Is this a scam?

A client called me a scam artist. Another got 54 meetings and closed nothing. What agency life taught me about how far to go to make a customer successful.

Sales organization design is boring

Sales organization design is boring but I'm writing about it anyway. Most startup reps aren’t failing because they can’t sell. They’re failing because nobody built the system around them. Here’s what good sales management costs.

Feedback is a gift

Customer feedback expires if you sit on it. How early-stage founders close the loop, keep drifting customers, and treat mad users as a PMF signal.

Arguing With Someone Smarter

AI is eroding switching costs, process power, and specialized expertise. I work through a conversation I had with another founder about whether software still has a moat, and why counter-positioning matters more than ever.

Why your deals are stuck

Stalled deals usually trace back to one sales call. Learn how to own the agenda, map every buying influence, and book the next step before anyone hangs up. (156 characters)

Why I didn't sell (part ii)

I had a follow up conversation with a subscriber that helped me unpack a key mistake I made

My predictable journey

How a side project I didn't care about became the tool that ended my 60-hour weeks, reached 10 paying customers, and why I chose to slow down.

Why I didn't sell

I had two real chances to sell just off our peak. I passed on both, and it cost me five more years in a job I'd already decided I didn't want

Burning a match

Why Early GTM Spend Fails

Your cold email is a lie

Why AI Personalization Sucks

Quiet design partners

I thought bringing folks along with me on the journey would help, I was wrong.

Outbound has layers

Stop waiting

Kill the status meeting

No next steps

The ghost came back

Dots, not lines

Free doesn't hurt

Two hundred dollars

14 years on the rollercoaster

Just Two Hours...

The 5% Problem

The Most Awkward Conversation

Stop asking for sleepovers

How to Sell (for Non-Salespeople)