When I sit down with guests for the Exceptional Companies Podcast, my goal is always to cut through the noise and get to the truth about what it takes to buy, grow, and sell small businesses. In this episode, I had the privilege of talking with William “Will” Fry, co-founder of Main Shares.
One line stuck with me so much that I repeated it again at the end of our conversation: find yourself first, and then if business acquisition is the number one thing that will get you there, go do it. That idea shaped our entire discussion.
Why Will Started Main Shares
Will’s story starts in Greenville, North Carolina, where the economy is powered by hospitals, the local university, and small businesses. After years in New York, he moved home and shadowed family friends—a tobacco farm, an auto shop, and others. He quickly saw the succession problem that so many towns face. Kids don’t want to take over. They move to bigger cities. Owners are left without a plan.
He launched a brokerage called Beacon, and then later Main Shares when he realized the real issue: the best potential operators often lack capital, while the people with money sometimes want passive investments—or worse, they walk in and alienate the workforce in a matter of weeks.
Main Shares is his answer: a company designed to unlock capital, support operators, and keep Main Street businesses thriving.
Training, Capital, and Support
Will broke down what they do into three pillars:
- Training. Their free community, the Main Shares Network, offers real coursework, tests, weekly events, and guidance from current owners. It’s not about selling a $999 ebook—it’s about preparing buyers so deals are actually fundable.
- Capital. This year alone, they’ve been involved in about $140 million worth of acquisitions, with $60 million of equity invested. Typical checks are $250,000 to $1 million, drawn mostly from a network of 2,500 accredited investors and family offices.
- Support. After close, their team helps with transitions, quarterly reviews, and problem-solving. As Will put it, they’re not the experts in everything, but they usually know who to call.
What Makes a Buyer Fundable
We talked about what separates a solid buyer from one who’s not ready. Will groups it into three buckets:
- Operator-business fit. You don’t need decades of experience, but you need to show risk tolerance and humility. The best buyers even convince a seasoned industry owner to invest or advise alongside them.
- Deal structure. Many buyers set themselves up for failure by overpaying or leaving no breathing room. Most acquisitions go through a J-curve—profits dip before they climb. Without margin for error, even a great business can sink.
- A pragmatic plan. The right buyers can show what their first hire will cost, how long it’ll take to break even, and how the numbers really work. The wrong buyers talk about rolling up ten businesses in year one.
I added my perspective here too: in small business, value creation lives in the doing. Sales and operations are the levers. If you can’t run one of those well, you’re in trouble.
Reality Checks Buyers Need
Will stressed that you have to ask two questions in order: should you own a business, and should you buy one?
Searching can take 12 to 24 months and almost always comes with a personal guarantee. That’s not something to stumble into lightly.
Some of the red flags he sees:
- Assuming sky-high growth will last forever.
- Overlooking working capital and equipment costs.
- Jumping from zero management experience to leading 100 employees.
On my end, I told Will we’re actually trying to “discourage” buyers—not to stop them, but to qualify them. A deal can be a great business and still be a terrible fit for the wrong buyer. We’ve seen too many people dig themselves into five-year holes by ignoring that truth.
Stories of How It Works
Will shared two case studies that really highlight what good deals look like.
One is Joe Solberg, who bought Point B, a branding agency in Chicago doing four to five million in revenue. Joe had 15–20 years in marketing and had already acquired a smaller design firm. The leap made sense, and Main Shares funded the equity with a group of investors. Joe still sends them monthly updates, and the team helps him think through growth and working capital as the business expands.
The second story is about a Marine Corps veteran who bought a security business in Sacramento. His investors were fellow veterans. They rounded out his skills on finance and opened new business doors. That’s capital plus community in action.
Will also mentioned an Albany landscaping deal where one investor—who owned commercial properties—shifted his maintenance contracts to the newly acquired business. Sometimes the check that brings customers is the most valuable of all.
The Damage of Social Media Hype
We both see the same problem: social media has made small business acquisition look like the next get-rich-quick scheme. The reality? Many people who bought into those courses went bankrupt. And they made life harder for serious buyers, because now brokers and sellers are skeptical.
That’s why I wrote my book Buying Main Street. I wanted buyers to remember there’s another human on the other side. Owners have spent decades building something. Wasting their time because you haven’t figured yourself out yet is unfair.
At my firm, we also use what we call the Clarity Tool. It helps buyers and sellers define their “exceptional life” across four freedoms:
- Freedom of time
- Freedom of purpose
- Freedom of relationships
- Freedom of capital
If buying a business truly serves those freedoms, great. If it doesn’t, don’t do it.
Tools and Books That Stick
Will recommended Readwise, an app that resurfaces your highlights from books, articles, and podcasts so you don’t forget them.
His bookshelf includes:
- The Score Takes Care of Itself by Bill Walsh
- History and biography, from Napoleon to major world conflicts
- And for acquisitions, Buy Then Build, still a useful primer
I shared that Good Profit by the Koch brothers changed the way I think about growth. Sustained 12% a year might not sound flashy, but over time it’s incredible.
Optimism, Help, and Finding Your Why
We closed on a positive note, and that matters.
Will’s final advice:
- Don’t do it alone. When they invited past sellers to advise new buyers, every one of them said yes. People want to help.
- Find your why. Without a rooted reason, ownership will burn you out.
I echoed that. I don’t buy the pessimism you hear about the economy or small business. The opportunities are still there—and better than ever for people willing to do the work.
If business ownership is the path that serves your life, and you’re ready to roll up your sleeves, it remains one of the most rewarding investments you can make.
AND MORE TOPICS COVERED IN THE FULL INTERVIEW!!! You can check that out and subscribe to YouTube.
If you want to know more about William Fry, you may reach out to him at:
- LinkedIn: https://www.linkedin.com/in/fryw/
- Twitter/X: https://x.com/buysellsmb
- Website: https://mainshares.com/
Connect with Chris Seegers:
- Website: https://exceptionalcos.com/
- Email: Ch***@************OS.com
Other Resources:
- Books: Selling Main Street by Chris Seegers
