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

    Why Do You Pay What You Pay?

    The new pay transparency laws were designed to help job applicants and narrow pay disparities. But they've also had an unintended consequence: Employees now have far more information about what other people are making—and that can raise some uncomfortable questions for business owners. How do you decide what a job is worth? How much should you pay compared to the market? How much should employees know about what their co-workers earn? This week, Jay Goltz, Jennifer Kerhin, and Ted Wolf compare notes on compensation.  Jennifer explains how her philosophy has evolved from offering below-market pay and maximum flexibility to providing competitive salaries, benefits, and career paths. Jay discusses the challenges of determining what employees are truly worth—and why a bad bonus plan can be worse than no bonus plan at all. Ted makes the case for paying above market—not because he wants superstars, but because he believes well-paid employees become more committed, more flexible, and ultimately, more productive. Along the way, they discuss paying for health insurance, contractors versus employees, hiring mistakes, and the sometimes overlooked reality that while employees crave stability, business owners are the ones taking the financial risks. The result is a candid conversation about one of the hardest questions business owners face: What is the right way to compensate the people who help build your company? Plus: How concerned would you be if your employees found out how much money you, as the owner, are taking out of the business?

    48 min

  2. 5d ago

    Dashboard: A Compensation Plan Becomes an Exit Plan

    A health scare in 2015 prompted Julia Beardwood to confront a question many business owners prefer to postpone: What happens when it's time to leave the business? Over the next several years, the founder of the New York City branding agency Beardwood explored a range of possibilities, including selling to an ESOP and pursuing a strategic acquisition. But when the time came, the solution turned out to be much closer to home. Years earlier, Julia had implemented a compensation strategy that gave key employees a meaningful stake in the company's success. What began as a way to motivate and retain talent ultimately created a pathway for ownership transition.

    39 min

  3. Jun 16

    Maybe EOS Will Solve Our Problem

    The promise is seductive: Implement the right operating system and your frustrations disappear. Your employees become more accountable. Communication improves. Growth follows. Your business finally runs the way you always hoped it would. That's the promise behind EOS, the Entrepreneurial Operating System popularized by Gino Wickman's book Traction. Plenty of business owners swear by it. Plenty have spent tens of thousands of dollars hiring EOS implementers to help put it in place. But does it work? This week, we’re republishing one of our favorite conversations, one in which Shawn Busse, Paul Downs, and Laura Zander compare notes on their own experiences with EOS. Laura hired an implementer and spent years trying to make the system work. Paul took a more selective, do-it-yourself approach. Shawn has watched EOS play out inside numerous client companies. What emerges is a much more nuanced picture than the one promised in the book. The three owners discuss when EOS can be genuinely valuable, when it's the wrong tool for the job, and why no operating system can compensate for having the wrong people in key roles. As Laura puts it, EOS can be incredibly helpful "for people like me 10 years ago, who just don't know what they're doing." The question is whether that's enough to justify the investment.

    53 min

  4. Jun 12

    Dashboard: Helping Creatives with the Business of Art

    For years, Kim Robinson worked on the brand side, helping major companies connect with artists and creatives. Eventually, he decided he’d rather be working for the artists themselves. So he launched 3pts, a company that helps creatives handle the business side of their careers—everything from pricing and marketing to partnerships and strategy—so they can spend more time focused on the work they love.The first challenge, Kim says, is convincing artists that thinking about money and business doesn’t somehow compromise their creativity. The second is helping them understand that even the most gifted creatives still need a framework for pricing, positioning, and building sustainable careers. In our conversation, Kim explains why so many artists struggle with the entrepreneurial side of their work, what brands often misunderstand about creative talent, and why he eventually realized he had more in common with his clients than he expected.

    37 min

  5. Jun 9

    Would You Rather Risk Losing a Client or an Employee?

