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
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.
Dec 5, 2022 • 25min
Dashboard: Okay, Boomer, What's Your Succession Plan?
Gene Marks tells Loren Feldman that he’s concerned that not enough business owners are thinking about the future and preparing for succession. Which leads to an obvious question: Does Gene have a succession plan? Hmmm. Plus: Gene has some suggestions for how businesses can better manage their relationships with vendors and suppliers. And what lessons should we take from the rampant fraud being revealed in the PPP program?
Nov 29, 2022 • 46min
Should We Tell the Employees?
This week, in episode 134, Shawn Busse, Jay Goltz, and Laura Zander talk about the buying and selling of businesses. Laura thinks her recent purchase of a small distribution business could change the trajectory of her whole company, helping her finesse the challenge of selling wholesale products to her retail competitors. Jay, meanwhile, has been trying to help an aging business owner sell the kind of business that too often just fades away. Underlying both discussions is an intriguing question: While it’s common practice for owners trying to sell their business to keep the potential sale a secret, fearing employees might otherwise flee, is that really the best approach? Or is it actually a betrayal? Plus: We answer a listener's question about finding the right balance between being a kind boss and being a pushover. And we play a quick game of Who Said It: Elon Musk or Mr. Burns?
Nov 22, 2022 • 48min
Are You a Good Negotiator?
This week, in episode 133, Paul Downs and Sarah Segal talk about their experiences negotiating, what they’ve learned and where they’ve struggled. One key factor, of course, is defining what constitutes a successful negotiation. As Paul points out, one definition is squeezing every last penny out of the other side. That is not Paul’s definition, especially when negotiating salary with a new employee. Sarah, meanwhile, discusses the tactics she uses to try to guide potential clients to the price and options she hopes they will accept. Plus: Sarah explains how she picked her new office space, and Paul explains why his experience with a Vistage peer group has been life-changing.
Nov 21, 2022 • 24min
Dashboard: Zip It And Do Your Job!
This week, Gene Marks tells Loren Feldman that he’s had it with “quiet quitting,” side hustles, and employees who won’t go the extra mile. It’s time, he says, for them to get to work. And if they don’t? Gene says they’re going to be looking for work, and it could happen much sooner than they realize. On a related note, Gene is also very excited about the “hardcore” changes Elon Musk is bringing to Twitter. We’ll see how that works out!
Nov 15, 2022 • 45min
For Richer, For Poorer
This week, in episode 132, Liz Picarazzi, Hans Schrei, and Laura Zander talk about something they have in common: They all own and run their business with a partner who also happens to be a spouse. Which suggests some interesting questions: Is someone in charge? How do they divvy up responsibilities? What do they talk about? What do they fight about? Do they fight in front of the employees? How do they make decisions? Who does the dishes? Do they ever wish they were not in business with their spouse? Do they know what would happen to the business if they were to divorce?
Nov 14, 2022 • 20min
Dashboard: How Gene Marks Stopped Sweating Health Insurance
You want to negotiate with Blue Cross every year? Go ahead. Gene Marks tells Loren Feldman he's found an alternative that he believes allows him to take care of his employees without the hassle of actually buying health insurance. Plus: Why Gene doesn’t discount his services for nonprofits and what he thinks is the most important takeaway for business owners from last week’s midterm elections.
Nov 8, 2022 • 47min
There’s Big Money All Over the Place
This week, in episode 131, Shawn Busse tells Jay Goltz and Sarah Segal that he sees all kinds of opportunities for small businesses, including his own, in the coming wave of climate-related government spending and tax credits. Count Jay among the convinced. He’s got four buildings, five vans, a truck, some Sprinters, and a parking lot where he could put a charging station. If there’s government money available for upgrades, he asks, “Why wouldn’t I do that?” Plus, Jay explains how he’s rethinking his search for an HR person. And Sarah tells us she’s ready to meet in the metaverse.
