Jesse Pujji of Gateway X - The CEO job is constant evolution - The Michael Girdley Show Episode 38
17 Jun 2022 · 63 min
In this hour‑long interview, host Michael Girdley talks with Jesse Pujji, founder of the Gateway X venture studio and a practicing Sikh, about a wide range of personal and professional topics. They explore how Sikhism blends Eastern mindfulness with Western monotheism, and how that cultural lens informs Jesse’s calm, inclusive leadership style. The conversation then shifts to the mechanics of fast‑growing businesses, with Jesse explaining why companies “break” every 6‑9 months as they transition through distinct size‑based stages, and how CEOs must continuously reinvent their role. They discuss the value of coaching—both business and spiritual—Jesse’s own work with a consciousness‑focused coach, and practical frameworks (the “entrepreneurial loop,” way‑points, and separating accounting from response) that guide his venture‑studio operations. The duo also debate the merit of Twitter follower counts as a vanity metric, share insights from the Inner Game of Tennis on mindset, and reflect on probability‑thinking as a decision‑making tool. Throughout, they weave personal anecdotes about family, mentorship, and the challenges of scaling a portfolio of diverse startups while maintaining a sustainable, purpose‑driven culture.
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Hey, Michael here. Welcome to another episode of The Michael Girdley Show. I spent an hour today talking with my buddy Jesse Pujji out of St. Louis. He does a bunch of cool stuff. He runs a venture studio, which is a business that incubates and creates other businesses, which is near and dear to my heart. We also talked about things like followers on Twitter. Is the number of followers on Twitter a vanity metric? I know that's only interesting to content creators like me, but I found it super interesting. Talked about having to reboot your business every 6 to 9 months. And the coolness of the Sikh religion, of which he is a practitioner and is one of the neatest things that I've run across in recent years. So I really enjoyed talking with Jesse, and I hope you enjoy the episode as much as I enjoyed making it. Here it is. Hey, Michael here. Today's sponsor is Harbor Capital. So Harbor Capital is a firm located up in Austin, and they are a real estate private equity firm that focuses specifically on light industrial assets across the state of Texas. So Levi and his team, I've gotten to know them pretty well having worked with them as an advisor over the past several months and excited to have them sponsor today's episode. So, you know, what they do is basically, you know, acquire these real estate assets using their own money and investor money as well. And then they manage them over time for cash flow and appreciation. Hopefully with everybody winning throughout that process. So they're excited about what's going on, and I've seen what they're doing, and they're also building a portfolio designed to weather both the ups and downs of the economic cycle. So thanks to Levi, thanks to Harbor Capital for sponsoring today's episode and helping me on my never-ending quest to make the Michael Girdley Show a break-even podcast. I'm so excited to do that, and thanks again to those guys. Check them out at HarborCap. .com and here back to the episode. Jesse, thanks for being here to visit with me today. Really excited to talk to you.
Yeah, likewise, Michael.
So, so yeah, you're, you're, I guess maybe a good place to start. We were just talking about it before the, before we click record and maybe I've, maybe, maybe we killed the topic already by talking about it some more, but you're a Sikh American and I was just talking about how I love working with Sikh folks and a lot of it is like And this is— I'm going to try to avoid being totally stereotypical, but at least the ones I've been exposed to, like, there's this level of calmness and peace that I think Sikhs have. So I was just curious to hear your take on that. We could also change the subject if you're like, this is stupid.
But yeah, no, no, I think, look, I definitely, you know, I was born and raised here in the US in St. Louis. And, you know, an interesting story, you know, during I was a senior in high school and 9/11 happened, and I was just like student body president, and I was, you know, as a school and a community leader as a student, obviously. And, you know, as soon as 9/11 happened, there was a massive backlash in the US against brown people, right? And, um, you know, and I don't totally blame anyone. Like, it's— you see the Taliban on TV and they have headgear and they have beards, and like, how do you know the difference, right? It's not like people can know the difference. But immediately, you know, I was called upon by my school administrators and then next thing I know, I'm on the news locally. They're like, well, what is a Sikh? And, you know, like, what's, what's your religion about versus Islam? And not that any, you know, there's no religion that is inherently violent or not, right? Like there's white supremacists, there's whatever, every, but there was an education gap in the US. And so one of the things I remember talking about a lot during that time was Sikhism is a really unique mixture of Eastern and Western ideals. Uh, you know, so West, you know, well, Eastern is more straightforward, right? Let's meditate on, you know, meditate to find God, be very simple, work hard. Like, it's— there's just not a lot of— there's no— you don't have to work through a church, you know, you can just be— meditate, be one. Oneness is the most important thing with God. It's very— sounds very Buddhist when you think about it. On the flip of it, Western, it's a monotheistic religion. Uh, in the 15th century, the founder Guru Nanak said All people are created equal. And you think about India, the caste system, there was like these huge, huge divides between the four people. Men and women were not equal. And here this guy comes along and says everyone's equal, like 300 years before Thomas Jefferson said all men are created equal. Right. And, and there's a whole variety of other things that are very Western in their orientation. And so it was cool because for me, it was— I've always described it as like this perfect mind meld. And it's particularly interesting for me to watch the world in the last 5 or 10 years become mindful and start meditating and kind of going like, I work with a coach who does this paradigm. And I'm like, yeah, like in a fun way. I'm like, wow, this is really— this is the same. I know this, like, this is from my religion. So it's been fun to watch the Western world become more Eastern. But for me, it's always been a— the religion is a perfect mix of the two.
Yeah. So why do you— I love— I mean, everything you just talked about, like, like, I love that there's parts of Christianity that I like. And then there's parts of kind of the Eastern religions that I like a lot. And it was like 50/50 of things that came from both. And you just Like you just described how like, like Sikhism like picks the best half of each and makes a really good religion out of it. So is there anything in like being a Sikh like that is like, okay, there's the other end of the spectrum on being like a mind virus, right? Which is like the LDS stuff, like where they send people out, the Mormons send people out like crazy to recruit. Sure. Like, like, is there anything inherent in being a Sikh like There's— is it— is it—
it's not a very mission. There's not a missionary orientation. There's not a conversion orientation. And then, you know, again, the founder of Sikhism said all religions are different paths to the same light. And so— and actually, like, some of the more extremist Sikhs, which of course there are some, they do— they go, no, we got to, you know, want to fight for our survival and our rights. And but the more the generalness of the religion is, no, actually it's pretty interfaith. You know, one of the— one of the coolest stats I like to give is In the holy book of Sikhism, you walk into the Gurdwara, which is our word for temple. It means Guru's home. And you bow your head to this book, which is the writings of all the Gurus. So they all wrote— we actually have their writings and their, you know, beautiful poetry. But inside that same book we bow our head to is 33 Muslim and Hindu saints who the Gurus said, you know, we're going to be so inclusive, we're actually going to include their writings that everyone has to bow their heads to. And so The religion is just, you know, for better or worse, I guess I would say it has been highly inclusive of other things. And so therefore it hasn't felt the need to, to push people out to go, you know, to drive missionary type thing, type work. There have been some here and there, like there's 10 or 20,000 American-born white Sikhs in New Mexico. And there was someone there who, who led a lot of conversion. But in general, it hasn't been a, a big focus of the religion.
