In The Trenches

Facing the Worst-Case Scenario: How Jed Morris Lost His Business and Rebuilt His Life

Nov 27, 2025
Jed Morris, an entrepreneur who endured a business bankruptcy and rebuilt his life, shares hard-won perspective. He covers risky friends-and-family funding, why roll-ups can fail, cultural and cash-flow traps, and the fallout of personal guarantees. Short, candid stories trace his collapse, recovery, and how he now advises others to avoid the same mistakes.
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ADVICE

Bigger Acquisitions Lower Risk

  • Go as big as you can within your financing capacity because larger businesses reduce risk.
  • Larger deals typically have better cash flow, customers, and organizational resilience than very small ones.
ADVICE

Don't Buy Distressed Businesses Early

  • Avoid buying distressed turnarounds as a first-time buyer; you lack the experience and runway.
  • Bring more equity, accept lower ownership, and target strong businesses to reduce bankruptcy risk.
INSIGHT

Treat Organic Growth As The Baseline

  • Let organic growth be the baseline before assuming M&A will deliver returns.
  • Relying on roll-ups as a core assumption inflates capital needs and execution risk.
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