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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

24:29

Dashboard: Your Last-Minute, Year-End Tax Moves

21 Hats Podcast ·

2023/12/11

This week, Gene Marks shares his suggestions for anyone looking to save a little on taxes. Start with your retirement account. Better yet, start planning ahead for next year. Plus: What’s the best CRM for solopreneurs and microbusinesses? What artificial intelligence apps for business are worth trying right now? And what does Philly native Gene make of the $140 Philly cheesesteak?

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45:27

We Need to Go Back to Marketing for Humans

21 Hats Podcast ·

2023/12/05

This week, in episode 176, Paul Downs tells Jay Goltz and Jaci Russo about the latest developments in his year-long campaign to stop relying so heavily on Google AdWords. At a specially arranged, two-day marketing event, Paul got to sit down with a series of architects and designers who had already been vetted and who he hopes will become repeat customers. So far, Paul says, the results look promising. Plus, we also discuss: Do you write your website copy to please Google or to please people? Is

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27:48

Dashboard: Don't Blame Your CRM

21 Hats Podcast ·

2023/12/04

This week, Gene Marks talks through the latest developments in customer relationship management software, which is both his area of expertise and a real pain point for many business owners. Among other things, Gene tells us about the impact artificial intelligence is already having on CRM, including what A.I. makes better as well as what it makes worse. Plus: How do you get salespeople to use your system properly? And what should you do if you’re completely frustrated and ready to dump your

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51:00

Bonus Episode: Are Salespeople Built or Born?

21 Hats Podcast ·

2023/11/28

It used to be that best practices in sales were pretty standard across the board. But since the pandemic and with the advent of artificial intelligence, says Lance Tyson, founder of the Tyson Group sales consultancy, it’s like the Wild West out there. Suddenly, everyone’s playing by different rules, and the best sales approach can vary, depending on the seller, the target, the industry, the region of the country. The keys, Tyson says in this week’s bonus episode, are to pay attention and stay

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36:58

Clients and Taxes and Bears, Oh My!

21 Hats Podcast ·

2023/11/21

This week, in episode 175, Jaci Russo explains how she put an end to her eight-month drought of new clients. Jennifer Kerhin takes us through the bureaucratic nightmare of managing remote workers based out of state (“That is a headache that I don't wish on my worst enemy,” says Jaci, who has found a way to sidestep the problem). And Liz Picarazzi brings us up to date on her ongoing struggle to get her trash enclosures certified as bear-resistant. The common thread to these challenges may lie in

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21:20

Dashboard: It’s the Data, Stupid

21 Hats Podcast ·

2023/11/20

This week, Black Friday and Small Business Saturday will represent hugely important shopping days for many retailers. But Gene Marks tells Loren Feldman that the sales those days generate aren’t necessarily as important as the data they generate -- so long as the retailers are smart enough to capture it. Gene also talks about why business owners need to understand that when they sign their tax returns, they—and not their accountants—are responsible for what the returns show. Plus: why Gene loves

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38:43

Start Up, Throw Up, and Grow Up

21 Hats Podcast ·

2023/11/14

This week, in episode 174, Dana White drops a few surprises. When we began this podcast in 2020, Dana had two promising hair salons in Detroit that she’d named after her grandmother, Paralee Boyd. She had an innovative business model designed specifically for women with thick and curly hair. And she was on her way to winning a prestigious business plan competition. All of which presented her with a wide array of opportunities to consider. Would she continue to bootstrap? Would she franchise? Would

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50:29

The I-Hate-Marketing Approach to Marketing

21 Hats Podcast ·

2023/11/07

This week, in episode 173, Shawn Busse tells Jay Goltz and Mel Gravely why he doesn’t want his firm, Kinesis, to be known as a marketing agency. Part of it is his sense that people just don’t trust marketers. But Shawn also believes that what Kinesis offers its clients is much more than just marketing. Hearing that prompts Mel to take us through his recent decision to spend a lot of money rebranding his construction business, which he says created alignment throughout the business and would have

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24:14

Dashboard: Can You Fire Employees Who Won’t Return to...

21 Hats Podcast ·

2023/11/06

This week, Gene Marks warns business owners that the National Labor Relations Board has taken an action that could make it harder to fire employees who won’t come back to the office. But is that really the case? Gene’s also concerned about a new rule proposed by the Equal Employment Opportunity Commission that makes it even more important that business owners review their policies and training regarding harassment of employees. And then Gene reviews the case of an employee who filed some relatively

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43:11

Best of: Sometimes, Dreams Do Come True

21 Hats Podcast ·

2023/10/31

If you’ve been listening to this podcast, you know we spend a lot of time talking about all of the things that can go wrong for a business owner. And yes, in part because we started recording these conversations just a couple of months before the pandemic hit, we’ve had plenty to talk about. Even this year, with the worst of the pandemic behind us, we’ve been talking about everything from excess inventory to lost clients to layoffs to ineffective marketing to surviving the valley of death. So, with

