In this episode, I’m joined by Brian Green, a former history teacher who quietly built a real estate portfolio that eventually set him free from the classroom. Brian shares how he bought his first property with a loan from his dad, scaled to multifamily, and ultimately made the leap into full-time investing.

We dive into the realities of transitioning from W-2 to full-time investor, what he learned from flipping houses and running a property management company, and how he balances risk while growing his holdings. Brian’s story is proof that you don’t need a flashy background or a finance degree to build lasting wealth—you just need commitment, patience, and a plan.

Episode Highlights:

[0:00] – Why development is hard and who’s built for it

[3:00] – Brian’s self-introduction and what he’s doing today

[6:00] – From Verizon franchises to real estate—his early entrepreneurial days

[9:00] – Buying a snowplow to be the ultimate DIY landlord

[12:00] – Spinning off the construction division and building a vertically integrated business

[15:00] – The evolution from teacher to real estate entrepreneur

[18:00] – Selling the previous company and what came next

[21:00] – Rejecting the 4% retirement advice and building his own strategy

[24:00] – Why Brian never wanted to work for corporate America

[27:00] – Bringing in his brother as a partner and scaling up

[30:00] – How geography influences his investing decisions

[33:00] – Knowing the local politics, players, and competitors is a competitive edge

[36:00] – Thriving in markets bigger investors ignore

[39:00] – How deep local knowledge leads to better deal flow

[42:00] – Wrapping up with final insights and parting advice

5 Key Takeaways

1. Start small, start smart – Brian’s first deal wasn’t flashy, but it was foundational.

2. Side hustles can become full-time businesses – He built his portfolio while working full-time until the timing—and math—made sense.

3. Flipping isn’t always the answer – Brian shares why he left house flipping for more sustainable, long-term gains.

4. Owning the management process creates leverage – Starting a property management company gave him control and scale.

5. Clarity and numbers matter – Knowing your goals and understanding your risk tolerance are key before making the leap.

Links & Resources

• Green Springs Capital – Learn more about Brian’s investing company

• Books Mentioned: The Millionaire Real Estate Investor, Rich Dad Poor Dad

• Connect with Brian on LinkedIn

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