In this episode, Derek sits down with self-storage powerhouse Jacob Vanderslice, who went from flipping houses in the mid-2000s to owning 41 self-storage facilities, 21,000 units, and 3.5M+ sq ft across 15 states.
Jacob breaks down:
• How he survived multiple market cycles
• Why self-storage is still strong despite economic uncertainty
• How to raise capital the right way
• What investors are doing wrong in today's market
• Why transparency and discipline matter now more than ever
This is a straight-talking conversation packed with real-world lessons on scaling, managing risk, surviving downturns, and building a durable real-estate business.
Cycles Create Wealth — Experienced investors make their biggest gains during market dislocations, not booms.
Self-Storage Thrives on Mobility — Demand is tied to people moving. As movement returns, storage demand will rise.
The Biggest Issue in 2024–2025: Debt — Rising rates, floating loans, and debt maturities are crushing poorly structured deals.
Transparency Wins Investors — Deliver bad news faster than good news. Investors value honesty over perfection.
Don't Force Deals — In tight markets, the winners are the ones who wait for great deals, not "make the numbers work."
Operational Excellence Matters — In today's environment, execution and downside protection matter more than projections.
Take Action — The worst thing a new investor can do is nothing. There's no perfect deal, only well-structured ones.
Evolution from flips → development → commercial → self-storage
Market cycles, interest rates, and macro pressures
Investor relations, reporting, capital raising challenges
Overpaying, rookie mistakes, and "selling the dream" deals
Operational headaches (break-ins, staff, overhead, U-Haul damages)
Sustainable business building vs. chasing scale
Finding off-market deals vs. broker relationships
Structuring investor equity, preferred returns, and K-1 benefits
Risk management and avoiding unsustainable models
Why action beats perfection for new investors
This episode is for you if:
You're an investor who wants to survive — and thrive — in a shifting market.
You want to understand the real economics behind self-storage.
You're raising capital (or want to) and need to understand what LPs fear most right now.
You've lost deals, money, momentum, or confidence — and want a roadmap forward.
You want unfiltered truth from two investors who have been through the fire and came out stronger.
00:00 – Intro & Derek opens the show
01:10 – Jacob's background & early real estate lessons
03:30 – Transition into self-storage & scaling nationwide
05:45 – Market challenges in 2024–2025
07:20 – Macro trends, demand softening & economic uncertainty
10:50 – Why storage demand dropped
13:05 – Derek on "thinning of the herd" in real estate
15:40 – Investor mistakes & overpriced deals
18:20 – Raising capital in today's environment
19:40 – LP pain: equity wipes, capital calls, paused distributions
22:05 – Transparency & communicating with investors
26:15 – How Jacob sources deals (off-market + brokers)
28:20 – Ideal deal size & investment parameters
29:50 – How investor structures work (pref, equity, K-1s)
31:30 – Managing 427 investors & reporting systems
33:10 – Team size & operational setup
36:20 – Not forcing deals & staying disciplined
38:00 – Hard money lending parallels & risk cycles
39:20 – Reality of storage operations (not passive)
40:20 – Jacob's advice: take action, take smart risks
41:30 – Political uncertainty & market psychology
43:45 – Derek's final send-off
Derek and guest Jacob Vanderslice dive deep into the mindset and mechanics behind building a durable real-estate business — specifically self-storage. Jacob shares how he went from fighting fires to building a multi-state storage empire by surviving market cycles, raising capital responsibly, and developing systems that scale.
They discuss the current market environment, rising rates, cracks in the economy, deal flow challenges, overpriced assets, and investor fear. Jacob explains why transparency and delivering bad news quickly is critical when managing investor capital, and why operational excellence matters more now than ever.
The conversation also covers sourcing off-market deals, building long-term investor trust, managing a large operations team, navigating overhead, and avoiding the pitfalls that wipe out rookies. The episode ends with timeless advice: take action, take smart risks, and don't wait for the perfect deal.
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