The Exchanges

Q about what to pay yourself? Like, how, how do you think through, basically, you know, you have to tell an investor use of funds. You, like, know you need to take care of your lifestyle so you're not, like, stressed about that every day versus building your business, but also you don't want to come off as, like, greedy and living a bougie lifestyle. How do you find the balance?

A Yeah, it's tough for sure because I think a lot of people are trained to want to, like, almost show off the fact that they're not taking a huge salary because it's, like, I'm investing all my time, all the money into the business. At the end of the day, it's like an opportunity cost like anything else. Like, you know, your balance sheet, you know how much you can get by to live like a normal life, and how much you need to have available in the business to invest in, hiring other employees, infrastructure, whatever it is to take your business to the next level. And so what I don't believe in at all is like, hey, pay yourself nothing and really prove like you're some harder that can live off like 25,000 dollars a month. Because at the end of the day, like as an entrepreneur, You want to make sure that all of your focus and attention are focused on the business and not how are you going to pay rent? How are you, like, you don't want to do X, Y, Z because you don't have enough capital to do so. I think there's something to be said about, like, 99% of my worries are all business focused in life, which could also be a problem, but totally different conversation. But, like, financial is not one of them, so I don't have to worry about, like, should I take, I know some entrepreneurs that actually get into, like, kind of pivoting their business to do consulting as well. And they kind of …

AI assessment note: “know how much you can get by to live like a normal life”

Q pushing yourself? Do you have a sense of it's extrinsic at all? Like you just want to be rich as fuck, or you want to, you know, prove to someone who wronged you in the past, or like there's some chip on your shoulder because of an experience you had. Like, how, how do you think about what are kind of the, the few things that contribute to motivating you?

A Yeah, it's probably all of the above, right? So I am intrinsically motivated because there's so many things I want to do and accomplish. And I think having a successful company, having access to capital, being financially free gives you a lot of opportunities to pursue things that you're passionate about. And I want to do so many different things in my life where I feel like this is like a great way to be on the path to be able to accomplish those different things. There is extrinsic in terms of like money is great. Obviously there's advantageous things about building a successful company and the doors that opens in terms of like personal social life. There is just the competitive nature of, I find like one of the books I loved way back when it was like Mark Cuban's book on like the sport of business, but like I grew up playing sports from basketball, soccer, whatever. And the fact that business is so competitive, And, like, there are winners, there's losers. Like, you can outwork someone, you can outthink someone, you can outstrategize people. I think it's just something that I've always been extremely hyper-competitive and wanting to be the best at what I do. And, at the end of the day, business is, like, real numbers. Like, there's a scoreboard, and if there's a way that we can build one of the most successful companies in our industry, I think it's, like, a very fun challen…

AI assessment note: “Yeah, it's probably all of the above, right? So I am intrinsically motivated”

Q that has enabled the business to grow as well. First one is how do you think you have changed as a founder, um, from let's call it like when you last co-founded a business, which was VentureStorm to now. Um, what do you think is different about just like the way your, your brain thinks or, um, how you're running this business that is setting everything up for more success?

A I think as a founder, you have to be very good at protecting your time and prioritizing. I think early days, both in my career and starting the business, anytime someone somewhat interesting wanted to talk to me, I thought that was the coolest thing. I was like, of course, I'll take a 30 minute call. And like, maybe there's some world where we can help each other out or you can provide value. Um, what has changed a lot is I say no to like 95% of things. You asked earlier about like this podcast that I've been on a decent amount of podcasts. I actually say no to probably 90% of podcasts. The ones I say yes to are either because they have a large audience. I think the halo effect of being able to tell my story and communicate and get in front of net new people could lead to more business. So strategic and audience size, or a lot of times are like beehive users and just like going through the narrative of being to support our own users. I'll go on the podcast to support them. But I don't know if one of the things that I do, I feel like somewhat unconventional is a lot of investors reach out as we've had more and more success of Hey, would love to develop the relationship. Like, let's get 30 minutes on the calendar. Decently, big name investors. And I relentlessly just go, we're heads down building right now. If I said yes to every meeting that came across my plate, then no one wou…

AI assessment note: “What has changed a lot is I say no to like 95% of things.”

Q while also building really scalable backend tech. Like, it just sounds very, very difficult while you're also competing against much larger, better funded tech companies. Is there any kind of, like, Method to the madness on how you've gone about recruiting that's either different or something you haven't seen companies do, or you just like the world's best, uh, salesperson for engineers. Like what, what's allowed you to do that?

