The Exchanges

Q So, so let's just use like you as the example, but I think this can be extrapolated to other founders that that million dollars from ampush that's kept in escrow. What happens now?

A Yeah, so, you know, we, we left a million bucks, uh, there. We tried to wire it today, uh, after that announcement, and it's not getting wired, obviously. What, what, you know, I don't know, is a short answer, no clue. I think the smart people I've spoken with said, well, look, 250,000 you'll get, and you'll probably get it next week, because it's insured by the government, which is nice. And then the other seven 50, like, you're in line, you're, you're, now you should be a senior creditor. To whatever this, you know, receiver, when someone says receivership, that means bankruptcy. It basically means you've been put into bankruptcy so that somebody else can over watch the, like, liquidation of something. I think there, I've heard lots of rumors, unsubstantiated, of course, that, like, they will get bought over the weekend, like JP Morgan or somebody's going to come in and buy them because now that the government stabilized it, someone could finally.

AI assessment note: “250,000 you'll get... and then the other seven 50, like, you're in line”

Q to the way that you used to, um, show up when things, like, were going wrong, and I think the story that I've heard you tell is, there was some big account that you had at Ampush. Ampush was one of, you know, the largest Facebook paid marketing agencies, one of the earliest, and was it with Uber? Well, there was one account that basically you were about to lose

A Two stars, yeah. Well, I think, yeah, you're, there's a, I've told a story where, like, we were about to lose Uber, and they were taking big parts of their business in-house, which is not abnormal in our business, and I came in, I was like, well, why didn't anybody tell me sooner? Why am I just finding out about this? Well, who, who, who did like, you know, who's to blame and what's going to happen? And, and, you know, kind of the team, I said, okay, we got to go pitch and win this business. And the team puts together a pitch and we pitch it and, you know, we lose it. And I'm like, oh yeah, whatever. I made up an excuse and I moved on with my life. And I just wasn't aware of how people were feeling or what they were thinking in that moment. And then fast forward a few years, a different account, which was our biggest account at that time, stars, They were, they had actually fat fingered an email or no, sorry. Our Facebook rep had fat fingered an email to our team and said it to the client basically informing us. And I get the team together. I'm like, okay, let's retain the business guys. We can win this. And I like ask them to do, you know, work on a draft and I sit back down and the draft is horrible. And now I've done some work on myself and I'm like, oh wait, I'm like, I'm picking up on it. Oh, everybody's pissed. Like, you know, in a business like that, a service, you reall…

AI assessment note: “I've told a story where, like, we were about to lose Uber”

Q Who sent in a selfie video. They're an early stage entrepreneur. We're going to listen to it, and then, uh, let's opine. Hey Alex, how does a startup get attractive benefit packages at competitive rates before they hit a large group head count? Okay, Jesse, you said, um, off cam that you've dealt with this recently, so how do you think about benefits in the early stages of a business?

A Yeah. I mean, a couple of interesting things, you know, there's certain state laws that are different for different places. So one cool thing about California is they have to, they force you or whatever they provide for, you get the same benefits as any small business of a certain size. And that's actually a requirement from the insurers. So if you're starting in California, that's a benefit in Missouri. That's not the case. I don't know what the case is in New York. When we first started, we just did normal insurance as a small business. Cause we were starting in California and that worked this time around. We've, You know, and we looked at PEOs and what PEOs are, I don't even know what it stands for, but they essentially take your employees onto them as, as if they're their employees. The famous one is Trinet. It's like a big publicly traded company. And they, by aggregating a bunch of small businesses, they basically can negotiate and get as good of benefits as a big company. Now the process at Trinet used to be a total disaster. They had to like, they were on their payroll. They legally weren't your employees. They sent the paycheck and they were employees. It was like this really messy things. I never did it before, but now these newer companies like Gusto and Rippling have made it basically seamless and made like totally like a white label. It's like employees don't even …

AI assessment note: “by aggregating a bunch of small businesses, they basically can negotiate and get as good”

Q book. Like a lot of people are doing this now. And he's like, I have no idea what I'm going to write about. And they were like, just look at what your most trafficked article is ever. So I think just to me, an interesting lesson there is how do you just keep sizing the bet with time or money more and more as you get some level of signal?

