21 Hats Podcast

This week, Gene Marks notes that the two major presidential candidates happen to agree on something, which is that we should stop taxing tipped income. Unfortunately, Gene explains, it’s a boneheaded idea. Plus: Gene’s been looking into the progress that manufacturing companies are making adopting artificial intelligence applications, and he says—at least when it comes to manufacturing—the promise of AI is starting to get real.

This week, in episode 209, Shawn Busse, Jaci Russo, and Jay Goltz discuss what it takes to stand out these days, especially if your business—like most businesses—isn’t exactly the Next Big Thing. What about trash collection? What if your business is selling scrap metal? What if you happen to be one of 69 picture framers in Chicago? What’s an owner to do to stand out then? Is it enough to execute really well? Can any business make itself remarkable? Shawn, Jay, and Jaci all believe it’s possible, and they offer examples from their own businesses as well as those they’ve observed. Plus: As Google waffles about whether it’s going to kill cookies on Chrome, will business owners still be able to target customers digitally? And Jay’s not happy about a very big bill he got from his accounting firm. Should he just go ahead and pay it?

This week, Gene Marks offers some suggestions as to what it would take for the presumptive Democratic nominee to earn his vote and those of other small business owners. Suggestion No. 1: make clear that in the debate over whether to extend the Trump tax cuts she favors keeping the Qualified Business Income Deduction for owners of pass-through businesses. He’d also like to see her promise fewer regulations and more tax breaks for owners trying to sell their businesses.

This week, in episode 208, Paul Downs, Mel Gravely, and Sarah Segal talk about the tricky calculation all entrepreneurs must make between sticking to their vision and accepting advice. Sarah explains why she is reluctant to take advice from people who don’t really know the inner workings of her business, which is pretty much everyone. Paul, on the other hand, says taking advice from outsiders helped save his business during the Great Recession. And Mel talks about why he thinks every business should have a board of advisors—and why he thinks having a board would have saved him from a big mistake he made recently. But then, Paul asks: If you do have a board, can you not take its advice? Plus: Reacting to a recent post on Reddit, the owners discuss the right way to wind down a failing business, a process with which Mel and Paul have some familiarity.

This week, Gene Marks talks about three very different topics. First, he explains how helping employees find affordable health care can actually generate business growth, and he walks through the ways even very small businesses can help. Next, Gene weighs in on proposed legislation in California that is designed to keep AI models from causing catastrophic harm. And finally, he explains how a new hire just out of college helped a Chevy dealer create a sitcom parody that went viral. But did it sell cars?

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.