BiggerPockets Real Estate Podcast I Bought 3 Rentals Then Ran Out of Money…Now I Have 50 Units
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Nov 3, 2025 Jessie Dillon, a real estate investor and small-business owner, shares her inspiring journey from burnout to building a 50-unit portfolio. She discusses how she transformed her three rental properties into a million-dollar equity through strategic partnerships. With her unique system for finding money partners, Jessie reveals how anyone can invest in real estate, even without initial capital. She emphasizes the importance of cash flow, professional property management, and long-distance investing while staying motivated through challenges.
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From Clickbait To First Purchase
- Jessie discovered real estate after reading The Simple Path to Wealth and devoured BiggerPockets content in late 2021.
- She closed her first two-family in January 2022 and continued renting while owning the property.
Target Per-Unit Cashflow Goals
- Aim for properties that can reach about $500 net profit per unit per month within a couple years.
- Use that per-unit cashflow target to back into how many units you need for your goal.
The Million-Dollar Text
- After hitting a capital limit, Jessie systematically texted 50 contacts asking for referrals to potential money partners.
- One referral led to a partnership that closed a 13-unit which later gained over $1M in equity.