A Definitely not the world's best. I'd say it took us, I mean, we're constantly looking for top talented engineers. It's taken us two years to get the 12 engineers that we have. And so it, I mean, we, and I, I owe a ton of credit to our early engineering team. There were times where I was like, hey, we need to move faster. We need to hire engineers. Here's someone who I think is good enough. And they always push back being like, I don't think they're the perfect fit for X, Y, Z reason. To which me as like the CEO trying to push out features and promise all these things to our users that are coming, but they're not coming because we don't have enough bandwidth to build them, would always get super frustrated. Like, don't you think this person's good enough to hire? And they were pretty relentless in being like, it's just such a efficiency and bandwidth drag to have Quote, unquote, lower quality engineers bring down the bandwidth of the team because that requires other engineers to clean up their code or, like, have to review it even, like, more thoroughly. And so, yes, it sounds like we do have a bunch of unicorns in our team, and they're great, but it took us two years of, like, slowly adding one engineer a quarter to find it.

AI assessment note: “I owe a ton of credit to our early engineering team”

Q like product. How do you like, how do you maintain such a rapid product cadence? And is there actually like, are there milestones you set for how often you want to be, uh, improving features to be able to announce them to the world? And then is there like a marketing blitz package that you have every time you do one of these? Talk about that a little bit more.

A Yeah, I'd say a few things. So on the product side, we have a quarterly roadmap that I set aside every quarter. So at the end of Q two, we're preparing the Q three roadmap. It's high level, what I call epics, which are tenfold features that do not currently exist, or initiatives of making one feature 10 times better by doing X, Y, Z. So I'd say we have about 80% of the roadmap mapped out of exactly what we want to build in the upcoming quarter. Which is then broken down like the smaller pieces of in order to launch feature X, we have to do feature Y first because it unblocks this. And then I'd say we leave about like 15 to 20% open for feedback where whether it's Twitter, LinkedIn, or users writing into support, there's constantly different use cases that we are understanding that we need to improve on. And it's been our core advantage going back to what we were just talking about to be able to listen to users, make them feel heard, and prioritize what they want us to build. And so I'd say it's about eighty-twenty pre-built each quarter and 20% listening to feedback and building there. In terms of, like, the hype cycle, that, again, came from, like, very early days. We had four engineers and, like, the only thing we could do was ship product. And a lot of it actually comes from the insecurity of day one, we had the least features of any given product. So how do you take a user …

AI assessment note: “we have about 80% of the roadmap mapped out of exactly what we want”

Q picture because you're selling Basically the investor on the future and why they trust you to attain that future, but then you start talking about whether it's series A, series B, and I think at least the story that people have in their heads is this is where metrics start mattering more. This is where financials matter more. How do you see the startup pitch evolving as your business evolves?

A It does evolve, and that is one of the traps that many founders fall into is they rely on the story that got them there and thinking that it's still going to work at the Later stages. And the reality is it doesn't. It's just like you as a person grow, you evolve, and the same should be true for a story. At the beginning stages, right, the pre-seed seed, you don't have a ton of metrics, but you still have some metrics. You need to be able to use data to back up the world that you're talking about. And that really comes down to understanding how to frame numbers correctly. I always say this numbers on their own are meaningless. I can make numbers say good or bad, no matter what. And this, you know, comes back from my background as a trial lawyer. In every case I tried, the facts were the same, but the way the prosecution me positioned, it was very different from how the defense positioned it. The facts were still the same, just like the numbers are the same. Numbers mean what we say they mean. So even at the early stages, you need to have some numbers, but they're going to be more about the opportunity size. Right. Whereas the numbers you're talking about in later stage is going to be the numbers of your business. It's going to be all those metrics that we're talking about, right? LTV, ACV, CAC, all the things that you've got to be able to explain and say, Hey, this is why we see…

AI assessment note: “It does evolve, and that is one of the traps that many founders fall into”

Q Yeah, man, I love that. Um, okay, so let's talk, you talked about what, A good pitch and a good story, uh, irrespective of stage looks like. Let's talk about some of the biggest mistakes you've seen. When, when founders really botch pitches, what are the most common things you're seeing in what they're saying or what they're sharing?

