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How Cleveland Cavalier's Owner, Dan Gilbert, Got So Rich

From My First Million · Published Jul 5, 2021 · Watch on YouTube

TL;DR

Dan Gilbert’s net worth exploded from ~$6-8B to $57B in two years, making him the 21st wealthiest person in the US, despite suffering a major stroke. He built Quicken Loans into the largest US mortgage lender, owns the Cleveland Cavaliers, co-founded StockX, and controls massive Detroit real estate. His strategy combines a “dull” mortgage business with high-risk bets (Dictionary.

Key insights

  • Gilbert’s wealth surge (~6x in two years) occurred while he was recovering from a stroke; the stroke was caught in time because a doctor friend recognized symptoms on a golf course and got him to a ho
  • He started with nothing – his father owned a struggling Detroit bar, and he worked pizza delivery before discovering sales.
  • He sold his first mortgage company (Rock Financial) to Intuit for ~$90M during the dot-com boom, then bought it back for ~$20M in 2002 after the bubble burst, retaining the Quicken Loans brand even th

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