21 Hats Podcast

Ryan Markewich knows the landscaping business from the inside. He built and sold a successful landscaping company in British Columbia, then spent years coaching owners of all kinds of businesses through the Great Game of Business—helping them understand their numbers, their people, and their decisions. Now he’s a certified advisor with an AI-powered platform called LeanScaper It’s only been around for about a year, and it’s designed specifically for landscaping businesses but it’s growing quickly because it offers a practical, step-by-step playbook that helps owners think through pricing, staffing, cash flow, and growth decisions, using AI to guide—not replace—their judgment. This week on Dashboard, Ryan walks us through what happens when one industry gets an AI playbook for running a business—and why landscaping may be an early glimpse of what’s coming for a lot of small business owners.

Things are suddenly moving fast at Sarah Segal’s San Francisco PR firm. Several new clients look likely to sign on, and for the first time in a while, growth feels real. Which leaves Sarah with a familiar, nerve-racking question: Do you hire before the work arrives—or wait until the revenue is actually in the door? If she hires now, she may have to cut her own pay until the new business materializes. And there’s no guarantee it will. She still remembers the last downturn, when she had to lay off people she cared about—and she’s determined not to repeat that experience. But if she waits and the clients do sign, she risks something else: overloading her existing team, burning people out, and falling behind before she can recruit and train new hires. The pressure is even higher because Sarah has already set an aggressive revenue goal for 2026.

Plus: Jaci Russo explains why she’s adopted a different approach to planning and budgeting. Instead of guessing how much she can afford to spend, Jaci is changing the order of the math. After revisiting Mike Michalowicz’s Profit First—prompted by a story highlighted in the 21 Hats Morning Report—she’s begun setting profit targets first and forcing every other decision, including hiring, to fit around them. It’s only been a few weeks, but Jaci says the shift is already changing how she thinks about risk, growth, and what she can actually afford.

Over the past six years, Teamshares has quietly been running an ambitious experiment in small-business ownership. The company has bought some 90 businesses—promising never to sell them—and then converted those companies to employee ownership. Even amid the uncertainty of 2025, those businesses generated more than $400 million in revenue and about $60 million in profit, with a surprisingly low failure rate and unusually high employee retention. This week, Michael Brown, co-founder and CEO of Teamshares, returns to the podcast at a pivotal moment. Teamshares is preparing to go public—a move that raises obvious questions for a company built around long-term ownership and patient capital. We talk about what Teamshares has learned about buying businesses from aging owners, what employee ownership really changes inside a company, and what is likely to happen when an experiment like this collides with the public markets.

Six years ago, Kate Morgan walked away from the sale of her business just days before closing. Since then, she’s endured some rough stretches, fighting through the pandemic and a slump in the software sector where many of her clients live. She’s managed to stay profitable, and she sees lots of opportunity ahead, but the grind has worn her down. After years of pushing, adapting, and holding on, she says she’s had enough. She believes a strategic sale makes the most sense, and she’s working her network to find the right buyer. This week, she talks through her plan with David C. Barnett and Ted Wolf, two owners who—unlike most—have actually sold businesses and lived with the consequences. They push Kate to think carefully about her options and the pitfalls that trip up so many owners.

Plus: One reason Kate is ready to sell is that she’s recently published a book, and she’d like to devote more time and energy to accepting speaking opportunities. As it happens, Ted has written two books that he’s trying to figure out how to get published. Kate and David compare notes on the very different paths they’ve taken—David self-publishing through Amazon, Kate paying a big fee to work with Forbes Books. Both are quite happy with the choices they made.

This week, Gene Marks makes the case for optimism. There are all sorts of obvious issues to be concerned about but Gene cites a series of reasons his clients are expecting good things. Chief among them are a series of tax cuts that are coming on line and that are likely to provide more stimulus than many people are expecting. He also expects inflation to moderate and interest rates to fall enough to help out the housing and construction industries. Plus: What business owners need to know about the new tax rules governing over-time and tips.

Most business owners say they do. They tell themselves they just need to get through this one crisis, this one launch, this one quarter—and then life will settle down. But what if that’s not actually the goal? This week, Mel Gravely, Lena McGuire, and Ted Wolf talk candidly about what it really takes to build a business—and about whether balance is something owners are truly striving for or simply something they feel they’re supposed to want. “I gotta tell you,” says Mel, “I just don't know if people were really honest that they'd say that they'd be one to spend their time at their kid’s parent-teacher conference.” Lena stresses that it’s not about right or wrong. It’s about owners making the choice that’s right for them. “You have to make yourself happy first,” she says. “It’s kind of—we always use that, ‘Put your oxygen mask on yourself first, and then you can help others.’” The owners agree that there’s a seasonality to entrepreneurship. There are periods when the business demands more, and owners have few real options. That pressure can intensify when a company is struggling—but, intriguingly, it can be just as intense when the business is growing fast. Of course, all businesses endure periods of crisis. But what if the crises never end?

Show Notes: Here's the Josh Patrick column we discuss. It's well worth the read.

This week, Karla Trotman, owner of Electro Soft, a contract manufacturing business outside of Philadelphia, talks about the series of contradictions and tough calls she confronted in 2025. It started with the chaos of the tariffs, which you might think would have helped a domestic manufacturer but which led to suppliers charging more and to customers pulling back and to Karla feeling beaten up by her advisory board, which wanted her to reduce expenses and headcount.But Karla chose a different path.

For years, business owners have been told to follow a familiar playbook when it comes to hiring: Take your time. Be selective. Hire slow, fire fast. But more and more owners are discovering that those rules don’t fit the reality they’re facing right now. This week, William Vanderbloemen says employers can no longer indulge the luxury of hiring slow. “The shortest sermon I’ve got,” says the former pastor, “is candidates are more fickle than ever, and owners need to realize that.” Paul Downs says he’s trying to figure out what’s gone wrong with his hiring process: Is it the way he uses Indeed? The way he approaches candidates? Or the differences between hiring white-collar and blue-collar employees? Jaci Russo believes companies should always be marketing their brand as an employer and always be on the lookout for good people—even when they’re not actively hiring. Plus, in a wide-ranging, end-of-year discussion recorded in December, the three owners talk about whether they hit their numbers in 2025, whether they use a formal budgeting process, what they expect in the year ahead, and how far out they can realistically see when they try to plan for the future.

This week, Adam Russo, co-founder and owner of The Phia Group, explains how his company helps employers reduce their healthcare expenses. The key, he says, is to educate and incentivize employees to be smarter about how they purchase health care—without compromising on the quality of the care. That, he says, is how he’s able to offer employees who’ve been with Phia for five years care that is entirely free: no deductibles, no co-pays. Many of his clients are big companies that self-fund their health insurance, but he says even businesses with as few as two employees can find tremendous savings this way.

This week, we take another look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Laura Zander on how she got the price she wanted to sell Jimmy Beans Wool, Liz Picarazzi on her confrontation with a grizzly bear, Jay Goltz on why he just might be a good candidate to turn his business into a worker cooperative, Mel Gravely on why he sold his facilities-management business as soon as it became profitable, and Jaci Russo on how she figured out how to train a series of AI agents to deliver 10 client leads first thing every morning.