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PODCAST

21 Hats Podcast

The 21 Hats Podcast presents an authentic weekly conversation with small business owners who are remarkably willing to share what’s working for them and what isn’t. Unlike many business podcasts, which tend to talk to highly successful entrepreneurs whose struggles are in the past, the 21 Hats Podcast features a rotating cast of business owners who are still very much in the trenches fighting the good fight. Every week, our regulars gather to talk about the kinds of important issues many owners

business entrepreneurship

All Episodes

51:58

We Had to Become an AI-First Company

21 Hats Podcast ·

2026/10/06

This week, we welcome a new regular to the podcast team, Rob Levin, co-founder of WorkBetterNow. I first met Rob more than 20 years ago, when we were both experiencing the decline of print media. I was an editor at Inc. magazine, and Rob had started a regional publication for business owners called The New York Enterprise Report. “Starting a print publication in 2003 was not one of the smartest things I've done,” Rob says. But he learned from that experience. In 2018, Rob and a partner started

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39:20

Dashboard: Finance Your Business Without Taking on...

21 Hats Podcast ·

2026/10/02

Most business owners know the usual ways to finance a startup or acquisition: savings, investors, bank loans, SBA loans. But there’s another option that many owners have never considered—even though Jeremy Ames says his company, Guidant Financial, has helped arrange more than 35,000 of these transactions. It’s called ROBS financing—Rollovers for Business Startups—and it allows entrepreneurs to use money they’ve accumulated in retirement accounts to start or buy a business without taking a taxable

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48:05

Maybe AI Won’t Destroy My Business

21 Hats Podcast ·

2026/09/29

This week, Paul Downs, Jaci Russo, and Sarah Segal revisit a question that came up on the podcast more than a year ago: Is artificial intelligence going to doom professional service firms like Jaci’s branding agency and Sarah’s PR firm? So far, both Jaci and Sarah are feeling pretty good about their prospects. In fact, they’re seeing changes in the market that suggest AI may be helping rather than undermining their businesses. Paul, meanwhile, has encountered a different kind of AI mystery. For

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30:32

Dashboard: Do You Care What Happens to Your Business...

21 Hats Podcast ·

2026/09/25

This week, Lou Mosca raises a question that business owners may not spend enough time thinking about before they sell the business: Once you’ve gotten the price you want, how much do you care what happens to the business? Lou, who owns the consulting firm American Management Services, has spent decades working with owner-operated businesses. More recently, he’s also been trying to work with private equity firms whose portfolio companies need help improving their performance. And that has given him

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46:28

Can an Owner Really Know What’s Going On?

21 Hats Podcast ·

2026/09/22

This week, Jay Goltz and William Vanderbloemen tackle a problem that business owners may associate with big companies: What happens when an employee becomes convinced that his or her manager is making bad decisions, but going through normal channels just isn’t working? Jay says he absolutely wants employees to speak up, even if that means going over a manager’s head. William agrees that there are times when an employee has to escalate a problem. But as the conversation unfolds, both acknowledge

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33:50

Dashboard: Are You Still the Best Person to Run Your...

21 Hats Podcast ·

2026/09/18

For a lot of business owners, there comes a point when the obvious choices seem to be: keep running the business or sell it. But Tighe Burke says there’s a third option that owners often overlook: keep the business, hire someone else to run it, and let that person take it places you may not be equipped—or inclined—to take it yourself. Burke, who runs the executive recruiting firm Srch, specializes in finding operators for founder-led businesses. He says one of the hardest things for entrepreneurs to

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48:44

You Just Lowered the Value of Your Business

21 Hats Podcast ·

2026/09/15

Earlier this year, Ted Wolf suggested that Paul Downs should take a serious look at how artificial intelligence might improve his custom woodworking business. Paul was skeptical—but he invited Ted and his team to come visit the shop and see for themselves. This week, Ted reports back. He came away impressed by the business Paul has built but also convinced that Paul has a problem: As Ted sees it, too much of what makes the company work still resides in Paul’s head. Ted believes AI could help capture

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38:41

Dashboard: He Sold the Business. The Regrets Came Later

21 Hats Podcast ·

2026/09/11

Kevin Donnelly was 44 when an unsolicited offer set in motion the sale of the telecommunications company he had spent nearly 20 years building. The business had grown to more than 600 people in 38 cities and about $50 million in revenue, and Kevin says the deal itself worked out well for him financially. But that doesn’t mean he looks back on the experience without regret.What bothers him most is what happened to the people who helped him build the company. After the sale, employees started getting

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53:04

She Thought She Was Building a Prospecting Tool for...

