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Mastering Multifamily Investment: Essential Tips for Newcomers - EP 81
🚀In this episode of The Real Estate Roundtable, Lancelot Lenard talks with investor Jessie Dillon about how she grew from 0 properties in 2021 to 50 rental units across three states in just 3.5 years.
Jessie shares the partnerships, deal strategies, and mindset shifts that helped her scale quickly in multifamily real estate. This episode is any investors looking to scale their portfolios in 2026 and beyond.
🎧 Hosted by: Lancelot Lenard
👤 Guest:🏡 Jessie Dillon – Multifamily Real Estate Investor & Educator
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 0 to 50 rental units in just 3.5 years
✔️ The strategy behind finding and structuring capital partnerships
✔️ How to identify value-add multifamily opportunities
✔️ Mindset shifts required for rapid real estate portfolio growth
✔️ Practical strategies investors should consider for 2026
🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!
💼 Connect with Jessie Dillon:
🌐 Website → https://linktr.ee/jessiedillon_
📸 Instagram → https://www.instagram.com/jessiedillon_/
🎙 Follow Lancelot Leonard – The Real Estate Round Table:
📘 Facebook → https://www.facebook.com/RealtorLancelot
📷 Instagram → https://www.instagram.com/thesirlancelotgroup/
🔗 LinkedIn → https://www.linkedin.com/in/lancelot-lenard-10b5b873/
🔖 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below!
💎 Produced by Icons of Real Estate - https://iconsofrealestate.com/
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By Lancelot Lenard
5
22 ratings
🚀In this episode of The Real Estate Roundtable, Lancelot Lenard talks with investor Jessie Dillon about how she grew from 0 properties in 2021 to 50 rental units across three states in just 3.5 years.
Jessie shares the partnerships, deal strategies, and mindset shifts that helped her scale quickly in multifamily real estate. This episode is any investors looking to scale their portfolios in 2026 and beyond.
🎧 Hosted by: Lancelot Lenard
👤 Guest:🏡 Jessie Dillon – Multifamily Real Estate Investor & Educator
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 0 to 50 rental units in just 3.5 years
✔️ The strategy behind finding and structuring capital partnerships
✔️ How to identify value-add multifamily opportunities
✔️ Mindset shifts required for rapid real estate portfolio growth
✔️ Practical strategies investors should consider for 2026
🎵 Whether you're an investor, agent, or homebuyer, this episode offers valuable insights!
💼 Connect with Jessie Dillon:
🌐 Website → https://linktr.ee/jessiedillon_
📸 Instagram → https://www.instagram.com/jessiedillon_/
🎙 Follow Lancelot Leonard – The Real Estate Round Table:
📘 Facebook → https://www.facebook.com/RealtorLancelot
📷 Instagram → https://www.instagram.com/thesirlancelotgroup/
🔗 LinkedIn → https://www.linkedin.com/in/lancelot-lenard-10b5b873/
🔖 Don’t Forget to LIKE 👍, SUBSCRIBE 🔔 & COMMENT 💬 Below!
💎 Produced by Icons of Real Estate - https://iconsofrealestate.com/