x

75% of people globally want unbiased news (Pew Research) but are concerned they're not getting that.

Get balanced coverage with Symby. See how stories are covered across diverse outlets and spot when one side covers a story the other skips.

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

50:04

Straight Talk About ESOPs and Co-Ops and EOTs, Oh My!

21 Hats Podcast ·

2025/07/08

This week, in Episode 254, Jay Goltz, Mel Gravely, and special guest John Abrams have a frank conversation about what business owners can do to avoid what John calls the “fat-wallets-and-broken-hearts syndrome.” That’s his term for what can happen when an owner sells to private equity and the company ends up getting stripped. Jay, Mel, and John all agree they want no part of that. They all would like to see their businesses continue on without them. And yet, in thinking about succession, they’ve

en

43:21

Dashboard: A Big Beautiful Win for Small Businesses?

21 Hats Podcast ·

2025/07/07

That’s what Gene Marks thinks. In this week’s conversation, Gene lists the tax changes in President Trump’s big beautiful bill that he’s happiest about, while emphasizing that what he’s really happiest about is the tax certainty that passage of the bill creates for business owners. Gene also explains why he thinks owners who complain about Trump’s tariffs have no one to blame but themselves and why he’s not all that concerned about the uncertainty the tariffs are generating, including what will

en

56:54

Something’s Happening in the Job Market

21 Hats Podcast ·

2025/07/01

This week, in Episode 253, Paul Downs tells Kate Morgan and Liz PIcarazzi that he recently posted a job on Indeed and got 153 resumes—more than he’s ever gotten before, which prompted some interesting questions: What does this mean for business owners? Should a job posting be more about what the company expects from a candidate or more about what the company has to offer? Do the owners ask candidates to take personality tests? If the owners get 150 resumes, do they ask ChatGPT to review them? And

en

23:04

Dashboard: Three Metrics for ‘White Knuckle’ Times

21 Hats Podcast ·

2025/06/30

This week, Tracy Bech, co-author of “The 60-Minute CFO,” tells us that she normally recommends that business owners check 14 performance measures on a regular basis. But during uncertain times like these, Tracy says, there are three in particular to keep an eye on: gross profit margin, operating cash flow, and current ratio. In our conversation, she explains how they work, what they mean, and what to do if they’re flashing red. She also says you can download a free tool to track your cash flow at

en

54:21

Why Don’t You Just Sell the Business?

21 Hats Podcast ·

2025/06/24

This week, in Episode 252, David Barnett, Mel Gravely, and Kate Morgan discuss a somewhat unusual approach to succession, which is to not sell the business. Basically, it’s about taking a step back from leadership while maintaining ownership, and both Kate and especially Mel are moving in this direction. The approach can pay off financially in part because businesses often are worth more to the owner than they would be to a buyer. Why is that? As David explains, the business that the buyer buys

en

26:05

Dashboard: Don’t Believe the AI Hype (Yet)

21 Hats Podcast ·

2025/06/23

This week, Gene Marks tells us why he’s skeptical of corporate CEOs like Amazon’s Andy Jassy who have started telling employees that they are likely to lose their jobs as the company continues to adopt tools that use artificial intelligence. Gene thinks CEOs who blame AI for corporate layoffs are really covering for bad management. In fact, he thinks anyone who is already replacing employees with AI is a fool. On the other hand, Gene tells us he’s incorporating AI tools into almost every aspect of

en

46:42

‘America Sucks at Small Business’

21 Hats Podcast ·

2025/06/17

This week, in episode 251, we meet Dan Carmody, who has gained an unusual perspective on what it takes to build a business in the United States. Dan has started and built his own businesses. He’s run community development organizations that have worked to support the growth of other local businesses. And until January, he was CEO of the Eastern Market in Detroit, which is one of the last great public markets in the country and has seen a remarkable number of businesses start, thrive, and even go

en

18:11

Dashboard: Introducing America the Entrepreneurial

21 Hats Podcast ·

2025/06/16

This week, Victor Hwang tells us that his organization, Right to Start, has big plans for America’s upcoming 250th birthday. Spurred largely by the widespread sense that the American Dream has lost some of its luster, Victor and Right to Start are launching a campaign to turn our semiquincentennial into a celebration of America’s entrepreneurial roots and a push to remove the barriers that make it harder than it should be to start and build a business. One key focus: finding ways to make it easier

en

55:16

‘The General Purpose Agency Is Doomed’

21 Hats Podcast ·

2025/06/10

This week, in episode 250, we’re joined by special guest Alan Pentz, who recently stepped back from his government-contracting business to start the Owner Institute, which draws on lessons he learned the hard way to help business owners scale their businesses. In his new role, Alan has immersed himself in the world of generative AI, and he’s come to some intriguing conclusions, one of which is that AI will eliminate most B-to-B agencies—marketing agencies, public relations agencies, professional

en

18:34

Dashboard: Is the GOP Tax Bill Good for Business?

