Josh left corporate America and nearly spent $1.5 million on the wrong franchise. Hear how he found the right fit and changed his life for the better.
Some people stumble into entrepreneurship. Others spend years waiting for the right moment. And then there are people like Josh Herscheid – a former Microsoft employee turned franchise owner – who had the entrepreneurial itch his whole life but needed the right bridge to finally cross over.
On this episode of "The Sidekick Life", Ryan and Tyler sit down with Josh to unpack a journey that includes a near-miss with a $1.5 million coffee franchise, a smart pivot and ultimately landing on a low-cost youth enrichment franchise that fits his life perfectly.
Key takeaways
- Brand love can be a trap. Falling for a concept before doing the real work is one of the most common (and costly) mistakes first-time buyers make. Do your homework before you fall in love.
- A proven process beats going it alone. Josh spent over a year spinning his wheels with the coffee franchise. Working with a Franchise Sidekick Advisor gave him clarity in a fraction of the time.
- Low cost doesn't mean low opportunity. Soccer Stars cost less than 5% of what the coffee franchise would have and created a path to recurring revenue, flexibility and real fulfillment.
- Have a financial plan before you quit your job. Patience and preparation are what give you the runway to build something right. Having a spouse with a W-2 and cash in the bank made all the difference for Josh.
- The mental game is real. Replacing a corporate salary takes time. Going in with the right expectations and the right support is what keeps most people in the game long enough to win.
- You don't know what you want until you're in it. Franchising gave Josh a real-world MBA. Every win, every stumble and every curveball taught him something he couldn't have learned any other way.
Always an entrepreneur, finally a business owner
Josh grew up wired differently. The sweet corn stand in Nebraska. The eBay hustle in college. A running list of 100 business ideas on his phone. Even while climbing the ranks at Microsoft and becoming a partner at a consulting firm, the pull never went away.
"I always knew I wanted to be an entrepreneur," Josh said. "But I never had anything compelling enough to make me say, I'm going to do this."
That's when he turned to franchising. Not because he lacked ideas, but because franchising offered something his ideas couldn't: a proven system with real validation behind it.
The $1.5 million wake-up call
Josh did what a lot of first-time buyers do: he fell in love with a brand. A fast-growing, drive-through coffee chain was expanding into Minnesota, and he signed a franchise agreement before truly understanding what he was walking into.
What followed was over a year of fruitless commercial real estate searching and a slow realization that the all-in investment would top $1.5 million.
"After I signed the dotted line," Josh said. "It really hit me that there was going to be a lot more money and a lot more risk than I was anticipating."
A trusted connection referred him to Sidekick, and that referral changed everything.
The process that changed the game
When Josh connected with Sidekick Advisor Desiré Stephens, he quickly understood the difference between doing your own research and working with someone who has a real system behind them.
Des dug into what Josh actually wanted, the type of operator he wanted to be, his lifestyle needs, his family situation and his financial picture. She brought his wife into the process. She introduced brands he'd never considered.
"Her being a franchise owner herself was really comforting early on," Josh said. "She's like, ‘Hey, I went through this.’ That was super helpful. Just that credibility she brought to the table."
Within a couple of sessions, Josh had more clarity than he'd found in a year and a half on his own.
Why he chose Soccer Stars
When Soccer Stars appeared in his second round of brand options, something clicked immediately. Josh and his wife looked at each other and knew.
The brand checked every box: low investment (around $60,000–$70,000 all-in versus $1.5M for the coffee concept), no brick and mortar, recurring revenue through school and daycare partnerships and a schedule that worked with two kids under three. He was in front of paying clients within months of signing, not years.
"The recurring revenue aspect was really attractive," Josh said. "Once you get in the door, you can run classes all year round. And the feedback we hear from parents, ‘Timmy's coming out of his shell, he looks forward to soccer Wednesday,’ that type of feedback is super, super cool to me."
The financial strategy (and the mental game)
Josh and his wife had a deliberate plan. Save first, keep her W-2 for stability and benefits and pursue franchising as a path to long-term freedom. The tax advantages of business ownership also made a real difference, especially in a year when Josh cashed out equity from his previous firm.
"We went through the full tax cycle and got money back for the first time in eight years," Josh said.
But the mental side? That took work, too. Leaving a high corporate salary means letting go of the number you used to tie your worth to, and that's a real adjustment.
"Nothing happens unless you drive it," Josh said. "I know when I'm taking my foot off the pedal or when I'm putting it down. There's a direct correlation to what's going on in the business."
The payoff? His wife noticed within six months. He's happier, less stressed and more present with his kids.
"So much happier," Josh said. "I feel like I'm making a much bigger impact. All those things, you can't put a price on."
Ready to explore franchising?
Josh's story is a reminder that the path to business ownership doesn't have to be a massive financial gamble. With the right guide, the right process and the right fit, you can build something that works for your life, not against it.
