Best Real Estate Investing Advice Ever With Joe Fairless

On this episode of Next Level CRE, Matt Faircloth interviews Jonathan Twombly, a former Wall Street lawyer turned real estate investor and boutique hotel redeveloper. They dive into the value of mastermind groups, highlighting how peer accountability, vulnerability, and structure have supported their decade-long growth in the CRE space. Jonathan shares the story of how he exited a 400-unit multifamily portfolio in South Carolina at the peak of the market, pivoting into underperforming hotel assets in overlooked markets like upstate New York. He details his hands-on repositioning strategy, challenges of retraining the market after a hotel renovation, and why legacy hotel owners are one of the best untapped seller demographics today. Jonathan Twombly Current role: Founder of Two Bridges Asset Management; Partner in boutique hotel syndications Based in: Brooklyn, New York Say hi to them at: LinkedIn or visit Apartment Investors Club at apartmentinvestorsclub.com Visit investwithsunrise.