Real Estate Rookie Podcast - Episode Summary
Zero to 50 Units in 4 Years (Financial Independence Cheat Code)
Host: Ashley Kehr and Tony J. Robinson (BiggerPockets)
Guest: Jessie Dillon
Date: September 22, 2025
Episode Overview
In this episode, hosts Ashley and Tony reconnect with investor Jessie Dillon to unpack her journey from rookie to holding over 50 rental units in just four years. The conversation drills deep into the strategies behind her rapid scale-up—focused buy boxes, capital partnerships, long-distance investing, systems to avoid burnout, and the tough emotional realities behind the scenes. Jessie also shares actionable advice for beginners looking to build lasting momentum, demystifies on- and off-market deal sourcing, long-distance acquisition, and how to manage growing portfolios without losing your mind.
Key Discussion Points & Insights
1. Jessie's Growth Journey: From Rookie to 50 Units
- Strategic patience and timing: Jessie describes a phase of “planting seeds” and a subsequent rapid leap from 17 to 50 units in a single year (01:00 – 01:51).
- She credits her breakthrough to surrounding herself with experienced people and trusting in “divine timing.”
2. Staying Laser-Focused: Crafting a Clear Buy Box
- Jessie avoided distraction by maintaining an "ultra-specific buy box," defining property types, funding sources, and acquisition strategies.
“I could not have been more specific about what I wanted to do. I had a really hyper-specific buy box... and I didn’t stray from that plan.” (01:58, Jessie)
- She reverse-engineered her goal by targeting $15,000/month net cash flow, which mapped to acquiring ~50 units in four transactions, mainly via value-add multifamily in partnerships (02:45 – 04:09).
3. Building and Leveraging Partnerships
- Systematic relationship-building was key: weekly social posts, monthly email newsletters, speaking at meetups, and direct outreach to potential partners.
“I texted a list of 50 people...That was a half a million dollar text I had sent and within a couple of years it'll easily be a million dollar text.” (06:35 – 08:57, Jessie)
- Jessie emphasizes defining your ideal partner, aligning on personality, contribution (capital, time horizon), and trusting intuition.
“You have to both feel like you’re getting the, you know, the good end of the deal.” (12:00, Jessie)
4. Endurance & Invisible Work: What Most Don’t See
- There's an intense period of “thankless work”—long stretches with slow or no progress:
“There were multiple times that I was...crying, being like, I’m doing all the right stuff. Why is nothing working?” (15:02, Jessie)
- Success was a combination of groundwork and being prepared for opportunities when timing aligned.
5. Deal Sourcing: On-Market vs. Off-Market
- Most of Jessie’s deals were sourced via agents and pocket listings, not traditional off-market channels:
“I have found almost all my deals through agents...there are tons of on market deals that are really good.” (16:51, Jessie)
- She encourages new investors not to overlook on-market deals and negotiate assertively.
- Pocket listings explained (18:18 – 19:11): Pre-market deals shared privately with selected buyers.
6. Structuring Partnerships
- Jessie’s preferred structure: Equal beneficiaries of a trust, capital partner supplies down payment and reserves, she handles acquisition and asset management.
“We split equity and cash flow 50/50 and we go into it expecting to not take a distribution for the first couple of years...” (19:44, Jessie)
- Flexibility is important: Not every prospective partner will align with her structure, and that’s okay.
7. Scaling Without Burnout: Systems and Delegation
- Jessie built a team: Key support from a highly capable virtual assistant and a second assistant handling repeatable tasks; uses Monday.com and digital reminders to track work.
“Anything that’s repeatable... doesn’t require your face or voice can usually be offloaded.” (23:47, Jessie)
- Documenting processes early is crucial for smooth hiring later.
8. Long Distance Investing: Why and How
- Difficulty finding deals that penciled locally led Jessie to the Midwest (Chicago):
“If we have to have a management company anyways...there’s really no need for it to be in our backyards.” (25:50, Jessie)
- Decision to purchase out-of-state was made on a Friday, under contract by that Sunday—enabled by prior networking and research.
