In this episode, Lou Brown sits down with Jessie Dillon to explore how she transitioned from salon ownership to building a 50+ unit real estate portfolio in just a few years. Jessie shares how partnerships, long-distance investing, and disciplined systems helped her overcome capital constraints, scale into multifamily assets, and pursue early retirement through strategic value-add opportunities.

🎧 Hosted by: Lou Brown

👤 Guest:🖋 Jessie Dillon – Real Estate Investor & Multifamily Operator

⭐ Guest Bio

Jessie Dillon is a Massachusetts-based entrepreneur, real estate investor, and mentor who has quickly built an impressive rental portfolio since beginning her investing journey in 2021. She now manages 50 residential units, with investments spanning Massachusetts, New Hampshire, and Illinois. Specializing in value-add multifamily projects, creative financing, and off-market acquisitions, Jessie also brings experience in both short- and mid-term rentals. Her expertise has been featured in two BiggerPockets books, and she co-hosts the beginner cohort in the WIIRE Community while running workshops on buying your first rental property through local chambers of commerce, the SBA, and community education programs.

💡 Key Topics Covered

✔️ Scaling quickly through partnerships

✔️ Long-distance multifamily investing

✔️ Value-add deal execution

✔️ Capital raising strategies

✔️ Building systems for growth

📇 Connect with Jessie Dillon:

🌐 Website → https://linktr.ee/jessiedillon_

📱 Instagram → https://instagram.com/jessiedillon_

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💎 Produced by Icons of Real Estate – https://iconsofrealestate.com/