Don't Shine the Turd

At Golf.com, I (Mike) was on a board call presenting our sales results. They weren't great. So I did what a lot of founders do. I put an overly positive spin on them...

Jul 15, 2026

Guard Your Culture With Your Life

At 25 employees, I (Kass) noticed something was off. A few veterans had started forming cliques. Inside jokes that excluded new hires. Lunch invites that didn't exte...

Jul 1, 2026

The Co-Founder Trap

I (Mike) raised $12 million to bring the brilliant Shape Matrix technology to market. With one of the smartest crews I've ever worked with, including a former FBI ag...

Jun 17, 2026

One Year of Shoveling $h!t

A year ago today, our book dropped. The results have been overwhelming. Yes, the book has been honored in ways we never could have imagined. An instant hit and New Y...

Jun 6, 2026

Why Great Founders Fire Faster

At Golf.com, we hired our first salesperson. Let's just say he was no superstar. He was a nice guy. But he wasn't closing deals. The only thing he successfully sold ...

May 20, 2026

The Case for Radical Transparency

Early at Buddy Media, we made a decision that felt risky at the time: tell people the truth. All of it. Not the polished, PR-approved version. The real version. When...

May 6, 2026

Know When to Pivot

We pivoted Buddy Media three times before it worked. First, we built a social network for brands. Killed it. Then, a Facebook app builder. Killed it. Finally, we lan...

Apr 22, 2026

Choose Your Cofounder Like Your Spouse

"I Wish I Had" Verses "I'm Glad I Did" There are two kinds of people at the end of their lives. The first group says, “I wish I had.” I wish I had taken the shot. I ...

Mar 25, 2026

Numbers are Boring... Until They're Not

We started our first company together in 1998. We were dating. Not even married yet. No playbook. No investors. No idea what we were doing. About a year in, we were ...

Mar 11, 2026

Love the Shovel

Let’s talk about side hustles. It’s never been easier to start a business on the side. And that’s a terrible reason to start one. Last year, SurveyMonkey reported th...

Feb 25, 2026

Rip Off the Band-Aid

AI Without the MigrAIne. Everyone is talking about AI. It’s everywhere. It’s loud. And if you’re a small business owner, it probably gives you a migraine thinking ab...

Feb 10, 2026

Own Your Origin Story

Your origin story is not a marketing fluff piece. It's the single clearest signal of who you are, what you will tolerate, and who belongs on your team. Craft it care...

Jan 28, 2026

Eat Your Own Dog Food

The best leaders eat their own dog food. They don’t just sell the thing. They live inside it. They feel the friction. They discover the flaws. Most people outsource ...

Jan 14, 2026