Masterclass: How to go from founder to CEO (without imploding)

28 Oct 2025 · 58 min

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In short

My First Million - Episode 759: Masterclass: How to go from Founder to CEO (Without Imploding)

Episode Overview In this episode, Sam Parr and Shaan Puri delve into the crucial transition from being a founder to becoming an effective CEO. They share insights from their experiences, the lessons they learned, and practical frameworks that can help new CEOs avoid common pitfalls. The discussion covers essential strategies for leadership and delegation, the psychology behind successful business growth, and frameworks for effective team management.

Key Points Discussed

  1. Leadership Growth and Business Success
  2. Personal Growth is Critical: The growth of a business is closely tied to the personal development of its CEO. The bottleneck in business often reflects the psychological barriers of the founder.
  3. Transitioning to Leadership: The shift from doing tasks to leading people begins usually around $3 million in revenue, where brute force tactics are no longer sufficient for scaling.
  1. Delegation vs. Abdication
  2. Abdicating Responsibilities: This refers to hiring someone, showing them how to perform a task, and then stepping back entirely, which often leads to poor outcomes.
  3. Proper Delegation: Effective delegation involves:
  4. Training: Clearly explaining tasks and expectations.
  5. Structured Follow-ups: Setting deadlines and check-ins to ensure accountability.
  6. The RACI Model: A framework that clarifies roles within a project:
  7. Responsible (R): Who is carrying out the task.
  8. Accountable (A): Who is ultimately accountable for the task's success.
  9. Consulted (C): Who needs to provide input.
  10. Informed (I): Who needs updates on progress.
  1. Communication and Accountability
  2. Hard Conversations: CEOs must learn to address issues early and communicate effectively.
  3. Feedback Mechanisms: Immediate, clear feedback (positive and negative) is vital to maintaining accountability and ensuring that team members understand expectations.
  1. Company Values and Culture
  2. Creating Values: Instead of defining values at the outset, consider allowing them to emerge organically through the company's culture.
  3. Living the Values: It’s essential for leaders to embody the company’s values actively; otherwise, they become meaningless.
  1. Common Mistakes in Leadership
  2. Founder Psychology: Founders often struggle with the realization that they are the root cause of both problems and solutions within their companies.
  3. Scaling Challenges: Many founders unintentionally contribute to stagnation by failing to grow and adapt their leadership style to meet the needs of a scaling business.
  1. Best Practices for Success
  2. Embrace Best Practices: Emphasizing the importance of structure, accountability, and continuous improvement can greatly enhance a company’s trajectory.
  3. Avoiding Complacency: Founders should avoid settling into a “good enough” mindset and strive for constant growth and innovation.

Insights and Takeaways

  • Reflect on Personal Growth: Business leaders should continually assess their psychological readiness and adaptability.
  • Prioritize Training and Communication: Effective delegation and strong communication can resolve many common issues within a team.
  • Adaptation is Key: Embracing change and being open to new strategies are crucial in transitioning from founder to CEO successfully.
  • Recognize the Importance of Culture: A strong company culture that aligns with core values can significantly influence performance and employee satisfaction.

Resources Mentioned

  • Download Shaan's CEO Masterclass Guide [here](https://clickhubspot.com/esd).
  • Explore Shaan’s weekly email updates at [Shaan Puri's website](https://www.shaanpuri.com).
  • Check out [Hampton](https://www.joinhampton.com/) and other resources provided by Sam Parr.

Conclusion The episode encapsulates vital lessons for new CEOs navigating the challenging waters of leadership and growth. Emphasizing the importance of personal development, delegation, accountability, and company culture lays a strong foundation for sustainable business success.

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Transcript

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0:00All right, today we're talking about something that is the brutal truth about startups, which is that your business success is completely dependent on your growth as a CEO. And so we're talking about from starting a company to getting to that first one to three million in revenue, what you need to be doing as a CEO. And then Sam was sharing, you know, basically examples of after three million and scaling up from three to the tens of millions to, you know, to get to a hundred million in revenue, how you have to make this brain shift. And what do you got to do as a CEO? Mistakes we've made, stuff that works for us, tactics, techniques, specific frameworks we're using.

0:33It's all in here.

0:42I was writing like journaling this morning. Can I tell you what I was writing about and tell me if you've ever experienced this way? Yeah, but you have to start with Dear Diary. So I was realizing, and tell me if you ever had this realization, that my company's growth is limited by my personal growth. My company can only grow as fast as I can grow as a leader. Have you ever experienced that? Yeah, I have a similar belief, which is like the bottleneck of any business is the psychology of the founder. That's kind of the way I've always said it. So it's not necessarily my growth, but my psychology is the limiting factor.

1:14Yeah, your business is basically a mirror of your strengths and weaknesses. And here's what happens is a lot of people, they don't realize that. I haven't realized it until recently because the early stages of a business, and I don't know where that would be, some number between the huge number of one in 20 million in revenue. Honestly, it probably starts at three million in revenue where you're out of the brute force stage. and it depends on your business, but something like a million a year in profit maybe where you're out of the brute force stage and what happens next is actually the hard part.

1:47The hard part is like, how do you scale as a leader? Because your job then becomes leading people, not actually doing. And so I was thinking of like where that shift is and the big shift or like not the shift, but what like tactics or strategy needs to change. And I was trying to list out what those were and let me explain if you agree with each of these. So the first one is abdicating versus delegating. So let me walk you through a scenario. Tell me if you've done this exact same thing. I hire someone or I get a freelancer and I sit down and I go, so, and they sit next to me on a chair and I'm looking at them and I go, all right, so here's what I do.

2:19I do this, this, this, and this. All right, great. There you go. Talk to me later and let me know how you've made this better. Have you done that? Yeah, yeah. You got this, right? Yeah, yeah. I got this. Cool. Your problem, not mine. I'm mentally relieved of duties. and you say, all right, next week, how did you improve it? Why aren't the numbers going up? It's been a month, man. Why aren't the numbers going up? What the hell? I showed you how to do this. Like that conversation I've had so many times in my life and I'm having to break it. I cannot do that anymore. And so the difference between the bottleneck that I'm having to grow is abdicating versus delegating.

2:58That's the huge thing. And the second one is having hard conversations. Can you just play it back of what is the good version of it? So the abdicating is basically you take the ball, you put it in somebody else's plate, you mentally relieve yourself of duty, and then the sort of like in your mind, what the blame of potential failure or issues lies with them. What is the – give me the definition of abdicate there. What's the problem with abdicate? Well, let me tell you the other way around. Let me tell you what the solution is, which is proper delegation. And so how do you properly delegate? You do, I actually have it written down here, this framework that I've been trying to learn, which is what, how, when, and motivation.

3:40And so what that basically means is training. So you explain what you expect of someone, you show them how to do it by training them, and then you give them very specific deadlines, and then you have scheduled follow-ups. And sometimes it takes months to properly train people. So a really easy example is with salespeople. So how do you train a salesperson? You watch their sales calls, and you sit down with them for two hours every single week, and you say, instead of saying this, try this next time and let's see what happens. Or you said this, oftentimes that doesn't get the solution or the answer you want because of X, Y, and Z.