A A couple things. One is a lot of founders make the mistake of not sharing anything about who they are as a, both as a person and as a founder, which I think is One of the biggest mistakes that we see, a lot of founders think that investors only care about like the business side of a founder, and the reality is I want to know also the things about who you are as a person. Investors want to know that. We can learn a lot about someone if they were a competitive gamer growing up. We can learn a lot about someone if they did debate. We can learn a lot about someone if they're an immigrant and they speak five languages. Like we can learn a lot about Whether or not they're going to succeed based on who they are as a person, even if it's not directly business related. So I think a lot of founders make the mistake of thinking investors don't care about anything about who I am. I just want to focus on business. And what that does is it puts the investor into the logical brain side because all it is now is a business transaction and a business transaction is going to be much harder to prove because they're seeing so many business transactions and business transactions. You look for red flags. When we like somebody, when we believe in them, when we connect to them, we look for green flags. We look for reasons to say yes. That's just human nature. And so that, that's kind of piece one. Piec…

AI assessment note: “One is a lot of founders make the mistake of not sharing anything about who they are”

Q a lot of, kind of, introverts or people who are more reserved in nature worry about, like, is there one way to tell a story well, and it's very, like, you know, it feels like, you know, a better version of the used car salesman. What would you say to people who are more reserved or introverted in nature and how they can still be really good storytellers and pitchers?

A I've worked with a lot of founders. I mean, you know this, the founders I've worked with, we've raised six hundred million dollars so far in capital, and I'm gonna tell you right now, not a single one of them looks the same. They all Communicate very differently. Some are very charismatic. It's effortless for them to carry on a conversation. Others are like way on, on the end of the spectrum, super technical, don't like talking to people. But what we do is we lean into those strengths. So we just create the, the training ground and we help them understand like, what is an investor looking for? So that they understand the process, whether they're extroverted, introverted, anywhere on that spectrum, what's an investor looking for and how can you show up in that way to deliver it to them? And so the technical founders tend to be much more like they kind of follow a, a program out in their head. They know that if they say this, then I say this, if they say this, then I say this. And it's like, that's great. Do that for the ones who are more comfortable and at ease and flow. We're like, Hey, just kind of like carry on a conversation. See where it goes. Don't be afraid to go down rabbit trails. Like you have that level of mastery of communication. Great. We do that with them. And the ones in between were like, Hey, let's kind of blend. Let's blend these two. So like on certain topics…

AI assessment note: “what we do is we lean into those strengths. So we just create the training ground”

Q basically every row is a different CEO of a venture backed or fortune, 500 business. And then basically every column was a bucket of how they spend their time and what percentage of their time they spend on it, like an aggregating calendar of everyone. What are the buckets that you spend your time on today? And what is the percentage of time spent on each of those buckets roughly?

A Yeah. And I think it's shifted. So let's talk about today. Right now we're in planning phase. So right now it's reiterating kind of the vision of what we're trying to do and letting teams kind of, uh, gather and talk about the great ideas and, and kind of cultivate those ideas and bring them up and help us think about our roadmap. So right now probably it's like. 20, 30% vision setting and reiterating vision setting, like all the time, you gotta say that, you know, I had this one CEO of my last company, his moniker was Tell them what you're going to tell them, tell them, tell them what you told them. And he just did that again and again and again. So I think that's like 20 to 30% of the time. I think recruiting is a big deal. Like we are a business that are pretty healthy. So we're, you know, over a hundred million dollars an hour. We're profitable, but we're really strategic about the way we build the business. And so now we're getting into the phase of how do we get the right executives into the company and make sure they're set up for time. So that's probably 20 to 30% of time. So I don't know, that's like fifty-ish percent of my time. Um, the last, the, the kind of one piece is culture setting a lot of the degree, and we have a lot of work to do here because-

AI assessment note: “So right now probably it's like. 20, 30% vision setting”

Q And out of curiosity for that, uh, last example you use, um, do you know, how, how does she make her money on the platform? Is it, is it through like, Paid subscription. Is it a premium podcast? What is it?

A Yeah. So the way she does it is, um, majority of her revenue comes from courses, right? But it's, it's a very, she's very thoughtful person. Like she knows marketing well, and she knows her brand very well too. So she's an ex neonatal nurse. And so what she ends up doing is she's like, you know, kids are like this recurring dynamic society, obviously, which is great. Like people have kids all the time and her audience keeps getting replenished. It keeps getting replenished. And a lot of it is like, Hey, you should check out. It's like a referral. So you should check out this website, follow this person on social media. And all of a sudden when people are pregnant, they're thinking about, ah, this is going to be hell. How do I get ready for this? And when it's time, they're aware of her cause she's able to build this funnel. And then, yeah, when she wants to actually monetize, she brings into her website and they, they get educated on what the content is and they pick a package, uh, one course, several courses. She kind of merchandises it however she wants cause she controls it. And then all that revenue goes right to her and it's a digital business. So it's even different than like a Shopify business. Cause the margins here are like crazy astronomical, right? So it's really, really cool way to build businesses and even augment, uh, e-commerce businesses with this kind of like t…

AI assessment note: “majority of her revenue comes from courses, right?”

