I once presented a billionaire some of the highest-ROI projects I'd ever found. Some north of 1,000% IRR. I have never forgotten his response.

A week or so ago, I dropped my son at the baseball field. I parked the car, grabbed my chair, and headed to the bleachers. On my way, there was a dad - Tom - setting up his own chair along the first base line. I knew Tom - our sons had been on the same team a couple times but we weren't close. He is a very talkative guy, very friendly. Always excitable. But after a hectic morning, I was ready to sit in silence for a few minutes before the game started. So as I saw him setting up, I knew he would want to engage and frankly, I dreaded it. I walked by him, said "hey Tom", and tried to keep some momentum, hoping he would only reciprocate. But Tom, who is always energetic, was extra today... to say the least. We talked for what felt like an eternity (probably a minute and a half) but he would just not let go. Nothing much to say just a crazy energy and nonstop banter - the weather, baseball, how great everything is and so on... Incredibly positive. Actually, annoyingly positive. Eventually I was able to wrench myself free. I headed to the bleachers for my well deserved 30 minutes of mindlessly scrolling my phone. We lost the game (bad) and I went about my day, distracted with consoling a 10 yr old. I had forgotten all about that ballfield interaction until about a week later my wife got a call from Tom's wife. We live nearby and she needed help getting her son to baseball, she explained. Tom - my ballfield conversationalist - had to leave for a while. His dad was dying and he needed to help his mom. Of course my wife was happy to help a neighbor in need. She hung up the phone and made a note in her planner. But then the phone rang again - Tom's wife was calling back. "Hey I just wanted to tell you- that's not the full truth. yes, his dad is sick but I asked him to move out. He hasn't worked in two years and he is not in a good place and it's having a terrible impact on our family." My wife dug in, ready to help even more. Later that day, she told me about these conversations. I immediately thought back to that conversation with Tom at the ballfield. I had been so anxious to get away, so focused on myself, I had completely missed someone desperately in need. A dad dying, a career imploding, and family struggling - for a man, I cannot imagine a worse combination. I have thought about that conversation and my self absorption everyday since. You just never know what someone is going through. It's of course impossible to know at the time, but you can be confident in this: everybody is going through something. My favorite definition of humility is from C.S. Lewis: Humility is not thinking less of yourself, it is thinking of yourself less. If you want a picture of what that might look like, read Theo of Golden. It is the story of a man who embodies that almost perfectly. Tom is still "away" right now. We are doing every small thing we can to support his family, but I will always regret that ballfield conversation.

Don't just take it from me...

The older I get and the more I read, the more I realize most of success comes from working harder than others. Outworking. Embracing the pain. Yes the super successful catch some breaks but their stories start out with hard work and not knowing the outcome (and actually often quite a bit of bad luck). But they persevere. They keep working hard in the face of calamity. Most people don’t realize they’re not working hard until they see someone next level. Here’s an analogy… I’m frequently on the road. As a result, I sometimes use hotel gyms. (Normally I use my home gym which I love thanks to @homegymcoop and @DeanTTraining.) But at the hotel gym it is obvious why people who “workout” everyday don’t look like it. Not working nearly hard enough. Going through the motions 3 sets of 8 reps, never a rep in question and on to the next machine. This was me, btw, at one point. Going through the motions. But I learned from some of the best lifters in the world- watched what they did. And now? I am working my absolute tail off. My last rep of a set is often so excruciating. I’m not sure I’ll complete it. Sometimes I don’t. Walking around listening to music in a room with weights is not working out. True in life too. Showing up is not enough. You’ve got to outwork others. And you’ve got to get yourself in a position to see what the elite are doing. Then mimic it. But by far the easiest way to differentiate is to work harder. Harder than you are now. Increase intensity and duration. That will open doors into new rooms. Once you are in the room you repeat. Push to the max. That’s the only way to ensure you are getting everything you can out of it. That leads to the next room. Point is, there is more and better available to you. The progress you are looking for is in the next 1%. And most people won’t get it. Because that next 1% is hard.

