For a stretch, I kept losing deals I was sure I’d win. Great calls, real interest, people telling me they loved what we do. Then I’d send the proposal, and it would go quiet. When you lose that many in a row, you stop blaming the prospects and start looking in the mirror. That’s how
Why My Proposals Were Losing, and What I Changed Read More »
When you’re building a service business, every inquiry feels like oxygen. So saying no to clients feels insane. Why would you turn down money? But I’ve learned that some of the most important decisions I’ve made in my business were the times I said no, and some of my worst were the times I should
Saying No to Clients Is the Skill Nobody Teaches You Read More »
I’ve watched business owners kill their best marketing over and over. Not because it stopped working. Because they got bored, impatient, or nervous right before it started paying off. Quitting marketing too early is one of the most expensive mistakes I see, and it’s almost always invisible to the person making it. I recorded a
Don’t Quit at Forty: Why Business Owners Kill Their Best Marketing Read More »
Playing the World Series of Poker was on my bucket list for years. I finally went. I played 14 tournaments. I didn’t cash in a single one. And I came home more disappointed in myself than I’d been in a long time, not because of the cards, but because of how I showed up. This
What Playing the World Series of Poker Taught Me About Preparation Read More »
In the same year, I scaled my team up and then scaled it back down. I added services, then cut them. If that sounds messy, it was. Scaling a small business is one of those things everyone talks about like it’s a straight line up and to the right. Mine looked more like a heart
I Scaled My Team Up and Back Down in One Year Read More »
In September 2025, I got the keys to a space that would become the All In Content Studio. It was the biggest business risk I’d ever taken. A real lease, a serious investment to build out four sets, and a bet that it would change the direction of my company. Some of that bet paid
The Studio Was My Biggest Gamble. Here’s What I Learned Read More »
My first business failed. Not in a dramatic, public, crash-and-burn way. It failed quietly, which is almost worse. It stopped making money, and then it sat there for years, costing me money while I avoided dealing with it. The lessons from a failed business like that aren’t the ones you see in motivational posts. They’re
My First Business Failed. Here’s What It Taught Me Read More »
People are always a little surprised when they find out how seriously I take poker. They shouldn’t be. Poker and business have so much in common that I honestly think the table has taught me more about running a company than most business books have. I’ve played for years, including at the World Series of
What Poker Taught Me About Running a Business Read More »