Yeah, I went to a conference for, you know, a big EOS person, which is a business methodology, and then Scaling Up is another one that kind of is the same stuff just in a different format. It's the Verne Harnish stuff. But one of the, one of the like Scaling Up coaches there like came over to start to talk to us, and he's from LA, and he was wearing a turban and he had a beard, and he was definitely like Anglo, right? Caucasian. And so I started talking to him about it, and he's like, yeah, I converted. I was like, oh, that's super cool. But he was a rarity. I don't run across many other people that are like doing that. So super fun. Super fun. So one of the things you tweeted, which I thought was really cool, and I don't think a lot of people understand it, is just around this idea that when businesses are growing and they just, they're growing, that means they're going to break like every 6 to 9 months. And like, I wanted to like probe in that and see, you know, one of the things you said that was really smart was like, this is just like the natural order of stuff for businesses. And I think people don't expect that, like when they're building a company. So anyway, I just wanted to like probe and kind of understand like, why do you think that is?
Yeah, you know, when I talk to entrepreneurs of fast-growing companies who I'm invested in or mentoring or something, you know, the easiest way I can get their mind around this is I go, Hey, let me describe 4 companies to you. One company has 5 employees and, you know, $1 million in revenue. One company has 20 employees and has $5 million in revenue. One company has 100 employees and has, you know, $25 million in revenue. Another has 1,000 employees and $200 million in revenue. And I talk about, you know, each of them individually. Well, the 5-person company, it's easy to talk to everyone, right? And the 20-person company, well, there's probably a couple reporting lines that exist, so on and so forth. And then I go and imagine being all 4 of these companies over the period of 5 to 7 years. And then it clicks for everyone, which is like, oh, these are each, you know, I was, you know, the trick is that's the same company I was describing in name and your title and your position will be the same because you're the CEO of blank. But in fact, it's going to be 4 completely different companies. And, you know, I think people just, there's a natural inertia. Like one of my general philosophies is inertia in business is one of the more, one of the more things you want to be careful about looking out for because inertia sets in with you, with your team, and it's sort of everything's changing all the time externally and you want to be able to move quickly against that change. And so, you know, the idea with that quote is every 6 to 9 months everything's going to break. Well, yeah, of course it is, because you're going from being a 1-person company to a 5-person company to a 20-person company. And a 20 and a 5 are completely different companies. The way they operate is different. The way communication flows is different. The way sales works is different. Just everything is different. And I think that the more, the more challenging part of it is people who overly try to transition and build, you know, one of the other common mistakes I see is, well, how does that scale? Or we have to think about when we're 100 people and it's like, well, no, if you spend all your time thinking about what you're gonna do when you're 100 people, you're never going to make it. You got to focus actually today on being a 5-person company. And so that's just, it's just a really challenging transition. So you can't truly live in the future. And you can't quite live in the present. And, and so my method generally is like, no, just go, go, go, and it's going to break and you're going to fix it. And then it's going to break again and then you're going to fix it. Um, and in fact, like, how do you make that part of the culture? And I think the best organizations, you know, there was a joke at Facebook, the guys at Red Ventures, they're reorganizing their companies every 9 months, right? I mean, McKinsey is an extreme example, moves everybody around every 3 months. Like they're all on new projects. And so I, one of my thoughts of that. I guess, trends I've observed, or is like the best organizations are constantly moving people around and changing things up because they start to actually be, you know, drivers of change, not victims of change.
Yeah. Well, and you can— I mean, the second-order effect of that is you can probably start to avoid kind of the sclerosis that comes into organizations, right? When you— if you're always kind of breaking those things as you're, as you're building it, it keeps from getting kind of that waste and fat and at the end of the high end of the spectrum, the guy with the red stapler in the basement, like you could— yeah, those things don't survive like rapid change.
Totally.
So how do you— I mean, do you think this also applies to the same idea, like when your company is growing quickly, your CEO job is changing all the time? I mean, that was one of the other side of the coin.
I mean, it's being the CEO of— again, like if I told— if I told, you know, Adrian, CEO of Growth Assistant, She's got a staff of 10, you know, yet last year she had a staff of 1 herself. Uh, and next year she'll probably have a staff of 30. And I go, well, a 30, a 30, running a 30-person company is very different than running a 1-person company. Um, and so it's a, it's a, you know, the classic, when you promote someone, one of the classic things you coach them on, or I do at least, is, hey, you know, this is a different job. Like one thing we used to do at Ampush was I'd say, okay, you've been promoted, go home for the weekend. Update your LinkedIn. When you come in, you're, you're not pretend as if you never worked here before. You just joined as the director of growth at Ambush. That, yeah, you worked at some other company. Uh, because the biggest challenge people have when they're transitioning roles, employees, is, is they keep doing their old job or they keep thinking in their old ways and you really want them to think in the new way as if they came in from another organization. And then the number one person who has to do that is the CEO because the job is just so different. Uh, and, and so that would be, you know, I, I find a lot of this stuff to be mindset-oriented and mental, right? Um, you know, and so my coach said something to me the other day. It was like, make sure that every 6 months or every period you're taking ground. It's like a military analogy where you're like, if you, you know, you're shooting, or I assume that, I don't know, you're shooting or whatever, then you run up 100 feet. You can't make the same assumptions about the, the nature of the battlefield at that point. You have to take ground. You have to look around. You have to say, okay, well, it's different. There's a hill over there and there's this. And so I think that's one of the big things I'll tell a lot of leaders and remind myself of, which is take ground. Like when things have changed, you gotta look around, you gotta, you know, there's a different person has to show up every day.
Yeah, I dig it. So one of the things I wanted to, I heard, I just heard you say, I'm curious about, you know, I have a coaching routine that I've too late in life, like installed and hired somebody to like help me kind of break through stuff. I'm, what, what is your? I'm happy to tell you my approach if you didn't read my tweets on it. But what is your structure and like, how do you, how do you get coaching for you personally, if that's what I heard you correctly? You have a business coach working?
