21 Hats Podcast

This week, in episode 207, special guest Sharon Gillenwater lets us in on some dirty little secrets about Silicon Valley. She’s the founder of two businesses. The first one was backed by venture capital and then destroyed by venture capital. Despite that experience, Sharon tried to raise capital for her second business, Boardroom Insiders, a software-as-a-service marketing tool that helps businesses sell to the top decision-makers at big corporations. But this time, the VCs weren’t interested. So she bootstrapped the business with the help of an angel investor—and proceeded to learn some surprising lessons, many of which she shares in her book, Scaling with Soul. Perhaps the biggest surprise came when she sold her business and learned the happy lesson that the founder of a relatively small bootstrapped business can walk away with more money than the founder of a venture-backed business that sells for far more. In our conversation, Sharon is unusually candid about what it took to build her business, what she learned about B2B marketing, and precisely how much money she made along the way.

This week, Gene Marks reminds us once again that AI tools by and large still aren’t ready for prime time, but he does find a handful of people doing interesting things with AI—like getting a fresh take on the risks and opportunities their business is confronting. Plus: Gene and Loren Feldman discuss whether Gene is right that his business taxes will definitely go up if Kamala Harris is elected president.

This week, in episode 206, Shawn Busse, Jay Goltz, and Jennifer Kerhin talk about what it takes to plan and execute an employee retreat—especially in our post-Covid, more-remote environment. Do you go offsite? Do you take everybody? Do you delegate the planning? Do you try to measure the ROI? Jennifer tells us about the interesting responses she got when she encouraged her employees at her retreat to ask her anything. Shawn explains why he let his leadership team do the planning—and didn’t set a budget. Jay, meanwhile, offers a slightly different perspective: “My company retreat,” he tells us, “is I cut back on my advertising. That's my retreat.” Plus: How well does The E-Myth hold up as a playbook for business owners? Is it still relevant? Or was it written for a type of business that is far less prevalent today? And Jay tells us what he thinks of Wayfair opening a massive brick-and-mortar furniture store right down the expressway from his furniture store.

This week, Gene Marks explains the global tech outage: what actually happened, how seriously we should take it, and what business owners should do (but probably won’t) before the next outage. Those lessons include: 1) Try to keep some paper handy. 2) Stay calm. The internet is going to go down from time to time. 3) Have a disaster-recovery plan. 4) And if you don’t have a disaster-recovery plan, go to ChatGPT. PLUS: Gene discusses the upheaval in the real estate industry and why the CEO of an HR platform, Lattice, wound up on a subreddit called LinkedIn Lunatics.

Experts Paul Downs, Liz Picarazzi, and Jaci Russo discuss reviewing employees on the edge, using personality tests for conflict resolution, handling negative reviews, retaining mediocre performers, and reporting unethical competitors. They share insights on leveraging AI for brand planning, navigating employee performance challenges, and emphasizing integrity in business decisions.

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.