21 Hats Podcast

As CEO of MultiFunding, Ami Kassar sees a lot of small business P&Ls, and he sees how banks are responding to loan applications. And in his view, the ground is starting to shift—although he’s not sure where we’re headed. But in times of uncertainty, he emphasizes, there are always opportunities

This week, in episode 204, Jay Goltz and special guest Cathy Caroll talk about family businesses, with Jay asserting that they are even more combustible than most people realize and with Cathy offering some smart coping strategies. We start with Cathy explaining how her own experiences in a family business propelled her to write a book, Hug of War, and to become a family business coach. Why are family businesses so difficult? Well, says Cathy, it’s because you’re trying to combine a family mindset with a business mindset, which she says, is a little like “living in socialism and capitalism simultaneously.” Of course, she says, it also has to do with mixing love and money—“You’re just gonna get sparks”—and with the brutal challenge of transitioning from one generation to the next, when every decision can feel like a repudiation or rejection. Still, it was that stew of anxiety, resentment, and trauma that helped Cathy find her calling, which is to help others do in their family businesses what she could not in hers.

This week, John Arensmeyer, founder and CEO of Small Business Majority, reminds us that the State Small Business Credit Initiative is sending billions of dollars through the states specifically for small businesses. Because every state is handling the money differently and there is no one-stop shop for information, there is some confusion—but the money is real and John explains how to figure out if you’re qualified. Plus: He also explains why he’s surprised some business groups are celebrating the recent Supreme Court decisions on regulation, why his organization favors the ban on non-competes, and why he thinks the small business tax break contained in the soon-to-expire Trump tax cuts can be improved.

This week, in episode 203, special guests Laura Anderson, founder of Local Ocean, and Peter Koehler, her succession-planning advisor, explain why Laura decided to sell her thriving seafood business in a transaction that created a business model that is neither widely known nor widely understood. It’s called an employee-ownership trust, and there are only about 50 of them in the United States. But their numbers are growing here and abroad, and for good reason. The trust model offers owners something of a choose-your-own-adventure option that can allow them to sell for a market rate in a relatively uncomplicated transaction that makes it far more likely the business will remain true to its established mission—especially when compared to selling to private equity or even to an employee stock ownership plan. Of course, there are challenges, including getting a bank to consider financing one of these deals. But in this episode, Laura explains why, with Peter’s help, she decided to trust the trust.

No, says Gene Marks, who — it may surprise you to hear — offers three main reasons he doesn’t believe business owners should panic over the U.S. government’s growing debt. That said, he does believe that we are likely to have to operate in an environment of higher inflation and higher interest rates for some time, and he says that is likely to require some adjustment in the thinking of business owners.

This week, in episode 202, Paul Downs, Jaci Russo, and Sarah Segal talk about how they wound up pitching their products and services not to consumers, but to other businesses. They all agree that selling to business is more profitable, and they all agree that it has other advantages, as well. “In general,” says Paul, “it's easier to sell to businesses because the person you're talking to, it's rarely their money.” But some aspects of selling B2B can be harder. For example, how do you break through and reach the right person at a business, especially if you’re trying to reach the owner directly? And of course, there’s always a learning curve: Selling to a big business requires a level of professionalism that can be challenging, especially early on. Plus: Sarah explains why—even though she had to lay off people last year—she’s doubling her office space this year. Jaci is exploring what policies make hybrid offices most effective. And Paul, who says he’s having his best year ever, spells out the way he calculates when it’s time to add employees, as he had to do earlier this year.

This week, Gene Marks and Loren Feldman discuss the Supreme Court’s decision, released on Friday, that takes authority to interpret laws passed by Congress away from federal agencies and gives it to judges. Whatever you think of the merits of the ruling, Gene points out, it creates tremendous uncertainty for businesses trying to comply with the law. For example, a new overtime rule is supposed to go into effect today. Should businesses start following it, Gene asks? Or wait to see what happens with pending litigation?

This week, in episode 201, we bring you what we’re calling an Entrepreneurial Fish Bowl with Chris Hutchinson. As you may remember, we recorded one of these at our 21 Hats Live event in Fort Worth, where I shared some of my challenges trying to build 21 Hats and got feedback from the group. We recorded that conversation and turned it into a podcast episode. This time, we’re doing the same thing except it will be Jaime Echt, founder and CEO of The Crafters Workshop, who is going to explain her challenges to a virtual group of 21 Hats entrepreneurs. As you’ll hear, Jaime’s challenges are real: Her sales are down. Her customers are aging. Her lease is up. And she’s not sure what she should do next. We’re going to see if a group of 21 Hats Founding Members can offer some support and advice.

Companies don’t like to admit it, says Gene Marks, but that’s kind of the point. So far, it’s mostly big companies with millions to spend that have been able to replace humans with bots, but he believes smaller businesses will soon be doing the same thing. Should we be worried about that? He doesn’t think so. Plus: Why a lot of businesses still don’t offer 401(k) plans. And if job candidates want to bring a parent along to an interview, Gene says he’s fine with that.

This week, in episode 200, Shawn Busse, Liz Picarazzi, and Jaci Russo talk about how the marketing world is turning upside down. For decades, business owners have treated search engine optimization as something of a religion. They may not have been able to explain it, but they had faith that, if they obeyed the rules, Google would discover their sites and rank them. But search engines are getting a lot less generous about sharing links, and Shawn fears there’s an apocalypse coming for businesses that rely too heavily on SEO. Jaci’s a little more optimistic: “There'll be some other places to go get free traffic,” she says. “There always are.” Plus: Liz gives us an update on her recent trip to Vietnam in search of a contract manufacturer. And in a case study ripped right from the subreddit headlines, I ask the three owners: What do you do if a loyal, hard-working employee starts a side hustle selling a product that doesn’t compete with your product but looks a whole lot like it?