Yeah. Yeah. You know, I mean, my journey has been pretty, pretty profound for me and changed me a lot. You know, it just kind of give the story of it. You know, we, we grew Ampush, you know, like crazy, sort of the classic startup, except we were bootstrapped. So it was like doubly hard because we had no balance sheet. Um, and the business went from $3 to $25 million in 3 years back in, you know, 2012 to 2015. And, you know, we sold part of it and sort of, you know, kind of had what I was, I was thinking I was right around 30 or a little bit under 30 and kind of, we'd had that success that every entrepreneur wants. And, and I had this period in 2017 for 6 months where I like didn't want to go to work. And I just felt really unmotivated and I was like, oh, why did I, you know, this business is like, who cares about marketing and ads? Like. This is so stupid. Like, I just remember this very, very vivid period of my wife was just like, I've never seen you like, you know, you're, you're waking up, you're not wanting to go to the office, you're canceling your meetings in the morning. And I was talking to Rick, the founder of Red Ventures, who's a mentor of mine, you know, and his actual response was in a very loving way. He's like, he's like, you know, I was like, I'm in a rut. I don't want to, you know, what am I doing? And he's like, You know, Jesse, you're one of the luckiest MFers I know. You know, you have two healthy children, you've made tons of money, you're CEO, you're in charge of what you do. And so he encouraged me, he's like, you know, clearly this is not an outward issue, this is an inward issue, there's some inner work to be done here. And so he encouraged me, he's like, go find a coach. And so I met, you know, this guy, Dave Kashin, who's my coach, he's been my coach for 5 years now. And his, you know, like, it was a pretty mind-blowing experience for me. And I don't, I did not grow up in a highly empathetic household. I didn't, I didn't grow up thinking about emotions and feelings. I didn't really grow up thinking a lot about how I was feeling. Uh, and he sort of introduced like, oh, what motivates you, Jesse? You're super, you've been super fear motivated your whole life. Now you've had that, you know, you've sort of, you did the thing you were afraid you wouldn't do, and now you don't know what to do with yourself. You're sort of, you know, you're, that's why you're in neutral. And so that kind of led to this whole series of inner work, thinking about questions. Okay, well, what does motivate me beyond money, beyond success? Like, what are other things that get me really excited? And so there's this whole sort of— and we can go into more into it, but it was this whole unpacking of myself, which has been really awesome and really amazing. And then, you know, beyond that, there's a bunch of small things here and there, like having clear agreements, you know, like who does what by when. And like, that like has definitely affected work, but even more it's affected my life at home and my marriage, right? Like, my wife and I realized 80, 90% of the things we would bicker about or fight about was because we just hadn't made a clear agreement. We hadn't said dinner, you know, she would have said, I want to leave the house at 8 o'clock for dinner. Like one time I remember this funny story, like I was in the middle of my coaching, like, so I'd kind of been introduced to stuff. I came home and she's like, the babysitter's coming at 8. And I'm like, cool. And, and the dinner reservation's at 8:30. Right, or something like that. I don't remember what it was, but I'm like, cool. So I get home, it's like 7:30. I want to play with my son, you know, like playing with him, getting, putting him to bed. And it's like 8 o'clock, 8:05. She's like, hey, the babysitter's here. I'm like, okay, cool. And, you know, whatever, say 8:15. And I like help him put him to bed. And then I like want to knock on the car. She's already waiting in the car. And I'm like, okay, cool. And like pulling out and she's just like steaming mad at me. And she's like, I'm super hungry. Like, what, you know, what's going on? And I was like, I don't know. She's like, I told you, Baser's coming at 8. I'm like, I'm like, oh, that meant you wanted to leave at 8. I was like, oh, oh, I had no idea. Like, I really genuinely had no idea that's what you meant. Um, and so both of us have gotten really good at trying to be really clear and precise and specific with each other. And it's like, we've been such a— it's like such a small thing, but such a game changer in a marriage.
So it sounds like your, your coaching is more life coach and less business coach. Is that, is that how, is that accurate?
No, I mean, well, maybe it's evolved in that way. Like we, we thought of like there was a 2x2 in our minds when we picked a coach, you know, on one hand is like business consultant. And on the other hand is like spiritual coach. And then the other one was like, has this person been an entrepreneur and CEO before? Are they like a professional coach? And we wanted someone who was like, probably like in the middle of spiritual and business. And I think it started more to the right of more business, like slightly more business, and then it's evolved more spiritual. And then, but someone who had been an entrepreneur before. So, but his, you know, this, he uses the Conscious Leadership Group as the paradigm. You were mentioning EOS. It's another, you know, one of these other paradigms. And, but a lot of it is when you're running into a challenge or problem with a person or situation, It's not, they don't necessarily offer a, here's what you should, here's the playbook you should run. Instead, it's like a reflect on yourself. What, you know, what's holding you back? What's, and so it's a little bit more almost like using personal life coachy stuff to attack business problems. Maybe how I'd describe it. Dig it.
Okay. Do you think you'd ever wanna do that job? Like, here's, here's why I ask.
Yeah.
Like, like there's some elements of coaching I like and I do it all the time, like in, in what I do every day. But at the same time, like, I only find it rewarding when I have like somebody who's inspiring to work with, like on the coachee side, and I have skin in the game. Otherwise, like, I'm just totally not interested whatsoever. And, you know, I work with my business coach, and numerous times I'll tell them like, how do you do this? Like, I'll ask her like, how do you do this? Like, you just spent 7 hours today listening to people like me whine about stuff. Like, it just seems not interesting. So I was just curious.
Yeah.
You know, so it's one of those things where it's in the bucket of the quadrant of things that I think I'd be pretty darn good at, but like, I think I would be really unhappy doing it. So just curious if you—
I would love to get the training. Like I want to go to Landmark or go to the various coaching. I forget the other one that everyone kind of starts their coaching journey on because I just think the skills of listening and empathy and like all those things are the same of great leaders. And I think all the best leaders have been coaches, um, in their own way. But I would find it tough to get that involved in other people's problems, but not that involved. Like, there's this unique thing a coach has to do, which is like they're really present and there for you in that moment. But at the end of the day, they actually— it doesn't affect them at all other than the fact they want to help you. And I'm not sure I'm quite built that way. Uh, but if I had skin in the game, or like, as I think about building GatewayX, I am trying to establish almost a semi-coaching relationship with each of the, each of the leaders.
Like, I'm with you. Like, well, and I think that's one of the things I'm excited to talk to you about is like, you're doing a venture studio to some extent. I'm doing a venture studio. Like, I'm with you. Like, that's what I do like all day long. Like with the CEOs I'm working, like I'm, people are like, well, you operate all these companies. I was like, actually I don't. I just help the people that are doing it. And that's the only scalable kind of way to go about it. But I can do that with skin in the game when it's just some random thing where either I'm frustrated, you know, frustrated with the person or I don't. The other thing I found I really need is just that, like my business coach calls it, like the 0.1%. Like I got off of all boards where I was just like 5 or 10%, just like, or I was just like on a nonprofit board where I had no skin in the game because he's at one point like he had me sit down and list all the stuff I was happiest with and all the stuff that I was least happiest with. And he's like, look, look at all the stuff you're least happiest with. Like it's the stuff where you don't have like the 0.1%. Ability to make like real change when you want it to. And I was like, oh, that's a really good insight. Thank you for being my business coach.
Yeah, it's amazing how those little things can really, really change. You know, that's like, that's where you're like, wow, like how this seems so straightforward and easy, but you asked the right question at the right time and gave me the right exercise in that moment. And it, you know, like it made my head explode.
What they've done, you know, when I started an educational company, like I spent a lot of time reading up on like what makes good teachers, what makes good students, what makes good tutors. And one of the interesting things that I found when I was reading about great tutors was they discovered like the value of like a really good tutor can be worth like several grades of progression for a kid. And they went in and tried to figure out why certain tutors were better or certain teachers were better than others. And they realized that, you know, okay, so if you think about the spectrum of people that are teachers or tutors, you have the bottom third who are just stupid. They're going to give you the wrong answers and they're are just unhelpful. Then you have kind of the middle, like 60%, you know, one standard deviation on either side. And those people are like very good at, they can give you right answers, right? And they're okay tutors. The magical tutors knew not only what the right answer was, but like what was the precise right thing to tell you next in terms of helping you kind of unlock your understanding. Um, so anyway, that's, that's what I think like sets apart like the magical coaches. Like you don't even really know they're doing it because they're just kind of feeding you the right thing in the right way, um, to where you probably think it's your own idea to change your mind, which is helpful for somebody stubborn. Stubborn like me.
I don't know if you're a sports guy, but I play tennis pretty competitively. I played growing up and then I like took an 18-year hiatus and started playing again during COVID And you know, when you're coming back and the rust, you're rusty, it's really frustrating. You know, it's just like, cause you knew how to play once and, and I had this coach, I'm like trying to hit serves and they're getting, you know, going all over the place. I keep hitting, you know, framing them. And he goes, when you, when you look at the ball, I want you to figure out which way it's spinning. Or I want you to look at the seam of the ball. Or I want you to look for the word pen to try to find what number the ball is when it's coming at you. And I like, I kid you not, I mean, within 15 minutes, he— I'm like the old Jesse's back, like I'm crushing it. And I was like, you know, like, what's going on? And, you know, here I am thinking there's some trick to what he's telling. He goes, He goes, it's just a trick to get your hand-eye coordination back on track. Like, if I tell you look at the ball, you're going to look at the ball. If I tell you to look for something deeper into the ball, you're actually going to— you really have to stare at the ball. And that actually just makes you better at all your hand-eye coordination. This is a great—
have you read a book called— have you read a book called The Inner Game of Tennis? Yeah, yeah.