4:11Do this instead. And here's a script I want you to follow. And then after you do that for three or four months and then you're going to start, they're going to start learning to be better than you. And they're going to be like, hey, by the way, you didn't think about this. I actually went this way this time and here's the better result that I got. So the opposite of abdicating is properly delegating, which includes training and communicating with clarity, which expectations. Yeah, have you ever used the RACI model? What's that? R-A-C-I. So one thing that happens in a company is that it's unclear who's got it.

4:42So imagine we're playing catch. I throw the ball, you know, if I threw the ball, you're the only one there. You better catch this ball. And whether you catch it or not, maybe that depends a little bit on your skill, but there's absolutely no doubt that you need to go after it and catch the ball. There's nobody else there to do it. Now you had a second person. what changes. I throw the same ball. I didn't say who it's for. I don't know if you're getting it. I don't know if I'm going to, I don't know if we're supposed to fight over it. I don't know if I'm supposed to just back off. And I don't know if we need to have a quick conversation about this.

5:12I don't really know what to do. Now add another person, add another person. And imagine once you get to seven people, what starts to happen in a company is that some people just have sharp elbows and they try to fight for it. Some people just don't want the ball to drop. And they're sitting there like frustrated that other people are just standing around doing a a whole lot of nothing. There's some people that feel resentful that they're not being included. They never get the ball, right? And so this is what happens inside of a company. And so how do you solve this? One fix I learned is the RACI model.

5:41So you define upfront when you do the project, you don't just set the goal of the project and the deadline of the project. You also need to define the RACI model. So what you say is, who is responsible for doing it? Okay. So that's the person who's like driving the action forward in the project. A is who's accountable for it. This is usually that person's boss. So let's say you're the chief revenue officer and under you is the head of sales. Okay. So the head of sales is the one who needs to get the sales team to, you know, go from a 15 % close rate to 19 % close rate. And so he's responsible for implementing the plan that you, that you made, or maybe even coming up with the plan.

6:17But ultimately the buck stops with the chief revenue officer because it's a revenue activity. So he's accountable to the result. He's just not responsible for doing the work to get the result. Then you have C, which is the consulted party. So who else do I need to talk to? So maybe I needed to be talking to the head of delivery because I'm closing a bunch of sales, but I'm overloading the delivery team, which is causing us to like have customers churn and not actually like get the product or service that they wanted. And so because I didn't tell him that we're going to all of a sudden start doing this free promotion and get a flood us with customers, he now is on the other side of something that he wasn't consulted on.

6:53So sometimes as a lawyer, it's like, hey, we got, you know yeah nobody likes to bring legal in but you know if there's going to be a legal component to this they need to be consulted in this they don't get to be the one driving it because they're not the responsible party but they get to be consulted yeah and i think the last one is informed and so informed is basically like who needs it fyi who needs to be in the loop but they're not i don't need their input nor do i need their action to make this happen and so you define that at the beginning and that's how you prevent the like i threw the ball there's seven people there.

7:21And somehow, when there's seven people, the ball hits the floor more often than it did when there was one, which is like common dynamic in companies. And I know a lot of people listening to this are entrepreneurs, meaning they want to eventually start a company. And then a smaller percentage has started something. And then a much smaller percentage already has something that's thriving. And so I want to speak to the first category of people who don't have a thing, which is for the first, let's say, 3 million in revenue, maybe a little less, honestly, you can kind of ignore this. You can brute force your way, but it's going to happen faster than you think.

7:54And the transition for me, and for a lot of people, I think it's going to be harder than you think. But what separates the winners from the losers is embracing this stuff. And it doesn't feel natural. It actually feels incredibly unnatural because for a lot of people who start stuff, this is not the, they say screw the rules. But I have noticed that what separates the pretty decent to the great from the great is actually following these rules. Do you agree with that? When you say these rules, what do you mean? Sorry, these best practices of like creating process or like having these cute phrases or constantly reminding people of like within your company what you have to do.

8:30Because someone can be listening to this and they're like, I'm not going to inform people. Like I'm just going to make the decision and go. I totally agree. And I think that, you know, you have to figure out which of these work for you. But the act of hunting these down and constantly trying to get it right, constantly trying to improve it, that's the thing you got to commit to. So like one simple way of thinking about this is, this happens all the time with founders. If you like consult with them, they'll be complaining about something. There's no bigger pack of whiners than a group of founders and CEOs.

8:57If you get them all, if you get them to be honest, there's no bigger group of whiners. And when they start whining and they start whining about how this person isn't doing this and how this other company is doing this and how this isn't working and how that isn't working, right? Like you just start with the people problems, right? Because anybody knows in a company, Like I would have started five more companies if I didn't have people problems. I don't know about you, but like people problems is the one that drains you. That's the one that, that hurts you. It's also the thing that feels magical inside a company when you just get some star people.

9:27Like I'm sure you had the hustle with whether it's staff or trunk or some of these people or you're just like, Oh my God, this is kind of amazing. Like, yes, they're just doing all these things better and differently than I would have ever done them. And I don't have to worry about that anymore. Like, Holy, this is like, this, like it's a next level heaven as a CEO and the exact opposite is true too when somebody is not doing what you expect them to do they're not doing it better than you would have done it you're constantly having this grief it's like going for walks with your dog who bites other dogs or other people like have you ever had one of those dogs i've had one of those dogs every dog she sees it's exhausting because like you walk around the corner like oh like you're always on edge it's horrible and people will ask is she friendly i'm like no you need to get away um so okay what but then you talk to that founder and you just all you got to ask is one simple question.

10:14Oh yeah, that person did that. They're bad at that. They're not doing this. They're not delivering this. They said this, but they did this. Who picks the people in the company? Like who hires and fires? Oh, that's you. Okay. Gotcha. All right, cool. So like that problem actually rolls up to you. And same thing with, oh, they said they were going to do this and then they didn't do it. So they weren't, they didn't get, they weren't accountable for what they said they were going to do. Who holds people accountable? Who sets the culture of accountability? Oh, that's you again. Right? So at some point you sort of realize like, oh, I am the root cause underneath all of the underlying causes in my company.

10:46Even if it's something that you think gets sideswiped, oh my God, tariffs are so crazy. It's like, I didn't build a robust and resilient supply chain. So yeah, I'm mercy to this new tariff policy or whatever, right? You're the root cause of all the problems, which also means you are the root cause of all the solutions. You have the power to do all the solutions. And so then the question is like, what are you going to do to do it? And you're talking about best practices. I think one of the big realizations that I had that sounds very elementary, but I had to learn it the hard way, which is to get the results you want, you simply need to be the type of person for whom that result is inevitable.

11:23So you say like, oh, I want to have this well-run company. Cool. Are you being the type of CEO who would have a well-run company? Are you hiring great people? Are you training them well? Are you holding them accountable? Are you celebrating the wins? Do you give them enough ownership and equity? Do you do all those things? If you're not doing those things, what's going to happen? Hey, everyone, if you're liking this episode on how to be a better CEO, well, I've got good news. So we actually went and just put all of the information from this podcast into a PDF that you can read and download. And we added a bunch of stuff.