Some strong opinions on this one. Here's how I actually use it: When evaluating ideas: the best ones - "clear yes's" - are usually supported by one clear reason. When presenting ideas: don't cloud the rationale with multiple reasons when one will suffice. When you hear multiple reasons, consider it yellow flag. It's not a "no" but it probably isn't a clear yes. Investigate.

The other day I was talking to a guy trying to sell his business. He said, “you can trust me, I’m an Eagle Scout.” He’s 40. How would you interpret this? Red flag?

Gen Zers don’t get it. “Everything gets worse as soon as it’s bought by private equity.” That’s the sentiment of this article (and a direct quote). Can’t they see the restaurants are actually better? Don’t they appreciate the new branding? The iPads instead of clerks? The brighter lighting? More locations? Yeah, the meat changed a little but so what? It’s still the same name on the door. These people just don’t get it. PE is making things better for them. Why can’t they see that? When they can finally afford to buy a house they will realize that PE owns HVAC and has made that way better too. Now when the HVAC guy shows up to my house, he doesn’t waste time knowing my name. I’ve never seen him before and he doesn’t know me. And I like that. I prefer working with a stranger because he has an iPad now and can show me pictures. And I like how every time he comes out I get to spend unexpected money on my system. I mean what else am I going to spend it on? A vacation? Get real. As they age they’ll also see that it’s better when PE owns your doctor’s office. Because now the doctor is more “efficient.” Yes, that means he has less time to spend with me, but that’s better. I mean who wants to spend time talking to a doctor? And no, he doesn’t offer the same services anymore because he told me he needs to focus on fewer, more specialized procedures. (He said something about “profitability” but I assume that’s just medical jargon.) So no, I’m not worried about this health scare I came to see the doctor for. I went to the doctor, checked the block, and I’m sure everything’s fine. And no it’s not frustrating when I do come back (issue wasn’t resolved) because then I get to see a different doctor who tells me I need a different procedure and that’s good. So, these kids complaining about their favorite restaurant. Give me a break. Jersey Mike’s was bought by PE and the data show it has the highest rating among quick service restaurants. Data do not lie. Survey. Third party. You are just objectively wrong, Gen Z. And I’m telling you, when you own a home you’ll love the HVAC experience. And as you age, the healthcare experience only gets better. Yeah they’re more expensive but what’s more important than my health and comfort? I mean, where else am I going to spend my time and money? Lunch at Panera with my friends? Panera sucks now… theguardian.com/food/2026/se…

Elon goes so hard. From @EricJorgenson's Book of Elon. On peoperator.co

It will be amazing if the AI companies’ apocalypse PR strategy totally backfires and they all just end up having to add more expenses via subject matter experts to “monitor safety”

A friend of mine told me this story. I can't get it out of my head. He runs a publicly traded business that is growing like crazy. One of his managers was complaining that her employee was not getting enough done and not getting done specifically what was asked. So this CEO asks her to see the instructions she had provided to the employee. They were OK. Then he asks her to see the instructions she had provided to AI. They were phenomenally detailed. (Notably, the instructions were both given through the same platform). He used that contrast to point out to her that whether she is managing an employee or a bot, the same level of detailed instruction would be more effective. I thought that was brilliant. Today, we are often interacting with AI and humans the same way - through messaging. I'm not sure why, but it's intuitive to give painstaking detail to AI but for some reason we assume humans just "get it." What if a portion of the AI unlock is just that we are providing better instructions to it than we did to humans? It's obviously more than that, but there is something to it.

I have thought about this everyday since I read it. It's now one of my primary filters for evaluating arguments for/against ideas.

Apparently some people don’t think they should have to adapt as the world changes. This is called loserthink. It is a self-fulfilling mentality.

My dad used to have this shirt from the computer company Compaq. A good private equity operator would shut that department down twice.

