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21 Hats

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.

Total 379 episodes

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8

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I’m Not Going to Shut the Doors

I’m Not Going to Shut the Doors

This week, we introduced a new member of the podcast team, Paul Downs, whose company, Paul Downs Cabinetmakers, makes custom conference tables. Paul wrote about how close his company came to failing in both The New York Times’ You’re the Boss blog and in his own book, "Boss Life: Surviving My Own Small Business." That was during the Great Recession. Unfortunately, Paul is once again finding it challenging to sell high-end conference tables during a crisis. “My game plan is to stick it out,” he told us in this episode. “I’m not going to shut the doors. And two years from now, I may be a smaller company, but I'm going to be around, and then we're going to ride this back up.”

40:5021/07/2020

Doomsday Fatigue

Doomsday Fatigue

In last week’s episode, we asked our panel of business owners this question: Would you be doing anything differently with your business if you knew for sure that a second shutdown order was coming? It seemed like a pretty straightforward question, but it triggered one of our guests, Jay Goltz, who called it a “stupid” question and encouraged the other panelists not to answer it. So this week, we decided to try again to see if we could better understand how Jay is processing these stressful times. And to some extent, we succeeded, and we did get a little further beneath the surface—although there’s still a part of Jay that seems to be in denial. But maybe that’s just what it takes to be a successful entrepreneur. As Jay likes to say, “There's a thin line between visionary and delusional, and I've certainly been on both sides of that.”

27:1107/07/2020

That’s a Stupid Question

That’s a Stupid Question

As the numbers of new coronavirus cases explode across the country, Karen Clark Cole, Jay Goltz, and Laura Zander talk about how they are trying to make plans for their businesses. The conversation heats up a bit as it becomes clear that one of our owners (Hi, Jay!) isn’t quite ready to confront the possibility that he might have to deal with another shutdown. By contrast, Laura tells us, “We're operating as if there is a shutdown. So, yeah, we're operating the same way we were two months ago.”

24:2330/06/2020

Do You Feel Shame Taking Money From the Government?

Do You Feel Shame Taking Money From the Government?

Jay Goltz, William Vanderbloemen, and Dana White—all of whom took Paycheck Protection Program loans—respond to an opinion piece that says “competent” business owners shouldn’t have had to go begging “shamelessly” for a government bailout, which got a particularly strong response from Jay: “I'm thinking of all of those entrepreneurs who are trying to run a business, trying to make happy customers—restaurants, hair salons trying to survive this whole thing, trying to take care of the emotional, the financial, and the physical needs… They're fighting a good fight, trying to stay in business so they can continue paying taxes, and he comes along and has to call us ‘shameless’ for taking money from the government.... Oh, we’re incompetent, because these people didn't have six months of savings stowed away?"

36:0723/06/2020

I’ve Never Raised My Prices

I’ve Never Raised My Prices

Karen Clark Cole, Jay Goltz, and Dana White discuss their pricing strategies and why raising prices can be such a challenge: Dana tells us she has often wondered, “If I raise my prices, is this the decision that's going to make me close my doors?” And Jay recalls a customer who came into his picture framing shop and told a sales consultant, “Wow, that's a lot more than the other place I've gone to.” “Really, why don't you go there?” “Well, they're out of business.” And that, Jay tells us, helps explain why there are far fewer frame shops than there used to be.

30:5016/06/2020

I’m Stressed

I’m Stressed

Karen Clark Cole, William Vanderbloemen, and especially Dana White have a painful, impassioned, uncomfortable conversation about trying to position their businesses and lead people in the aftermath of George Floyd’s murder and the ensuring protests. What do we tell customers? What do we tell employees? What do we tell black employees? Dana challenges us to take a stand—even if it’s uncomfortable—especially if it’s uncomfortable: “This is not about being comfortable. As business owners, you're either over there or you're over here.”

51:4109/06/2020

How Do You Handle the Fact That a Lot of People Don't Like You?

How Do You Handle the Fact That a Lot of People Don't Like You?

This week we focused on Laura’s struggle to get control of a Texas-based yarn supplier that she acquired late last year. She’s had issues with inventory, personnel, quality control, and then the general manager walked out, which has Laura feeling deflated knowing that some employees are talking about her and some just don’t like her: “I really struggle with that. Am I the only one who struggles with stuff like that?” Plus: Laura and Jay talk about seizing the opportunity when a competitor goes out of business.

36:5402/06/2020

Everything I Learn, I Have to Learn the Hard Way

Everything I Learn, I Have to Learn the Hard Way

Before the crisis hit, Jay, Dana, and William talked about what they thought the next recession might mean for their business and the benefits of starting a business during a recession: “What I've learned is, when things go bad and I lose $300,000 and I take out a second mortgage on my house, no one comes into my office and says, ‘Hey, boss, can I give you some money?’” Plus: Some making tough decisions on employee compensation.