11:53So word for word emails that you could send scripts on how to have better or harder conversations, when to delegate, things like that. So if you're trying to be a better CEO, just click the link in the description and you could download it. It's completely free or just scan this QR code. I sent a voice note to my piano teacher the other day. And I was like, hey, is there anything that I could be like, are we doing our sessions right? Is there like a different approach that we should be doing? Like, just want to just check in. And she's like, hey, I thought about your question. So here's the thing.

12:21To get good at piano, here's what you got to do. Find songs you're interested in and play them a ton until you can play them well. And every song will teach you something. The only way to do to get better at the piano is to find things you're interested in playing because you have gentleman motivation and then play it until you're good at playing it. And she was just like, yeah, like, and in doing that, we're learning sight reading. We're learning playing by ear. We're learning how to like control volume control between right and left hand. Wait, was she criticizing you because you don't practice?

12:49No, no, no. She was just saying like, there's not like, there's no third door. Like this is, this is the way. And if I look at like all the areas of my life I'm working on right now, it's like fitness. It's like, great. Guess what? No secret strategy. You're going to show up to the gym or not. You're going to eat clean or you're going to eat shitty. Which one are you going to do? And so similarly with being a great leader or CEO, it's like, hey, listen, it's not that different than being fit where you got to do these best practices on diet, do these best practices on exercise and don't get lost in the weeds about it.

13:17Just be honest. Are you doing those things or not? There's a version of that for managing a company. And what's interesting is I've noticed that leading up to starting something, you read all the self-help books that you possibly can and that gives you the motivation to start. Then you get into it and you think, I don't have time for that. I just need to like put my heads down and get after it. And then you get up to what I call the second mountain, which is you're no longer there to survive. You for sure, you're default alive, but you're not default thrive. And so what do you do to actually thrive?

13:46You go back to the well and you actually start learning all this stuff. Start asking questions again. For a lot of people like me, and you start going to like, this is when like the Tony, like at Tony Robbins, you're going to see both losers and really successful people because they both need the same thing. Because for a lot of people, particularly people like me, I am basically like slightly autistic and like slightly meathead where you get to the same thing where I'm just going to like pile drive through this like brute force this thing I'm never just you're just going to put your head down it's like well you actually have to learn how to have a conversation with someone on having a like you need to like correct someone effectively and here's how you correct someone effectively I'm like oh my god I had to read a whole book on how to have a how to have a difficult conversation which is like the second or third thing I was going to bring up which is like if you have a meeting and the person is on their phone, there's actually a proper way to correct them.

14:35Snatch it? Or what do you do? Slap it down? You just like give them a wedgie, like call them a nerd and push them out the room. Have you read nonviolent communication? Yeah, I actually didn't like it as much as a lot of people did. What I preferred was the motive. Have you read the motive? No. What's the premise of that? Basically, to be a CEO or to be a leader, you basically have to recognize that a large percentage of your time is going to be having difficult conversations. And the best way to have a difficult conversation is A, you get it early on. So if you're in a meeting and you see that someone isn't paying attention, you actually don't wait for it to fix itself.

15:15You correct small things and you correct them fast because that will have a lot of leverage later on. So they're going to know very early on based off the small things, what you expect on them, on the big things. The second thing is when you have a conversation, A, you do it privately, and B, you tend to like compliment them and you say things like, look, I know that you don't mean to be this way, but here's how you come off. And I would like it instead if you did this. Does that sound good? Is that okay with you? Like there's a way to like have that conversation, which is I would, A, I'd be like, well, I don't want to correct that person.

15:42Who am I to like tell them that they should not look at their phone at a meeting? And B, like it's probably, it was just a one-time mistake. They're probably going to like figure it out. And the book, The Motive, it actually says no nonsense. It says, no, that is nonsense. You want to correct this early, early on. Today's episode is brought to you by HubSpot. Being a know-it-all used to be considered a bad thing, but in business, knowing it all, it's everything. Because right now, businesses are only using about 20 % of their data unless you have HubSpot. That's where they take data that's buried in emails and call logs and meeting notes.

16:13They become insights that help you grow your business because when you know more, you grow more. You see, being a know-it-all isn't so bad after all. Visit HubSpot.com to learn more today. Have you ever read The One Minute Manager? Years ago. What was the takeaway? I can't remember. So it's a very thin book. Love it because it's very short. You can read the whole thing in probably 25 minutes, 30 minutes, something like that. And the idea is, it's almost like written like a fable or like, you know, The Alchemist or something like that where it's like, so I went to this, you know, I wanted to do this.

16:43I wanted to be a better manager and I heard about in the town next door there was this great manager and so I went there and I met the first employee and he meets these three employees, sort of like three wishes from a genie essentially. and the guy basically has he's like you want to see how I do it come tomorrow 6am and I'll tell you the one thing the most important thing basically and he does that three times and so the core of that book I would say is like two things that I changed from doing it so the first was planning so I used to either be top down or bottoms up meaning I would be like I'm going to tell you exactly what we're going to do how we're going to do it how this needs to work blah blah blah I'm going to hand you this thing and you need to go execute this.

17:24And then I'm basically just going to be disappointed that you didn't execute it the way I envisioned in my head when I first came up with this, right? Because at that time it was going to work and there's no problems. And so like you're on the hook for all the delivery and I will hand you this thing and you're never fully bought into this because you didn't run it. You got handed this thing. The other way is bottoms up where you're like, you come up with the plans. Maybe I don't even tell you that. Maybe I'm just waiting to see if you come up with the plans. And, you know, people inevitably come up with some sort of like half-baked plan.

17:53And then you're sort of disappointed in it. And they're like, let me see that. You fix it. And you try to improve it. And you've criticized them and you try to improve it. And this guy talked about like, basically like a one-minute plan. And so the idea is like a one-minute plan, essentially creating like a one-pager where the employee writes what they think they should focus on and what they're going to do. And there's like a revision process where the manager basically gives some feedback. And then the employee goes back and tries to work on, like, you know, based on the feedback until you arrive at a solution that they wrote, but you agree with.

18:21And so you get sort of the best of both worlds. They have the ownership of it. They're totally bought into the process. They've done the thinking. They didn't outsource the thinking, but you're totally on board with the thing. So that's like one thing that I shifted of like how I do that. The second one is around praise and criticism. And so like from a separate thing, I learned this acronym, PICS and NICS. So P-I-C-S and N-I-C-S. And so PICS is basically like, how do you give feedback? So you want it to be, if it's PICS, It's positive, immediate, and certain. If it's negative, it's negative, immediate, and certain.

18:55And so how do people get feedback wrong? They try to do the feedback sandwich where they say a positive thing, a negative thing, and another positive thing, and the person's like a little confused about the whole process. They delay it. So if there's something negative, they let it slide. Next one, they let it slide. Next one, they let it slide. By the fourth one, now I'm frustrated. I've seen four of these. You're unaware that this was even a problem or bothering you. And I'm just going to fire you. And I come at you with an avalanche, and you're like, that came out of nowhere. what a jerk. And I'm like, you've had such, so many attempts to do this and you haven't gotten it right.

