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. 1d ago

    You Just Lowered the Value of Your Business

    Earlier this year, Ted Wolf suggested that Paul Downs should take a serious look at how artificial intelligence might improve his custom woodworking business. Paul was skeptical—but he invited Ted and his team to come visit the shop and see for themselves. This week, Ted reports back. He came away impressed by the business Paul has built but also convinced that Paul has a problem: As Ted sees it, too much of what makes the company work still resides in Paul’s head. Ted believes AI could help capture some of that knowledge, improve everything from estimating to production, and, perhaps most important, prepare the company to run one day without Paul. Paul remains unconvinced. He agrees that AI will find its way into the business eventually, but he questions whether it can capture the judgment, experience, and nuance required to build one-of-a-kind products. His inclination is to let the next owners figure that out. “So Paul,” Ted responds, “if they’re going to have to deal with it, you just lowered the value of your company.” Which raises a question that goes well beyond AI: If you hope someday to sell or transfer your business, how much of what you know has to be captured before you leave? Plus: In our latest Beyond Small segment, sponsored by Grasshopper Bank, I ask Paul, Ted, and Lena McGuire what would happen if their businesses suddenly doubled. Would they be thrilled—or terrified? Could they handle the growth? And would they even want it? That leads to a discussion that comes up here fairly often: How big do you really want your business to be?

  2. 5d ago

    Dashboard: He Sold the Business. The Regrets Came Later

    Kevin Donnelly was 44 when an unsolicited offer set in motion the sale of the telecommunications company he had spent nearly 20 years building. The business had grown to more than 600 people in 38 cities and about $50 million in revenue, and Kevin says the deal itself worked out well for him financially. But that doesn’t mean he looks back on the experience without regret.What bothers him most is what happened to the people who helped him build the company. After the sale, employees started getting let go, and Kevin came to believe he should have done more—through bonuses, transition planning, or simply by thinking more carefully beforehand about his obligations to the people who had helped create the value he was selling. As he puts it, the way you treat those people can “come back to haunt you.”That experience, along with a brief post-sale detour into the restaurant business, eventually led Kevin to become an exit-planning advisor and to launch Inside Exits. His focus now is on owners who may not have an easy path to a conventional sale—often because of customer concentration, owner dependence, limited scale, or other issues that make a business less attractive to strategic buyers or private equity.His answer is not that every owner should pursue an ESOP or any other single structure. In fact, Kevin is explicitly agnostic. He talks about ESOPs, employee ownership trusts, worker co-ops, management buyouts, sales to existing employee-owned companies, and other creative arrangements. His goal is to help owners find a path that works financially, gives the business a chance to continue, takes care of the people who helped build it—and, ideally, leaves the owner with fewer reasons to look back with regret. The episode is brought to you by Grasshopper Bank.

  3. Sep 8

    She Thought She Was Building a Prospecting Tool for Herself

    This week, Jaci Russo, Liz Picarazzi, and David C. Barnett talk about something entrepreneurs are always being told they have to do: innovate. But how do you know which ideas are worth pursuing, how much time and money to put into them, and when an experiment starts to become something much bigger? Jaci Russo may be finding out. What started as a prospecting system she built for herself—with AI, verified data, and a simple CRM—has turned into ProspectDaily, a subscription product that attracted more than 100 customers before she even announced it. That has Jaci thinking the tool could do more than generate a little extra revenue. As AI makes it easier for clients to do more of their own marketing, she sees ProspectDaily deepening client relationships and ultimately changing the nature of her business. So far, she says, the hard costs of creating the tool amount to $185. (Try ProspectDaily for free.) Liz, meanwhile, is spending $10,000 this year testing whether old New York City trash cans and other recycled plastics can be turned into a new cladding material for Citibin. And she’s itching to spend another $30,000 on the equipment to manufacture the material once she determines whether customers actually want it. Both Liz and Jaci kept their projects quiet early on. As Liz explains, “I have so many ideas all the time. I didn't want there to be eye-rolling, ‘Oh, here's another of her things.’" Plus: In our latest Beyond Small segment, brought to you by Grasshopper Bank, the owners compare how closely they watch their numbers, which metrics matter most, and whether spending time on financials gets in the way of doing the work they really want to do—like coming up with new products.

  4. Sep 4

    Dashboard: The Competitive Advantage AI Can’t Copy

    When Nathan Miller started Rentec Direct almost 20 years ago, he wasn’t trying to disrupt an industry. He was a small landlord who couldn’t find affordable software that did what he needed, so he built his own. Other landlords started using it, then paying for it, and over time Rentec carved out a meaningful place in what became an increasingly crowded and well-funded market.Nathan says the company has managed to keep growing not by trying to match its venture-backed competitors dollar for dollar, but by sticking to a fairly simple formula: understand the customer, keep prices reasonable, provide unusually knowledgeable support, and build the kind of reputation that generates referrals. Today, Rentec has 16,000 property-management customers, 20 employees, and about $16 million in annual revenue.That formula is being tested again by artificial intelligence. AI has already wiped out much of the organic search traffic that once brought Rentec new customers, and Nathan acknowledges that it has also made it possible for almost anyone to build competing software. But he doesn’t sound especially worried. As he sees it, writing the code is only one small part of building a business. The harder things to reproduce are trust, reputation, industry knowledge, and customer service—which happen to be the things Rentec has been investing in all along.This week, Nathan explains how Rentec bootstrapped its way into a crowded market, why he continues to turn down investors, how AI is changing both his product development and his marketing, and what nearly 20 years of working with landlords has taught him about managing rental properties. The episode is brought to you by Grasshopper Bank.

  5. Sep 1

    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.

  6. Aug 28

    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.

  7. 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.

  8. 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.

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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
    567
  • Rating
    Explicit
  • Copyright
    © Copyright 21 Hats
  • Show Website
    21 Hats Podcast

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