21 Hats Podcast
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Dashboard: Helping Creatives with the Business of Art
For years, Kim Robinson worked on the brand side, helping major companies connect with artists and creatives. Eventually, he decided he’d rather be working for the artists themselves. So he launched…
Would You Rather Risk Losing a Client or an Employee?
This week, Sarah Segal, Jaci Russo, and Lena McGuire tackle a question many service business owners face: Which is the bigger risk—an employee who feels overburdened or a client who feels neglected?…
Dashboard: A Buyer That Doesn’t Want to Flip Your Business
Sean Joy is head of M&A at Chenmark, a Portland, Maine-based holding company that acquires a handful of small businesses each year. At first glance, Chenmark may sound like a traditional private…
‘I’m Skeptical AI Is Going to Help Us’
This week, we explore some contrasting opinions about artificial intelligence. Paul Downs has serious doubts that AI will ever have a significant impact on his business. Paul, who builds custom…
Dashboard: Uber for Landscapers
When Bryan Clayton graduated from college, he discovered he had two options: take an entry-level job and a pay cut—or go back to mowing lawns, which was already making him more money. He chose the…
In Search of Companies More Interested in Being Great Than Big
Twenty years ago, Bo Burlingham gave a name to a feeling a lot of business owners had struggled to articulate. In his book Small Giants, Bo profiled companies that had chosen not to chase growth at…
Dashboard: Is It Still Worth Selling on Amazon?
When Eugene Khayman first got involved with Million Dollar Sellers, it was essentially a support group for entrepreneurs building businesses on Amazon. Back then, the opportunity seemed almost…
When Employee Violence Walks Through Your Door
Michelle Wyatt has replayed the events in her mind countless times, looking for warning signs she might have missed. But even now, she can’t find any. Both employees had passed background checks and…
Dashboard: A Marketplace for Ethical Exits
Hannah Sandmeyer spent years acquiring ecommerce businesses for an Amazon aggregator, giving her a front-row seat to how deals get done—and what often gets lost in the process. Too many owners, she…
The Real Payoff May Be in Owning, Not Selling
When Kate Morgan started thinking seriously about selling her business, she assumed the big payoff would come at closing. But as she tells David C. Barnett and Paul Downs this week, she’s come to…
Dashboard: Should You Pay $3,500 a Month for SEO?
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,…
When That Big Break Just Might Break You
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…
Dashboard: Bringing a Bazooka to a Wine Fight
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…
There’s Scope Creep Around Every Corner
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…
Dashboard: Are We Overstating the Damage to Small Businesses?
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.…
Do Small Businesses Still Need HubSpot?
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…
Dashboard: A Different Way to Buy Marketing
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…
How Do You Sell HR to Owners Who Don’t Think They Need It?
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…
Dashboard: She Built a Business by Learning to Run Her Home
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…
Are You Pricing for Your Clients or for Your Business?
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…
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21 Hats Podcast has published 541 episodes since January 2020, covering topics in Business, Business News.
21 Hats Podcast is currently highly active with new episodes every few days. Average episode length is 38m.
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