I found my zone of genius

All right. Jesse, we've been working together now for almost a year, and our relationship, I feel, has changed a lot in the last year. I feel before we were working together, there was a lot of like buddy-buddy text messages, and you're killer at that. I keep trying to do that, and it's not fully me, but I'm getting closer. Then we were in like building infinite possibility land together, and that was really exciting. And then it got to this, why the fuck is Andrew not doing this? And me going, why is Jesse constantly coming up with different ideas all the time? And it went from buddy-buddy to world of possibilities to this— I don't know. I don't— how would you describe where it is right now?

You know, I think every business has, and every relationship has different arcs and seasons, right? I think that's where I start with it, which is like that's somewhat. It's not totally abnormal. I think that it's been interesting from my vantage point to watch you kind of sort of the creative genius version of you versus the businessman version of you. They're pretty different. And and I think that like from my vantage point is like oh there was this creative genius who just like saw something in me. And part of the reason I wanted to start doing this podcast with you is so we can actually get out and. Get back to that. Get back to the things that make us, make you great, make us great together. And versus the, you know, I think the side of the business stuff is like, oh, you're running a business and like you want to run the business like I would run the business, but that's, you're not me, so you're not going to do that. So it's going to feel weird to you all the time and it's never going to feel great. And like, I think a big part of this whole thing working well for me with everybody is, is like letting them be the best versions of themselves, not of like a shitty version of me or my methods. And so, it's constantly like a question of how do you take those, absorb the stuff, but make it your own? And I think that's like a— there's a lesson there, I think, for anybody building a business.

Yeah, that's been a big wrestling match for me. Like, how much do I amplify who I am and how much do I take a step back and say, no, Jesse's got a different approach here that I'm trying to learn from. Nak has a different approach that I'm trying to learn from. Rachel has a different approach. How do you integrate? How much do you integrate? And how do you just amplify the part that's mine? How do I amplify the part that's mine? That's been challenging.

Yeah, I think it starts with knowing what your zone of genius is. And it's like, in some ways you can say that's a difficult thing to figure out. In other ways, it's like, well, what do you feel most energized and excited about? What do people compliment you on the most? What, like, you know, in your case, I think it's pretty obvious. It's like, You're amazing at directly supporting and networking, getting to know entrepreneurs and helping people do that. I think you're amazing. You have a great taste and content eye and perspective. You're very curious. You've got all these things. And even as you look at your history, your career and all that, it also becomes very obvious. And I think once you're clear about that and you're willing, but you know it and you're willing to stay inside of it, that second part's the harder— that's been the hardest thing for me. I learned my zone of genius at Ampush. But I wasn't actually willing to commit to my zone of genius until I probably started GatewayX.

What was your zone of genius and what could you not— like, what did you do outside of it that was hard to break?

Like, I knew I loved coaching and teaching people. I knew I liked starting new things and kind of the entrepreneurial energy. I knew I liked learning new things and building relationships and developing relationships. But when we were at Ampush, like, we tried investing in startups. off of our balance sheet. We bought a company. We launched something called AmpushX, believe it or not.

Wow.

It might sound familiar because I was like, oh, we're gonna go start a business. And so, I knew what I wanted to do. It was very clear to me what my genius was, but then I was still the CEO of the company. And so, AmpushX went nowhere because it was like a weekly meeting with me and 2 employees who were not staffed on any clients so that like, oh, let's go start a new business idea. And it just went nowhere because I wasn't engaged at the level I needed to be because I would like, every time a client called, I would run away. And you know, when I like left as CEO, Rick actually, he gave me sort of his feedback, which was right as it always is, which is like, he's like, no, you should stay as CEO, like make John the GM of Ampush and get it off your plate so you can go do whatever it is you wanna do. But don't, you know, don't fully give that up. And in my case, I just sort of said, okay, I'm out. Like, it's not working, I'm out. I'm gonna go start something brand new. willingness to actually stay in your zone of genius. Because when something goes wrong somewhere, when a client's not happy, when something's breaking, when, you know, you know this because you see that issue. And so the thing I see in you is you kind of know your genius, but you're not willing to commit to it. And usually you're not— people aren't willing to commit to it because they don't trust. They don't trust that they're good.

I feel like I know my genius. And I also feel like I'm the person who does the everything. I, I have to go and do every part of it and show people that I'm a part of it. And partially it's because I love being with people. Like, you know, we've got these guys.

Let's start with something like, what, What are the things— what are 2 or 3 things? We don't need to nail it perfectly. What are 2 or 3 things that you know you're really good at that also energize you?

I got 2. One is, I do love this, what's your problem, customer discovery, let's talk through and iterate it together. And the other one is, how do I bring people together, persuade them to try this new thing, you know? They're kind of similar, but those are, those are the big ones.

And what are things that you know actually you're not actually that good at and they de-energize you? Oof.

Writing a first draft of anything, even though I feel like, all right, I know what to say and I should just be— I could tell a writer this is what the first draft should be like. And then I go, no, I should just go do it because now it's taking too long to even explain to them. That's one example for sure.

So how many times have you done that in the last year to date?

