21 Hats Podcast - podcast cover

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 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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Episodes

Bonus Episode: Seth Goldman Brews Another Ice Tea

This week, in a special bonus episode recorded right before Labor Day, Seth Goldman talks about getting the disappointing news that Honest Tea, the brand he built and sold to Coca Cola, was being discontinued—and how it took him about two weeks to decide to create another tea business, Just Ice Tea, to fill the shelf space that Coke was vacating. Along the way, Goldman talks about why it made sense to sell a mission-driven business to a soda company, what he wishes he had done differently in the...

Oct 07, 202235 min

Are You Hitting Your Numbers?

This week, in episode 126, Karen Clark Cole, Jay Goltz, and Sarah Segal discuss whether their businesses are meeting expectations and how that’s affecting their plans for next year. They also talk about how to handle an employee who doesn’t deliver, whether now is a good time to hire, and—in an answer to a listener question—how to make the transition from using contractors to hiring employees. And Karen explains why employee utilization—that is, what percentage of her people are actually billing...

Oct 04, 202241 min

Dashboard: I Like Recessions

This week, Loren Feldman speaks with Tracy Bech, who is CEO of Starboard Collectives and who specializes in helping business owners who don’t have a financial background (she understands: she was once one herself). Tracy talks about the two most important ratios for business owners to watch if they think we’re heading into a recession. And she also talks about why she actually likes recessions—or at least sees opportunities in them.

Oct 03, 202219 min

Raising Capital: 'It’s a Ticking Time Bomb'

This week, in episode 124, Shawn Busse, Liz Picarazzi, and Hans Schrei debate the merits and risks of taking outside capital. Clearly, it makes sense for some businesses. But what are the right circumstances? What are the alternatives? And what do you need to understand before going to the dance? For example, what are the dynamics of the entrepreneur-investor relationship? Are the entrepreneurs hoping the investors will bestow an opportunity upon them? Or is it actually the entrepreneurs who hav...

Sep 27, 202240 min

Dashboard: The (Commercial) Rent Is Too Damn High

This week, Gene Marks and Loren Feldman talk about what business owners can do to protect themselves in the current environment of rising rents and increased volatility. Plus: What explains the recent boom in startups? And will it last? And what the Fed’s rate hikes mean for businesses. Also: you can’t just set your website and forget it.

Sep 26, 202223 min

Should HR Advocate for the Business or the Employee?

This week, in episode 124, Karen Clark Cole, Jay Goltz, and Sarah Segal talk about hiring an HR person. First, how do you handle HR issues before you can afford HR people? Is software the answer? At what size does a business need a full-time person? Do you hire someone who has experience but who might not be used to getting his or her hands dirty? Or do you hire someone you can mold to fit the culture of your business? Jay, who likes to say the entrepreneur is often the worst person to interview...

Sep 20, 202243 min

Dashboard: Could California’s Fast Food Regulations Actually Work?

Signed by Governor Newsom on Labor Day, California’s new fast food law creates committees, among other things, to set an industry-wide minimum wage. The plan sparked lots of outrage, but Gene Marks explains why he thinks it’s worth a try. He also notes that it could well be coming to a state near you. Plus: Gene also makes the business case for paid parental leave while also raising some interesting questions, including this one: If you offer paid leave to new parents, is that fair to employees ...

Sep 19, 202223 min

Bonus Episode: Jason Fried Didn’t Mean to Blow Up Basecamp. But He’d Do It Again

This week, in a special bonus episode, Jason Fried talks about why things got crazy at software maker Basecamp and what it has meant for the business. As you may recall, in the spring of 2021, Fried, CEO and co-owner, issued a blog post edict eliminating a slew of benefits, shutting down a committee that had been attempting to address diversity issues, and barring discussion of all social or political issues on work forums. The email produced a backlash that culminated in a third of the company’...

Sep 16, 202246 min

Quiet Quitting: Another Gift Brought to You by Corporate America

This week, in episode 123 and in light of reports that half of the U.S. workforce has “quietly quit” their jobs, Shawn Busse, Paul Downs, and William Vanderbloemen talk about the latest rage: Is quiet quitting something new? Is it just a media creation? Have Shawn, Paul, and William experienced it in their businesses? And who’s to blame? Plus, the three owners explain how they hire for engagement and how they’ve changed their hiring processes in response to the pandemic and the labor shortage. F...

Sep 13, 202247 min

Dashboard: What Type of Entrepreneur Are You?

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 ...

Sep 12, 202223 min

We Have a Meeting With Costco!

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 ...

Sep 06, 202246 min

Replay: You Take a Stand

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 ...

Aug 30, 202250 min

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

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 ...

Aug 23, 202249 min

Dashboard: The Tax Break No One’s Talking About

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 aspect...

Aug 22, 202223 min

Surviving Bad Clients and Bad Partners

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 partners...

Aug 16, 202249 min

Dashboard: What the Inflation Reduction Act Means for Businesses

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.

Aug 15, 202223 min

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

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 ...

Aug 09, 202248 min

Dashboard: Why Gene Marks Hates Employees, Part 492

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 prod...

Aug 08, 202229 min

“I Think I’m Screwed”

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 expla...

Aug 02, 202243 min

Dashboard: Welcome to the Pre-Recession!

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.

Aug 01, 202220 min

Are There Enough Hours in Your Day?

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 e...

Jul 26, 202248 min

Dashboard: "I Killed"

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.

Jul 25, 202224 min

Employees Still Have the Leverage

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 h...

Jul 19, 202244 min

Dashboard: Something Is Going to Happen

Dashboard: Something Is Going to Happen This 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 with...

Jul 18, 202226 min

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

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 ...

Jul 12, 202243 min

Dashboard: Email or Text?

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?

Jul 11, 202226 min

Bonus Episode: Kurt Wilkin Hates Business Books. So He Wrote One

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 “...

Jul 05, 202240 min

Wunderkeks Has Two Daddies

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 thin...

Jun 28, 202246 min

Dashboard: Keep Calm and Carry a Lot of Inventory!

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!

Jun 27, 202221 min

Do Core Values Matter?

This week, in episode 113, Sarah Segal tells Shawn Busse and Paul Downs why she’s never articulated a set of core values for her business and why she’s thinking about doing it now. But she’s wondering whether establishing her values will really make a difference. Do employees care? Do clients care? Both Shawn and Paul say they do. In fact, Paul says his core values have been extremely helpful when it comes to recruiting. And Shawn says he thinks sharing values can be the best competitive advanta...

Jun 21, 202250 min
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