I actually do what he says, like, bounce, hit. Like, I— it's a great— I mean, yeah, tennis has been a phenomenal sort of reminder again of something, of being mindful. And like, it's just, that is the game that is, you know, the mindfuck of all mindfucks.
Like, it—
every minute you perform and then you have to think about it, then you perform, then you have to think about it, you perform, you have to think about it. And it just really, it captures your brain in a unique way. And it's actually helped me had a real clear sense for when my ego is taking on and when, when it's like not my ego. And like, my ego really cares about the score. My ego's always thinking about 3 games ahead, my egos and the, like the non-ego is like, okay, I actually have to move around the court and hit the ball during this point. And so like, I've actually developed a method where I, when I'm, when I'm playing tennis in between the points, when I noticed that, you know, like a lot of the conscious leadership stuff is like, don't fight your ego. Just actually embrace it to say, oh, like, oh, my ego. Yeah. That it just loves thinking about scores and it loves to win. And it loves to be, you know, tell people. You know, sometimes when I'm losing in tennis, I will literally have the thought of, what am I going to tell people about this match? What am I going to tell my wife when I get home? And it's like my ego wants to— okay, I'm going to come up with a defense mechanism. You know, I was tired today, I had a long day at work. I'm already planning what I'm going to say when I lose the match. And that's just ego, right? It's like ego trying to protect. And so it's been really actually very helpful for me to delineate. And the same in business. Now I start noticing, like, when I think about vanity, but, you know, valuations, when I think about how much, like That's clearly when I actually am like running a really good meeting or doing a really good sales call, like that's me on the, on the court playing. And so learning to differentiate or notice those things has been really powerful for me.
Yeah. Well, and it's, uh, the other thing, the other thing that's cool about that, I mean, it's the whole Inner Game of Tennis book. If somebody hasn't read that, it's not actually about tennis. It's about how to like, you control your mind and mindset, which you're talking about, which is awesome. But the cool, one of the coolest things is like, like for me, like for example, if I go in now and I was to like interview for a job, like I know all the tricks. So like I would be a terrible interviewee because like I know what tricks they're using. I mean, the same thing with like a coach. Like it's cool. It was cool to hear you say like, oh, like the coach said, just pay attention to the writing on the, on the ball. He's doing it. You know, it's an inner game of tennis trick on you to make you quiet your monkey mind and just, just focus on the moment. And let your second mind, kind of the one that gets shit done, like focus on doing it. And like, it's so cool. I mean, for me, when somebody does that to me now, I'm like, okay, thanks. Thanks. Yeah, I know what trick you're doing. We'll do that trick. It sounds great. And so anyway, I don't know if there was a point to that comment, but it's— I'll see my business coach do it to me too, where he's like, okay, well, what about this? And I'm like, oh, I know what you're doing to me. This is going to work great. Okay, let's do it. You know? And maybe that's a sign of just actually buying in and being coachable. Yeah.
Yeah, for sure. Yeah. I think, well, even if I know the exercise and I've done it before, it's just like, you know, repetition doesn't spoil the prayer, you know? Yes. I've served the ball a million times, but spending 20 minutes serving or even literally 6 minutes before a match, I will get 1 or 2 more games. Like I will, I'll be that much better on the court. So any of these exercises, whether you know what's behind them or not, I find them to be extremely valuable.
Yeah, totally dig it. Well, and I think this— I'm inspired because I keep getting coached by my coach to become a better coach. That was like the most recursive statement ever. So maybe I should go to one of these coaching training things. You said Landmark is one of them, and then there's—
yeah, I forget the name of the other one, but I looked at it closely and then COVID happened and it sort of— they all—
yeah, but it's kind of, um, I assume they all have kind of the same 10 or 12 ideas and techniques. I would guess that, yeah.
I mean, look, I think the big things I'm sure you struggle with, I struggle like, you know, one of the biggest things a coach has to learn is like more empathy, more, more sort of reflecting things back to people versus solving pro— like you're not there to solve the problem. And I'm guessing you and I, you know, I certainly, that's my hardest challenge. Someone brings something to me and I'm like, okay, do this, do this, do this. Okay, go. Like, you know, and that's not— a coach actually goes, well, uh, what do you think you should do? You know, how, how, how? And how would you approach it? And why is that? Oh yeah, I see. I see that frustrating thing you're dealing with. Like, there's a thing about it that feels a little foreign for me at least, which I'd like to get more practice at.
I think it's, you know, I'm 47 now. I think it's easier for me now than it was as a younger man. Like, I always had to be like the smartest guy in the room. And, you know, maybe it's just getting older and being more comfortable in my skin now. But like, yeah, my default answer to anything is like, wow, that sounds horrible. What are you going to do about it? That's like, that makes you a much better, much better coach. And also like just the pain of, you know, I've seen when you go in and like, in my role, like insert myself in the operation of the organization, like it never comes out right. Like, and the times it does, the only times it does, does come out right is if there's like very specific, like, guidelines of how I'm coming in and leaving, right? And it's like, okay, you're doing this, this is my area. And then I have to have like a very tight like mindset where if somebody's like, hey, let me drag you into this other thing, I'm like, no, no, that's outside of this work statement. Like I'm just doing this, this one thing. Otherwise, chairman of the board is going back to the hole where he came from.
So yeah, that's good. Rick has a saying where he says you have to learn when to inject and how to eject.
Yeah, well, I don't know if you saw it yesterday on Twitter. There was a— somebody passed around this letter where Warren Buffett like went and gave like a long feedback thing to the president of SEAS and Candy and this guy Honam, who's like super smart VC, as you know, like gave a whole screed about how you can't do that. I was like, oh, like you can't. You have to be so careful because Like one of the things I've learned, like, so one of the companies I incubated started, you know, there were 3 of us co-founders and really 2 co-founders at the beginning. A third one came in 6 months later, but like that's gone from 3 people to like 300 in 3 years. And like one of the things that I had to learn was at a certain point, like I can't go to— there's certain meetings I just can't go to and I shouldn't go to, you know, At your best cases, there might be two CEOs in the room because like I have strong opinions on stuff. Worst case is people take something I say offhand, misinterpret it, and go run off and do something with the company they shouldn't, maybe contradictory to what the CEO wants. So like I totally understood what Honam was talking about. Like you can't— you got to be super careful about how you inject yourself. Like that's—
that's one thing. And I want to read that letter. I didn't see that go around. And I love— I think Honam is awesome. And I think like, you know, there's no right, like one of the things that I'm, as I see, and I'm sure you see this too, is like, you know, the nuance and the devils in the details of all these situations and meeting people where they are and meeting organizations where they are. And so I think really to me, it's much more about like, can you see reality clearly and can you calibrate appropriately to it? And sometimes, you know, your strong opinions are really important in that moment to give and to. And to be able to like actually be very clear about what you think is the right thing. And other times you really want to let— leave it alone. And there's just, you know, uh, yeah, there's no— I, I just can't imagine a broad rule of, okay, well, never, you know, if you're— because obviously even Warren Buffett is famously hands-off, you know, he's not actually famous, he's not hands-off, he owns these companies and I'm sure he talks to the CEOs. I'm sure, and I'm sure some CEOs he gives more feedback to and some he gives less and He has replaced the CEO. It's like, it's not— and that's something I've been trying to really actually for myself, because I have certain dogma about bootstrapping or certain dogma about— and I've been like, well, hold on, I don't want any dogma. I want to look at each situation for what it is, apply a thoughtful business lens to it, and then, you know, and then go from there and make good decisions.