Q And while, you know, anything can happen, it seems like the odds of a recession are lower or full blown recession and something closer to a soft landing is much more likely. But I told you I wanted to revisit the concept of a recession for investors. So the million dollar question is, As a retail investor, how should I be thinking about investing into a recession? Should one happen?

A That's a great question, and it's one that I've fielded many, many times in recent months, and people ask, you know, give me, give me a recession portfolio. What is, how, how do we invest recession proof? And the problem is that recessions are, you know, we know the yield curve is very inverted, and it has been inverted for a long time, so short-term rates are well above long-term rates, and they've been that way for almost a year. And we know historically that that yield curve signal has been very accurate in terms of forecasting a recession. So by that measure, we should get a recession maybe in 2024. The problem is that the lead times between the inversion of the curve and the eventual recession is all over the place. It can be as little as six months. It can be as long as two years. It doesn't really tell you how severe the recession will be. How long it lasts, and so my answer is always, you know, in order to trade the recession playbook, uh, you have to market time, and I can tell you, I've been in the business almost four decades, and I, I can't do it, like, you know, and I have all the resources, you know, at my disposal to try to do it, and it's just a really tough game, because you need to know four things in order to trade around a recession. You need to know when it starts, you You need to know how long it lasts, how bad it's going to be, and even if you know all of…

AI assessment note: “in order to trade the recession playbook, uh, you have to market time”

Q take further, there are never thoughts that it could fall through and be a waste of your valuable time and potential resources? It's kind of a long question. Or, If an idea has gone this far conceptually, is it always the case of trying it to at least attempt to find market fit and learn what the customers truly want? Said simply, how do you test a new business idea?

A Yeah, I take this as like, how do you test a new business idea and how do you think about whether to increase the amount of time you spend on your business idea? So the way that I think about this is the time that you spend on a business Looks more like a staircase rather than an escalator, meaning if a business goes well, you will hit certain milestones that cause your baseline of mental and physical involvement to move up stepwise versus linearly, and so I kind of jotted down what I believe those milestones are roughly. First milestone is I'm experiencing or I identified a problem, and maybe I look into that problem more, but more likely I don't because most people Don't pursue a business idea the first time they experience a problem. What ends up happening is you hit the second milestone, which is my brain thinks about this problem for the 10th time. I can't shake my interest in solving it, so I start learning more. I talk to friends about the problem. I do research on Reddit and Quora and Twitter about the problem. I Google other businesses solving this problem because 80% of the time, there's already someone who is solving this problem, and the question becomes, are the people out there solving the problem in the way you want it to be solved? The next milestone is, I think there's a way to solve the problem better than how it's being solved, so now I want to run a test to …

AI assessment note: “time that you spend on a business Looks more like a staircase rather than an escalator”

Q Both examples seem to rely heavily on years or decades of experience slash success. Can you imagine a version of your agency being built by someone that hasn't already acquired the high quality talent and has a large network that you have?

A So it's a great question by Tanner P and Brian B. The short answer is yes. Like, I think there are some businesses that not anyone who is interested in building a business can build. Like when I think about Brett Adcock, who I interviewed, and he's building a deep hardware and software company, right? He's, like, literally creating humanoid robots. He wants to have a million of these humanoid robots by, I can't remember what year, like, by twenty-thirty or something. Like, no, not anyone can build that business, because there's such a cross-disciplinary wealth of knowledge you need. Like, you, you need to basically be able to go, like, not just an inch Deep and a mile wide or an inch wide and a mile deep. You have to literally be able to go like a mile deep, a mile wide. And so I think there are just certain people in the world, a very select few that are built to build that type of business. But for something like a service business or like the ghostwriting agency, I really believe that this is actually a great entry business for entrepreneurs because it doesn't require a lot of cash up front. It's an agency. So you can find Your first client, and then go source someone you need to pay to service your client once you have the client in mind. Like, basically, your job, your only job that exists with this business, if you don't have a built-in network, is one person. You just ne…

AI assessment note: “The short answer is yes... for something like a service business or like the ghostwriting agency”

Q there are a lot of assumptions that the industry is making that aren't necessarily the right assumptions. And because they're making those assumptions, they don't believe kind of what you're doing or the, the ability to get robots to perform human life tasks to be possible. What are a few, like what you would consider like big dangerous assumptions that the industry has made that you believe to be incorrect?

