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. 3d ago

    Dashboard: The Numbers Said Don’t Do It. She Did It Anyway.

    This week, we talk to Leisa Peterson, who has spent much of her career thinking about money, risk, and the ways our emotions can interfere with financial decisions. So when Peterson and her family decided to launch The Gear Project, a peer-to-peer marketplace for used outdoor equipment, you might have expected her to proceed with unusual discipline and caution. And she did—right up to the point where the numbers started telling her that maybe they shouldn’t launch at all.As Peterson built out her financial projections, she kept discovering costs she hadn’t anticipated. The margins got thinner. The transaction volume required to make the business work got higher. She was ready to walk away. Her husband, daughter, and son-in-law wanted to keep going. So they did. Now, just weeks after launching, Peterson is deep in the part of entrepreneurship no spreadsheet can fully anticipate: fixing shipping problems, refunding incorrectly collected sales taxes, changing developers, manually approving thousands of listings, and discovering which of the warnings she heard before launch were right—and which weren’t.Along the way, she’s also confronting something more personal: whether a lifetime spent protecting herself from financial risk may have kept her from taking some risks worth taking. This episode is brought to you by Grasshopper Bank.

  2. 6d ago

    We Had to Become an AI-First Company

    This week, we welcome a new regular to the podcast team, Rob Levin, co-founder of WorkBetterNow. I first met Rob more than 20 years ago, when we were both experiencing the decline of print media. I was an editor at Inc. magazine, and Rob had started a regional publication for business owners called The New York Enterprise Report. “Starting a print publication in 2003 was not one of the smartest things I've done,” Rob says. But he learned from that experience. In 2018, Rob and a partner started WorkBetterNow, which helps American businesses hire Latin American talent. The business took off during the pandemic and has continued to grow rapidly. But in recent years, Rob began to see another disruption looming. If artificial intelligence can increasingly perform the kinds of tasks his company supplies people to do, what happens to WorkBetterNow? Rob tells Sarah Segal and Jaci Russo how seriously he took that question, what he decided his company needed to become, and how he’s trying to position WorkBetterNow for whatever comes next. We also talk about why referrals are no longer enough to sustain the company’s growth, what went wrong when Rob tried to build an outside sales force, and what he’s learned about managing remote workers. Plus, in another Beyond Small segment brought to you by Grasshopper Bank, Sarah, Jaci, and Rob compare how they manage the cash they keep on hand—and Jaci explains why she’s sleeping better since adopting Profit First earlier this year. Rob Levin’s book is called The New Talent Playbook. Get a free trial of the 21 Hats Morning Report. There is one seat left for the 21 Hats Succession Solutions Workshop.

  3. Oct 2

    Dashboard: Finance Your Business Without Taking on Debt or Investors

    Most business owners know the usual ways to finance a startup or acquisition: savings, investors, bank loans, SBA loans. But there’s another option that many owners have never considered—even though Jeremy Ames says his company, Guidant Financial, has helped arrange more than 35,000 of these transactions. It’s called ROBS financing—Rollovers for Business Startups—and it allows entrepreneurs to use money they’ve accumulated in retirement accounts to start or buy a business without taking a taxable distribution and, perhaps most notably, without taking out a loan. There’s no debt and no monthly loan payment. Instead, the owner’s retirement plan buys stock in the business.In this 21 Hats Dashboard, Ames explains how the structure works, why some owners use it to avoid debt while others combine it with SBA financing to buy a larger business, and what it costs to set up and maintain. He also addresses the tradeoffs: The money is no longer invested in stocks or mutual funds; it’s invested in your company, which means you’re betting some of your retirement savings on your ability to build a successful business.We discuss the questions owners should ask before making that bet, including how ROBS compares with conventional financing, what happens if the business fails, why the IRS has scrutinized these transactions, and why Ames believes anyone considering one should consult an independent adviser. The episode is brought to you by Grasshopper Bank.

