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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

23:09

Dashboard: What Type of Entrepreneur Are You?

21 Hats Podcast ·

2022/09/12

How much control do you need? How much risk can you handle? This week, Ami Kassar, a small business finance expert, recalls feeling inadequate when he saw other entrepreneurs raising lots of money and going for broke (and sometimes getting there). He began to realize that there are different entrepreneurial personality types, and he’s developed a survey that can help you understand your own entrepreneurial instincts. The founder of MultiFunding also discusses how willing banks are to lend right now,

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45:47

We Have a Meeting With Costco!

21 Hats Podcast ·

2022/09/06

This week, in episode 122, Hans Schrei and Sarah Segal talk about what it takes to break into Costco. How do you get on their shelves? If you do get there, how do you make sure your product will fly off of those shelves? And if you succeed, will you have the financing you’ll need to ramp up production? Along the way, Sarah offers some tips on enlisting Costco influencers, and Hans explains the inner workings of Wunderkeks’ equity crowdfunding campaign, where you can invest as little as $150 and

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50:28

Replay: You Take a Stand

21 Hats Podcast ·

2022/08/30

This week, in part because Loren’s on vacation, we’re offering a replay of an episode we recorded more than two years ago. It was one of our early episodes, and it was recorded shortly after George Floyd was murdered. In the episode, Karen Clark Cole, William Vanderbloemen, and Dana White talked about how they viewed their responsibilities as business leaders at such a fraught moment. What, if anything, were they saying to their customers? What were they saying to their employees? It started as a

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49:23

Here’s My New Succession Plan: I Can’t Die

21 Hats Podcast ·

2022/08/23

This week, in episode 121, Shawn Busse, Jay Goltz, and Liz Picarazzi discuss their succession options and—if they could go back in time—what advice they would give their early-stage selves. Liz would tell herself to get some help with administrative tasks, Shawn would tell himself to find a mentor (although he’s not sure he would have listened to the advice), and Jay would tell himself that there’s an obvious solution to the chaos caused by fast growth. Plus: How Liz changed the narrative after

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22:46

Dashboard: The Tax Break No One’s Talking About

21 Hats Podcast ·

2022/08/22

This week, Gene Marks and Loren Feldman talk about the rise of “quiet quitting,” the new term for when employees contribute the bare minimum. They also discuss the phenomenon of bosses who come into the office to set a good example even as their employees phone it in from the beach. But most importantly, Gene points out what few others have noted, which is that the Inflation Reduction Act extends a huge tax break for business owners that was nearing expiration. And that’s just one of many aspects of

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48:53

Surviving Bad Clients and Bad Partners

21 Hats Podcast ·

2022/08/16

This week, in episode 120, Shawn Busse and Paul Downs talk about what they’ve learned from their worst client experiences. Shawn, for example, tells us that he’s come to think about taking on a client much the way he thinks about hiring an employee. And Paul stresses the importance of watching what he says about difficult clients to his employees, because he doesn’t want to encourage a cynical attitude. From bad clients, our conversation shifts to bad partnerships. Even though their own partnerships

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22:58

Dashboard: What the Inflation Reduction Act Means for...

21 Hats Podcast ·

2022/08/15

This week, John Arensmeyer, founder and CEO of Small Business Majority, an advocacy group for entrepreneurs and businesses, talks about what businesses can expect from the legislation coming out of Washington, D.C.—not just the climate, tax, and health care bill, but also the CHIPS and Science Act. In many instances, the benefits to business owners will come indirectly, he says, but they will come nonetheless.

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48:28

Trash, Rats, and Garbage Juice: A Case Study in PR

21 Hats Podcast ·

2022/08/09

This week, in episode 119, Liz Picarazzi tells Jay Goltz and Sarah Segal about her first brush with bad publicity. Liz’s debacle started with a negative post that appeared in a prominent local blog. It was about a Times Square pilot program for which her business, Citibin, is supplying trash bins. The problem? The bins were not being maintained properly, and there were photos to prove it. At the time we recorded this conversation, Liz was bracing for additional stories in both the New York Post and

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28:44

Dashboard: Why Gene Marks Hates Employees, Part 492

21 Hats Podcast ·

2022/08/08

This week, Gene talks about how he recently had a mild case of COVID but worked right through it, no problem, which got him to wondering why employees—in his view—do not seem to be similarly dedicated. In fact, Gene believes that employees are using “COVID hysteria” as a pretext to avoid work and catch up on their TV watching. Plus, Gene explains why he thinks Wawa, a chain of convenience stores, is a good model for his own business. And he tries to make sense of a recessionary economy that produced

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43:05

“I Think I’m Screwed”

21 Hats Podcast ·

2022/08/02

This week, in episode 118, Jay Goltz tells Shawn Busse and Karen Clark Cole about a dream he had recently. It was a dream, of all things, about this very podcast, and on it, someone—it was a guy—was talking about how his business was faring: “I think I’m screwed,” he says in Jay’s dream. But who was it? And why was he screwed? Jay woke up before those answers were revealed. So we did some interpreting on this week’s real podcast. Spoiler alert: It wasn’t that hard to interpret! Plus: Shawn explains

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20:29

Dashboard: Welcome to the Pre-Recession!

