Owning a small business can be an isolating experience. I’ve spent years helping entrepreneurs fight that loneliness by building tight-knit peer groups that deliver a real return on investment.
Through these groups and my conversations with over 2,000 business owners, I’ve dug into what really works—and what doesn’t.
In this podcast, we’ve tackled everything from working-capital traps and hiring discipline to burnout and the surprising reasons why some owners sell just a year or two after buying a business.
Keep reading below to get an idea of what I covered in this podcast episode.
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Listen to the full conversation below, or click here to watch it on YouTube.
The Scalepath Solution
I founded Scalepath to create a community for small business owners, providing a structured environment to share experiences and learn from one another.
The goal is to move beyond mere therapy and create a space where entrepreneurs can find actionable advice to grow their businesses. Each peer group consists of about eight business owners in similar niches and revenue sizes.
They meet for two-hour virtual discussions once a month to talk through mistakes, explore opportunities, and share lessons learned from their experiences.
Real-World Lessons
My conviction in this model was solidified after seeing an acquisition entrepreneur nearly lose everything.
After purchasing a large commercial HVAC installation company in late 2021, the new owner faced a perfect storm of rising interest rates, clients delaying payments, and an estimator who was significantly underbidding projects.
This experience highlighted the intense pressures and unforeseen challenges that can overwhelm even seasoned operators. It was this realization of the need for a support system that led to the creation of the first peer groups.
Building Community
Initially, these peer groups served as a form of business therapy—a place for owners to vent and connect with others facing similar struggles. Over time, the focus shifted from just sharing frustrations to driving a clear return on investment for its members. A great event, as I discovered, is small, intimate, and brings together people with similar business models and challenges. I found that a three-hour format allows for deep, meaningful conversations where everyone has a chance to contribute.
While building a national network, I also learned that organizing local, in-person events is surprisingly difficult. Entrepreneurs are busy, and getting them to commit to regular meetups requires a dedicated effort that few have the time to sustain. This reinforced the value of a structured, facilitated community like Scalepath.
The Van Life
To bring these communities together, I made a bold move: I bought a $42,000 camper van to travel the country full-time, hosting small business meetups wherever I went.
This “van life” approach became more than just a logistical solution; it turned into a standout B2B marketing tool.
Showing up in a camper van is memorable and breaks the ice, making it easier to build genuine connections.
It’s a testament to the idea that sometimes, the most effective marketing is about creating unique, personal experiences.
Key Entrepreneurial Insights
Through countless conversations, a common theme has emerged: the dream of buying a small business and running it for 30 years is becoming less desirable for many. After two to three years, many owners confront the harsh realities of growth constraints and personal fatigue from constantly fighting fires. They realize their initial vision may not align with the day-to-day grind.
Another critical lesson is the danger of undercapitalization. One of the most consistent pieces of advice shared within the groups is to take every dollar a bank is willing to offer during an acquisition. New owners often underestimate their working capital needs, and since banks are hesitant to lend more until a business has a two-year history under new ownership, that initial capital is crucial.
Conclusion
The journey of a small business owner is often isolating, but it doesn’t have to be. The real work begins after the deal closes, and having a support system in place before a crisis hits is invaluable. Peer groups provide a space for entrepreneurs to connect, share unfiltered stories, and gain actionable insights that aren’t typically found on social media.
Scalepath is built on the idea that community is one of the most valuable assets an entrepreneur can have. By learning from the wins, misses, and messy middle of others, business owners can navigate their paths with more confidence and clarity.