21 Hats Podcast

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21 Hats
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Entrepreneurship Business News Business News
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495 - 825 listeners Neutral 5.0 rating 33 reviews 422 episodes USA
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30s Ad: $19 - $23 60s Ad: $22 - $26 CPM Category: Business
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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.

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Recent Hosts, Guests & Topics

Here's a quick summary of the last 5 episodes on 21 Hats Podcast.

Hosts

Jess

Previous Guests

Jay Goltz
Jay Goltz is a successful entrepreneur and business owner known for his expertise in managing small businesses. He has a background in retail and has been involved in various ventures, including a framing business and a home furnishings store. Goltz is also a writer and speaker, sharing insights on business management and the challenges faced by small business owners.
Lena McGuire
Lena McGuire is a business consultant and coach specializing in helping small business owners improve their operations and systems. With a focus on efficiency and growth, she works with clients to streamline processes and avoid common pitfalls in business management. McGuire is known for her practical advice and hands-on approach to consulting.
Gene Marks
Gene Marks is a small business owner, author, and speaker who provides insights on business management and strategy. He is known for his expertise in navigating the complexities of small business operations, particularly in the context of economic challenges such as trade wars and tariffs. Gene frequently contributes to various publications and is a sought-after speaker for his practical advice on how businesses can adapt and thrive in changing market conditions.
Liz Picarazzi
Liz Picarazzi is a business owner known for her work in manufacturing trash enclosures. She has faced challenges related to tariffs and the economic viability of manufacturing in the U.S. Liz has actively sought ways to produce her products domestically but has found it difficult due to cost factors. She is also an advocate for women entrepreneurs, having surpassed a million dollars in annual revenue.
Shawn Busse
Shawn Busse is a business owner and entrepreneur who participates in discussions about small business challenges. He is known for his insights into the struggles faced by business owners, particularly in relation to economic policies and their impact on small businesses.
Jaci Russo
Jaci Russo is a marketing expert and business consultant who specializes in helping small businesses grow through effective branding and marketing strategies. With a background in communications and a passion for entrepreneurship, she provides valuable insights into the marketing challenges faced by business owners.
John Arensmeyer
John Arensmeyer is the founder and CEO of Small Business Majority, an organization that advocates for the needs and interests of small business owners. With a background in public policy and entrepreneurship, John has dedicated his career to supporting small businesses and ensuring their voices are heard in the political arena. He has been instrumental in addressing issues such as access to capital, healthcare, and the impact of government policies on small businesses.
Paul Downs
Paul Downs is a small business owner known for his candid discussions about the challenges faced by entrepreneurs. He has experience in managing workforce dynamics and financial planning, particularly in times of economic downturn. His insights into operational efficiency and financial management have made him a valuable voice in the small business community.
Sarah Segal
Sarah Segal is a business strategist and consultant with a focus on operational efficiency and growth strategies for small businesses. She has extensive experience in advising entrepreneurs on navigating the complexities of running a business, particularly in challenging economic climates.

Topics Discussed

bad hiring unemployment insurance rehiring business systems employee expenses tariffs trade war free-trade zones raising prices alternative suppliers China tariff bill manufacturing business owners women entrepreneurs revenue small business crisis President Trump's tariffs support infrastructure budget cuts survival strategies layoffs workforce reduction financial struggles digital marketing sales tax overpayment

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Episodes

Here's the recent few episodes on 21 Hats Podcast.

0:00 39:24

The Hidden Cost of Bad Hiring

Guests
Jay Goltz Lena McGuire
Keywords
bad hiring unemployment insurance rehiring business systems employee expenses
This week, in Episode 242, Jay Goltz and Lena McGuire talk about an expense a lot of business owners may not even realize they’re paying. When former employees collect unemployment, they get a check from the government, but then their former employer gets docked. It can add up to real money, and that’s likely to become a bigger issue if the economy deteriorates. Of course, as Jay and Lena discuss, one way to keep your unemployment insurance as low as possible is to do a better job hiring. Jay and Lena also talk about whether it ever makes sense to rehire someone you’ve had to fire. Plus: With Lena’s clients and potential clients putting on the brakes, she’s using this slow period as an opportunity to improve her systems. She’s hoping to avoid a mistake she made last time when she built a business that she was unable to sell.
0:00 25:52

Dashboard: Mitigating the Impact of the Tariffs

Hosts
Jess
Guests
Gene Marks
Keywords
tariffs trade war free-trade zones raising prices alternative suppliers China
This week, Gene Marks offers some suggestions for how businesses can survive President Trump’s trade war. Those suggestions include exploring free-trade zones, raising prices strategically, scouring the world for alternative suppliers, and getting out of China. Despite all of the disruption and upheaval, Gene continues to believe that the long-term gain will be worth the short-term pain.
0:00 53:06

The Tariff Bill Arrives

Guests
Liz Picarazzi Shawn Busse Jaci Russo
Keywords
tariff bill manufacturing China business owners women entrepreneurs revenue
This week, in a conversation recorded on March 27—shortly before Liberation Day, the day Donald Trump announced his so-called reciprocal tariffs—Liz Picarazzi told Shawn Busse and Jaci Russo what it was like to get her most recent tariff bill for a shipment of trash enclosures from China. “I knew what it was going to be, because I had calculated it,” she says, “but to actually see it on paper was terrifying.” And of course it’s only going to get worse now. In our conversation, we discuss a couple of points that bear emphasis: One, Liz tried everything she could think of to find a way to manufacture her products in the U.S. It hasn’t been economically viable in the past, and it’s unlikely to become viable any time soon. And two, Liz wonders—if these tariffs really are intended to bring manufacturing back to the U.S.—why isn’t some of the tariff money being directed toward supporting that transition? Plus: it’s been widely reported that only a tiny percentage of women business owners surpass a million dollars in annual revenue. As it happens, Jaci and Liz have both done it, but why is it so rare?
0:00 23:16

Dashboard: A Fight for Survival

Hosts
Jess
Guests
John Arensmeyer
Keywords
small business crisis President Trump's tariffs support infrastructure budget cuts survival strategies
This week, John Arensmeyer, founder and CEO of Small Business Majority, talks about the unprecedented crisis confronting small businesses. At the same time their business models are being upended by President Trump’s tariffs, business owners are also watching their support infrastructure get decimated by budget cuts. John talks about what owners can do to hunker down, to survive, and to make sure their voices are heard.
0:00 51:02

‘At 5 O’Clock, I’m Going to Send Everybody an Email’

Guests
Paul Downs Jaci Russo Sarah Segal
Keywords
layoffs workforce reduction financial struggles digital marketing sales tax overpayment
This week, in episode 240, Paul Downs tells Jaci Russo and Sarah Segal about laying off a third of his workforce. “Here's the problem in a nutshell,” he says. “Last year, January to March, we sold $1.356 million. This year, January to March: $680,000. March is on track to be the worst month I've had since I started taking records.” Paul also tells the owners that he used to have a rainy-day fund for such occasions, but he used it to renovate his house. He does think the layoffs and other cash savings have put him in a strong enough position to hang in there until business picks up. “We’re getting calls,” he says, “we’re just not getting orders.” He’s also trying out a digital marketing service that can identify and contact anyone who spends even just a few seconds on his website. Plus: Paul tells us that sometimes, when forced to lay off people, you learn things about your operation that you might not otherwise have known—like that you’ve been overpaying your sales tax by at least $30,000 a year for quite some time. 

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5.0 rating 33 reviews

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5.0 ratings 31 reviews

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