A I think the whole back to the newsletter thing, like I, I, every time an entrepreneur says I have this idea for a B to C thing of blah, blah, blah. I'm always just like, cool. Why don't you start a newsletter around it? The, you'll learn your customer better. You'll have some basis to launch something off of you'll validate whether or not people care about this issue or not. The other thing I like about it, by the way, is, and I don't say this, but I'll say it here is it's going to prove to you how hard shit is. Cause getting a newsletter, getting a, uh, 10,000 people to sign up for a newsletter about whatever you think is a really big problem they have in the world and topic. If they, if they weren't going to sign up for that, you'll see how hard it is to get Twitter people out there and, you know, and Twitter signing up. You'll see how hard it is to get people who they're going to unsubscribe from your thing. So it actually puts you through the ringer, especially for first time entrepreneurs who haven't experienced like how challenging the stuff can actually be to get going. And that's the other reason I love it. I think my favorite one for B to B businesses is like make a 10, 15 slide deck. And set up 10, 10 to 20 meetings and pitch it. Pitch the thing, sell it, and see if anybody wants to buy it. And even if at the end of the call, they go, yeah, I'm in. You go, okay, cool.…

AI assessment note: “Why don't you start a newsletter around it? The, you'll learn your customer better.”

Q founders who are listening to this are wondering is like, how do you know when is the right time to sell? So it seems like in the context of your business, John, who was the CEO of the business, like, He was ready for, for a change. It was that the primary driver for why you guys were looking to sell and push? Was there anything else contributing to it?

A Yeah, I think it's a great question. I mean, you know, in, in, in, in, I, I think what I will say is I think most founders undervalue how important it is that they, it's a personal, it's such a personal choice. So in the case of John, I mean, John was like, Hey guys, you know, we're going to sell this business or, or I might, you know, I need to, I need to change the scenery one way or the other sort of, right. That was kind of, and we're, we're best buddies and trust. So that it wasn't like he was going to surprise us with anything, but he was also raising a flag going, guys, I'm, And that was the CEO version, professional CEO version of the founder version, which maybe happened to me in 2015, 16, which was like, I've worked really, really hard for a long time and I'm ready for something different. And I think like way too many founders who are great tacticians and try to get the answer right all the time, go, what's the right time? Is it optimized? Is the valuation optimized? All these other things optimized. And you, with enough years under your belt, you realize that stuff is far less important than am I ready? And is it the right thing for the people in the company? And so I think in our case, it was Everybody was ready. You know, like it's, if it was going to be the holdco, we would have probably owned it for a really long time, but now that it wasn't, it no longer made s…

AI assessment note: “most founders undervalue how important it is that they, it's a personal”

Q Was it, uh, was it Ampush bought it? Got it.

A Yeah. Ampush bought it. And, uh, the, her story was in 2012, she got obsessed with Birchbox and all these subscriptions. She just started writing about them online and, you know, just purely passion. I'm going to write about this category. I love this. I'm going to order them on a review them. And like everything like that, it started to snowball. Other people who love them started following her. To the point where she had a multimillion dollar EBITDA business, but it started as a side hustle. Um, and so I, I think like pick a category again that you, that you love, that you know of, and just start writing about her or, or some way contribute to content. I think you could totally do it on the side, but then it gets the scale of media over time.

AI assessment note: “Yeah. Ampush bought it.”

Q And so for me, I think I saw her tweet something exactly along the lines of this idea of like, how do I deal with imposter syndrome as a first time CEO?

A Yeah. People flipping, you know, I need to know everything. I'm supposed to be the expert. And for me, I like when we started Connie, I was like, I don't know what verticals this is going to work for. I don't, in our pitch deck, by the way, raise money. It says our target market is one to Shopify stores. And then we started selling to them and realized, God, it's hard. The product isn't quite self-serve enough. And we closed a couple bigger guys. And it's like, these guys can leverage it. They have the team to use it. Like we needed a person inside the content. And so I didn't, we didn't know. Right. And, and so I think that's the most important thing is like, I don't know is a really powerful statement and phrase. And I was like, I don't know what the market's going to be. I I'm going to go learn. And I'm going to do the way I learned that I'm going to sell. I'm going to see who use it. The one thing I made, I made it sound like the customers just said that this is my problem. We had customers use the product, right? And the ones that have loved it have gone into those use cases. So it's not like there's people spending every day in Kahani and they're using it for those purposes, which told us that that's what the, you know, the problem was they were trying to solve. So it's just super important to, to be like, I didn't know. I don't know. I don't know. I had no idea. And then…

AI assessment note: “that's what's kept me calm because I don't expect myself to have the master plan”

Q And are you a crier? Like, do you cry often?

