JF 3991: Multifamily Burnout, Hotel Goldmines, and the Power of Saying “Somebody Should…” ft. Jonathan Twombly

Aug 8, 2025

Jonathan Twombly, a former Wall Street lawyer turned successful real estate investor, shares his insights on navigating the multifamily and hotel markets. He discusses his exit from a large multifamily portfolio at its peak, pivoting to revitalizing underperforming hotels in overlooked areas. Jonathan emphasizes the immense benefits of mastermind groups for accountability and growth. He also highlights untapped opportunities in legacy hotel ownership, the challenges of repositioning properties, and the complexities of financing non-branded hotel assets.

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ADVICE

Mastermind Group Success Factors

Join a committed mastermind group that meets regularly with a clear agenda.
Ensure confidentiality and vulnerability to gain valuable advice and peer accountability.

ANECDOTE

Exiting South Carolina Multifamily Portfolio

Jonathan sold his 400-unit South Carolina multifamily portfolio in 2019 due to a high offer and difficulty finding new good deals.
The portfolio included 4 properties compacted within a 45-minute drive, averaging about 100 units each.

INSIGHT

Invest in Undervalued Markets

Undervalued markets with flat or negative growth often offer better investment opportunities.
They have obsolete supply with little new construction, reducing overbuilding risk.

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