Well, I think so. The lens I used to kind of think about that is everybody expects, uh, business or things in life to operate like a chemistry experiment, right? Like if I put If I put electricity into water, guess what comes out? Like hydrogen atoms and oxygen atoms. Like, that's a chemistry experiment. It works that way. But like, everybody expects business to work that way, but it's actually the exact opposite where everything is like an exercise in probability, like hiring people, making business decisions, making a strategic decision, saying one thing versus another. Like, and when I kind of internalized that, like, it gave me so much more peace in terms of how I go about stuff. Because, yeah, it's because I understand like, oh, this has an 80% probability of success. So like, like, understand what you're doing and it's everything's just a miniature bet and they just scale up from there. So yeah, it's funny.
I've like gone out of my way with my kids to start to basically not to start since they were born, you know, when they ask me things, never speak in certainties. And so like my son, you know, one day he was like lying down on his bed and he looks up, he looks up at the ceiling, goes, what's that little plastic thing up there? I go, that's a fire alarm. Smoke alarm or whatever. He goes, okay, what's that? Like, I go, well, sometimes houses burn, you know, like a fire starts. And he's like 5 years old, right? And he's like, and that alarm lets us know and it lets the fire department know to avoid it. And of course he freaks out. He's like, what? Like, houses burn? And, you know, for the next month he's like, is the house going to burn down today, Dad? Like, what's going on with this? And I made it a personal line not to say no. I said, there's an extremely low chance, like, like it's, you know, it's very unlikely and here's what that means. And like, now he's a little bit old, he's almost 7. And so he understands the basic percentages and stuff. And, but like, so now you're like, oh, well, well tell me, is it, is that 60% likely? Is it 90% likely? Is it, but like kind of just got out of this thing of like, I don't ever want them to think in certainties, cuz there really is no, no such thing as a certainty. And actually once you get comfort with probabilities, it's a, it's a whole unique advantage and edge you can develop.
Yeah, totally dig it. I did learn last week, actually, water will set off fire alarms too. We had a leak in our house and all the fire alarms were going off. And my kids were awesome. They— I was down at the bike shop and my kids are 16 and 12. So I get back home and the fire, you know, I came back immediately and the fire alarm's still going off. And evidently they had decided to evacuate our cats. Out of the house. So I get back and they're both sitting in the driveway in the car, and the cats are just scared, you know, scared to death, sitting in the back of this car like, what is going on? But yeah, they, uh, they did the best they, they knew how at the time, which was, okay, well, get— let's get the most important things out of here, the cats. I was like, what if I had like the passports and family photos? You guys didn't care about that?
No, no, we were living people, living, living things.
Yeah. So one thing I wanted to probe on you, because I'm starting— I've been— let me give you some context, like So earlier this year I started like at 40,000 Twitter followers or whatever, and then I was like, you know what, I'm gonna get it to 150,000. And that was, that's been my goal for the year. And I wanted to probe this with you cuz I know you've gone through this journey, so I'm trying to figure out like, is that a stupid goal or not? And this is like the most Girdley thing ever to do, which is to get halfway through something and then just decide it's not important anymore. So, but anyway, like, you know, so I'm pushing 100,000, like I'm playing the thread game, like. Doing all the things you're supposed to do to get more followers. And it's like, I saw you go through that journey, like you were trying to push to get to 100,000 last fall. And then as I look at your tweets now, like it's not as important to you, or seemingly not important. So you can, and you're at 137 or whatever, but you know, I'm curious, like what has your journey been with kind of that metric? Do you think it's a vanity metric? Do you think it's a worthy goal? Like how do you think about it in the context of Twitter?
I think like all goals, it's sort of like why, what's behind it is sort of where I would go. You know, in my case, I sort of— the spiritual side of it was like one of my— one of the things I realized motivates me endlessly beyond money and all this stuff is I love to coach, teach, inspire others via entrepreneurship. Like, I think entrepreneurship is this amazing— it's like running a marathon where like, you're gonna grow a lot as a person in doing that hard task. And so that to me was like the heart of it. And then the more like, transactional aspects of it were like, hey, it'll bring commercial opportunities, it'll bring me talent and recruiting, um, and it'll bring me some investment stuff, you know, stuff that actually is going to be real. And I'd say on those three, by the way, it's blown me away. Like, it's way surpassed any expectations I've had. So I think, like, in my case, I think it's, it's absolutely— people encourage me to do it, and I thought, you know, gosh, this is— what do I do? How do I start this? I think it's certainly worthwhile and worthy, um, and something that I think is worth pursuing for a variety of different reasons. Like, there is impact. You can you can have and, and benefits that come from it. Um, you know, it's funny you say like most of my stuff is just because I'm like, I've gotten so busy that I've had trouble, like, like the grind to get there. Well, there was a period where I was like, okay, I gotta write 2 threads a week and I'm gonna, you know, and I did that. And then I got past 100. And the one thing that happens past 100 is there's clearly some social proof on Twitter where you're like, people just follow you more because they go, well, you know, 100,000 people follow this guy, he must, he must be worth following. So that it becomes the growth becomes a little easier actually is what I've noticed. But then, you know, the other thing I realized was like, I'm, and I guess this sort of, there's all these arguments about this, but like when I write the best threads I've ever written were ones I wasn't planning on writing that I was just like, oh my God, the, like, you know, the spirit has caught me. I need, I need to write this on my phone. And those have been the ones that have gone the most viral that have led to the most followers that have gotten me the most inter— you know? And so. I think there's a chicken and egg there a little bit. I do think, you know, writing relatively frequently is important, but there was this weird grind I got into, which I just stopped enjoying, to your previous thing. And I haven't quite figured out the system yet of like, I do want to consistently put out more interesting threads and stuff, but trying to figure out how to do that with all these different things I have going on and being able to scale that out. So, but, but I think it's worth it. And I think, um, if nothing else, man, I'm sure you've gotten these too, but like every time I write a decently good thread about delegating or something that's interesting, I probably get like 20 to 100 messages being like, thank you, you really unstuck me on this thing. And like, that alone is like better than, you know, leads to Growth Assistant or 5 other things that commercially are valuable for me. And some of them, like I wrote this one about the upper limit problem. I mean, I've gotten on calls with people who go, you wouldn't, you wouldn't believe this, but you wrote that thread and like, it changed my life. Like, you know, it led me down this path and X, Y, and Z happened. You're like, wow, this is, You know, the power of media is real. Uh, and so yeah, I think it's worth it. I think you should keep going.
Yeah. I mean, and I thank you for the encouragement. I'm not, I'm not planning on quitting cuz I also like the fear of being like, I don't wanna be the person who like quits stuff just because I feel like it. Um, so that's greater than like my, any sort of intellectual objectivity to it. Um, but I was just curious to hear your, your thoughts on it. It has been surprising. How well there's— I guess it's unsurprising how many people take, you know, somebody who's producing content on Twitter and being out there as a license to like ask you for stuff. Like, so that's not surprising. I get— and I feel bad about it. Like, there's just so many people that are like, hey, come do this for me. And I'm like, I can't. Like, it's just too much. But I have been, as you said, really surprised by the number of people that are just like so grateful. Like, they just say, I just want to say thank you. You don't even need to respond. Like, that surprises me a ton. Like, I would not have expected that. Nobody like sends a thank you note, you know, historically to the editor of the newspaper when they liked one of the articles.