19:23How dare you? Right. And so it's like, no, but nobody wins in that scenario. So you want to do it immediately. So right after the meeting, right after the call, right? Hey, I really liked the way you did that. Hey, I noticed that you did that. And that, that felt new. That felt like an elevated version of what you were doing before. That's really awesome. Keep it up. Right. The other thing is making it certain. So don't be wishy-washy about the feedback to say, you know, when you did this specific behavior, that made me or the other people feel like this. And therefore this conclusion, do more or do less, right?

19:55Like very clear. That's a nonviolent communication example. Yeah. Like a framework of how you could do that. And so like, you know, just little things about, you know, I agreed with that, but was I actually doing it? Like, was I actually doing it immediately? No. Was I doing it, with high certainty and high conviction? No. And so you just do those little things and you get better. These little things sort of stack up. You've read the story about the theory of marginal gains, that British cycling coach. You know the story? So it's like, maybe it's in Atomic Habits or somewhere. It got popular for that reason.

20:28But basically the British cycling team was losing in the Tour de France and this coach comes in and they're like, okay, new coach. We got to overhaul the strategy. We got to change all this big stuff. What are the big swings this guy's going to do? And he was like, we're going to adjust the bike seat, make it like, you know, 7 % thinner. We're going to like grease this. We're going to do all these small things that individually sounded like inconsequential. Like, okay, that's going to make a big difference. And his theory was like, if we can stack 1 % improvements across the board of what we do, there's an accumulation of these marginal gains and the marginal gains become substantial if you stack them, if you add them up.

21:06And so like, that's how you win in most areas of life is you just start to stack a bunch of things that each individually don't sound like game changers, like lead bullets, right? No silver bullet. You just keep stacking them until you sort of overwhelm the situation with your success. And a lot of time you'll get guys like us who are saying this in the very tech bro way where you're like, yeah, this is how you give compliments. And some like reasonable person listening is like, duh. And it's like, well, the problem is that what gets you to the brute force that gets you to the stage where you start worrying about this, it's actually the opposite way of handling people.

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21:45The way you start is the opposite of what you eventually need. And so you get to this point and you're like, what do I do now? And I'll give you one last example. For company values, I've actually taken a different stance on this than I had before. The different stance is when I started my last company, I actually wrote the values out in advance, and I failed to live up to them. And my premise when getting Hampton working was I was like, I'm actually not going to write down values. I'm going to start this company, and I'm going to see how it feels. Then I'm going to name the values later on. Jack Smith, baby naming.

22:21My friend Jack said something, and he did something that honestly changed my life. He did the weirdest thing that I'd ever heard of, and I mocked him at the time. He did not name his baby. Jack had a baby and he refused to name her for the first year. And I said, Jack, why are you doing this? He goes, well, I think I should get to know her first before we give her her name. And I said, Jack, that's absolutely insane. What are you doing? And I started thinking about it more and more. And I got to know the baby. And we started calling her legal name was Baby for the first year. And I was like, you know, baby's kind of nice.

22:52This is kind of nice. And then they like thought of all these names that represented her personality. And now I know her as her new name. and I realized that is actually sort of brilliant. And I did the same thing with my company where I purposely did not have values. And I was like, what attributes bothers me? And what attributes do I particularly love when I see us do here? And now after, you know, my company is weird. I started it, I had someone run it, now I'm back running it again. So we're like a weird timeline, but it still feels early for us. And we are now, but we're now like a couple of years in, just now naming our values.

23:25and it has felt like that has been 100 % the better move. And it feels great, honestly, to stick to these values because before when I named values, it seemed kind of weak. It seems kind of dumb. You're like, I'm gonna hire people according to these values that I actually made in the case of The Hustle. I made when I was 26, I'm now 28. I don't even align with them anymore, but I'm stuck with this. I don't like this feeling. I feel like I'm in a prison. And so now I'm just gonna look soft by not following the things that I said I was gonna follow. We did things differently this time and it's been so much better.

23:56What's an example of a value that emerged? I can give you the three. The first is... You're the first person to ever ask me about my company values, actually. So the first one is fun. So I just value fun. And so fun means in our copy, I want to do silly stuff just because. But also, I don't want to follow data all of the time. Sometimes we're going to do stuff just because it's exciting or it's fun. And I'm going to hire people who I have fun being around. The second one is speed. So I realized I valued moving fast a lot more than I previously thought. And the third one, which is actually kind of controversial, or it doesn't feel right at first, but I'll explain, is pride.

24:32So what does pride mean? I told my company, and they're like, gay pride? What do you mean? And I'm like, no, guys. I mean, you could have that, but that's not what I'm referring to. It's like we're having fun. There we go. Yeah. Yeah. Yeah, it's just a bunch of bros being dudes, you know? Pride meaning I want us to have pride in our personal lives and our work lives. And so what that means is we started off virtually and the data showed that we could sell it and make money for it. But it didn't feel good. I didn't take pride in that. I took pride in saying we have in real life, even though the data didn't exactly show at the time we should have done that.

25:08I'm doing it anyway. Or if we're going to lay people off, I'm going to go above and beyond. And I'm going to give them like more severance than the market rate because it just makes me feel good. Or if we can afford it, which we can, when a vendor submits their bill to us, even though we have a net 90, I'll pay them that day. because it feels good to do the right thing and to treat people well and to have this reputation as someone who does something a certain way. And that gives me a lot of pride to do that. Or when someone was, and I tested this, I would tell a couple of people, here's the value that I'm doing.

25:36And someone showed me a text message that we're sending to potential customers to remind them of something. So like a reminder text message. And I was like, show some pride. That's just a boring boilerplate message. Show some pride, make it something special. and so like that is a way where I started like throwing this out there and like using it and I'm like oh my god that actually changed behaviors I told someone to like show some pride and they like in this really small thing they're showing pride or we had a work event and a couple of the guys there they just dressed sloppy like some of the other people like looked really nice and I don't expect everyone to wear a suit or anything like that but they just like their their like beard was all out of like whack and they have like kind of a dirty shirt on I'm like dude have some fucking pride, man.

26:18You don't have to go buy new clothes, but show up a little bit better than you are now. And so that's been the values are speed, pride, and fun. That's interesting. Yeah, I'm curious how it's going to play out. I've never heard of somebody do that, where you do it later. And also, I think it's very rare for values to actually show up. I would say that out of 100 companies who took the time to set values, what percent would you say actually live by those values? Live by those, I don't mean perfectly. I guess what I mean is compared to a similar company like them, they do things differently because they valued it.

26:59What percentage would you say actually do that? Very few. But I think to be like 10%. But I think to be a 90 percentile plus company, I actually do think you have to do things like living to your values. I think in order to be... Who have you seen do that? Have you seen anyone? Like, have you kind of gone into a company and been like, wow, they actually... Well, like the companies that I tend to admire or the books that I read of the people I admire, they're kind of quirky and they're very different. And so I think Coinbase was a good example where they took a stand. I think they said no politics.

