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

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