The only reason that I can't tell you infinite number of times is because I just broke. I couldn't keep sitting and looking at that.

But you've done it a lot. You've probably spent 20, 30 hours of your year doing that.

That's fair.

So are you willing to just commit to not doing that?

You know, when you say that, I feel like such an irresponsible prick. Why can't you just sit down and type out what you wanna do or what you wanna say? Why does Jamie have to write the first version?

But herein lies— herein lies the issue with why it's so hard to commit to— you can know it now. You literally know it. We— and we got very specific and tactical. You know, you like bringing people in and doing things, but you're not. And so the whole framework is like, you're at 75, 80% of your time is in your genius.

Yeah.

And you're clearly not there. You're at 30%. So not only are you less effective, but you're also more burnt out. And what keeps you there, what keeps everybody there, is the stories. And it's scary. Like, when I started GatewayX, like, The first time I saw Adrian doing something weird, I wanted to grab the steering wheel from her and go, no, no, no, no, go here. Right? Or like one extreme version is grab the steering wheel from her. Another version is like yell at her, tell her what to do. And like none of those are right because those aren't— those just aren't like— they would have led me down this other path. Right. And I think it was hard and it still is hard sometimes to commit into my zone of genius and be willing to go, no, I'm not going to like go run the staff meeting for Growth Assistant. I'm not going to go pitch the client on the upsell. Those are, those are 2 things that I would call my zone of excellence, by the way. Like pitching clients for sure, zone of excellence. Like, does it, you know, doesn't necessarily energize me. Sometimes it does, but, but doesn't often energize me, but I'm amazing at it. Um, and so I think that it's, it's a pretty high bar and it's a pretty, in some ways I think most people just kind of like roll their eyes at it being unrealistic. Um, I think it's one of the most life-changing things that I've done for myself.

I, I do feel it's like it's understanding and persuading is probably it. Like in one moment it's the understanding through customer development. What's the problem that they can't solve? How would they want help solving it? That's customer development. The other one for me is persuading. Like I wanted to have this dinner tonight here. I wanted to have the speakers of the conference to come over to my house. And I knew that there's like a Path to doing it, to understanding, to persuading. Those are the two. What would you say?

Yeah, there's something else there.

What else? You're seeing something in me I'm not seeing in myself.

Yeah, I mean, there's— have you done the Genius Exercises?

No, I'm afraid of doing too much with Dave Kashin by going, okay, help me plan, and I got updates for you on that, help me deal with this other stuff, and also help me deal with Zone of Genius. So that's why—

Put him to work. I mean, that's— His job. Um, I'm like his Chirag. I like, I get everything I can out of him.

You, you know, you are really good at that. So I, I keep telling Chirag, here's what I'm watching that Jesse does. Like, for example, I always thought you have a coach like Dave Cashin working with me. The, the thing is I have an hour with him every 2 weeks. That's the limit of what we paid for. That's the limit of what we have. And you said, go text him in the middle of the week about this thing. And then you said, if you're having an issue, just message him right now. I go, but text? He goes, it's too much. And you said, he's an adult, he'll tell you if it's too much. I actually have a question for you about that. I don't know if now's the right time, but— Yeah, go for it. Okay. You will say, ask this person to do the thing, they're an adult, they'll tell you no. I get that, and I do think I need to ask more, but I wonder if you realize the power that you have over people and their inability to say no to you, and maybe that's on them that they should learn. But if you're asking, say, a writer to also edit something else, or video producers also, they won't say no to you the way they might say even to their mom no. They feel like they want to please you, and that's— what do you think?

Yeah, I think— I mean, look, I think it's important— there's 2 pieces to this, right? One is like this concept, I think, from Conscious Leadership around 100% responsibility. Right? Which is like, when there's— between 2 people, there's 200% of responsibility, and we should each take our 100%. And if I, if I worry about asking you for something, then I'm taking more than my 100% in our relationship, versus you being independent and me going, hey, Andruk, will you do this? And you go, no, I can't do that right now, I can do it tomorrow, or whatever that trend. So, I think, I think practicing that as a general frame is really valuable in every relation, even in your marriage. Like, the, the concept, you know, the, the lingo that people use is is heroing someone, right? If I ask my wife, can you wake up in the morning and cook me breakfast and take care of the baby and drop the kids off? And she's like, well, he's tired. I'm going to hero him. Like, I'm going to do that even though I don't want to do that. That's called heroing. And when you hero someone, you're taking more than 100% responsibility for, for like your relationship dynamics. And what happens? What do you think happens when you do that with someone?

I think if I'm heroing someone, I there's resentment that just builds up and then you break the person.

That's 100% what happens, right? And, and so it's not like it's, it's not like it's costless. Like, yes, in the moment it's easy to hero some situation, right? The opposite of heroing is like either blaming someone or you're pulling back and being the victim and saying like, I'm not going to, I'm not going to do my part here. I'm going to, I'm going to run away from this. And that's kind of this whole concept of 100% responsibility on both sides. So I think I like to stand for the concept of 100% responsibility. Which is, which is, yes, I can ask for anything I want. And you can also tell me yes, no, maybe, or negotiate it back. And so, some of it's just teaching people that and getting to know it, I think. And with that said, I think that, you know, you do have to be mindful of power dynamics, um, for sure, right? And, and I think like power dynamics in for, for a junior employee versus whatever, like calling it out. It's okay to say no here. And I wanna ask you for what I want. So, the idea behind it is, is to, is to create the space.

