Interview: How to Harness the Power of Real Estate Tax Strategies to Grow Your Investments

Interview: How to Harness the Power of Real Estate Tax Strategies to Grow Your Investments

1 min read
Jordan Thibodeau

Jordan Thibodeau is a tech employee and real estate investor. He made his first investment in the stock market at age 12 and has been hooked on investing ever since.

Jordan is a fourth generation real estate investor; his great grandfather used to develop apartment complexes in Boston, and his grandpa and dad purchased 36 homes in the Bay Area in the 1970s.

While working with his father, Jordan learned the family business and made his first real estate investment in 2013—a duplex in Sacramento that he partnered with his dad to purchase. Jordan went on to form the Silicon Valley Investors Club. With nearly 6,000 members, it is one of the largest investing clubs for current and former tech employees. Through this club, he has helped hundreds of investors get started with real estate investing—be it their first buy and hold, multifamily purchase, syndication investment, or REIT investment.

Jordan has been contributing to the BiggerPockets community for nearly five years. He is also the author of a free investment newsletter called Investor’s Therapy, a publication focusing on human psychology and its impact on investment decisions.

Jordan has interviewed or hosted some of America’s top thought leaders and investors such as Ray Dalio, Anne Wojcicki, Tim Ferriss, Ryan Holiday, Annie Duke, Ben Horowitz, and Eric Barker to learn about human psychology and what we can do to make better investment decisions. He has also interviewed or hosted RE professionals such as Josh and Brandon, Gino Blefari (CEO of Berkshire Hathaway’s real estate division), Jay Papasan, J Scott, and Amanda Han. You can also find more of his writing on and

During the day, Jordan works on the Mergers & Acquisitions team for a major tech company.

Jordan majored in Political Science at Santa Clara University and has taken business school classes at Stanford’s Graduate School of Business.

Twitter @JWthib
Investor’s Therapy
Silicon Valley Investors Club on Facebook

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I had the pleasure of interviewing my friends Amanda Han and Matthew MacFarland, authors of  The Book on Tax Strategies for the Savvy Real Estate Investor.

Amanda and Matt are the husband and wife CPA team behind Keystone CPA, a certified public accountant practice that specializes in helping real estate investors create plans that keep more of their cash and give less to the IRS. In addition to advising real estate investors every day, Matt and Amanda are also real estate investors who understand the power that tax savings can have on the growth of an investment.

Related: Tax-Saving Strategies for Real Estate Investors: How to Pay Less & Keep More This Year

What This Interview Covers

We talk about:

  • Can I write off expenses incurred when investigating the purchase of an investment property (e.g. travel, inspections) if I ultimately decided not to purchase the property?
  • How does tax strategy or planning differ from just doing taxes retroactively?
  • What software do you prefer your client to use to track their expenses?
  • How can we write our kids off? Economically and also emotionally?
  • How should someone pick a CPA?
  • What are some common mistakes CPAs might make when doing a real estate investor’s taxes?
  • How can I write off my vacation?
  • Do I need an LLC? Why should I have one? And when it does make sense to go without one? If I’m buying my first property, can I get away with not having an LLC? Does a legal entity mean more tax deductions?
  • And much more!

Also, if you missed my last interview with Gino Blefari, the chief executive officer for HSF Affiliates LLC, you can find it here.

Have any questions about the topics covered in this interview?

Let’s talk in the comments section below!