27:31They also took a stand that they're going to be remote first, but their offices, they just put this video out, where their offices are going to be like the best and they want it to be beautiful and they want it to be people that they love it. They love working there. They didn't have to do that, but it just seems important to the CEO and now to the rest of the company. Or with Jason Fried from Basecamp, like he does things that are a little bit different than normal. And I think that what it does is it turns off a lot of people, but the people who truly love it, they absolutely love it. I think that's what's going to happen at my company.

27:58My value, the values that we have, they are going to turn some people off and eventually they're just not going to work here anymore. Which one do you think is going to turn people off? Because those all sound pretty uncontroversial to me. I want to not have fun. I want to take no pride. I want to move slow. I don't think anybody would say that. Dude, everyone wants to move slow. Like moving fast. Nobody states that. Yeah, but you could tell like when someone like says like this is going to take six weeks and like, well, what would it look like if it took two weeks? That makes so many people uncomfortable.

28:26So we've talked about this before. I'm surprised you didn't do it. Zuck had this thing back in the day where he said one of the great lessons he got when he was a, because he was a young CEO. I think he was 18. He's like, you need to acknowledge the trade-off in the value itself. So, you know, instead of saying, speed, because everybody says, yeah, of course, we all want to move fast. He would say, move fast and break things. That was the value. And because he said, move fast and break things, you would explicitly acknowledge the trade-off that, hey, when you move really fast, you're not going to, it's not everything's going to be done, you know, perfectly, neat, and orderly, like things are going to break, things are going to happen.

29:01And by putting it in the value, it made it real. It made it something that not every company would agree with. It made it something that you could be criticize on and made some acknowledge what will be uncomfortable about doing this. And so I'm surprised you didn't do that. I'm still working on wordsmithing, if I'm being honest. But I think that speed and pride actually can be inverse and they can be the opposite. But I actually don't think that most people, I don't have a cute phrase yet, like move fast and break things. But I don't think that most people are comfortable when you say move fast.

29:33And I think that at my company, I've noticed that someone will say something, this is going to take a quarter, and I will pose the question, what do I have to do to see results for this in two weeks? What's that look like? That actually rubs a huge percentage of people the wrong way. The type of people who kick ass at my company, they say, oh, you know, that's kind of an interesting question. I guess if we do this, this, and this, and maybe that would be exciting, we could actually pull that off. But a huge percentage of people, I think, are very nervous about speed. They're very nervous about moving fast.

29:59I mean, have you not experienced that? No, 100%. I just don't think that if you say the word is my value is speed, I think when you say, who agrees with this? 100 % of people raise their hand. And nobody will say, you know, I disagree. I think we should be moving slow. I think 0 % of people do that. So that's why I'm like, in practice, what you're saying is actually more like uncomfortably fast, right? Or, you know, break the speed bar. So what we do is whatever would be normal for this project, we're going to cut that in half as a default. We're going to have a different speed bar than everybody else or than whatever your default is.

30:33And so I think I would have pushed you to be like, hey, I think you should make that actually say what you're trying to say. Yeah, admittedly, I'm still word spitting a lot of this stuff. But I'll give you an example for speed. It's like if you go to joinhampton.com and you sign up or you submit lead information. If you just pay me. No, no, no. If you like, if you're, if you, it doesn't work perfectly right now. But if you apply and you fit our criteria, meaning you have a company that does at least 3 million in revenue and you're one of our 13 chapters. Helen, who works at a company, is going to call you.

31:07Right now, it's 60 minutes, but we're trying to reduce it to 15 minutes. You're going to get a phone call from someone who works at a company. And all they're going to do is say, I see you. Thank you for applying. We have to review all the application, but I'm here. And you can text me if you need anything. Thank you so much. So that's an example of moving fast. I think you should make, you know how some companies have a wall of love? I think you should make a public or at least public in your company list of you write the value at the top so you write whatever your thing is like move uncomfortably fast that's the value and then i think you should have a running list of concrete anecdotes where that's true and then you just see how long you can get that list to be and you can see how how much is being added to that you can see who's adding to it because that's the person who's actually like living by the values um and then you'll when you do that when you actually write it down you'll realize like damn we say that, but what do we actually do that's fast?

31:59Or we say take pride. What's an example of something we do with pride that others wouldn't, or we weren't before we actually did this? And I think when you do that, it actually becomes real. That's a good idea. I think most values just are... I think that percentage of companies who actually live their values in a way that's different than the company A versus company B is so small. I think 10 % is extremely generous. I think the number is probably closer to 1%. Who have you seen? Well, you know, the hard part when you're an entrepreneur is that you don't really work in many other companies. And so you only hear like secondhand information or you got, you know, we got acquired.

32:33Twitch, I don't think, I don't even know what the Twitch values were, but whatever the hell they were, they were not very powerful and they were not, we weren't doing them, or at least I didn't see anybody doing them, right? Nobody talked about them. And so I think that, you know, the couple of times that I've been in other people's companies, I haven't felt it. I think it's quite rare. You know, I think Elon does this really well where he drives a hardcore sleep on the factory floor mentality. So you see it with stories of him, literally sleeping on the factory floor. You see it with his company.

33:05So right now, if you go look at XAI, Zuck is throwing huge pay packages at people. OpenAI has the most popular product. Why would I, if I'm a top researcher, go work at Grok? This is the question they have to answer. And what they do in their propaganda is basically they show how, you know, quote unquote, cracked the team is, how hardcore they are about what they're doing, the culture and taking pride in overworking. And so like he does that. He also does it on the speed bar. Like there's a story of, there's a story in the Bolter Isaacson book about him that Jason Fried actually told on the podcast.

33:40And it was basically like they were ready to launch. It was a, they were doing some project with NASA. They were ready to launch the rocket. So half the NASA team was there to watch. And then there was the SpaceX team. and they discover a crack in the skirt of the rocket. And they're like, oh, shoot, like there's going to be, like we need to delay the launch. There's a crack in the rocket. And he goes and he looks at it. He's like, why do we need the skirt of the rocket anyways? And they're like, well, it's for additional thrust. He's like, will we have enough thrust? So what happens if we take the skirt off?

34:16What if we just cut this? What if we removed it? Like, there's like a set of shears over there. Like, what if we just cut it off? And they were like, well, you'll lose thrust. He goes and he does some calculations, like, on the side. And he comes back. He's like, we'll still have enough thrust. Let's do it. And he himself takes the shears and he cuts around the crack and basically removes it. And then that's the rocket that crashed. Yeah. And he totally didn't have enough thrust. It was insane. No, it actually, the launch goes well. And the NASA director wrote about this afterwards. She was standing there.

34:47and she goes, she's like, I've never seen anything like this. The NASA engineers, all we could do is stand there and watch. Like this would never be the way that we would do a launch. Like this was unfathomable. And, but that's what they did. And so those are the concrete anecdotes where you're like company A versus company B, company A does something different. There's another story of like, they needed to get a rocket from like one place to another and the ship, you know, you normally put a huge rocket on like a ship and take it from, you know, point A to point B, but it was going to be like three months or something like that.

35:19And so he's like, could we drive it there? And they're like, drive the rocket piece? Like, you know, drive that thing there? I think I saw that. Wasn't, they put it on like a bunch of trucks and the car went like five miles an hour. They had like a car in front that was basically like clearing the way. And literally when there was power lines, the guy would stand up in the truck, on the front truck and with a stick and push the power lines up so that the truck with the rocket could like go under. And they now get into this route. Elon's basically like a redneck. Elon's a hillbilly. No overpasses.

