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: [phone]