Richard McGirr interviews Bruce Stein, uncovering how his early dream of becoming an architect evolved into a decades-long career in real estate development, syndication, fund management, and now portfolio consulting. Bruce shares his path from working for a real estate syndicator, to a 16-year tenure at a family office deploying $300M, to running nationwide bridge-construction lending, and finally to advising investors on buying, selling, holding, and succession planning. He explains why beginner investors should stay local, focus on one property type, build a track record before raising capital, and avoid the common trap of chasing cap rates instead of chasing lifestyle alignment and reduced management burden.

Richard and Bruce dive into when to sell a property, how to evaluate the “biggest headache” in a portfolio, using 1031 exchanges strategically, and why the true goal is to simplify your real estate life—even if the cash flow stays the same. Bruce also offers candid insights into raising three separate $100M funds: why specificity, transparency, investor expectation management, and sticking to your lane matter more than anything else. The episode closes with a practical capital-raising tip: be specific, be consistent, and give investors enough time to underwrite YOU as much as the deal.

Bruce Stein
Current role: Real Estate Consultant & Former Fund Manager
Based in: California
Say hi to them at: https://www.linkedin.com/in/brucejstein/

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Podcast production done by⁠ ⁠Outlier Audio⁠

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