

21 Hats Podcast
21 Hats
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 won’t even discuss behind closed doors: whether their businesses are as profitable as they should be, whether they are willing to give up some control to an investor in order to grow faster, why they had to lay off employees, how they wound up with way too much inventory, why they don’t have a succession plan, and even why they are concerned about their own mental health. Visit 21hats.com to hear all of our podcast episodes, read episode transcripts, and learn more. The show is produced by Jess Thoubboron, founder of Blank Word.
Episodes
Mentioned books

Jan 20, 2023 • 43min
Bonus Episode: A New Way to Sell Your Business
Learn about Teamshares, a company that buys struggling businesses from retiring owners and turns their employees into owners to address income inequality. Discusses challenges and lessons from acquiring over 60 businesses. Highlights the importance of recruiting and training leaders, maintaining relationships with former owners, and implementing employee stock ownership plans. Emphasizes the challenges of running a small business and the need for continuous learning, good financial practices, and fair compensation for employees.

Jan 17, 2023 • 50min
I’ve Always Been Afraid to Raise Prices
This week, in episode 139, Jay Goltz, Dana White, and Laura Zander have a wide-ranging conversation that starts with the challenge of pricing. Do you set prices based on what you think the market will bear? Or do you set prices based on your own rising costs and what you need to charge to make a profit? And how much profit should a business expect to make? Along the way, the owners also discuss why Laura wants to keep buying businesses (don’t tell her husband, Doug), what Dana needs to do to get her new salon open at Fort Bragg, and why both Dana and Laura are going all-in on influencer marketing. Jay, on the other hand, isn’t entirely convinced that social media marketing works for his picture-framing business. Plus: Should a business owner know every employee’s name? What if you have 130 employees?

Jan 16, 2023 • 26min
Dashboard: The State of Small Business, 2023
John Arensmeyer, founder and CEO of Small Business Majority, an advocacy group for entrepreneurs and businesses, talks to Loren Feldman about how businesses are faring, what issues they are most concerned about, and where his organization is focusing its energy. Among other things, they discuss access to capital, the need for immigration reform, who benefits from non-compete agreements, California’s experiment in fast food regulation, and the Labor Department’s approach to independent contractors.

Jan 10, 2023 • 50min
How’s Your Compensation Plan Holding Up?
This week, in episode 138, Shawn Busse, Liz Picarazzi, and William Vanderbloemen discuss what it’s been like trying to make sense of employee compensation in a time of COVID, the Great Resignation, inflation, and a looming recession. Shawn’s business model is evolving, and he’s trying to adjust his mix of employees to fit the new model with as little disruption as possible. Liz is expecting a year of big growth and is assessing how that will affect her staffing needs—especially as she introduces new benefits, including health care. And William is trying to create a more sustainable compensation structure while also breaking his employees’ expectation that they will always get a year-end bonus. Plus a listener asks: What tasks are the owners still doing, even though they know it’s not worthy of their time? (Aside from participating in this podcast, of course.)

Jan 9, 2023 • 21min
Dashboard: Check Out the New Retirement Rules
This week, Gene Marks tells Loren Feldman that the politicians behind Secure 2.0 are smarter than you think. The omnibus spending bill that recently became law includes a slew of changes to the rules that govern retirement benefits. The changes are designed to encourage both employees and owners to sock away more money, and they include a $1,000 tax credit per employee for owners who match employee savings. Plus: are non-compete clauses of any value to small businesses? And the IRS blinks on its requirement that third-party payment platforms issue 1099-K forms.

Jan 3, 2023 • 57min
The Hard-Nosed Business Case for Employee Ownership
This week, in episode 137, Jay Goltz explains how he got interested in selling a percentage of his business to his employees and why he quickly lost interest once he started reading books, attending seminars, and talking to accountants and lawyers who specialize in employee stock ownership plans. To Jay’s ear, they all made ESOPs sound expensive, complicated, and risky. This was not something he needed to do. So why go to the trouble? Why take the risk? But he kept asking questions, and over time, he sensed that many of the problems he was being warned about didn’t have to be problems. As of now, he’s pretty much concluded that an ESOP could help him secure retirement for his employees while generating more profit for his business. In fact, he says, “I'm confident I can make more owning 70 percent of the company than I am now owning 100 percent.” But he still has a few lingering questions, which is why we invited Corey Rosen to join the conversation. Corey helped draft the legislation that created ESOPs, he's the founder of the National Center for Employee Ownership, and he literally wrote the book on how the plans work. All of which led to an inevitable question for both Jay and Corey: If ESOPs are so great, why are there so few of them?Show Notes: Here’s Corey Rosen’s most recent book, written with John Case: “Ownership: Reinventing Companies, Capitalism, and Who Owns What.”Here’s a previous book Corey wrote with Scott Rodrick: “Understanding ESOPs.”And here’s a book written by Jack Stack and Bo Burlingham: “A Stake in the Outcome.”

Dec 19, 2022 • 23min
Dashboard: Business Regulation Even Business Owners Will Support?
In our last episode of the year, Gene Marks tells Loren Feldman he actually thinks business owners will like the new law in California that will create councils to regulate the fast food industry. In fact, Gene thinks there’s a chance it will succeed and spread to other regions and other industries. He also explains why he thinks businesses should be on Yelp, why he’s still excited about what Elon Musk is doing with Twitter, and why he thinks interest rates will be the small business story of 2023.

Dec 13, 2022 • 47min
Jay Goltz’s 12-Step Business Check-Up
This week, in episode 136, Shawn Busse, Jay Goltz, and Sarah Segal talk about what they hope to accomplish in 2023. Sarah’s moving into new offices, aiming for 20-percent growth, and hoping to land a chocolate company as a client. Shawn’s looking for new space, too, and attempting to reposition his business to shake the corrosive effects of the pandemic. And Jay’s employing a methodical 12-step process to assess how his business is performing: Hiring? Check. Pricing? Needs work. Inventory levels? Way out of line. Office technology? Major problems. And then there are his ongoing efforts to mentor his two sons in the business and prepare for the inevitable. These days, Jay tells us, he’s especially careful when getting in front of buses. If you’ve been listening to this podcast, you know our business owners discuss their journeys with unusual candor. But in some episodes we go especially deep. This is one of those episodes.

Dec 12, 2022 • 21min
Dashboard: The Problem with Charging by the Hour
This week, Gene Marks and Loren Feldman talk about how charging by the hour actually punishes you for being good at your job—but there’s a good reason Gene does it anyway. Plus: Gene also discusses his one concern about hiring ex-offenders and issues a warning to business owners about their remote employees. Gene thinks they’re probably stealing from you.

Dec 6, 2022 • 50min
I Want to Double Sales Again Next Year
This week, in episode 135, Shawn Busse, Paul Downs, and Liz Picarazzi talk about their plans and goals for 2023. Shawn, whose marketing efforts still haven’t recovered from the pandemic, is hoping to build on the success of a recent event. Paul, coming off his best year ever, is investing $150,000 in a marketing campaign, including a new website targeting a different set of customers. And Liz, too, is attempting to shift her customer base, in her case from residential to municipal work. More immediately, however, Liz, who does not relish dealing with legal issues, has to decide how to confront a copycat competitor.