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If I Started Over Tomorrow, I'd Do These 7 Things First

19m 42s

If I Started Over Tomorrow, I'd Do These 7 Things First

The speaker shares seven life lessons learned through decades of entrepreneurial success and hardship, emphasizing resilience, scale, and strategic thinking. He begins with the powerful idea that not giving up is the most heroic act, rooted in a memory of surviving financially as a college student through dumpster diving. This experience became a symbol of perseverance, reinforcing a daily personal commitment to not quit. He stresses the importance of building large-scale businesses, as they attract higher valuations due to greater multiples. A key competitive advantage—called a "moat"—requires heavy upfront effort, such as building a massive email list through speaking events, which later enables sustainable revenue. He argues that business value isn’t about exit, but about having multiple options—including flexibility, partial sales, or independence. Every goal has a playbook, and most are publicly available, so the key is to learn and apply proven input-output models. He warns against risking your core life or business for a single opportunity, citing real cases where reputational or financial collapse followed. Finally, he defines "deserving" as showing unreasonable effort with a reasonable expectation—such as dedicating intense time to mastering a skill or relationship—leading to greater chances of achieving desired outcomes. These lessons, drawn from building $2 billion companies and enduring financial losses, serve as practical guidelines for anyone seeking a more resilient, purposeful, and successful life.

