Jessie Dillon is a Massachusetts-based beauty salon owner turned real estate investor and mentor. Since starting in 2021, she has built a portfolio of over 50 units, primarily long-term rentals, while also managing short- and mid-term rentals. Jessie specializes in partnerships, scaling through collaboration after quickly realizing the limitations of investing solo.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

Key Takeaways

Jessie transitioned from solo investor to partnerships after running out of capital.
Attending conferences like BP Con shifted her mindset and opened doors to strategic relationships.
She uses a clear, intentional process for identifying and attracting capital partners.
Building a portfolio requires patience—sometimes long stretches of “no deals” precede major breakthroughs.
Aligning partnerships and balancing equity-building with cash flow are key to long-term success.

Topics

From Beauty Salon Owner to Real Estate Investor

Began investing in 2021 with three small multifamily properties.
Quickly tapped out of capital and realized the need for partnerships.

Overcoming Resistance to Partnerships

Initially hesitant due to her solo entrepreneurial background.
A breakthrough at BP Con 2022 reframed partnerships as essential for scaling.

Building Partnerships Intentionally

Created an avatar of her ideal partner and listed 50 potential connections.
Sent messages asking for referrals, which led to her first successful capital partner.
Replicated this process to form additional partnerships.

Deal Criteria and Strategy

Focused on value-add multifamily between 8–15 units, ~$80K per door.
Looks for proforma rents at least 1.5% of purchase price.
Now pivoting toward more cash-flow-heavy assets like self-storage and short-term rentals.

The Role of Mentorship and Community

Found mentors through BiggerPockets and Women Invest in Real Estate (WIIRE).
Attends retreats and conferences to stay surrounded by action-takers.
Emphasizes balancing education with taking action.

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Jessie up for success: A deal fell apart when a capital partner pulled out last minute, forcing her to be more selective and intentional with partnerships.

Digital or mobile resource: Apple Podcasts app: accessible, free learning on the go.

Book recommendation: In the FLO by Alisa Vitti.

Daily habit: Using the Reminders app for everything to stay focused.

#1 insight for building partnerships: Only pursue partnerships that feel aligned and mutually beneficial; both sides should feel like they’re winning.

Favorite restaurant in Hopkinton, MA: Arcos.

Next Steps

Follow Jessie on Instagram: @jessiedillon_
Connect through Women Invest in Real Estate for resources and mentorship opportunities.
Check out our previous episode with Jessie: Link

Thank you for joining us for another great episode! If you’re enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you do not miss an episode.