Chris Crosby (Buckingham Investments): Education-First Real Estate Investing, Cash-Out Refis, and a Boston-to-California Move at 22 episode artwork

EPISODE · Jun 15, 2026 · 47 MIN

Chris Crosby (Buckingham Investments): Education-First Real Estate Investing, Cash-Out Refis, and a Boston-to-California Move at 22

from Let Me Tell You a Quick Story · host Chris Chudacoff

Quick story before you hit play. Chris Crosby is one of my favorite people to talk shop with, and not because he is loud about it. He is the opposite. He is the guy who will sit with you for months before he ever shows you a property, because he would rather you understand what a great deal actually looks like before he ever asks for a commission. That mindset is rare, and it is exactly why I wanted him on the show.In this episode, Chris and I talk about leaving Boston in the middle of a blizzard at 22, why your 20s and 30s are made for taking chances, and how he built a real estate portfolio from a starter triplex while helping his clients do the same.Here is what you will pick up:The education-first model at Buckingham Investments and why it actually worksSmart, low-down-payment ways to get into your first rentalWhen a cash-out refinance beats a 1031 exchange (and when it does not)Why an annual equity review can change the next ten years of your portfolioWhat is happening in commercial multifamily right now after four years of rate resets, and where Chris sees opportunityConnect with Chris:Phone: (650) 549-4849Email: [email protected]: @investorinsight1Buckingham InvestmentsAnd if you need a mortgage advisor in your corner for the home or rental property side of the equation, that is what I do every day at True Point Lending. Come find me at truepointlending.com.

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Chris Crosby (Buckingham Investments): Education-First Real Estate Investing, Cash-Out Refis, and a Boston-to-California Move at 22

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