Transcription

3930 Words, 20535 Characters

English
My parents made the ultimate financial sacrifice to send me to college in the U.S. In fact, there were times where I was even dumpster diving for food to make ends meet. And as I reflect, I think about from that point onward, life has been an insane roller coaster. I've had a chance to build $2 billion companies, be a banker at Goldman Sachs, invest in over 100 plus businesses. And today I'm the CEO and managing partner at Acquisition.com with my friends, Alex and Layla Hermosi. And my goal is to buy the Anaheim Ducks for a reason. So you should check that episode out at some point. But the reason I'm making this episode is that sometimes I reflect back and think about, man, how does somebody go from that position to having a decent life and a lot more to grow, but having a decent life? And there are some lessons. If I had to do all of this over, what advice would I give my younger self to make this process go faster, go smoother? And hopefully I have these seven lessons that I'd like to share with you. Lesson number one is a quote from Aquaman. And it says, not giving up is the most heroic thing you can do. Now, without context, that would make no sense. So let me explain how this worked. When I was a freshman in college, there was a situation. Where I just didn't have as much money. My car didn't have the meal plan. So for a couple of weeks, I did not have a lot of food. And I ended up dumpster diving to get some pizzas and a Subway sandwich, et cetera. I even had to fight with a raccoon to do that at one point. Fast forward 22 years. I was invited back to be the commencement speaker at college. When I went back to speak as a commencement speaker, I was able to. I told this story. I told the very story of the exact dumpster that I dumpster dived on. I told them exactly what happened that day. I told them what, what, what, what had to have happened over the last 22 years. And after I finished that commencement speech, the Dean did something. He took me back to that same dumpster. I got to see the same dumpster that I dumpstered over. And on the side of the dumpster was this poster. Not giving up is the most heroic thing you can do. And that's what hit me so hard. It felt like. It felt like life was full circle. It helped me see, man, that that's what happened over those last 22 years. That not giving up was the most heroic thing that you can do. So if there is something that you are working through in your life right now, and you believe so much in it, I tell myself this one thing that I want to give you today. And you probably can just be done with this video after that, which is I just won't quit today. I can quit tomorrow, but I just won't quit today. And I tell myself that every single day. If something gets hard, I just won't quit today. I wake up the next day and I just tell myself, I just won't quit today. Because not giving up is the most heroic thing you can do. You've got to come up with some kind of personal heuristic for yourself to keep yourself in the game. People say, oh, it has to be about having a bigger why. My children are my why. Making $55 million is my why. Like, none of that means anything to me. Because when things get really difficult, you want to quit. And sure, you may do it for your children. But what if you're tired? What if you had a fight with your wife? What if your business partner screwed you? What if you're like, man, I don't want the $55 million anymore. I just want my piece back. What if all of those happen? The whys are very interesting because they're very negotiable. To me, I want the non-negotiable thing. It's a simple heuristic that allows me to win every single day. And if not giving up is the most heroic thing you can do, the heuristic that I have is I will not give up today. And I say that to myself every single day. That's number one. Here's number two. If you have a business, I want you to really internalize this. When a business sells, it is valuable. It's valued on a multiple. So if you have a $5 million business and you make $1 million in EBITDA or profit, you probably are getting a four times multiple. I'm just making it up. So 4X, well, small companies get small multiples and big companies get big multiples. All right? So a $5 million business with $1 million EBITDA will probably get a four times multiple based on the industry. It should go with the idea. But a $15 million business. With $3 million of EBITDA would get a significantly higher multiple. Now, the EBITDA ratio from gross profit to, I'm sorry, from revenue to profit is probably the same. But the multiple that you get is significantly higher. So imagine if for $3 million of EBITDA, you get 10 times multiple. But for $1 million EBITDA, you only get a five times multiple. Well, that's crazy from a thinking perspective. That is, it's not even in the same ballpark. Right? There should be a lesson here for all entrepreneurs, which is you want to build the biggest possible business. There's zero reason to play small. You should not think about having one auto body shop. You should think about how you can get 10. You should not think about one restaurant. You should think about how you get 10. You should not think about having one coaching program. You should think about how you get 20. You should not think about having four good clients. You should think about having 40. Right? And I'm not telling you that, you know, it's going to change your life to do that. I am saying that small companies get small multiples. And big companies get big multiples. I say this because having run a couple of different small businesses and having run $2 billion companies, I will tell you the determining factor was just figuring out that when you have a smaller company, you have a smaller multiple and a bigger company will get a bigger multiple. That is lesson number two. Here's lesson number three. Every business needs a competitive advantage and you know, people call that the moat. If you don't know what a moat is, it's like, uh, you know, in the traditional old days, there's a, a, a. A. A. Little, uh, uh, little bed of water around a castle and that prevented had crocodiles and whatever. And it prevented people from entering the castle without the drawbridge. Right? Well, what is a moat? A moat is where you can get massive effort on the front end. When you get massive effort on the front end, that's when you can start making money because the money is a elegant business model on the backend. So let me explain what that means. The moat is massive effort on the front is very hard to build. A moat like that, right? So what do you need to do to build a moat? You need to dig and trench around this castle that you're thinking about building, and then you need to go build a castle. So building the