This week—and next week—we take a look back at the conversations we’ve had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges, including Paul Downs on how he diced which employees to lay off, Jennifer Kerhin on asking ChatGPT to review her performance as CEO, Kate Morgan on why she’s been reluctant to raise her prices, Liz Picarazzi on her search for a domestic manufacturer for her trash enclosures, Ari Weinzweig on why Zingerman’s charges so much for a hamburger, and David C. Barnett on why your business is probably worth more to you owning it than selling it.

As the year comes to a close, I often reach out to John Arensmeyer, who is founder and CEO of Small Business Majority, to get his take on the state of small businesses in America. The picture John paints this year, based on his own observations as well as a recent survey, is not pretty. He points to a host of issues -- health insurance, tariffs, immigration, cuts to federal programs -- every one of which can represent an existential threat to a business. John does note, however, that through it all, owners appear to remain surprisingly optimistic heading into 2026—even if that optimism speaks more to the resilience of business owners than it does to the economic outlook.

This week, in Episode 271, we welcome another new voice to the podcast: Channon Kennedy, who takes us inside the side hustle that’s become her second full-time job. Channon is the inventor and patent holder of the Morgan Square, a clever measuring tool—here’s a demonstration—that’s racking up awards, expanding its distribution, and carving out space for a woman founder in a traditionally male-dominated industry. This is a true bootstrap story. Channon’s numbers are modest enough that she still does most of her own fulfillment at night after her day job as a banker—and she loves it. “Every time I get an order,” she says, “I feel like I'm wrapping a Christmas present. I'm just so excited that somebody wants something that I've created.” Plus: Paul Downs checks in with an update. After posting his best year ever in 2024, he was blindsided when sales suddenly stalled earlier this year, forcing him to lay off a third of his employees. Sales have since rebounded, but now he’s staring at a backlog and a different dilemma: Does he hire aggressively to meet the higher demand—or play it safe until he sees how 2026 begins?

This week, in episode 228, Lena McGuire—in her first appearance as a regular on this podcast—tells Paul Downs and Jaci Russo about her plans to turn her hobby, remodeling homes, into a real business. In just her third full-time year of building Spóca Kitchen & Bath, Lena says she has already experienced both a quick rise in revenue and then a surprising decline, a decline she attributes mostly to marketing issues. One of those issues, she says, is that she refreshed her website and it started producing more prospects—but fewer qualified prospects. That said, Lena is off to an impressive start, having targeted a well-defined niche, having created a clear process to connect homeowners and contractors, and having demonstrated both a real need for her services and an ability to learn from her mistakes. “I don’t look at failure as failing,” she says in a conversation we recorded in December. Plus: Paul tries to explain why his revenue surged 50 percent in 2024. Now there’s a problem we’d all like to have.

This week, in our first Dashboard conversation of 2025, Gene Marks talks about why he and other owners are excited about what they think will be a more business-friendly environment this year. But Gene also warns that tariffs and deportations are likely to drive inflation higher and discourage the Federal Reserve from cutting rates, which may not produce the economic growth owners are expecting. Plus: There are big changes coming to retirement-plan rules that owners should know about.

This week, we take another look back at the conversations we had over the past year, highlighting some of our happiest, smartest, and most insightful exchanges. We discuss whose advice is worth taking, whether any business can be remarkable, which businesses should try EOS, why family businesses can be so vexing, what to do when big businesses refuse to pay small businesses, the challenges of pricing services, the backlash against diversity, and finally the remarkably moving story of the moment that propelled one entrepreneur first to get fired and then to launch a remanufacturing business that would hit $60 million in revenue in less than five years.

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 Shawn Busse of Kinesis, Paul Downs of Paul Downs Cabinetmakers, 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, and Laura Zander of Jimmy Beans Wool. They come from a wide range of industries and geographies and experiences, but they all share a willingness to talk about not just what they get right but what they’ve learned from getting stuff wrong.