Mm-hmm.

But not like a, you know, sometimes people call it negotiating against yourself. If you already start to go and say, well, I don't want to put pressure on them today, so let me wait till tomorrow to ask them. And you're all of a sudden you're playing all these games that are very actually energetically draining if you think about it, because you're like, well, I don't ask that person now, let me ask them tomorrow. And this person this and that. And you kind of just go, hey, you can say no to this and I want to ask for my 100%. Dave sent me this thing one time that was like, ask for your 100%, 100% of the time. Be willing to hear no and negotiate for a win-win. And I think that's the best formula version I've heard of it. Always ask for 100% of the time. You ask for your 100%, but you're also willing to hear no. And then you're— and then both parties are willing to negotiate for— and if you think about—

Yeah.

It breaks down at one of those things. Either you don't ask for your 100%. That's one way it breaks down. You don't do it 100% of the time, so you only do it some of the time. Right? You're not willing to hear no, or the— or both parties are not willing to actually have the conversation around a win-win. Right? And if you— if all 4 of those things are true for both people all the time, it's an incredibly, like, healthy and empowering relationship. And I think it's important to train people. And the best way that I've done that, by the way, as a leader, is like, I let people say no to me. And I'm like, oh, I'm so glad you said okay. Let's— but let's find the win-win. Like, what's okay? You can't get it done today. Let's get it done tomorrow. Or like, can you stop doing that other thing and I think once you get people trained in that way of being, it's highly addictive.

I like the, you can say no to me, but I'll ask you for the 100%. I do think that makes it easier for me to ask for things, because I do struggle with that, because I feel like I want to protect people. And part of protecting people is protecting them against imaginary problems that they don't even tell me they have, but I'm assuming that they don't want to take on this extra responsibility. And sometimes it's the opposite. They do want more.

But here's a— here's a— here's one that might stun you, Andrew, is you're taking on the hero position. Can you see that?

I do that all the time.

And what is that? But what does that mean? You think about the other person, that they need my protection. Because if you're on the hero spot, where can they be weaker than me? Correct.

You know, I do.

Jesse, you're treating someone like a victim. You're literally saying someone is less than you. When you take that posture, you're putting them beneath you.

Not only do I do that, sometimes I do that intentionally as a way of building myself up. Like, I'm gonna do this because now I'm seeing how strong I am. And it's, it's little things like, I'm gonna show how strong I am at doing this work and that maybe you need to get done. Sometimes it's, I'm gonna show you how impressive I am that I can now drink you and still show up the next morning to go take care of the baby. And you're not even checking on what I'm doing with the baby. You don't even know that I have a baby. But in my head, it's like the way I build myself up.

Yeah. I mean, and that sounds consistent with the pattern and you're, you're a 3 in the Enneagram. You're like, you have some deep fear that you're not enough or that you have to keep proving yourself. And so these are all these various ways that you keep trying to, to make yourself better than everybody else.

Yeah, I do. Um, yeah, there was when we were doing that 8-3-3 meeting with other founders and there was another one who was a 3 and I said, Not only do I need to know that, to have people tell me that what I've done is great, it has to be absolutely irrefutably great, and I need like evidence, and then I could go, okay, this is good. Which is why running is good, because I could finish a marathon and know, okay, I hit this number and I'm good. But if you just say, hey, great work, Andrew, I like this article, I'm like, did you? How do I know that it's really right? Where's the metric? Where's the outside proof? Where's the rigor? By the way, I'm drinking a shake now. I've been, you know, I've been working on how much I'm eating. How the hell do you not eat all day, especially with the stressful work that you have and everyone else dumping their problems on you? The shake is not even doing it for me.

No, I'm not, I'm not. I have another 2 or 3 hours till I have my shake.

Yeah, don't you feel like you get stressed? So the worst thing about working from home is there's always food around. Though I remember the GatewayX office also had my number one snacks, which is nuts and seeds, that kind of a thing. How do you go to whatever— what are we now, 12:30— without eating, especially when other people are dumping their stress on your head?

I go till 2:00 or 3:00, I think. As long as I stay busy, I think, on these calls or whatever, I don't really— I find the easiest thing for— honestly, once I start eating, I find it hard to not keep eating during a window. But as long as I'm not eating a lot of liquid, coffee and water, I find like I can really block it, and then I can start eating.

Yeah, there's something about having a no in my head. I know I'm not eating until noon, so it's not a question anymore.

Yeah, exactly. I think that works in a lot of things.

All right, so you were saying that you see the genius that I'm not noticing. How do I get to notice this?

