JF 4113: When to Sell, What to Buy, and How to Think Like a Pro Investor ft. Bruce Stein

Dec 8, 2025

Bruce Stein, a real estate consultant and former fund manager, shares his journey from aspiring architect to industry expert. He offers crucial advice for new investors, emphasizing the importance of staying localized and focusing on one property type. Bruce illustrates how to identify and sell the most troublesome assets in a portfolio, and discusses strategic uses for 1031 exchanges. He highlights the significance of clear communication with investors, maintaining transparency, and aligning investment strategies with personal goals rather than just cap rates.

Ask episode

AI Snips

Chapters

Books

Transcript

Episode notes

ANECDOTE

From Architect Dreams To Fund Manager

Bruce began wanting to be an architect but gravitated to development after hands-on drafting and coordinator work.
He then spent 16 years at a family office deploying capital and later ran bridge-construction lending before consulting.

ADVICE

Start Local And Focus Your Strategy

Stay local when starting out in real estate to simplify management and oversight.
Focus on one property type until you build a track record before raising external capital.

ADVICE

Sell For Market Fit And Lifestyle, Not Just Cash

Sell when market conditions and your personal goals align, not just because you need cash.
Prioritize replacing headache properties with easier-to-manage assets even if NOI stays similar.

Get the Snipd Podcast app to discover more snips from this episode

Get the app

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/

Get 50% Off Monarch Money, the all-in-one financial tool at www.monarchmoney.com with code BESTEVER

Start earning passive income today at gsprei.com/bestever

Alternative Fund IV is closing soon and SMK is giving Best Ever listeners exclusive access to their Founders’ Shares, typically offered only to early investors. Visit smkcap.com/bec to learn more and download the full fund summary. Join us at Best Ever Conference 2026! Find more info at:

https://www.besteverconference.com/

Join the Best Ever Community

The Best Ever Community is live and growing - and we want serious commercial real estate investors like you inside. It’s free to join, but you must apply and meet the criteria.

Connect with top operators, LPs, GPs, and more, get real insights, and be part of a curated network built to help you grow.

Apply now at⁠ ⁠⁠⁠www.bestevercommunity.com⁠⁠

Podcast production done by⁠ ⁠Outlier Audio⁠

Learn more about your ad choices. Visit megaphone.fm/adchoices