This week, and next week, we take a look back at the conversations we had over the past year, highlighting some of our happiest, smartest, funniest, and most difficult exchanges. We discuss topics such as whether the Great Resignation prompted business owners to overreact and overpay employees, whether the anxiety of owning a business ever subsides, what young couples should ask themselves before one of them starts a business, why owners find marketing so difficult, how owners can sell a business that just won’t sell, and what keeps entrepreneurs going when the going gets really tough.

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, and Laura Zander of Jimmy Beans Wool. They come from a wide range of industries and geographies and experiences, but they all share a willingness to talk about not just what they get right, but what they’ve learned from getting stuff wrong. If listening to one of these highlights makes you want to hear the full episode, that can be accomplished 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.

This week, in episode 225, Shawn Busse, Jennifer Kerhin, and Jaci Russo talk about how their businesses did this year and what they’re planning for 2025. Jaci and Shawn have been surprised by a surge of new clients in December, which they say never happens. And Jennifer is excited because she’s confident that in the first quarter she will finally exit the Valley of Death—that transitional period growing companies experience when the people and processes that made them successful stop working (AKA No Man’s Land). Along the way, the owners discuss the relative merits of promoting from within vs. hiring from without, how long it should take to onboard senior-level hires, whether it’s better to err on the side of budgeting for too little growth or too much, how they’re training employees to use artificial intelligence, and what Jennifer can do to stop spending so much time writing and pricing proposals.

This week, Tracy Bech, co-author of the “60 Minute CFO,” talks about how business owners can get more comfortable with their financials. Very few people go into business because they’re good at accounting, but that doesn’t mean it’s acceptable to throw up your hands and say, “I’m not a numbers person.” To drive a car, Tracy says, you don’t have to understand how the engine works—but you do have to know how to read a few gauges. Well, the same is true of driving a business, and she’s got a few suggestions.

This week, in episode 224, special guest Karla Trotman explains, step by step, how she has managed to navigate the challenges and opportunities that only a family business can offer. Karla grew up around a manufacturing business, Electro Soft, that her father started, but she never intended to make a career of it. Instead, she found success in corporate America, but over time, she also came to realize the true wealth-building power of owning a business, any business. “It's not a beauty salon,” she says. “It's an asset. It's not a shoe-shine store. It’s an asset.” That realization sent her back to Electro Soft, which thrilled her father. They agreed to work together for three years after which he would retire and she would buy the business. And that’s pretty much what happened—although, as Karla tells us, thanks to some family dynamics that had to be negotiated, the transition didn’t take three years. It took 11 years.

In many cases, Shawn Busse tells us this week, they do, which is why he believes all businesses should be innovating constantly. That’s a lot to ask of small businesses, many of which are just trying to make it to the next payroll, and Shawn acknowledges that there are exceptions. But if, for example, a private equity firm starts buying up your competitors and investing money in them, innovation may be your best hope. How do you get started? Shawn offers some concrete steps to consider if you want to try to think differently about what you do. Step one? Talk to your customers.

This week, in episode 223, Shawn Busse, Jay Goltz, and Sarah Segal talk about why they’re not going to hit their numbers for 2024 and what they’re expecting from 2025, especially regarding tariffs, immigration, and regulation. Shawn says his business has been producing and closing fewer leads. “Clearly,” he says, “we’ve gotta change something.” Jay doesn’t think furniture sales will recover until mortgage rates come down, and he’s bracing for tariffs and deportations that he hopes won’t actually come: “I have to believe,” he tells us, “that somebody in government is going to figure out this isn't a good thing.” Sarah, meanwhile, says her revenues are down, but she’s taking solace from the fact that she is ending the year with a stronger book of business than she ended with last year. Plus: the owners discuss what it means that a judge in Texas has blocked the new overtime law. And they offer guidance to a cafe owner who raised her prices only to get hit with another 25-percent price hike from her main supplier, leaving her to wonder whether she should raise prices again or “eat the loss and pray for a miracle.”