Like, so yeah, it's incredibly touching and encouraging. And I think, and it's a good reminder of like, you know, whatever, we're on our own journeys individually and as people, but like, we've learned some stuff, you know, I've learned some stuff. And when I put it out there, this thing, you know, even though I didn't at the beginning, I started, I was like, have I learned some stuff? Am I, you know, I'm not I'm not a multi-millionaire. It's like, no, I've learned some stuff and that other people can benefit from that. So yeah, I like—
Yeah. So a funny story about that. I think I was closer in your age. You're like close to 40, I guess.
I'll be 38 next week. Yeah.
38. Okay. So I was right around the same age and I wanted to get involved in the startup community here in San Antonio. So I went down and started hanging out at the Techstars program that we had here in San Antonio. The city at the time. And, you know, I was talking to the MD who was, you know, a little, little, little younger than me, but about the same age. And, and I was like, man, like, I don't know if I could be a mentor for this. Like, I just don't know, you know, I don't know anything about this stuff. He takes me aside, he goes, Girdley. Yeah, I think I was 36 at the time. And he goes, Girdley, you don't know what you know. Just go have a couple conversations with these people. It'll blow your mind. And I was like, okay. And I went in there and like talked to them. And they're like, so like, like, how do I fire somebody? And I was like, what? Like, this is the You know, do I need a corporation for this? And I was like, what? Like, this is the level of like discourse. So, you know, over time, exactly what you're saying, like in business, you just build up so many reps that you don't, you don't know what you know. It's just incredible. So I did want to talk to you about like, so you're doing a venture studio. In fact, I'm doing a venture studio, you know, unlike, say, running a legal practice or an accounting firm, there's no like, okay, here's how you organize all this stuff, or like, here's how it works. And I was just curious, like, you know, what is your journey to like get into doing a venture studio? And then like, how do you think about like what's been working well so far and like what's not been working well?
Yeah, yeah. What a great question. Good opportunity for me to reflect too. You know, my journey towards it was very much rooted in coaching and, you know, it became clear to me that one time my coach asked me, it was kind of a— it's a good question. Led to a profound answer, which was like, one of his theories is like, you know, we talk a lot about purpose and it becomes this other brass ring. We, oh, I need to go get purpose and I need to get my passion. And I was in that same zone of like, I can't find it. Where is it? You know? And his theory is it's already, it's already something you do. It's so inherent to who you are, but you probably haven't spotted it yet. And so he asked me this question, which is, what's the one thing you can't not do? You know, if you bring it into a room with you, it's a smell, you know, every, every podcast, every tweet has a piece of it in you. What's— what is that thing, Jesse? And I sort of said it was like to help people raise the bar and like level themselves up. And I use entrepreneurship as a canvas to do it. And you could use, you know, sports to be the canvas. Like there's a million ways to get better, to improve yourself. And I happen to use entrepreneurship. That's the one I love. And I was like, so I was like, well, if I wanted to do that in an extreme way, what is the organization that would support that best? And I had thought about, you know, could I do that? I could do that as a VC, probably. I could do that as, you know, continuing to run AMPush in that way. But, but it really began— I was like, man, I think the venture studio model where you're truly spending your time launching businesses, coaching people to build them, like it's just a huge opportunity to grow, grow others and grow yourself and be able to scale that. So that's kind of where it came from, sort of spiritually. But then, and then commercially, like I have a lot of ideas and I know a lot of people and, you know, I always talk about I have a couple unfair advantages that are pretty pronounced. One is I know how to do digital customer acquisition really well. And I've like forgotten about more stuff than most people have ever known about customer acquisition. And then on the sales and marketing side, I know how to sell stuff to brands and marketers. And so, so the businesses we launch have to fall into one of those two categories or both in terms of what the topical area is of them. Um, so anyway, that's kind of what the genesis of Gateway is. And then the other thing is I moved back to St. Louis from the Bay after 10 years. My wife's from here. We want to raise our kids here. And I was like, I want to do something cool for this city. That I hold in such a high regard and I have a high affection for, what would be a cool thing I could bring to the city? I was like, I could launch businesses and that would be a really, really awesome thing. And so what have I done well and what have— what has not gone as well? What a great question. I think what I've done well is I think I've like, after running a company of, you know, close to 200 people for 8, 9 years, I think I got back into kind of entrepreneurship gear. It took me a few months because I was used to like having, you know, CEO and an office manager and assistant and people to do work. And it took me a few months, but then I got back to like, no, wait, if you want to get something done, like I can launch a Wix website in a day. Like I got back to the kind of like just move really fast and get stuff done. And so we've been able to do that and really, you know, that ethos has become very real and we've been able to make progress on a lot of fronts in a very short period of time. So that's a good thing we've done. I think a thing that has not been as well related to that is like, if I could do it all over again, I wouldn't have launched 3 things in the first year. And everyone told me not to and I was like, I can do it, whatever. And so I think I probably would have launched 1, maybe 2, but like 3 was just too much, including all the Twitter. Like there was too many things I was trying to do in 1 year and Um, I think it's a combination of like, I didn't quite— I don't feel like I've quite brought my best to each situation. And I feel like it wasn't a major issue, it was like by 20% though. Like if I could have reined it in down by 20-25%. And I think the other thing is like, I— part of what I'm trying to do for myself as well as for the people who work at GatewayX is like, I want to create something sustainable. And to me, sustainability, it's not just work-life balance, it's also like thinking about and doing a certain number of things at a time in sequence order versus parallel order so that you can, you can, we can do this for 10 years or 20 years or 30 years, right? We can launch, I don't know, 20 companies in the next 10 years if this all works. So in some ways there was no reason to rush, but like I was excited and I just wanted to get after it. But I think it would have been, we could have been further along in the thing, you know, in 2 of the things instead of 3. Uh, and it would have felt better. Like it felt a little, little much. So that's something I would have done differently. What else has gone well? Like, I'm happy that we've launched things in different areas. Like they're not all the same kind of business, which I think has just been really diverse around them. I think I would have capitalized them slightly differently in the way that I've approached them. Just, just in the sense of like we've kind of kept it as one big balance sheet. And at first I thought that's what I wanted to do. And again, this whole thing of dogma of like, and now I kind of feel like it'd be better and smarter to keep them individual. And I'm playing around with that a little bit. That's not a one-way door. You can, you can change that. So that's another thing. So does that mean it's not, not a one-way, like, like I can raise money in individual companies as opposed to keeping them as one big thing, which is sort of where it's—
oh, okay.
Um, yeah. And make them individually capitalized.
So that's where you've ended up or that's where you—
well, I think what's going to end up is I'm not going to— it's going to be kind of both in the sense that I think some of the like Kahani, which is the SaaS business, like that one seems like it needs its own money to grow and scale itself and it's a big opportunity. And so the other one, like, you know, the Growth System, Unbloat, don't— they seem like they don't need that individually. Growth System is already profitable. Unbloat, I think we can get it to profitability. So I think Some of it is just not being dogmatic about one approach, but saying, what does the business need and what's the right thing for it? And then capitalizing it based on that versus trying to kind of be this master capital allocator. Um, what other, what are some other specific learnings? I think it took me a little bit of time to kind of set up clear structures and agreements with each of the leaders and kind of orient myself to meet them where they were. So for a minute I was trying to do it, okay, everyone's the same. And like, that doesn't work. Some people are further along in some dimensions and some And so it took me, you know, more time there than I would've probably liked in retrospect.
