Jesse Pujji Reveals How He’s Building His HoldCo (Gateway X)

Jesse Pujji built Ampush into a $2M/month ad agency in 12 months, then created GatewayX, a holding company with four portfolio companies. He prioritizes hiring talent from top firms, building internal capabilities instead of outsourcing, and rapid customer validation over polished products.
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Jesse, welcome to the show.
Thanks for having me on, Tom.
It's an absolute honor. And there's probably about 15 things I want to ask you. And the first of which is you have experience at, I believe, both McKinsey and Goldman prior to the entrepreneurial days. What are like one or two things you learned from that experience?
Oh man, I learned a lot, a lot more than one or two things. But if I had to pick the top one or two, I think number one is just talent. You know, those places are just magnets for talent and it's not by accident. They, they spend a ton of money, time, energy. They go to the best college campuses, they go to the best business schools. They care about building their brand. When you interview at either of them, you interview, you have, I don't know, 8 interviews and you have very rigorous interviews. They're not just let me get to know you. They are deeply checking your brain to see how you think and see how you work. And arguably that was one of the most important things for me in my career is that as a young person, I saw that, I was like, oh, that's just how you do it. I'd never seen anything else. So I brought that into all the things I've started and it's been just a critical— and, you know, it's hard to get to that level, of course, but to the best of my ability, I got to that level. And it's a big part of the secret sauce of Ampush and some of the other successful ventures that That we built. So I think that's probably number one across both of them. You know, I think number two is they they both emphasize the importance. It kind of relates back to talent, but of skill building and practice, I'll call it. You know, like we get into business, we get into entrepreneurship, and people go, "Oh, we're selling." And then you go and talk to someone, you go, "Well." All 3 of your salespeople do it differently. You have never even listened to a call that they've done before. Like, yeah, I'm busy doing a bunch of other things. You go, well, no, hold on. You gotta teach them how to do this and you gotta drill them and you gotta make sure they're, they're saying it right. Those environments are, are both very intense about learning and skill building and practice. And, and how do you, and it's not, the other thing I, I'd call out that I think is super, super important is it's not like a, another thing you do. It's not like it's, it's ingrained in the culture that the person above you is giving you feedback and the person above them is giving them feedback and you feedback. So the learning environments, I mean, they're just, they're just machines in terms of building skill. And I think that's another critical thing that, uh, those are 2 things that I feel like startups still to this day don't necessarily emphasize enough that were really formative for me.
I did see a tweet from you today saying that one of the things you advise founders on is that they're probably overspending on external providers and underspending on internal development. So I assume that's a similar Thread to what we just discussed.
Yeah. Yeah. I think, I mean, you know, a lot of founders aren't interested in building companies, in building organizations. They're interested in building businesses and they're interested in making money, which is nothing wrong with any of those things. But I think it's, my passion has always been in organization building, even from when I was like 24 years old. I wanted to build a thing, like a thing, a company, a group of people. And so decisions oriented me in that direction. And I think a lot of founders, they want to go, you know, fast. And everyone fall— I fall, I fall victim to this or I do this all the time too. So you get this agency, they'll plug it in, they'll solve the problem. Right. And the reality of all these problems is they're moving targets. They're never— even if you solve the acute problem, you have this moment in 2 months, it's different. And that's what makes it so hard. And look, I ran a business that was a third-party service provider, so it's not like I'm against them wholesale, but, but I think, I think you just mind your, you know, the, the silver bullet mindset is, is a dangerous mindset that founders often bring and they just want to build a business that makes money. They don't want to build a company. They don't want to build an organization.
I heard Jason Fried say on a podcast I listened to yesterday that businesses are products too.
Yeah.
So that totally aligns and So this, it kind of makes sense to me that you're like passionate about the development part and the organizational building because the companies that you have built and are building are from mostly from what I can see, tech-enabled service businesses.
Yep.
And so people development is crucial there. So let's jump into a couple of those and we'll start with Ampush, obviously. I love, especially with agency or tech-enabled service companies, trying to understand like the ones that do grow, like what is it about them that grow? Because there's so many of them and only a small percentage get to the size that you did. What do you think it was about Ampush that enabled you to do that?
