Appearance on the Founder Brand Podcast with Finn Thormeier
What do Jack Daniel’s, Robert Service, and David Ogilvy have to do with founder branding? A conversation with Finn Thormeier about staying in character, staying on message, and building a senior audience without writing for the algorithm.
What the heck is a Jack Daniel’s ad doing in a post about a podcast appearance? Good question.
The answer: I think this is one of the greatest (and longest-running) brand advertising campaigns ever created. Postcards from Lynchburg by Ted Simmons for Jack Daniel’s. “We’re not selling a bottle of booze, we’re selling a place.”
And if branding is about trust, trust is about character. Specifically, defining and then staying in character. No series of brand advertisements ever did it better.
So, naturally, when someone invites me to a podcast called Founder Brand, we’re going to talk about Jack Daniel’s.
And we’ll also talk about English-born Canadian poet Robert Service, known for his colorful tales that captured the adventure, hardship, and rough humor of the Klondike gold rush.

Service unknowingly created one of the best reminders for founders (and marketers) who all too often get bored with their own message, long before most of the market has even heard it:

That’s from The Men That Don’t Fit In, a rollicking but pointed poem about the consequences of endlessly chasing the next big thing.
David Ogilvy offered a complementary reminder for marketers:
“You aren’t advertising to a standing army; you are advertising to a moving parade.”
So, of course, if you get me going about branding, we’re going to talk about all that. And Finn Thormeier did a great job of getting me going in our interview.
In the interview, we hit on:
- The origins of Kellblog
- The meeting with Ben Horowitz that taught me, the hard way, never to write for the algorithm
- How to build an audience of senior executives—and why chasing a bigger audience can cost you the one you have
- Why most thought leadership isn’t
- How to build an executive brand that helps your company without looking like you’re just promoting yourself
- Why personal branding starts with distilling who you are—and listening to how the market perceives you
- My writing process, including notes, outlines, and AI
- How to reach your audience in a world of increasingly walled gardens
- How to think about fad surfing vs. writing on topics of lasting importance
I hope you have time for a listen. This was a good one. Thanks, Finn, for doing the prep work that let us get deep on these topics.