324. Which Boring Strategy Still Wins in 2025? With Henry Washington

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Apr 30, 2025

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ANECDOTE

Henry's Boring Strategy

Henry focuses on buying distressed properties, renovating, and then either renting or selling them.
He prefers local single-family and small multifamily properties within an hour's drive of his base.

ADVICE

Find Sellers' Pain Points

Find sellers who have pain points that make them willing to sell at a discount.
Serve those sellers by offering solutions like speed or flexibility to help them sell when traditional routes can't.

ADVICE

Use Proven Deal Sourcing

Consistently use proven methods like direct mail and online ads to find deals.
Increase marketing volume to buy properties at deeper discounts in tougher markets.

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In this episode of the Tax Smart REI Podcast, Thomas and Ryan sit down with seasoned real estate investor and author Henry Washington to discuss why he’s not chasing creative finance trends, and why his “boring” strategy continues to deliver results in 2025’s unpredictable market. Tune in to learn: - Why Henry sticks with off-market deals and direct mail (even in the age of AI). - How he adjusts his strategy based on market cycles—without overreacting to headlines. - Why he believes helping sellers matters more than squeezing every dollar. - How to find pain points in the market—and actually solve them. - What newer investors get wrong by chasing the “next big thing.” If you’re looking for a grounded, proven approach to real estate investing, even in times of rising rates and economic uncertainty, this episode will give you clarity and confidence. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX Join the Tax Smart Insiders Community: go.therealestatecpa.com/3Xx1Cpd Connect with Henry on Instagram: @thehenrywashington Check out Thomas's new YouTube channel: www.youtube.com/@thomascastelli The Tax Smart Real Estate Investors podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.