What it takes to run a business

Podcast

20 years ago, Bo Burlingham gave a name to a feeling a lot of business owners had struggled to articulate. In his book Small Giants, Bo profiled companies that had chosen not to chase growth at all costs. Most were bootstrapped, owner-operated businesses that cared less about getting big than about building something enduring, meaningful, and excellent. They weren’t anti-growth. They just wanted growth to be intentional. And for many owners who read the book, the reaction was immediate: “I thought I was the only one who felt this way.” Out of that recognition grew a community—and eventually an organization—led in large part by Paul Spiegelman, whose own company embodied the Small Giants philosophy. With Bo’s encouragement, Paul launched the Small Giants organization 15 years ago to connect owners trying to build great companies without sacrificing culture, independence, or quality of life.

At our recent 21 Hats Live gathering in Cincinnati, we explored where that movement goes next in a Brainstorm session with Jean Moncrieff, who took over leadership of the Small Giants organization last year. Jean—who’s from South Africa, lives in Zurich, but is moving to the U.S.—brings both momentum and candor to the role. He recently led his first Small Giants Summit in Detroit, which attendees—including me—praised for its renewed energy and sense of purpose. He’s also the author of a terrific new book, Finding Freedom: The Business Owner’s Guide to Building a Valuable Company and a Meaningful Life. But as you’ll hear, Jean recognizes there are challenges ahead.

What exactly is Small Giants today? Who is it for? What makes it different from the many other organizations competing for the attention of business owners? Does it need a more formal set of principles—or even an operating system—to help companies put its philosophy into practice? Can it stay true to its founding mission while also attracting businesses large enough to support its events and programs? Ultimately, the conversation arrives at a tension at the heart of the enterprise: Can the Small Giants organization itself become a sustainable, profitable business without losing the values it was created to protect? In other words, can Small Giants become a true small giant?

Michelle Wyatt has replayed the events in her mind countless times, looking for warning signs she might have missed. But even now, she can’t find any. Both employees had passed background checks and drug tests. Both were considered trusted, valued members of the team. And yet, within a span of months, two violent incidents involving employees left Michelle and her company reeling. In this week’s conversation, Michelle joins Jay Goltz, who has dealt with employee violence in his own business, and special guest Sandy Kapell, who’s made a career leading human resources, to wrestle with a question that haunts a lot of business owners: How much responsibility can you reasonably bear for the actions of your employees?

The discussion goes beyond hiring practices and background checks. Michelle talks candidly about the grief her team experienced, the guilt of wondering whether she should have seen something sooner, the relief that the violence didn’t occur aboard her riverboat cruise ship, and the unsettling realization that no amount of experience truly prepares you for something like this. “Please stop torturing yourself,” Jay tells Michelle. “From what you've said, there's just nothing you could have done about this. It's part of business, unfortunately.”

When Kate Morgan started thinking seriously about selling her business, she assumed the big payoff would come at closing. But as she tells David C. Barnett and Paul Downs this week, she’s come to understand that the smarter move might be not selling—at least not yet. Why? Because if the business keeps performing and she can gradually remove herself from the day-to-day operations, she may ultimately make more money by continuing to own it. That’s partly because, as David explains, small businesses often sell for lower multiples than owners expect. Which means the real value may not be in a clean exit, but in continuing to collect profits while slowly transitioning ownership to key employees. “So you'll be selling the business,” says David, “and you'll be collecting dividends or distributions on top of that. This is one of the most lucrative exits there can be.”

Of course, delaying a sale comes with its own risks. Markets change. Businesses cool off. Buyers get nervous. “You have to make the decision and make the sale happen while you've got a full head of steam,” David warns. Wait too long, and the numbers can start sliding in ways that dramatically reduce what buyers are willing to pay.

Plus: A Reddit post raises a brutal management challenge: What’s the best way to lay off a relative? “It really can't affect your decision,” says Paul. “Because if it needs to be done, it needs to be done.” That doesn’t make it easier. It just means you may have to live with both the business consequences and the family consequences at the same time.

Every business owner looks forward to that big break—the moment that you land a big client or a major retailer, or do something that puts you on a national stage. But those opportunities don’t just reward you. They can also expose you—especially if you have to take on debt or ramp up production or do things you haven’t done before. Four years ago, when Liz Picarazzi won a high-profile installation for her trash enclosures in Times Square, it was exactly that kind of opportunity. Her enclosures were put to the test in as public and as challenging an environment as she could imagine. And, by any reasonable measure, they failed. In pursuing that opportunity, Liz took a risk that led to what she calls the worst day of her professional life. It also turned out to be, as she tells Lena McGuire, the best thing that could have happened to her business. That moment forced changes she might never have made otherwise, pushing her to innovate faster and sending her business on a very different trajectory.

Meanwhile, Lena is dealing with a quieter version of the same problem: what it really takes to move your business forward. She knows her systems need an upgrade. She’s bought the software. But like a lot of owners, she’s stuck in the messy middle—paying for the future while still trapped in the past, with no time to bridge the gap. How do you choose between tasks that generate revenue immediately and those that will improve operations over time?

For Lena McGuire, scope creep really can show up around every corner. She’s in the home remodeling business. But for most owners, including Jaci Russo and Ted Wolf, projects that expand out of control can be less visible but just as hard to contain. It’s baked into the job, because every assignment comes with a built-in tradeoff: Protect your margins or protect the relationship. And especially in the early days of a business, when reputation feels like everything, that’s not much of a choice. “I was afraid to have tough conversations with people,” Ted says. “I just wanted everybody to like us.”

Over time, systems help and boundaries get clearer. But the pressure never fully disappears. There’s always one more request, one more detail to tweak—especially when you’re thinking about the reviews and testimonials. “You want to get those nice photos at the end,” says remodeler Lena. “You want to get a referral.” This week, Lena, Jaci, and Ted talk about how their thinking on scope creep has evolved—and why it never stops being an issue.

Plus: On the small business subreddit, an owner recently posted that he finds chasing accounts receivable so distasteful—it feels like begging—that he often puts it off and hopes for the best. “Is this just me?” he wants to know. “Or is this a common thing for small business owners?” We discuss. And Jaci explains why, even if she could get it, she wouldn’t even consider accepting a $500 million account promoting a big deal consumer brand.