One Rental At A Time Craig Shares 40 Year Investing Journey
Mar 6, 2026
A 40-year investing journey is unpacked through stories of early deals, moves across states, and building a 65-unit portfolio. Listeners hear why duplexes and bulk buys became a favorite strategy. Practical habits are highlighted like automated market alerts and daily scans of listing sites. There is candid talk about scaling challenges and straightforward advice for new investors.
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Four Decades Of Hands On Investing
- Craig started investing in 1987 while in college and continued through law school, buying properties with his younger brother and later a condominium.
- He scaled through the 1990s in New Jersey, sold a dozen properties in 2005, then rebuilt to 65 units by 2015 across Arizona and Pittsburgh.
Portfolio Mix And Acquisition Channels
- Craig's current portfolio includes 11 condos in Arizona and 54 units in Pittsburgh, with 19 side-by-side duplexes he favors.
- He acquired properties via bulk buys, MLS, Craigslist, and a Zillow FSBO, showing diverse sourcing.
Property Management Unlocks Scale
- Scaling requires outsourcing: managing 20 units alone cost Craig 15–20 hours weekly and stalled growth.
- Hiring a property manager unlocked his ability to grow as far as his finances allowed.