Episodios

  • How Do You Sell HR to Owners Who Don’t Think They Need It?

    How Do You Sell HR to Owners Who Don’t Think They Need It?
    Apr 14 2026
    Sandy Kapell knows HR—just not the version most business owners live with. After years leading human resources for corporations, Sandy launched her own business, Trakehner Leadership, to bring that expertise to companies that need help. And she’s quickly found a big opportunity: Most small businesses don’t have HR departments, but they still have all the same HR challenges.

    The catch? Sandy has also realized that knowing HR isn’t the same as knowing how owners think about HR. Or how they talk about it. Or what they’re actually willing to pay for it. So for our latest 21 Hats Brainstorm, we brought in a panel of owners to help Sandy pressure test her assumptions, refine her pitch, and figure out what HR looks like in companies where, as one owner puts it, I tell everyone what the plan is, and then I say, “‘If you don't like it, talk to HR.’ And the joke is, I am HR. I am the owner.”

    Along the way, Sandy and the panelists dig into questions like: When does a business really need HR? What does good HR even look like at 10 or 20 employees? And how do you offer structure and support without sounding like the police or, even worse, like an HR person? Because what Sandy is really trying to do is to take a function most owners resist and make it something they actually want.
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    46 m
  • Dashboard: She Built a Business by Learning to Run Her Home

    Dashboard: She Built a Business by Learning to Run Her Home
    Apr 10 2026
    In her thirties, Lisa Woodruff hit a breaking point—overwhelmed, overweight, and depressed, as she puts it. So she made a radical decision: she quit her job as a school teacher and set out to get her own life in order. What started as a personal reset became a business—Organize 365—built around a simple but powerful idea: running a household isn’t all that different from running a company.In her new book, Escaping Quicksand, Lisa argues that households, like businesses, need systems, delegation, and intentional leadership. But she also makes a point that may resonate with a lot of listeners: for women especially, the stakes—and the expectations—are different. This week, Lisa explains what she’s learned about escaping overwhelm and why treating your home like a business might be the key to getting your life back.
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    33 m
  • Are You Pricing for Your Clients or for Your Business?

    Are You Pricing for Your Clients or for Your Business?
    Apr 7 2026
    Pricing a service business sounds straightforward—until you actually have to do it. How much should you charge? What’s reasonable? And what happens when “reasonable” isn’t enough to keep the business healthy? This week, Sarah Segal walks David C. Barnett and Liz Picarazzi through how she thinks about pricing her PR services—why she aims for consistency across clients and why she resists charging based on what the market will bear but insists on building in enough margin to stay profitable. It’s a balancing act between values and reality, and not always a comfortable one.

    The conversation gets into practical questions every business eventually faces: Do you raise prices a little every year, or wait until you’re forced to raise them more than just a little? Do you price based on your costs—or your customer’s perceived value? And how do you handle those conversations without damaging relationships you genuinely care about?

    Plus: Liz expects a tariff refund—but isn’t counting on it to help very much. She also explains why she’s stopped flying employees around the country for installations.
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    54 m
  • Dashboard: Is AI Killing SEO Spam (and Unleashing Creativity)?

    Dashboard: Is AI Killing SEO Spam (and Unleashing Creativity)?
    Apr 3 2026
    Shawn Busse has never been an AI evangelist. If anything, he’s been wary of the hype. But lately, his thinking has started to shift. While it’s still early, Shawn sees AI pushing marketing away from the soul-deadening world of SEO hacks and keyword stuffing—and toward something far more human: real storytelling and authentic brand building. In this week’s Dashboard, he explains what he’s seeing in his own business and with clients, and what it may mean for owners trying to figure out where to focus next.
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    35 m
  • Managing People Is Hard: When Does Demanding Become Toxic?

    Managing People Is Hard: When Does Demanding Become Toxic?
    Mar 31 2026
    It’s easy to condemn the horror stories coming out of Noma, the celebrated restaurant in Copenhagen. But this week, Jay Goltz, Jennifer Kerhin, and Ted Wolf confront a harder question: How far are the rest of us—business owners in every industry—from crossing the line? Because it’s not just restaurants. Most owners don’t set out to be abusive. They set out to build something great. And somewhere along the way, high standards can start to blur into something else. ‘I was out of control when I was in my 20s,’ Jay admits.

