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  • Dashboard: Are We Overstating the Damage to Small Businesses?

    Dashboard: Are We Overstating the Damage to Small Businesses?
    2026/04/24
    Despite what we’ve been reading about tariffs and immigration and inflation and health insurance, the macro economy has actually held up better than many economists expected over the past year. Unemployment is low, corporate profits are high, and the stock markets have been setting records. So, this week, I put the question to John Arensmeyer, CEO and founder of Small Business Majority: Are things really that tough for small businesses? Well, yes, says John. It’s not necessarily any one issue, he says. It’s the constant drip, drip, drip of many issues. In this week’s conversation, we tackle several of the big ones.
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    24 分
  • Do Small Businesses Still Need HubSpot?

    Do Small Businesses Still Need HubSpot?
    2026/04/21
    Early on, William Vanderbloemen’s search firm was exactly the kind of business HubSpot, the marketing platform, was built to help. William had a highly specialized audience, his team produced content that his audience needed, and HubSpot helped make sure the right people found it. Back then, he tells Kate Morgan and Jaci Russo, HubSpot’s promise was that it could help a David compete with a Goliath, and that’s what it did for Vanderbloemen Search.

    But that was almost 20 years ago, long before AI began reshaping how people discover information. Now, William contends, the rules are changing. If you create strong content for a specific audience, large language models can do more and more of the work of connecting that content to the people looking for it. Which raises a question: If that’s where marketing is headed, do small businesses still need a sophisticated platform like HubSpot? In this week’s episode, William shares his doubts.

    Along the way, the three owners also discuss why Kate changed her mind about selling her business, whether companies really need to pay attention to their Glassdoor reviews, and what a plumber should tell an SEO agency that wants a monthly retainer of $12,500.
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    52 分
  • Dashboard: A Different Way to Buy Marketing

    Dashboard: A Different Way to Buy Marketing
    2026/04/17
    Hiring a full-time marketing team isn’t realistic for a lot of small businesses—but doing nothing may not be an option either. This week, Johnathan Grzybowski explains how Penji, the platform he co-founded, offers a different path: subscription-based access to vetted creatives matched to your specific needs.We talk about how that model actually works in practice, where it fits (and doesn’t) for small businesses, and how Penji manages the tension between competing with—and supporting—traditional agencies. Plus: we talk about what happens to a business like Penji as AI reshapes creative work and why Johnathan believes there’s ultimately only one marketing metric that matters: revenue.
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    35 分
  • 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?
    2026/04/14
    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 分
  • Dashboard: She Built a Business by Learning to Run Her Home

    Dashboard: She Built a Business by Learning to Run Her Home
    2026/04/10
    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 分
  • Are You Pricing for Your Clients or for Your Business?

    Are You Pricing for Your Clients or for Your Business?
    2026/04/07
    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 分
  • Dashboard: Is AI Killing SEO Spam (and Unleashing Creativity)?

    Dashboard: Is AI Killing SEO Spam (and Unleashing Creativity)?
    2026/04/03
    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 分
  • Managing People Is Hard: When Does Demanding Become Toxic?

    Managing People Is Hard: When Does Demanding Become Toxic?
    2026/03/31
    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 分