21 Hats Podcast

In her thirties, Lisa Woodruff hit a breaking point—overwhelmed, overweight, and depressed, as she puts it. So she made a radical decision: she quit her job as a school teacher and set out to get her own life in order. What started as a personal reset became a business—Organize 365—built around a simple but powerful idea: running a household isn’t all that different from running a company.In her new book, Escaping Quicksand, Lisa argues that households, like businesses, need systems, delegation, and intentional leadership. But she also makes a point that may resonate with a lot of listeners: for women especially, the stakes—and the expectations—are different. This week, Lisa explains what she’s learned about escaping overwhelm and why treating your home like a business might be the key to getting your life back.

Pricing a service business sounds straightforward—until you actually have to do it. How much should you charge? What’s reasonable? And what happens when “reasonable” isn’t enough to keep the business healthy? This week, Sarah Segal walks David C. Barnett and Liz Picarazzi through how she thinks about pricing her PR services—why she aims for consistency across clients and why she resists charging based on what the market will bear but insists on building in enough margin to stay profitable. It’s a balancing act between values and reality, and not always a comfortable one.

The conversation gets into practical questions every business eventually faces: Do you raise prices a little every year, or wait until you’re forced to raise them more than just a little? Do you price based on your costs—or your customer’s perceived value? And how do you handle those conversations without damaging relationships you genuinely care about?

Plus: Liz expects a tariff refund—but isn’t counting on it to help very much. She also explains why she’s stopped flying employees around the country for installations.

Shawn Busse has never been an AI evangelist. If anything, he’s been wary of the hype. But lately, his thinking has started to shift. While it’s still early, Shawn sees AI pushing marketing away from the soul-deadening world of SEO hacks and keyword stuffing—and toward something far more human: real storytelling and authentic brand building. In this week’s Dashboard, he explains what he’s seeing in his own business and with clients, and what it may mean for owners trying to figure out where to focus next.

It’s easy to condemn the horror stories coming out of Noma, the celebrated restaurant in Copenhagen. But this week, Jay Goltz, Jennifer Kerhin, and Ted Wolf confront a harder question: How far are the rest of us—business owners in every industry—from crossing the line? Because it’s not just restaurants. Most owners don’t set out to be abusive. They set out to build something great. And somewhere along the way, high standards can start to blur into something else. ‘I was out of control when I was in my 20s,’ Jay admits.

So, what changed? And where did the owners land? How much command and control is actually necessary? When does pushing someone cross the line—and when does not pushing them enough become its own failure? Have you ever held onto the wrong employee too long? Or pushed the right one too hard? Jay doesn’t sugarcoat his opinion about yellers: “You’re going to tell me you’re passionate. I’m going to tell you, ‘You’re an asshole.’”

The group digs into the trade-offs every owner faces: hiring versus managing, systems versus stars, culture versus performance. What do you do with the high performer who damages the team? Can you really coach anyone to excellence—or are there limits? And then there’s the quiet warning sign many owners ignore: Something goes wrong, and someone says, “Oh, well, everybody knows how Bob is.” That, says Jay, is when you know you’ve got a problem. This is a conversation about judgment calls—messy, human, unavoidable. Because as Jennifer puts it, “It’s really hard to manage people.”

Chris Campbell started his first business at 18 and has since built and sold companies in landscaping, construction, furniture, and marketing. After his most recent exit, he spent years searching for a business to buy—and found nothing. That dead end turned out to be an opening.Instead, Chris and a group of partners—including his wife, Emily—decided to start something from scratch. The result: a plan for Banana Daddy, a high-concept soft-serve shop built around banana ice cream that would take $2 million to open. Every experienced restaurant operator they consulted had the same reaction: Don’t do it. They did it anyway.It's less than a month in, but so far, Banana Daddy is exceeding expectations. Fueled in part by playful, slightly suggestive, but still kid-friendly marketing—”Please Lick Responsibly!”—it draws lines around the block and has even required a bouncer to manage the crowds. Along the way, the team has discovered something they didn’t expect: a surprising number of people want ice cream first thing in the morning. “It’s bananas,” says Chris. And this is only the first step in a much bigger plan.

