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
Oct 24, 2022 • 23min
Dashboard: Gene Marks Has One Piece of Tech Advice
Before you spend more on technology, he says, you might want to figure out how to make the best possible use of the tech you already have. Crazy, huh? Gene also talks about the key elements of a buy-sell agreement, how to get your employees to actually use your CRM system, and whether all of our ever-expanding array of productivity tools actually help productivity.
Oct 18, 2022 • 49min
Rule No. 1: We Will Not Have Civil Wars
This week, in episode 128, Shawn Busse, Paul Downs, and Liz Picarazzi talk about why it’s so easy for tension to break out inside a business. Liz sees tension brewing between her people in the office and her people in the field. Shawn often sees friction at businesses between sales and those who have to deliver what sales sells. Paul says there’s always the potential for tension when a project gets handed from one set of workers to another, and he’s created a very deliberate process to address it. We have, he says, “really tamped down the civil wars and started solving the problems, as opposed to letting them fester.” Plus: Are Shawn and Liz going to hit their numbers this year? And have the owners seen their health insurance rates for next year?
Oct 17, 2022 • 31min
Dashboard: Victor Hwang on Entrepreneurship in America
Founder of entrepreneurial advocacy organization Right to Start, Hwang suggests bipartisan policy changes that would help Americans build more businesses. He also talks about what he learned about entrepreneurs on his recent cross-country roadtrip, why funding of U.S. businesses is broken, and what Americans really think of business owners.
Oct 11, 2022 • 50min
Dana Opens in Dallas
This week, in episode 127, Dana White tells Paul Downs and Jay Goltz how her move to Dallas is going, including hiring a manager, firing a publicist, tweaking her business model, and for the first time, confronting competition. Dana also explains the surprising way she managed to get the financing to open her first salon on a military base, Ft. Bragg, which she now thinks could be up and running by the end of the year. Plus: Paul has to make adjustments to handle a sudden influx of business. And Jay is still looking for a head of HR. Should he post the ad on ZipRecruiter or Indeed? Should he offer a salary range in the ad? And is it reasonable for him to expect a follow-up email after an interview?
Oct 10, 2022 • 28min
Dashboard: Welcome to Health Insurance Season!
This week, as many businesses find out what they’ll pay for health insurance next year, Gene Marks and Loren Feldman talk about how businesses can save money. Gene explains why self insurance has become more feasible for smaller businesses and why he thinks it makes sense to offer employees better health coverage instead of a pay increase. Also, it’s probably time to revisit your workplace drug policies. And Gene and Loren discuss why the concerns of small businesses often get overshadowed by those of big businesses.
Oct 7, 2022 • 35min
Bonus Episode: Seth Goldman Brews Another Ice Tea
This week, in a special bonus episode recorded right before Labor Day, Seth Goldman talks about getting the disappointing news that Honest Tea, the brand he built and sold to Coca Cola, was being discontinued—and how it took him about two weeks to decide to create another tea business, Just Ice Tea, to fill the shelf space that Coke was vacating. Along the way, Goldman talks about why it made sense to sell a mission-driven business to a soda company, what he wishes he had done differently in the sale, what it was like being a Coke employee, what he’s been doing since leaving, how the beverage industry has evolved, and whether he’ll end up selling this business to Coke, too.
Oct 4, 2022 • 41min
Are You Hitting Your Numbers?
This week, in episode 126, Karen Clark Cole, Jay Goltz, and Sarah Segal discuss whether their businesses are meeting expectations and how that’s affecting their plans for next year. They also talk about how to handle an employee who doesn’t deliver, whether now is a good time to hire, and—in an answer to a listener question—how to make the transition from using contractors to hiring employees. And Karen explains why employee utilization—that is, what percentage of her people are actually billing clients—is the most important metric she tracks and one she tracks on an hourly basis. Plus: Notebooks or Notion? All three owners tell us how they try to stay organized.
Oct 3, 2022 • 19min
Dashboard: I Like Recessions
This week, Loren Feldman speaks with Tracy Bech, who is CEO of Starboard Collectives and who specializes in helping business owners who don’t have a financial background (she understands: she was once one herself). Tracy talks about the two most important ratios for business owners to watch if they think we’re heading into a recession. And she also talks about why she actually likes recessions—or at least sees opportunities in them.
Sep 27, 2022 • 40min
Raising Capital: 'It’s a Ticking Time Bomb'
This week, in episode 124, Shawn Busse, Liz Picarazzi, and Hans Schrei debate the merits and risks of taking outside capital. Clearly, it makes sense for some businesses. But what are the right circumstances? What are the alternatives? And what do you need to understand before going to the dance? For example, what are the dynamics of the entrepreneur-investor relationship? Are the entrepreneurs hoping the investors will bestow an opportunity upon them? Or is it actually the entrepreneurs who have an opportunity to offer? And who pays for the coffee? Plus: What do you do on those days when no one seems to be following your lead and the entrepreneurial loneliness sets in?
Sep 26, 2022 • 23min
Dashboard: The (Commercial) Rent Is Too Damn High
This week, Gene Marks and Loren Feldman talk about what business owners can do to protect themselves in the current environment of rising rents and increased volatility. Plus: What explains the recent boom in startups? And will it last? And what the Fed’s rate hikes mean for businesses. Also: you can’t just set your website and forget it.
