Pivoting into real estate is harder in 2026 than it was a decade ago, but the opportunity is still there for anyone willing to be honest about their skills and their market.
In this episode, host Chris Lopez sits down with Tripp Gordon, who recently walked away from nearly a decade in software and venture-backed tech. Tripp owns two long-term rentals and is now trying to build a real estate career that pays the bills today while funding a longer-term portfolio. He came in with sharp questions, and Chris answered them from the seat of someone who has already lived through the same pivot.
Chris walks through the four things that need to line up before starting any new venture: market conditions, your actual skill set, your genuine desire, and your available capital. Skip any one of them and the odds get worse. He explains why liquidity separated the investors who kept going from the ones who got washed out, why Denver is in a slower phase while other metros run, and where that gap creates opportunity for patient buyers. Chris also shares a friend’s west-side six-unit flip that returned roughly 3x in nine months, makes the case that multifamily is bottoming, and pushes back on the “never sell, never pay taxes” mindset that leaves so much wealth creation on the table.
In this episode we cover:
- Why pivoting into real estate needs market, skill, desire, and capital working together
- How to tell burnout from the normal grind of building something
- What actually happened to multifamily syndications and why the setup looks different now
- A friend’s west-side Denver six-unit flip that returned roughly 3x in nine months
- Whether the real estate agent path is still worth pursuing in 2026
- Day jobs inside real estate that give you a knowledge edge, from fund accounting to asset management
- Why “never sell, never pay taxes” deserves a harder look
- Chris’s mother-in-law suite conversion and house hacking at every life stage
Watch the Youtube Video
Timestamps
01:30 – Meet Tripp Gordon, pivoting from tech into real estate
05:09 – Chris’s four-part framework for any pivot
09:25 – How to tell “I hate this” from “this is just the hard part”
13:10 – Who survived the end of the easy era
18:44 – Multifamily distress and where opportunity is now
26:30 – Is the real estate agent path still worth it?
32:01– Day jobs that give you a real estate knowledge edge
41:56– Why “never sell” is worth rethinking
Links in Podcast
Contact Tripp Gordon: [email protected]
Property Llama Capital: https://capital.propertyllama.com/
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