Gary Club

Insights and field notes

The journal

Working notes on AI agents, automation, and building assets that generate income.

Super Entrepreneurs Podcast episode with Gary Henderson

Five Years Out From Not Working Anymore

Shahid asked me for a prediction that sounds crazy today, and I gave him the one I actually believe: we are five years out from not working anymore. Here is the rest of that conversation, including the physical therapy clinics we rewired, the agent that booked the interview, and why I would tell my son to be a plumber.

Gary HendersonSep 1, 202617 min
AI Marketing episode with Gary Henderson

How an AI Agent Booked This Podcast, and Everything Else It Runs

I went on Mark's show AI Marketing and the first question he asked was how I booked the show. The honest answer is that I did not. An agent named Luna did, and she does most of the rest of the work too. Here is how that came together, what broke along the way, and where I think marketing goes next.

Gary HendersonSep 1, 202613 min
Get Down To Business episode with Gary Henderson

Rent the Attention, Own the Audience

You rent attention on the platforms and you own the relationship somewhere else. That was the through line of my conversation on Get Down To Business, along with why most business owners do not post enough, why buying is emotional, and the divorce attorney comment that changed how I thought about my own business.

Gary HendersonSep 1, 202611 min
Grow With Kepo episode with Gary Henderson

An AI Agent Booked This Podcast, and Then Prepped Me For It

Kepo's first question to me was whether I was even a real person. Fair. My agent Luna had pitched her, handled the back and forth, and read her transcripts before I ever showed up. Here is the full conversation we had about getting your time back.

Gary HendersonSep 1, 202617 min
Success Made to Last Legends episode with Gary Henderson

The Only Bank Balance I Cannot Check Is How Many Days I Have Left

I sat down with Rick Tocquigny to talk about growing up in Southern West Virginia, the moment an attorney told me my profitable business was worth nothing, and why I am building a community where people own a piece of what we make instead of paying a guru every month.

Gary HendersonSep 1, 202614 min
Goal Crazy episode with Gary Henderson

I Trained An Agent To Book Me On Podcasts, And That Is How This Conversation Happened

I have been building automations for twenty five years, starting with a misspelled Hotmail domain. On Goal Crazy I walked Jason VanDevere through how I use AI agents today, why I refuse to hide them, and what I think the time they give back is really for.

Gary HendersonSep 1, 202619 min
The Rishabh Jain Show episode with Gary Henderson

What You Should Stop Doing Manually Right Now

An AI agent booked me on this podcast. That fact does most of the arguing for me. On The Rishabh Jain Show I walked through exactly what I stopped doing by hand, which tools I actually use, and the one question to ask before you touch your to do list tomorrow.

Gary HendersonSep 1, 202617 min