And then, you know, how are you thinking about what your kind of repeatable process is for kind of taking stuff from research to inspiration to, you know, either spinning it out or not, like through that whole process? Like, do you feel like you've figured out a repeatable process at this point and structure for everything, or are you still? Kind of figuring it out. By the way, I'm asking because I'm in the 'I haven't figured this out' bucket. Like, well, here, I'm going to hire some associates. This will be great. Like, that's the—
yeah, I don't think I have. And I'm not sure that I— I'm not sure that I want to, you know, I don't think I have. And I'm not sure that you should, I guess, is what I might say. Like, I do have a high-level process that I put together when I was at Ampush with my co-founder there that I call the entrepreneurial loop. It's pretty wide and it's like our version of OKRs almost. So it's like you put together a desired future state, you know, and it's, it's sort of what do you want in the future? You know, then you kind of put together where you are today and you sort of make sure that the stretch is reasonable. Like it's not too much, it's not too little. Then you put together kind of like, there's this concept of waypoints, which we really like, which is, it's a sailing analogy. So, you know, apparently I didn't, I don't know how to sail, but apparently if you were to sail from. San Francisco to India, you don't just do it in a straight line. You first kind of, based on the water and a bunch of other things, factors, you first go here, then you go here, then you go here. So we spent a lot of time, okay, what's the next most important thing we need to get going? Okay. Well, like we can't, we can't, for example, for Unbloat, it's like we couldn't spend more money on other channels until we solve conversion rate. And so it's really kind of gating, you know, whatever you want to call them, like stage gating or like a video game. It's like levels. But we're really big on kind of figuring that, that of those out. Um, and then from there, there's a lot of kind of like iteration. And then the other big thing we try to do with everything, which is really hard, is we call it accounting and response, but it's really separating kind of like the facts of what happened versus like how you want to respond to them. And typically what happens in organizations is someone shows up to a meeting and maybe their dashboard's red, yellow, green, and they already have a narrative prepped for each one. Well, here, here's the thing that happened with this and, and here's why this one is behind where we'd like it to be. And what we try to do, not in a positive or negative way, it's just unemotional. It's like, where do we think we would be?
Where are we?
What's, what's the reality? And just, I don't want it like, it is a 10-minute process, but it's like, don't, I don't wanna hear any spin. I don't wanna hear any narrative. I don't wanna hear any plans. I literally just wanna go, what's the reality? Oh, we're behind this. You know, we, we're not getting as many sales meetings as we expected. Okay. This is. Okay, cool. Like when that's all done, you go, okay, so what should we do about it? And I think part of the reason is it's, again, it's avoiding inertia of you actually wanna pause and sometimes you wanna kill the initiative. Sometimes the right thing to do is you're behind on it. There's too much red here. Let's just, we clearly have learned that we can't take on this many things. Let's kill them. Right. So, so there's a, there's a process of trying to disconnect the accounting and the way you respond to it a little bit that we, we spend a lot of time on and then it kind of feeds back into it. Itself. So then you're like, okay, now what do we want? And so on and so forth. But I don't know, I think anything too structured runs the dogma risk. Yeah.
And then do you think— I mean, it sounds very EOS-like. I mean, that's kind of the same process, you know. I run EOS, like, for everything, me on down.
I'm not super familiar with EOS, but it wouldn't surprise me. I mean, there's not— there's not— there's only so many ways, you know. There's only so many ways you can worship God, right? Like, yeah, it's like every religion. Okay, be a good person, you know, God loves you, repent for your sins. Like every religion kind of says the same stuff, right?
Yeah. And then there's the polytheists that are over here somewhere doing some weird stuff. But yes, the Wiccans. But yeah, it's kind of the same, same stuff, right? Like you pick a vision of where you want to be, you set intermediate waypoints of where you want to be, all the way down to what's happening this quarter and this week. And then you readjust as makes appropriate. And like you said, initiatives, you can only have a limited number of those based around things you're trying to achieve. And then you have metrics for the business, all that kind of stuff. So it sounds like not that far off, but the same kind of concepts tend to be there as to what I just heard from you. And maybe that was just confirmation bias. I don't know.
No, no, I think— I mean, we always tell people like it's a version of our version of OKRs. Like the way I've seen it, it's the same kind of stuff. I think the big challenge with OKRs is they assume a certain sense of false certainty. That most businesses don't actually have, right?
OKRs are hilarious, mostly because my exposure to them has been reading the John Doerr book, who, by the way, he doesn't run OKRs for their fund. It's like, okay, well, that's kind of one thing that should be a telling thing. We, you know, we're— we run Kleiner Perkins, but we don't— we don't use OKRs. Let me tell you how Google did it. I was like, well, I read the book and I was like, well, you know, Google is the greatest business, the second greatest business in the history of mankind behind Apple. Like you could put anything in there, it's going to be great. Like, you know, who cares? So anyway, that's the— my problem with OKRs is it seems very California-centric where everybody's got to have their own way of doing stuff. And like, I just gravitate so much more to a hierarchical kind of thing where it's like, we're going this direction, get on the bus or not. That's fine if you're not on it, like, but we're going this way. And OKRs, like, as I read it, I was like, this is anarchy. Like, I don't understand. I don't understand where this is going. And I like what you've done as a spin on it, which is like, say, okay, we're going this direction and this is how we're going to get here. And these are the initiatives and we're going to revisit these over time. So super cool. I totally agree with you. So what do you have all these people in St. Louis in the office or how's that? How's that?
Roughly 50/50. You know, obviously in this day and age, it's pretty hard to to say you must move to St. Louis, Missouri, right? So we have, I'd say again, half are here, half are distributed. I do like part of this for me of just the fun of it is to have a talent center and an energy in an office and young, you know, young, smart people growing and figuring things out. So I do, I do have that intention. I think I'm being pretty flexible about how it's going to work. One thing we've had a fair bit of success with is like everyone either come here for your first 3 to 6 months if you're not, you know, you don't have whatever, if you're young, yeah, or, or come and spend a week, a month or something. So we are trying to create a lot of in-person time, um, and that's, that's a big part of, of what we're doing.
And what is your, what is your limiting factor for growth at this point? I'm guessing it's not ideas.
It's not. I mean, if anything, ideas are probably— we're purposely putting a bunch of stuff on hold because we want to give these things, you know, the 3 things we've got going enough time to, to work. Um, they're each different. I mean, I, you know, uh, growth assistant, it's, we're actually like lighting up TikTok and Facebook campaigns in the Philippines trying to recruit to vet more people there because that's a supply side. The demand of that side of that business is insatiable. Supply side is the challenge. Uh, not to say, I mean, it's big, it's growing fast. We're probably placing 25 people a month. So it's, it's a, you know, it's moving quickly, but it's like, how would you do that 100 a month? Like there's only one, at some point you have to find a way to scale it on the supply side. Um, for Unbloat, it's, it's a, it's a similar sort of like a, because it's not a venture funded business, like the CPA, like I'm trying to get it to first order profitable or one, you know, no more than 2 month payback. And once you have achieved that, then it's like, how do you turn that up and scale it? And then there's some retention's actually been better there than I was expecting, but it's, you know, you still want to get the economics working so that it's easy. And then the Kahani business has been, that's my first kind of foray into SaaS and like I'm learning. Obviously the benefits of it, you're like, wow, like the margins are amazing and people, you know, they'll just use this app. The challenge is like building a great product or product that works and knowing how to make it work has been harder than I think I expected. So that one is actually, we're trying to nail down 3 use cases that we, we feel 90% of the time confident that if we tell you to do this, it will have the result we expect. Uh, and that one has been an interesting one to kind of solve for. So they're all kind of in different places. Yeah.
