21 Hats Podcast

21 Hats
  • 5.0 (34)
  • Entrepreneurship
  • Updated Weekly

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.

  1. 2d ago

    We’re Growing. Now I Want to Make Money

    This week, Sarah Segal tells David C. Barnett and Jay Goltz that she has decided it’s time to pay more attention to something that can occasionally get lost amid the other demands of running a business: making money. Sarah’s agency is having a very good year, with revenue growing 40 to 50 percent. But she’s realized that growth alone isn’t enough. She wants to know exactly what it costs to hire each employee, what it costs to service each client, whether her fees are covering those costs—and what has to change if she’s going to hit a 20 percent profit margin. She’s also confronting something a lot of owners struggle with: how much to pay herself. For years, Sarah says, she’s been inclined to put the money back into the business rather than pay herself a market rate salary. Now she’s trying to do both—raise her own compensation while making the business more profitable. Along the way, Sarah, Dave, and Jay weigh in on how owners can fool themselves about profitability, why growing businesses eventually require real budgets, and what owners should actually expect from their banks. Is a bank merely a safe place to park your cash, or can you expect it to help you finance and build your business? Plus: When should a new business start paying its owner a salary? Dave argues that until a business can pay the owner for the work he or she is doing, it’s more of a hobby than a business. He also explains how entrepreneurs can get trapped in money-losing businesses—not necessarily because they still believe in the business, but because loans, leases, and personal guarantees can make shutting down even more expensive than continuing to operate. The episode is brought to you by Grasshopper Bank.

  2. 6d ago

    Dashboard: Stop Asking How to Use AI

    Business owners are being told constantly that they need to figure out how to use AI. Deb Weidenhamer thinks that may be the wrong place to start. Instead, she says, owners should look for the places where their businesses are already struggling: Where are you wasting time? Where are you losing money? Where are customers getting frustrated? Then ask whether AI can help.In this week’s Dashboard, Deb, author of AI for Real Companies: A Practical Guide to Smarter Systems and Stronger Profits, walks us through several examples of businesses that have done exactly that. A pizza shop uses AI to answer calls it had been missing during busy periods. A machine shop uses it to take on jobs that previously weren’t worth the time it took to quote them. And a real-estate team uses it to respond to leads that arrive while everyone is asleep. We also talk about the harder questions: whether AI really will eliminate jobs, why automating a bad process can make things worse, and why Deb believes the owner—not the IT person or some newly appointed “AI expert”—needs to take responsibility for deciding what gets automated and why. The encouraging part is that none of this necessarily requires becoming an AI expert. It requires understanding your business well enough to know what needs fixing. The episode is brought to you by Grasshopper Bank.

  3. Aug 25 ·  Bonus

    Best of: Selling My Business Nearly Broke Me

    This week, we revisit a conversation with Laura Zander that we first published last year, shortly after she and her husband Doug sold Jimmy Beans Wool, the business they had spent more than two decades building. Laura had been preparing to sell for years. She had kept the company’s books clean, built systems that could survive without her, and cultivated relationships with potential buyers. In other words, she had done many of the things owners are told they should do to prepare for an eventual exit. And still, when the right buyer finally came along, Laura says the process nearly broke her. There were 155 due diligence requests, endless rounds of legal negotiations, mountains of paperwork, and months when Laura and Doug were so consumed by the transaction that the business itself suffered. Meanwhile, life kept happening: a major website migration, tariffs, industry turmoil, family issues, and the constant fear that some unexpected development would cause the buyer to walk away. Even after the papers were signed, the work—and the stress—continued. Laura did ultimately get a deal she was happy with. But the more useful lesson may be what it took just to get there.

  4. Aug 21

    Dashboard: Is Staying Small Selfish?

    I met Lamar Tyler, founder of Traffic Sales & Profit, a couple of years ago at a Zone of Genius conference, where I interviewed him on the main stage. It quickly became clear that Lamar, who helps business owners grow, had a lot of smart, practical advice to offer, and I’ve been following him ever since. He recently posted something on LinkedIn that stopped me: “Staying small as a Black business owner is selfish.” Lamar, obviously, was speaking primarily to Black entrepreneurs, but his challenge applies more broadly. His argument is that owners who have the ability to build larger companies—and create more jobs, wealth, and opportunity—should not use “protecting their peace” or “staying lean” as an excuse to remain comfortable.I understand and appreciate what Lamar is trying to accomplish. But “selfish” is a heavy word. Isn’t an owner entitled to say, “I built this business to create a good life for myself and my family. Isn’t that enough?” Entrepreneurship is already hard. Most businesses fail. How much more risk should we encourage owners to take—and how much responsibility should they be expected to carry? That’s where Lamar and I begin this week’s Dashboard conversation. The episode is brought to you by Grasshopper Bank.

