Thomas Castelli, Partner at Hall CPA and former syndicator and multifamily investor, shares firsthand tales from closing deals, weathering hurricane due diligence, and exiting during COVID. He talks about capital raising mistakes, the importance of investor relationships, underwriting and submarket analysis, insurance risks in hurricane zones, and how a failed fund shaped his approach to syndications.
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question_answer ANECDOTE
First GP Deal Through Hurricane and COVID
Thomas Castelli described his first GP experience on an 82-unit Jacksonville apartment bought in November 2017.
He walked units during Hurricane Irma due diligence, led negotiations, executed value-add renovations, and exited during COVID with a delayed close in May 2020.
volunteer_activism ADVICE
Raise Capital Before You Find A Deal
Do build investor relationships before you find a deal so you can raise capital quickly when a deal appears.
Thomas warns that finding a deal first led them to bring a crowdfunding partner who took promote and fees, reducing sponsor economics.
volunteer_activism ADVICE
Use Network First Then Marketing For Fundraising
Do start with your own network and potential partners when raising capital, then scale using marketing and investor communities.
Thomas recommends partnering with capital-rich people, joining vetted communities (e.g., PassivePockets), and creating thought leadership like podcasts or newsletters.
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In this episode of the Major League Real Estate Podcast, Thomas Castelli shares the full story of his journey, from attending local RIAs and investing as an LP, to joining the GP team on an 82-unit apartment complex, navigating hurricane due diligence, raising capital under pressure, and exiting during the chaos of COVID in 2020.
But that’s not all.
Tom also opens up about:
- The hardest lesson he learned about capital raising
- Why most new GPs underestimate the importance of investor relationships
- What changed in the syndication world since 2017
- The risks LPs don’t think about (until it’s too late)
- How a failed ATM investment reshaped his investing philosophy
-,Why experience matters more than ever in today’s market
For GPs raising money, LPs evaluating risk, or investors entering the syndication space, this episode shares practical, experience-backed insights.
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