From Flipping Duplexes to a $100M+ Portfolio: Will Matheson’s Multifamily Journey

In this episode, Will Matheson of Matheson Capital shares how he went from brokering deals to building a $100M+ multifamily portfolio across the Southeast. He walks us through his first debt deal, the challenges of navigating COVID-era operations, and the keys to scaling profitably while protecting investor capital.

 

Will also discusses lessons from early mistakes, how his team achieved an average 47% IRR across 16 acquisitions, and what’s next as Matheson Capital pursues new opportunities in build-to-rent communities and beyond.

 

Key Takeaways:
• From Brokers to Buyers: Will and his twin brother Evan started as brokers, but quickly shifted gears and raised capital themselves for a $1M hard money loan—kickstarting their investing journey.
• First Investment Win: A quick flip on a Los Angeles duplex netted them $185K in profit, building confidence and momentum.
• Lessons from the Worst Deal: Greenwood Village Townhomes faced COVID-related rent collection issues and crime. Despite the hurdles, the team still returned investor capital with a small gain.
• Best Deal Breakdown: Timberstone Townhomes delivered an 80% return on equity thanks to strong operations, solid debt, and zero prepayment penalties.
• Smart Scaling Strategies: Matheson Capital now focuses on larger, more standardized multifamily assets with third-party management, prioritizing cash flow and operational efficiency.
• What’s Next: Will shares details about their latest BTR acquisition in Tuscaloosa and what they’re targeting next in the Southeast.

 

How to contact Will:
• Matheson Capital: mathcap.com
• Will Matheson on LinkedIn: https://www.linkedin.com/in/will-matheson/

 

How to contact Brad:
• Risk Strategies on LinkedIn: https://www.linkedin.com/company/risk-strategies-company/posts/?feedView=all
• Brad on LinkedIn: https://www.linkedin.com/in/brad-weaver-bb29035/
• Book an intro appt with Brad: https://zcal.co/fwbn/introcall
• Brad’s Direct Cell: (845) 779-2044