When your net worth is in the millions but your bank account is nearly empty, what do you do? Wyatt Simon opens up about the raw moment in early 2024 when he found himself in tears, contemplating getting a job—despite owning 185 units and a $20 million portfolio. In this episode, Wyatt walks us through his evolution from taking a $200K line of credit to building (and pivoting) a real estate empire, moving from multifamily operations to flipping, hard money lending, and mentoring investors. Eugene and Wyatt compare war stories from development and property management trenches, explore financing strategies, and discuss the systems and mindsets needed to succeed. If you’ve ever thought about jumping into real estate—or stepping back to rethink your path—this episode is full of cautionary tales, practical strategies, and inspiration.
Guest Bio
Wyatt Simon is a seasoned real estate investor, operator, and coach who began his journey with a $200,000 line of credit and grew it into a $20 million portfolio. Known for his “get rich slow” philosophy rooted in real estate, Wyatt has experience spanning single-family rentals, multifamily properties, property management, and hard money lending. He’s also the author of 100 Units: The Real Estate Investor’s Playbook to Scaling a Rental Portfolio, and is passionate about teaching others how to systemize and scale their real estate businesses. Wyatt shares his knowledge widely through social media, YouTube, and coaching programs.
Episode Highlights and Chapters
00:00 - Wyatt’s early real estate journey: from failing at his first job to buying his first duplex
02:00 - Jumping into multifamily in 2021 without formal coaching
03:00 - Lessons from property management and losing $33K to bad bookkeeping
04:00 - A candid 2024 turning point: “I thought I’d have to get a job”
05:30 - Pivoting from multifamily to flipping and wholesaling single-family homes
06:45 - Using a family line of credit to buy his first property and the BRRRR strategy
08:00 - Eugene breaks down risk and funding in new development
11:00 - Wyatt’s early mistakes, including losing $68K on a flip
13:00 - Why cash flow and overhead planning are critical for real estate entrepreneurs
14:30 - Property management nightmares: what made Wyatt take it in-house
17:00 - Lessons from Michael Gerber’s The E-Myth and becoming a business builder
19:00 - Implementing EOS and scaling with systems
21:00 - Wyatt’s only syndication deal: a win, but not worth the time
22:30 - Ethical dilemmas and overpaying in today’s multifamily market
24:00 - How Wyatt structures his hard money lending and sources investor capital
27:00 - Eugene’s creative strategies for financing development without outside LPs
30:00 - Why Eugene launched multiple retail funds for development and distressed assets
32:00 - Wyatt on content marketing and building investor trust through social media
33:00 - Writing 100 Units to answer the questions people kept asking
35:00 - Final advice: “Most successful people are just dumb enough to take the risk”
Contact Information
Instagram: @wyattbuysbuildings — https://www.instagram.com/wyattbuysbuildings
YouTube: Wyatt Buys Buildings — https://www.youtube.com/@WyattBuysBuildings
Website: https://www.wyattsimon.com
LinkedIn: https://www.linkedin.com/in/wyatt-simon/
Free Deal Analyzer Tool: Available on his website
Learn more about the host, Eugene Gershman, and access more episodes:
https://giscompanies.co/podcast/
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