21 Hats Podcast Do You Have the Stomach for This? 2025 in Review, Part 2
Dec 30, 2025
Laura Zander, a serial entrepreneur and founder of Jimmy Beans Wool, shares insights on successful exit planning and the nuances of valuation during her sale. Jackie Russo, a marketing agency founder, discusses the lessons learned from a high-priced sales hire that didn't pan out and her innovative AI systems delivering daily leads. Liz Piccarazzi, of CityBin, recounts her intense journey developing bear-resistant bins, highlighted by a close encounter with a grizzly. Mel Gravely talks about shutting down his profitable business due to partner conflicts and personal strains.
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Preparing To Be Bought Over Years
- Laura Zander quietly cultivated buyer relationships for years before selling Jimmy Beans Wool.
- She knew her target valuation and accepted an offer that matched her price without a formal appraisal.
Set A Firm Price And Protective Terms
- Set a clear price target and be willing to walk away so you can negotiate from strength.
- Structure the deal to protect yourself if the world collapses, prioritizing terms you can live with.
When A Big Hire Unravels Fast
- Jackie Russo hired a high-priced salesperson who initially impressed but then rapidly declined.
- The placement firm offered to redo the search at no charge after the hire resigned unexpectedly.