53:3926/05/2020

You’re Not Human Anymore. You’re the Boss. Deal With It

You’re Not Human Anymore. You’re the Boss. Deal With It

In this week’s report from the front lines of the crisis, we talked about overcoming the fear of raising prices (during a pandemic!), deciding when is the time to tell employees they have to come back if they want their jobs, and finding opportunities amid the crisis disruption. But the focal point of the conversation was Dana White discussing her realization that she’s been more productive during the crisis, even with her hair salons shut down, than at any other time since she started her business seven years ago. “I have been emotionally drained for years,” she told us. “And because I've been emotionally drained, I have not grown my business.”

46:5019/05/2020

Dude, You’re Gonna Get on an Airplane?

Dude, You’re Gonna Get on an Airplane?

Karen, Jay, and Laura talk about dealing with questions they’ve never faced before: Is it safe to fly again? What do you do if you run out of inventory and can’t get more? How do you entice employees back into the office who’ve either been happy working from home or happy collecting enhanced unemployment? Do you offer hazard pay? And if so, how and when will you stop? “We're trying to stay in business, for God's sake,” says Jay Goltz. “We will have been shut down for two and a half months. And there's a point where I'm the only one who's gonna be losing money in this deal. At the end of the day, [my employees] are getting extra money from the government for unemployment. They're getting hazard pay. Everybody at the end of the year is going to have a banner year for income. And I'm going to lose hundreds and hundreds of thousands of dollars.”

39:1212/05/2020

My Employees Are Not Thrilled to Be Back at Work

My Employees Are Not Thrilled to Be Back at Work

Jay, Dana, and Laura talk about the process of reopening—the precautions, the risks, the consumers who might not show up, the dilemma of asking employees to accept less in pay than they were getting in unemployment, and the possibility of a second coronavirus wave that could bring a second shutdown: “I don't have the luxury of just saying, ‘Oh, I'll tell you what. Maybe we'll open in six weeks, eight weeks.’ I mean, there's some point where I'll be out of business.” Plus: Dana got her PPP and an EIDL.

45:3105/05/2020

Why Not Us?

Why Not Us?

Karen, Dana, and Laura share their experiences building businesses as women entrepreneurs: “It's like, ‘Well, you can tell me I can't do this, but it looks like I did.’” Plus: Has the legalization of recreational cannabis had an impact on your business?

51:2728/04/2020

Three Owners. Two Loans. One Emotional Conversation

Three Owners. Two Loans. One Emotional Conversation

Karen, William, and Dana talk about why some businesses got the Paycheck Protection Program loans and why some didn’t: “The independent grocers. The hair salons. The small restaurants. They didn't get the money,” says Dana. “I have a staff who are single mothers, single black mothers, who are hard-working and who didn't have the foundation to go to college and are doing what they can. I'm up every night trying to help them, and I need help helping them. And I'm not getting it.”

44:4621/04/2020

The Money’s in the Bank

The Money’s in the Bank

Jay, William, and Laura talk about the status of their CARES Act loans, and to everyone’s surprise (including his own), William reveals not only that his Paycheck Protection Program loan has been approved, but he’s already got the cash. Was it divine intervention? Plus: Jay offers up a stress test for businesses in crisis—five ways to assess whether your company is positioned to survive.

41:5214/04/2020

Warrior Mode

Warrior Mode

Jay, William, and Dana talk about their prospects for landing a Paycheck Protection Program loan, what they think business will be like when shelter-at-home ends, and why they decided to lay off people even though they expect to get forgivable loans: “The bottom line: we cut 40 percent of our payroll yesterday. My decision was, I would rather cut deeper, fewer times. So I'm going to do this once.” Plus: the daily routines of business owners stuck at home.

35:5907/04/2020

My Employees Are Freaking Out

My Employees Are Freaking Out

William, Dana, and Laura and their businesses are having very different coronavirus experiences. While Dana and William are expecting little in the way of revenue, Laura’s online yarn business is thriving. But they’re all facing challenges in managing their employees: “It's been amazing to see just how hard folks are working. Are they concerned about a layoff? I'm sure they are. I would be too.” Plus: finding ways to stay connected to customers even while the business is closed.

38:2131/03/2020

Where Can I Save Some Cash?

Where Can I Save Some Cash?

Karen, Jay, and Laura talk about painful layoffs, maintaining morale, and hunkering down during COVID-19: “We've been having a meeting for the last two or three days about, ‘Okay, we have X number of dollars in inventory. Can we pull a couple hundred thousand dollars out of inventory in case we end up being cash flow negative for the next two months?’” Plus: finding ways to help other struggling businesses and looking for opportunities to emerge from this stronger.

49:2424/03/2020

I Ain’t Going Down

I Ain’t Going Down

Karen, Jay, and Dana talk about the contingency plans they’re making as we head into the health and economic crises presented by COVID-19. Can they keep paying hourly workers? Can they keep their locations open? Can they find the resolve to hang on no matter where this goes? “You're gonna get through this. You're gonna do what you need to do. If you need to close the one salon, so be it. And you're going to come out of this whole thing because you're smart, and you're ambitious, and you're responsible, and people like you. You're gonna get through this.” Plus: is now the time to join a business peer group?