This week, Gene Marks tells us he’s found the next killer app for small business, and it’s not something that’s theoretical and might be ready sometime next year. It’s ready now, and it’s Google’s NotebookLM. Gene had reviewed it previously and found it wanting but took another look at the latest version and found it could do things like streamline a job search and spot anomalies in his financials. But Gene also offers a caveat for rolling out any AI app or even a CRM: if you don’t configure it right, you can run into some very big problems. Plus: he also discusses the latest in password technology.

Yes, says Gene Marks, it’s easy to make fun of all of the ways in which AI chatbots can fail (don’t even think about asking them to create an image of a Yorkshire Terrier hitting a homerun), but that’s no excuse to sit on the sidelines. Get the paid version. Get some training. Get your employees some training. And get to work. On what? Gene gives some examples of his favorite use cases.

This week, in episode 222, we bring you another Entrepreneurial Fish Bowl with Chris Hutchinson. These Fish Bowls are our virtual brainstorming sessions where we offer business owners the opportunity to pose a challenge they’re facing to a group of owners and entrepreneurs from the 21 Hats community. This time, our volunteers are Alvin Elbert, founder of A.R.E. Manufacturing, and his daughter Megan Perona, who explain that their company had its best year ever in 2022 but has seen business fall off since then. For 40 years, A.R.E. grew slowly but steadily on word of mouth. More recently, however, the Elbert family has concluded that it’s time to do some real marketing. Like a lot of owners, though, they’re a little overwhelmed by the options, unsure where to begin, and wary of wasting money. They also happen to be going through a family ownership transition. The 21 Hats brainstormers begin by asking a lot of questions, including whether the owners have invested in search engine optimization, whether they’ve gone back to some of the customers they lost to China, and whether they’ve considered hiring a marketing agency.

This week, Victor Hwang shares some surprising reasons to be optimistic about entrepreneurship in America. For one thing, Victor, who is founder of Right To Start, an advocacy group, says that he can’t remember a presidential election where entrepreneurship was as much a part of the conversation as it was in this one. For another, he points to a series of policy changes at the local level that have made it far easier to start businesses and that he believes will serve as a blueprint for other jurisdictions looking to cut red tape. As always, Victor brings news that has yet to reach most of us—including an issue he plans to address in 2025: standard lending rules that actually discriminate against entrepreneurs by making it harder for them to get a home mortgage.

In 2021, Mel Gravely wrote a book, Dear White Friend, that was aimed primarily at fellow business owners. In the book, Mel tried to make it easier for owners to have genuine conversations about race. He suggested strategies for those, perhaps motivated by the murders of Ahmaud Arbery and George Floyd, who might want to engage. He acknowledged that emphasizing diversity can be hard work. He acknowledged that some of his own efforts had failed. But he also pointed out that he himself had been, in his words, “an affirmative action baby” and that that investment had paid off for his college, his previous employers, and the city of Cincinnati. It’s been less than four years since Mel published Dear White Friend, but of course that was a very different time. This week, he talks about the backlash that has ensued and the strategies he still believes can work for those who don’t consider diversity a dirty word.

This week, Gene Marks tells us that the first really meaningful AI applications aimed at smaller businesses will arrive in the coming months. Gene does offer some caveats, including his mantra: “Never buy the first version of anything from Microsoft.” But he also offers some tantalizing examples of things AI agents will do for business owners in the very near future, like qualifying sales leads and then putting a sales rep through a role-playing exercise to prepare for a specific client. What should owners do now to prepare? “Beat up your vendors,” says Gene. “And clean up your data.”