21 Hats Podcast ·

2022/08/01

This week, Gene Marks and Loren Feldman try to make sense of where the economy is headed and what it means for business owners. Plus, Gene explains why he thinks some business owners may be fooling themselves about whether their business is growing. He also talks about a CRM tool that Google is giving away for free, as well as what you need to know to start a business.

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47:37

Are There Enough Hours in Your Day?

21 Hats Podcast ·

2022/07/26

This week, in episode 117, Paul Downs, Sarah Segal, and Laura Zander discuss their daily routines, how those routines have been affected by the pandemic, whether they think they’re working too much or too little, and whether they would join a peer group where they would be exposed to owners who are working harder and, perhaps, having greater success. Plus: Laura places her bet on influencer marketing, Paul says his new marketing campaign has already paid off, and Sarah explains why none of her

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24:25

Dashboard: "I Killed"

21 Hats Podcast ·

2022/07/25

This week, Gene Marks reports back from a conference of funeral directors and debunks a silly survey that predicts a bleak future for small businesses. Plus: How the rules defining full-time employees and contractors could be changing, why some business owners are giving up on their CRM systems too soon, and how a relatively new law can help businesses save money administering retirement plans.

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44:05

Employees Still Have the Leverage

21 Hats Podcast ·

2022/07/19

This week, in episode 116, Jay Goltz, Liz Picarazzi, and William Vanderbloemen discuss how their businesses are holding up and whether they’ve gotten past the labor shortage (short answer: No). The conversation veers into a discussion of how to finance growth and what to do when your bank is unresponsive (find another one!). And then Liz explains her intense distaste for dealing with lawyers, accountants, and insurance agents and how she’s trying to cope with it. “Believe me,” responds Jay, “I

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25:56

Dashboard: Something Is Going to Happen

21 Hats Podcast ·

2022/07/18

Dashboard: Something Is Going to HappenThis week, Mel Gravely, CEO of Triversity Construction in Cincinnati, joins Dashboard to explain why—even though he has an extremely healthy backlog of work lined up for 2023—he’s more than a little concerned about where the economy is headed. He also talks about how the labor shortage in his industry started well before The Great Resignation and why he doesn’t see it ending any time soon. And then there’s the challenge of bidding for future contracts without

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43:00

How Would You Spend $10,000 a Month on Marketing?

21 Hats Podcast ·

2022/07/12

This week, in episode 115, Shawn Busse, Hans Schrei, and Sarah Segal explain what they would do if I gave them $10,000 a month to spend on marketing. As we all know, there’s a lot going on right now. No one’s entirely certain where the economy is headed, and no one’s entirely certain where digital marketing is headed. So it seemed like a good time to ask our regulars where they would place their bets if we offered them each an imaginary pot of money to promote their brands. Spoiler alert: Their

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25:31

Dashboard: Email or Text?

21 Hats Podcast ·

2022/07/11

This week, Gene Marks and Loren Feldman talk about the continued rise of text message marketing and how it can be integrated with your CRM system. They also discuss why Gene warns businesses off of Twitter—even though he’s a power user. Plus: How do you plan for a recession and a labor shortage at the same time? And is that $10 billion in SSBCI money flowing yet?

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40:28

Bonus Episode: Kurt Wilkin Hates Business Books. So...

21 Hats Podcast ·

2022/07/05

This week, in a special bonus episode, Kurt Wilkin talks about how he helped build several businesses, including most recently a recruiting business called HireBetter, and explains why he hates most business books. It has to do with the attention deficit issues he, like many entrepreneurs, tends to experience. So when he decided to write a business book of his own, he kept it short, and he structured it so that you can find the parts that are most relevant to you and skip the rest. It’s called

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46:03

Wunderkeks Has Two Daddies

21 Hats Podcast ·

2022/06/28

This week, in episode 114, we welcome another new panelist to the podcast, Hans Schrei, who is co-founder of Wunderkeks, an e-commerce bakery in Austin, Texas. Hans tells Jay Goltz and Liz Picarazzi why he and Luis Gramajo, his husband and co-founder, sold a business in Guatemala, immigrated here in 2019, and started a cookie business from scratch, going from selling at farmers’ markets their first year to doing more than $5 million in e-commerce last year. Hans also explains why he doesn’t think

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20:57

Dashboard: Keep Calm and Carry a Lot of Inventory!

21 Hats Podcast ·

2022/06/27

Gene Marks, our man in London (at least for this week), tells Loren Feldman that small businesses in the UK are doing quite well, thank you! Marks and Feldman also discuss how your CRM system can help you fight inflation, the good news about bankruptcy laws, how to increase profits without raising prices, and whether it’s now okay to swear in the office. Cheers!

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527 results

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