Don't Argue with the Market

It is easy to spend months falling in love with your own product. You refine the features. You build the pitch deck. You convince yourself that everyone will want wh...

Oct 7, 2026

You Don't Need to Do It All

All entrepreneurs know that there is always more we can do. More customers. More products. More ideas. More opportunities. The challenge is figuring out what actuall...

Sep 23, 2026

Don't Worry, Be Crappy

When we launched Buddy Media's first product in 2008, our software sucked. It was buggy, basic, and missing most of the features we wanted. A perfectionist would hav...

Sep 9, 2026

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