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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