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This week, in Episode 253, Paul Downs tells Kate Morgan and Liz PIcarazzi that he recently posted a job on Indeed and got 153 resumes—more than he’s ever gotten before, which prompted some interesting questions: What does this mean for business owners? Should a job posting be more about what the company expects from a candidate or more about what the company has to offer? Do the owners ask candidates to take personality tests? If the owners get 150 resumes, do they ask ChatGPT to review them? And doesn’t it seem as if more people are looking to switch careers? “When I look at someone who's working as a graphic designer in an ad agency,” Paul tells us, “I'm thinking: This person realizes AI is coming for their job.” Plus: Liz gives us a surprisingly upbeat update on her tariff situation. And the owners respond to a Reddit post asking whether it would be crazy to start a business in the current economic environment. Paul’s response: “Don’t do it.”
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This week, Tracy Bech, co-author of “The 60-Minute CFO,” tells us that she normally recommends that business owners check 14 performance measures on a regular basis. But during uncertain times like these, Tracy says, there are three in particular to keep an eye on: gross profit margin, operating cash flow, and current ratio. In our conversation, she explains how they work, what they mean, and what to do if they’re flashing red. She also says you can download a free tool to track your cash flow at 60minutecfo.com.
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This week, in Episode 252, David Barnett, Mel Gravely, and Kate Morgan discuss a somewhat unusual approach to succession, which is to not sell the business. Basically, it’s about taking a step back from leadership while maintaining ownership, and both Kate and especially Mel are moving in this direction. The approach can pay off financially in part because businesses often are worth more to the owner than they would be to a buyer. Why is that? As David explains, the business that the buyer buys isn’t really the same business that the owner sells: “If you've owned the business for a long time,” he says, “the balance sheet is probably pretty strong. You've had time to earn money, pay down debts. You’ve got a good equity position. This makes the business strong, and it makes it better able to weather storms. If I were to come along and buy Mel's business, I would come together on a price, and I would pay Mel. But a good chunk of that money would probably be borrowed. Now, I would have a much weaker balance sheet than what Mel enjoys today. And a big chunk of the cash flow that he currently enjoys, I would end up giving to my bank.” Of course, this approach to succession does have some challenging elements, including finding someone to run the business. Plus: We also discuss whether it’s possible to sell a solopreneur business.
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This week, Gene Marks tells us why he’s skeptical of corporate CEOs like Amazon’s Andy Jassy who have started telling employees that they are likely to lose their jobs as the company continues to adopt tools that use artificial intelligence. Gene thinks CEOs who blame AI for corporate layoffs are really covering for bad management. In fact, he thinks anyone who is already replacing employees with AI is a fool. On the other hand, Gene tells us he’s incorporating AI tools into almost every aspect of his business, and he gives us some examples.
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This week, in episode 251, we meet Dan Carmody, who has gained an unusual perspective on what it takes to build a business in the United States. Dan has started and built his own businesses. He’s run community development organizations that have worked to support the growth of other local businesses. And until January, he was CEO of the Eastern Market in Detroit, which is one of the last great public markets in the country and has seen a remarkable number of businesses start, thrive, and even go national. On top of that, he’s also traveled to other countries to see how they support small enterprises. His conclusion? We’re doing it wrong. This may seem jarring given the story we like to tell ourselves about the American Dream, but as Dan explains, there are some things we could learn from other countries.
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This week, Victor Hwang tells us that his organization, Right to Start, has big plans for America’s upcoming 250th birthday. Spurred largely by the widespread sense that the American Dream has lost some of its luster, Victor and Right to Start are launching a campaign to turn our semiquincentennial into a celebration of America’s entrepreneurial roots and a push to remove the barriers that make it harder than it should be to start and build a business. One key focus: finding ways to make it easier for businesses to raise capital. You can learn more here.
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This week, in episode 250, we’re joined by special guest Alan Pentz, who recently stepped back from his government-contracting business to start the Owner Institute, which draws on lessons he learned the hard way to help business owners scale their businesses. In his new role, Alan has immersed himself in the world of generative AI, and he’s come to some intriguing conclusions, one of which is that AI will eliminate most B-to-B agencies—marketing agencies, public relations agencies, professional services firms. Why is that? Because, Alan says, businesses will no longer be willing to pay agencies retainers of $5,000 or $10,000 a month once they realize they can get similar or even superior work from an AI chatbot. “In general,” Alan says, “most technology waves end up with a few big winners, and most people are just roadkill.” To explore the theory that agencies are likely to be roadkill, we invited Jaci Russo, owner of a marketing agency, and Sarah Segal, owner of a public relations agency, to have a conversation with Alan. Spoiler alert: There were no tears, no threats, and no insults.
