What if your exit wasn’t the end—but the beginning of your best investments?

In this episode, Captain Curt sits down with his coworker and longtime friend Nathan Leathers, a business owner who successfully exited his company and turned his profits into a growing Section 8 real estate portfolio. Nathan’s journey is proof that you don’t need to chase trends—you just need a plan, patience, and the guts to follow through.
They talk business exits, buying back time, and why Nathan chose cash-flowing properties over luxury developments. He also shares what it’s like to own a Cirrus jet, how aviation changed his perspective on life, and why grounded investments matter more than flashy ones.

This episode is a powerful reminder that real freedom is quiet, intentional, and built to last.

Timestamps
00:00 – Generational wealth through real estate
05:34 – Early entrepreneurship and sales background
10:57 – Burnout and selling Kitchen Guard
16:39 – Real estate as a higher-level game
22:11 – Delaying fatherhood for financial goals
27:01 – Legacy planning for his daughter
30:35 – Structuring inheritance with intention
33:44 – Teaching financial discipline to kids
37:48 – Parenting challenges and values
41:25 – Dating your wife and family alignment
46:12 – Family dynamics and shared goals
51:38 – Why he chose Section 8 investing

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 NATHAN LEATHERS:
Instagram: https://www.instagram.com/nateleatherss/

TAGS:
#BusinessExit #Section8Investing #RealEstateFreedom #CirrusJetLife #PassiveIncomePath

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What if the easiest deals are the ones no one else is even looking at?

In this episode, Captain Curt sits down with Cole Ruud-Johnson, a real estate wholesaler who built a $20M+ off-market empire from cold calls, consistent follow-up, and creative seller conversations. He’s the founder of Easy Button Real Estate and leads a fast-growing community on Skool called Off Market Method.

They get into the weeds of offer structure, VA systems, building buyer lists, why Cole left the MLS behind, and how wholesalers can ethically scale without burning bridges. Cole also shares how travel, golf, and living slower actually made him a better dealmaker—and why good people win long-term in this game.

This episode is a tactical playbook for anyone looking to exit the rat race and go off-market.

Timestamps
00:00 – How Cole Got Started in Off-Market Wholesaling
03:31 – The $30k Deal That Changed Everything
06:29 – Why He Quit the MLS and Built His Own Buyer List
08:42 – Real Offer Structure Tips for Wholesalers
14:11 – Building a Scalable VA System That Works
18:54 – Why Follow-Up Is 90% of the Game
24:45 – How Cole Builds Trust with Sellers Without a License
30:12 – Mindset Shifts: From Hustle to Alignment
36:09 – Golf, Travel, and Life Outside the Grind
40:00 – Why Off-Market Is the Future of Real Estate Deals

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 COLE RUUD JOHNSON:
Instagram: https://www.instagram.com/coleruudjohnson
Easy Button Real Estate: https://www.easybuttonrealestate.com

TAGS:
#RealEstateWholesaling #OffMarketDeals #FinancialFreedom #ColdCallingWorks #EasyButtonRealEstate

P.S. If you're enjoying the show, do us a favor—leave a review and give us a 5-star rating. It's free, takes 30 seconds, and helps us reach more listeners who need this kind of no-fluff insight.

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

P.S. If you're enjoying the show, do us a favor—leave a review and give us a 5-star rating. It's free, takes 30 seconds, and helps us reach more listeners who need this kind of no-fluff insight.