This week, in episode 220, Paul Downs and Jay Goltz talk about the risks they didn’t see coming. While everyone knows there’s a risk that a business can fail because it just doesn’t work, there are lots of other, less obvious risks. These are not the risks you lose sleep over, but they’re real, and if you don’t manage them, you can expose yourself needlessly to a slew of problems. Because most people learn about these risks the hard way, Jay and Paul set out to create a top 10 list of them, but I think—for those of you keeping score at home—we actually hit 11. Which led Jay to caution: “I by no means am telling anybody, ‘Oh my God, I don't sleep at night. I'm worried about all these things.’ I'm not worried about them. I just keep an eye on them.” Wait, says Paul. That’s another one: “The risk is that you let this thing live in your head and that it destroys your ability to focus on what you should focus on.” Okay, so that makes 12. And by all means, please let us know which ones we missed.

This week, Gene Marks offers some timely tips on ways you can reduce your tax burden. As you probably know, it’s a good time to consider buying an electric vehicle or some capital equipment. But Gene also offers some less obvious suggestions. For example, if you’re looking to increase your employee compensation, there can be tax advantages to paying more of their health insurance coverage rather than giving them a raise. Also, if you own the business with a spouse, Gene explains how you might benefit from reallocating how you distribute the earnings. And of course, pay those estimated taxes on time.

This week, in episode 219, special guest Travis LeFever shares the unusual journey he and his co-founder wife, Amanda, have taken to build Mission Mobile Medical, which makes mobile health clinics in Greensboro, NC. That journey started with Travis partnering in a construction business by taking out 39 credit cards to borrow $250,000. The business did well, and he eventually bought out his partner, but when Travis’ father died unexpectedly, he was moved to sell the construction business and look for something more meaningful to do with his life. That extended search led him, somewhat improbably, to overseeing sales for a company that manufactured specialty vehicles, including the Oscar Mayer Wienermobile. It was there that Travis had another life-changing experience when a nurse with a federal grant asked if he could build a mobile clinic to reach patients in underserved communities. That was the spark that led Travis and Amanda to cash in their insurance policies and start Mission Mobile Medical in 2020. The company, whose remanufacturing process allows it to create clinics in less time and for less money than its competitors, expects to hit $60 million in revenue this year.

This week, Shawn Busse talks about something that everyone kind of knows but too few businesses emphasize: remarkable things can happen when businesses improve their workplace culture and let the world know about it. Shawn shares his approach to building a brand as an employer and explains why the payoff can easily be hundreds of thousands of dollars.

This week, in episode 218, special guest Rich Jordan tells Shawn Busse and Jay Goltz what it was like buying a small plumbing business in 2020 despite having very little experience with either plumbing or business—but having spent 10 years in the Marine Corps. “When I reflected on my time in service and what I did well and what I enjoyed,” Rich tells us, “it was when I was on a small team with high stakes, far forward, far from the flagpole, responsible for making decisions and sustaining ourselves and figuring things out. So when I thought about that—small team, high stakes, self-sustained—small business kind of fit that bill.” Not surprisingly, it took Rich some time to figure out what he was doing with the plumbing business, but in just four years, through organic growth and a few acquisitions—while taking no outside capital—he’s gone from three plumbers and $1 million in annual revenue to about 90 employees and $20 million in revenue. Which is why, Rich tells Jay and Shawn, he keeps moving the goalposts, reassessing just how big he wants the business to be.

This week, Shawn Busse walks us through his LinkedIn strategy: how often he writes, what he writes about, what he posts on his own page, what he posts on the company page, and how he promotes his business without promoting his business. Most importantly, Shawn explains why he believes his posting helps Kinesis attract both employees and clients.

This week, in Episode 270, we dig into employee ownership with two people who’ve lived it: Kris Maynard and Justin Jordan of Cathedral Holdings, a 100-percent employee-owned ESOP since 2011. Kris and Justin are enthusiastic proponents of ESOPs, but they’re also candid about what can go wrong. Yes, ESOPs come with big tax advantages. But the transaction can be complex. The debt can fundamentally change the risk profile of a business. And perhaps the most under-discussed challenge of all: not all employees embrace employee ownership. Some see it as little more than a glorified retirement plan. And here’s the thing: an ESOP can be a far riskier retirement plan than many understand. They differ from 401(k)s in that there's no regulation requiring an ESOP to sequester its employees’ retirement funds. If the company fails—and like all businesses, ESOPs do fail—those nest eggs can vanish. Kris and Justin explain how they’ve addressed these issues and what they might do differently if they were starting over. They also emphasize an important point: Not all ESOPs are created equal. “If you’ve seen one ESOP,” Justin likes to say, “you’ve seen one ESOP.”

