21 Hats Podcast

This week, we take a look back at the conversations we had last year about the many rewards and responsibilities of business ownership, highlighting some of our happiest, smartest, funniest, and most difficult exchanges from the past year. Along the way, we discuss topics such as escalating salary demands, how much profit a business should make, a new way to sell a business, the problems with ESOPs, how to sell cookies on LinkedIn, breaking a million dollars in annual revenue, escaping the valley of death, and the pain of having to fire a long-time employee. There aren’t many places where you can hear entrepreneurs talk about the real-life problems they are confronting right now, today, as they happen—with no guarantee of a happy ending. But those are the conversations I have every week with Paul Downs of Paul Downs Cabinetmakers, Shawn Busse of Kinesis, Jay Goltz of Artists Frame Service, Mel Gravely of Triversity Construction, Jennifer Kerhin of SB Expos & Events, Liz Picarazzi of Citibin, Jaci Russo of BrandRusso, Sarah Segal of Segal Communications, William Vanderbloemen of Vanderbloemen Search Group, Dana White of a soon-to-be-named successor to Paralee Boyd, and Laura Zander of Jimmy Beans Wool.In this episode, we also highlight several appearances by special guests who stopped by in 2023 to discuss their journeys, including Muhammad Abdul-Hadi of Down North Pizza, Jeff Braverman of Nuts.com, Michael Brown of Teamshares, Brad Herrmann of Text-Em-All, Grayson Hogard of Grove Cookie Company, Lance Tyson of the Tyson Group, and Ari Weinzweig of Zingerman’s. If listening to one of these highlights makes you want to go back and listen to the full episode, that can be done most easily by going to 21hats.com. There you’ll find a transcript of this episode with links to all of the episodes we sample.

So here was Muhammad Abdul-Hadi’s idea for a pizza joint: First, buy a building in one of the most troubled neighborhoods in one of the poorest big cities in the country. Open a restaurant despite having no experience in the food industry and do it during the pandemic when many restaurants are failing. And hire only people who, like Abdul-Hadi, are convicted felons. If that business plan sounds a little dicey to you, rest assured you would not be the first to suggest that to Abdul-Hadi. But he did it anyway. He built out the restaurant, and it opened in 2020 to lines that required people to wait as long as three hours for their pizza—thanks in part to a marketing plan that created excitement and scarcity by “dropping” pizzas the way some people “drop” special-edition sneakers. And now, Down North Pizza, which has been featured on best-of lists in national publications like Bon Appetit and The New York Times, is looking to expand. A special, year-end bonus episode.

In our last conversation of the year, Gene Marks tells Loren Feldman about the nine habits that he believes have helped him build a business. Those habits include meeting regularly with his accountant, meeting regularly with his clients, and over-paying his employees. Gene saves what he considers the most important suggestion for last: Make time to enjoy your family.

This week, in episode 177, Shawn Busse, Liz Picarazzi, and Jaci Russo discuss what they learned in 2023 and what they expect from 2024. After a tough year, Shawn is optimistic that his clients, having survived the turbulence of the past few years, are ready to spend money and try something different. Liz explains why she’s been willing to discount her products as much as 40 percent on Cyber Mondays and tells us about some new products she has in the works. Early in the year, Jaci, thinking she was going to have to staff up to handle two big new clients, dove into remodeling her offices—but those big clients have yet to sign on. “I might have jumped the gun a little bit,” says Jaci. Plus: Liz talks about her Midwestern mom, who can’t understand how Liz can charge so much for her trash enclosures. And Shawn raises the issue of how much money business owners should spend on marketing.

This week, Gene Marks shares his suggestions for anyone looking to save a little on taxes. Start with your retirement account. Better yet, start planning ahead for next year. Plus: What’s the best CRM for solopreneurs and microbusinesses? What artificial intelligence apps for business are worth trying right now? And what does Philly native Gene make of the $140 Philly cheesesteak?

This week, in episode 176, Paul Downs tells Jay Goltz and Jaci Russo about the latest developments in his year-long campaign to stop relying so heavily on Google AdWords. At a specially arranged, two-day marketing event, Paul got to sit down with a series of architects and designers who had already been vetted and who he hopes will become repeat customers. So far, Paul says, the results look promising. Plus, we also discuss: Do you write your website copy to please Google or to please people? Is there any way around skyrocketing property insurance rates? Why has Jay decided he no longer needs a chief financial officer? How big a disadvantage to owners are the new laws forbidding employers from asking job candidates about their salary histories? And would you reject a candidate simply for trying to negotiate a starting salary? I know someone who would.

This week, Gene Marks talks through the latest developments in customer relationship management software, which is both his area of expertise and a real pain point for many business owners. Among other things, Gene tells us about the impact artificial intelligence is already having on CRM, including what A.I. makes better as well as what it makes worse. Plus: How do you get salespeople to use your system properly? And what should you do if you’re completely frustrated and ready to dump your system?

It used to be that best practices in sales were pretty standard across the board. But since the pandemic and with the advent of artificial intelligence, says Lance Tyson, founder of the Tyson Group sales consultancy, it’s like the Wild West out there. Suddenly, everyone’s playing by different rules, and the best sales approach can vary, depending on the seller, the target, the industry, the region of the country. The keys, Tyson says in this week’s bonus episode, are to pay attention and stay flexible. Along the way, he also addresses a host of hot topics: How important is it to see a prospect face-to-face? Is cold-calling dead? Will A.I. replace sales trainers? What’s the right balance between base and commission? How do you handle the salesperson who can’t or won’t be a team player? How do you get salespeople to take maintaining their CRM seriously?

This week, in episode 175, Jaci Russo explains how she put an end to her eight-month drought of new clients. Jennifer Kerhin takes us through the bureaucratic nightmare of managing remote workers based out of state (“That is a headache that I don't wish on my worst enemy,” says Jaci, who has found a way to sidestep the problem). And Liz Picarazzi brings us up to date on her ongoing struggle to get her trash enclosures certified as bear-resistant. The common thread to these challenges may lie in these two questions: When is continuing to fight the good fight the definition of entrepreneurship? And when is it the definition of insanity? Plus: Why does it cost so much to exhibit at a trade show? And did you know that as recently as 35 years ago, there were still laws on the books requiring women to have a male relative cosign on a business loan? Those laws are now gone, thankfully, but Jaci, Jennifer, and Liz can all attest that that kind of paternalism is very much alive and well.

This week, Black Friday and Small Business Saturday will represent hugely important shopping days for many retailers. But Gene Marks tells Loren Feldman that the sales those days generate aren’t necessarily as important as the data they generate -- so long as the retailers are smart enough to capture it. Gene also talks about why business owners need to understand that when they sign their tax returns, they—and not their accountants—are responsible for what the returns show. Plus: why Gene loves shrinkflation as a pricing strategy and why it’s not just for those who sell food or products. It can even work for consultants like Gene.