“One person connects you to the next...once you get one really good person on your long distance, will connect you to all the other people that you need.” (28:33, Jessie)
- Advice for rookies: List worst-case scenarios, plan solutions, and start introductory calls with local agents and property managers (30:39).
9. Asset Management vs. Property Management
- Asset management is oversight: Big-picture monitoring, monthly check-ins, strategic decisions. Property management is day-to-day.
“My role essentially is to meet with the property manager... I’m down to just a very thorough check-in for each property via email once a month.” (36:01, Jessie)
- Self-management not for everyone; oversight is still critical even when delegating.
10. What’s Next: Future Pivot
- After four years of value-add multifamily, Jessie’s now eyeing self-storage for quicker cash flow.
“My portfolio is very delayed gratification heavy right now. ...I want to now shift into a little more like short term cash flow. So...we actually are offering on self storage right now.” (40:29, Jessie)
- Her advice: Block out distracting trends; pursue strategies aligned to your lifestyle goals.
Notable Quotes & Memorable Moments
“I think if I got distracted trying to chase two rabbits, I would have caught neither.” — Jessie (02:01)
“Everything you’re doing is content. Everything is something somebody’s interested in.” — Jessie (06:35)
“I texted those 50 people...and one of my partners came from those texts. And today we have over $1 million of equity in our property.” — Jessie (08:57)
“There were multiple times that I was sitting on my back deck crying, being like, I’m doing all the things I know I’m doing the right stuff. Like, why is nothing working out?” — Jessie (15:02)
“LoopNet is where deals go to die. I do not believe in that. I have found almost all my deals through agents.” — Jessie (16:51)
“You want to really feel each other out. It takes multiple phone calls or Zoom calls or coffee meetings to really figure out if you want to enter this like business marriage with someone.” — Jessie (12:00)
“Nothing happened for, like, two years. So there was a lot of work that felt like...nothing was happening...and then, you know, I had 17 units. I was really pushing for 50...February 2025, I closed on an eight unit. June 2025, I closed on a 13. July 2025, I closed on a 12 unit. So everything happened all at once, even though I had been putting in all this thankless work for a couple years to get there.” — Jessie (15:02 – 16:41)
Timestamps for Key Segments
- Jessie’s update and leap to 50 units: 01:00–01:51
- Importance of staying laser-focused (buy box): 01:58–04:09
- Defining and finding the right capital partners: 06:35–08:57, 12:00–15:02
- Handling “thankless work” before success: 15:02–16:41
- Deal sourcing: on-market vs. off-market and pocket listings: 16:51–19:11
- Structuring JV partnerships: 19:44–22:13
- Scaling with assistants and documentation: 22:33–24:48
- Pivot to long distance investing and first deal in Chicago: 25:50–29:46
- Advice on starting with long-distance deals: 30:39
- Difference between asset and property management: 36:01–38:08
- Future plans and advice to block out market “shiny objects”: 40:29–42:35
Actionable Tips for Listeners
- Define your end goal first, then backwards-engineer your buy criteria.
- Stick to your plan and give your seeds time to grow, even when progress seems invisible.
- Build your network deliberately—document what you do and share it, but don’t be afraid of slow growth.
- Don’t fixate on off-market “unicorns”—there are great deals on the MLS and through agents.
- Structure partnerships for alignment and be unafraid to say “no” if it’s not a fit.
- Delegate early and document everything, even before you’re ready to hire.
- Long-distance deals are enabled by strong systems and networking—start by having conversations.
- When outsourcing property management, maintain owner-level oversight.
- Stay focused on your strategy—not social media trends.
Connect with the Guest
- Instagram: @jessiedillon_
This episode is a must-listen for investors who crave both actionable techniques and honest talk about the emotional grind and discipline behind the “overnight” success story. Jessie’s journey proves that momentum in real estate comes from relentless focus, strategic relationships, and persistent behind-the-scenes legwork.