Given everything going on in the world, you might expect a rough start to the year. But for Paul Downs, Jennifer Kerhin, and Jaci Russo, 2026 has actually begun quite well. In fact, Jennifer and Jaci say they’re finally climbing out of what many owners call the Valley of Death—that long stretch when the business depends on you for everything and when it starts to outgrow your people and your systems. Exiting the valley can take a lot longer than people expect. Jennifer is seeing daylight in year 17. Paul says it took him 25 years, a quarter of a century. “Most of that time,” he admits, “I was just wallowing in ignorance.” One lesson they’ve learned the hard way: growing too fast can do real damage. “You burn out your employees,” Jennifer says. “You provide poor quality control to your clients. You make everybody upset and angry.”

Along the way, the three owners cover a lot of ground: what actually makes trade shows worth the investment (hint: it’s what you do before and after), why you may not be able to copyright that graphic design, why your logo needs a trademark, why Paul’s Google traffic is holding up but his Middle East expansion is on hold, what Jaci has uncovered about the shocking cost gap in health insurance for her female employees, and why it’s insane that business owners have to manage their employees’ health insurance in the first place. It’s a wide-ranging conversation—but underneath it all is a theme most owners will recognize: Progress doesn’t always come from big breakthroughs. Sometimes it comes from surviving long enough to figure things out.

For most business owners, rewarding employees for doing their jobs well is just common sense. Hit your numbers, get a bonus. Sell more, earn more. Perform better, get paid more. That’s how motivation works…right?This week, management consultant Kelly Allan asks owners to reconsider that assumption. Allan is steeped in the teachings of W. Edwards Deming, the management thinker widely credited with inspiring Japan’s post–World War II industrial revival. Deming argued that pay-for-performance systems don’t actually improve performance. Instead, they create unintended consequences—encouraging people to chase metrics, compete with colleagues, and optimize the wrong things.In Deming’s view—and in Allan’s—performance isn’t primarily about individuals at all. It’s about the system they work in. In our conversation, Kelly explains why incentives often backfire and how owners who are curious can begin experimenting with a different approach.

It’s already been quite a decade for owners: a pandemic, inflation, tariffs, and now, suddenly, war with Iran—bringing with it the biggest spike in oil prices ever. And looming over everything is the still-uncertain impact of artificial intelligence. This week, David C. Barnett, Jay Goltz, and Ted Wolf talk about how all that uncertainty is shaping the decisions owners are making right now—from whether it’s wise to invest in new equipment to how some lenders are demanding that would-be borrowers articulate their AI strategy before obtaining a loan.

The implications of all of this vary by industry, but Dave says some sectors suddenly look a lot riskier than they did a year ago. “I don't know if I'd want to get a 90-percent loan to buy a marketing agency today,” he says. At the same time, the economics of AI could push owners to move faster than they might otherwise. As Dave notes, if a $10,000 or $20,000 investment in AI can quickly replace two positions, that’s the kind of return many owners will find hard to ignore when expenses are rising.

Along the way, the three discuss why periods like this can also create unexpected opportunities. Keep your eyes open, Dave advises. “A lot of those opportunities may come from a competitor stumbling.”Plus: what happens when business owners suddenly realize they should have been collecting sales tax all along. Do you pay the back taxes yourself? Start collecting now and hope for the best? Or is there a smarter way to fix the problem?

It does in this sense, says Victor Hwang, founder of Right to Start, an advocacy group that works to expand entrepreneurial opportunity: While starting a business can be daunting, many Americans assume it’s even more daunting than it actually is. For six years, Victor and his organization have tried to address that concern by removing barriers to entry and spreading awareness of entrepreneurial opportunities. In this episode, Victor discusses the progress Right to Start has made, including significant recent steps in Oklahoma. He also has big plans for the 250th celebration of what he likes to call America’s startup.

Despite the waves of uncertainty crashing across the economy, this week we hear from three owners who feel cautiously good about how their year has started. David C. Barnett budgeted for slightly less revenue in 2026, but he’s operating more efficiently and expects to turn a bigger profit. Jaci Russo is hitting her revenue projections—and after implementing a profit-first accounting system, she says the results have been “eye-opening.” And while Lena McGuire isn’t quite on track to meet her aggressive goal of doubling her business this year, she’s doing far better than she did a year ago.

Along the way, we talk about getting runaway software subscriptions under control, figuring out how businesses get discovered in an AI world, and why Jaci’s health plan charges almost three times as much to cover female employees as it does comparable male employees. And we consider a question that might have sounded ridiculous not long ago: Has it become harder to get a job than it is to start a business?