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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

40:11

Managing Your Tasks, Your Credit Cards, and Your Anxiety

21 Hats Podcast ·

2024/02/27

This week, in episode 185, Jay Goltz, Jaci Russo, and Sarah Segal talk about whether it’s finally time for Jay to enter the brave new world of task-management software. That’s, in fact, what his two kids in the business are encouraging him to do. As it happens, Jaci and Sarah have tried most of the project-management tools out there—Monday, Basecamp, Asana—and they kind of love them, but with one caveat: They can be a lot of work. Which is all Jay needed to hear. After that, we talk about the

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28:01

Dashboard: When Is It Time to Panic?

21 Hats Podcast ·

2024/02/26

All businesses have ups and downs. This week, Tracy Bech, CEO of Starboard Collectives and co-author of the “60 Minute CFO,” offers some guidance on when to ride out a slow period and when to take action. Plus, she also talks about how she’s building an AI tool to help with financial analysis and when it makes sense to hire a fractional CFO.

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53:18

That Would Put Me Out of Business

21 Hats Podcast ·

2024/02/20

This week, in episode 184, Mel Gravely, Liz Picarazzi, and Jaci Russo talk about how they set prices. Jaci explains why she refuses to respond to requests for proposals. “We have not participated in a single RFP in 15 years,” she says, “and we won’t under my watch.” Mel explains how his construction company manages to get work despite always being among the highest-priced bidders (which is why he never gets government jobs). And Liz tells us what happened when she was forced to raise prices because

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22:13

Dashboard: Gene Marks Tries a Digital Marketing Test

21 Hats Podcast ·

2024/02/19

This week, Gene tells Loren Feldman about a little experiment he ran recently in which he boosted a post on X, formerly known as Twitter, that was designed to send people interested in his book on customer relations software to a landing page on his website. X reported that the post was a big success. But was it? Gene offers a slightly profane rebuttal. Plus: He also talks about three Jeff Bezos quotes that he believes can change how you run your business, and he explains how companies can commit

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49:54

‘I Had to Fire the Guy’

21 Hats Podcast ·

2024/02/13

This week, in episode 183, Paul Downs, Jay Goltz, and Sarah Segal talk about sexual harassment and where you draw the line with employees. Is it sexual harassment for one employee to ask another for a date? Is it sexual harassment to ask twice? Does it make sense to have a policy of zero tolerance? Or is it better to leave room for discretion and judgment? The conversation was sparked by a recent situation Jay experienced with an employee who had been with the company for almost three decades,

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22:49

Dashboard: What Can We Learn from Boeing?

21 Hats Podcast ·

2024/02/12

This week, Shawn Busse, who soon will be boarding an Alaska Airlines plane made by the Boeing Company to attend the 21 Hats Live event in Fort Worth, finds lessons for smaller businesses in Boeing’s struggles. For one thing, there’s always danger when combining the cultures of two different companies. Plus: Shawn, whose company, Kinesis, has been a certified B corp since 2016, talks about whether the certification is losing its luster.

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42:23

Why Would You Want to Own a Business?

21 Hats Podcast ·

2024/02/06

This week, in episode 182, Shawn Busse, Jay Goltz, and Jennifer Kerhin respond to a somewhat depressing view of business ownership offered by an investor who buys businesses for a living. That view, essentially, is that for most owners, building a business is a daily knife fight of long hours, unexpected risks, slow growth, and meager returns. In this episode, I read most of the investor’s observations to Shawn, Jay, and Jennifer, and get their reactions, which hit upon a bunch of issues that are

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29:17

Dashboard: Just Ignore Those New 1099 Rules

21 Hats Podcast ·

2024/02/05

That, at least, is what Gene Marks is planning to do. Gene tells Loren Feldman that the new rules, which are scheduled to take effect in March, would have a profound impact on many businesses, including his—if they are actually enforced. But Gene’s not convinced that’s going to happen. Before you relax, though, Gene’s even more worked up about the new guidelines coming from the EEOC regarding harassment in the workplace. Very few businesses, he says, are prepared for what’s coming. One warning: when

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50:01

Have We Been Too Generous With Employees?

21 Hats Podcast ·

2024/01/30

This week, in episode 181, Mel Gravely, Jaci Russo, and William Vanderbloemen talk about the possibility that, after several years of the Great Resignation and the labor shortage, some owners may have given away the store. We all know the risks of not offering employees enough. What are the risks of offering too much? How do you even know when you’ve crossed the line? The owners also discuss why this might be a good time to consider acquiring other businesses. “I think this is a time to

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19:43

Dashboard: Is Microsoft Copilot Pro Ready for Prime...

21 Hats Podcast ·

2024/01/29

This week, Gene Marks tells Loren Feldman that while he’s excited about all of the great stuff we will eventually be able to do with artificial intelligence, business owners should stay away from Copilot for now. As with a lot of Microsoft products, Gene says, you just don’t want to be an early adopter. Plus, Gene explains his not-completely-obvious fraud-prevention strategy: Make your people take vacations.