This week, in episode 217, Laura Zander tells Shawn Busse and Jay Goltz about her approach to buying businesses. Laura says she simply recognizes that for a period of time, life will be miserable for her and for her team. That’s what happened almost a year ago when she bought two businesses that were a challenge to integrate. And now, just as things have calmed down a bit, she expects it to happen again as she eyes another acquisition. It’s also what she expects to happen as she and her husband Doug proceed with their ongoing migration to Shopify. “Our sales are going to go down,” says Laura. “SEO is going to be rough. My biggest concern, honestly, is Doug's mental health. This whole process has been so stressful for him.” Shawn, Jay, and Laura also discuss how they feel about the possibility that the 20-percent Qualified Business Income deduction could go away next year, when it’s set to expire. You might be surprised by their answers.

With the election only two weeks away, John Arensmeyer, founder and CEO of Small Business Majority, talks through what’s at stake for small businesses, including what the campaigns are saying about taxes, regulation, immigration, tariffs, and manufacturing. Plus: Given the likelihood that, regardless of who wins the White House, a closely divided federal government is likely to be with us for some time, Arensmeyer also explains what small businesses can hope for at the state and local levels.

This week, in episode 216, Shawn Busse and Jay Goltz talk about the trendy job interview strategy of trying to get beyond canned responses by asking candidates unexpected questions along the lines of, “If you were a superhero, what powers would you have and why?” Or, “What animal best represents you as a person?” Not surprisingly, Jay isn’t a big fan of those questions, and he offers an alternative strategy that features four questions of his own design. Shawn does like to ask unexpected questions, but specifically those that help him figure out whether a candidate is likely to work well with others. Plus: Shawn talks about what it was like attending the recent going-out-of-business sale of a company he had declined to take on as a client three separate times. Also, Shawn and Jay respond to a Reddit post, where a business owner asks what he can do about a large commercial client who simply refuses to pay a $40,000 bill. “Did I just learn a $40,000 lesson?” the devastated owner asks. “What now?”

This week, Gene Marks talks about the lessons business owners should take from the devastating hurricanes of recent weeks. Gene is confident that the communities will build back better than ever, but of course, not all of the businesses will make it. We’ve been reminded that disaster can strike anywhere. What should business owners do to prepare?

This week, in episode 215, Mel Gravely, Jennifer Kehrin, and Liz Picarazzi start out talking about the pain of being fired by a long-time client. “It still stings,” says Jennifer, who nonetheless surprised her team by writing a note of congratulations to the CEO of the company that took the business. The conversation moves on to the tradeoff that comes with deciding between promoting managers from within or hiring them from outside the organization: What if your people aren’t ready? What if the outsiders have more experience but aren’t as good a fit? And that leads to a discussion of how to decide when to press on with a venture that’s struggling—and when to give up on it. Not surprisingly, all three owners have some experience in this area. Of course, they also have experience with deciding when to start a business, but they have very different attitudes about risk. While Mel says he’s pretty much always ready to go, Jennifer tells us she’s been noodling on an idea she really wants to pursue for about five years.

This week, Victor Hwang talks about the remarkable road trip he recently completed in which he got a fresh perspective on the state of entrepreneurship across America. At a time when many of us are consumed with the election and politics and all of the things that divide us, Hwang, who is founder and CEO of Right to Start, a non-partisan advocacy group, met with entrepreneurs in cities and towns from Southern California, across the northern part of the country and down to Washington, D.C., and found a whole bunch of people who are working together to build things. It’s a refreshing perspective.