53:1417/03/2020

Maybe This Isn’t the Right Job for You

Maybe This Isn’t the Right Job for You

Nobody goes into business because they think they're going to be really good at firing people. When you read books or magazine profiles of business leaders, you rarely hear anyone say, “You know, the one thing I've really mastered is knowing when and how to fire people.” And yet it’s something that every entrepreneur has to deal with. Even at the most successful businesses, some employees are not going to make it. In this episode, regulars Karen, Jay, and Dana answer the question: how many people have you had to fire or lay off? Plus: What do you do when you find you have venture-backed competition?

43:5110/03/2020

Special Episode, Part 2: We Want to Talk to You About the Bread

Special Episode, Part 2: We Want to Talk to You About the Bread

In Part 2 of our special taping in front of a live audience at Blink UX’s headquarters in Seattle, Brian Canlis talks about how he and his brother took over the family restaurant and what happened when they decided to modernize its operation: “We did lose 10,000 guests that year. And we lost money for the first time as a company ever that year. And we got three negative reviews in the paper. And we were averaging about a dozen complaint letters a week about how much they thought Mark and I were destroying a family legacy. That was a low moment.” Regulars Karen Clark Cole, Jay Goltz, Dana White, and Laura Zander join the conversation as well. Plus: how Canlis gets employees to work harder for less money.

01:01:4803/03/2020

Mini Episode: The 21 Hats Business Owners Make Coronavirus Contingency Plans

Mini Episode: The 21 Hats Business Owners Make Coronavirus Contingency Plans

In a quick update, Karen, Jay, and Dana talk about how the coronavirus pandemic has already affected their businesses and how they are planning for the future.

08:1202/03/2020

Special Episode, Part 1: All You Have to Do Is Be Better

Special Episode, Part 1: All You Have to Do Is Be Better

In this special taping in front of a live audience at Blink UX’s headquarters in Seattle, Karen, Jay, Dana, and Laura talk about the risks of fast growth and why they haven’t taken investment capital. “I was so focused on growing that I kind of blew it up. I blew the whole business up by hiring people who we weren't ready to hire for. We were probably doing $5, $6, $7 million dollars in sales. I didn't need a $90,000 a year social media person 10 years ago. I just didn't, but I listened to what other people were telling me.” Plus: Dealing with competition.

44:2325/02/2020

We’re at the Edge Right Now

We’re at the Edge Right Now

Karen, William, and Laura discuss taking investment capital, dealing with stress, and why Karen’s going on sabbatical: “I just thought, ‘Okay, okay, I'll go.’ Then of course, I'm worried, like, ‘What if everything goes better without me?’” Plus: how are you managing health insurance costs?

54:4818/02/2020

Does Culture Really Eat Strategy for Lunch?

Does Culture Really Eat Strategy for Lunch?

Jay, William, and Laura discuss whether a great culture produces a successful business or whether a successful business produces a great culture. Do you think of your employees as family? Do you have anyone working for you whom, if you had it to do over, you wouldn’t hire? Plus: do you manage your Glassdoor page?

34:4911/02/2020

What Do I Have to Lose, Right?

What Do I Have to Lose, Right?

Jay, Dana, and Laura talk about risking it all, figuring out digital marketing, and connecting with your target audience: “Right now, my market is predominantly African American, but we have a lot of redheads. We have a lot of women of Indian and Middle Eastern descent.” Plus: how do you know if franchising makes sense for your business?

45:5904/02/2020

I’m Trying to Survive in Retail

I’m Trying to Survive in Retail

Jay, Karen, and Laura talk about competing on the internet, buying a supplier, and whether to take venture capital: “Who needs to answer to somebody if you don't have to?” Plus: after the Domino’s decision, what happens if your website isn’t disability compliant?

36:3228/01/2020

Special Episode: He Patted My Hand and Told Me I Didn’t Know Anything About Business

Special Episode: He Patted My Hand and Told Me I Didn’t Know Anything About Business

Loren and Karen talk with four of EY’s Entrepreneurial Winning Women about opening the books, bootstrapping a tech company, selling a business for more than $100 million, competing with Amazon, hiring hard-to-get talent, and pitching investors: “I've always said, ‘I'd rather be 75 percent of a watermelon than 100 percent of a grape.’” Plus: how much of your life do you have to sacrifice to be successful?

01:29:2808/01/2020

At Vanderbloemen Search, Everyone Blogs. Everyone? Everyone.

At Vanderbloemen Search, Everyone Blogs. Everyone? Everyone.

Jay, Karen, and William talk about pricing, custom manufacturing, and content marketing: “There have been people who would have been very good at a job, but they aren't willing to or able to put together content, and that just doesn't work for us.” Plus: the SEO value of an unusual last name.

44:1208/01/2020

Is Your Business Making as Much Money as You Think It Should?

Is Your Business Making as Much Money as You Think It Should?

Karen, William, and Laura talk about being a bad CFO, dealing with a disappointing profit margin, and the true price of growth: “I think our commitment to being cash-based and debt-free has been more important to me than the big number at the end of the year.” Plus: hiring employees vs. hiring contractors.

36:5507/01/2020