Added Stock Picker to PEoperator.co - Check it out among other of my favorite books.

I really like Tucker and his message today but this is wrong. You are ready for a family when you decide to be a man. Everyone acts like they need to wait until they mature to settle down. Like there’s a magical age when that happens. It’s just an excuse to continue being a boy. Meanwhile, you and your future wife accumulate baggage that you’ll both have to deal with in marriage. “Oh but I want to have fun in my 20s.” Thats boy thinking. I know. I have four little boys. That’s how they think: I want to have fun. They don’t understand deep satisfaction. Fulfillment. Thats because they’re boys. Marry your high school sweetheart. Or your college one. Settle down. Have kids. Start now. Marriage is a commitment. It requires you to commit. Recognize what it is. It’s not about you. It’s not about your happiness. It’s about giving yourself up for someone else. And counterintuitively, that will lead to your sustained happiness. You don’t have to look for the next party because you are fulfilled in a much more meaningful way. And you will realize quickly those parties never actually made you happy. You probably know that now. If you read that and think, “sounds awful” - you are a boy. Thats what my 5 yo thinks: I don’t want to give, I want to get. But I will spend his first 18 years- his time in my house - showing him that giving is actually where he will find the most sustained fulfillment, “happiness”. And that’s a decision- not some magical maturity you get at 30 or 35 or whatever. Look stuff happens, people have stories- I get it. But believing there is some magical age in adulthood when you are mature enough to commit is a psyop. The truth is marriage is hard regardless of when you start. Same with kids. Anything in life worth doing is hard. That’s why it’s fulfilling. Go for it now. We will all be better off for it and you will not regret it. You will only wish you’d started earlier.

To pile on… except for private equity guys (thin skinned), the people I’ve met have been remarkably encouraging. Great place to build a network and a head of steam for your next chapter.

You should get to know people from X irl. Always fun. I’ve hired three people I met here- all studs. Have seen several deals. Have invested in deals personally backing people I met here. Just met a guy this week- maybe we do some business together. Unreal alpha.

Have been thinking about him a lot after the recent @FoundersPodcast episode. He acquired businesses and let them operate independently. Then when the deal environment turned against him (prices high) he pivoted to integration. Everyone today rushes to integrate. Maybe that’s not the best path. Maybe learning, letting it breathe a bit ensures a more solid foundation. Curious if others have bought and held, then integrated later?

Apple, please acquire.

When I was 30, I sold a business and was thinking about my next gig. I was focused on buying a company. My brother had worked for this PE backed business in town that was totally dysfunctional, but had great bones. So I approached the firm about buying the business. Obviously PE firms usually sell through an investment banking process so chances were slim. But this firm had offered me a job, so I knew them fairly well. Thought it couldn’t hurt to ask. I reached out and they were willing to talk. I soon realized what they really wanted was to understand why I thought I could be a better owner. What they didn’t realize was that the CEO was an absolute narcissist. Anyway, I told them I wanted to buy it and run it the rest of my life, so my time horizon was better suited to this particular asset. That’s meeting one. Meeting two - I should’ve known - would be different. They sent a VP. This was literally the guy who got the position I had turned down a few years earlier. Not sure if he knew that, but we had lunch at a bbq place. He was UVA MBA which he let me know pretty quickly. We talked, I told him why I was excited about the business and that I was a serious buyer who could close. After a few minutes, the 28 yo told me “I just don’t see you as a CEO.” I actually laughed out loud. At the time I had been CFO for a business that just sold for nearly a billion. I mean, maybe he was right but just the brazen insult to my face made me chuckle. I told him thanks for the feedback. Maybe he was right, but if I could buy the business, that would be my problem. Anyway, as you would expect, it didn’t work out for me. For them, it did. They fired the CEO a couple months later and the business started to take off. I had fun kicking the tires and I got the added benefit of some young nerd adding to the chip on my shoulder.