And so does each one have like a full-time leader, like a CEO that you've put in?
Yeah. Yeah. We usually, we say GM or CEO, you know, but yeah, it has a full-time person there. And I'm kind of play— I play free safety in the sense that there's a ton of coaching and working with them on the goals and where we're going with it. But then I'm also jumping into each of them and especially around marketing, sales or other specific standing thing, helping them stand stuff up. So there's I'm definitely playing this kind of free safety entrepreneur in all of them. Yeah.
And are they, if you ask them, do they feel like they're the real CEO of the business or do you think you're actually CEOing the business?
I think it depends on which one of them you ask and how far along the business is.
Yeah. So out of the three? Yeah.
One and a half, probably depending on the day.
One and a half.
Yeah.
Yeah. Yeah. It's, it's super interesting. You know, I've, I, I told this anecdote the other day that my friend runs a turnaround fund where they would buy distressed stuff and fix it. And he had like 8 companies in a portfolio. And one day I was having lunch with him, he goes, Girdley, I've been CEO of all these companies at least once, sometimes more than once. I was like, oh, very interesting. So that was one of the things, for me, that's actually, my friends who are really don't understand my model, or at least are very perplexed by it. They're like, what, what do you, you know, is it this hard for you to like let go and let these people do their jobs? And I was like, it's actually super easy. Like, it's one of those things where I just don't, I don't have that control gene, whatever it is. You know, I want, I care about it, but I'm not going to stop trusting them to kind of do their job. And I'm not going to get in the way and do their job for them.
So yeah, I'm still working on it. I'm somewhere in between. You and that guy. Uh, and some, some of it is also, there's a lot, I think there are a lot of benefits to active coaching and, and a cohesive culture. And, you know, I've, I've gone back and forth on how, how decentralized for sure on the business side, but maybe centralized on the culture side and the learning side. And I'm trying to figure out how you do that. Yeah.
When I guess the inherent problem with you swooping in and, and swoop is a bad word, but. Of doing what you're doing as a model currently. And I guess you hit this, is it only scales so much, right? You know, you're— you can only have so many hours a day to do coaching and then secondarily, like, get in and get your hands dirty on stuff. And it doesn't sound like that's really a problem for you. I'm not hearing you frustrated by it.
Yeah, I mean, I think give it a few years and I think I'll have a better sense because there's an aspect of like Growth Assistant is a growing, mature business that requires less of my time and less of a way, whereas like Kahani, it's like, oh my God, my brain has to be involved in that problem in a very distinctive way. So I think part of what I'm hoping is that, you know, and then I think it's slowing down the pace of new stuff. I don't think we could launch another 3 companies this year and expect success. I think maybe 1. And I'm okay with that. I'm like, I don't need to launch a million companies. I think the goal is to have a handful and learn and grow and, you know, help a bunch of people develop some, build themselves. Like in so many ways, that's, that's my my, my North Star.
Well, and I, I don't, maybe you disagree with this, but I've come to the conclusion like there'll be power law outcomes for my ventures. Like, and I've looked at that, I looked at my personal financial statement the other day and it was like, oh, like only one of these companies really matters. Like as you know, compared in, in the grand scheme of things, like it's like a definite power law outcome. Of stuff in terms of my personal net worth and where it's gonna go.
Yeah, my version's like that, slightly different, which is all my friends are like, well, why don't you focus on one and make that one, you know, and it's like, I've just told my friends, you know, my business, I'm like, my goal is not profit, you know, expected value maximization. My goal is like life enjoyment. And like, you know, like enjoyment and purpose. And I said, so in that sense, yes, you're right. I'm probably leaving 20% on the table here. But I'm having much more fun every day and that's much more important to me.
It sounds so boring. I could not imagine. I could not imagine. And I understand why people want to do it. There's elements of that that are fun, but right now it just seems like the least fun thing I could do. I'd be totally unfulfilled. So I think your friends are wrong, for me at least. So I was curious about kind of the evolution of the Growth Assistant business. Like, you know, I helped incubate a similar business that's doing LATAM kind of hiring, but you guys have narrowed down around marketing and you've narrowed down around the Philippines and gone to— it feels like strictly like, I guess, an agency model is the correct one. Like, we started our South American hiring business primarily as a job board and it's migrated over time. They, you know, fortunately startups have been throwing tons of money at people to help them recruit people. So like, that makes it easy. But I was just curious, kind of your journey of how you got to the current model. Like, was this where you started? Or did you start with something else?
No, it's been like pretty straightforward from the get-go. I mean, and really, it started at Ampush, you know, my first company, we had built our own offshore team. And we'd have all these folks who would spend 2 or 3 years at Ampush, then go work in-house at a brand, and they'd call me and go, can I use that, that, that team? And we'd say, well, no, that's part— you'd have to be a client of Ampush to use to have access to that. And then the second question I would ask them is, wait, you're trying to tell me this doesn't exist in the world? Like there's no one who's building offshore teams for growth marketing? They say, no, we haven't heard of anything. And so as I started building GatewayX, it was like this idea was at the top of the list, especially if I could partner with the right person. And I found, you know, the right person in Adrienne. She's got a background in HR, recruiting, operations. And, you know, we stood it up, obviously. Or even today, I think 25% of the customers are former Ambush employees who are now working at brands. That's part of that unfair advantage, right? Is like, I already know the people who are there. Uh, but it's, it's been a model where we, we embed people in the teams. We're paying attention to their training and making sure they're, they're top notch. We're also training the clients a lot. We have a bunch of templates. So it's like, oh, you wanna do affiliate outreach? Okay, well here's the template and here's the person to do it and get after it. But, but I think the, the most unique thing about it has been the, the training and the embedded model. So it's like some, I always describe it as somewhere between Upwork, which is very project-based and one-off. And a normal full-time employee, which is expensive. And, and it's, you know, so they're, they're full-time, they're embedded, they're on the team, they know the context, but they're able to get a lot of these kinds of tasks and work done that are really, really valuable. And it turns out, you know, it's gone from— we started in February of last year and there we already have close to 200 people in the Philippines. So it's grown super fast and it continues to grow fast.
That's amazing. Congratulations. So that— well, we're coming up on an hour, but like, so that's How can people find out more about Growth Assistant? What, what other ways could my listeners or me support you?
Yeah, growthassistant.com or, you know, twitter.com/growthassistant. You know, we have a waitlist on there, but we work through it pretty quickly. And that's probably the number one, you know, love to have any of your listeners as clients there. And then, yeah, where I'm always looking for great people. So, you know, people hear this podcast and think, hey, I want to work at a place that is ambitious and successful but also uplifts people and isn't, isn't growth at all costs, especially people costs, then shoot me a note.
Yeah, totally dig it. Well, thanks, man. It's been great doing this, and I appreciate you being flexible on the scheduling and making time for it. And, uh, I'll continue to follow your journey and keep learning from the stuff you're doing.
Yeah, it's great to meet you, Michael.
Awesome, man. All right, and I'll talk to you later.
All right, see ya.
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