エピソード

  • Dashboard: Should You Pay $3,500 a Month for SEO?

    Dashboard: Should You Pay $3,500 a Month for SEO?
    2026/05/08
    Most business owners know they need marketing. What many don’t know is what they should be paying for it—or what they should expect in return. So when an SEO agency proposes a $3,500-a-month plan, how do you assess whether it’s a smart investment or an expensive gamble? Do you know how many new customers it would take to make that spend worthwhile? Do you even have the data to answer that question? This week, Shawn Busse says too many owners are making those decisions in the dark. He offers a practical framework to help you do the math to evaluate marketing proposals, set realistic expectations, and decide what’s worth spending—and what isn’t.
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    27 分
  • When That Big Break Just Might Break You

    When That Big Break Just Might Break You
    2026/05/05
    Every business owner looks forward to that big break—the moment that you land a big client or a major retailer, or do something that puts you on a national stage. But those opportunities don’t just reward you. They can also expose you—especially if you have to take on debt or ramp up production or do things you haven’t done before. Four years ago, when Liz Picarazzi won a high-profile installation for her trash enclosures in Times Square, it was exactly that kind of opportunity. Her enclosures were put to the test in as public and as challenging an environment as she could imagine. And, by any reasonable measure, they failed. In pursuing that opportunity, Liz took a risk that led to what she calls the worst day of her professional life. It also turned out to be, as she tells Lena McGuire, the best thing that could have happened to her business. That moment forced changes she might never have made otherwise, pushing her to innovate faster and sending her business on a very different trajectory.

    Meanwhile, Lena is dealing with a quieter version of the same problem: what it really takes to move your business forward. She knows her systems need an upgrade. She’s bought the software. But like a lot of owners, she’s stuck in the messy middle—paying for the future while still trapped in the past, with no time to bridge the gap. How do you choose between tasks that generate revenue immediately and those that will improve operations over time?
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    43 分
  • Dashboard: Bringing a Bazooka to a Wine Fight

    Dashboard: Bringing a Bazooka to a Wine Fight
    2026/05/01
    For years, the Wine School of Philadelphia and PhillyWine LLC coexisted in the genteel world of wine education. Then a trademark dispute turned that quiet coexistence into a legal battle—complete with accusations, lawsuits, and mounting costs.This week, Keith Wallace, founder of the Wine School of Philadelphia, joins me to talk about what happens when a business owner who’s tried to avoid litigation at all costs suddenly finds himself in the thick of it. He shares what the fight has actually required—financially, emotionally, and strategically—and what he wishes he had done differently before things escalated. Because one of the hardest lessons for any owner is this: you don’t have to want a legal fight to end up in one.
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    50 分
  • There’s Scope Creep Around Every Corner

    There’s Scope Creep Around Every Corner
    2026/04/28
    For Lena McGuire, scope creep really can show up around every corner. She’s in the home remodeling business. But for most owners, including Jaci Russo and Ted Wolf, projects that expand out of control can be less visible but just as hard to contain. It’s baked into the job, because every assignment comes with a built-in tradeoff: Protect your margins or protect the relationship. And especially in the early days of a business, when reputation feels like everything, that’s not much of a choice. “I was afraid to have tough conversations with people,” Ted says. “I just wanted everybody to like us.”

    Over time, systems help and boundaries get clearer. But the pressure never fully disappears. There’s always one more request, one more detail to tweak—especially when you’re thinking about the reviews and testimonials. “You want to get those nice photos at the end,” says remodeler Lena. “You want to get a referral.” This week, Lena, Jaci, and Ted talk about how their thinking on scope creep has evolved—and why it never stops being an issue.

    Plus: On the small business subreddit, an owner recently posted that he finds chasing accounts receivable so distasteful—it feels like begging—that he often puts it off and hopes for the best. “Is this just me?” he wants to know. “Or is this a common thing for small business owners?” We discuss. And Jaci explains why, even if she could get it, she wouldn’t even consider accepting a $500 million account promoting a big deal consumer brand.
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    49 分
  • 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