

From Engineer To $13M Boutique Hotel Empire (In ONLY Five Years) w/ Kassidy Warren
Oct 10, 2025
Kassidy Warren, a former IT engineer turned real estate mogul, shares her inspiring journey of building a $13M boutique hotel empire in just five years. She discusses the common pitfalls engineers face in career transitions and emphasizes the importance of action over rumination. Kassidy details her pivot to real estate for financial freedom after living in a van and highlights strategies like leverage and creative financing. She also talks about the perks of hospitality investments over traditional rentals and the power of community in accelerating success.
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Engineer To Real Estate Transition
- Kassidy left corporate IT, did consulting, then started real estate investing because math made it feel safe.
- Engineers often overthink and talk themselves out of opportunities like investing.
Action Beats Rumination
- Rumination kills progress; action breaks the loop of overthinking.
- Kassidy urges writing goals down, speaking them aloud, then taking concrete steps.
Reframe Failure And Fear-Set
- Change your relationship with failure by mitigating downside risk instead of avoiding failure entirely.
- Use Tim Ferriss-style Fear Setting to list worst cases, likelihoods, and responses.