Oh man, there was a lot of things. You know, I think a couple funny stories. I mean, you know, one funny story, if you talk to anyone who worked at Ampush, I refused to call it an agency. It was like a joke. It was a joke with the clients. It was a joke with the employees. They're like, why does Jesse, And the reason, by the way, is because when we started it, I thought I was building a tech company. And now that was— there's some good things and some bad things about that. But you also have to go back to that time. Like there was a period where everyone believed there was going to be a social DSP because there was Pinterest and Twitter and Snap. And the idea was to have an ad platform that could buy across all of them. And the display DSPs had become pretty big businesses. And so the first 5 years of Ampush, or 3 to 5 years of Ampush, we were building a tech, like a tech-enabled— we thought it was a tech business. And then it became clear Facebook was going to become the 900-pound gorilla in the space and that there was just no point in having the tech the way we had had it, which was a huge loss of money and investment, actually. And then we became very, very tech-enabled services in the way we approach it. But anyway, that's kind of just a sidebar. I think there are a few big reasons. Number one, we were early. And I could— that's kind of like I call it. It's not lucky, but it's like right place, right time. We started buying Facebook ads in like 2010. And there's a backstory there, but it was just luck. We just happened to be in the world doing that, and that was very lucky. The second thing was, you know, this talent thing we talked about earlier. It's a good thread. Like, we, we went out and tried to hire search marketers or display people and try to get them to do Facebook ads, and we didn't find them to be analytically rigorous enough, and we just didn't find them to be the talent to be very good. And so what did we do? My 2 partners were ex-investment bankers. I was an ex-consultant. We're like, okay, let's go hire some bankers and consultants and teach them how to do this. And that ended up being a huge part of the secret sauce of the company. If you look today, Ampush is very well known to have the best growth marketing talent, and that's because we just followed that model. We went after the top 10 or 20 universities, we hired young people, we trained them how to buy Facebook ads, we trained them. But what we got was a bunch of people again who weren't— they weren't robots. They were— they were people who could evolve them, you know, as Facebook would evolve. We started Ampush prior to the Facebook Pixel. We started Ampush prior to Facebook News Feed. We started like, so we had people who were evolving with all of this stuff as we grew the business. And that talent thing was super critical. Then the third one was, you know, and this is kind of a funny one. I was not a marketing expert when we started the business. So I think a lot of people who start agencies are marketing experts who themselves get inundated. And so I actually from the get-go never wanted to be in the middle of any of the client services. Again, I thought of it as a tech company, so I was like, okay, I need to build my account management capability. And I think this was actually a really critical accident for us. And I would tell anyone who's an agency person listening to this, no, that's a function, that's a capability of the business. And so I was like, okay, there's a little pod, there's a leader of the pod, there's a person who's client-facing, there's a person who's ad management. Like we built these little— I called them Starbucks, you know, internally there was like a 2-year period where I would walk into a Starbucks with my wife and I would be in awe. I would be like, this place makes money and nobody here owns it. And there's just a bunch of hourly employees. And she's like, what is wrong with you? And I realized how hard it is to create people doing the same processes over and over sustainably because we got obsessed with that. We created these little McDonald's or Starbucks franchises. We called them internally, they were pods. And then once, once the pods worked though, then we could scale the business dramatically because We would just replicate the pod every time. And we had this formula of old, old people, new clients, new people, old clients, right? And we would just keep, keep replicating that. And that's what allowed us to scale. And so I think those are probably the 3 biggest things. There was a bunch of other little things here and there along the way, but I think those 3 kind of encapsulate 80% of it.
That's crazy. You got into Facebook ads prior to newsfeeds. So yeah, definitely nailed the timing. Is it true that you went from $0 to $2 million a month revenue in roughly 12 months?
