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September 24, 2025 • 31 mins

In this episode, Brad chats with John Todderud, the founder of Cardinal Oak Investments and a former tech professional who transitioned into multifamily real estate. John shares his journey from buying small, rural properties to scaling a full-fledged syndication business. He opens up about the biggest lessons he learned from his "worst" and "best" deals, including the pitfalls of underestimating deferred maintenance and the unexpected rewards of a long-term hold in a stable market. John also discusses his shift from individual ownership to syndication, highlighting the value of building relationships and leveraging investor capital to acquire larger assets.

Key Topics Covered:

  • John's path from a tech career to full-time real estate investor.

  • The evolution of Cardinal Oak Investments from a personal vehicle to a syndication business.

  • The importance of starting small and learning from mistakes, as with his first three-unit deal.

  • The harsh lesson of underestimating deferred maintenance on a big value-add project.

  • Why a "slow and steady" deal in a recession-resistant market turned into a "home run".

  • The key differences between a joint venture and a syndication, and why he chose the latter.

  • The current market and why patience is crucial for finding the right deals.

  • The value of building trust and relationships with investors as a syndicator.

đź’¬ Memorable Quotes:

  • “I wanted a property that I could… learn on, essentially to make my mistakes, my small mistakes.” — John Todderud

  • “It's not like you fix the roof and suddenly you can get higher rents... a lot of these things don't translate directly into income, but they do mean a buyer... has fewer things to choke on.” — John Todderud

  • “I never would have expected it... just a huge pleasant surprise.” — John Todderud on his "home run" deal

đź”— Connect with John Todderud:

🎙️ Connect with Host Brad Weaver:

 

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