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 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.
Oct 24, 2022 • 23min
Dashboard: Gene Marks Has One Piece of Tech Advice
Before you spend more on technology, he says, you might want to figure out how to make the best possible use of the tech you already have. Crazy, huh? Gene also talks about the key elements of a buy-sell agreement, how to get your employees to actually use your CRM system, and whether all of our ever-expanding array of productivity tools actually help productivity.
Oct 18, 2022 • 49min
Rule No. 1: We Will Not Have Civil Wars
This week, in episode 128, Shawn Busse, Paul Downs, and Liz Picarazzi talk about why it’s so easy for tension to break out inside a business. Liz sees tension brewing between her people in the office and her people in the field. Shawn often sees friction at businesses between sales and those who have to deliver what sales sells. Paul says there’s always the potential for tension when a project gets handed from one set of workers to another, and he’s created a very deliberate process to address it. We have, he says, “really tamped down the civil wars and started solving the problems, as opposed to letting them fester.” Plus: Are Shawn and Liz going to hit their numbers this year? And have the owners seen their health insurance rates for next year?
Oct 17, 2022 • 31min
Dashboard: Victor Hwang on Entrepreneurship in America
Founder of entrepreneurial advocacy organization Right to Start, Hwang suggests bipartisan policy changes that would help Americans build more businesses. He also talks about what he learned about entrepreneurs on his recent cross-country roadtrip, why funding of U.S. businesses is broken, and what Americans really think of business owners.
