Ryan and Tyler mark 50 episodes of “The Sidekick Life” with their favorite guest moments, biggest mistakes and what's coming next for franchise owners.
There's no guest on the mic this week, just Ryan and Tyler, a cookie and balloons celebrating 50 episodes of “The Sidekick Life.”
Fifty conversations about what it actually takes to leave the 9-to-5 and build a life on your own terms through business ownership. Fifty windows into the risk, the reward and the real numbers behind franchise ownership. So, this week, the hosts turned the mic on themselves to talk about what's worked, what hasn't and where they want to take this thing next.
The guests who stuck with us
Ask Ryan and Tyler to pick a favorite episode, and you'll get a list, not an answer. But a few moments clearly left a mark.
For Ryan, it goes back to a book that shaped the company's identity before the podcast even existed.
"We named the company Franchise Sidekick because of his book ‘Building a Story Brand,’" Ryan said about Donald Miller, the entrepreneur and author Tyler had introduced him to years earlier. “Getting to sit across from him in person turned out to be one of the bigger full-circle moments of the show.”
Other names that made the list were Dr. Jason, the founder of Theragun, whose humility stood out as much as his Rolodex. Paul Reiser of Sonic, who's scaled to 38 franchise locations. And then there was Ryan Hahn, a friend from a former corporate job who took the leap.
"This is a guy I knew back in his corporate job, right?” Tyler said. “This is a guy I knew that he was grinding it out, doing marketing for a big company.”
The ripple effect of watching a friend go from one nervous first franchise to nine locations, more present with his kids and more himself in the process.
That's the thread running through almost every episode. It's not just the big names. It's the founders, the underdogs and the everyday entrepreneurs who prove the model works.
The moments we'd do differently
Fifty episodes in, Ryan and Tyler aren't shy about what they'd change.
Early on, the show leaned too hard into polish.
"We hired a big time company too early,” Tyler said. “We thought we were going to kind of come out of the gate fast. And nothing in podcasting, unless you're already a celebrity, happens fast.”
There was also a content detour that didn't sit right, an episode built more for reach than relevance. They learned the show works best when Ryan and Tyler interview who they actually want to talk to, not who they think will perform. That shift is exactly what pushed the podcast toward its current niche. Early-stage entrepreneurial stories built for the person still sitting at a desk job, weighing whether to make the leap.
More than a mic: Bringing SKIP to life
Some of the show's best moments haven't happened behind a microphone at all, they've happened live at SKIP, the in-person events Franchise Sidekick hosts every year for around 1,000 attendees. The first one, nearly three years ago, brought out Jeremy Miner, Michelle Polar and Sonia Mitani. The most recent event, held in Arizona, gave the team a chance to interview franchisees directly on-site, including a Busy Bee Cleaning franchise owner.
One moment from that first Skip event has stuck with the hosts ever since – Michelle Polar's reframe of fear. She faces her fears, and instead of what's the worst that can happen, she asks herself, what's the best that can happen.
What's next: From stories to systems
If the first 50 episodes were about collecting stories, the next chapter is about building a system out of them. Ryan, who's currently writing a book on the subject, put it plainly …
“There's no single resource that walks someone through the entire journey from W-2 employee to business owner, no step A to step Z,” Ryan said. “That gap is exactly what we’re setting out to fill. I think there's a lot of frameworks that I've started to kind of crystallize in my mind on what people need to do to actually be successful.”
Underneath it all, the founder stories remain the fuel.
"I'm a founders guy, I love founders," Tyler said. "It's so hard to create an amazing business that helps a lot of people. And when you hear it, the impact, it's incredible."
Ready for more episodes?
“The Sidekick Life” is packed with conversations, real talk, expert guests and practical insights for entrepreneurs at every stage of the journey.
Subscribe to our YouTube channel and stream new episodes every other week on Apple Podcasts and Spotify and never miss the conversation that might just change everything.
