In this episode of The Stash Cast, Karl Krakoff shares his journey from healthcare strategy executive to multifamily real estate operator in Washington State. With over 100 units under management, Karl walks us through how he transitioned from live-in flips to full-scale developments and value-add multifamily investments—while navigating the complexities of zoning laws, rent control, and managing operational expenses.
🎙️ Key Insights & Takeaways:
💼 Corporate Exit Strategy: Karl left a decade-long career in healthcare to build freedom through real estate, starting with house hacking and scaling through flips, joint ventures, and syndications.
🏘️ From Flips to Ground-Up Construction: Limited access to capital pushed him toward flipping and eventually led to new construction projects—including learning curves with permits, inspections, and project delays.
🛠️ Tech-Driven Property Management: Karl uses platforms like AppFolio and Buildium and leverages ChatGPT to triage maintenance issues before dispatching contractors, saving time and cost.
📉 Rent Control Realities: Operating in Seattle means factoring rent caps and tenant rights into every business plan. Karl discusses how this disincentivizes developers and investors—and what needs to change.
🧠 AI in Permitting? Karl and host Stash explore how AI and machine learning could drastically reduce permitting timelines and inefficiencies in city review processes.
🏃♂️ Daily Discipline & Mental Clarity: Karl credits his fitness routine—especially trail running—for sharpening discipline, building mental resilience, and staying focused as an entrepreneur.
🚀 Whether you're a real estate investor, developer, or just curious about how to scale from flips to multifamily portfolios, this episode is full of practical insights and honest takes on the current market.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thestashcast.substack.com/subscribe
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