35:48They were like, oh, we're going to have to drive around here or go that way to get there. And they did it there, right? That's like the equivalent of being like, it's like, I got a guy. You need the wire removed. I got a guy. Just grab that old broom over there. I got a guy. Yeah, so I just think pretty broadly, whatever percentage of energy you're going to, great, you got the three values. I would just be like, it's not what we say, it's what we do. And so we're going to track what we do that's in line with these. and like, you know, that's what I'm calculating. And every week, every month, I'm going to see how much we add to this list.

36:20That's a great idea. I didn't think of, so we have a thing where we give examples of, like we celebrate them, but like, you know, who moved fast and even if it was a bad thing, let's like talk about it. You know, you do that with like sales calls. You're like, all right, let's get like the blunder of the week. All right, here, does everyone know why? Yeah, like good job trying and let's improve this way. So I used to give out, I mean, this is, I'm not like, this is not what they teach you at harvard business school but here's what i did i used to i bought this replica wwe championship belt and every friday i would give it i would basically i would call the team over so get everybody away from the computer we would all grab a beer or a drink or whatever and we would stand so we'd stand a little huddle as you know with 12 15 people at the company at that time and i would basically give the belt to somebody and they got to keep it like kind of on their shoulder on their desk for that week and the belt holder got these like small perks.

37:10Like you got dessert first at lunch, you got this thing, whoever had the belt that week. And then that was basically my opportunity to shout out the person who did the thing. That's the behavior that's in line with the values. And so it was never like the person in charge. It was the person who did something above and beyond the call of duty or like, you know, in line with one of the values. And I would tell the value story and I'll tell you what the person did that was like out of the ordinary, that was in line with the value, that that's what we're all about. And then I'll hand them the belt.

37:37And like, guess what? you do that 52 weeks in a row, like people start to get it. It's like no different than second grade class. Like people start to, people start to understand like what gets rewarded around here, what gets, um, you know, what, what is the, what is the benefit? And then what I did was I assigned a prize to it. So you would get some cash. So I'd give you like, I don't know if it was like a thousand dollars in cash. And the rule was you can only spend that thousand dollars on something that is a story that you're going to tell us, you know, the following week. So the belt holder would be like, yeah, I got the thousand bucks.

38:07And what I did was like, you can't just be like, I paid my rent with it or like I paid groceries. It's got to be something that's like story worthy. And so then that person got to stand up with pride and like do the thing. They got to come home that day and tell their girlfriend or their wife, you know, like, hey, like I won a thousand bucks. I got the belt. I like did this thing. And you get to, it's like you, that's how you make it like deep inside of a company is like, you know, reinforce it on a weekly basis and almost like productize it. Alex Ramosey says something cool. He's like, most of your team, they don't need to be taught.

38:35They need to be reminded. For the majority of things, you teach them once and then you just got to constantly remind. It's almost always a lack of reminding, not a lack of teaching. I thought that was really good. It's true. I mean, it's true for myself too, right? What are the most valuable lessons? It's like the ones that I keep having to learn again and again, right? Yeah, it's like I've learned this all. I don't need knowledge. I need wisdom. And just like you need to remind me in order to make this wisdom sick. Yeah, exactly. I think you guys like this podcast for two reasons. One is if you are building a business, it's lonely.

39:07And listening to Sean and I, we're sort of like your friends. And the second reason is you know that we are builders. We love building companies. It's kind of our life's vocation. So if you have a business that does at least$3 million in revenue, I think I know exactly what you're experiencing. You've built a great business. It's working. And you finally have a second to look up. You're young, you probably run an internet company. In your town, there's potential that you're a freak, that you have no one else to talk to about growing your company. In fact, when you even go out in public, you probably don't even like telling people what you do for a living because you don't feel like explaining it.

39:40If you fall in this category, that means you're making the biggest decisions of your life, 10,$20 million decisions all by yourself alone. And without that push, in my opinion, the risk is not blowing up. It's drifting into good enough territory, into becoming mediocre. And the worst thing that can happen to you is 10 years from now, you look back and you realize, I missed this amazing opportunity. I didn't grow, I plateaued in life and in business. My company, Hampton, we changed that. If you're running a company that does at least 3 million in revenue, you can apply at joinhampton.com. We vet you, we curate you, and we give you eight handpicked founders who have similar businesses, similar sizes as you, who will challenge you, who will hold you accountable, and who will give you perspectives that you cannot get anywhere else.

40:26and this all happens in real life. So check it out, joinhampton.com slash network. Can I ask you about this thing that you have on here about, I want to tell you about something, but I first want to hear about this edge. Founders who go all in the second time on edge talents that they have. Yeah, basically I'm the type of entrepreneur who seeks variety. I get excited by new things and I think there's a lot of entrepreneurs who have that same, you know, that's the kind of guy they are, right? That's the kind of gal they are. They're into that. I think everyone has that. Everyone has it a little bit.

41:00And there's some, I don't know if these other people are just better at resisting it or they have the opposite urge. So we had the founder of RX Bar on the podcast and Peter. And so he had come on and he had built RX Bar from his parents' kitchen table. He built the number one or whatever, like a top protein bar basically. Sold it for whatever, what was it,$500 million-ish? Or more. Or$600 million, something like that. And we were talking to him a couple years later and we're like, Peter, what's up, man? What are you excited about? What are you interested? What are you doing now? What are you going to do next?

41:31What's the next move? He's like, I'm launching a protein bar. Like what? And he basically was going back to the market that he knew better than anyone else with a new product, David Barr, which is, by the way, now already like multi-hundred million dollar company faster than RX Barr ever was. In terms of revenue, right? Because he's playing, yeah, because he's playing, I think we talked about this, I think they said they're over a hundred million in revenue and he's what less than two years post launch. So, you know, so incredible success. And it kind of makes sense. It's like when you see people playing a video game and you see those guys who they're not buying the next game and starting that they go and they basically speed run a video game.

42:09If you've ever seen people speed run Mario or something like that. I mean, they just know the level like the back of their hand and they're able to like do it with a level of mastery that, you know, any newcomer, including themselves would not have been able to do. And so this fascinates me because I'm so opposite, You know, if I have a success in something, the last thing I want to do is go do that again. Boring, not interested. And yet there's this group of people that do this. And the reason why this came up for me was I was looking at carbone pasta sauce. Do you know this story? Yes. Amazing.

42:38Amazing, amazing, amazing. You want to tell a little bit of it and I'll fill in some gaps? Okay, so I believe Rau's is a restaurant in Manhattan. And I think it's actually only one restaurant, like a small restaurant. It's a family Italian restaurant. Not even, I think, in a popular area of Manhattan, but it was still a very popular restaurant. And now a lot of people know Rau's tomato sauce. That's the pasta sauce, which is, it's not like gourmet level, but it's like a significantly elevated ragu where it's like$8 a bottle versus like the$4 a bottle. and so approachable, but definitely elevated.

