21 Hats Podcast

Gene has a problem with it. He doesn’t think it goes far enough. That’s because he thinks it gives businesses with fewer than 25 employees an unfair advantage. Gene also warns that several “huge tax increases” are looming for small businesses -- but are they really tax increases? Plus: striking the right balance between salary and commission when paying sales people.

This week, for episode 154, we did something different. We recorded this session in Chicago at our very first 21 Hats in-person event. In May, some 20 impressive entrepreneurs from around the country, from different industries, with businesses of different sizes and stages, gathered to talk shop for three days. The last thing we did was to record this episode in which we gave the participants the opportunity to ask the podcast regulars anything they wanted. Those regulars included Jay Goltz, Sarah Segal, and Dana White, and the questions addressed everything from hiring to motivating to delegating to pricing to coping with stress to what they wished they’d figured out sooner and to what still keeps them up at night. And when there were no more questions, I asked those who attended the Chicago event what I could have done to make it better. That I would invite criticism in a conversation being recorded for a podcast audience, took some of the participants by surprise. But, as you’ll hear, it worked out pretty much the way I hoped.

This week, Ami Kassar tells Loren Feldman that in running MultiFunding, which helps businesses figure out their finance needs, he frequently meets business owners who know what they need to do but are reluctant to take that next step. One way to build your confidence, Ami says, is to make sure you really understand what drives your business model, which may require bringing in a fresh set of eyes, perhaps from a fractional CFO. Ami also talks about the current state of lending, his concerns about where the SBA is headed, and why business owner peer groups are so valuable.

So, I decided to give the 21 Hats Podcast crew this week off. Between the Memorial Day holiday and our first 21 Hats in-person event the previous week in Chicago—attended by five of the podcast regulars—it seemed the right thing to do. It also seemed like a great opportunity to reprise one of our favorite all-time episodes. It’s not a used episode; it’s a certified pre-owned episode, or better yet, a greatest hits episode. We first published it in December of 2021, and it features highlights taken from the podcasts we’d published up until that point that cover many of the risks and rewards of business ownership, including what it’s like to sell your business, to fire an employee, to risk your own home in order to get financing, and even to deal with serious mental health issues. If you’re new to the podcast, I think you’ll find that these conversations bring real context to the journeys of the entrepreneurs you’ve been following here. But even if you’ve heard some of these discussions before, I think you’ll find them a refreshing reminder that choosing to build a business can be a noble mission, but it generally doesn’t come with an owner’s manual. We’re all figuring it out as we go.

This week, in episode 153, William Vanderbloemen says good public relations is absolutely worth the time and money. Paul Downs says PR hasn’t worked for him. At this point, he says, there are all kinds of ways he’d rather spend his time and money. Meanwhile, Sarah Segal, who owns a PR firm, offers some tips on how to approach and how to employ a firm effectively. Along the way, we discuss what’s expensive when it comes to PR and whether owners can just do it themselves. Plus: Paul explains how he dug himself out of a sales hole by not doing anything differently. And we find out how the owners feel about all of the new ways they’re being asked to leave tips.

This week, Gene Marks tells Loren Feldman that he thinks the ban signed by Montana's governor is a political stunt that could do real damage to businesses that have come to rely on the app. And yet, there seems to be momentum for similar bans in other states and even at the federal level. Plus: how to avoid ERTC fraud, why bankruptcies are skyrocketing, and should the business community be doing more to warn against risking default?

This week, Shawn Busse and Loren Feldman talk to John Garrett about his contrarian approach to newspapers, marketing, and competition. Garrett has built a Texas-based chain of print newspapers that has managed to outcompete established news organizations and digital platforms for both community engagement and local advertising. Not surprisingly, when he first took out a $39,000 credit card loan in 2005 and started telling people that his business model would feature a monthly print publication that he would mail to everyone in his target communities for free, he didn’t get a lot of congratulations. And not everything he’s tried has worked. An expansion into Arizona, Tennessee, and Georgia, for example, failed early in the pandemic. But almost 20 years after its debut, a period during which most local publications have been in retreat, Community Impact is thriving. And from his seat as a publisher, Garrett offers a perspective on marketing that any business owner would be wise to consider.

This week, Gene Marks tells Loren Feldman that businesses should be making contingency plans in case there’s a default, especially if they rely on government contracts. Be careful how you spend and how you stash your cash. Plus: Gene gloats a bit about the end of the age of the worker (and then has some second thoughts). He also says reports of the death of the metaverse are greatly exaggerated and that it wouldn’t be so terrible if the government loses the ability to regulate.

This week, in episode 152, Jay Goltz, Liz Picarazzi, and Sarah Segal talk about the inherent conflicts between being an entrepreneur and being a CEO—and the different skill-sets each role requires. Does it make sense for the same person to do both jobs? Is being CEO even a full-time job? And when does it make sense to replace yourself as CEO? Liz says she’s thought about it. Jay, not so much: “Could I have found somebody 10, 15, 20 years ago who was a better manager? Sure. But it just wasn't worth it.” Why not? “It's gonna cost you $250,000 a year,” Jay says. “Is it worth paying that?” Plus: Liz and Sarah talk about positioning a company to be acquired. And Sarah proposes a PR campaign for Liz’s package bins right on the spot.

This week, John Arensmeyer, CEO of the Small Business Majority advocacy group, and Loren Feldman talk about some of the most intractable problems confronting business owners. And John offers some reason for hope -- mostly, he says, because there’s a growing, bipartisan effort to level the playing field for smaller businesses. The debt ceiling, of course, is another matter.