I mean, there's a couple exercises, right? One is there's this exercise the CLG people have, which is just email the 20 people in your life, And I ask them like, when have you seen me most energized? What do you think I'm best at? And by the way, they say that genius is like asking a fish if they're a good swimmer. They don't even say— they say, what do you— what's water? I don't even know what water is. So I don't even know what you mean by the question. Like when you tell me that I'm so good, like riffing off of people and giving them feedback, like it just, it's so natural to me that I don't even realize I'm doing something like that. And so you, I think getting other people to reflect it back to you is a really powerful way to figure out what your genius is. Um, there's a couple other exercises of like reflecting on times you worked your best. There's the energy audit, which, you know, you look at when, when you've been energized versus not.

I did do that actually before we were working together. You gave that to me and now I want to go find that Notion doc where it basically what I was doing was keeping track, keeping this Notion doc on my computer all day and anything I did, I would mark what I was doing and then write whether it gave me or reduced energy.

Well, there's something about you, Andrew, around information and content that you have a genius around.

Hmm.

Like, you can— it's some of it's you have this unique curiosity where you constantly ask questions or you, you sort of probe and ask these questions. Like, here's an interesting example. We had that very private conversation with Rick Elias where he shared a really private thing about himself and was like, you know, and he wasn't going to do that. He just said, I had a tough couple of years, and everyone was like, okay, and everyone was satisfied. And you were like, huh, give me a real example. And then the example he shared, we were all in tears, right? It floored all of us.

Yeah.

But like, so there's something you— and I think the same thing with me, you've done that a lot of times. Like, I think the whole Sales Accelerator was a function, and much of what Bootstrap Giants is, is you doing that. You found these situations where you've been like, Um, well, hold on, wait, how did you get that meeting? How did you meet Supercell? Like, what was that client? And, and there's something that you're really naturally good at digging in, uh, that I think is part of that. And then you find an angle or you find the unlock. You then connect it with people who need it the most. And I think there's an element of that too. But, uh, yeah, I think that— I think you shouldn't undervalue your taste and your ability to kind of like see something content-wise or information-wise other people don't see.

Yeah, I see what you mean. Do you feel like you're— I know you took this big change in your life this year where each business was going to get one day. I know that your calendar was chaotic. Do you feel like this is reducing the chaos and allowing you to live in your zone of genius?

That's a good question.

Um, what—

so I think the context switching has been helpful.

To not have to go from Aux one day, on the same day, Aux, Bootstrap Giants, TechCrunch.

In the morning and then Bootstrap Giants in the afternoon. And then I think the clarity for everyone else has also been super helpful of just like, if you work on Aux, you're like, Jesse's available Tuesday. Um, I mean, this is a great topic to talk about because it's very present for me right now. I think what it has also led to is that like everyone crams everything into this, these days. And then my days end up— these 3, the Monday, Tuesday, Wednesday end up feeling like crazy for me. And if I'm a little off energy-wise or I'm not fully there present, like, I— it definitely just drains me by the end of it. And then I think what's happened with Thursday and Fridays is, you know, Friday has become this like marathon networking or like all the other calls basically get dumped into that day.

Mm-hmm.

But then You know, it just ends up with a situation where my calendar is completely packed, and it's not even that I like want to get any work done. You know, I don't like doing work. Like that's not a thing I like to do. But it's it's honestly like I like I'm I'm more more I'm growing in my spiritual journey and my personal journey. Like type seven, one of the things about the Enneagram type seven is they like to fill their calendar with things because if they have free time, they literally feel anxious. So they're like it's a way they avoid feeling. And now that I'm like more in touch with my feelings than I ever have been, I actually find the that I don't like it as much. I just want spaciousness. Like I literally want I want an hour where nothing is booked, where I can, I can putz around and like not do anything or pick up something that I haven't done in a minute or read. Like, another thing I realized is like, like listen to podcasts or read, read stuff. Like, I don't, I don't have any time in my day for that stuff. And that stuff can be really valuable and important.

Yeah.

Um, so it's not, I think I'm like, it's, it's better in some ways, but it's not fully, uh, it's not fully where I'd like it to be, I don't think.

Yeah, I feel like you're not quite where you need to be, where I think your, your genius is in coming in and doing what you did this morning for our members, where they had this problem and you came in with this like light bulb solution for them. And that, that's where you're great. And I feel like instead we end up putting you into look at these slide sessions and Why don't you give this kind of feedback on this thing, saying the thing you've said 12 times before?

Yeah. I mean, the way I would describe it at a high level is I think I'm still pretty heavily operationally involved in all of the businesses.

Yeah.

And I think that's probably not— that's probably more zone of excellence stuff. And I think, I think some of it is I'm also— the flip of it, by the way, is like, you know this from the Dave work, like I can resist the reality of where we are now. I can change the reality of where we are now or my willingness to participate in it. I could say, guys, never mind, I'm not going to do this. I'm, I'm the chairman, you know, you get that, you all get, you get 2 hours a week with me each and you talk about your problems and I'll help you build the business. That's all I do. That's one way to solve it, which I could do. The other flip of it is like, no, that's, this is like where we are right now, as, as like, this is where the thing is right now, and accept where it is and show up with 100% against it. And I think like when I look across the businesses, like You know, Carolyn just started doing marketing for Growth Assistant. You know, they, they just finished kind of a one big cycle of iteration. She's figured out what channels she wants to prioritize. She's doubling down on those. Like hopefully within the next few months, there's gonna be more of like a, a motion there that's, that's going right. So there's certain things that Growth Assistant, that's like they're operationally involved. Aux right now is, I'm engaged with the case teams. I'm helping Casey recruit some senior people. Those are pretty operational things, but like, again, they should create more scale, like some more like independence of that business. And BG, we're, you know, we're figuring out various things. We're still making content. So I think part of it is also just accepting where I am right now in all of this and like it being like it's going to be part of the journey of getting it to the point where I can be that zoomed out, I believe, and holding myself accountable to not falling into the trap of next quarter signing up for more operational stuff.