43:13And it's crushed it. It's killed it. And it basically took this very small Manhattan one-store restaurant and made this massive, potentially multi-billion dollar brand. Now, this other company called Carbone, which is a little bit more, less of a family restaurant. It might be a family restaurant, but a little bit more flashy. And I think they have like amazing, I think it had an amazing leader. But basically the CEO of Rouse has done the same thing with Carbone. So now you can buy Carbone sauce and it's the same thing where it's slightly elevated, but still approachable. And just crushing it.

43:41Is that right? Yeah, you nailed it. So just to fill in some of the details. So Rouse scaled up and sold for$415 million in 2017. And since then has sold one or two, like private equity sale, then sold one or two more times. Last one at$2 billion. So here's this$2 billion pasta brand and the CEO runs and scales that company. And separately, Carbone basically kind of goes through a similar model. When the pandemic hit, Carbone the restaurant, which had this incredible reputation, tries to figure out like, okay, well, now people are at home. Our business took a hit. It became this incredible forcing function, right?

44:18So like sometimes you turn your disadvantage into your advantage if you're a great entrepreneur. That's the key. So you look at this situation and you're like, all right, what am I going to do? How am I going to flip this on its head and not just survive this, but can I do something with this? And so they decide, hey, we're going to come up with a jar version of it. We'll sell it direct to consumer on our website. Okay, great. So they go through dozens of trials. They're getting the flavors right. And, you know, they launch and it does okay. Not great. So this guy, Eric, comes in and he comes over from Rouse.

44:47He had a non-compete. His non-compete expires. He says, all right, great. I'm going to do this. And they spend kind of like four months just working on recipes, flavors, trying to figure it out. They're in the lab. They're in the lab. They're grinding. They're grinding with the sauce flavors. They're grinding garlic. Yeah, they're in the lab. The problem is, you know, there's a pretty competitive category. And so, you know, pasta sauce, which was, you know, obviously like not a new category. It's like, where's the opening? And he goes, he thinks with my reputation, my connections, I'll be able to get us into retail.

45:17He goes and he knocks on all the doors and no interest. And so he's like, shit, all right, what are we going to do? And for basically, I think he said like 18 months, they, you know, he was struggling to get people to call him back and he could not get his foot in the door. And so then he had to think about, all right, we need to come up with a value proposition. We need to come up with a position that's going to be different enough where the retailers want to carry us. And so he's like, all right, listen. He puts part of his hat is like a Don Draper hat. The other part is the economic hat. So the Don Draper hat's like, all right, we need to market this differently.

45:46This is restaurant quality sauce. We use San Marzano tomatoes. We cook them on an open kettle on fire, right? Like, you know, who knows how, maybe that's how all sauces are made. Who knows? But starts to build a little bit of the story. And because this is so premium, he's like, you know what? we're just going to price this at twice the price of the other. What's their price? Double it. That's our price. And so now it's priced at$7 to$11. It's a very expensive item. But what that means is that a retailer who normally takes a portion of that sale, instead of making 50 cents on a sauce, they're now making$2 and 50 cents.

46:25So they had a big incentive to carry it because they're like, hey, if this sells, we make way more per jar than we going to otherwise. And so this becomes the pitch and this pitch starts to work. It takes off. And now they're north of a hundred million in sales. They're in 27 ,000 stores. And it's just fascinating to me that this guy is just running this pasta playbook again and again. And I started to think about that. And I was like, who else doing that? So we talked about the RX bar friend of the pod, Nikita Beer did the same thing. Basically he's like, cool, I'm going to make these like teen, these sort of viral teen apps where teens are able to kind of like, I don't know what you would say, like compliment or like give, like, hey, who's the most likely to do whatever?

47:10Who's the most blah, blah, blah friend you know? And then it sends them a message. Somebody said you're the blah, blah, blah, blah. Click this to see who said that about you. And for a teenager in high school, like, that's an irresistible text. Goes viral, right? And so he's done this a couple of times now and has parlayed that into like, now he runs product for X and works with Elon Musk. Which is insane. Which is an insane career leap that should be studied. Okay, but we have other friends. So there's a friend of the pod. We can't name them. But in the D2C space, similar to RX Bars, they built a brand.

47:41And we have one friend that has now built four different$100 million brands using the same e-commerce playbook. Two of their brands literally compete head-to-head against each other. If you search in this category on Amazon, the number one product is theirs and the number two product is theirs. They look like two totally different competing brands. He owns both of them. And I was looking at the revenue of these companies and it was like, oh yeah, this one did a little better this month. It did 8 million this month. And the other one did 7.5 million this month. And I can't believe it. And this is like, almost like full self-driving for him.

48:14He's on autopilot. He knows what to do with these companies. I don't exactly know who you're talking about, but I think I do. And answer this question. Is there a chance that the website of the two is the exact same website template? Yeah, why not? because I think I know who you're talking about. I think they owned one thing and then they sold it and they just basically it looked like they said, so let's just say hypothetically. No more clues. We can't do any more clues. No, no, no. Hypothetically, just like a pen. They were like, all right, this worked for pens. Now let's do the exact like export, upload.

48:46Now we're going to do the same thing for lighters, but like same branding. Yeah, yeah. So again, if the sort of mindset of like going back and speed running the level again, so different than me. I mean, what do you think about this? Do you have any examples of this? What do you think of this model? It's 100 % the way to go, I think. But you don't do that. I think I did. Yeah, the reason I started Hampton was because we, at The Hustle, we owned a community called Trends and I realized all the mistakes that I made. So I think it's the same thing. Yeah, I mean, my career started, it felt like as a blogger when I was 20 years old.

49:19And frankly, I feel like I've been doing the same thing for now 15 or 16 years. So yeah, I do think it's the same thing. Explain your thing. When you say doing the same thing, what's the thing for you? It's all been centered around content and community. So basically, when I moved to San Francisco, I had a book club. And that's actually how I met some of my best friends. So like of the two guys who are in my wedding, or of the six guys, two of them I met via my book club, where we would have a monthly book club where we would meet up in real life. And then from there, I hosted a handful of events called Bootstrap Live.

49:50In order to make these events popular, I started blogging, creating a newsletter. That turned into a huge conference called HustleCon where I actually just looked at the numbers last night because we were thinking about doing some more events at Hampton and we had 10 ,000 people in one year in 2018 come to our events. So I've been doing events in community for 15 years now. So it's been actually quite consistent. Even more specifically, you're like, I want to have this community, either personally be a part of it or attract this community and then you're like, cool, how am I going to do that? I'll use content as this magnet to bring people in, whether it's the podcast, it's the blog, it's a newsletter, it didn't really matter.

50:28It's like, I'm going to go talk. That's going to attract these types of people. And then my business is the community. Whether, you know, HustleCon was like, I'm going to charge you$300 once. Trends was like, I'm going to charge you$300 once a year. Hampton's like, I'm going to charge you whatever, $8 ,000 once a year. And you've just been doing that same playbook, but smarter, better each time. Yeah, I basically am trying to make up for the mistakes that I'd made in the previous thing. And, you know, like, I think that when I started the hustle, I think I told you this. My goal was to get to 100 million in revenue with a newsletter.