Yeah, it was crazy. And it wasn't even in the Facebook ad. I mean, at that point we were running a lead gen business and because we had discovered Facebook, we just exploded on running. These was the right rail ads on the desktop. If you remember that time, we were making these hyper-targeted ads to 10,000 people who said they were art teachers saying, go get your art degree. At Kaplan University or Art Institutes, and we just—we were lead arbitraging. But we were able to just go as fast as we could because we had discovered this new channel. It was wild. It was, and it was all manual, by the way. There's no APIs. You had to do every ad in the interface. There's another funny part of the origin story, by the way, which is, you know, I started at McKinsey. McKinsey has massive teams overseas to do slide fixes and data pulls. So when I start— when I sat there and I looked at the Facebook interface and I said, we need to create— if we want to hit this number, we need to create 200 ads a day in Facebook. And again, back then you had to do it manually in like a— in an editor. There was no bulk upload tools. I was like, well, I'm not doing that. I don't even want my US. So I found a guy in India and I was like, you just— that was kind of the beginning of Growth Assistant, you know, 12, 13 years ago. Because then he started doing— every day we'd send him a spreadsheet and he would upload each ad individually. We'd wake up in the morning and the ads would be ready to launch. And that's how we scaled super, super fast on, uh, in the initial version of Ampush.
This is like absolutely perfect. I wanted to ask about this. I also spent 4 years before I was an entrepreneur in EY and Accenture working with these outsourced teams, mainly in India. And so when I was starting any business after that, it was just obvious that anything that could be done offshore would be. And so it seems like getting that experience before becoming an entrepreneur unlocks this operational secret sauce almost.
Totally. I feel like one of the learnings from Growth Assistant that we've had, you know, we have 125 clients and 400+ people now in Growth Assistant, and it is exactly what you just said. Like, to me, it's second nature because I had spent nights marking up slide decks, sending them over, faxing them over sometimes, right? And Then in the morning getting a nice slide deck done. And now inside of Growth Assistant, we called it magic moments. And I came up with that because like, I was like, whenever you offshore or outsource something that was on your plate, like making a slide deck all night, instead I got to draw it on a piece of paper and send it to someone who then made me the deck. That's a magic moment. You're like, holy shit, I can't believe that just happened. And so now what we do with customers is in the first month they have a Growth Assistant, we are— we require like we have an account team that's trying to create 3 magic moments for the client. By getting involved, what is what are they asking you to do? Okay, go do this because that person's gonna wake up the next day and they're gonna be like, oh my god! And then and then of course churn. The person never churns at that point, and you start to see the opposite, which is like they start hiring more more growth assistants, right? And so, but yeah, for anyone who's done it, it becomes second nature. And anyone who hasn't done it, it's extremely foreign. It's surprisingly foreign to them, and it's scary, and it's intimidating. And oh, I don't know if I don't have someone or. I've heard war, I've heard horror stories of it and so on and so forth. And, you know, one, one quick horror story. It's interesting. We tried to offshore engineering at Ampush many, many times for about 7 years. And just every time we did it, it was a disaster. And then we hired this VP of engineering who had worked with a couple of different teams in India and Ukraine. And, and man, he just crushed it. And it became this. And so it was interesting because It is, it isn't necessarily second. I mean, you, you do have to know how to ask for the thing you want to ask for. Um, and we see again, a growth assistant, more of our training goes to the clients than goes to the growth assistants. This is how you ask for this. This is how you set this up. This is why you, you know, don't, don't just say, can you check account performance? They're not gonna know what to do with that. Say, please open this document, then look at this number, look at this number. If this not, you know, you have to, this is how you have to, have to work with someone. So anyway, that's a, that's another sidebar, but an important one. Yeah.
We're going to get to growth assistance. Let's jump back to the Ampush story. So we eventually sold the company. And what I was wondering when I was researching is, could that not have just been one of the portfolio companies within GatewayX, which is the holding company/venture studio for anyone listening? Or had that not been conceived yet?