    So, what changed? And where did the owners land? How much command and control is actually necessary? When does pushing someone cross the line—and when does not pushing them enough become its own failure? Have you ever held onto the wrong employee too long? Or pushed the right one too hard? Jay doesn’t sugarcoat his opinion about yellers: “You’re going to tell me you’re passionate. I’m going to tell you, ‘You’re an asshole.’”

    The group digs into the trade-offs every owner faces: hiring versus managing, systems versus stars, culture versus performance. What do you do with the high performer who damages the team? Can you really coach anyone to excellence—or are there limits? And then there’s the quiet warning sign many owners ignore: Something goes wrong, and someone says, “Oh, well, everybody knows how Bob is.” That, says Jay, is when you know you’ve got a problem. This is a conversation about judgment calls—messy, human, unavoidable. Because as Jennifer puts it, “It’s really hard to manage people.”
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    50 m
  • Dashboard: A $2 Million Bet on Banana Ice Cream

    Dashboard: A $2 Million Bet on Banana Ice Cream
    Mar 27 2026
    Chris Campbell started his first business at 18 and has since built and sold companies in landscaping, construction, furniture, and marketing. After his most recent exit, he spent years searching for a business to buy—and found nothing. That dead end turned out to be an opening.Instead, Chris and a group of partners—including his wife, Emily—decided to start something from scratch. The result: a plan for Banana Daddy, a high-concept soft-serve shop built around banana ice cream that would take $2 million to open. Every experienced restaurant operator they consulted had the same reaction: Don’t do it. They did it anyway.It's less than a month in, but so far, Banana Daddy is exceeding expectations. Fueled in part by playful, slightly suggestive, but still kid-friendly marketing—”Please Lick Responsibly!”—it draws lines around the block and has even required a bouncer to manage the crowds. Along the way, the team has discovered something they didn’t expect: a surprising number of people want ice cream first thing in the morning. “It’s bananas,” says Chris. And this is only the first step in a much bigger plan.
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    39 m
  • It Took 25 Years to Get Here

    It Took 25 Years to Get Here
    Mar 24 2026
    Given everything going on in the world, you might expect a rough start to the year. But for Paul Downs, Jennifer Kerhin, and Jaci Russo, 2026 has actually begun quite well. In fact, Jennifer and Jaci say they’re finally climbing out of what many owners call the Valley of Death—that long stretch when the business depends on you for everything and when it starts to outgrow your people and your systems. Exiting the valley can take a lot longer than people expect. Jennifer is seeing daylight in year 17. Paul says it took him 25 years, a quarter of a century. “Most of that time,” he admits, “I was just wallowing in ignorance.” One lesson they’ve learned the hard way: growing too fast can do real damage. “You burn out your employees,” Jennifer says. “You provide poor quality control to your clients. You make everybody upset and angry.”

    Along the way, the three owners cover a lot of ground: what actually makes trade shows worth the investment (hint: it’s what you do before and after), why you may not be able to copyright that graphic design, why your logo needs a trademark, why Paul’s Google traffic is holding up but his Middle East expansion is on hold, what Jaci has uncovered about the shocking cost gap in health insurance for her female employees, and why it’s insane that business owners have to manage their employees’ health insurance in the first place. It’s a wide-ranging conversation—but underneath it all is a theme most owners will recognize: Progress doesn’t always come from big breakthroughs. Sometimes it comes from surviving long enough to figure things out.
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    50 m
  • Dashboard: The Case Against Pay for Performance

    Dashboard: The Case Against Pay for Performance
    Mar 20 2026
    For most business owners, rewarding employees for doing their jobs well is just common sense. Hit your numbers, get a bonus. Sell more, earn more. Perform better, get paid more. That’s how motivation works…right?This week, management consultant Kelly Allan asks owners to reconsider that assumption. Allan is steeped in the teachings of W. Edwards Deming, the management thinker widely credited with inspiring Japan’s post–World War II industrial revival. Deming argued that pay-for-performance systems don’t actually improve performance. Instead, they create unintended consequences—encouraging people to chase metrics, compete with colleagues, and optimize the wrong things.In Deming’s view—and in Allan’s—performance isn’t primarily about individuals at all. It’s about the system they work in. In our conversation, Kelly explains why incentives often backfire and how owners who are curious can begin experimenting with a different approach.
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    45 m