What if the pursuit of success is what’s holding you back?
In this episode, Captain Curt sits down with Kassidy Warren, a San Diego-based investor and podcast host who built a $13M real estate portfolio starting with a $35 Airbnb listing. But after years of hustle, construction chaos, and ignoring his health, Kassidy hit burnout—and realized he’d built a business he no longer loved.
They unpack real estate strategies (why he says cash flow is overrated), mindset shifts, the power of subtraction, and how podcasting reignited his purpose. Kassidy also breaks down how leveraging coaching, therapy, and a complete calendar reset helped him become the most aligned version of himself.
This episode is a raw reminder that freedom doesn’t come from money—it comes from meaning.
Timestamps
00:00 – From $35 Airbnb to $13M in Real Estate
03:29 – Why Kassidy Launched "For Your Own Good" Podcast
05:45 – Real Estate Burnout & the Shift to Personal Growth
10:49 – Why He Cashed Out His 401k to Build Real Wealth
15:10 – The Breakdown That Sparked His Breakthrough
20:25 – Why Subtraction Creates Expansion
26:55 – “Cash Flow Is the Least Valuable Part of Real Estate”
33:43 – Why He Doesn’t Use 1031 Exchanges
34:52 – The Secret to Long-Term Real Estate Success
37:37 – Fear as a Signpost: How He Levels Up
43:08 – Building Teams vs. Knowing It All
49:09 – Kassidy’s Real-Life Calendar & Energy Strategy
CONNECT WITH US:
Instagram: @thecaptaincurt
TikTok: @thecaptaincurt
YouTube: https://www.youtube.com/@thecaptaincurt_
Website: www.captaincapital.com
Invest With Curt: Start Here: https://www.captaincapital.com/invest
CONNECT WITH KASSIDY WARREN:
Instagram: @kassidy.warren
TAGS:
#RealEstateInvesting #ShortTermRentals #MindsetMatters #BuildWealth #PodcastWithPurpose
CONNECT WITH US:
Instagram: @thecaptaincurt
TikTok: @thecaptaincurt
YouTube: https://www.youtube.com/@thecaptaincurt_
Website: www.captaincapital.com
Invest With Curt: Start Here: https://www.captaincapital.com/invest
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