The 21 Hats Morning Report

The 21 Hats Morning Report

I’ll Just Do It Myself

If that’s your approach, says Julian Scadden, you didn’t start a business. You bought yourself a job.

Loren Feldman's avatar
Loren Feldman
Aug 10, 2026
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Good morning!

Here are today’s highlights:

  • Pia Silva explains why she’d rather do 10 projects for $3,000 than one for $30,000.

  • Alan Pentz says that the hard part isn’t getting an AI agent to work. It’s keeping it working.

  • Startups are finding opportunities creating experiential food opportunities for weddings.

  • Suddenly, the private equity business model isn’t working quite so well.

MANAGEMENT

Julian Scadden explains why it’s so tempting to keep working in—instead of on—the business: “Picture the best technician in any shop. You know this person. Maybe you are this person. They can diagnose problems by ear and never get a callback. Customers even ask for them by name. And one day, they run the math on what the company charges versus what they take home, and they say the sentence that launches half the businesses in our industry: ‘I could do this myself.’ So they do. And three years later, an alarming number of them are exhausted, underwater, and privately wondering what went wrong, because they were the best technician they knew. That’s exactly why.”

  • “When technicians ask me what they need to learn before going out on their own, they’re usually braced for one of the usual answers: Pricing. Marketing. Bookkeeping. Sales. Those matter. Every one of them. But they can also be learned on the job, bought, borrowed, or coached. You can join a network like ours and get handed decades of answers on all four. But there’s one skill nobody can hand you, and it’s the one the license exam never tests: Getting the work done through other people.”

  • “When you’re on the tools your hands are the product. Your judgment is the value. Every skill you’ve built for years has one thing in common: you, personally, delivering. Now you start a business, and the definition of excellence flips overnight. The company can never be better than what one person can do in a day, as long as that one person is doing everything. Your craftsmanship, the very thing that earned you the right to go out on your own, quietly becomes the ceiling of the whole operation.”

  • “You didn’t start a business. You bought yourself a job. Worse hours, more risk, and now the paperwork is yours too. I say this with love, because it all starts and ends with you. The good news hiding in that sentence is that the fix is also you.” READ MORE

THE 21 HATS PODCAST: DASHBOARD

The Problem with Retainers (and Other Lessons for Solopreneurs): If you’ve built a successful business, you’ve likely been told the path to more success is obvious: hire employees, land bigger clients, lock in recurring revenue with retainers. But what if those aren’t signs of progress? What if they’re traps? Pia Silva, author of Scale Solo, argues that many of the traditional rules of entrepreneurship simply don’t apply to solopreneurs. She explains why hiring too soon can derail a business, why retainers often aren’t nearly as profitable as they appear, and why she’d rather do 10 $3,000 projects than one $30,000 engagement. Along the way, Pia also tells us why she and her husband named their branding agency Worstofalldesign, why she isn’t afraid to tell clients, “You don’t get a say,” and how she’s learned to persuade clients to pay higher prices.

  • You can subscribe to the 21 Hats Podcast—brought to you by Grasshopper Bank—wherever you get podcasts.

Listen to Dashboard

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