21 Hats Podcast

Hannah Sandmeyer spent years acquiring ecommerce businesses for an Amazon aggregator, giving her a front-row seat to how deals get done—and what often gets lost in the process. Too many owners, she came to believe, are forced to choose between shutting down their businesses or selling to buyers whose priorities may have little to do with preserving the company, the culture, or the people who built it. So she decided to build an alternative. Hannah is now founder and CEO of Steward Market, which she describes as “the first marketplace for ethical exits.”In this week’s Dashboard, she explains what makes an exit “ethical,” why some owners are actively looking for alternatives to private equity, and how Steward Market hopes to connect values-driven sellers with buyers who want to continue what those owners have built—not simply maximize short-term returns. She also explains why the company chose a business model that doesn’t rely on taking commissions from deals.

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.

Most business owners know they need marketing. What many don’t know is what they should be paying for it—or what they should expect in return. So when an SEO agency proposes a $3,500-a-month plan, how do you assess whether it’s a smart investment or an expensive gamble? Do you know how many new customers it would take to make that spend worthwhile? Do you even have the data to answer that question? This week, Shawn Busse says too many owners are making those decisions in the dark. He offers a practical framework to help you do the math to evaluate marketing proposals, set realistic expectations, and decide what’s worth spending—and what isn’t.

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 years, the Wine School of Philadelphia and PhillyWine LLC coexisted in the genteel world of wine education. Then a trademark dispute turned that quiet coexistence into a legal battle—complete with accusations, lawsuits, and mounting costs.This week, Keith Wallace, founder of the Wine School of Philadelphia, joins me to talk about what happens when a business owner who’s tried to avoid litigation at all costs suddenly finds himself in the thick of it. He shares what the fight has actually required—financially, emotionally, and strategically—and what he wishes he had done differently before things escalated. Because one of the hardest lessons for any owner is this: you don’t have to want a legal fight to end up in one.

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.