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On the one hand, Gene Marks tells us this week that the GOP tax bill that has passed the House and is being debated in the Senate contains a lot of elements that should cheer business owners. Specifically, the pass-through deduction would get extended and increased, the capital-equipment deduction would go back to being 100-percent deductible in the first year, and the research-and-development deduction would also go back to being fully deductible in the first year. On the other hand, Gene believes the Big Beautiful Bill is going to be a big ugly problem for business owners. But I’ll let him explain.
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This week, in Episode 249, we bring you a conversation recorded at our recent 21 Hats Live event in Ann Arbor, Michigan, with Ari Weinzweig, co-founder of one of America’s most influential small businesses. Starting 43 years ago with a highly successful college town delicatessen that they could have replicated all over the country (including for Disney), Ari and co-founder Paul Saginaw have instead built Zingerman’s Community of Businesses, a collection of 12 Ann Arbor-based, collaboratively run businesses each with its own leadership and ownership structure. Together, these businesses produce $80 million a year in revenue. They include a bakery; a coffee company; two event spaces; a roadhouse; a Korean restaurant; a mail-order operation; an international food-tour business; a publishing house that publishes, among others, Ari Weinzweig; and a training center—ZingTrain—that has shared the Zingerman’s approach to business building with more than 10,000 businesses.
In 2003, Bo Burlingham pronounced Zingerman’s “The Coolest Small Company in America.” Bo’s article became the foundation of Small Giants, his book about companies that are more intent on being great than being big. The last thing we did at 21 Hats Live was to sit down with Ari to talk about that philosophy. In his passionate responses to our many questions—responses, I should note, that include a few F-bombs—Ari explains how the Zingerman’s team decides whether to start a new business, how he and Paul made (and re-made) an especially difficult decision about expanding, how he and Paul have managed to sustain their partnership for more than four decades, how they chose a succession plan, how they know if they’re charging enough, why for many years Ari’s mother continued to believe he was a failure, and a whole lot more. -
This week, Sahra Halpern, who is CEO of the Business Consortium Fund, talks about a type of lender that is not particularly well known or well understood even among business owners. The Business Consortium Fund is a CDFI, or community development financial institution. Traditionally, many CDFIs, including Halpern’s, have sought to serve underrepresented business owners who have struggled to get a traditional bank loan. In the current political climate, however, CDFIs are looking to reach a broader audience. In our conversation, Halpern talks about how CDFI lending differs from bank lending and what types of business should consider approaching a CDFI.
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This week, in Episode 248, we bring you a taste of what we experienced at the recent 21 Hats Live event in Ann Arbor, where we did a deep dive into a challenge confronting Mars Chapman, owner of Casey’s New Orleans Snowballs, a snowcone business in Austin, Texas. Mars, who is 36, bought the business from his parents and also inherited from them a somewhat laidback approach to ownership. The business has been operating for 29 years, but it has generally run only eight months of the year, which has been enough, thus far, to support a comfortable lifestyle for its owners. But Mars, whose wife, Page, works for a nonprofit and who is pregnant with their first child, has begun to question whether his current approach will be enough to support a family. This is another in our series of 21 Hats Brainstorms—we used to call them Fish Bowls—in which we pair an owner facing a challenge with a group of entrepreneurs eager to help. We ask questions, break into small groups to exchange ideas, and then report back. Sometimes—as I personally experienced at last year’s 21 Hats Live event—the comments and suggestions can be challenging, even a little painful to hear. But they’re always constructive.
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This week, Lance Tyson, founder of the Tyson Group sales consultancy, talks about how he’s using generative AI in his own business along with his suggestions for owners who are just getting started with AI. Among his suggestions: ask ChatGPT how best to use ChatGpt. Lance also talks about how salespeople can best navigate a business environment struggling with tariffs, uncertainty, rising prices, and talk of recession. One tip: don’t just accept an email rejection. Try to get them on the phone.
