In this episode, I sit down with Will Matheson, co-founder of Matheson Capital, to unpack how he and his twin brother scaled from buying duplexes in their mid-20s to operating a growing multifamily platform across the Southeast. Will shares the early mistakes they made, how their underwriting dramatically improved after 2020, and why they originally pitched investors on short-term holds with a simple message: “Date me, don’t marry me.”

We dive into sourcing deals through brokers, building investor relationships in unconventional ways (yes, even dating apps), and why fixed-rate debt has been their anchor through market volatility. If you’re navigating today’s distress cycle or thinking about how to scale responsibly in multifamily, this episode is a masterclass in discipline, market selection, and capital strategy.

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Episode Highlights

[0:00] – Will’s transition from Marcus & Millichap broker to multifamily owner

[3:26] – Leaving brokerage to earn a Master’s in Real Estate Development at Columbia

[4:20] – Flipping their first deal in two months with a 400% IRR

[9:07] – Why starting small (2–32 units) built long-term confidence

[12:16] – The “date me, don’t marry me” 1–3 year hold strategy

[15:02] – Why proven value-add beats reinventing the wheel

[16:49] – Why Will loves working with brokers instead of cold calling owners

[18:31] – Choosing Southeastern markets with growth and barriers to entry

[20:41] – Buying build-to-rent in Alabama at $100 per square foot

[23:44] – Raising capital through LinkedIn, referrals, cold calls—even dating apps

[24:31] – Selling most of their portfolio before the rate spike

[27:02] – Why fixed-rate debt is non-negotiable at Matheson Capital

[29:12] – Supply pressure in Charlotte vs. insulated micro-markets

[33:18] – Targeting $1B AUM while staying disciplined

[34:33] – Capital stack distress creating today’s buying opportunities

[35:48] – Why insurance hasn’t hurt them the way it has others

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5 Key Takeaways

1. Early mistakes are tuition—small deals create room to improve your process.

2. Fixed-rate debt provides stability when rates and capital markets shift.

3. Proven value-add strategies reduce downside risk.

4. Distress today is mostly in the capital stack—not necessarily at the property level.

5. Investor relationships can come from anywhere—consistency beats perfection.

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Links & Resources

• Matheson Capital – https://www.mathcap.com

• Connect with Will Matheson on LinkedIn

• Mentioned Topics: Fixed-rate debt, loan assumptions, build-to-rent (BTR), Southeastern multifamily markets, capital stack distress, value-add underwriting

If you enjoyed this conversation on scaling responsibly, navigating distress, and building a multifamily platform the disciplined way, make sure to follow, rate, review, and share the show—it helps us reach more investors serious about long-term growth.