So we were the first, one of the first big Facebook tech-enabled services. We grew the business super fast. We killed ourselves, you know, from age 20, 6 to 31. My wife never saw me. I mean, it was, it was not healthy. It was all the bad things that, you know, and we got to 2015, we're like, we're going to sell this business in 2015. And if you, if you go back to the ad tech world at that time in 2013, 2012, there was like Rocket Fuel and Marin and they were multibillion-dollar market caps. And we thought if we got to $30-ish million in revenue in 3 or 4 years growing 100% a year, we'd sell for $150 million. That's what everyone told us. We went out and we were bootstrapped, so we end up getting like $75 and $60 million offers, all of which were great. But we were crestfallen. I was crestfallen. I was so sad and disappointed, which again, in retrospect seems so stupid. But, you know, that's, that's life. That's getting emotional and getting caught up in the moment and losing perspective. And so I think we, we were so tired and dead that we probably should have sold the business at that point at the best offer we had. Instead, we were like, we're not selling because all these people are wrong about our valuation, which was not true. They were all more— the market's never wrong. Instead, we sold a minority investment to Red Ventures, which was also one of the smartest things I've ever done because we learned so much from them. But we sold like 20% of the business for $15 million, some all secondary. So we did get a little bit of an exit, which was important mentally. And the goal was they were going to buy the rest of the business in 2 years. For a whole host of reasons, 2 years later, they said, we're actually not going to buy the business. We've changed our strategy, blah, blah, whatever. And then I was doubly crestfallen and I was like, oh God, what am I doing with my life? Why, you know, why didn't I sell? And I had— I was just in this really bad place. I didn't want to go to work. I, you know, I went through not depression, but I went through some version of like really existentially going, what? You know, and that's when I started working with a coach, and that has been the most life-changing thing that's ever happened to me. Why that's all important to your question is because after a year or two of coaching, I started to really dial in on the things that motivated me and drove me beyond money and beyond success. And what those things are, are number one, I love coaching and teaching people and creating that space for other people to learn and grow. That's like the number one why for me. And my sort of how, if you will, is through entrepreneurship. Like, I love building and launching new companies and I love that process of sort of the -6 to +12, 18 months. Well, as you guessed, as soon as I figured that out, I was still the CEO of Ampush. I'm like, great, Ampush is going to become that because I'm the CEO and I control it and I can do whatever I want. And I went really hard. We invested in startups, we bought a business, we tried— we called something internally called Ampush X. Which may sound familiar. And we tried to do all those things. And, you know, the big mistake I made in retrospect was I— the second I made that choice, I should have basically stepped away as the CEO of the day-to-day Ampush and put a GM in charge or CEO of Ampush in charge. Instead, I tried to run Ampush while these— all these things happened and none of them got the time of day because of that. They all were like, I was too busy running this core business to go do all those other things. So that was one huge mistake. Even then in 2020, we decided to do what you just said, which is like, well, why'd you start a new thing? But then by that point, the Red Ventures folks, my co-founder, like everyone just wasn't on the same page about doing it anymore. And so there was this moment where I was like, well, hey, I don't, I'm not, you know, I'm a big share— I'm the biggest shareholder, me and my co-founder and then Red Ventures. But if these, if 2 out of 3 don't want to do it, why will I do it here? So I just basically took a step away. And then whatever was in my head started in GatewayX. And so the short answer to your question is very astute. Yes, that was originally the plan. For a variety of reasons, it didn't play out. This is like my 3rd or 4th go at trying to make this vision a real thing.
And I must say, I actually only went on the GatewayX website. I think it might be new today. And I love the positioning. Essentially, it's a website or a brand to attract the entrepreneur. Like, that's the ideal person, visitor on that website, right? And you have the video testimonials from the 3. So yes, awesome.
And that's not just positioning, to be clear. I mean, we, we think of ourselves, uh, the clients here are the CEOs of the companies. And I think of my purpose, my why. And it's, it's really interesting. When I think of myself as how am I gonna make Growth Assistant successful, I find that I show up more in my ego. I show up more nervous and scared. And, and, and when I show, when I think of how am I gonna help Adrian be successful, I'm more inspired. I'm more, uh, open and curious and learning oriented and loving. And it's, it's the same thing in some sense, but that little framing difference, it is not just marketing, it's how we really process everything we do.
