Retire on Rentals
Retire on Rentals
Podcast Description
We educate investors and potential investors on the in's and out's of investing in rental property. We focus on residential and multifamily investing, but include commerical, storage, mobile home parks, and more. We interview industry experts on tax strategies, property management, vendor selection, syndications, capex, and more.
Podcast Insights
Content Themes
The podcast covers a broad range of topics in real estate investing, including residential and multifamily properties, tax strategies, property management, and financing options. Specific episode examples include discussions on pivoting from single-family to multifamily investments, innovative self-storage development approaches, and unique lending products tailored for real estate investors, aimed at bridging knowledge gaps for both novice and experienced investors.

We educate investors and potential investors on the in’s and out’s of investing in rental property. We focus on residential and multifamily investing, but include commerical, storage, mobile home parks, and more. We interview industry experts on tax strategies, property management, vendor selection, syndications, capex, and more.
Episode Summary
In this insightful episode, Nicholas Cook sits down with seasoned multifamily broker Sean Worl from Colliers in Portland. Sean shares his journey from aspiring developer post-2008 crash to becoming a leading broker, highlighting the value of brokerage experience in understanding market dynamics.
Key topics include the critical role of reputation in getting offers accepted, the prevalence of dual agency (about 75% of deals), and how brokers balance fiduciary duties while prioritizing deal execution. Sean offers candid advice for new investors: build relationships by conveying confidence, provide proof of funds, and aim for “doubles” rather than grand slams on first deals to build momentum and credibility.
The conversation dives into underwriting support, off-market deals, commissions (typically 4-6%, negotiable), and common pitfalls like over-leveraging—recommending 35-50% down payments to weather downturns. Sean emphasizes a long-term, patient mindset: “Do boring deals” and think generationally.
On the Portland market as of the recording, Sean notes historic buying opportunities with some urban asset values reverting to 15-year-ago levels amid challenges like stagnant rents, rising expenses (insurance, taxes, repairs), and regulations. He views current regulations as providing future safeguards against extreme rent spikes while acknowledging they complicate operations.
Personally, Sean discusses unplugging through carpentry, golf, and family time with his three young daughters, plus bucket-list goals like family travel and finishing a story started during COVID.
This episode is a must-listen for anyone investing in multifamily, especially in regulated markets—packed with actionable insights on working with brokers, underwriting realistically, and navigating today’s opportunities.
Show Notes with Timestamps and Notable Moments
(Timestamps are estimated based on transcript flow and typical podcast pacing; actual may vary with editing.)
- 00:00 – 01:30 | Introduction
Nicholas introduces the podcast and guest Sean Worl. - 01:30 – 04:30 | Sean’s Background and Entry into Multifamily Brokerage (Notable Moment)
From fixing/flipping with his dad to joining Marcus & Millichap during the development hiring freeze. - 04:30 – 07:00 | Building Credibility and Milestone Deals
Confidence builds every 3-5 years through experience. - 07:00 – 10:30 | Role of Reputation in Deals (Notable Moment)
Closing track record often trumps slightly higher offers in competitive scenarios. - 10:30 – 14:00 | Dual Agency Explained
Common in multifamily for better execution; ~75% of Sean’s deals. - 14:00 – 17:00 | Addressing Dual Agency Concerns (Notable Moment)
“It’s a big boy’s world”—experienced buyers prioritize getting the asset. - 17:00 – 20:00 | Transparency and Commissions
Typical 4-6% range, shared if co-brokered, often capped on larger deals. - 20:00 – 24:00 | Advice for New Investors Building Broker Relationships (Notable Moment)
Convey confidence, be steadfast on reasonable deals, underwrite to a “double.” - 24:00 – 27:00 | Vetting Buyers
Proof of funds and track record essential; higher-end deals include interviews. - 27:00 – 30:00 | Underwriting Help from Brokers
More guidance for novices, always connecting to third-party pros. - 30:00 – 32:00 | Off-Market Deals (Notable Moment)
Loved for exclusivity (buyers) and simplicity (sellers). - 32:00 – 35:00 | Off-Market Distribution + Regulations
Prioritized by buyer fit; buyers must stay informed on rules. - 35:00 – 38:00 | Common Pitfalls (Notable Moment)
Over-leveraging; stress-test with 35-50% down. - 38:00 – 40:00 | Long-Term Mindset
Match improvements to asset class; real estate is generational. - 40:00 – 41:30 | Sponsor Break: Sleep Sound Property Management
- 41:30 – 44:00 | Market Trends
Rise in “recapitalizations” as alternative to traditional seller financing. - 44:00 – 50:00 | Portland Market Deep Dive (Notable Moment)
Historic low values = buying opportunity, but offset by expenses and sentiment; regulations provide long-term balance. - 50:00 – 53:00 | Insurance and Stabilization
2023 challenges easing with new carriers for older buildings. - 53:00 – 57:00 | Personal Insights
Unplugging via DIY, golf, family; instilling self-belief in daughters. - 57:00 – End | Closing and Contact
You can reach Sean via a Google search or Colliers websi.te

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