21 Hats Podcast
21 Hats
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.
Episodes
Mentioned books
Feb 7, 2023 • 43min
Walking Away From a Salary
This week, in episode 142, Sarah Segal tells Shawn Busse and Jay Goltz why she’s decided to take her public relations business back after selling it two years ago to a larger firm so it could handle the back-end stuff and allow her to focus on public relations. For Sarah, the immediate result of the decision to break away has been an exhausting few months starting over, including reincorporating, finding health insurance, and reducing her own pay. Meanwhile, Jay suggests an old-school marketing tactic that involves leveraging an envelope, a stamp, and the post office. And Shawn explains how he created a sales process that has allowed him to remove himself from day-to-day sales. Plus, a listener asks the three owners, “When do you know if you've made it? Or do you never know?” Shawn, Jay, and Sarah—three owners at very different stages of building a business—offer three very different answers.
Feb 6, 2023 • 23min
Dashboard: So You Think Building a Business in the U.S. Is Hard?
Well, it is, but after spending a month in London, Gene Marks says inflation, regulation, and entitled employees make it even worse there. In fact, Gene says he’s going to stop complaining about conditions in the U.S. (We’ll see.) Plus: why Gene thinks even small businesses should offer unlimited PTO, how to make sure you don’t fall prey to one of the Employee Retention Tax Credit scams, and Gene’s list of things a small business can do with ChatGPT.
Jan 31, 2023 • 50min
How Much Profit Should Your Business Make?
This week, in episode 141, Shawn Busse, Paul Downs, and Jay Goltz go right to the bottom line. Shawn points out how easy it is for businesses to fool themselves into thinking they’re more profitable than they really are. Paul talks about how margins can vary from year to year, especially if an owner decides to invest in improving the business—as Paul’s doing right now. Jay says he’s long sought a 10-percent profit margin, but so far, he hasn’t managed to get there. Plus: Shawn explains how he solved his accounts receivable problem. And have you looked at the 401(k) accounts of your employees lately? If not, there’s a good chance you’re going to find that they’re not saving a whole lot. Is that just the employee’s problem, or is it also the owner’s problem?
Jan 30, 2023 • 20min
Dashboard: Getting an SBA Loan With No Down Payment
This week, 21 Hats columnist and finance expert Ami Kassar assesses the state of small business lending with Loren Feldman. Among other things, they discuss why it’s important to manage your EIDL loan carefully, how much of a line of credit every business should have, how to get a zero-percent-down loan from the SBA, and how much progress Ami has made toward firing himself.
Jan 24, 2023 • 49min
Why Isn’t This Product Selling?
This week, in episode 140, Shawn Busse, Liz Picarazzi, and Sarah Segal talk about how long to keep trying when a product isn’t selling the way you expected. For Liz, the problem product is her package locker, which is designed to defeat porch pirates but hasn’t really taken off—especially considering how widespread the concern is. Could the glitter-bomb guy be the answer to Liz’s marketing challenge? Or is it time for her to back off? Plus: In the age of Zoom and remote workers, what have the owners figured out about running effective meetings? And if you're pricing a range of services in a proposal, do you price your offering a la carte? Do you always charge the same prices? And is there a way to ease a client into a monthly retainer?
Jan 23, 2023 • 22min
Dashboard: ChatGPT, Salesforce CRM, and the Employee-Contractor Dilemma
This week, Gene Marks and Loren Feldman discuss an “inconvenient truth” about Salesforce CRM, which is that it’s probably not right for most non-corporate businesses. Already using it? Gene explains how to assess whether it’s worth making the switch to a more affordable platform. Plus: Gene thinks the Department of Labor’s new worker-classification law will be a disaster but suggests some fixes. Gene also has some thoughts about ChatGPT: real potential, not there yet.
Jan 20, 2023 • 43min
Bonus Episode: A New Way to Sell Your Business
Learn about Teamshares, a company that buys struggling businesses from retiring owners and turns their employees into owners to address income inequality. Discusses challenges and lessons from acquiring over 60 businesses. Highlights the importance of recruiting and training leaders, maintaining relationships with former owners, and implementing employee stock ownership plans. Emphasizes the challenges of running a small business and the need for continuous learning, good financial practices, and fair compensation for employees.
Jan 17, 2023 • 50min
I’ve Always Been Afraid to Raise Prices
This week, in episode 139, Jay Goltz, Dana White, and Laura Zander have a wide-ranging conversation that starts with the challenge of pricing. Do you set prices based on what you think the market will bear? Or do you set prices based on your own rising costs and what you need to charge to make a profit? And how much profit should a business expect to make? Along the way, the owners also discuss why Laura wants to keep buying businesses (don’t tell her husband, Doug), what Dana needs to do to get her new salon open at Fort Bragg, and why both Dana and Laura are going all-in on influencer marketing. Jay, on the other hand, isn’t entirely convinced that social media marketing works for his picture-framing business. Plus: Should a business owner know every employee’s name? What if you have 130 employees?
Jan 16, 2023 • 26min
Dashboard: The State of Small Business, 2023
John Arensmeyer, founder and CEO of Small Business Majority, an advocacy group for entrepreneurs and businesses, talks to Loren Feldman about how businesses are faring, what issues they are most concerned about, and where his organization is focusing its energy. Among other things, they discuss access to capital, the need for immigration reform, who benefits from non-compete agreements, California’s experiment in fast food regulation, and the Labor Department’s approach to independent contractors.
Jan 10, 2023 • 50min
How’s Your Compensation Plan Holding Up?
This week, in episode 138, Shawn Busse, Liz Picarazzi, and William Vanderbloemen discuss what it’s been like trying to make sense of employee compensation in a time of COVID, the Great Resignation, inflation, and a looming recession. Shawn’s business model is evolving, and he’s trying to adjust his mix of employees to fit the new model with as little disruption as possible. Liz is expecting a year of big growth and is assessing how that will affect her staffing needs—especially as she introduces new benefits, including health care. And William is trying to create a more sustainable compensation structure while also breaking his employees’ expectation that they will always get a year-end bonus. Plus a listener asks: What tasks are the owners still doing, even though they know it’s not worthy of their time? (Aside from participating in this podcast, of course.)