And I absolutely love the fact that the first 3 CEOs also are female. I think that's absolutely awesome. Yeah. Okay, cool. So, and we've been throwing around a lot of business names and so all the links to everything will be below, but just for everybody listening, we have GatewayX, which is the holding company venture studio, and then we have the companies within that. And there are 3. And then, so just to clarify then, Ampush is still out there. You own some still, I understand.
Ampush has been acquired. So we sold Ampush about 18 months ago to Tenuity, which is backed by New Mountain. It's a big roll-up of agency tech-enabled agencies. So I'm out of it completely now, which has been, which has been a, you know, I thought, I thought I could, you don't realize how much of your mindshare is going to something until it's gone. And now that it's gone, I'm like, oh yeah, it feels good. Feels good that it's done.
So your work life then now is 100% focused on GatewayX and also the kind of social media brand, which is almost separate, right? Bootstrap Giants.
Yeah. So I mean, I think you may have just learned a few minutes ago that we are, that's kind of the 4th business now. So we're going to turn Bootstrap Giants into a business. We've got an awesome CEO who we're announcing shortly. And the goal there is, Very spiritual for me, or very sort of my why, which is I started a company that I would consider a bootstrap giant. It grew really fast. It was bootstrapped, and I felt frustrated often when people would try to categorize me. And the 2 categories I got was either you can be venture-backed, ambitious, you know, going for a billion dollars, or it looks like a cute lifestyle business, Jesse. And I thought that that was unfair. I didn't like it. And I was like, well, hold on, there's another category here. And I didn't put my finger on it. And actually, Patrick O'Shaughnessy, of all people, helped me name it because I was like, what should we call this thing? Like, there is a type of company where the founders are ambitious, they want to make money, they want to grow it, they want to have an impact, but they're not venture and they're not lifestyle businesses. And so it's a bootstrap giant. That's what I think they're called. And, and I want to create the best content, the best community, like I want this. I want someone, people to walk around and go, I'm building a bootstrap giant. That's what I'm building. And there's just, dude, there's so much. It's crazy. Even now, if I post investor deck stuff on Twitter, anything about VC or investor, it goes 5 times more viral than stuff about bootstrapping. And it just shows you like, it's just, I want to create that path so that it becomes when a young entrepreneur is deciding what they want to build, they think of it as a very viable option with tons of materials and content and examples that they can, that they can operate from. So that's the, That's the passion and the vision behind that, that project.
I think that you nailed the name because initially when you think Bootstrap, you think small. And so it's just awesome. So in the portfolio then, I actually didn't know, I, I knew you monetized Bootstrap Charts, but I didn't know it was going to be part of like a GatewayX and like you guys were going to bring that into the portfolio. So awesome. So then there's going to be a media company. We have a DTC brand, Unbloat. We have Growth 15th, which I do want to get into the growth of that because that's been crazy. And then we have Aux Insights. So right now it's, or it will be 4 once you announce Bootstrap Giants, right? And so we have media.
We tried a SaaS business that we shut down. Yes. I was going to ask about that. So we did that and then, you know, we kind of, we've pivoted the brand. I think that we've found some things work better than others. Let's put it that way. We've learned a lot in building the studio. And I think the 2 biggest learnings we've had, I'd say one is The CEO again is the most important person, and you can't start the business before you have the CEO. Like it has to be co-created with that person versus, hey, I have an idea. Here's all this stuff. Hey, hey, you go run it for me. And you know, again, you see this on Twitter, and I always tell people like, I hate the word operator. Oh, I have my business here. You go be the operator for it. Like that's not how we think about it. We think of the CEO as the most important person. They're the customer of ours, of Gateway Access, and we formulate these things with them. All the ones that have had that have been very successful. The ones that haven't, Had that have have had their own issues. So that's that's number one. Number two is, you know, this may change in time, but at least so far, we have found that when we're when we don't have a tight perspective on the customer and the market problem, it we really struggle to dial in the business, and then we just kind of run out of money, time, or patience. And so we basically the way I framed it to you know the finance way I've said it or the VC way I've said it is. We don't actually want to underwrite product-market fit, like finding product-market fit. We want to know there's a market, we want to know there's a problem, and we want to stand up the solution for it. And Growth Assistant and Aux Insights, more than any two others, have both had that, and they've both been the most successful from a growth perspective.
