In this Halloween-timed episode of the Generations of Wealth Podcast, Derek talks with John Todderud, founder of Cardinal Oak Investments, about transitioning from a 20+ year tech career into multifamily real estate, scaling nationally through property managers, and why he believes today’s difficult market — high rates, cautious investors, and spotty oversupply — is actually a good time to buy.
Watch the episode here
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📄 Summary
John Todderud spent decades in software and IT consulting before buying his first small multifamily properties (a 3-unit, then a 4-unit) just after the 2008 crash, after deciding fix-and-flip’s one-time payout and renovation-cost risk wasn’t for him. He self-managed those first properties close to home, then deliberately bought farther away and hired property managers once he wanted to step back from day-to-day management — a shift that eventually let him invest anywhere in the US based on market fundamentals like population growth, job growth, and landlord-friendly regulation (something he says has steadily worsened in his home state of Washington). He shares a property manager horror story: discovering, only after a tenant committed a violent crime against another tenant, that the manager had never run a background check — the final straw that led him to replace them. Looking at today’s market, John sees interest rates (with the 10-year treasury hovering around 5.2%) and uneven oversupply (Austin and Houston hit hardest, while markets like Fayetteville, NC stay strong) as the two biggest drags on multifamily, alongside investors who no longer have 1031-exchange proceeds to reinvest since many recent sales break even or lose money. Despite the hesitancy, he argues this is exactly the kind of market where patient, well-capitalized buyers build the best long-term returns, targeting cap rates of 6-7% as a healthy range while watching for both the risk and opportunity hidden in 8-9%+ distressed deals. He closes by making the case that real estate rewards almost any professional background, since the real skill is being comfortable solving numbers-based problems and taking control of outcomes a 401(k) never gives you.
⭐ Key Takeaways
- Fix-and-flip’s one-time payout and renovation-cost risk pushed John toward multifamily’s more predictable cash flow from the start.
- Buying farther from home and hiring a property manager is often the real unlock for scaling beyond a handful of properties.
- Once you’re working through a property manager by phone, your buy box can expand to any market in the country with strong fundamentals.
- Landlord-friendly (or unfriendly) regulation varies enormously even within one state — know the specific city or jurisdiction’s rules before buying.
- Always confirm your property manager is actually running full background checks — referrals and reputation aren’t a substitute for verifying the basics yourself.
- A quick cash-for-keys offer can resolve a problem tenant situation far faster and cheaper than a formal eviction.
- Today’s oversupply is uneven — some major metros (Austin, Houston) are struggling while smaller markets (like Fayetteville, NC) stay strong with no supply overhang.
- Fewer investors have 1031-exchange proceeds to reinvest right now, since many recent property sales are breaking even or losing money.
- A healthy cap rate target is roughly 6-7%; anything much below 6% carries thin margins, while 8-9%+ often signals real distress — which can be either a risk or an opportunity depending on the cause.
- People invest in the operator as much as the property — market selection, renovation execution, and cycle timing are where an experienced operator earns their return.
- Almost any professional background (teacher, nurse, firefighter, pilot) transfers useful skills into real estate investing — the real requirement is comfort solving problems and taking ownership of outcomes.
💬 Relevant Topics Discussed
- Multifamily real estate investing
- Transitioning from a corporate/tech career into real estate
- Property management & remote portfolio scaling
- Landlord-tenant regulation by market
- Tenant screening & background checks
- Cash-for-keys negotiation
- Current multifamily market conditions (rates, supply, investor sentiment)
- Cap rate analysis
- Operator selection in syndications
- Market cycles & timing
🏚️ Halloween Horror Story: The Property Manager Who Skipped a Background Check
A standout moment from the episode is John’s account of a property manager calling to report that one tenant had committed a violent crime against another. When he followed up to ask about the offending tenant’s background check, he learned none had ever been run — despite the manager coming with strong referrals. It’s a reminder that reputation and referrals aren’t a substitute for actually verifying a property manager’s basic practices, and the mistake was serious enough that John began searching for a replacement immediately.
🎧 Why Should You Listen?
This episode is equal parts cautionary tale and market outlook. John’s honest accounting of property management failures (including one with real safety consequences) offers lessons any rental property owner can apply right now, while his read on today’s multifamily market — high rates, patchy oversupply, and cautious capital — gives a grounded, specific picture of where opportunity is (and isn’t) heading into 2027. It’s also an encouraging listen for anyone wondering whether their non-real-estate background disqualifies them from investing; John makes a clear case that it doesn’t.
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About John Todderud
John Todderud is a full-time multifamily investor and syndicator who focuses on underwriting, sponsoring, and capital raising for deals. He began in real estate during his software and technology career, buying multifamily real estate. First smaller properties, focusing on finding vendors to repair, improve, and manage, then shifting his focus to partnering with real estate investors to acquire larger properties. His team acquires properties in emerging markets where rental demand is strong, the community is growing, and tactical renovations drive rent growth. They invest in properties which are stable but in need of modernization – good locations, attractive qualities but dated interiors or operational distress. Those are opportunities to improve lives by improving communities.