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48:57

We’re Making Good Money. I’m Not Sure How

21 Hats Podcast ·

2024/01/23

This week, in episode 180, Jay Goltz, Jennifer Kerhin, and Liz Picarazzi discuss their efforts to get a better grasp of what drives their profits. They ask how much of their finances they should manage themselves. And how much should they rely on an accountant or a fractional CFO? When does delegation become abdication? Jennifer says she’s benefitted from hiring a fractional CFO who has taken an active leadership role, including setting up a database that helps Jennifer see in real time whether the

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24:46

Dashboard: Is America Really Experiencing a Startup...

21 Hats Podcast ·

2024/01/22

Well, yes, actually, but Gene Marks and Loren Feldman discuss two questions: One, what exactly is driving the boom? And, two, are the startups substantial enough to matter? Or is this just about people losing their jobs and driving for Uber. Plus: what would you do if you owned fast food locations in California where the minimum wage for fast food workers will jump to $20 an hour in April. And what are business owners to make of the case the Supreme Court heard last week about the constitutionality

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53:48

The Worker Co-Op Solution

21 Hats Podcast ·

2024/01/16

In this week’s bonus episode, Cameron Madill takes us on his succession journey, which began years ago when he started having conversations with older business owners, many of whom seemed to feel trapped. They’d had a lot of success, they were proud of the business they’d built, but they weren’t sure what to do with it or how to leave it. None of the usual options seemed terribly appealing. Hoping to write a different ending, Madill, now in his 40s, started looking for better options much earlier

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21:24

Dashboard: AI, TikTok, and the Rise of Women Owners

21 Hats Podcast ·

2024/01/15

This week, Shawn Busse and Loren Feldman talk about some big changes coming to the world of small business. At his consulting firm, Kinesis, Shawn is already beginning to experience the impact artificial intelligence is having on his industry. He knows B2B business owners who are spending a lot of time on TikTok—and they’re not just watching dancing videos. And his client base has already shifted dramatically toward women-owned businesses.

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49:07

New Year’s Resolution? Make. Some. Money.

21 Hats Podcast ·

2024/01/09

This week, in episode 179, Shawn Busse, Paul Downs, and Laura Zander talk about why 2023 was so challenging for them and what they plan to do differently in 2024. “Last year was a year when I knew I was going to be making a bunch of investments and didn't expect to show much or any of a profit,” says Paul. “And I absolutely nailed that goal.” Shawn, meanwhile, thinks his new marketing scheme is working, and Laura is addressing her issues by going shopping — shopping, that is, for businesses. She’s

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24:55

Dashboard: The State of Small Business, 2024

21 Hats Podcast ·

2024/01/08

This week, John Arensmeyer, founder and CEO of the advocacy group Small Business Majority, tells us that he senses considerable optimism among the many business owners in his network notwithstanding some concern for looming policy and economic issues. Among those issues, John tells Loren Feldman are: access to capital, the cost of health care and health insurance, relations between franchisors and franchisees, price discrimination against smaller businesses, the burden of the new Corporate

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131:21

This Is What It Takes to Build a Business, Vol. 2

21 Hats Podcast ·

2024/01/02

This week, we take a look back at the conversations we had last year about the many rewards and responsibilities of business ownership, highlighting some of our happiest, smartest, funniest, and most difficult exchanges from the past year. Along the way, we discuss topics such as escalating salary demands, how much profit a business should make, a new way to sell a business, the problems with ESOPs, how to sell cookies on LinkedIn, breaking a million dollars in annual revenue, escaping the valley of

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47:58

Bonus Episode: The Unlikely Plan That Launched Down...

21 Hats Podcast ·

2023/12/19

So here was Muhammad Abdul-Hadi’s idea for a pizza joint: First, buy a building in one of the most troubled neighborhoods in one of the poorest big cities in the country. Open a restaurant despite having no experience in the food industry and do it during the pandemic when many restaurants are failing. And hire only people who, like Abdul-Hadi, are convicted felons. If that business plan sounds a little dicey to you, rest assured you would not be the first to suggest that to Abdul-Hadi. But he did

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24:11

Dashboard: Do the Math. Lean into A.I. Play Squash

21 Hats Podcast ·

2023/12/18

In our last conversation of the year, Gene Marks tells Loren Feldman about the nine habits that he believes have helped him build a business. Those habits include meeting regularly with his accountant, meeting regularly with his clients, and over-paying his employees. Gene saves what he considers the most important suggestion for last: Make time to enjoy your family.

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46:26

What Are Your Goals for 2024?

21 Hats Podcast ·

2023/12/12

This week, in episode 177, Shawn Busse, Liz Picarazzi, and Jaci Russo discuss what they learned in 2023 and what they expect from 2024. After a tough year, Shawn is optimistic that his clients, having survived the turbulence of the past few years, are ready to spend money and try something different. Liz explains why she’s been willing to discount her products as much as 40 percent on Cyber Mondays and tells us about some new products she has in the works. Early in the year, Jaci, thinking she was

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