Super proud of HoldCo Conference 2025. Some great insights & recaps here.

1) Go to VRBO / Airbnb 2) Find a rental you like. 3) Identify the property manager firm in listing 4) Google firm name 5) Book property on their website 6) Save $400 Every. Single. Time.

I write a letter to business owners every Saturday morning. Get on the list! https://t.co/u1p2gk5bO0

It does feel like "let me pick up the phone and call them" is becoming a lost art in business. Instead, you get dozens of emails or Slack threads that go on forever. Or if you hate life, Microsoft Teams.

RadioShack, Circuit City, Fry’s—these were all electronics chains that died in the 2000s. Well, there’s one guy still standing: Best Buy. How the hell did that happen? The story of how they managed to survive in an age dominated by Amazon, Walmart, and other retail giants is a

1) Go to VRBO / Airbnb 2) Find a rental you like. 3) Identify the property manager firm in listing 4) Google firm name 5) Book property on their website 6) Save $400 Every. Single. Time.

My best health pro tip is to order kids' meals when eating out. It's the only way to get a normal-sized portion outside of the home these days. Bonus points when the staff looks at your 6'5", 230lb self, funny.

Lots of talk about networking lately, so my best advice on this topic is: The best "networking" is building and doing great things. Greatness attracts greatness.

Buying a Business in 2026, with Chelsea Wood

I write a letter to business owners every Saturday morning. Get on the list! https://t.co/u1p2gk5bO0

PRO TIP: When talking to your Canadian friends, refer to their country as "Really North Dakota." They love it.

There is a small business equivalent of "Don't fight the Fed." (This phrase basically says investors shouldn't go against what the Federal Reserve wants to do as they manage the cost of money.) Anyway -- The Feds also make policy that can and will affect your small business.

This lecture is the surest sign that the best opportunity right now is to create assets. Go build something from scratch, people.

Update: he was an hour late.

My life advice is to avoid any job where you’re on your laptop in the lodge on a Saturday while your kids are skiing.

My #1 most attended lecture was (1) back when my X account was really cooking and (2) about incubating new businesses. We had about 1500 signups. This has blown that away. Lots of capital and people chasing opportunities.

The best 3-minute argument for aggressively curating your personal network.

It is shocking how many people go through an entire interview process of screening calls, then no-show for an in-person interview. No call. No text. Just straight ghosting, and you never hear from them again.

Early in my career, I did a stint at a cybersecurity vendor. The result of seeing how the sausage was made? I don't have any cameras, smart home, or smart speakers in our house. If it can be analog, we do it. Later in my career, I've gotten to know a ton of people. The result?

Back in the 1980s, some of my ancestors borrowed money to buy the land I'm sitting on as I write this. The interest rate was 15%. Money was hard to come by, and it was expensive. Fast forward 40 years, and we're at the other end of the spectrum. Eighty years of post-war wealth