    This week, Sarah Segal, Jaci Russo, and Lena McGuire tackle a question many service business owners face: Which is the bigger risk—an employee who feels overburdened or a client who feels neglected? The discussion begins with Sarah explaining why she's had to reestablish boundaries with some clients who were texting and calling her employees after hours and bypassing the systems her agency has put in place. Sarah wants her team to be able to disconnect at the end of the day, and she wants clients communicating with the entire team assigned to their account—not developing overly close relationships with individual employees. In her view, protecting employees from burnout ultimately leads to better service for clients. Jaci approaches the challenge very differently. Her creative staff rarely communicate directly with clients. Instead, account managers serve as the sole point of contact, much like restaurant servers relaying orders between diners and the kitchen. The goal is to protect specialists from interruptions, keep them focused on their work, and ensure that client communication remains clear and consistent. The result is a lively conversation about competing priorities, client expectations, employee well-being, and the hidden risks that can emerge when clients become too dependent on individual employees. Plus: Have you ever had an employee leave and take clients with them?

    51 min

  6. Jun 5

    Dashboard: A Buyer That Doesn’t Want to Flip Your Business

    Sean Joy is head of M&A at Chenmark, a Portland, Maine-based holding company that acquires a handful of small businesses each year. At first glance, Chenmark may sound like a traditional private equity firm, but it isn't. The company is family- and employee-owned, and when it buys a business, the goal isn't to improve it and sell it a few years later. The goal is to own it indefinitely.In our conversation, Sean explains what Chenmark looks for in an acquisition, how it finds businesses to buy, what it's willing to pay, and how it approaches management after a deal closes. For owners thinking about succession, Chenmark offers a different path—one that sits somewhere between selling to private equity, selling to employees, or passing the business on to the next generation.

    38 min

  7. Jun 2

    ‘I’m Skeptical AI Is Going to Help Us’

    This week, we explore some contrasting opinions about artificial intelligence. Paul Downs has serious doubts that AI will ever have a significant impact on his business. Paul, who builds custom conference tables, says his business depends on something AI still lacks: real world experience. While AI can generate impressive images and concepts, he argues that it has no understanding of manufacturing constraints, material properties, production processes, or the capabilities of the people and machines that have to bring an idea to life. “An image of a thing that looks cool is not a design,” Paul says. “A design is a set of information that's informed by intelligence and experience.” Ted Wolf, who helps companies implement AI, agrees that AI can't replace the collective creativity and judgment of skilled people. But he believes Paul may be looking at the problem too broadly. Instead of asking whether AI can design and build custom furniture, Ted suggests breaking the workflow into smaller pieces and experimenting with targeted applications. “You know your business better than anybody else,” Ted tells Paul. “But don't look at the big picture and think that's the entire thing. There are many small pieces that people can start doing today.”The result is a thoughtful debate about one of the biggest questions facing small business owners: Is AI going to change everything, or are there businesses where human expertise will remain irreplaceable?Plus: Channon Kennedy shares what she learned from participating in a Goldman Sachs program for Black women entrepreneurs. And the owners discuss what debt can—and cannot—do for a business: “Funding does not fix a broken business model. It makes it die faster.”

    49 min

  8. May 29

    Dashboard: Uber for Landscapers

    When Bryan Clayton graduated from college, he discovered he had two options: take an entry-level job and a pay cut—or go back to mowing lawns, which was already making him more money. He chose the lawns. Over time, he built a commercial landscaping business that grew to $10 million in annual revenue before eventually selling it. But even while running that business, Clayton had been thinking about another problem: why was it still so hard for homeowners to hire a reliable lawn service?Despite having no background in technology, Clayton bootstrapped a platform called GreenPal, which connects homeowners with lawn-care specialists—essentially an Uber for landscapers. Today, still entirely self-funded by Clayton and his partners, GreenPal serves more than 300,000 users nationwide. In our conversation, Clayton talks about the operational mistakes that trip up many small businesses, how GreenPal uses both incentives and penalties to improve landscaper performance, and how the company is using AI to identify contractors whose businesses may be headed for trouble.

    33 min
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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
    544
  • Rating
    Explicit
  • Copyright
    © Copyright 21 Hats
  • Show Website
    21 Hats Podcast

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