What happens when you retire from the family business… but your brain refuses to stop building?

This week on Coffee & Grit, 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 have been sitting in your head for years.

Todd spent decades in the family dealership business before stepping into a completely different season of life after the business sold. Instead of slowing down, he found himself diving headfirst into writing, game creation, fantasy football formats, and building something he genuinely wished existed himself.

And honestly… that’s what makes this episode great.

This is a real conversation with real stories about testing ideas, taking expensive punches, learning from setbacks, listening to feedback, and continuing to move forward anyway. We talk about:

• What happens after the family business chapter ends
• Why most people never pursue the ideas they keep thinking about
• The hard lessons of app development and entrepreneurial pivots
• Why Todd completely reimagined fantasy football
• Creating fantasy football formats without drafts and with stock-market style player values
• The importance of listening to customer feedback without taking it personally
• Turning passion into a business opportunity
• The difference between having ideas and actually executing them
• Why action creates clarity faster than overthinking ever will
• Leaving your worries at the “worry tree” before walking into your home

One of the biggest themes throughout this conversation is simple: Just make it happen.

Todd openly talks about building things before having all the answers, learning as he goes, making mistakes, pivoting, and realizing that the only way to know if an idea works is to put it into the world.

And beneath all the fantasy football talk is a much deeper message about reinvention, creativity, and refusing to let curiosity die just because one chapter of life ends. Because sometimes the next thing you are supposed to build is hiding inside the thing you’ve loved your whole life.

If you are someone with ideas sitting in your head, a business you keep talking yourself out of starting, or a creative itch you have been ignoring… this episode will hit home.

Connect with Todd Bailey & Extreme Fantasy Football 🏈 Website: ExtremeFF.com
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