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
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.
Nov 7, 2022 • 22min
Dashboard: Don’t Leave It to Your CPA
This week, Gene Marks tells Loren Feldman that there are still lots of ways to save on taxes this year, but he also issues a warning: It’s a mistake for owners to just take their financials to the same CPA every year and assume he or she knows everything. Every few years, Gene says, you should take your returns to a different accountant and see if fresh eyes spot alternative tax opportunities for you to consider. Plus: Why Gene thinks you should ignore those third-quarter GDP numbers, and why he says there are times when owners should fight back rather than accept a bad online review.
Nov 1, 2022 • 47min
Should You Be in a Business Group?
This week, in episode 130, Sarah Segal, Jay Goltz, and special guest Leo Bottary have a hype-free conversation about why peer-advisory groups like Vistage, YPO, and EO can be life-changing for business owners and why they’re not for everyone. Sarah has been wondering if they’re for her. Jay, who’s been in six different peer groups, says it can be worth the price of admission just to see how other owners run their businesses—but there are reasons he keeps leaving the groups he joins. And Leo is a former Vistage employee who has written multiple books on peer groups and has built a related consulting practice. Surprisingly few business owners belong to a peer group. Are they missing out? All three of my guests suggest questions to consider before deciding for yourself.
Oct 31, 2022 • 19min
Dashboard: Would You Hire Them Again?
Kurt Wilkin, co-founder of HireBetter, tells Loren Feldman he thinks concerns about a recession are largely media-driven, but if your business is slowing, this might be a good time to reevaluate your team: Are you happy with everyone you’ve hired? Plus: What does it mean that wages kept rising in the third quarter? Should job listings include salary ranges? And what would Kurt tell business owners who struggle with compensating themselves?
Oct 25, 2022 • 40min
A Founder’s Year: Successful Raise, Fast Growth, and Mental Health Issues
This week, in episode 129, Hans Schrei tells Shawn Busse why this has been a difficult year at Wunderkeks—despite many outward signs of success. It has to do with buying into the need to raise money and shoot the moon. It has to do with accepting the accolades that come with entrepreneurial achievement and then questioning your own self-worth when those accolades stop coming. It’s what Hans calls, “the miracle worker complex.” Hans and Shawn also discuss what it means to rely upon a sales platform like Amazon. Do you own the customer or does Amazon? And Shawn explains the biggest takeaway from his most recent Vistage meeting.