A Right off the bat. I think one is, there's this assumption that, I guess this is a debate on, should we build a humanoid that can do a lot of different things, meaning like one product can be put in to do thousands or not, if not millions of applications, or should we look at a problem, say like, um, a problem in a warehouse, a problem in retail, and just build a special purpose, like our special built robot. And I think most of the world, given how hard humanoids have been development-wise, feels like the world should be all purpose-built robots everywhere. And I think the assumption there is, is pretty flawed. I think it's really hard to build any robotic company, whatever you're doing, robotic vacuum or humanoid. It's just hard. You know, like a lot of people, a lot of capital, you need years, you need, uh, to develop a lot of, like, basically a continuum of product iterations that are getting better and better. And then, um, and then the problem there is you're building one product for one application. That application will never be done. A product will never be manufactured in high volumes, which is hard for cost. And you're never really going to build an AI data engine on one product. So you, you really want a general, you really want the generalizability of a product, like an interface here in robotics. You really want an application or a robot that can do many applicati…

AI assessment note: “feels like the world should be all purpose-built robots everywhere. And I think the assumption”

Q guide on what's actually priority for the founder versus what they talk about. If, I don't know if you have your calendar in front of you right now, but like, if you looked at your calendar today or tomorrow and you have to describe to me, like, what are you actually spending your time on? Like, I'd be super interested in like, what are you actually doing today and tomorrow?

A Yeah. So we start every day and we end every day with a standup on the engineering side next to the robot. And so we're, we're trying to So our, our one year anniversary is coming up for the business. We're going to try to walk the robot before that, which has never been done. That's basically one, like less than a year, uh, getting basically the, the whole team together, getting the vision for the company, like getting the funding for it, like building the product to a point where we're demonstrating a full humanoid system doing walking. It'd be the fastest I think I've ever heard of in the world. And so we do a stand up in the mornings on the engineering side. We have a detailed list of everything we need to do. Over basically like three big milestones. So it was basically getting upper body set up, brought up, lower body set up, first walking, and then we got some manipulation goals as we progress. And we, we end and begin every day with that stand up, talking about the problems, how to fix them. Do we change strategy? Do we bring up this test hand first or whatever it looks like? And that's a, I'm there. All my leads are there. The whole company's over there. Uh, and we're about to kick that off here in a minute. Um, and then throughout the day, all my meetings are product and engineering related. As I've As I've gotten like more mature in my career, I've realized more and …

AI assessment note: “we start every day and we end every day with a standup on the engineering side”

Q So how long were you running that business before you ended up working on something else or stopping working on the agency?

A So, you know, football ended for me and like my last game was Rose bowl, and I had already kind of done that homework assignment and rolled into the company. And so I really figured that company out in 2010. Like it took a couple of years, a lot of like mistakes. And I focused hard on that company for about two years. And we started to scale. We're making money. It was the first time that I was ever making money. And I was like, well, this is super cool, but it was a service business. And what that means is there's only 24 hours in the day, right? To provide service. And if you're not working, you're not earning. And I was, I just felt that pressure and, and I knew I had to come up with a new idea. So it took me from 2008 to 2012, but really I didn't graduate till 2010. So I was like in it hardcore for a couple years. And then I had, I knew I had to come up with a new idea for something that could be a product based business.

AI assessment note: “it took me from 2008 to 2012, but really I didn't graduate till 2010.”

Q say is it feels like a loss of some sort. Like, you know, the only similar comparison I have is stepping out of the CEO role from morning brew and it feeling like this, this void of like, who am I? What is my identity? Who is Alex Lieberman outside of building this business Morning Brew for the last eight years? Was it a similar experience for you in sport?

A Yeah, I mean, you know, growing up, you sacrifice everything to be a great athlete, right? You're not going to parties. You're not going on vacations. In college, you have people traveling abroad, or they're doing interesting things, and you're solely focused on this one thing, right? It's just like entrepreneurship. You start a company, it's your obsession, it's your identity, and you'll hear people tell you, like, Oh, like, don't make this your identity, right? But it's like, yeah, that's nice, but that's not the reality. Like, this is who I am. And when you lose that, all of a sudden, it feels like you have no purpose. You feel lost. You don't know what else to do or what to do next. Like, imagine playing a sport from the time you're six years old until you're 22, and that was the sole thing you're focused on, right? And then all of a sudden it's like, oh, no, sorry, you're done. Figure something else out.

AI assessment note: “when you lose that, all of a sudden, it feels like you have no purpose.”