21 Hats Podcast ·

2026/09/08

This week, Jaci Russo, Liz Picarazzi, and David C. Barnett talk about something entrepreneurs are always being told they have to do: innovate. But how do you know which ideas are worth pursuing, how much time and money to put into them, and when an experiment starts to become something much bigger? Jaci Russo may be finding out. What started as a prospecting system she built for herself—with AI, verified data, and a simple CRM—has turned into ProspectDaily, a subscription product that attracted more

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31:11

Dashboard: The Competitive Advantage AI Can’t Copy

21 Hats Podcast ·

2026/09/04

When Nathan Miller started Rentec Direct almost 20 years ago, he wasn’t trying to disrupt an industry. He was a small landlord who couldn’t find affordable software that did what he needed, so he built his own. Other landlords started using it, then paying for it, and over time Rentec carved out a meaningful place in what became an increasingly crowded and well-funded market.Nathan says the company has managed to keep growing not by trying to match its venture-backed competitors dollar for dollar,

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52:28

We’re Growing. Now I Want to Make Money

21 Hats Podcast ·

2026/09/01

This week, Sarah Segal tells David C. Barnett and Jay Goltz that she has decided it’s time to pay more attention to something that can occasionally get lost amid the other demands of running a business: making money. Sarah’s agency is having a very good year, with revenue growing 40 to 50 percent. But she’s realized that growth alone isn’t enough. She wants to know exactly what it costs to hire each employee, what it costs to service each client, whether her fees are covering those costs—and what

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39:23

Dashboard: Stop Asking How to Use AI

21 Hats Podcast ·

2026/08/28

Business owners are being told constantly that they need to figure out how to use AI. Deb Weidenhamer thinks that may be the wrong place to start. Instead, she says, owners should look for the places where their businesses are already struggling: Where are you wasting time? Where are you losing money? Where are customers getting frustrated? Then ask whether AI can help.In this week’s Dashboard, Deb, author of AI for Real Companies: A Practical Guide to Smarter Systems and Stronger Profits, walks us

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50:21

Best of: Selling My Business Nearly Broke Me

21 Hats Podcast ·

2026/08/25

This week, we revisit a conversation with Laura Zander that we first published last year, shortly after she and her husband Doug sold Jimmy Beans Wool, the business they had spent more than two decades building. Laura had been preparing to sell for years. She had kept the company’s books clean, built systems that could survive without her, and cultivated relationships with potential buyers. In other words, she had done many of the things owners are told they should do to prepare for an eventual

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37:41

Dashboard: Is Staying Small Selfish?

21 Hats Podcast ·

2026/08/21

I met Lamar Tyler, founder of Traffic Sales & Profit, a couple of years ago at a Zone of Genius conference, where I interviewed him on the main stage. It quickly became clear that Lamar, who helps business owners grow, had a lot of smart, practical advice to offer, and I’ve been following him ever since. He recently posted something on LinkedIn that stopped me: “Staying small as a Black business owner is selfish.” Lamar, obviously, was speaking primarily to Black entrepreneurs, but his challenge

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43:43

With My New Rent, I Will Clear Nothing

21 Hats Podcast ·

2026/08/18

This week, we start with a business owner who’s just learned his rent is jumping 40 percent and who sees three options: accept the new rent and essentially work for free, move and start over, or shut down and get a job. But when Paul Downs, Jay Goltz, and Ted Wolf do the math, they see another option—one the owner doesn’t seem to have considered.From there, the conversation turns to the choices owners make when the answer isn’t obvious. Paul, as it happens, is wrestling with two of those himself

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36:42

Dashboard: It’s Not That Earnouts Are Bad. It’s That...

21 Hats Podcast ·

2026/08/14

Conventional wisdom about selling a business is pretty clear: If at all possible, get your money at closing. Don’t leave a big chunk of the purchase price dependent on the future performance of a business you no longer control. David C. Barnett, who helps people buy and sell businesses, has challenged that conventional wisdom, arguing that earnouts and other forms of deferred payment can sometimes help buyers and sellers get better deals done. Josh Patrick, who has owned and sold businesses himself

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43:50

My Succession Plan Just Moved to Montana

21 Hats Podcast ·

2026/08/11

Jaci Russo has had quite a summer. First, her husband and business partner, Michael, underwent an unexpected quadruple bypass. Fortunately, Michael's recovering well, and their branding agency passed an important test: With both founders largely out of commission, the team kept the business running and the clients happy. But that wasn't the only surprise Jaci had to deal with. For the past several years, she and Michael thought they knew exactly how they would eventually leave the business. They had

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33:51

Dashboard: The Problem with Retainers (and Other...

21 Hats Podcast ·

2026/08/07

If you've built a successful business, you've likely been told the path to more success is obvious: hire employees, land bigger clients, lock in recurring revenue with retainers. But what if those aren't signs of progress? What if they're traps?This week, I talk with Pia Silva, author of Scale Solo, who argues that many of the traditional rules of entrepreneurship simply don't apply to solopreneurs. She explains why hiring too soon can derail a business, why retainers often aren't nearly as

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50:29

You’re Pre-Qualified for a 13% Loan! (That Really...

21 Hats Podcast ·

2026/08/04

This week, we begin with the story of Paloma Corona, the owner of a thriving preschool in Los Angeles who needed money to expand to a second location. She thought she was borrowing at an annual percentage rate of 13 percent. In reality, the effective APR was 170 percent. She also thought she was taking out a loan. Instead, she was placed in a merchant cash advance—an increasingly common form of financing that can sidestep many of the laws governing traditional loans. The daily payments quickly began

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39:35

Dashboard: The ESOP Risk Nobody Talks About

21 Hats Podcast ·

2026/07/31

ESOPs are often presented as one of the best ways for a business owner to exit. You preserve your company's independence, reward the employees who helped build it, and create a retirement benefit that can be life-changing for the people who stay with the business. What gets less attention is that ESOPs are still businesses. They can lose customers. They can hit hard times. And because employees' retirement savings are often tied to the company, the stakes can be even higher than they are at a

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