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26:29

Dashboard: It’ll Change Everything

21 Hats Podcast ·

2023/10/30

This week, Shawn Busse tells Loren Feldman why he’s long been skeptical of big data, especially the data many businesses collect from their customers. What’s the alternative? Shawn suggests doing something radical and having actual conversations with your customers, especially your best customers. Shawn also talks about why it seems so many businesses are struggling even as the economy is surging, at least according to the latest GDP figures. Plus: What exactly is wrong with the titans of Silicon

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41:50

And Some Days the Bear Eats You

21 Hats Podcast ·

2023/10/24

This week, in episode 172, Liz Picarazzi tells Jay Goltz and Sarah Segal that her trip to a bear sanctuary in Montana to get her trash enclosures certified as bear-resistant did not go precisely as planned. Because of a logistical snafu, she has not yet obtained either the certification or her real goal: a marketing video of the grizzlies attempting to crack open her baited enclosure. Fortunately, things went better for Liz in a more traditional marketing venue, a trade show in Chicago where she

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20:36

Dashboard: Gene Marks Expects an A.I. Backlash

21 Hats Podcast ·

2023/10/23

For months, Gene has been telling us about all of the cool things we’ll be able to do with Microsoft’s Office 365 and Google’s Workspace when those companies integrate artificial intelligence into their platforms. Gene’s still excited about the possibilities, but he’s also more than a little annoyed, because both Microsoft and Google are planning to charge us quite a bit more for their A.I. enhancements. Gene also talks about automated invoicing, which he believes is going to displace a lot of

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43:10

We Haven’t Signed a New Client in Eight Months

21 Hats Podcast ·

2023/10/17

This week, in episode 171, we meet Jaci Russo, the co-founder and CEO of BrandRusso and the latest addition to the 21 Hats Podcast team. Jaci tells Jay Goltz and Laura Zander how she went from working for Barry Diller to starting her marketing agency. Jaci also explains why she recently decided to introduce a four-day workweek and why she thinks her agency has now gone eight months and counting without signing up a new client—the longest such stretch in more than 20 years in business. “I find it

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21:41

Dashboard: The Insane Burden of Health Insurance

21 Hats Podcast ·

2023/10/16

This week, we learn that Gene Marks and Bernie Sanders agree on something, which is that there are better ways to handle health insurance than making business owners responsible for providing it to their employees. Isn’t running a business hard enough without this financial and bureaucratic burden? Does it really have to be this way? Plus: Why Gene thinks what he calls “the era of the worker” won’t last forever. And what business owners need to know and do before they lay off or fire employees.

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23:00

Bonus Episode: An Accidental Entrepreneur

21 Hats Podcast ·

2023/10/13

It took a series of sad losses to turn banker Channon Kennedy into an entrepreneur. If a friend hadn’t lost his son and if Channon’s mother and sister hadn’t been diagnosed with cancer, she never would have designed, prototyped, manufactured, and started selling the Morgan Square, a tool that can save carpenters time while framing a project. CDhannon is just getting started, but we’ll keep in touch as her journey continues.

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35:36

Bonus Episode: The Employee Engagement Industry Has...

21 Hats Podcast ·

2023/10/10

In this week’s bonus episode, Bill Fotsch, a business consultant, explains why he thinks much of the effort that he and many others have put into creating employee engagement over the past three decades has been wasted effort—well intentioned, but wasted. The fact is, Fotsch says, employees today are no more engaged than they were some 30 years ago when the concept of employee engagement first gained currency. So what’s the answer? Fotsch has come to the conclusion that it’s something he calls

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43:15

It’s Like Planning Your Own Funeral

21 Hats Podcast ·

2023/10/03

This week, in episode 170, Jay Goltz tells Shawn Busse about the latest stop on his journey to figuring out whether an employee stock ownership plan is right for his business. Jay’s latest adventure includes waking up at 4:30 in the morning in Minneapolis too anxious to sleep—“Oh my God, what am I getting myself into here?”—and deciding to leave the seminar and drive back to Chicago. But on that six-hour return trip, Jay says his anxiety turned into clarity. In fact, he thinks he’s pretty sure he

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19:11

Dashboard: About That Shutdown

21 Hats Podcast ·

2023/10/02

When Gene Marks and I recorded this episode of Dashboard on Friday, we were pretty sure the government was going to shut down. That, of course, didn’t happen so you can fast-forward through our brief remarks early in the show—or perhaps you would enjoy hearing Gene state confidently that he’s known all along that a shutdown was inevitable. We also discuss what Gene’s been hearing from business owners as he criss-crosses the country talking to various groups. And Gene talks about the IRS’s decision

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40:04

I’ve Never Had to Lay off Anyone Before

21 Hats Podcast ·

2023/09/26

This week, in episode 169, Sarah Segal tells Shawn Busse that the other shoe has dropped. A couple of months ago, as she’s shared here previously, Sarah lost two big clients in one week. Now she takes us through her decision to lay off three of her employees, including what it means for the business and what it means for Sarah’s own role in the business. Before the layoffs, she had gotten to the point where she was working on the business—but now that’s changed. “I'm not working on the business,”

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