What happens when success nearly destroys you?
In this episode, Blake Anthony Carter and Jeremy Courtney open up about the darkest season of their business — how a $30,000-per-month loan nearly bankrupted them and what it took to fight their way back. From couch-surfing to managing 100+ short-term rentals, their story is a masterclass in grit, integrity, and redemption.
Here’s what you’ll learn:
This is more than a business story — it’s proof that the hardest moments can build the strongest foundations.
Timestamps
02:23 – The 2008 crash that shaped Blake’s view of risk
04:55 – How his mom’s resilience became his playbook for success
07:21 – The moment they realized STRs could replace their day jobs
13:10 – How EOS changed their business (and their relationship)
15:31 – Why reputation and relationships matter more than profit
19:21 – The new rules for STR success: quality, design, and service
25:24 – Austin’s market reset and how to spot real opportunities
35:03 – The $30K-a-month loan that almost bankrupted them
39:41 – How a hard money lender’s trust saved their business
41:19 – The mindset that kept them from walking away
43:05 – The unpopular truths about real estate investing
54:03 – The regrets, lessons, and books that shaped their comeback
CONNECT WITH BLAKE ANTHONY CARTER:
Instagram: https://www.instagram.com/blake.anthony.carter
Website: https://www.cribsconsulting.com/
CONNECT WITH JEREMY COURTNEY:
Instagram: https://www.instagram.com/thejeremycourtney
Website: https://www.cribsconsulting.com/
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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