Real Estate Rookie Podcast

Episode: Buying 4 Small Multifamily Rentals in Just 2 Years (While Working a W2)

Hosts: Ashley Kehr & Tony J. Robinson
Guest: Derek Brickley
Date: February 16, 2026

Episode Overview

This episode spotlights Derek Brickley’s journey from uncertainty in his W2 job to intentionally building a path out of the 9-to-5 through small multifamily investing. Derek shares how he acquired four rental properties in just two years—all while still working full-time. The discussion focuses on the mindset shifts required to get started, the practical steps for rookie investors, and how to build confidence and clarity to avoid analysis paralysis. This episode is tailored for listeners looking to make their first, second, or third real estate deal without the pressure of massive scaling.

Key Discussion Points & Insights

1. Overcoming the 9-to-5 Mindset

• Struggles at the Start
  • Derek admits he "had no idea" how to escape the 9-to-5 structure or even where to begin.
  • The biggest psychological hurdle was accepting the uncertainty and risk that comes with leaving a steady paycheck.
  • Quote: “You’re never ready. You’re never going to be fully ready.” – Derek (04:39)
• Hosts’ Perspective
  • Tony reflects on the myth of job security, recalling his mother's government job during the 2008 financial crisis, where she still faced furloughs and income cuts (03:10).

2. Action Over Perfection

• The Power of First Steps
  • Derek emphasizes that waiting for total clarity or confidence keeps people stuck. Action breeds solutions and confidence.
  • Quote: "If you just go into it thinking you have to have full confidence, you're never going to have it... Sometimes it doesn't have to be a big jump, it's just the first step." – Derek (04:39)
• Confidence is built through doing, not just learning or networking.

3. The Value and Building of a Network

• Rethinking Your Network
  • Your network comprises not only mentors but peers and service providers (e.g., contractors, handymen).
  • Ashley suggests hiring reliable professionals as part of building confidence (06:00).
  • Tony emphasizes personal responsibility in building a network, recommending digital communities and real-world meetups (07:24).
  • Quote: "Even if you have no one in your personal life today...you can go out there and build those connections." – Tony (08:23)

4. Choosing and Defining a Buy Box

• Focusing the Search
  • Derek intentionally said no to everything except small multifamily (2–4 units), aiming for house hacks in strong markets with manageable risks (09:34).
  • He designed his buy box to fit his risk tolerance and W2 schedule.
  • Quote: “Once you have crystal clear criteria… looking for the deal, that's where again, you can rely on your real estate agent, you can rely on the people in your network, but you can't go to the network and say, 'Hey, I'm looking to get started in real estate investing’... If you don't know, they can't help you.” – Derek (10:23)

5. First Deal: Surprises & Lessons Learned

• Dealing with the Unexpected
  • Initial plan was a cosmetic rehab, but DIY efforts uncovered more complex challenges (industrial glue, staples, odor issues) and went from a 4–6 week expected rehab to six months (15:38, 19:47).
  • Derek was forced to realize the value of time, importance of outsourcing, and underestimating project management requirements.
  • Quote: “…it was one of those things, you start breaking into it and it's not something you can't overcome. But what turns into what you thought was going to be a week long job…turns into months.” – Derek (15:38)
• Need for Systems
  • Derek wished he’d known before closing: have clear plans on what work is needed and who will do it (21:07).

6. Scaling: From First to Fourth Deal

• Progression
  • Derek bought his first duplex in December 2023; has since acquired three more small multifamily properties (23:08).
  • Momentum built from confidence, not deal perfection—first deal “basically breaks even” but taught invaluable lessons (24:01).

