Zen and the Art of Real Estate Investing with Jonathan Greene

Growing a Real Estate Proof of Concept as a Couple with Tyler and Zosia Madden


In the latest episode of Zen and the Art of Real Estate Investing, Jonathan interviews Tyler and Zosia Madden, the couple behind Laurelless, where Tyler serves as CEO and Zosia as COO. As real estate investors and professional home flippers, they share how they’ve successfully navigated the challenges of working together as spouses. Tyler, a general contractor and the visionary of the business, and Zosia, the integrator, reveal their strategies for maintaining a healthy relationship at work and home.

Jonathan’s conversation with Tyler and Zosia explores Tyler’s path from pre-med student to general contractor and Zosia’s decision to keep her high-income W-2 job during the early stages of their business. They discuss when Zosia decided to join their business full-time, driven by their shared goal of using real estate to achieve the lifestyle they wanted. The Maddens emphasize making the right connections, remaining authentic in their interactions, and learning from others in the industry. They offer advice for first-time flippers, outlining building good relationships with subcontractors in a challenging market. Additionally, Tyler and Zosia share how they maintain a strong personal relationship, establishing boundaries to navigate business conflicts and failures while continuing to pursue their family goals.

 During their conversation, you’ll hear more from Jonathan, Tyler, and Zosia about:

  • If you’re going to work with your spouse, be clear about your goals and how you’ll achieve them.
  • Creating authentic connections is crucial to meeting your real estate goals.
  • When you can’t offer expertise because you don’t know anything yet, you can still offer a human connection and friendship.

 Tyler and Zosia Madden have achieved great success at home and in their business by setting boundaries and creating a shared vision. They outline how others can do the same while acknowledging that it isn’t for everyone.

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