459: 19 Rentals In One Year—John's WILD Pivot Story episode artwork

EPISODE · Nov 26, 2025 · 45 MIN

459: 19 Rentals In One Year—John's WILD Pivot Story

from The DealMachine Real Estate Investing Podcast · host John Figueiredo, Ryan Haywood, David Lecko

When you hear how John Figueiredo went from running a $100M cannabis company, IPO’ing alongside Jay-Z, and literally burying cash underground… to buying 19 rentals in his first year, you’ll understand why his pivot into real estate is one of the wildest stories we’ve ever covered. In this episode, John breaks down the markets he chose, the partners he trusted (and the ones he shouldn’t have), how he scaled a portfolio fast, and why real estate became the most stable, wealth-building move after surviving a high-risk industry. KEY TALKING POINTS:0:00 - Intro0:54 - John Figueiredo’s First Deal5:48 - What He Did After Buying His First Property9:55 - Finding Good Property Managers13:39 - Why He Was Interested In Real Estate15:48 - Getting Into Wholesaling18:26 - His Marketing Strategies25:00 - Scaling The Business and Underwriting Guidelines31:56 - Why He Uses Cash Instead Of Financing32:43 - Other Investments He’s Making and Asset Allocation38:13 - Selling His Cannabis Company43:31 - Closing Thoughts44:56 - Outro LINKS:Instagram: John Figueiredohttps://www.instagram.com/fig.time/ Links: John Figueiredohttps://linktr.ee/fig_time Instagram: David Leckohttps://www.instagram.com/dlecko Website: DealMachinehttps://www.dealmachine.com/pod Instagram: Ryan Haywoodhttps://www.instagram.com/heritage_home_investments Website: Heritage Home Investmentshttps://www.heritagehomeinvestments.com/

A $100M founder reveals the wild, unexpected path that led him to 19 rentals in one year and a full pivot into real estate.

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459: 19 Rentals In One Year—John's WILD Pivot Story

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This episode was published on November 26, 2025.

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When you hear how John Figueiredo went from running a $100M cannabis company, IPO’ing alongside Jay-Z, and literally burying cash underground… to buying 19 rentals in his first year, you’ll understand why his pivot into real estate is one of the...

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