21 Hats Podcast

21 Hats
  • 5.0 (33)
  • 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. 23H AGO

    Hot Seat: Three Owners, No Easy Answers

    Sometimes the best conversations start with a simple question—and then another, and another. This week, we put Kate Morgan, Jaci Russo, and Ted Wolf in the hot seat and fire away: Are you hiring? Are you finding impressive job candidates? What was the worst job you ever had—and did you learn anything from it? Have you bought crypto? If you had $10,000 a month to spend on marketing, where would it go? Should a marketing agency ever turn its marketing over to another marketing agency? What’s holding you back? What’s the simplest thing you’ve never quite figured out how to do? None of these are trick questions, but they don’t necessarily have easy answers. Kate admits she’s never opened her accounting software. Jaci says one of the best things that ever happened to her was getting fired. Ted recounts losing 40 percent of his company’s revenue in a single weekend. Running a business means living with trade-offs, uncertainty, and the occasional punch to the gut. As Jaci reminds us, it usually works out—one way or another. But that doesn’t mean the answers are simple when you’re in the middle of it.

    53 min

  2. 4D AGO

    Dashboard: Where Do You Turn When You’re Stuck?

    Kelly Berry’s introduction to small-business ownership came at a moment when most new parents are focused on something else entirely. She had just come home from the hospital after giving birth when her husband handed her a personal guarantee to sign. He had quit his job to start a business.“So if this fails,” she said, “you’ll be unemployed and we’ll be homeless?”“Yep,” he replied.That moment made the risks of entrepreneurship very real—and it helped set Kelly on the path she’s been on ever since. She went on to earn her MBA, work with economic-development organizations, and eventually launch her own business running peer groups for business owners. Her focus has always been the same: helping owners navigate the challenges they face—together.In this week’s Dashboard, Kelly shares what she’s seeing on the front lines of small business, why peer groups can be so powerful, and how she’s working to bring that support to owners in rural communities who may not have access to in-person groups. She also talks about what it takes to build her own business along the way. And if you’d like to explore whether a peer group might be right for you, you can start with a short quiz she’s created.

    33 min

  3. FEB 10

    We’re Trying to Outgrow the Valley of Death

    Almost every growing business experiences a moment when success starts creating as many problems as it solves. Sales are up. The team is bigger. The product line is broader. And suddenly, the systems that got you here start to break. That’s where Liz Picarazzi finds herself right now. “We’re in the valley of death,” she says. “And we really need help.” Liz’s company, Citibin, made the most recent Inc. 5000 list, but Citibin has also hit that dangerous in-between stage—too big to run on improvisation, too small to have put in place all of the processes it needs. So Liz is trying to grow her way out of the valley. She’s hired a marketing agency. A growth consultant. And two AI advisors. She’s testing new domestic fabricators. And she’s rebuilding her website from the ground up—because right now, it’s generating no more than 10 percent of sales, and she knows it can do better. The site hasn’t kept up with her expanding product line, and it isn’t even optimized for search engine discovery, let alone for generative AI discovery. Talking it through with Paul Downs and Jaci Russo, Liz confronts some uncomfortable questions: How much copy is “enough” for AI? How transparent should pricing be—especially for a premium product whose prices could scare away some customers? And who has a better feel for the company’s story—the owner who’s lived it or the agency that has more experience helping businesses connect with customers? Not surprisingly, Liz and Jaci have different instincts on that one. What follows is a candid look at what it takes to rebuild a growing business at the dawn of a new era.

    47 min

  4. FEB 6

    Dashboard: Why Chasing Growth So Often Backfires

    For most business owners, growth is the goal. More customers. More revenue. Bigger numbers. Bigger opportunities. And often, more pressure. But what if the way most of us think about growth is actually setting us up for trouble? Economist Gary Kunkle has spent years studying what really drives business performance. Not in headlines or case studies—but in large sets of real-world data. And what he’s found is that fast, aggressive growth often creates risks that owners don’t see until it’s too late.One reason is this: His research indicates that in most companies, about 20 percent of customers generate almost all of the profit. Most of the rest barely break even. And a surprising number quietly lose money. So when you chase growth, you’re often just adding more of the wrong customers—more complexity, more strain, more work, and less margin. In this conversation, Gary explains why steady, disciplined growth tends to outperform flashy expansion—and how understanding your own numbers can help you avoid the traps that derail so many otherwise strong businesses. Want to learn more? You can go to Gary’s website or email him directly: gmkunkle@yahoo.com.

