Zen and the Art of Real Estate Investing with Jonathan Greene

085: How to Make Your Real Estate Investing Journey Take Off with Shawn DiMartile


Sometimes, a stressful career pushes you to step into something new. With the right planning and business partners, you can create a real estate investing career that takes off.

On this episode of Zen and the Art of Real Estate Investing, Jonathan interviews Shawn DiMartile about leaving a high-paying air traffic control career behind to become a full-time real estate investor. Today, Shawn has more than 300 rental units and has only been investing since 2018. He is the host of The Real Estate Takeoff podcast, co-founder of Takeoff Capital, and a Navy veteran. Shawn’s focus is primarily on apartment investing.

Jonathan and Shawn begin their conversation by investigating how he was first exposed to real estate investing. You’ll also hear why Shawn wishes he’d stuck with his air traffic control job just a little bit longer before jumping into real estate investing full-time, why he feels raising money from investors to syndicate real estate is more challenging than air traffic control, and who he partnered with to make his first investment. They cover his decision to invest in Indiana instead of California, where he resides, his investment in San Diego accessory dwelling units (ADUs), and Shawn’s advice for new or prospective investors.

Real estate syndication or ADUs may not be something you’ve considered before as investment options, but Shawn offers great reasons why these asset types should be on your radar. His success story could inspire you to help your investing career take off!

In this episode, you will hear:

  • Why real estate wasn’t a consideration for Shawn DiMartile when he was younger

  • How he was initially introduced to the idea of real estate investing through the Bigger Pockets podcast

  • Shawn’s one regret about quitting his air traffic control job last year

  • The first investment he made, what he did to participate in the deal, and how he knew he was ready to go all in on it

  • His reasoning behind investing in Indiana instead of California

  • The steps Shawn takes to escape analysis paralysis

  • How he found the right business partners for this investing venture and decided on a B neighborhood

  • The booming San Diego real estate market and how accessory dwelling units (ADUs) are creating alternative housing options

  • The reason Shawn is investing in San Diego ADUs versus more traditional housing options

  • Creative financing options and finding deals in the current real estate market

  • His advice for new investors who don’t want to fall into traps a lot of people do

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple ‘+’ in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast.

If you enjoyed this episode, we’ve created a PDF that has all of the key information for you from the episode. Just go to the episode page at to download it.

Supporting Resources:

Shawn DiMartile’s website –

Connect with Shawn on Instagram –

Find Shawn on Twitter/X –

Website –

YouTube –

Instagram –

Instagram –

TikTok –

Zillow –

Bigger Pockets –

Facebook –

Email – 

Leave a Reply

Your email address will not be published. Required fields are marked *