moat is hard work, but once you build it one time, no one can beat you. I'll give you an example for like content, right? So if you're thinking about making content in the world, well, you make a lot of volume, a lot of content. There's a massive effort on the front end, but once you have made it, once you're famous, once you have 5 million followers. Once you've done that, you're automatically a winner. You've created the moat. You can, you can reuse that moat over and over again, because, and then based on that moat based on that moat, you can then create an elegant business model on the backend. That's why you have a lot of quote influencers these days who will spend all the time, all the effort, all the money on the front and trenching this moat. And once they have the moat, they will be able to create a business model on the backend. I'll give you an example of, uh, I had this idea early on and I was like, how do I build a moat? And I didn't know what to do. So I thought, how amazing would it be to have an email list? This was before email lists were even a thing. Right. And I started doing speaking engagements and, um, I would say, Hey, my speaking engagement fee was at that time at that $10,000. And I said, by the way, uh, since you're a friend or you're a first time client or whatever, I would, I'd be happy to waive the fee for you. Uh, I'm assuming you have no problem sharing the invitee or registration list with me. So wherever I would go to present, I would just trade my fee for the registration list, which the organizer are happy to do. And then that is how I started building my email list. So if you're considering this some way, and you are speaking on other people's stages, you can say, Hey, my fee is blank and you can waive your fee to build your list. And if you did that, I don't know if you did that 20 times. Now you have a 2000 person email list for every hundred people that came on a zoom. Those 2000 people is starting to build your moat. And once you have the moat is very, very hard for anybody to displace you. A moat is massive effort on the front end. And then you create money by having an elegant business model on the back end. But if you, once you have a moat, you can do whatever you want to make the money. So that is lesson number three. Here's a lesson number four. It's not about the exit. It's about the options. And what do I mean by that? I've had a chance to sell five different companies, two of them, billion dollar businesses, one privately traded, one publicly traded on the NASDAQ. And the crazy part of this is. Everybody wants. I want to sell their business. So when I talk to somebody, oh, I want to sell my business. Well, sure. But you don't want it to be about the exit. You want to be about the options. Meaning if you will go to market and you wanted somebody to buy your business, they may value it at a certain level. Well, how is it worth more? Well, the only way it's worth more is if you have more options, if you don't need to sell, well, if you need to sell, that number is actually worth less because they're going to detract from the value. You want to value adder, not a value detractor, right? So the more. Options you have, the more value there is. So if I, if somebody, if Google offered me a hundred million dollars or a business business that I built and I didn't need to sell now, Google, if they really wanted the business, they have to pay me more. They have to pay me more than all my options. So our job is not to build a business to sell. Our job is to build a business where we have a lot of options. The option where you can step out of the business and still have it print money for you. The job where you can sell a part of the business and take some money off the table. The job where you can maybe potentially sell the business to Google outright. When you think about how it's not about the exit and it's about the options, it changes the way you come about it. think about everything. So that's lesson number four. Lesson number five is, as soon as I realized this lesson, it changed my life. And this is the one lesson that I teach my children. And if I teach my children, it's probably good enough for year two, which is everything in life has a playbook. I am a strong believer that everything in life has a way to win. And I call that the input output equation. So if you want to do something, if you want to get a result, the output, all you have to do is figure out the inputs to get the result. Well, what does that mean? If you want six pack abs, there is a formula to get six pack abs, right? You eat right, you exercise, you sleep well, you take some supplements, whatever. But there is a formula. You can go to a fitness coach or a weight loss doctor or whatever, and they will give you a protocol. They will give you a playbook. And if you actually were disciplined enough to follow that playbook, you will win. If you believe that there's an input out, there's an input out, there's an input out, there's an input out, there's an input out, everything in life, it makes life significantly easier. And I will tell you the craziest part. Most of the playbooks that you're looking for in your life are available publicly. Now, there may be a small percentage like that you don't know that is available privately, but even that is available for a small fee. And my son wanted to learn how to do the Rubik's Cube. And he was trying to do this online, watching YouTube videos. And in one of the videos that he watched, he saw that there was a, the person that made the Rubik's Cube, he saw that there was a, the person that made the video on teaching how to do the Rubik's Cube was offering private tutoring. And so I looked at it and it was $200 an hour, right? So my dad, my son was like, hey, dad, do you think I can get an hour of coaching from this guy? So I literally messaged this guy on Instagram and he did a one session. He did one session for $200 with my son. And my son instantly was able to get through all the blocks to solve the Rubik's Cube. Now, my son can solve a Rubik's Cube in like 14 seconds. He was interested, but he got a coach associated with it. But he didn't know how to do it. He didn't know how to do it. He was there to build an input output equation for you. I will tell you, almost every goal that you have in life, there is somebody there that has already done it or has the path on how to do it. And the fee that they need is so small compared to the goal that you want to achieve. So small. And most of the time you don't even need it. Like you don't even need it. I'm giving you the playbook for so many things. You don't even need it. Most of the information that you need is probably available through AI or in a free domain that gives you the exact playbook. Your job is to take and collect and curate all