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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

18:22

Dashboard: Do You Know What Your Margins Are?

21 Hats Podcast ·

2023/09/25

This week, Tracy Bech talks about why it’s important, from time to time, to review your margins, to compare them with those of others in your industry, and to look for ways they might be improved. You might even find ways to adjust your business model. The first step, of course, is to make sure you know what those margins are. Plus: when is it time to start thinking about next year?

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43:02

I Would Have Been a Sub of a Sub of a Sub

21 Hats Podcast ·

2023/09/19

This week, in episode 168, Shawn Busse, Paul Downs, and Liz Picarazzi talk about when it makes sense to walk away from a client. Liz, for example, is tired of dealing with bureaucracy and being at the bottom of the food chain. In one instance, she was so turned off that she actually recommended a competitor for a job she no longer wanted. Paul has a simple test: If it’s easy work for a bad client, okay, fine. But if it’s hard work for a bad client, “Just don’t do it.” Of course, there are times in

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21:07

Dashboard: The Big Issues Looming for Small Businesses

21 Hats Podcast ·

2023/09/18

John Arensmeyer explains what the end of pandemic-era childcare support will mean for businesses. He also talks about the Department of Labor’s proposed overtime rule and what’s at stake for business owners if the government shuts down. Plus: owners say banks are getting harder to deal with.

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45:57

The Temptation of Private Equity

21 Hats Podcast ·

2023/09/12

This week, in episode 167, Shawn Busse, Jennifer Kerhin, and William Vanderbloemen discuss private equity. Both William and Jennifer have been getting emails and calls from representatives of PE firms who come promising all kinds of gifts—connections, expertise, money to invest in the business, and money to take off the table—which is why the temptation can be great. “If anybody even just offered me a three-day vacation, I think I would jump at it,” Jennifer jokes. But of course PE firms do exact a

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38:07

Bonus Episode: When Private Equity Comes for Your...

21 Hats Podcast ·

2023/09/05

This week, Dr. Randy Spencer talks about the changes that have been roiling the vet business. For one thing, that pandemic puppy boom we all heard about has brought additional stress to veterinary workers who had already had more than their share. For another, there’s been a wave of corporate money and private equity flowing into the industry. That sounds as if it could be a good thing. And in fact, Spencer says he’s been dodging a constant flow of acquisition inquiries for years. But the big money

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41:20

I Didn’t See All the Danger Signs

21 Hats Podcast ·

2023/08/29

This week, in episode 166, Mel Gravely—the newest addition to our podcast team—tells Shawn Busse and William Vanderbloemen how he bought a Cincinnati construction business in 2005 even though the company wasn’t doing well, even though he knew nothing about construction, and even though the company had been shopped to everyone who did know construction. As you’ve probably guessed, things worked out just fine for Mel, who is now focused on putting a plan in place that’s designed to keep Triversity

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50:44

The Toughest Conversation

21 Hats Podcast ·

2023/08/22

This week, in episode 165, Paul Downs, Jay Goltz, and Laura Zander don’t hold back. Laura and Jay both say their sales are coming in well below expectations. Not surprisingly, Jay has a five-point checklist that he’s using to assess and address his shortfall. Laura’s situation involves a marketing team that she says has been feeling stressed and is coming apart, with lots of crying and arguing. “They’re just collapsing,” she tells us. Paul, meanwhile, says his sales aren’t bad, but he’s got one

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18:51

Dashboard: Why Business Owners Don’t Like This Economy

21 Hats Podcast ·

2023/08/21

Gene Marks tells Loren Feldman that by almost any measure the economy continues to perform quite well. And yet, business owners don’t seem to believe it. Why is that? Gene says owners have some cause for concern. In fact, he expects a slight recession or slowdown in the next three to six months—of course he’s been saying that for more than a year now. “One of these days,” he says, “I’m going to be right.” Plus: Gene highlights two significant tax credits that most business owners don’t know

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45:51

When Business Owners Burn Out

21 Hats Podcast ·

2023/08/15

This week, in episode 164, Shawn Busse and Jay Goltz discuss a recent Business Journal report that a lot of business owners are feeling burned out. Why is that, and what can owners do to avoid it? And have either Shawn or Jay been there? Plus: Shawn brings us up to date on the leadership transition he’s initiated, and—believe it or not—Jay has had another revelation about ESOPs. Also, do business owners need better regulation or no regulation? And which regulations are annoying Shawn and Jay the

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23:58

Dashboard: The Big Story in Small Business

21 Hats Podcast ·

2023/08/14

This week, Gene Marks and Loren Feldman agree that artificial intelligence is becoming the biggest story in small business, with Gene highlighting a slew of AI tools that business owners can put to use right now. Gene also issues a warning that owners who do not start paying attention are taking a much bigger risk than they may realize. Plus: Gene also talks about team-building platforms that can help owners engage their employees, especially those working some or all of the time from home.

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44:55

Can I Go Dig a Hole?

