From Syndicator to LP: Thomas Castelli’s Real Estate Investing Journey

In this episode of the Major League Real Estate Podcast, Nathan Sosa sits down with Thomas Castelli to unpack Tom’s path into real estate before becoming a real estate CPA. The conversation covers how Tom got started in syndications, what he learned from being on the GP side of a deal, why capital raising is often the biggest bottleneck, and how his perspective changed after investing as an LP. It is a useful look at both sides of the syndication world—from sponsor to passive investor.

How Tom Got Started in Real Estate

Before he was known as a real estate CPA, Tom was first drawn to real estate through the same path many investors take: books, meetups, and networking. After reading investing books and attending local real estate events, he became especially interested in syndications. That led him into a community where he got exposure to sponsors actively buying apartment deals and teaching others how the model worked.

That early experience gave him both education and access. He eventually invested as an LP in a 42-unit apartment deal and got a behind-the-scenes look at how the sponsors operated, which gave him early exposure to what the GP side actually looked like.

His First Deal on the GP Side

Tom’s first real step into being part of a GP team came through an 82-unit apartment deal in Jacksonville, Florida. He sourced the opportunity, helped move the deal forward, and worked alongside an experienced mentor and property manager to get it done.

The deal closed in 2017, went through renovations, and was eventually set to sell in early 2020. But COVID hit right as the sale process was underway, forcing delays, uncertainty, and eventually a concession on the sale price just to get the deal across the finish line. Even though the deal still produced a profit, it was also a real-world lesson in how quickly market conditions can change.

The Biggest Lesson: Capital Has to Come First

When Nathan asked what GPs should focus on most, Tom’s answer was clear: capital raising relationships need to be built before a deal is found.

He explained that while he was able to generate deal flow, the biggest challenge was not finding deals—it was finding the investors to close them. By the time a property is under contract, there is not much room for delay. Operators who wait until then to start talking to investors are already behind.

Tom’s advice is to identify likely investors early, talk to them about your strategy, define your buy box, and build trust before there is an actual opportunity on the table. He also noted that new sponsors should strongly consider partnering with someone who already has an investor base and track record.

What He Learned About Underwriting

Tom described his original underwriting process as a mix of sponsor guidance, basic modeling, and close collaboration with a property manager. One of the most important pieces was understanding what it would actually cost to operate the property and whether rents could realistically be pushed.

He also emphasized the importance of knowing the market. It is not enough to see that a property is under market rent. You need to know why, what competing properties look like, and whether the renovation plan really supports the projected rent increases. In his view, understanding the local market and submarket is just as important as the spreadsheet itself.

Why He Eventually Shifted to the LP Side

After that first GP experience, Tom planned to continue doing more deals, but COVID disrupted that path. He considered buying smaller properties directly and later joined another group in a GP-type role, but that opportunity ultimately did not move forward due to conflicts and changing circumstances.

Instead, he leaned more into LP investing. Over time, though, even that changed his perspective. While he had several LP investments that performed well, he also had a painful experience in an ATM fund that ultimately collapsed and turned into a major legal and regulatory mess. That experience gave him a firsthand look at what a total loss can feel like as a passive investor.

What Changed in His LP Mindset

That experience made Tom much more cautious. He said his LP “buy box” today looks very different than it did years ago. He is now much more focused on operator experience, institutional discipline, and downside protection.

One of the strongest examples he gave was an investment he made with a more experienced sponsor group in 2021. He already felt the market was near a peak, but he still invested because that group matched the term of the debt to the life of the fund. When rates later surged and many operators faced capital calls and paused distributions, that sponsor group avoided the same pressure because their financing had been structured conservatively from the start.

That reinforced a major lesson: experienced operators with real cycle-tested judgment often matter more than aggressive upside projections.

What New Sponsors Should Do Differently

Tom’s takeaway for newer sponsors is not that they should avoid the business—it is that they should not try to do it alone. His advice is to bring in experienced partners, even if it means giving up some economics.

In his view, the added credibility, judgment, and support are worth it. That experience can help with investor confidence, deal execution, and navigating challenges when things do not go according to plan.

Final Thoughts

Tom’s journey is valuable because it shows both sides of the syndication business. He saw the pressure of being on the GP side and the lack of control that comes with being an LP. That combination shaped a much more disciplined perspective on operators, underwriting, and capital raising. Interested in working with tax experts? Schedule a discovery call with our firm.

Disclaimer: This podcast summary was generated from the transcript and may contain some errors or miss key points from the audio recording. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.