Q Totally. So, so that's, that's the ad. So you have subscription based, 10% of your content sits there. Then the rest of your content is free, monetized with ads. And then what's the third bucket?

A The third bucket of the business is this ministry SaaS or pastor SaaS business. And, and really that's this core of the business that we're building for pastors. It's the original thesis of, Hey, we're trying to build all these tools for pastors so that they can build a digital church, right? They have their physical church, their analog church that you go to, but what about their digital church? Because For 2000 years, physical church has been great. COVID-nineteen physical church doesn't work anymore. We need a digital church. Same as movie theater to Netflix, right? So this pastor SaaS business or this ministry SaaS business is our third pillar where we build them all kinds of tools so that they can build their own digital church.

AI assessment note: “The third bucket of the business is this ministry SaaS or pastor SaaS business.”

Q Right. Do you internalize it, or do you just not feel it? Do you know?

A I'm not sure if I Feel it, but like it so quickly gets put into my subconscious that I don't have the consciousness to be aware of it, or if I literally don't feel it. Um, and so yeah, it's something, you know, I, I haven't seen a therapist in a while because it's one of those things where it's so easy to go to therapy when something's wrong, but when things are like fine, you end up getting out of the habit, and that's like the mode I'm in right now, but this is When I was last with my therapist, like, this is something we spoke about all the time, was like, how can I start getting more in touch with having an awareness of, like, what I'm actually feeling? And one of the things she always told me to do is, like, when I was feeling any emotion, sit for a second, like, pause, stop what I'm doing, and spend, like, 30 seconds or a minute just describing to myself what I am feeling, because it builds up that muscle of awareness.

AI assessment note: “I'm not sure if I Feel it, but like it so quickly gets put”

Q I love it. And I have to ask about this just cause, uh, I'm kind of, you had a great hook in the type of business he's doing now. What, what's the deal with the space exploration business? Like what, what is he doing?

A So we, uh, there's two different things that he's now working on. And it's, you know, I think one of the things that you'll meet my sister and myself and my mom, my little brother. And I think the one philosophy that we have is you don't, you don't have to start a company trying to solve a problem, right? That should always be your starting point. And, you know, right now, What he's been working on is, how do we get things from, like, From you launch things into space. How do you now create that last mile solution to get us to the moon? Right. And so, uh, it's really quite exciting. You've got, think of like the internet in the original days, right? You had point fiber laid under the ocean to get, you know, data from London to New York. That was the most complicated, most expensive part of building this global internet. But then once you get the internet data to New York, How do you get it to every household? It's called the last mile solution. And then once you do that, you can build apps and software and websites and all of that. And so in the space race, you have people like Jeff Bezos and Elon Musk and these who are building the kind of infrastructure, right? The rockets to get from earth to orbit, which is the most expensive, most difficult part. Now what we're doing with Moon Express is saying, how do you create the last mile solution to get, you know, whether it's satell…

AI assessment note: “Now what we're doing with Moon Express is saying, how do you create the last mile solution”

Q What does that look like in the context of built?

A So BILT took, again, a model that we saw work in one space, I'd say, why can't we apply it to the space of housing, right? And so if you think about like the Marriott ecosystem, there's a ton of different hotel brands that they brought together under the one program so that you had enough scale and program kind of like volume, if you will, to make it valuable to the customer, right? Housing's a tricky one because you have essentially like a couple, call it You know, 20 or so large institutional owners and operators, and then a bunch of midsize and regional players and a bunch of longtail folks. And so to even get started in trying to make something work, you have to have access to bring together all of these big players and all these midsize players and get them all to agree that they're going to work under one rewards brand and umbrella together. Now, if you've ever met folks in the real estate industry, the idea of asking for Player X and player Y to work together was like challenge number one, right? And then you realize, okay, if I can get them together, and let's say you get apartment buildings together, there's still forty million people that live outside of these buildings. So how am I going to create it so that anybody can earn points on rent? And then it was, even if you could earn points on rent, it doesn't really matter as you can use the points for something valuabl…

AI assessment note: “get them all to agree that they're going to work under one rewards brand”

Q Do you, do you have any examples of that? Like, do you have any examples of like, basically whether it was with landlords or whether it was just like with anyone where there was something very clearly they didn't want to give on and you were able to structure things in a way where you were able to do a deal with them? Yeah.

