From Burnout to 50 Units: Scaling Through Partnerships & Long-Distance Investing - EP 35

Описание: 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.

💡 What You’ll Learn
✔️ How Jessie scaled from zero to 50+ units quickly
✔️ Using partnerships to overcome capital limitations
✔️ Why long-distance investing unlocked better deals
✔️ Finding value-add multifamily opportunities
✔️ Building systems, teams, and property management remotely

👉 Watch now to learn how partnerships and strategic pivots can accelerate your real estate investing journey.

⏳ Timestamps (Click to Jump to Sections!)
📌 00:00 Introduction and Guest Welcome
📌 00:30 Jessie's Background and Real Estate Journey
📌 01:32 Diverse Real Estate Portfolio
📌 03:05 Long Distance Investing
📌 09:28 Challenges and Strategies in Property Management
📌 16:05 Capital Raising and Partnerships
📌 21:07 Future Plans and Real Estate License
📌 23:24 Balancing Real Estate and Personal Life
📌 25:16 Advice for New Investors
📌 27:09 Conclusion and Final Thoughts

📇 Connect with Jessie Dillon:
🌐 Website → https://linktr.ee/jessiedillon_
📱 Instagram →   / jessiedillon_  

🎙 Follow Lou Brown – The Whole Enchilada of Real Estate Investing:
📘 Facebook →   / streetsmartinvestor  
📷 Instagram →   / loubrown4860  
🔗 LinkedIn → linkedin.com/in/lou-brown-5445545
📺 YouTube →    / @streetsmartinvestor  

🔖 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below!
💎 Produced by Icons of Real Estate – https://iconsofrealestate.com/

#RealEstateInvesting #Multifamily #Partnerships #LongDistanceInvesting #LouBrown