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This week, in Episode 247, we welcome a new regular, Kate Morgan, who joins the podcast along with Paul Downs and Jay Goltz. Kate is the CEO and founder of Boston Human Capital Partners, which provides recruiting and HR services, mostly to other small businesses. After a very difficult stretch caused by the pandemic, Kate’s business has been growing again – but Paul and Jay think she’s leaving money on the table. They think she needs to raise her prices. “I mean,” responds Kate, “we're growing in an industry that we're seeing shrinking right now, and so it's one of these things: Do I want to scare the squirrels and jump up our prices? That's where I've been struggling.” Plus: Are HR people supposed to protect the employees or the business? And after having to lay off a third of his workforce, Paul gives us an encouraging update on how his business is doing.
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This week, John Arensmeyer, our man in Washington, reports on what small business owners need and what they are likely to get from Republicans and Democrats. The issues -- tariffs, access to capital, taxes, health care -- are tricky, but John says there have been some recent examples of legislators coming together to support small businesses.
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This week, in Episode 246, we meet Ben Knepler, who, along with his True Places co-founder Nelson Warley, came up with an idea for an outdoor chair that they believe could be a game-changer. They liked the idea so much that they quit their corporate jobs, they raised money, they borrowed money—putting their own homes at risk—they fought through the pandemic, they found a manufacturer in China, they launched on Kickstarter, they found another manufacturer in Cambodia, and then they ran smack into the brick wall of President Trump’s second-term tariffs. Or, as George Harrison almost put it, “If you try to sit, I’ll tax your … sturdy, portable, folding chair that could create a whole new category of high-end outdoor products except you’ll probably have to try to sell them in some other country … ‘cause I’m the tariff man.”
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This week, Gene Marks -- normally a fan of automating anything that can be automated — says it’s too soon to think about turning important tasks over to artificial intelligence bots, mostly because they’re still making too many mistakes. In fact, Gene cites a survey of business leaders who said they came to regret offloading employees in favor of AI. In many cases, those leaders wound up trying to re-hire their employees. Plus: Gene also talks about how businesses using AI can get into regulatory trouble if they’re not careful.
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This week, in Episode 245, a new regular, David Barnett, joins the podcast along with Jaci Russo and William Vanderbloemen. David, who has been a guest on the podcast before, helps people buy and sell businesses—but, as he explains, he’s not a business broker. He’s found a different business model. David, Jaci, and William discuss why it’s so hard to sell a business, what owners can do to make their businesses more attractive to buyers, and why it can be in everyone’s interest for sellers to accept an earnout. Plus: Jaci talks about why she used a recruiter to help her hire a business development person and why she ended up choosing someone who checked none of the boxes she initially thought most important. “I thought I needed some hotshot East Coast, West Coast, big city dude who came in with all the slick talk,” she tells us. Instead, she found her winner in rural Alabama.
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This week, Rob Levin, co-founder and chairman of WorkBetterNow, talks about why he sees business owners—despite the uncertain economy—still struggling to fill key roles. He also discusses the importance of creating a culture by design, how owners can manage their profiles on Glassdoor, and what he thinks of Gen Z employees. Plus: Rob explains how he’s been infusing AI into all aspects of running his business.
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This week, in Episode 244, Jennifer Kerhin, Jaci Russo, and Sarah Segal talk about how they’ve been using ChatGPT. Jennifer has deputized the AI chatbot as a key advisor, feeding it all kinds of performance data and soliciting its analysis before making hiring, financial, and strategic decisions. Recently, she asked it to identify her biggest blind spots as a CEO. Five seconds later, it spat out five answers with detailed explanations and suggestions. And what did Jennifer think of the feedback? “It was right on,” she tells us. “I mean, it was totally, absolutely true.” We even brought ChatGPT into our conversation in real time, asking it whether Jaci had hired the right business development person, whether Sarah had been fully prepared two years ago to buy back her PR firm, and what’s the best podcast for small business owners. Plus: while we were talking, Jaci asked ChatGPT to evaluate the performance of her co-founder and spouse, MIchael. Let’s just say, it does have some concerns.
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This week, Gene Marks highlights some recent tech developments, including: Quickbooks is selling a lifetime version of its software for just $250. Microsoft has reintroduced its somewhat controversial Recall AI tool, which captures and indexes screenshots of user activity every three seconds—a function that is intended to improve cybersecurity but that has raised some interesting questions. Plus: Gene explains how—if you have the time and money—you can now connect the various software platforms you use and turn them into a smart AI assistant.
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