A I mean, it, it honestly happens with, with all of these things. Right. And even you look at like, even how we worked with Wells Fargo. I mean, if you just talk to them at the earliest days about this model, it was a scary concept, a new category and all these other things. But if you actually just took a step back and say, wait a second, like, what are you actually worried about? And what's your concern? And what do you actually care about? You find that like all of this stuff All of the, like, usual, we don't launch new programs, we have our established programs, et cetera, was irrelevant if you took a step back and said it's not about the credit card partnership, it's about acquiring a next generation base of banking customers for Wells Fargo.

AI assessment note: “even how we worked with Wells Fargo.”

Q So recently, you guys introduced a second category of product, right? Like, you've gone into pens. Talk about the decision of when to introduce kind of a second product category. So like, how did you know it was the right time without losing focus or diluting your business? And why did you choose pens?

A So I think it's the right time when you, when you feel like you've reached a cap for your acquisition channel for your current category, and you should start anticipating that. I was talking earlier in the podcast that we're probably going to hit our cap sometime this year, right? Early next year. And I'm anticipating that. So that's why we're rolling out new product categories. We're doing pens. We're doing apparel soon. And we're also going to try like other experience, like limited drops and other categories just for fun. But if they work really well, we might do it as a real category. Um, I also think like we're at the size where it can't dilute our business because we, we have like people in the right places handling all the right priorities. Right. Um, I went into pens because pens are potentially a nine figure, nine figure category. Um, and that fixes like the small market size of the sword problem. The real play with the pens is they're actually an ad spend product. So I'm trying to like acquire a new acquisition channel for my customers.

AI assessment note: “I went into pens because pens are potentially a nine figure, nine figure category.”

Q last valuation I saw was a report of three billion. Like you have that win. And so I'm always fascinated when founders have a win. What is it that motivates them to do anything else? Right? So you've, you're now working on Athena, you're working on power set, like you're doing a lot of shit in your life. Like what is it that propels you forward after that first win?

A So I think two things. One, I don't feel like I've won. Uh, when, you know, you go back to what Marco and Sander and I were talking about when we started Thumbtack, our ambition was to be the Amazon of local services. And we made a lot of progress. We've got a big team now, raised lots of capital, but we're not there yet. And so, uh, there's a lot left to do at Thumbtack, but even if Thumbtack does reach its full potential and become the Amazon local services, I just always want to swing bigger. It's like, we've got one life to live and I want to start as many businesses as we can do as much as we can. And it's like, life is short. So, you know, swing for the fences.

AI assessment note: “One, I don't feel like I've won... I just always want to swing bigger.”

Q And so how'd you change that to self-love?

A Yeah. So the way that I've thought about it or reframed it is I'm open-minded and that actually is a huge benefit because it creates safety for others. People know when they talk to me that I'm not going to judge what they're going to say. I'm not going to say it's wrong up front. I'm going to try to think through with them and that I have the capability of taking bets once I'm informed and they're needed and I don't have to have a strong view on everything. And, and what I'll say is like, this plays into like a broader framework that I think of. That I think there's this kind of like x-axis and y-axis. I think there's a y-axis of you're either highly opinionated at the top or weakly opinionated at the bottom. And then the x-axis is on the far right, you're closed-minded, and on the far left, you're open-minded. And so I think most people fall into two of these, whatever you want to call quadrants. I can't remember geometry or math or whatever. Um, first, I think people are either very close-minded and strongly opinionated or open-minded and weakly opinionated. And my view is the sweet spot is kind of the old adage of strong opinions loosely held, but I think it's very hard to achieve. And I felt self-conscious that I sit in the open-minded, weakly opinionated quadrant.

AI assessment note: “the way that I've thought about it or reframed it is I'm open-minded”

Q and you won't do it for a long time. And I think you are the perfect person to talk to about this question because if people looked at you, they'd be like, This guy has been building a junk business for 34 years. There is no possible way he is passionate about junk. So what are you passionate about and how has that fire stayed lit for over three decades?

A It's an interesting question, Alex. So I am passionate about possibility. I don't know if it's in the frame, but there's a sign behind me from Walt Disney. It's a Walt Disney quote that says it's kind of fun to do the impossible. The more impossible something is, The harder I chase it to try and prove that it actually is possible. So the never ending challenge of building a business, And growing it to different cities, different countries, other brands. That's what keeps me fired up. Now it's interesting because I think most entrepreneurs and people in life think find your passion and commitment will follow. I actually write in my book WTF that I think it's the total opposite because from my experience, commit to something and the passion will follow. I've got a kid, uh, I've got three kids and my ten-year-old is into ski racing right now. Hardcore.

AI assessment note: “I am passionate about possibility... The never ending challenge of building a business”

Q skepticism of like, yeah, that's great. But like your, your company isn't your family. There's a big debate around is your company or family. People will say company is not your family and it's more like a team and you want the best athletes who can help you perform. So when, what do you say to people who hear, who feel skepticism around this idea of just hiring happy people?

