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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 - Intro 0:54 - John Figueiredo’s First Deal 5:48 - What He Did After Buying His First Property 9:55 - Finding Good Property Managers 13:39 - Why He Was Interested In Real Estate 15:48 - Getting Into Wholesaling 18:26 - His Marketing Strategies 25:00 - Scaling The Business and Underwriting Guidelines 31:56 - Why He Uses Cash Instead Of Financing 32:43 - Other Investments He’s Making and Asset Allocation 38:13 - Selling His Cannabis Company 43:31 - Closing Thoughts 44:56 - Outro LINKS: Instagram: John Figueiredo https://www.instagram.com/fig.time/ Links: John Figueiredo https://linktr.ee/fig_time Instagram: David Lecko https://www.instagram.com/dlecko Website: DealMachine https://www.dealmachine.com/pod Instagram: Ryan Haywood https://www.instagram.com/heritage_home_investments Website: Heritage Home Investments https://www.heritagehomeinvestments.com/

Episode metadata supplied by the publisher feed · Published Nov 26, 2025

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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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