Zen and the Art of Real Estate Investing with Jonathan Greene

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


Working with a spouse or partner can be tough, but with the right systems in place and a clear vision for your future together, you can also create a healthy business relationship.

On this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Tyler and Zosia Madden, the CEO and COO of Laurelless. They are real estate investors, entrepreneurs, and professional home flippers. Tyler is a general contractor and the visionary, whereas Zosia is the integrator.

Jonathan, Tyler, and Zosia begin their conversation by exploring how Tyler started as an aspiring doctor and pivoted to become a general contractor and why Zosia maintained her high-income W-2 position as they started their entrepreneurial endeavors. You’ll hear when Zosia was ready to get on board with leaving her job and becoming a part of their business, Zosia and Tyler’s mutual goal of using real estate to achieve the lifestyle they both desired, and why making the right connections helped them find new properties and learn from others. Tyler and Zosia share their reliance on authenticity to create connections with others, their advice for first-time flippers in this challenging market, and why new flippers need to build good relationships with their subcontractors. Finally, Tyler and Zosia share how they keep their personal relationship strong even amidst business conflicts and failures.

For many couples, working together may feel like a recipe for disaster, but Tyler and Zoia Madden discovered the secret sauce to establishing boundaries at work and home so that they could continue moving toward their shared goals for their family.

In this episode, you will hear:

  • How Tyler and Zosia Madden’s real estate career started with Tyler working solo and ultimately became a dual endeavor
  • Why Zosia maintained her W-2 as they started their real estate investing business and the benefits it offered
  • Zosia’s realization that she trusted where the business was going and loved the idea of it, particularly after becoming a mom
  • The role of proof of concept in getting a spouse on board
  • Using real estate as a couple to achieve the lifestyle that they want to live
  • Making the right connections to find new properties and learn from them
  • Being comfortable with being uncomfortable and getting into rooms with people who are smarter than you
  • Maintaining authenticity to build genuine connections with others
  • Moving past imposter syndrome and how having just a bit of it can help you continue to learn from others
  • Earning the ability to ask someone for their time and knowledge while being meaningful, intentional, and interested
  • Flipping homes in today’s market and Tyle and Zosia’s tips for first-timers who don’t know much
  • Building relationships with your subcontractors and suppliers who will take care of you because you take care of them
  • JV’ing on a flip with someone else to learn from them how to do a flip
  • Keeping your personal relationship strong when the business side of things feels like it’s falling apart

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Supporting Resources:

Visit the Laurelless website –

Find Zosia on Instagram –

Tyler’s Instagram –

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