    31 min

  5. FEB 3

    I Can Help with AI. Do Owners Want Help?

    Alan Pentz is convinced a wave of disruption is about to crash into small businesses—and he’s doing everything he can to warn owners before it hits. He’s writing, teaching, consulting, waving the red flag. He’s just not sure anyone is ready to listen. “I don’t know if you’ve seen Don’t Look Up,” he says, “but it’s kind of like that. The asteroid’s coming—and everyone’s still walking around like it’s normal.” In our latest 21 Hats Brainstorm, Alan put his own future on the table. He asked a panel of owners to help him answer a hard question: Do business owners actually want help adopting AI? And if they do, what kind of help will they pay for? Is there a real, scalable business here—or just a lot of interest and polite nodding? And there’s one more twist: Alan already owns a successful consulting firm. So he also has to decide whether this opportunity is worth jumping back into the startup grind to build another service-heavy business from scratch. This 21 Hats Brainstorm is brought to you by New Bridge Studios, which helps companies, creators, and causes connect their stories to the bottom line.

    51 min

  6. JAN 30

    Dashboard: One Industry Just Got an AI Playbook for Running a Business

    Ryan Markewich knows the landscaping business from the inside. He built and sold a successful landscaping company in British Columbia, then spent years coaching owners of all kinds of businesses through the Great Game of Business—helping them understand their numbers, their people, and their decisions. Now he’s a certified advisor with an AI-powered platform called LeanScaper It’s only been around for about a year, and it’s designed specifically for landscaping businesses but it’s growing quickly because it offers a practical, step-by-step playbook that helps owners think through pricing, staffing, cash flow, and growth decisions, using AI to guide—not replace—their judgment. This week on Dashboard, Ryan walks us through what happens when one industry gets an AI playbook for running a business—and why landscaping may be an early glimpse of what’s coming for a lot of small business owners.

    42 min

  7. JAN 27

    I Expect to Grow This Year. Should I Hire Now?

    Things are suddenly moving fast at Sarah Segal’s San Francisco PR firm. Several new clients look likely to sign on, and for the first time in a while, growth feels real. Which leaves Sarah with a familiar, nerve-racking question: Do you hire before the work arrives—or wait until the revenue is actually in the door? If she hires now, she may have to cut her own pay until the new business materializes. And there’s no guarantee it will. She still remembers the last downturn, when she had to lay off people she cared about—and she’s determined not to repeat that experience. But if she waits and the clients do sign, she risks something else: overloading her existing team, burning people out, and falling behind before she can recruit and train new hires. The pressure is even higher because Sarah has already set an aggressive revenue goal for 2026. Plus: Jaci Russo explains why she’s adopted a different approach to planning and budgeting. Instead of guessing how much she can afford to spend, Jaci is changing the order of the math. After revisiting Mike Michalowicz’s Profit First—prompted by a story highlighted in the 21 Hats Morning Report—she’s begun setting profit targets first and forcing every other decision, including hiring, to fit around them. It’s only been a few weeks, but Jaci says the shift is already changing how she thinks about risk, growth, and what she can actually afford.

    46 min

  8. JAN 23

    Dashboard: A Grand Experiment in Buying and Building Small Businesses

    Over the past six years, Teamshares has quietly been running an ambitious experiment in small-business ownership. The company has bought some 90 businesses—promising never to sell them—and then converted those companies to employee ownership. Even amid the uncertainty of 2025, those businesses generated more than $400 million in revenue and about $60 million in profit, with a surprisingly low failure rate and unusually high employee retention. This week, Michael Brown, co-founder and CEO of Teamshares, returns to the podcast at a pivotal moment. Teamshares is preparing to go public—a move that raises obvious questions for a company built around long-term ownership and patient capital. We talk about what Teamshares has learned about buying businesses from aging owners, what employee ownership really changes inside a company, and what is likely to happen when an experiment like this collides with the public markets.

    49 min
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5
out of 5
33 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
    508
  • Rating
    Clean
  • Copyright
    © Copyright 21 Hats
  • Show Website
    21 Hats Podcast

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