7. Management & Tenant Relationships

• Tenant Screening & Lease Enforcement
  • Derek inherited tenants and learned the significance of knowing exactly who's living in the property, with an anecdote about tenants sneaking in extra cats and roommates (30:12).
  • Ashley shares tips on enforcing leases: use the lease as the “bad guy,” consider using a third-party manager, and keep all communications in writing for legal protection (32:25, 34:00).
  • Quote: “Having as much as you can in your lease and just saying… we both signed it, we both agreed to it, and making the lease the bad guy.” – Ashley (32:25)
• Recommended Reads
  • Hug Your Haters by Jay Baer and Crucial Conversations for tenant/landlord communication strategies (35:44, 35:59).

8. Redefining the End Goal: Exit Timeline & Work/Life Balance

• Clarity After the First Deal
  • Derek now views his W2 job as a supplement, not an adversary. Multiple streams of income provide security and optionality (38:22).
  • Quote: “Do I have the flexibility that I want out of life? Can I do the things I want to do? And for a large part, I've been able to already do that, which is insane to me…” – Derek (38:22)
• Flexible Mindset
  • Real estate can offer peace of mind to change jobs, go part-time, or shift roles for fulfillment—not just a vehicle for full retirement (39:56).

9. Key Advice to Rookies

• Who, Not How
  • Derek urges listeners to focus on building a network of “who” can support and excel in areas where you lack expertise—don't try to do everything solo (41:56).
  • Approaching the business with a team mindset allows for faster and more secure growth.
  • Quote: “It's not can I do it? It's can we do it? Do I have the network to do it?” – Derek (42:16)

10. The True Return of the First Deal

• Beyond Money
  • Confidence, clarity, and proof of concept were Derek’s main takeaways.
  • Quote: “It bought me the confidence that I could do it.” – Derek (43:39)

Memorable Quotes with Timestamps

• “You're never ready. You're never going to be fully ready…if you just go into it thinking that you have to have full confidence, you're never going to have it.” — Derek (04:39)
• “Once you have crystal clear criteria…looking for the deal, that's where again, you can rely on your real estate agent, you can rely on the people in your network…” — Derek (10:23)
• “What was expected to be maybe four to six weeks turned into about six months…timing it, because, wait, okay, great, I got the floor done. Oh, wait, did I...did we ever call that guy that's supposed to come next?” — Derek (19:47)
• “It doesn't have to be a home run. It doesn't have to be the most perfect deal.” — Ashley (28:00)
• “Making the lease the bad guy...Having things in writing has saved me so much.” — Ashley (32:25, 34:00)
• “It's not can I do it? It's can we do it? Do I have the network to do it?” — Derek (42:16)
• “It bought me the confidence that I could do it.” — Derek (43:39)

Important Timestamps

• 00:00–04:39: Mindset shifts—security of W2 vs. starting real estate
• 09:34–11:16: Defining the buy box and choosing first deal criteria
• 15:26–21:07: First deal challenges—unexpected rehab issues and solutions
• 23:08–24:01: Building momentum—adding more properties after the first
• 30:12–35:44: Tenant management, enforcement strategies, and communication tips
• 36:41–39:56: Scaling, shifting from “can I?” to “how fast?” and blending W2 with investing
• 41:56–43:39: The importance of “who, not how,” and building a supportive business

Takeaways & Resources

• Book Recommendations:
  • The Book on Flipping Houses by J. Scott
  • Hug Your Haters by Jay Baer
  • Crucial Conversations
• Action Steps for Rookies:
  • Define your buy box and stick to it
  • Build a support network (online, at meetups, professionals)
  • Prepare for surprises—establish systems and contacts before you buy
  • Use clear, enforceable leases and document everything in writing
  • Focus on progress (confidence, learning) over initial perfection

Closing

Derek’s story demonstrates that ordinary people can craft an intentional path out of the 9-to-5 with a focus on education, deliberate action, and building the right support network. The hosts and guest emphasize progress, adaptability, and the unique value of the first deal as a learning and confidence-building milestone—regardless of cash flow.

Guest Contact: Find Derek at @loansbydb on all social platforms.

For more insights and actionable steps for rookie investors, catch new episodes every Monday, Wednesday, and Friday on the Real Estate Rookie podcast!