A It works for us. I mean, who am I to say, yes, we have a track record of doing it. It doesn't mean it works for everybody, but here's a real life example. The early 2000, we had a CFO that we had hired all the experience in the world. One of the best CFOs you could ever find, at least in our city. Wrong fit. Wrong fit culturally, not a pleasant, smiley, optimistic person. Great at their job. Cared about people, but it was just, it was too prickly. It wasn't the right fit. And then years later, we learned we were better having someone greener, less experienced, who had the right culture and real deep care for their people and groom them, give them the runway to, to, to grow. And we've got the best CFO you can ever imagine today.

AI assessment note: “It works for us. I mean, who am I to say... here's a real life example”

Q This begs the question around, uh, just PR and earned media in general. I feel like it is such a, um, a hot topic because a lot of entrepreneurs, including myself, will say PR is a total waste of time and money for a long time in your business, but I'm interested to hear your perspective. Like, do you believe in PR and spending money on PR?

A So I don't know if I believe in spending money as much as I do spending time. So of course it costs money. We had six people in our PR department in the early days. So yes, that costs us money, but it was them picking up the phones and calling Oprah's and the likes to say, got a great story idea for you. We always have stories. And I think today more than ever, we live in the storytelling age. I mean, what makes Morning Brew so special? Stories. Stories about current events in the markets, what's going on in the world, what's going on in business. We want information, but we want entertainment, and I think PR is just getting out and telling your story in an outlet where things can spread. Um, it's, most people don't get it, and most entrepreneurs don't realize they actually have a story, but I have yet to meet an entrepreneur that doesn't have just a fascinating story when you start asking questions.

AI assessment note: “I don't know if I believe in spending money as much as I do spending time.”

Q it took, uh, I guess eight years to get to your first million in, um, annual revenue today. You do more than a million dollars in revenue per day. What were some of the most important decisions you made from a strategy perspective or from a process perspective that allowed you to grow to, you know, being a business that does well north of six hundred million dollars a year?

A It's a great question. So I think the, the first thing we figured out was clearly it's all about people. Find the right people. Treat them right. We then realized that if you find the right people and you take care of them, The people will take care of our customers. People often in businesses put the customer first and they say the customer is king and queen, the holy grail. No, your people are, in my opinion, take care of your people. They will take care of the customer. When you take care of the customer, the customer will take care of the growth of your brand, your profits, your opportunity, your reputation. So the way I looked at this, as I said, we got the people part, right? What about systems? You asked me earlier, you said we get to why franchising. I think the thing I love most about franchising, and I wanted to take Ray Kroc's McDonald's Brothers recipe of consistently executed with excellence on everything. It's just junk removal, it's just house painting, but if you have the step-by-step checklist of how people should do things, we inspect what we inspect, and we keep them delivering with excellence, systems make a difference. And so I want my brand to look, feel, and act the same in every city so that people know what to expect as a customer. So when people say like your team is just awesome, you can add whatever city, whatever franchise to that. And that's what I…

AI assessment note: “first thing we figured out was clearly it's all about people... What about systems?”

Q and they have so much to learn from you. And I, I would say so much to learn from the different parts of, you know, Cody's empire, the, the media business, uh, the investing side, The business building side. But for those who haven't heard your story, can you just give me kind of the quick and dirty around what your career trajectory has been and how you got here?

A Yeah, 30 seconds. Uh, long time financial person, did all the things, PhD, MBA, Goldman Sachs, traditional route, wanted to blow my brains out like you when I realized my life would be spent inside of a spreadsheet for the rest of my life if I stayed in finance, and so realized I was kind of becoming unemployable pretty quickly, so I went to become a partner at a private equity fund, and then I realized I didn't even like having partners. I wanted to kind of like do the thing all by myself, and so I started building, um, Up a media company right behind the back of having bought and invested in the, what I call boring businesses for quite a few years because I saw people doing it in private equity. And so, um, I didn't think that was cool. Actually, I used to never tell anybody that I own laundromats and car washes and landscaping companies. I thought it was pretty lame. And then I started explaining to a few people once COVID happened, like, ah, by the way, I own these things. And they thought it was really interesting. And then we've sort of paralleled that into now this big business where we talked to a Instead of, quote unquote, renters of both their time, employment, and et cetera.

AI assessment note: “PhD, MBA, Goldman Sachs, traditional route... went to become a partner at a private equity fund”