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21 Hats Podcast

21 Hats Podcast

We Want to Grow. But at What Cost?

21 Hats Podcast · Nov 3, 2026 · 52:22

0:0052:22

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This week, Rob Levin, Liz Picarazzi, and Jaci Russo talk about what they're planning for 2027—and how much they're willing to invest to achieve their goals. Rob explains why, just days after announcing his intention to quintuple his $20 million business in three years, he decided to settle for merely tripling it. Liz is preparing to spend heavily on trade shows and salespeople as she takes Citibin national, even if it means sacrificing profitability in the short term. She's also starting to think seriously about selling the business, possibly in as little as two years. And Jaci explains why she secludes herself out of town for a week every November to think about the future of her agency.

Along the way, the three owners also discuss what they're expecting from health insurance costs in 2027, the messy secrets they'd least like a potential buyer to discover, and what employees should do when they believe their manager is making bad decisions. Plus: Liz's bear-resistant trash enclosure survives another encounter with actual bears, and Jaci reveals that she once had to undergo leadership training because she was making her direct reports cry. The episode is brought to you by Grasshopper Bank.

Show Notes:

Here’s a video of the bears attacking Liz Picarazzi’s Grizzbins.

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Episodes: 21 Hats Podcast

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