21 Hats Podcast ·

2023/08/08

This week, in episode 163, Liz Picarazzi, Jennifer Kerhin, and Sarah Segal talk about whether they ever wish they could go back to their corporate lives. For Liz, there was a period during the early days of COVID. For Jennifer, it was when she made the transition from a consulting business to an employee business. These days, none of them can imagine going back—although Sarah did have a rough week recently when she lost two clients. “It's just the way of the world,” she tells us. “When businesses

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19:03

Dashboard: There’s Still Time

21 Hats Podcast ·

2023/08/07

Yes, it’s August, but Tracy Bech — co-author of “60 Minute CFO” — tells Loren Feldman it’s not too late to assess where your business stands and take steps to hit your numbers. Tracy also talks about what prompted her to take her own financials seriously, what owners can do if their revenue isn’t meeting expectations, and why she kind of likes recessions but isn’t disappointed we haven’t had one.

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34:32

What’s Going to Happen to My Business?

21 Hats Podcast ·

2023/08/01

This week, in episode 162, Jay Goltz tells us that, on second thought, he did learn something important watching HBO’s Succession. He still wants to work as long as he can—even if that means dying at his desk—but he now realizes, thanks in part to Logan Roy, that he needs to put a plan in place in case he were to get hit by that proverbial bus. This realization was also furthered by hearing the story of a 51-year-old entrepreneur who died in his sleep recently, leaving his wife to figure out how to

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25:05

Dashboard: A Mass-Extinction Event for Startups?

21 Hats Podcast ·

2023/07/31

This week, Gene Marks tells Loren Feldman that the Silicon Valley notion that startups are threatened with extinction is ridiculous. In fact, new business openings have been surging. The real problem in Silicon Valley is the venture-backed business model. Plus: Gene also talks about a way for small businesses to help their employees get health insurance without having to actually offer health insurance. And Gene also tells us about a lesson in regulation he learned from an eight-year-old

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41:26

Escaping the Valley of Death

21 Hats Podcast ·

2023/07/25

This week, in episode 161, Shawn Busse tells Jay Goltz and Jennifer Kerhin that he’s realized that his business, too—like Jennifer’s—is stuck in the valley of death that we first discussed a couple of episodes ago. Shawn’s realization prompts a discussion of what it takes to cross the desert and get out of the valley. We also have a surprisingly entertaining and enlightening conversation about insurance that makes clear why you should occasionally review what policies you have and why you have them

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28:09

Dashboard: A Tsunami of Regulation

21 Hats Podcast ·

2023/07/24

This week, Gene Marks tells Loren Feldman that it’s hard enough trying to run a small business in 2023, but just try running one in a blue state, where he says businesses have been subjected to a tsunami of regulation mandating things like paid time off and safe working conditions. Gene also talks about what’s going to happen to all of that unused commercial office space and whether there’s any reason for businesses to try out the new Twitter clone, Threads.

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44:06

Bonus Episode: The Long Journey to Really...

21 Hats Podcast ·

2023/07/21

If you’ve been listening to this podcast, you know that we’ve been taking periodic dives into the world of employee stock ownership plans. We started down this path because Jay Goltz was thinking about his own succession issues. In a series of podcast episodes and conversations and seminars over the course of more than a year, Jay progressed through the three stages of ESOP discovery: First, he had his eyes opened. (“Wait a second. If you’re an ESOP, you don’t pay taxes?”) Then he got a little

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54:12

Is Anybody Listening to Me?

21 Hats Podcast ·

2023/07/18

This week, in episode 160, Shawn Busse, Paul Downs, and Jennifer Kerhin talk about the challenges of communicating with employees, especially in the post-pandemic world. It’s hard enough to get aligned on mission and vision, but how do you connect with an employee you’ve never actually met in person? Is that even possible? We also discuss Jennifer’s realization that she has over-performed on sales but under-performed on marketing, which is part of the reason she’s re-doing her website. “I need a

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25:43

Dashboard: ‘ChatGPT on Steroids’

21 Hats Podcast ·

2023/07/17

This week, Gene Marks gives Loren Feldman a preview of what Microsoft is cooking up with a product called Copilot that Gene expects to be released before the end of year and that he promises will “rock your world.” Like ChatGPT, Copilot will access data on the internet but it will also be incorporated into all of Microsoft’s existing products so that it will also be able to access data in, say, your customer relations management software. That means you’ll be able to do things like ask Copilot to

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49:39

‘You’re in the Valley of Death’

21 Hats Podcast ·

2023/07/11

This week, in episode 159, Shawn Busse, Jay Goltz, and Jennifer Kerhin talk about that difficult transition most growing businesses endure when the owner can no longer handle all of the most important tasks herself but also can’t quite afford to hire the people she needs to lighten her load. It’s part of the reason Jennifer, as she’s told us in previous episodes, has been working 12-hour days, six days a week. It’s a challenging transition, and it has a name: It’s the “valley of death,” says Shawn,

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527 results

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