That period, like pre-product-market fit, is the most stressful.
And it's so stressful. It just— yeah, it's been stressful. It was stressful for, for the brand. It was stressful for Kahani, which is a SaaS business. It's expensive because you're fucking running down all these different roads and you don't know what the hell you're doing. And it's not like anyone knows better than anybody else. And the difference in growth, this is Knox, is like you walk in and everyone goes, oh yeah, we like the— here's the best, by the way, thing we figured out for anybody listening. And this is like such a good bar to have. If in your 3 months of discovery of your business, you start this 3-month, like, let me go talk to people, see if it's interesting. If you start selling during that period, that means you have a good idea. That happened for both Growth Assistant and Ox Insights. We went, well, let's call some old Ampush employees and see if they need some offshore people. And I was like just playing the idea with them. We hadn't started anything. They're like, hey, can I get that person? And I'm like, sure. Okay, Adrian, let's go recruit someone, right? Or in Ox Insights, they're like, yeah, we need that. When can you guys start working on a project for us? And so Whereas a Kahani, man, it was, there were people who liked the idea and thought it was cool, but nobody was asking for it. And so anyway, I think that's, that's been a big learning for us that like we want something where there's a problem, there's demand, and people are asking for it. And that's just made it so much easier than trying to go find product market fit.
So if the CEO has to be there for conception, does that mean that the founder CEO will bring you the idea, or will you have an idea then try and find the founder CEO?
Yeah, we have the ideas. I mean, the idea is partly because coming from my brain, I have a lot of ideas, and I think the type of person who's attracted to this doesn't necessarily— they're like, they're the kind of person you go take a walk with, they go, I want to start a business, but I don't have an idea. And there's a lot of great people out there like that, and I'm the opposite. I'm like, I have a million ideas, I have no time. And, you know, so that's, that's a little bit of the connection. I think the other big thing is that we The best analogy I have for this is like, we just did the IVF process and like, they make a blastocyst, which means like they connect the, you know, the sperm and the egg and then the baby is like 6 days old. Right. So that's how much we, we don't, we don't get the ideas to pregnant, you know, we don't go through pregnancy and deliver the baby and then say, hey, go, go take care of the baby. We literally get it to like a 6-day-old and then it needs to be, you know, go through the process. And the CEO is really the person birthing it, if you will. Right. Like we're not the ones birthing it. So I think that. It's a— we do have the idea, we do have the seedling, we do have the idea of who the customers are, and we bring the customer. I bring the customers. That's a huge part of the value prop for them, which is, you know, if you're Adrian or Casey, I think both would admit that it would probably take them a year or 2 to get to where we are now because the customers wouldn't have been there. And I could accelerate that, which then is a huge flywheel. Like our first customer growth was DoorDash. Why? Because the 3 heads of marketing all worked for me at DoorDash. They all worked for me at Ampush. But guess what? The next time you go on the next phone call and you go DoorDash as a customer, your conversion rates double, your Twitter marketing, I mean, it all works better from that. So then same thing's happening with the private equity clients with Aux.
And that presumably is also why you are investing more in bootstrap giants because that can be a source of customers for portfolio companies.
Yeah, I think the, I will tell you that I started it because I wanted to just help share whatever I've learned with people starting businesses, bootstrap giants, founders. Also because I moved back to the Midwest and I was a little afraid I was going to fall off the map because I used to be in the Bay. And people said, hey, you'll get some benefits of it. I've been shocked by the reach of it and the benefits that have come from that reach. And You know, my COO at GatewayX, he moved from Boston to St. Louis. He's been in SaaS forever. Super talented guy. He looks around, he's doing something interesting in St. Louis. Boom. He sends me a LinkedIn message. You know, now we've been working together. He's like one of the best people I've ever worked with.
Shout out to Shonak, by the way.
