06/01/2026
Here It Is The Official Kick off to Your week with Coffee & Grit!
Listen in as I sit down with Todd Bailey for a conversation about entrepreneurship, reinvention, creativity, fantasy football, app development, and what it looks like to finally pursue the ideas that never stop pulling at you.
Todd spent decades in the family dealership business before stepping into a completely different chapter of life after the business sold. Instead of slowing down, he started building again—writing books, creating games, developing fantasy football formats, and turning lifelong passions into new opportunities.
And honestly… that’s what makes this episode powerful.
This is not a polished “everything worked perfectly” startup story.
It’s a real conversation about:
Taking action before you have all the answers
Learning through expensive mistakes
Listening to feedback without taking it personally
Pivoting when the original plan doesn’t work
Building something because you genuinely wish it existed
And realizing that curiosity and creativity don’t have to die just because one chapter of life ends
We also get into Todd’s vision for Extreme Fantasy Football, including fantasy football formats without drafts, stock-market-style player values, app development challenges, and why he believes fantasy sports can be way more engaging than the traditional model.
But beneath all the football talk is a much deeper message:
Sometimes the next thing you are supposed to build is hiding inside the thing you’ve loved your whole life.
If you are someone sitting on ideas, second-guessing yourself, waiting until everything feels “ready,” or wondering what your next chapter looks like… this conversation will hit home.
🎧 Episode 255 of Coffee & Grit is live now.