Yeah. Do you think that maybe instead of launching these companies within GatewayX, it's better for you to just buy companies that have some momentum but don't have— but they're blocked, they've hit some plateau?

Yeah, have we talked about that?

No, but I'm seeing that this is chaotic and this is the messy part of entrepreneurship. And I can see that you're good and excited about it, and it's much more let's make it up, which is creatively fun, but It's also draining in little things.

Yeah, it's funny. It's funny. We— I thought we— I mean, we've talked about that a little bit, maybe, but like, you know, we decided not to start a new business this year, partially because of all the things we're talking about, partially like, you know, and this is another good sidebar we could take is like, I've also learned to trust my energy a lot more. My energy has become like— I've— I think it took me a while to learn what it was. Then it took me a while to trust what it was. But now I trust it. My energy is like, nope, don't do anything new. You've got plenty going on. But I think given that we've got more scale across all of the stuff we're doing now, that plus like the starting a new business every year, even co-founding with you, co-founding with Casey, like your experience is like— and for Casey, for let's say that first year was tough, the first 15 months was tough, but now she's like got a real business. It's got employees and like it's not gonna— it's tough in different ways. But my experience has been the slog of the freaking first year of every business every year, which I think—

Yeah.

I was super hyped about for a minute and now I'm like, like, just not as excited. Now, that might— I might start another business in 2 years, maybe, maybe not. But it's definitely driven me to going like, yeah, wait, I think I do want to start it. Like, or I think I do think M&A is a more interesting path for me. It solves a lot of things. It solves that issue, right? So you get— no matter how good the idea is, I think Aux is one of the best business ideas I've ever had and we've ever built.

Mm-hmm.

And yet it still took us a good 2 years to get it to like some sort of— I call it gravitational force, right? You kind of have to like— the first cranks of the shaft you have to do a few times. And, and so I'm like, man, I'm like a little sick of that slog and I just don't want to do it. I think that's one thing that's driving me. I think the other thing that's driving me is leverage. Like, again, it takes time to get these businesses to leverage, whereas you buy something, you can get a lot more leverage very quickly. Um, and then I think the third thing is, uh, is like it, it will be different for me. The expectations will be different for me to work on the business versus in the business. Like, I think co-founding a business with someone, there's just an expectation that I'm going to be part of the building of the business. Whereas if I'm like the owner, I bought it, it's like, oh, he's not like— there's a business that runs and he's sort of helping make it better, but he's not in it.

Yeah.

And so I think that's driving it. And I think the other thing, we've proved a lot of interesting things. Like, we've learned from Aux that like growth marketing can be a really effective lever for businesses you buy. We've learned from Bootstrap Giants that there's a ton of founders out there who are stuck and there's like ways I can unstick them. And I can actually have a lot of impact from the outside in. So I think there's like all these interesting things coming together. Then there's this whole AI thing, which is another vector we've been spending time on of like, now can you bring AI into the picture and what does that look like? So I think it does it like I am getting excited for maybe the next season here to be more about M&A and at least to try it like it might not work, but, but I'm open to trying it. The other thing, by the way, energetically is like wanting to take a big swing. Like all these businesses we've started so far, like GA, Aux, BG, they're great. They're all like, they were like high confidence businesses that were going to work. I think they didn't feel like hugely risky businesses. And I think like I'm, part of me is craving a little bit bigger of a swing.

Well, so what's a big swing?

Meaning like, um, roll up, go buy a $50 million company, one that I might totally fuck up. Maybe, maybe, maybe buy one every 2 years. I don't know. Like, but But it's a big swing. It's like, no, go do, go like, go, go try something like that you don't know how to do, that you haven't done, that could fail. Yeah. Like none of these businesses have felt that way.

That— so is this you though, going back to the way you were before where you needed risk in order to really perform?

I don't think so. I don't think it's not fear-driven. I think it's just like a, it's like a I feel like, honestly, I feel like fear has driven my decision-making around some of the more boots— some of these bets. Like, I didn't want to fail, and I think I actually have more of a willingness to fail than I did in the past, um, to have like just like a bigger platform and more upside. Like, the other— here's another frustration I've shared with Knack that's an interesting one. It's like, because of BG and a bunch of the things we're doing We have so many smart people. Like, let's use Michael Riley as an example. We have so many smart people around here and we can't keep Michael Riley because we can't— like, we don't have— we don't have enough going on here that can pay him enough and make it upside more interesting and all those things. Like, somebody like him—

Problems too. Yeah.

