Profitable Civic Development

Dan Gilbert built a multi-billion dollar empire through Quicken Loans while simultaneously working to revitalize Detroit. Here's how he operates.

Core Business Success

  • Built Quicken Loans into largest home mortgage lender in US
    • Started as Rock Financial in 1985 with his brother
    • Sold to Intuit in 1997 for ~$90M
    • Bought back in 2002 for ~$20M
    • Took public recently with 85-90% ownership
    • Current market cap of $46B

Investment Philosophy

  • Takes big risks on diverse ventures
  • Says "yes before no" to new opportunities
  • Maintains a "barbell" approach:
    • Core business: Stable mortgage lending
    • Venture investments: High-risk, innovative bets

Portfolio Highlights

  • Sports & Entertainment
    • Cleveland Cavaliers (NBA team)
    • Previously owned casinos
  • Digital & Media
    • Dictionary.com and Thesaurus.com
    • Robb Report
    • StockX (sneaker/watch marketplace)
  • Retail & Consumer
    • Shinola (watches and hotel)
  • Venture Capital
    • Largest LP in Ludlow Ventures
    • Own venture fund
    • Multiple tech investments

Detroit Revitalization Efforts

  • Moved 4,000 employees to downtown Detroit
  • Invested billions in real estate
    • Owns 20-30% of downtown Detroit
    • Purchased numerous derelict buildings
  • Created private security force for the city
  • Committed $300M to pay resident property taxes
  • Built infrastructure including casinos and hotels

Personal Characteristics

  • Family-focused with 5 children
  • Philanthropic interests
    • Funds research for rare diseases
    • Focuses on hometown development
  • Accessible and engaged leader
    • Responds personally to cold emails
    • Spends time with people he finds interesting
  • Makes decisions based on interest rather than pure ROI
02:03 - 02:17
Full video: 13:02
AW

Andrew Wilkinson

Co-founder of Tiny

Wilkinson is the co-founder of Tiny Capital, which owns companies including AeroPress, MetaLab and Dribble. He is also the co-founder and chairman of WeCommerce, a holding company that starts, buys, and invests in the world’s top Shopify businesses.

TwitterLinkedIn
Founder
Author
Investor