Yeah, shout out to Nak. He— but it's just a great example. Like, but then the other— here's another crazy one. We walked into a private equity firm $10 billion private equity firm in Chicago. And I walk into the room and the guy goes, oh, Jesse Pujji, I read all your stuff on LinkedIn. I'm like, holy shit. Like, and so the reach of this stuff is way bigger than you imagine it to be. And I think that then— yeah, exactly. So then that's why we want to make Bootstrap Giants a formalized business, a place where there's constantly something out there. It also helps people know what you stand for. And I think that's been super valuable Because I'll have people opt in or opt out of conversations. Like if someone introduces me and they go, ah, I'm looking at what you stand for. Like, I wanna do venture stuff. Oh cool. We just all saved ourselves a lot of time and energy. Right. And the other person who pings me goes, oh, I see you talking about all this stuff. This is exactly how I'm thinking about the world. And, and so it leads to just some efficiency down funnel that I think is really valuable.
I wanna dig into your day-to-day at the moment. I assume some is on content creation. Summits with your CEOs, but I'd love to break down like the mix and anything else that is also included.
Yeah, it's a great question. My day-to-day, I've gotten, it's gotten a lot better honestly in the last 6 months. I think the best thing I have done around my calendar is created specifically schedulable space for the different companies on different times and different days. So my first half of Monday is, uh, like say 9:00 AM to 2:00 PM is for GatewayX in general. Like just catch up what's going on. You know, I, I work out Monday morning, so I come in a little late actually. And then the rest of the afternoon on Mondays is for Growth Assistant.
What does that mean when you say Growth Assistant? Like, what do you do?
Well, I think the most important thing is that they know that there's time there for them. So however they want to use it. And so sure, I might do a one-on-one with Adrian that, you know, we'll look at the business and talk through it. And that goes in 7 different directions. It may be a new initiative, it may be a coaching call with her, like, but it may also just be they have 3 deals on the finish line. And if Jesse calls the CEOs and says, hey dude, like, I'm here, I'm paying attention to this, it's going to help it close great. Like, I'll help him close the deal. So whatever they need my time and energy for, sometimes it's content. I'm available for that. Um, then Aux, for the most part, Aux is Tuesday afternoon and Wednesday day, all day. Um, or no, sorry, Tuesday, Wednesday afternoons. And then Unco, Unbloat is Tuesday mornings. Then Bootstrap Giants is Wednesday mornings. So I'm doing content creation, mostly content creation, some business stuff. Thursdays is all one-on-ones and various internal, just things across everything. And then Friday morning is Bootstrap Giants again. And then Friday afternoon is like networking and flex time, flex calls and stuff like that. So, so that's kind of how we've oriented it. I think over time we do think the businesses get more, more independent. Um, and I think Aux is the new business. Every time there's a new business, it like really takes a lot of my time and energy to get it kind of get that first crank of the of the flywheel going. And then once it's there, it keeps going. I think, you know, most of the people running these businesses, they don't want me in their hair. Like they want the good, they want to absorb a lot, get the customers, get any coaching, get the talent, talent that I might know. But then it's like, all right, dude, like let me do my thing. Like I— and so and that, you know, we're conspirators in that. Like I agree with that too. I don't— I also don't want to get into the operational aspects of the business. And so I think the hope is that even that, like even the current portfolio, Theoretically, I could absorb it in 2 days a week in a year from today. Uh, and we have plans for all that. It's not like we're just hoping for that. We have like, okay, well, over time, Jesse's not going to do this anymore, you know, and you're going to take on this and this is how this is going to scale.
How big do you think Growth Assistance can get?
I think in its current business model, and I'll come back to what I mean by that, it could be at least a 9-figure revenue business. And when I say current business model, what I— the most interesting part of the business is, let's use e-commerce. E-commerce is the biggest sort of vertical, but think of it as any startup marketing department. But e-commerce is super interesting because by our count, there's 5,000 to 15,000 $5 million plus e-com businesses. And by our math, they all need 3 growth assistants at least, right? They need a growth assistant to handle campaign management reporting and just all the like numbers and data that float around an e-commerce business. They need a designer to help with site updates and creative changes and iterations of video. And then they need like an influencer outreach and admin person.
