Zen and the Art of Real Estate Investing with Jonathan Greene

046: Documenting the Real Estate Investing Journey with Lili Thompson


Many new real estate investors are first introduced to investing when they learn about house hacking. They view it as a clever way to pay their mortgage while saving for their next home. For others, it introduces them to the world of real estate investing.

Once you’ve been introduced to real estate investing, you begin to learn all the methods available to you quickly. It can include mixed-use properties, wholesaling, or just buying and holding good deals.

In this episode of Zen and the Art of Real Estate Investing, Jonathan interviews Lili Thompson, a young real estate investor with a large YouTube following and a successful business. A former basketball player, she was first introduced to real estate as a child. After college, she began learning about real estate investing with podcasts and books, and–with the support of her parents–she embarked on her own investing career.

Lili is a young and successful investor, but in the last few years, she’s learned many lessons she’s eager to share with others.

In this episode, you will hear:

  • Lili’s first exposures to real estate investing and how house hacking became her first foray into it following a basketball career

  • Her parents’ role in her initial investment and how house-hacking turned into a short-term rental

  • Where she attained the confidence and knowledge to start investing during the pandemic and build relationships with other investors

  • How Lili got into wholesaling and overcame the bad reputation wholesaling has

  • Why a balanced approach helped her stick through the adversity

  • Lili’s method for getting comfortable with what a low-cost property looks like and what it might take to renovate it

  • Her profit expectations when she started and how she accounts for solving problems during negotiations

  • Why this isn’t a get-rich-quick scheme, and you have to approach it that way

  • The resume-building power of wholesaling and the importance of presenting yourself as a business or entrepreneur

  • How Lili overcame the pushback she got as a young, Black female investor and the accessibility and accountability her YouTube channel provides to others

  • What her future plans are with this tighter real estate market, and how content creation has played a part in new opportunities

  • The one piece of advice she’d give new investors

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Supporting Resources:

Lili Invests –

Lili Thompson’s website –

Find Lili on YouTube –

Lili on Instagram –

Connect with Lili on LinkedIn –

Visit Lili’s TikTok –

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