#264: Overcoming Life’s Toughest Challenge with AJ Osborne

REIA Radio

REIA Radio
#264: Overcoming Life’s Toughest Challenge with AJ Osborne
Nov 19, 2025 Season 1 Episode 264
Hosts - Ted Kaasch and Owen Dashner, Producer - Denlis Bertrand

A man goes into a coma, wakes up totally paralyzed, gets fired from his job in the hospital… and somehow his investments are doing better than before.

In this episode, AJ Osborne walks us through the day his body shut down from Guillain-Barré syndrome, what it felt like to wake up trapped in his own head, and the moment he realized his real estate investments were quietly keeping his family afloat while he fought to stay alive. He talks about the guilt, the pain, the look on his kids’ faces the first time they saw him in the ICU—and the pride of knowing he’d built something that took care of them when he couldn’t.

From there, we dig into how that experience reshaped his entire mission: why he doubled down on self-storage, how he built a business that works without him, and why most people are stuck on the “earn a paycheck, hope it works out” treadmill. AJ breaks down supply and demand in housing and storage in plain English, what investors get wrong about cycles, and why owning assets (not just having a job) is the real line between security and chaos.

We also get into working with family (without blowing it up), why the education system trains employees instead of owners, and how younger investors can still win in a world of high prices, high rates, and wild inequality—if they’re willing to change the playbook.

If this conversation punches you in the gut a little, don’t just nod and move on. Share this episode with someone who’s depending 100% on their job, then take one concrete step toward owning an asset this week—no matter how small. To learn more or connect with AJ, visit cedarcreekcapital.com or find him on Instagram and YouTube by searching “AJ Osborne Self Storage” or “Cedar Creek Capital.” And make sure you’re subscribed to REIA Radio and plugged into your local REIA so you’re not trying to figure this game out alone.

You can Join the Omaha REIA - https://omahareia.com/join-today
Omaha REIA on Facebook - https://www.facebook.com/groups/OmahaREIA
Check out the National REIA - https://nationalreia.org/
Find Ted Kaasch at www.tedkaasch.com
Owen Dashner on Facebook https://www.facebook.com/owen.dashner
Instagram - https://www.instagram.com/odawg2424/
Red Ladder Property Solutions - www.sellmyhouseinomahafast.com
Liquid Lending Solutions - www.liquidlendingsolutions.com
Owen’s Blogs - www.otowninvestor.com
www.reiquicktips.com
Propstream - https://trial.propstreampro.com/reianebraska/
Timber Creek Virtual - https://timbercreekvirtual.com/services/
MagicDoor - https://magicdoor.com/reia/
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Episode Artwork #264: Overcoming Life’s Toughest Challenge with AJ Osborne 1:52:50 Episode Artwork #263: The Real Estate Rundown with Owen and Ted 20:53 Episode Artwork #262: From Burnout to Lifeonaire: Designing a Business That Serves You with Jason Wojo 1:15:49 Episode Artwork #261: The Real Estate Rundown with Owen and Ted 29:01 Episode Artwork #260 The Self-Made Developer: Building Wealth One Nail at a Time with Jennifer Newby 1:13:52 Episode Artwork #259: The Real Estate Rundown with Owen and Ted 31:12 Episode Artwork #255: The Real Estate Rundown with Owen and Ted 21:58 Episode Artwork #254: From the Street Corner to the Boardroom: The Rise of John Uhrich 1:08:28 Episode Artwork #258: Navigating Life’s Challenges Through Real Estate: The Journey of Ian Ziegler 1:28:13 Episode Artwork #256: David Pickron: The Private Investigator’s Guide to Smarter Landlording 1:34:24 Episode Artwork #257: The Real Estate Rundown with Owen and Ted 21:50 Episode Artwork #253: The Real Estate Rundown with Owen and Ted 20:20 Episode Artwork #252: From Corporate to Real Estate: A Journey of Transformation with Liz Bono 1:17:33 Episode Artwork #251: The Real Estate Rundown with Owen and Ted 24:42 Episode Artwork #250: Growing Smart: Systems, Timing, and Avoiding Investor Burnout with Wyatt Simon 1:03:19 Episode Artwork #249: The Real Estate Rundown with Owen and Ted 46:28 Episode Artwork #248: Networking Your Way Into Deals, Markets, and Momentum with Collin Schwartz 54:15 Episode Artwork #247: The Real Estate Rundown with Owen and Ted 52:46 Episode Artwork #246: Creative Deal Structures, Legal Strategies & Raising Capital Like a Pro with Chris Pomerleau 1:11:43 Episode Artwork #245: The Real Estate Rundown with Owen and Ted 48:16 Episode Artwork #244: Professional Property Management Systems for 5–25 Unit Success with Andy Kouri 59:02 Episode Artwork #243: The Real Estate Rundown with Owen and Ted 48:10 Episode Artwork #242: REIA Mastery Series Special Episode: Ancillary Income & CEO Mindset – with Jeri Schlickbernd 58:35 Episode Artwork #241: The Real Estate Rundown with Owen and Ted 23:00 Episode Artwork #240: Beyond the Grind – Byron Thompson on Beating Burnout in Real Estate 48:59