This week, in episode 214, we bring you another Entrepreneurial Fish Bowl with Chris Hutchinson of Trebuchet Group. As you may remember, this is a virtual exercise where we offer a business owner—or in this case a potential business owner—the opportunity to pose a challenge he or she is facing to a group of owners and entrepreneurs from the 21 Hats community as part of a brainstorming session. In this case, it was BaLeigh Waldrop who explained why she has mixed feelings about buying the Miller Waldrop furniture business that her parents own. As you’ll hear, BaLeigh has some real concerns: the business has been down of late, it’s predominantly brick-and-mortar, and she would have to work out an ownership structure with a younger brother. The 21 Hats brainstormers ask a lot of good questions, including whether the business is profitable, whether it’s been paying family members a market wage, and whether it owns the real estate. They also offer a lot of smart suggestions. Plus: it all ends with a very surprising offer from Jay Goltz.

This week, Ami Kassar, founder and CEO of MultiFunding, explains how it’s almost as if these past few years we’ve run a grand experiment to see what would happen if the government gave lots of business owners more money than they knew what to do with. In many cases, the businesses got far bigger Covid loans than they could have hoped to borrow conventionally, and they got them without having to go through the standard application process. In other words, they got the money without having to develop a plan for how they would spend it. “This is not going to end well,” says Ami.

This week, in episode 213, Paul Downs, Jaci Russo, and Sarah Segal talk about how and when they start planning for next year. And here’s one happy challenge they’ve all confronted: What do they do when they don’t have the capacity to handle all of the work that’s coming their way? Do they staff up? If so, what happens if the work subsequently falls off? Do they create a backlog? Do they miss deadlines? Do they raise prices? Plus: Jaci shares an AI tool she’s been using to learn more about the decision makers her agency targets. And the three owners respond to a case study in ADA-compliance litigation taken from a Reddit post: “What are we supposed to do about this?” a business owner who has been sued for having a non-compliant website writes in the post. “I am trying not to overreact, but having my savings and my income taken from me this way is just devastating.” Jaci, whose agency builds websites, says there is a way to protect against those lawsuits.

This week, Rob Levin, says there’s a talent crisis in America, but you wouldn't know it reading most business publications. That’s because the crisis is affecting smaller businesses much more than bigger businesses. Levin, co-founder and chairman of  WorkBetterNow, which provides remote workforce and virtual assistant services to small businesses, says he keeps hearing the same thing from owners who come to him looking for help. They just can’t find good people. Levin offers several pieces of advice that start with creating a culture that people want to be part of and then building your brand as an employer. We also talk about how he’s gotten his whole team hooked on using AI, in part through what he calls show-and-tell days.

This week, Julian Scadden explains how the organization he runs, Nexstar Network, helps the owners of plumbing, HVAC, and electrical firms become better business owners. Along the way, he discusses the challenges home-service businesses are confronting, why Nexstar is member-owned (and what that means), and an intriguing decision he made recently to part ways with the 30 percent of his members who are private-equity backed. Those members represented half the organization’s revenue at the time of the decision. I also ask Julian which is the better path: learning a trade and building a business or buying a business and figuring out the trade.

This week, in episode 212, Shawn Busse, Paul Downs, and Laura Zander call on their own experiences to assess whether the EOS operating system—as explained in Gino Wickman’s book Traction—lives up to its promise of freeing owners from frustration, helping them put the right people in the right seats, and generating all of the scale they want. Laura hired an implementer to install EOS in her business years ago. Paul took more of a do-it-yourself approach, picking and choosing from the book’s suggestions. And while Shawn hasn’t tried EOS in his own business, he has seen how it works in lots of client businesses. As a result, all three have strong opinions about what types of owners and what types of businesses are likely to do best with EOS. Laura, for example, tells us: “I think it's helpful for people like me 10 years ago, who just don't know what they're doing.”