51:01And at the time, that was considered laughable. And frankly, I didn't entirely believe it, but I was like, I don't, I was like - Frankly, I was the one laughing. Yeah, I laughed at myself. But I was like, I know for sure it gets to 30 million, but I have a feeling that if something can get to 30 million, it could probably get to 100 million. And like, there was no math behind it. I was just guessing. And I was proven to be right. I unfortunately didn't do it. I sold too early. But my competitor, now one of my best friends, Austin Reef, he actually did do it. And so the idea that I've basically have looked at either community or content, and oftentimes they're married.

51:31And I'm like, I want to get this to 100 million in revenue. I have never built a business to 100 million in revenue. And that's the one thing I've been trying to do now for 16 years. And I hope I can pull this off. But it's been content and community the whole time. And frankly, I didn't do it on purpose. I was just trying to do stuff. And I'm like, oh, this comes way easy. I'll just do this. I wish I would. I don't think. I think I've always failed at being reflective and being like, oh, like I made this mistake before. I can avoid it. So oftentimes I actually continue to make the same mistake over and over and over again.

51:59But with like Peter or the guy you're talking about or some of our other friends who are two-time founders in the same industry, they do a much better job than I personally have with using the same contacts, the same group of people and just rinse and repeating. So by the time this goes live, I think the Eric Ryan podcast has gone. We'll have gone online. And Eric Ryan, if it hasn't, founded, I think, four companies that if I had to guess, each of them was in the nine-figure valuation. And he just did the same thing over and over and over again with the same people. And I definitely think that's the way to go.

52:25And it could be way more fun. And so you go back and you commit the same crime again and again and again. And I kind of love this model. I don't do it myself. I don't really have the – that's not my wiring. But I find it fascinating. Another example of this is the guys who started Money 2020. I don't remember the name. Oh my God. Dude, I've been begging him every month. I send him an email. I say, will you come on MFM? He has told me now that he's going to come this November. So I'm putting that in the record. It's happening. So what's the guy's name again? Jonathan. Jonathan. All right. So what these guys did, which is amazing, is they basically figured out a model, a blueprint.

53:01And like a home builder who has blueprints for a home that they can just copy paste and just build again and again and again. They've basically been doing that for, I don't know, industry conferences. I don't know what you would call it. Is there a different term for that? So if you want to figure out and follow along, everyone should Google this guy's name. His name is Jonathan Wiener. Go to his LinkedIn. And he originally started as a conference business, I think in 1996. I think that was his first event. And if you go to his website, you'll see the name of something like six different events.

53:34Go to the website of each event. It's the exact same website, but in a different niche. So he had Money 2020, which was a payments conference. and there was a shtick to all of his conference. I think you get a$2 ,000 ticket, but if you're a vendor, you're obligated to go to three different meetings with different people. I think that's part of the whole thing. So he did Money 2020, which was a payments conference. He did Shop Talk, which was an e-commerce conference. He did Grocery Talk, which some food, the food business, I guess. And then now he has Human X, which is for artificial intelligence.

54:11and he also has health, which is for health innovation. And so he's done this where, I think he's on his fifth or sixth one, but the previous four collectively at each time, if you add it all up, I think the public price is six or$700 million. So it was like one was 125, another one was like 200. And he's done that four times to where it adds up to like something like six. Yeah, actually it's, the adding up is not even the most impressive. It's the fact that each one succeeded and became a nine figure. so over$100 million business, again and again and again and again. It's literally like having a money printer, right?

54:48So I like these people who have these blueprints and then go back to the well. And they are these sort of repeat offenders. And I think it's pretty fascinating. The problem, of course, with this is the psychology. So one thing that a lot of founders struggle with is knowing too much. And knowing too much hurts you in two different ways. The first is, if you've been in a space for a number of years and you met all the right people, you learned all the hard lessons, you know the nuances of that space, you're the most equipped to do it, but you also have the most scar tissue. And so some people literally can't get past the scar tissue and the trauma of it.

55:22And emotionally, they don't want to go back into that space again. And they want to go into a new space and get new scar tissue from new spaces. And that's a very, very, very common thing. What happens when it works is sometimes you then get a different problem, right? Yes, you know a lot. You know how to do it, but you're bored of it. It's like sitting on a seesaw that's balanced. You kind of want to go up and down, right? Like that's kind of the point. And so a lot of people who are in the game of entrepreneurship and you succeed, maybe your money problems are solved now. So now if you're playing, you're not playing for the money as your top priority anymore.

55:55You're playing because you like the sport of business. And the question is, if you're going to play in the sport of business, like where are you going to get more kicks? Are you going to get it from going back and dominating and doing that again? Some people do do that. And there's other people that need something new. And I've always been in the need something new category. I didn't really even question it. And over time, I've met a handful of people that do this. I know one guy that did this with sports betting. He built the most popular kind of blogs in sports betting. And then he basically sells those leads to sports betting casinos or website or like, you know, FanDuel, DraftKings type of thing.

56:25So he dominates the lead flow and then he sells the leads. and he sold one company for like 40 million. Then he did the state. He's told the story on the podcast. If you go look at when I sold the Milk Road, go listen to Kendall's part on this. Basically, he did it in, I want to say like New Jersey, or he did it in the first state that it was legal. So only New Jersey was legal. All of his competitors were like, oh, US market shut down. Only one state out of 50 is available. It's a dead market. We got to go international. And he had the opposite takeaway from that. He's like, oh, so I could just dominate New Jersey.

56:59And he created like NewJerseySportsBettingInfo.com or whatever, you know, some website like that. He owned all of the New Jersey sports betting traffic and he sold it to one of the companies for I think 40 something million. Then he did the same exact thing again. Minnesota opened up and he literally like repeated it, did the same thing in Minnesota, sold it again to the same company for another 45 million, but faster this time. And this time they were like, oh yeah, shit. Okay, in the contract, any other state, you can't do this again. Like you can't do this. We didn't put that non-compete in the first one.

57:29We didn't realize that, oh, you're just going to do this again in the second one better than we're going to do it. And so he sold the same company essentially twice for$40 million or something each. And then, by the way, I just caught up with him recently. Guess what he's doing? He did it again? He's selling leads, doing the same thing in the same playbook. I couldn't believe it. And so actually, I totally could believe it. It's actually the most believable thing in the world. All right. Is that it? That's it. That's the pod. Hope that stuff helps people, I don't know, run their companies better.

58:00All right. Talk soon. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never look. This episode is brought to you by HubSpot Media. They have a cool new podcast that's for AI called The Next Wave. It's by Matt Wolfe and Nathan Lance. And they're basically talking about all the new tools that are coming out, how the landscape is changing, what's going on with AI tech. So if you want to be up to date on AI tech, It's a cool podcast you could check out. Listen to The Next Wave wherever you get your podcasts.

From the publisher

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Episode 759: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) and Shaan Puri ( ⁠https://x.com/ShaanVP⁠ ) talk about the things they wish they knew when they were first-time CEOs. 

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Show Notes:

(0:00) CEO Masterclass

(38:06) Abusing Your Edge

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My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano

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