The 21 Hats Morning Report

The 21 Hats Morning Report

Do You Want to Serve Clients—or Build a Business?

In our latest podcast, the owners talk about some tricky decisions that owners are forced to confront.

Loren Feldman's avatar
Loren Feldman
Oct 21, 2025
∙ Paid

Good Morning!

Here are today’s highlights:

  • For many businesses, the shutdown couldn’t have come at a worse time.

  • After Walmart’s deal with ChatGPT, ecommerce websites may never be the same.

  • A family farm is getting squeezed from all directions.

  • In Chicago, cyclists are trying to protect street vendors from ICE.

THE 21 HATS PODCAST

This week, David C. Barnett, Kate Morgan, and Sarah Segal tackle a challenge every owner who sells services eventually faces: Clients want to hire you, but you want them to understand they’ll mostly be working with your team. How do you make that clear without scaring them off? For some, it’s a delicate balancing act. For Kate, it’s simple: if a client insists on her personal time, she charges, in her words, “a boatload of cash.”

  • Plus: we dive into another tricky owner decision: how to structure bonus plans that truly drive retention. David is weighing a deferred-bonus approach, where payouts happen over several years. It’s a proven way to keep people around, but he wonders: Do you really want employees who’d otherwise leave to stay just for the money?

  • Also, when valued employees get an offer, do you counteroffer? And if they leave, do you tell them they can always come back?

  • You can subscribe to the 21 Hats Podcast wherever you get podcasts.

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