Zen and the Art of Real Estate Investing with Jonathan Greene

Making Real Estate Investing as Simple as Possible with Ali Boone


Navigating the real estate world can seem complex, with advice coming from every direction. But it doesn’t have to be. On this episode of Zen and the Art of Real Estate Investing, Ali Boone, founder of Hipster Investments and a former aerospace engineer turned real estate expert and author, joins Jonathan for a conversation on making investing simple. Ali shares her insights on shifting your consumer mindset to an investor mindset for success.

Jonathan and Ali discuss her journey from aerospace engineering in the corporate world to real estate investing. She shares how her first intentional investment cost her $40,000 and her pivot from a consumer mindset into an investor mindset. Jonathan and Ali also explore the importance of grasping some fundamental real estate principles before taking the plunge into real estate as a career. Ali explains how asking someone to be her mentor played a pivotal role in her success as an investor and prevented her from exiting the industry a few times. She focuses exclusively on turnkey properties, and you’ll hear why, along with her thoughts on mitigating risk.


Jonathan and Ali touch on some key points, including:

  • Having an investor mindset is crucial for investing success. It means that you understand at a deeper level how you can profit from your investments. You also understand that you’re purchasing a property for the long term and can view that investment from multiple directions.

  • Holding properties over time contributes to wealth-building in two distinct ways. The first is increasing rents over time. The second is the compounding effect of the five profit centers Jonathan and Ali covered in the episode.

  • Asking someone to be your mentor can be a game-changer. They can guide you when you’re ready to give up or facing obstacles in your investing career. Your mentor should be someone you admire and wouldn’t mind trading lifestyles with. Ali credits her mentor with helping her stay in the investing game when she was ready to give up.

  • Turnkey properties can be great investments if you’re going to hold them for a long time. They don’t require upfront maintenance, and you can begin collecting rent immediately. The downside is that they’re more expensive to purchase on the front end.


Ali Boone has mastered the art of hassle-free real estate investing, and her thoughts on turnkey properties are invaluable.

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