John Todderud's Journey from Tech to Multifamily Syndication

About this episode

John Todderud shares his journey from tech professional to multifamily real estate syndicator, discussing key lessons learned along the way.

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…

People in this episode

Host: Brad Weaver

Guest: John Todderud

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
• The harsh lesson of underestimating deferred maintenance
• 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
• The current market and why patience is crucial for finding the right deals
• The value of building trust and relationships with investors

Keywords

• multifamily real estate
• syndication
• investor relationships
• deferred maintenance
• recession-resistant market

Mentioned in this episode

Products: Cardinal Oak Investments

More episodes of First, Worst, Best, & Next

• Tyler Chesser's Playbook: Achieving $2.1M Exits and $150M Targets in a Volatile Market · October 27, 2025 · 46 min
• John Casmon on 'Failing Forward' and the Power of Midwest Real Estate · October 24, 2025 · 1h 5m
• John Wijtenburg on Transforming a $100M Resort and the CRE Growth Operating System · October 3, 2025 · 29 min
• Beyond the First Deal: Scaling a Real Estate Portfolio with Ian Cruz · September 12, 2025 · 34 min
• Bruce Fraser on Distressed Multifamily and Macro Investing · September 5, 2025 · 44 min
• From Cybersecurity to $217M in Real Estate: Tenny Tolafari's Journey · September 3, 2025 · 29 min