From Football to Futurism with Chris Doelle

"Be afraid, but go anyway." Texas polymath Chris Doelle shares how curiosity, creativity, and persistence took him from cinnamon toothpicks to podcasting's earliest days, AI strategy, and even board games that bring legendary football teams to life. This episode is sponsored by my new book BRANDJITSU, helping you find, shape, and share your story with the world. In This Episode In this episode, Michael chats with Chris Doelle — one of the original podcasters and a serial entrepreneur whose career spans media, sports, AI consulting, and game design. Based deep in the heart of Texas, Chris has been launching projects for decades, often long before the market is ready for them. Chris recounts how he jumped into podcasting in 2004, creating multiple shows in the first week, and stuck with it for a decade before it became profitable. He shares why he believes podcasting should be the cornerstone of any content strategy and how every business — from plumbers to pro sports teams — will soon be a brand. The conversation covers his ventures into AI and automation, including agentic workflows that can accomplish in minutes what used to take weeks. Chris also tells the story of Friday Night Legends, the board game that lets fans pit real high school, college, and professional football teams from any era against each other — a project born from his deep love of sports storytelling. Michael and Chris swap stories about creativity, side hustles, and the strange perks of homemade media passes, from press box access to free food — even sneaking into the Super Bowl. Chris's philosophy is simple: try everything, say "yes" to the interesting stuff, and don't let fear or doubters get in the way. From Texas barbecue to breakfast taquitos made from fridge leftovers, from barefoot mornings with chickens to speaking on AI's future, Chris proves that a curious mind and a willingness to act can build a life that's anything but ordinary. Quotable Quotes "Find cool things you like to do, and then see if there's a way to monetize it." – Chris Doelle "Be afraid, but go anyway." – Chris Doelle "My life philosophy is to do cool and weird stuff with cool and weird people." – Michael Dargie "Don't assume you can't do things. The only way to fail is not to try." – Chris Doelle "Everyone will become a brand." – Chris Doelle Episode Highlights Podcasting Pioneer | Launching six shows in 2004, long before it was profitable. Branding for Everyone | Why every business will be a personal brand. Agentic AI | How automation can now do in minutes what used to take weeks. Friday Night Legends | Turning real football history into a playable board game. Media Pass Perks | From free food to the Super Bowl with homemade credentials. Texas BBQ Philosophy | Why Central Texas salt-and-pepper brisket reigns supreme. Daily Ritual | Barefoot mornings, chickens, and breakfast taquitos with whatever's on hand. Rebel Advice | Be afraid, but go anyway. Don't let other people's voices in your head stop you. LINKS FROM EPISODE Fresh Media Works (https://www.freshmediaworks.com/) Chris on LinkedIn (https://www.linkedin.com/in/chrisdoelle/) Chris on Instagram (https://www.instagram.com/chrisdoelle/) Chris on Facebook (https://www.facebook.com/chris.doelle/) Threads (https://www.threads.net/@chrisdoelle) Chris on TikTok (https://www.tiktok.com/@chrisdoelle) Chris on Twitter (https://twitter.com/ChrisDoelle) Get Your Copy of Michael's Book: "BrandJitsu™: Move Your Brand From 'Meh' To Memorable" Indigo | Barnes & Noble | MichaelDargie.com