21 Hats Podcast ·

2025/06/09

On the one hand, Gene Marks tells us this week that the GOP tax bill that has passed the House and is being debated in the Senate contains a lot of elements that should cheer business owners. Specifically, the pass-through deduction would get extended and increased, the capital-equipment deduction would go back to being 100-percent deductible in the first year, and the research-and-development deduction would also go back to being fully deductible in the first year. On the other hand, Gene believes

en

59:17

‘Mom, I Am Not Taking the LSAT’

21 Hats Podcast ·

2025/06/03

This week, in Episode 249, we bring you a conversation recorded at our recent 21 Hats Live event in Ann Arbor, Michigan, with Ari Weinzweig, co-founder of one of America’s most influential small businesses. Starting 43 years ago with a highly successful college town delicatessen that they could have replicated all over the country (including for Disney), Ari and co-founder Paul Saginaw have instead built Zingerman’s Community of Businesses, a collection of 12 Ann Arbor-based, collaboratively run

en

29:28

Dashboard: The Best Kept Secret in Business Lending

21 Hats Podcast ·

2025/06/02

This week, Sahra Halpern, who is CEO of the Business Consortium Fund, talks about a type of lender that is not particularly well known or well understood even among business owners. The Business Consortium Fund is a CDFI, or community development financial institution. Traditionally, many CDFIs, including Halpern’s, have sought to serve underrepresented business owners who have struggled to get a traditional bank loan. In the current political climate, however, CDFIs are looking to reach a broader

en

38:54

How Big Do I Want My Business to Be?

21 Hats Podcast ·

2025/05/27

This week, in Episode 248, we bring you a taste of what we experienced at the recent 21 Hats Live event in Ann Arbor, where we did a deep dive into a challenge confronting Mars Chapman, owner of Casey’s New Orleans Snowballs, a snowcone business in Austin, Texas. Mars, who is 36, bought the business from his parents and also inherited from them a somewhat laidback approach to ownership. The business has been operating for 29 years, but it has generally run only eight months of the year, which has

en

26:39

Dashboard: Bringing AI into the Sales Process

21 Hats Podcast ·

2025/05/23

This week, Lance Tyson, founder of the Tyson Group sales consultancy, talks about how he’s using generative AI in his own business along with his suggestions for owners who are just getting started with AI. Among his suggestions: ask ChatGPT how best to use ChatGpt. Lance also talks about how salespeople can best navigate a business environment struggling with tariffs, uncertainty, rising prices, and talk of recession. One tip: don’t just accept an email rejection. Try to get them on the phone.

en

45:50

We Get Paid to Judge People

21 Hats Podcast ·

2025/05/20

This week, in Episode 247, we welcome a new regular, Kate Morgan, who joins the podcast along with Paul Downs and Jay Goltz. Kate is the CEO and founder of Boston Human Capital Partners, which provides recruiting and HR services, mostly to other small businesses. After a very difficult stretch caused by the pandemic, Kate’s business has been growing again – but Paul and Jay think she’s leaving money on the table. They think she needs to raise her prices. “I mean,” responds Kate, “we're growing in an

en

23:48

Dashboard: A Glimmer of Hope for Small Businesses

21 Hats Podcast ·

2025/05/19

This week, John Arensmeyer, our man in Washington, reports on what small business owners need and what they are likely to get from Republicans and Democrats. The issues -- tariffs, access to capital, taxes, health care -- are tricky, but John says there have been some recent examples of legislators coming together to support small businesses.

en

52:32

‘I’ll Tax Your Seat’

21 Hats Podcast ·

2025/05/13

This week, in Episode 246, we meet Ben Knepler, who, along with his True Places co-founder Nelson Warley, came up with an idea for an outdoor chair that they believe could be a game-changer. They liked the idea so much that they quit their corporate jobs, they raised money, they borrowed money—putting their own homes at risk—they fought through the pandemic, they found a manufacturer in China, they launched on Kickstarter, they found another manufacturer in Cambodia, and then they ran smack into the

en

27:37

Dashboard: They Should Have Fired Themselves

21 Hats Podcast ·

2025/05/12

This week, Gene Marks -- normally a fan of automating anything that can be automated — says it’s too soon to think about turning important tasks over to artificial intelligence bots, mostly because they’re still making too many mistakes. In fact, Gene cites a survey of business leaders who said they came to regret offloading employees in favor of AI. In many cases, those leaders wound up trying to re-hire their employees. Plus: Gene also talks about how businesses using AI can get into regulatory

en

51:02

Maybe Earnouts Aren’t as Bad as You Think

21 Hats Podcast ·

2025/05/06

This week, in Episode 245, a new regular, David Barnett, joins the podcast along with Jaci Russo and William Vanderbloemen. David, who has been a guest on the podcast before, helps people buy and sell businesses—but, as he explains, he’s not a business broker. He’s found a different business model. David, Jaci, and William discuss why it’s so hard to sell a business, what owners can do to make their businesses more attractive to buyers, and why it can be in everyone’s interest for sellers to accept

en

24:13

Dashboard: There’s Still a Talent Crisis for Small...

21 Hats Podcast ·

2025/05/05

This week, Rob Levin, co-founder and chairman of WorkBetterNow, talks about why he sees business owners—despite the uncertain economy—still struggling to fill key roles. He also discusses the importance of creating a culture by design, how owners can manage their profiles on Glassdoor, and what he thinks of Gen Z employees. Plus: Rob explains how he’s been infusing AI into all aspects of running his business.

en

526 results

Similar Podcasts

TaxTalent.com The Golden Rule Podcast

Adam Golden

TaxTalent.com Podcast

Tony Santiago

Handelsblatt Crime - spannende Streitfälle der deutschen Wirtschaft

Ina Karabasz, Solveig Gode, Sönke Iwersen

Deffner und Zschäpitz – Der Wirtschafts-Talk von WELT

WELT

Black Box - La scatola nera della finanza

Guido Brera e Gian Luca Comandini -...