

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

Mar 13, 2023 • 22min
Dashboard: Taxes, Regulation, and a Punch to the Face
This week, Gene Marks and Loren Feldman discuss what it means for small businesses that some tax deductions are going away, some new regulations are arriving, and Joe Biden has released a budget proposal. Gene also counters the Bare Minimum Monday meme with a suggestion for what practitioners of Bare Minimum Mondays can do on Tuesday.

Mar 7, 2023 • 50min
Marketing Workshop: Turning a Failing Nut Shop into Nuts.com
This week, Shawn Busse and Loren Feldman talk to Jeff Braverman about how he walked away from a career as an investment banker and went to work in the family’s nut store, the Newark Nut Co. “My dad and my uncle told me I was nuts,” says Jeff. But with an instinct for taking risks—like acquiring the URL Nuts.com—Braverman has turned the family business into an internet juggernaut, unleashing years of explosive growth. And despite being a former investment banker, he’s managed to do that without taking any outside capital. And he’s far from finished. “To this day,” he says, “we're doing deep brand research: What is Nuts.com? What can it be? Can it scale? Can it transcend just the word nuts?”

Mar 6, 2023 • 25min
Dashboard: The Three Reports Every Business Owner Needs
This week, Gene Marks tells Loren Feldman that too few business owners really know how their business is performing. He suggests three reports that they should be reviewing -- beyond their monthly financials -- if they want to get a better grip on managing their business. Plus: Gene explains how businesses can save money on energy and why everyone should hire a CRM consultant (like Gene, for example).

Feb 28, 2023 • 47min
What It Means to Break $1 Million in Revenue
This week, Liz Picarazzi and Sarah Segal talk about their attitudes toward growth, including how they set goals, the tension between revenue and profit, deciding when growth requires additional bodies, choosing between contractors and employees, and how they would use the money if someone were to give them a million dollars to invest in their business. Plus: What will it take for them to consider themselves successful?

Feb 27, 2023 • 20min
Dashboard: Coping With HR Issues Without an HR Staff
If, like Gene Marks, you think dealing with employees is a pain, Gene has a suggestion for you: professional employer organizations, or PEOs. It’s a way to outsource all of the functions of HR—even including, if you want, health insurance. Gene also talks about why too many businesses ignore the many resources government has to offer business owners, why it’s time to start preparing for a government shutdown, and why Kevin O’Leary--aka Mr. Wonderful--is a buffoon.

Feb 21, 2023 • 43min
Marketing Workshop: Selling Cookies on LinkedIn
This week, Shawn Busse and Loren Feldman are doing something a little different. This is the first in a series of episodes we’re calling Marketing Workshops. In an attempt to confront one of the biggest pain points business owners face, we’re offering a series of conversations with owner-operators about their marketing experiences: what’s worked and what hasn’t. We’re starting with Grayson Hogard, co-founder of Grove Cookie Company. For Grayson and his wife, Marie, the company is a bootstrapped side hustle, but in a very short time they’ve come to some very smart conclusions about their marketing that might seem counterintuitive at first. Most importantly, they’ve figured out that the most effective sales channel for their cookies is, of all places, LinkedIn.

Feb 20, 2023 • 22min
Dashboard: The Price of Tipping, Virtual Offices, and Men’s Underwear
This week, Gene Marks and Loren Feldman talk about why tipping is a terrible system that we probably will never change, why Gene believes giving up a real office for a virtual office didn’t save him money, and what the purchase of mens underwear can tell us about the economy. Plus: Gene says there are 27 things businesses can do with ChatGPT right now—although he does offer a few caveats.

Feb 14, 2023 • 53min
ESOPs Are Great. But Not for Me
Last week, Jay Goltz continued his exploration of employee ownership, flying to Portland to meet up with Shawn Busse and Jim Kalb, a friend of 21 Hats who has already sold a portion of his business to his employees. The three owners planned to attend a conference promoting employee stock ownership, but things went somewhat awry. Jay and Shawn left the conference early, Jim canceled his flight, and as has happened before in his brushes with ESOP professionals, Jay walked away feeling convinced—convinced, that is, that an ESOP probably isn’t right for him. Two days later, we taped this podcast episode, which quickly turned into one of the more raucohttps://21hats.com/us conversations you are likely to hear about a somewhat technical business topic—although we did manage to find some clarity in the end. In Jay’s words, we agreed to agree.Along the way, we confronted quite a few relevant questions, such as, do ESOPs have to be so confusing? Are the professionals who pitch ESOPs trying to make them seem complicated? If Jay wants to sell 30 percent of his business to his employees but continue running it, how much control would he have to give up? Will an ESOP make life easier or harder for Jay’s two sons in the business? Instead of an ESOP, could Jay accomplish most of what he wants to accomplish by setting up a profit-sharing bonus plan through his 401(k)? Hanging over the conversation was a larger, more philosophical issue: What exactly do business owners owe their employees? And whatever those obligations are, do they extend beyond the sale of the business? Do they extend beyond the grave?

Feb 13, 2023 • 23min
Dashboard: The Good News About Gen Z
This week, Gene Marks and Loren Feldman talk about what Gen Z values in a job. The research suggests it’s not the job -- it’s more about people and meaning. And that’s good news for smaller businesses, because those are things they can offer. But you might want to emphasize that in your job descriptions. Plus: Is this recession happening or not? And what will ChatGPT’s upending of search mean for all of the businesses who’ve been investing in SEO? They’re not going to be happy, says Gene.

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.