership, the book.

Okay. Definitely going to add that to my reading list.

Great CEO Within is probably an honorable mention.

Who wrote that one?

That's Matt Mochary.

Okay, cool. What principle or core value do you live by or try to live by?

Oh, that's a good one. I think the biggest one for me is sort of like, everything is figureoutable. Like, be tenacious. Like, there's like, you can, you can get, you can solve any problem. And you can figure it out.

Okay. What's, what's one thing that you learned from the following people? Rick Elias?

Act like you own your business, not like your business owns you.

Cool. Alex Lieberman.

Work really hard to create unique content.

Adrian Schwager.

Put people first.

And Patrick O'Shaughnessy.

Questions are more powerful than statements.

Love it. Last one: What piece of advice has helped you most in your career, in your life, and any advice that you have for early-stage startup founders?

Yeah, I think the best one honestly is just keep going, like keep grinding. I could say a lot of other things, but. I think that dedication, that commitment, especially for early-stage founders, it you know it doesn't mean you stop thinking. It doesn't mean you blindly charge forward, but constantly you know see what's working, what's not, and keep moving forward and keep changing and like get out of your head and just do you know do as much as you can. Action is worth every ounce of action is worth a pound of thought. Let's put it that way.

I love that. Thank you so much, Jesse. Really appreciate it. How can people find you if they want to stay in touch or continue the conversation?

Yeah, I guess Twitter or Threads, @jspujji, just my first 2 initials, JS, and then my last name, P-U-J-J-I, or jesse@gateway.xyz.

All right. I'll put all those links in the show notes. Jesse, thank you so much for spending time with us, sharing your experience, your wisdom. Really enjoyed this. Learned a lot. Hope you feel better. Wishing you tons of success with all of your businesses, and hope to stay in touch.

Good to see you.