NOT Your How-To Guide to Investing in Real Estate with Ali Boone

NOT Your How-To Guide to Investing in Real Estate with Ali Boone - Feature Image

Ali Boone – the founder of Hipster Investments, is a real estate investor and lifestyle entrepreneur and has literally defined non-conformity when it comes to her career. Ali left her corporate 9-to-5 job as an Aerospace Engineer, despite the “dream job” status that came with it, to start her real estate investing company, Hipster Investments. Hipster managed to facilitate over $18M in real estate investment transactions in its first five years of business. Ali’s primary focus in real estate, and with Hipster, revolves around passive income and passive investment options, and she is most involved with turnkey rental properties.

In this episode, we get an update from Ali about the good and the bad of her first foray into life as a landlord of a duplex in her hometown. We talk about what she calls the Three Currencies you need to focus on when beginning your real estate investing journey, and the difference between Working versus Investing, and how that impacts the various real estate investing strategies you might choose to focus on.

Post-Interview Analysis 

  • Key Lessons Learned: Begin with the end in mind and take stock of what you have before beginning your real estate investment journey. Do you really have the time to invest actively? If you lack the time to invest actively, might you be better off focusing on your core income-producing endeavors and seek out more passive opportunities with slightly lower returns. 

Episode Highlights: 

  • Schedule a video chat with Neil Henderson at
  • After years of owning rental properties, Ali Boone became an actual landlord for the first time about two years ago. We check in with how that’s going for her.
  • Ali Boone has a new book out called NOT Your How-To Guide to Investing in Real Estate. It’s not a book about the nuts and bolts of any particular real estate investing strategy, it’s a book about the mindset of a real estate investor.
  • The Three Currencies of every potential real estate investor must consider and why they are important
  • Beginning with the end in mind and understanding the difference between Working and Investing as it pertains to different real estate investment strategies.
  • And much more…

Books and Resources Mentioned

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