Owning a small business can be a solitary grind. Rand Larsen’s SMB Community peer groups give entrepreneurs a place to vent, swap advice, and learn how to survive the chaos.
Rand Larsen’s small business is small business. More specifically, his business is providing something like group therapy for other small business owners–over Zoom, and with a yearly $3,000 membership fee instead of an hourly rate.
To join, a business must have at least $1 million in revenue. Most members are men in their 30s and 40s, ambitious and family-oriented, trying to build something bigger. The group helps them do that, but just as important, it reminds them that they aren’t the first to navigate the choppy waters of entrepreneurship.
During a March peer group meeting, eight business owners log in from Chicago, Austin, South Carolina and wherever else they happen to be. Their backdrops (real, not fake) range from polished, well-appointed offices to cars, kitchens, and what looks like either a bus or a train. With Larsen and a business coach moderating, the call starts with a simple question: Rate how you’re doing on a scale of one to ten. Most land in the top half of the scale. One member casually mentions having to fire an employee. A beat of silence, then a murmur of sympathy. Everyone here knows what that’s like. Another shares that he recently spent a few days in the hospital. The group shows genuine concern, but there’s also some light laughter when he jokes that at least being bedridden gave him time to catch up on paperwork.
The conversation turns to keeping sales teams motivated. One owner shares his strategy: His team plays a poker-style game where each sale earns the seller a card. The idea is to gamify the process, making small wins feel rewarding beyond the paycheck.
These small moments highlight a bigger issue. Running a business can feel like you’re on your own, with frustrations and challenges you don’t necessarily want to share with your colleagues (or competitors) at the local Chamber of Commerce or business league.
Connections are hard to come by for small business owners. In a 2024 survey by Truist Bank, just 17% of small business owners reported seeking out peer advice. While 35% have a formal growth plan, less than a third of those with plans have shared them with a formal advisor like a CPA, lawyer or banker. Bottom line: Most small business entrepreneurs carry on without either peer or professional advice.
For over a year, Larsen, the 29-year-old founder of SMB Community, has been crisscrossing the country in a 2019 Dodge Ram ProMaster camper van. He’s logged more than 10,000 miles hosting small business meetups in person and pitching his Zoom groups. Along the way, he has become a human Rolodex, the guy to know when you need to find a guy. Larsen estimates that he’s met as many as 500 small business owners at his various events, for which he says he never charges an entrance fee. He’s got sponsors who help cover the tab and, sometimes, pay him a bit for organizing them.
One of the first to join was Matthew Saskin, 41, who owns East Coast Towing in Raleigh, North Carolina, a business he expects to generate $9 million in revenue this year. He bought it for $4.1 million in 2022 with the help of an SBA loan. “Most of us have SBA debt, we have leverage on our businesses, and that comes with unique challenges that other small business owners can’t relate to,” Saskin says of his Zoom peer group.
Saskin also attends local Chamber of Commerce events. The problem, he says, is that there aren’t many entrepreneurs like him in the room. “There are few to no members at the Chamber who fit our profile,” Saskin says. Entrepreneurship through acquisition has gained traction, but remains rare in the broader small business world. While hard data is scarce, BizBuySell, an online marketplace for small businesses, offers some perspective. In 2024, the platform reported 9,500 closed transactions. For context, the U.S. Chamber of Commerce counts more than 33 million small businesses nationwide.
When the Google Business profile for 33-year-old Jack Carr’s Brentwood, Tennessee-based Rapid Response Plumbing, Heating & Cooling disappeared from the web, he turned to his SMB Community peer group. He found someone who had dealt with the same issue. “They recommended a person I could talk to to get my main marketing channel back up and running fast,” he says.
Carr’s HVAC business generates about $5 million in annual revenue. That’s roughly $14,000 a day. If the tip from his peer group helped resolve the issue even a few hours faster than it would have otherwise, the cost of a year’s membership paid for itself.
Of the hundreds of small business owners who have attended Larsen’s seminars, 35 have signed up so far for networking membership. Each is placed in a peer group that meets once a month on Zoom for calls facilitated by Larsen and/or a business coach who works with him. They swap strategies, trade war stories, getting moral support and a reminder that they’re not the only ones carrying the weight of payroll, growth, and survival.