And like, we've got— we've got tons of smart people who want to work with— with me and work with us because of this. And I don't have enough. And that's like one cool thing about a private equity firm. And Aux re-showed me this, like, Aux has all ridiculously smart, motivated people. We're paying them all a lot because It's like a premium business. And I'm like, oh, it's so nice to just work with tons of smart, motivated people. Um, it's, it's a different person type of person. It's, it's like, uh, it's like, uh, Lauren, who, who you're talking to, like just a different level of a person in terms of skills and capabilities.

Lauren and Ben, like, I still wanna talk to you about both of those, but AI keeps coming up.

I'm wondering what, what you're seeing in AI, because the little bits that I see don't feel like they're big, and I don't know what you're, what you're I think that, you know, when I first started working with Facebook ads, we were trying to convince brands that they were gonna be something, and they weren't at the time. Like, you could get likes. I think they worked for daily deal sites. They were these right-hand rail ads. They were pretty shitty.

Yeah, no one takes it seriously.

And then one day, and yeah, we've talked about this in the past, I like, I love the concept of sandbox entrepreneurship. Like you find the right sandbox, you play in it, and you're gonna figure out what's there. Then all of a sudden the mobile phone became important, then the newsfeed became important, and next thing you know, you know, Facebook ads were the most important thing that was out there. And so I actually think it's interesting, and the hype cycles are what they are, and so on and so forth, but I think, From what I can see from AI, and like, in the— it's a really interesting situation where the level of advancement is unlike, I think, anything we've ever seen since maybe the mobile phone or the internet or the—

Yeah.

Like, it's that level of scale. But hype is even more than the reality. Like, the hype is absurd. And I think that turns a lot of people like you off, that, oh wait, there's too much hype there. I think the few examples of— I invested in this business called Figure, the robot company. And like, I know the founder. It's a crazy company. I mean, it's, it's like a— I invested at a $350 million valuation. It's getting valued at $38 billion right now. It might make— it might make me more money than Ampush made me, which would be hilarious. But the things he's showing me are crazy. I mean, these robots are teaching themselves what stuff is the first time they've ever seen it. And when I see that stuff, I go, okay, that is— I believe all that. And then you go back to our world and you're like, can we make a transcript of a thing? Can we make a Twitter Thread? No, we can't. It sucks. And actually, for me, Andrew, that's what gets me excited because I'm like, wait, the DFS versus the current reality is so far away that there's going to be massive opportunities. Now, if we— we're all like relatively tech forward, we're in the circles, we can't figure it out. Think about these like private equity owned businesses that Aux is helping with. I mean, Aux is doing work that's 10 or 15 years old at this point for a lot of these private equity backed companies, like the stuff Ampush was doing 10 years ago. We're now doing that at Aux for certain of the private equity-backed businesses, right?

I see.

So I just see a massive opportunity of being an early adopter to something that I think is gonna be huge, even if it hasn't yet proven out that there's a there there. Like, I see the value in being someone who goes and figures out how to put it into play.

Yeah, I talked to Casey from Aux, and I said, is there an opportunity to create an Aux for something else? Like, what Aux does is marketing advice to private equity firms, and I know she says it in a different way, but She thought, well, do the AI version of Aux. Is that what you're thinking of, where you go into businesses, private, I guess? Yeah, you go into businesses.

I mean, I would either probably start that as a part of Aux and just make it a practice group inside of Aux, um, because Aux already has the relationships and the distribution, and it's sort of indifferent for me. What we're thinking is like the first thing I want to do first with Growth Assistant is actually AI-ify Growth Assistant, right? And like, what does that mean, Jesse? Yeah, I don't know. What does that mean? I mean, I could give you examples, but I don't know, actually. But that's exactly the point, is that I want to go there and go, okay, sales team, what are your problems? Oh, you know, you don't know when to upsell someone. Oh, people are using different scripts. Okay, can I use AI? And it could be Gong, it could be third-party tools. It doesn't have to be, you know, some core languagey stuff. Or how is Carolyn doing marketing? How's she writing emails? Let's go try to solve a bunch of problems. And even the product itself, How do we enable the GAs to have AI knowledge and what does that do? And at the end of that, there's, there's, you'll end up in one of 3 places. One place is we tried this for 3 to 6 months and it was useless, which either means it doesn't work or we're too early. Right. And I would go, okay, that was great to learn that. I'm glad I could learn that before I went too crazy on it with a company I knew and it was low risk and I own, you know, like this, the second other, the flip side of that is holy crap. Like the DFS for it would be. We double— like I told Adrian, I was like, we double the revenue of the business without growing costs at all. And if we do that, not only do we have more financial resources internally, but holy crap, now I've got a way that I can go buy businesses or I can transform businesses that like I only— I know I literally authored it with my own company, right? And then the middle one is like, there's— there, it's somewhere in between one of those two. And in that case, maybe you start a consultancy, maybe there's some other play that Maybe there's a product you figure out that you can turn into a SaaS product or something like that. But part of it is you— I, at least, you know, you and I debate this sometimes because you like to research and talk to people. I like to go do things and I like to figure them out experientially. And I'm like, if it works, like, I don't want to talk to anybody about this AI stuff. I want to, like, go do it and I want to see what happens.