A No, not a huge one. Uh, but I do. Um, and no, it hit me. I mean, it hit me big time. And I think like, even the, it's a little surreal of it not being ours anymore. It's been such a big part of my life for so long. So it was like, kind of like feeling a little bit like feeling for your cell phone and it's not there anymore or whatever. Like there was that feeling of it just being a normal part of things. I'm still in a couple of the Slack joint channels. So I'm like, hi guys, I'm still here. Um, I said, I miss you then the other day on, there's like a business development channel. I was like, I miss you guys.

AI assessment note: “No, not a huge one. Uh, but I do.”

Q But how do you value that business? Going back to your point, like, how do you value this thing that doesn't have deposits anymore?

A I don't think, I think they get, they, you know, People get to keep their jobs and, and maybe some comp packages or whatever, like nobody makes any, like the shareholders are zero or near zero. Um, or like you just buy it for zero and then some shareholders will sue and they'll get settled. But like, I mean, that's like, you know, Bear Stearns was bought out for two dollars. Merrill Lynch, I think was given, right? Bank of America was like, eh, you better just give this to me because I'm not gonna, I'm not gonna take it otherwise. So, and that's like the crazy thing that it's kind of a funny, you know, financial institutions don't, They don't really make anything, you know, and so, and so they rely on trust and relationships and credibility and all these different things, and it is pretty sad when you zoom out. It's just kind of like how everyone turned on them, and even like as someone who kind of semi did that, right, like we took out what we could. It's, the challenging thing is it has nothing to do with them from my perspective. It's like, again, everyone else. It's just like one of these classic panicky situations where you're like, well, I don't want to be the person left holding the bag. Like, I don't want to be the, the boy scout here that Get screwed over by other, other people panicking, and so it just ended up being this situation, and it's just sad that it, that it …

AI assessment note: “the shareholders are zero or near zero. Um, or like you just buy it for zero”

Q Yeah. How old were you when you started? Do you remember the exact age?

A Well, here's a funny story. So the name Ampush, you know this, but the audience might not know this. It's, it's the first two letters of the founder's last name. So Chris Amos, Jesse Poogee, Nick Shaw, and our first company, we started sophomore year of college. We were super douchey and it was called Amos Poogee and Shaw Inc. It was like, and it was our t-shirt business. And You know, one day we were looking at the forms for it and Chris, I think came up with it. Chris looked at it and he goes, man, that spells ampush. And they're like, immediately we jump on Google. Like, is that domain available? Uh, and it was available. So we've owned the domain and I've kind of used that name for various things since 2004.

AI assessment note: “our first company, we started sophomore year of college.”

Q other people are doing it right now. And I figured, you know, it's not considered the sexiest topic, but I think it's probably one of the most important we'll talk about is, how do you go about goal setting? How do you go about planning? I know we, we all have thoughts on this, but just to kick it off, Jesse, how do you go about planning for your businesses?

A Yeah. Yeah. This is a topic I could talk about for a long time. You know, for the first few years, we didn't really do it. I mean, what we did, like me and Nick would sit and look at a spreadsheet and kind of drag the cells out and toy around with them a little bit and go, yeah, okay, that looks good. Let's do that. Which, which by the way is fine. I mean, it, you know, depending on where you're at and, and your business, I don't think that's a terrible way to plan and to think about your business. Over time, you know, we, we, we played with OKRs for many years and just, we struggled with them and I'm happy to talk more about that. And then we sort of started pulling together a variety of different systems that we sort of made our own, uh, which I'll talk a little bit about in a second, but, but we really started thinking about how do we do this ourselves? So, so I'll talk about the system a little bit before I say that, you know, one thing I tell every entrepreneur I work with is the best planning system is the system that you will use. That's also my philosophy on software, by the way, because a lot of people, and I made this mistake with OKRs for many years is like, it became this hugely administrative burden. Nobody, nobody ever touched No one used them. They, it would feel so annoying to everybody to do them every quarter, including me. And then we didn't really use them a…

AI assessment note: “the best planning system is the system that you will use.”

