Key Takeaways:

Chicago’s 2008 parking meter deal resulted in lost long-term revenue for the city, with investors earning profits and retaining rights for decades.

Monroe Carroll, Sr.’s initiative to monetize underused railroad land in the 1950s evolved into Central Parking, benefiting from legal requirements and the car boom.

The parking lot industry grew due to high operating margins, captive demand, and minimal maintenance, drawing attention from Wall Street and institutional investors.

The business model has expanded into industrial outdoor storage, supported by trends like e-commerce growth and infrastructure investment, resulting in surging demand and rental rates.

Operators have adapted to changes such as ride-sharing and eliminated parking minimums by introducing new uses: EV charging hubs, multi-purpose lots, and last-mile logistics.

The enduring insight: overlooked, low-competition “boring” businesses (like parking lots and storage yards) can offer stable, significant long-term returns for savvy investors.