  4. Sep 29

    Maybe AI Won’t Destroy My Business

    This week, Paul Downs, Jaci Russo, and Sarah Segal revisit a question that came up on the podcast more than a year ago: Is artificial intelligence going to doom professional service firms like Jaci’s branding agency and Sarah’s PR firm? So far, both Jaci and Sarah are feeling pretty good about their prospects. In fact, they’re seeing changes in the market that suggest AI may be helping rather than undermining their businesses. Paul, meanwhile, has encountered a different kind of AI mystery. For years, his custom conference table business has depended heavily on people finding him through Google. Recently, he discovered that his organic search traffic has fallen about 35 percent. That sounds alarming—except that his business is doing great. Paul says his tables are selling like “hotcakes,” and he’s backlogged into February. So what exactly is happening when traffic falls but sales keep growing? Plus: In our latest Beyond Small segment, sponsored by Grasshopper Bank, Paul, Jaci, and Sarah talk about the financial processes they still insist on doing manually—even when technology could probably do more of the work for them. In each case, part of the reason is that doing the work themselves gives them a view into their operations that they don’t want to lose. As Sarah puts it, while she already knows how to handle public relations, “I am learning how to be a business owner every day.” Show Notes: Here’s the episode where Alan Pentz predicted that professional service agencies are doomed. Get a free trial of the 21 Hats Morning Report. There are three seats left for the 21 Hats Succession Solutions Workshop.

  5. Sep 25

    Dashboard: Do You Care What Happens to Your Business After You Sell It?

    This week, Lou Mosca raises a question that business owners may not spend enough time thinking about before they sell the business: Once you’ve gotten the price you want, how much do you care what happens to the business? Lou, who owns the consulting firm American Management Services, has spent decades working with owner-operated businesses. More recently, he’s also been trying to work with private equity firms whose portfolio companies need help improving their performance. And that has given him an increasingly close look at what can happen when an owner sells to private equity.As Lou sees it, private equity can absolutely be the right exit for some owners. But he also thinks owners need to understand that getting a great price doesn’t necessarily mean they’ll be happy with what comes next. Lou shares some cautionary stories and offers practical advice for owners considering a PE offer—especially those who do care about what happens to their employees, their culture, and the business they built. The episode is brought to you by Grasshopper Bank.

  6. Sep 22

    Can an Owner Really Know What’s Going On?

    This week, Jay Goltz and William Vanderbloemen tackle a problem that business owners may associate with big companies: What happens when an employee becomes convinced that his or her manager is making bad decisions, but going through normal channels just isn’t working? Jay says he absolutely wants employees to speak up, even if that means going over a manager’s head. William agrees that there are times when an employee has to escalate a problem. But as the conversation unfolds, both acknowledge something that can be easy for an owner to underestimate: Speaking up can feel extraordinarily risky to employees. And how is that information going to surface then? And in our latest Beyond Small segment, Jay and William discuss what, if anything, another bank could offer that would persuade them to move their business—and why both have grown wary of what happens when smaller banks get swallowed by bigger banks. Plus: How should owners think about the forecast of a prominent economics group that a severe downturn is likely to hit in 2030? And William talks about how his wife’s cancer diagnosis has changed the way he thinks about time, work, and succession. As one of his older golf partners put it, life is like a roll of toilet paper: “It goes really fast at the end.” Show Notes: Read more about ITR Economics’ Great Depression forecast for 2030. Get a free trial of the 21 Hats Morning Report. Learn more about the 21 Hats Succession Solutions Workshop.

  7. Sep 18

    Dashboard: Are You Still the Best Person to Run Your Business?

    For a lot of business owners, there comes a point when the obvious choices seem to be: keep running the business or sell it. But Tighe Burke says there’s a third option that owners often overlook: keep the business, hire someone else to run it, and let that person take it places you may not be equipped—or inclined—to take it yourself. Burke, who runs the executive recruiting firm Srch, specializes in finding operators for founder-led businesses. He says one of the hardest things for entrepreneurs to accept is that someone else may actually be better at running their company than they are.In our conversation, he explains how owners can tell when it’s time to step aside, what it costs to hire a professional operator, why owners have to be prepared to give that operator real authority, and what tends to happen when they don’t. He also explains why, for an owner contemplating an exit, hiring the right CEO can sometimes be a better financial move than selling—allowing the owner to keep collecting profits, grow the company's value, and perhaps sell it later for considerably more. The episode is brought to you by Grasshopper Bank.

  8. Sep 15

    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?

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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
    574
  • Rating
    Clean
  • Copyright
    © Copyright 21 Hats
  • Show Website
    21 Hats Podcast

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