Q thought about this a lot, which is, what does it mean to CEO in a company? How does the role evolve over time? Um, and you know, what has it been like for us to be in positions, in CEO positions at various companies? So Jesse, I want to start with you. What does the CEO role mean to you, and how has that journey evolved for you over time?

A Yeah, there's a, there's a couple things, kind of, like, touchstones for me when I think about being the CEO. The first one is, you know, Ben Horowitz has the hard thing about hard things, and I think he has, these are all articles and stuff, but one of the things I tell every CEO I work with and myself is he says the curve, like, if you had, if you had a test, the curve is a 22 out of a hundred. That's the average. So if you grade yourself on a 90 out of a hundred, like, you know, normally getting an A is 90 out of a hundred, and usually people who choose to be CEOs are people who like A's. You're immediately, you know, you're going to feel like you're failing every day, which you kind of are. And that's just, but once you baseline that as the role, then it's like, oh, okay, this is a lot easier. I can, I can breathe. And you know, it's like, I always use the baseball analogy, right? Albert Pujols just finished up his big run and he's going to, I don't know, top 10 player ever. And he's two 96 batting average means he's out of a thousand things. He's at 296. Like he has not done well by the 90% standard, but he's crushed it for baseball standards. And I think So I think shifting the standard is super, super important from the get go. So that's one big one for me. I think the other one that I always talk about is like, especially for first time entrepreneurs, first time CEOs, w…

AI assessment note: “there's a couple things, kind of, like, touchstones for me when I think about being the CEO”

Q me, I, I'd asked you, like, what is all the shit that's gone on with your businesses in the last week? And you had a ton of great stuff. One of the things that stood out and was the first thing you mentioned was that you redid your weekly meetings for GoToMarket across Kahani and Growth Assistant. Talk about why you're doing that. Like, why did you rework these meetings?

A Yeah. Yeah. I think, I think the, you know, I'll start by saying the, the couple of things I was even hinting at earlier. I think one is, uh, you know, inertia is the devil of business. Right. And you think about the classic big company or the Google thing you were just mentioning, and it's like, oh, they've gotten slow and they've gotten reactive. And I was watching this thing recently where he was like, you know, once you become a big company, a hundred million in revenue, you just want to protect that revenue. And that's in some ways human, it's like the human tendency to, to protect, uh, But I would argue that kind of behavior happens a lot earlier than most people acknowledge. Like you get to a million in revenue. You're like, I don't want to go down from a million. I want to, you know, and so there's a human nature tendency. And this is kind of like what the whole innovators dilemma concept is. That book is talks about how, if you don't disrupt yourself, right? Like Polaroid is an example. Somebody else is going to disrupt you. And like, there's a classic example of Steve jobs where he was a huge fan of that book. And, and the iPod was crushing it and he disrupted the iPod with the iPhone. Like he actually cannibalized his own sales. And I bring that up at a high level to relate to it. Like that isn't just a big strategic thing you do at every level of your organization. …

AI assessment note: “anytime I see inertia seeping in and, and I will, I will, Blow it up.”

Q money for it. You just raised a seed round. My first question to you is, what the fuck? Two, what the fuck? One, one, what the fuck is you built a business. You exited it, uh, and you decided to go back into the arena, and I, maybe a questionable decision. I'd love to hear why. Second is you went to the dark side, and you raised VC money. Why?