this information and build a playbook for yourself so that you know this is the input to get the output that you want. All right, that was lesson number five. Lesson number six, don't risk the empire for a pot of gold. Don't risk the empire for a pot of gold. As you build something important in your life, maybe your family, maybe your relationship with their children. Man, that car is just ripping it. It's crazy. This is why you drive a Tesla. No one can even hear you coming. Maybe your family, maybe your friends, maybe whoever, maybe your business. You want to make sure that the empire that you're starting to build, sometimes empires start small. Every empire starts at zero. You don't want to risk the empire for a pot of gold. You don't want to risk the empire for a novel new idea. And that is a reputational risk that can crush you. There's this guy, Dr. Peter Attia, I believe. He was a well-renowned health expert. I had multiple people pay him $100,000 to go do a one-day kind of health retreat in his offices. As soon as Peter Attia's name came out in the Epstein files, he lost his entire business. Now, that's sad. We don't know the details, et cetera, but he risked the empire for a pot of gold. You may say, hey, I'm going to go bet on this client and this one client, and I'm going to neglect all the other clients. Well, because this client may be a big, big opportunity for me. Well, you're risking the empire for a pot of gold. In your personal life, I actually had a friend who, I'll tell you the truth, he ran their mortgage company. I know his personal net worth is over $75 million, which is extremely meaningful. And he cheated on his wife. Well, he risked the empire for a one-night stand, right? Now, it's bad enough that that's wrong, and it's against your marital vows. But even from just a straight risk perspective, he lost half his company and had to sell parts of his business to actually pay it out. Even in the business, there are risks that you can take. So if you're like, man, should I actually let go of this person? If you have an A player that is now saying, hey, they need a 10% more bump because they just had a child, or they have to move to work with you, and they can't work in your office anymore, and they need a remote job, you're risking the empire for a pot of gold. Just pay them the pot of gold. Sometimes I ask myself this question when I'm investing in something, and I feel like it's risky. I'm like, hey, am I risking the empire for a pot of gold? Last but not least, lesson number seven, keeping all this straight in my head, is the world will give you whatever you ask for. You just have to ask for it intelligently. That is a fancy thing that someone will say, well, what does that mean? I think that forces me to think about what I'm actually asking for and whether it's reasonable. So this makes me, if you heard the phrase, oh, you know, little Jenny deserves being on the golf team, or Kobe deserved the rings that he got, or Michael Jordan deserved, you know, the success that he had, or Tiger Woods deserves the success he had, or Oprah deserves the success she had. Like, what does that mean? Right? It means to me that if somebody deserves something, I had to, I wanted to be the one that was the deserving of that. What does deserving mean? If you can understand the definition, and you can be deserving of whatever you want, the world will give it to you. That is asking for it intelligently. So here's what deserving means to me. And I thought a lot about this, actually, for multiple years. And I came up with a definition for deserving. When I run my life through this definition, if I don't get something, I feel like I'm not deserving of it. Deserving is having unreasonable effort, but having a reasonable expectation. Okay? Having unreasonable effort, but a reasonable expectation. So if little Jenny was getting on the golf team, and, you know, little Jenny deserves that. Well, you know why you say she deserves that? Because she took private lessons four times a week. She practiced with the golf team every single day. She hit balls at the driving range, you know, four times a week. She did a golf simulator. She trained. She, you know, she watched game tape. What did she do? She put an unreasonable effort. And what was the reasonable expectation? That she would make the golf team. So I've started to think about how can I rebuild my life with that one thing in mind? If you believe that you want something, the way you're going to get what you want is if you ask for it intelligently. And the way to ask for it intelligently is to just be deserving of it. And now you know the definition for deserving. For you to be deserving of the love from your spouse. And if you're like, man, he doesn't love me. She doesn't love me. You're not deserving of it, right? Because if you're deserving of it, you would get it. Well, what does deserving mean? You need to show unreasonable effort and have reasonable expectation. If you did you would get what it is. If you wanted to build an amazing YouTube channel, right? It's like I deserve to have a million followers, million subscribers. Well, if my reasonable expectation is to have a million subscribers, my unreasonable effort would be that I would spend 400 hours a day doing this. Because I know that if I spent that unreasonable, again, clearly, I'm joking, you don't have 400 hours a day. But my point is, if you create an unreasonable effort standard, you're like, man, I did all of this. It's only a matter of time in this input-output equation for me to get that result. Unreasonable effort with reasonable expectation. And I think everything in the world can be hacked with just that. Because you can just say, I'm not getting the thing because I'm not deserving of it. If I just need to be deserving of it, I need to have unreasonable effort with reasonable expectations. And if you just kind of create that dichotomy and you know what you want, it is so much easier to get what you want. And the only way to do that is you can't be deserving of a lot of things. You're not superhuman. You're not Zeus. You're a few things. And to be deserving of those things, you have to have unreasonable effort and reasonable expectations. Now, my question for you is this. It took me 30 plus years. And having built $2 billion companies, having lost everything that I have multiple times along the way, having done 100 plus deals, having lost millions of dollars of my personal money, having built a social brand, having built an email list, having invested in 100 plus businesses. These are the lessons that I wish I had learned when I started out. And I hope that these end up being clues for you. Because success leaves clues. And I hope one of these is a great clue for you to have a great life. So be deserving of that life.