You invested in this. The other thing that I thought was super interesting Is you invested in a private equity fund? And I saw the amount that you invested. I saw the direct connection. I didn't know that you could do that as an individual. I gotta ask you, just give me some, like, what are some of the things that you invest in? What do you do with your money? Is this awkward? No.

I no, no, not at all. I I don't think I don't think I do anything that special. I guess is where I was gonna go. Like I I probably you know if you if you say say I have ten million dollars right just made that number up. I think of it as well. There's a couple different ways I think about this right at a high level. One is like you have a certain amount of income you earn every year. Let's call it make up numbers a million dollars a year. You spend say $600,000 a year. You keep adding some cash every year to that thing. And then what's the portfolio that it goes into? And my DFS is probably honestly like 50% the index at this point. I'll tell you what I used to do, but like 50% the index and like 25% private equity, private credit type stuff like the private equity fund, or there's some other interesting private credit things and 25% real estate. That's kind of my DFS.

What I've done— Regular real estate is what you'd like to buy?

No, real estate funds. Real estate funds. Or there's like, there's these operators I can send you an example, but they're like, they go buy apartment buildings in Arizona and they have a, you know, a whole system that they use, whatever.

Okay.

What I've done historically, you know, we'll see how it all nets out. I think one is if you look at my— like, it's probably more like 20% random angel investments, which I'm like done doing. Even if this Vigor thing pays out, like, it's just— I got attracted to it because I like entrepreneurship and I want to work with entrepreneurs. And I was like, oh, cool idea. Write this check, write this check. And then it takes forever. And like the liquidity thing is so annoying and such a huge issue. And then even and then like you're losing money and you're not really involved with the companies. Like I just didn't find it to be gratifying at all or exciting or enjoyable. And I think I'm pretty shitty at it. Like maybe I'll it'll I'll pull it out at the end, but I don't know that it's going to have good returns. And then the other thing I was doing that I've stopped doing is stock picking. Similar like I thought I was so smart. And by the way, I've made some really good bets. I The best one I've made, dude, is when we were selling Ampush. I can tell you it was October, November of 2022.

Okay.

Okay, we're getting term sheets for Ampush, and we're getting term sheets at like 10 to 12 times cash flow of the business.

This is the final part of Ampush?

Final part of Ampush, we're selling the company. And Facebook stock, because Apple had done that thing where they had changed the data, And basically like, oh my God, you know, advertisers aren't knowing where they're going. Everyone's freaking out. Their stock had dropped to $90 a share, which was 6 times Facebook's cash flow. And I was just like, this makes no sense. Why would Ampush, whose entire business is built on Facebook, be worth, you know, double as a multiple? And then I called John in the middle of this. I'm like, hey, did you, did you figure this out? He's like, yeah, we figured it out. Like, we know exactly how to solve the Apple issue now. And of course, I knew Ampush was on the bleeding edge of figuring things out. And so I bought a ton of Facebook stock at $90 a share. And look at it today. And you're still holding on? I'm just holding it. Yeah. I mean, there's—

How much did you put into Facebook at the time?

Like a quarter million dollars.

Okay. Oh, wow. It is $672 today.

Yeah. And you can go back and look at that. But anyway, so that was a pretty good stock pick. I guess I'm not the worst stock picker, but in general, like, I think the reality of it is Outside of maybe one, one or two instances like this, like most of the stock picking I did, it did not go well. Like I bought some SPACs or whatever and the index just works, right? And if you just do the math on it, if you have, you know, $10 million and you put $300,000 in a year, and this is another funny mindfuck of all this stuff is, and you compounded at 7% or whatever, like you're gonna have, as long as you keep earning money, even if you don't, by the way, but like you're gonna have $50 million by the time you're 70 years old. And then the question is more interesting, which is what the hell do you do with that money? Because my big issue is like, I don't know what to do with the 10. What am I going to do with the 50? And it's like a funny mindfuck because we spend so much time trying to earn money. And then what are you going to do with it? It's been like a weird existential issue for me. I'm like, I don't actually know. I don't want to leave much to my kids. Although that starts to seem— that's actually seeming more attractive these days because of all the stewards of it. They actually seem like they'll potentially be the best stewards of it, right? Yeah, I want to give to charity, but charities, even like as someone who's like a hard-nosed entrepreneur, I like look at what they're doing. I'm like, I don't think you're good. You're going to make a lot of use of this money. Well, yeah. So should I start my own charity, like my own nonprofit? Like, that's a thought I've had, like the GatewayX version of, of like a nonprofit. Then you can give it to the government. No thanks. Right. Or you can spend it. And so I've actually gotten the spending has become a more interesting option, honestly.

And, you know, did you ever not enjoy spending money? I, I do see that you, you got a second house, maybe even a third. I can't tell. You seem to be actually enjoying the skiing, the relaxing, the taking space.

Yeah, I think, I think it's been a part of my personal spiritual journey for sure. I think, um, it wasn't always easy for me. I think, I think you just think it was—

Why are we calling it spiritual journey when it comes to like spending money and having fun? Is it just the way you talk?