  5. Aug 18

    With My New Rent, I Will Clear Nothing

    This week, we start with a business owner who’s just learned his rent is jumping 40 percent and who sees three options: accept the new rent and essentially work for free, move and start over, or shut down and get a job. But when Paul Downs, Jay Goltz, and Ted Wolf do the math, they see another option—one the owner doesn’t seem to have considered. From there, the conversation turns to the choices owners make when the answer isn’t obvious. Paul, as it happens, is wrestling with two of those himself. Before the year began, he developed a plan to start selling his custom conference tables in the Middle East. Then the missiles started flying. Does he still spend $30,000 to see whether the opportunity is real, or should he put that money to work closer to home? And then there’s a potentially lucrative R&D tax credit that Paul thinks could be “a gift from heaven.” He believes his company qualifies for the credit, but he also wonders whether claiming it could invite unwanted scrutiny from the IRS. Different decisions, different stakes, but the same question: As Paul puts it, “What is your appetite for risk?”

  6. Aug 14

    Dashboard: It’s Not That Earnouts Are Bad. It’s That Bad Earnouts Are Bad

    Conventional wisdom about selling a business is pretty clear: If at all possible, get your money at closing. Don’t leave a big chunk of the purchase price dependent on the future performance of a business you no longer control. David C. Barnett, who helps people buy and sell businesses, has challenged that conventional wisdom, arguing that earnouts and other forms of deferred payment can sometimes help buyers and sellers get better deals done. Josh Patrick, who has owned and sold businesses himself and advised many other owners through transactions, is more skeptical. Which is why I was kind of hoping for a fight.Instead, Dave and Josh end up agreeing on quite a lot—including that once a seller decides to leave money in a deal, choosing the right buyer becomes every bit as important as negotiating the right price. Can the buyer actually run the business? What happens if things go wrong? What information should the seller continue to receive? And how can the deal be structured so that both sides have an incentive to make the transition work? So no, this isn’t quite the earnout cage match of my dreams. It’s actually far more insightful than that. The episode is brought to you by Grasshopper Bank.

  7. Aug 11

    My Succession Plan Just Moved to Montana

    Jaci Russo has had quite a summer. First, her husband and business partner, Michael, underwent an unexpected quadruple bypass. Fortunately, Michael's recovering well, and their branding agency passed an important test: With both founders largely out of commission, the team kept the business running and the clients happy. But that wasn't the only surprise Jaci had to deal with. For the past several years, she and Michael thought they knew exactly how they would eventually leave the business. They had a succession plan. They had a timetable. And they had already begun putting the pieces in place. Now, they're back to figuring it out. This week, Jaci tells Jay Goltz what happened and how she's thinking about her options now. It's a reminder that succession planning isn't just about choosing among selling to family, employees, investors, or some other buyer. It's also about recognizing that circumstances change, people change, and even a plan that once seemed settled can suddenly become anything but. Plus: We check in with Jay to see whether he's received the hundreds of thousands of dollars he's expecting in tariff refunds. And with Wayfair reporting improved sales, I ask Jay whether that's a sign the furniture business is finally recovering—or whether Wayfair's gains might actually be bad news for independent home stores like his. This episode is brought to you by Grasshopper Bank.

  8. Aug 7

    Dashboard: The Problem with Retainers (and Other Lessons for Solopreneurs)

    If you've built a successful business, you've likely been told the path to more success is obvious: hire employees, land bigger clients, lock in recurring revenue with retainers. But what if those aren't signs of progress? What if they're traps?This week, I talk with Pia Silva, author of Scale Solo, who argues that many of the traditional rules of entrepreneurship simply don't apply to solopreneurs. She explains why hiring too soon can derail a business, why retainers often aren't nearly as profitable as they appear, and why she'd rather do 10 $3,000 projects than one $30,000 engagement. Along the way, Pia also tells us why she and her husband named their branding agency Worstofalldesign, why she isn't afraid to tell clients, "You don't get a say," and how she's learned to sell clients on paying higher prices. This episode is brought to you by Grasshopper Bank.

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5
out of 5
34 Ratings

About

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.

Information

  • Creator
    21 Hats
  • Years Active
    2020 - 2026
  • Episodes
    563
  • Rating
    Explicit
  • Copyright
    © Copyright 21 Hats
  • Show Website
    21 Hats Podcast

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