This week, Shawn explains how a plumbing job went awry -- and more importantly, what it says about the “professionalization” of the blue-collar trades. That professionalization—along with the accompanying private equity dollars and the roll-ups and the MBAs—has certainly brought benefits. But it seems there’s been a price to pay as well.

This week, in episode 211, Jay Goltz and special guests Peter Koehler and Jimmy Kalb discuss the hottest new thing in succession planning. You may recall that earlier this year Peter was a guest on an episode in which he explained how he helped Laura Anderson sell her seafood restaurant to what’s known as an employee ownership trust or a perpetual purpose trust. Both Jay and Jimmy listened to that episode and were intrigued. Both had questions for Peter. So we recorded a conversation in which we discuss what makes a business a good candidate for trust ownership. The issues we address include: Is this only for businesses that have a save-the-world type of purpose? How much does it cost to create an ownership trust? Can owners sell to a trust and still run the business as they wish? And perhaps the biggest question of all: What can go wrong?

This week, Gene Marks tries to sort through some confusion. First, he talks about Kamala Harriss’s proposal to 10X a small business tax deduction, which sounds great except that it’s not really going to help small businesses. And then he addresses the comments of a Houston CPA who asserts that small businesses have the best tax deal in America. Gene sees it a little differently.

This week, I’m replaying an oldie but goodie, an episode that Shawn Busse and I recorded with Jeff Braverman, who turned his family’s failing retail business into a thriving ecommerce business. I’m replaying this episode both because Jeff has a great story to share, with lots of takeaways, and because—well, actually, because I took a little time off last week. But listen to this: Jeff walked away from a career as an investment banker and went to work in the family’s nut store, the Newark Nut Company. “My dad and my uncle told me I was nuts,” says Jeff, but he made them an offer they couldn’t refuse. He would put the family’s snacks online—this was way back in the early dotcom days—and they wouldn’t have to pay him unless he actually sold some nuts. As it turned out, Jeff’s little internet play wound up unleashing explosive growth and consumed the business. And despite being a former investment banker, he managed to do that without taking any outside capital. Since we first published this episode Jeff has promoted himself from Chief Nut to Chair Nut.

This week, in episode 210, Jay Goltz, Jaci Russo, and Jennifer Kerhin discuss some of the systems they’ve created that have made their businesses successful. Jay established a process that helps employees diffuse conflicts with angry customers. Jaci has a process that tracks the performance of her agency’s lead-generation efforts and has helped her target clients more precisely. And Jennifer recently created a process to deal with change orders that makes it easier to walk the line between offending customers and forfeiting profits. Plus: We follow up on some issues we’ve discussed in previous episodes. Jay told us recently that he’s cutting back on his advertising spend. Is that the best response to a softening market? Jennifer told us when she first joined the podcast about her long march through what is often called the valley of death. Is she still in the valley of death? And Jaci told us at the beginning of the year that she had two big clients that were ready to sign on. Did they in fact sign on?

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, in Episode 269, we welcome Ted Wolf, co-founder of Guidewise, as the newest regular member of the 21 Hats Podcast crew—and Ted arrives with a pretty good story. Back when he was building his IT staffing business with his brother, a senior employee walked out. But he didn’t walk out alone—he took key employees, key accounts, and 40 percent of the company’s revenue. At the time, Ted thought it was the worst day of his business life. Turns out, he says, it was his best. Because that disaster forced him to rethink everything—how decisions get made, how profits get shared, how responsibility gets distributed. And that shift led not only to healthy growth but eventually to the kind of exit business owners dream about. That experience continues to inform the work Ted does today, helping companies integrate AI into their operations. The hard part, he tells Jennifer Kerhin, isn’t the technology—it’s the people. It’s managing the change, the fear, the implications. The technology matters, too. Ted and Jennifer also discuss whether small businesses should try to retrofit AI into their current tech stacks—or whether the smarter move, painful as it may be, is to start fresh.

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.