“Running a small business can be an incredibly isolating experience,” Larsen says. His skill, whether it comes naturally or was honed during his Tau Kappa Epsilon fraternity days, is bringing people together.
So just how does an under 30 bro become an apostle of small business networking?
Larsen grew up in Tacoma, Washington, and studied entrepreneurship at Boise State. He liked the idea of building something from scratch, seeing it as a safer bet than the stock market. “If you invest in yourself, you’re relatively predictable,” he says.
His first job was at R.S. Hughes, a distributor of industrial supplies. “Very boring, but essential things,” he says. On the side, he worked at a cannabis pharmaceutical startup selling treatments to nursing homes. But what stuck with him wasn’t the cannabis, it was the nursing homes.
In 2019, he launched his first business, filming documentary-style videos of elderly residents for their families. Convincing subjects to participate was a challenge. “The revelation,” he says, “was that you can have a fancy startup idea that tries to change consumer habits, or you can go with the flow and do something more practical.” He pivoted to selling testimonials to retirement communities instead.
The business was on track for $100,000 in revenue before COVID shut it down. Nursing homes went into lockdown, contracts disappeared, and with no clear end in sight, Larsen walked away. But the experience, especially the film and production skills, set him up for what came next.
Scrolling Twitter (now X), he found a job posting from John Wilson, one of the many proselytizers of entrepreneurship through acquisition–that is, the belief that buying a business is smarter than starting one from scratch. Wilson needed someone to handle grunt work while learning the business-buying process. Larsen’s mix of entrepreneurial experience and technical skills made him a fit, and his videography background was a bonus. Wilson could use the help on his podcast.
Larsen packed his bags for Akron, Ohio, which he still calls home when he’s not on the road. The plan was simple: train under Wilson, then buy a business of his own. After 15 months, he started looking. But without enough capital to pull it off, he needed a new plan.
Then, in April 2022, he met a business owner in crisis. The man had bought an $18 million (revenues) commercial HVAC company. Then, interest rates spiked, builders stopped giving him work, and an estimator was botching bids and overtime. He lost $1.8 million in his first year. Some of it was the natural J-curve struggle of a new owner. Some of it was just bad luck. Either way, he felt like he was drowning.
When Larsen met him, the guy was at rock bottom, wondering if he had just bankrupted his family. Larsen hadn’t gone to visit expecting to play business therapist, but as the conversation unfolded, it became clear what was really wearing the owner down. “You can’t talk about this stuff with employees,” Larsen says. “Not even managers. You don’t want to overburden your spouse. And your friends just don’t get it.” The man felt completely alone.
Larsen had an idea: talk to other business owners dealing with the same struggles. He went on Twitter, found a few more operators willing to share their experiences, and looped them all into a call. That first peer group started meeting every few weeks. It was part business, part group counseling. They even gave it a nickname: trench therapy.
That’s when Larsen realized this could be more than just a favor to a friend. It could be a business.
Business clubs and networking groups have been around forever. At the highest levels of business, executives have private, expensive peer groups where they can speak freely. Local Chambers of Commerce, trade associations, and industry meetups all exist to connect entrepreneurs. But those spaces aren’t built for honesty. No one wants to lay out their struggles in a room where competitors are listening, ready to pounce on any sign of weakness. Real talk about business problems requires trust, along with some guardrails, like geographic diversity, to ensure you’re not handing your competition a blueprint to your soft spots.
It’s the same reason you won’t hear business owners openly discussing exit strategies in those settings. On the Zoom call in March, the conversation turned to selling a business. What kind of EBITDA multiple you can command, whether bringing in a full-time general manager means giving up equity, and how that decision affects your valuation. These are big questions, the kind you don’t want to workshop in front of people who might one day be bidding against you–or be bidding to buy your business.
Even when the setting is safe for open discussion, the mix of business owners has to be right–which is part of the pitch for the SMB Community. Larsen is hand-crafting peer groups by business model and revenue size to keep discussions relevant, while separating participants by geography, to keep discussions safe. Companies doing between $1 million and $7 million are grouped together, while those over $10 million have their own cohort. The goal is to match members with peers facing similar challenges, whether it’s tackling cash flow issues or just venting.
“You build a callus,” Larsen says. “At first, people come in feeling beaten up, like they’re the only ones struggling. Then, after a few meetings, they realize ‘oh, it’s not just me.’”
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