What about the customer service?
It's not really, I mean, we will do it, but it's not, it's not really our bread and butter because it's, there's other people who are, it's kind of a competitive category. And I want to pick areas that we are, we can differentiate. And so, so those 3 roles are like kind of the, we call the Happy Meal of, of growth assistant. And now if there's, let's say, say even 5,000, even 1,000, if I can get 1,000 people to have that Happy Meal, that's 3,000 growth assistants, right? That's a $100 million business. So to me, in, in the current incarnation, it can grow there. As you get into these categories, as you know, Man, you realize everything is massive. Like, we're so lucky to live in a world with whatever freaking $50 trillion or $80 trillion economy across the globe and $20 in the US. And I'm fucking— my mind is blown constantly by how gargantuan this BPO staffing category is and all the different incarnations that exist. I talked to a company yesterday or a guy about a company yesterday And they have a genius strategy. They, they go around getting certifications in like HubSpot and Six Sense and ZoomInfo. Like they just run around all the software businesses and then they're, they're all outsourced talent, offshore talent, right? Global talent. And they'll go and they'll say, hey, big, big company, L'Oréal, we'll take care of your Salesforce implementation, you know, and it's all basically offshores, but they're selling 10 to 20 heads at a time. Because these ongoing things. So I think there's so many versions of the business that we could potentially add on that are well beyond 9 figures. But I think the current version of it, which is sort of like this Happy Meal of a handful of good marketing support talent, I think we can rinse and repeat that for a long time.
So we reckon $100 million in 3 years?
You know, I don't— I think it'll take us longer to get there. You know, we I'm— I don't— part of the reason I like to be profitable and closely held is because it lets us make decisions based on what's right for us and the people. Um, and that kind of growth can kill, you know, kills people. And so I don't care if it gets there in 5 years or 8 years, like, who cares? Like, I'm not saying we should— 3 years would be awesome if it's obvious that the growth factors are there and everything's in place, but it's not, and things break. And, you know, and so I'd rather go, let's get there in 10 years. Like, Who cares? But I'd rather do it in a way that's sustainable and inspiring and lets people learn and grow than forcing. There's just no reason to force that level of growth. We have, there's only 2 owners of the company, right? And so it's like, what, for who, for who are we doing that?
My, my final point, which is actually more of an observation, is I don't know why, but from my research of you, I was more thinking that you would be, you'll be like on the marketing side, you know, or on the sales side, which you definitely have strength there. But actually from this conversation, I've learned that you, it seems like you're more like on the operations streamlining, making that side work. Would you agree with that assessment?
I'd like to think of myself as an entrepreneur and a problem solver. There's this concept I talk a lot about called zones of genius. Like operational delivery is not a zone of genius for me. It may be a zone of like excellence, which the distinction there is one gives you energy, And one removes energy, maybe just as good. So I'm good at these podcasts, like I, but I'm, I'm excited right now. Like I feel energy coming towards me by having talking about this. Whereas if I went and talked to a client about scaling their Growth Assistant account, I could probably come up with some cool, smart ways to do it, but it's, it's not going to energize me. It's not going to bring me energy. And so I'd like to think of myself as relatively well-rounded. Um, and I think one of my secret sauces is that I can, I can go from financial statements down to like the action a person is taking. And, and like, I can do that sort of, I have that level of dexterity or whatever you want to call it. And, but I think marketing sales energize me. I think strategy stuff at depth, like our strategy finance P&L stuff energizes me. Organization building energizes me. I think I'm decently good at all, at most of the rest of the stuff, but it doesn't necessarily energize me. Hiring energizes me. Talent energizes me.
Makes total sense. Jesse, we're going to link to GatewayX, the portfolio companies, everything from Bootstrap Giants, including the newsletter. People need to sign up for the newsletter that will be linked Anything else we should link to or mention?
No, I, I appreciate you bringing me on and I hope, hope this is helpful for people listening.
Thank you so much for joining.










