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In this episode, I sit down with Matt Stillman, a seasoned real estate investor and entrepreneur, to discuss his journey from financial struggle to building a thriving real estate portfolio. Matt shares how he went from earning $38K per year to making six figures in just six months, only to lose his job and use that setback as fuel to become a self-made real estate investor. We dive deep into mindset shifts, portfolio optimization, and the tough lessons he learned along the way. If you’re looking to break free from financial limitations and scale your investments, this episode is packed with actionable insights.

Timestamps:

00:00:00 – Intro

00:01:19 – Matt’s journey from struggle to success

00:04:06 – How a mentor changed Matt’s financial mindset

00:05:38 – Scaling from 1 to 51 properties

00:09:13 – Getting fired & the wake-up call to entrepreneurship

00:12:47 – The power shift: Making $50K on your own vs. $250K as a W2

00:17:00 – How Matt optimizes his portfolio for maximum returns

00:21:59 – When to sell vs. hold real estate investments

00:28:26 – The cost of bad investments & lessons learned

00:35:30 – Why mindset is the key to scaling your business

00:42:56 – Breaking free from financial programming

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*None of this is meant to be specific investment advice, it's for entertainment purposes only.