From Aerospace Engineer to Lifestyle Real Estate Entrepreneur with Ali Boone

Today, I am super excited to welcome lifestyle entrepreneur, author, and real estate investor Ali Boone to the show. After leaving her 9-to-5 corporate job to pursue ultimate freedom through entrepreneurship, her company Hipster Investments managed to facilitate over $18M in real estate transactions in its first five years of business. She has Master’s degrees in both Aerospace Engineering and Spiritual Psychology. Ali also teaches flying and can often be found snowboarding or volunteering in prisons.

We start off as we always do with Ali sharing her background with us. She said she initially wanted to study to be a pilot because of the influence of her family, but ended up in aerospace engineering. After earning her advanced degree, she shared that on her very first day of work, upon walking into her cubicle, she realized she did not want to work in the corporate world. She wasn’t sure what she wanted to do and took the next five years reading everything she could get her hands on. Ali eventually started investing in real estate for personal wealth growth and turned it into the venture that would get her out of her corporate job, which she left in 2012. Ali started her own company named Hipster Investments that deals in mostly turnkey rental properties.

Because of my research into Ali, I knew that she had a Spiritual Psychology degree in addition to her technical degrees and I wanted her to explain how she ended up pursuing that. She said she actually started the program because she thought it would be hilarious to tell people she has such diverse degrees, but it ended up being the biggest game-changer of her life. Because it involves an aspect of psychology, she can apply the principles to every aspect of her work and life.

Then we dove into the specifics of Ali’s real estate adventures. She first tried to invest in a deal in Nicaragua that didn’t end up being successful, but then turned to the burgeoning Atlanta market. I asked specifically why she chose turnkey rentals in lieu of other strategies like flipping houses. She said it wasn’t as though she couldn’t learn and be good at putting a lot of work into properties to rehab them, but she wasn’t passionate about it. She got out of the corporate world to have the freedom and flexibility to do what she loves, not to make more work for herself. We discuss a lot of the pros and cons of turnkey rental investing and some of the difficult situations we have both found ourselves in with this strategy.

I then asked Ali to explain the services that Hipster Investments provides. She said they are basically a referral service because when she first started investing in turnkey rentals, everyone she knew wanted to learn more about what she was doing. Ali ended up writing articles about turnkeys for BiggerPockets and this led to so many people asking her for advice, her company ended up being a “glorified matchmaker” between investors and the providers she could recommend for this investing strategy. Ali also feels very rewarded by staying on to help support the investors who she consults with. She also explained her process for analyzing and vetting new turnkey providers for her clients.

I then asked Ali to tell us about her first book, NOT Your How-To Guide to Real Estate Investing: Life Lessons on Hacking Your Mind Before You Hack Your Wallet. She said that she had started several books but had no interest in learning how to go about publishing a book, so she was constantly getting stalled in this process. But with the coronavirus lockdowns, she had no excuses left and it really provided her with the time and space that she needed to finally get her book completed and published. Ali explains that she really wanted to focus on the self-examination a person needs to make before jumping into real estate investing so that they know their strengths and weaknesses and what strategy might work the best for them.

Because Ali is all about lifestyle, we wrapped up with her telling us about the lifestyle she is cultivating and how she spends her days. We discuss how important it is to find what really brings you joy and take advantage of the freedom provided by being in business for yourself. You really don’t want to miss this episode of Just Start Real Estate… Ali and I just have a blast! She provides us with so much wisdom and actionable advice in a completely laid-back and fun manner so be sure to take the time to listen and learn from this fantastic guest, Ali Boone!