A Yeah. Yeah. What a cool, what a, what a great set of what the fucks. So, you know, my story, I, I grew up in a, my immigrant household, born and raised in St. Louis very proudly. Uh, and I was away for 18 years and I actually just moved back. So I'm, I'm St. Louis for life. Uh, you know, I was starting the business, businesses when I was 1012, I had a DJing company, a t-shirt business in college, just was always the kid hustling and trying to build something and then spend some time in the more standard jobs of consulting and then on the finance world. But 2010 left and started my first company Ampush, which was totally bootstrapped. We were one of the first companies to crack the code on Facebook marketing and advertising. Our early customers were Uber, Dollar Shave Club, Peloton. We grew that business, um, had a liquidity event in 20, late 2015. And I continue to run it, actually. I met these guys from Red Ventures and learned a ton from them, basically through, for a full decade. So I ran it for 10 years. And to answer your question, Alex, like, you know, as I went down that process, I realized, I started trying to pull out what was driving me every day, because it wasn't money anymore, and it wasn't, you know, ambition solely. I loved, I loved helping people learn and grow, and I loved building businesses. And so I wanted to build something that would make me, help me do th…

AI assessment note: “I loved helping people learn and grow, and I loved building businesses.”

Q Okay. Let's hear one from you. Do you have any predictions for the year?

A Yeah, you know, the theme, one of the themes I have, I do a lot of bottom-up stuff at GatewayX, but then we'll, we quickly see top-down, um, you know, I think one of the big things is, I'd say in the short term, there will be a shakeout in the creator economy, um, but again, in the long term, I think that category of people and workers is going to continue to kind of grow and explode. I think similar to all the rest of the economy, it's been overbuilt, um, For what the demand is going to be now. It's going to pull back. There's going to be a flight to quality, but in the medium run, let's say two to three years, it's going to keep being a critical workforce. And I think there's a huge opportunity. One of our lists of ideas and items is selling, creating services for that category because they fall into this neither here nor there. Uh, I have a really good idea that I won't share, but like, just imagine that these aren't fully employees. They're not Fully contract employees. They're not fully businesses, so they don't check any of the current boxes for all the various products. Payroll runs. Um, one of the, one of the juiciest private equity businesses out there, I don't know if I've told you about this, maybe offline I've told you, is like, is like rights management for Hollywood people.

AI assessment note: “in the short term, there will be a shakeout in the creator economy”

Q much shit about it. Um, he's like, I can't remember what he said exactly, but basically he was like, you know, you're setting a horrible example by wearing shorts to the office, and I was like, in my head, maybe I got a little defensive. I was like, But I don't give a shit if other people wear shorts to the office. What, what's your view on like employee garb?

A Yeah, I think, well, let me start by saying, like, the reason I actually do take the time to properly put a turban on and, and, you know, make my beard look tidy, it's like a 45 minute process, and especially on something public, like, one of the tenets of Sikhism, the religion, is actually to maintain the identity, almost like a uniform you don't take off, so that you are representing your people and, you know, God and holiness and all that stuff, and so I do actually take it pretty seriously. Uh, especially in this kind of a venue. Like, this is a show, and it's gonna be on YouTube and stuff. So, it is interesting, cuz I'm like, yeah, it's still tough to, like, be here. This is not, you know, it's not not representing, but it's not fully representing.

AI assessment note: “let me start by saying, like, the reason I actually do take the time”

Q And he loved the first game, right? Like, didn't he have an amazing time?

A Yeah, the first game, he had this great time. We took him out early. He was upset that we had to leave the third period. You know, his sister was there. We didn't want them to get not asleep last night. We said, you stay until, until it's over. He got home at 1030, which is really late. His bedtime's like eight. He had a blast, you know, and, and like that motivate, like, I don't know, I'm motivated to like give him unique life experiences, and so, yeah, I think, I think my pure drive to be really successful and make a lot of money is definitely different than when I was 25, um, but I, I don't know that I'm less ambitious. I'm like more ambitious for a balanced life, if that makes sense, like a holistic experience and all those different aspects of it. I think to answer the question, I mean, look, it's hard for me. I, I, I kind of think I knew I wanted to be an entrepreneur by the time I was 12, which, cause my dad was an entrepreneur, so I had this, like, unfair cheat code of seeing someone in that position, and started my first real company at 25, which I think with kids and, you know, uh, would have been really hard. Like, we worked hard. We had no idea what we were doing, and I don't know, other than if you've been really, like, experienced in a business or maybe early on in another business, I don't know how you learn that, but maybe you do. Maybe at 55, you were the The f…

AI assessment note: “Yeah, the first game, he had this great time.”