Yeah, because— no, because I think— no, no, no, not at all. I think shifting from fear and scarcity around money to abundance and love and openness, that's the shift that's actually made me enjoy money, not the money itself. Because I think before, I would be freaking out about, okay, what are the scenarios here? I need to run them, or I shouldn't spend X on a second house. Like, that's crazy, right? Or just like, or like, like buying a business. Like, I was talking to my dad the other day and my dad is like a, you know, he has a bunch of real estate that he's built himself in San Diego. And my mom was texting me and complaining because they flew to Dubai where my grandparents, my grandfather lives, and they went premium economy, right? And so, you know, I was like, that's crazy. And I was like, why aren't you flying business? He's like, it was $8,000 round trip per ticket. And normally it's like, yeah, that is a lot. Like, that's offensive. Even when I say it right now, I'm like, ugh, that's a lot of money on a plane ticket. And I was like, you're this many years old. Like, you know, I was like, I donate 20% of my inheritance so you can travel business class for the rest of your life. Because, you know, there's this really good book called Die with Zero that Dave Kashin had me read after we sold Ampush, and it was so powerful for me.

Yeah.

Because I started to really— and that's why I call it spiritual journey, because a lot of it for me has been in, in allowing, like, allowing myself to enjoy it.

When you say spiritual, are you talking about like my spirit, meaning my energy and what lights me up, or spirit as in like the way that we say religious when we don't want people to think that we're nuts?

Neither. Spirit— I mean, there's some part of the religion, but spiritual means that like there is a part of me that's not this physical body and not this physical form. Right? And the more we're in the physical form, then money is also— it's like all these things matter. It's like the, you know, it's like when you lose perspective on something, you're fighting with your wife about the pen on the table and why is the pen on the table. It's like, how much perspective have you lost? But like day to day, we lose perspective. We'll go, this is my— this is me, this is my whole life, this is everything. My bank account is my life, that is everything. So when I say spiritual, I'm like, no, you let go. Once you let go of attachments to that stuff, you spend it more freely. Like for me at least, I, I can't speak for anybody else, like I Some people spend it out of insecurity, by the way. Mine was the opposite. I was like, no, no, no, I got to hold on to this stuff. Like, I don't want to— I don't want to lose money. I don't want to mess this up. And as I've gotten a little bit more less attached to it, I'm like, yeah, like, spend it. And there's been a bunch of things that have helped with that, obviously, like starting— starting more companies and those being more successful. Like, there's been things that have helped me get to that point. But— but spiritual— like, the spiritual journey has definitely been a part of it, which is just being more of like This is not— I'm more than this body, than this bank account, than these other things.

Why not buy real estate directly? Is there— I mean, is there the same benefit to having someone else manage your real estate and be a part of someone else's real estate portfolio versus owning it yourself?

I honestly just haven't been able to make the time or get excited about it. It's the honest-to-God truth. It's on my list as like— my dad's like, why aren't you buying multifamily buildings? Why aren't you— real estate's the only asset. And I'm like, you're right. And then I'm like, I don't want to go look at a bunch of 8-unit buildings in St. Louis or wherever and then have a property management business. Of course I can do it. I have the energy. I mean, I'm starting a million things, but I just haven't been able to get excited about it. And then I see these guys who are good operators and it's like, this is their business. Like, let's just write them a check.

Like, is your brother doing this on the side? What is he doing? Airbnb or something?

My brother-in-law does a lot of real estate stuff. He's done it since he was like 21. My younger brother works with my dad and owns a multifamily place in San Diego with my— alongside my dad. My older brother, my older brother and I basically have just never sold a house. So I still have my place in San Francisco. Like, and—

You're renting it out?

Yeah, we just rent. I mean, like, just kind of like the— I mean, I have a 3%, 30-year mortgage.

Wow.

Like, yeah, in, in Noe Valley. Like, that's going to be a great asset.

I can't believe we lived so close to each other and we didn't even know it.

That's crazy.

I would've thought we'd run into each other at the farmer's market. All right, I like this. You know what this to me is like? If you talk about— I don't know that I'd say this zone is genius or not, but this is one of my favorite things to do, to just have conversations like this. And I do feel like our relationship needed this. Frankly, I feel like my wife— maybe I should just do an interview with my wife and then save it in our files.

When you came and met my wife, she was like, damn, how did I get so deep with this guy so quickly? She was great. And it's so funny because Because that happens with you and Dave Kashian in totally different ways. Yours is more like a podcast interview where all of a sudden you're like, well, why that? And what do you think about that? And Dave is like, she's crying within 10 minutes of talking to Dave because he just like, he asks a piercing question and then just stays quiet, as you know. And then next thing you know, like the tears just start flowing out. That's so funny. All right.

So we're going to do this more often. We're going to post it. And I have anxiety about the numbers about it. I have anxiety about people seeing that it doesn't have millions of views. We should talk about that in a future session. But I have to say, I do enjoy this a lot. I like talking with you. Cool.

Likewise.

Thanks. Bye everyone. Bye.