Profitable Civic Development
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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: 13:02AW
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.