Podcast Summary

Key Points:

  1. Not giving up is the most heroic thing you can do—this became a personal mantra after recalling a dumpster-diving experience in college, which later symbolized resilience and perseverance over 22 years.
  2. Building larger businesses yields significantly higher valuations; entrepreneurs should aim for scale, not small operations, because bigger companies earn bigger multiples based on profitability.
  3. A competitive advantage (or "moat") requires massive upfront effort—such as building an email list through speaking engagements—that becomes a lasting asset, enabling recurring revenue through an elegant business model.
  4. Success isn’t about the exit, but about having multiple options—like the ability to exit, sell parts of the business, or scale independently—because more options increase long-term value.
  5. Every goal has a playbook or input-output equation—whether it's fitness, skills, or career—and most of these are publicly available, so the key is to find, collect, and apply proven strategies.
  6. Never risk your core empire (family, business, relationships) for a single opportunity—doing so creates reputational or financial collapse, as seen in real-world examples of personal and professional failures.
  7. To get what you want, you must be "deserving" defined as showing unreasonable effort with a reasonable expectation—this mindset shifts how you ask for success and aligns your actions with outcomes.

Summary:

The speaker shares seven life lessons learned through decades of entrepreneurial success and hardship, emphasizing resilience, scale, and strategic thinking. He begins with the powerful idea that not giving up is the most heroic act, rooted in a memory of surviving financially as a college student through dumpster diving. This experience became a symbol of perseverance, reinforcing a daily personal commitment to not quit.

He stresses the importance of building large-scale businesses, as they attract higher valuations due to greater multiples. A key competitive advantage—called a "moat"—requires heavy upfront effort, such as building a massive email list through speaking events, which later enables sustainable revenue. He argues that business value isn’t about exit, but about having multiple options—including flexibility, partial sales, or independence.

Every goal has a playbook, and most are publicly available, so the key is to learn and apply proven input-output models. He warns against risking your core life or business for a single opportunity, citing real cases where reputational or financial collapse followed. Finally, he defines "deserving" as showing unreasonable effort with a reasonable expectation—such as dedicating intense time to mastering a skill or relationship—leading to greater chances of achieving desired outcomes.

These lessons, drawn from building $2 billion companies and enduring financial losses, serve as practical guidelines for anyone seeking a more resilient, purposeful, and successful life.

FAQs

The first lesson is that not giving up is the most heroic thing you can do. The speaker shares how, as a college freshman, he dumpster-dived for food and later returned to that same dumpster during a commencement speech, where he found a poster with the quote, which became a personal mantra to stay resilient through difficult times.

Big businesses earn significantly higher multiples in value compared to small ones because market valuation scales with size. For example, a $15M business with $3M EBITDA gets a much higher multiple than a $5M business with $1M EBITDA, emphasizing that entrepreneurs should aim for scale to maximize long-term value.

A 'moat' refers to a competitive advantage that requires massive upfront effort to build, making it difficult for others to replicate. Once established, it allows a business to generate recurring revenue through an elegant, sustainable business model on the backend.

Focusing on exit value is misleading—businesses are more valuable when they have multiple options, such as generating passive income, selling part of the business, or selling to a major company. More options increase long-term value and flexibility.

The speaker believes every goal has a playbook or input-output formula. By identifying the necessary inputs (like effort, habits, or training), you can follow a clear path to achieve results, and most of these playbooks are publicly available or accessible through AI and free resources.

You should never risk a stable foundation—such as a business or family—on a single opportunity. The speaker cites examples where individuals lost everything due to personal risks like infidelity or betting on one client, emphasizing that such actions endanger long-term stability.

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