This is Part 1 of our deep dive with Jay Kathol and Ashley Wells, and it’s a masterclass in what really happens behind the scenes of bigger real estate deals. Jay and Ashley walk through the highs and gut-punch lows of taking on a 40-unit multifamily, why their due diligence grade was a hard “C-minus,” and what they’d do differently before ever touching another boiler building again.

They talk legacy properties, inheriting a deal from family, and why sometimes singles and doubles beat swinging for home runs. You’ll hear how they started navigating bad tenants, contractor issues, surprise capital expenses, and a property with a rough reputation—plus how creative financing and buying the LLC instead of just the asset set the stage for what comes next in Part 2.

If you’re thinking about scaling into bigger multifamily or commercial, start with this episode so you don’t learn these early lessons the hard (and expensive) way.

👉 Listen in, subscribe, and share this with a partner or spouse you’re investing with so you’re on the same page before your next big deal.

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/
...

In this episode of REIA Radio, Owen and Ted kick things off with Thanksgiving chaos—bad smokers, ceiling fans from hell, and why home projects always take twice as long as you think. From there, they shift into real estate mode, talking through appraisal delays on Ted’s car wash deal and how that impacts loan timelines and decision-making.

They also break down the real value of REIA membership, including Home Depot discounts, national sponsor perks, and why most investors are quietly leaving money on the table by not using the benefits they already pay for. Ted shares the upcoming Omaha REIA price increase and how to lock in the lower rate before it changes.

To wrap it up, they tease an upcoming follow-up interview with past guests Jay Kathol and Ashley Wells—diving into how much can change in just a few years, what went right, what went wrong, and how their portfolio and perspective have grown since their first appearance.

If you’re serious about building your network, cutting your costs, and leveling up as an investor, plug into your local REIA, grab your discounts, and make sure you’re subscribed so you don’t miss Wednesday’s episode with Jay and Ashley

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/
...

In this episode, the guys sit down with marketer and founder of Entrepreneur Addict, Matt Tompkins, to unpack the surprising overlap between addiction and entrepreneurship. They talk about the denial entrepreneurs live in (“I don’t need help,” “I can do it all myself”), the fear of stepping away from the business, and what it really takes to build something that can run without you burning out in the process.

Matt breaks down how most business owners are getting ripped off by marketing agencies, the red flags to watch for, and why you should stop chasing viral reels and start focusing on three simple things: your Google Business Profile, YouTube, and AI search. He explains how to demand real reports, track actual conversions (not vanity metrics), and build a brand that people trust before they ever pick up the phone.

They also get into mental health, addiction, and the pressure of carrying a business on your back. Matt shares pieces of his own story, why entrepreneurs are especially prone to addictive behavior, and how telling your story openly can become your most powerful marketing asset—not just for leads, but for your own freedom.

If you’re a business owner who feels overwhelmed by marketing or burned by agencies, check out Matt’s self-paced Entrepreneur Addict marketing roadmap—built specifically for entrepreneurs with busy, distracted brains—at entrepreneuraddict.com/REIA.

If this episode hits home, share it with another entrepreneur, hit subscribe, and leave a review so we can reach more people who need to hear it.

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/
...

In this Real Estate Rundown, Owen and Ted break down the marketing lessons they pulled from their fast-paced interview with Omaha marketer and former radio personality Matt Tompkins. They dig into why most agents and investors are wasting time on social platforms their actual customers never see, and why your Google Business Profile might secretly be the most valuable “social feed” you own. You’ll hear how Matt thinks about choosing the right marketing channels, what to watch for so you don’t get ripped off by a marketing agency, and how fractional CMOs can give you pro-level results without hiring in-house.

The guys also swap stories from the trenches—city inspections, cursed/skunked units, slow-bleed project delays, and the mental chaos that comes with leveling up into new asset classes and big developments. It’s a mix of practical marketing strategy, real-world development headaches, and honest talk about staying (somewhat) sane as an entrepreneur.

After you listen, go update your Google Business Profile with fresh photos and posts, then share this episode with another entrepreneur who’s drowning in marketing “busy work” and needs a clearer game plan. And if this episode helps you, leave Owen and Ted a 5-star review so more investors can find the show.

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/
...

This episode is a replay from our live Omaha REIA event in early November, where Ted brings back Casey Gregersen—Wyo Houses and Bighorn Capital—for a deep dive into the Revive Method, the strategy his team is on track to use for 100 flips and roughly $5M in revenue with dramatically reduced risk.

Casey breaks down how investors, wholesalers, and private lenders can all plug into this model by using the “Big 3” filters (equity, time, and value-add), structuring deals so the seller shares in the risk, and baking his profit directly into the rehab budget instead of gambling on an uncertain ARV. He walks through real case studies, the underwriting spreadsheet he uses, and why this approach protects you when interest rates, comps, or contractors don’t cooperate.

You’ll also hear Casey’s story—going from W-2 at Shell to 400+ units, 70–100 flips a year, and still coaching his kids’ teams—and how systems, processes, and a clear “why” (choosing family over work) shaped the way he now builds businesses and helps other investors do the same.

If you’re a fix-and-flipper tired of skinny margins, a wholesaler sitting on “almost” deals, or a lender looking for better-protected opportunities, this episode gives you a playbook you can start using on your very next lead.

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/
...

In this Real Estate Rundown, Ted and Owen go off on one of the most painful parts of investing right now: appraisals and lenders changing the rules mid-game. From Ted’s delayed car wash deal and wasted appraisal fees to Owen’s stories of last-minute down payment shocks and nonsense tax assessments, they break down how shaky appraisals can wreck your timeline, your budget, and your blood pressure. You’ll hear why today’s market demands tighter underwriting, multiple exit strategies, and when it’s time to bring in a commercial loan broker instead of begging one bank to make sense.

They wrap by teeing up flipper and systems nerd Casey Gregersen, who’s coming back for the Fix & Flip Mastery Series to go even deeper into how he structures deals and scales his volume. If you’re an active investor, this is your reminder to stop counting on perfect appraisals—and start building smarter financing and backup plans into every deal.

If this episode hits a nerve (or saves you from a bad deal), share it with another investor who’s fighting their lender, and grab your seat for the next REIA Mastery Series workshop at http://reiamasteryseries.com/

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/
...

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/
...

This Real Estate Rundown gets personal. Owen and Ted talk through a serious health scare, the nightmare of dealing with the healthcare system, and what happens to your family, your money, and your peace of mind when your body suddenly taps out. Out of that mess came a promise: never again be financially exposed like that.

They break down how real estate investing became the vehicle to keep that promise – not as some hype-y “get rich” play, but as a way to build boring, reliable income that still shows up when life falls apart. If you’ve ever wondered whether all this grind is actually worth it, this episode will punch you in the chest in the best way.

If you want to go deeper on flipping, grab your ticket to The Fix & Flip Formula at reiamasteryseries.com or through the calendar at OmahaREIA.com before prices feel cheap in hindsight.

If it hits home, share it with someone who needs to hear it, leave us a 5-star review on Apple Podcasts, and follow REIA Radio on YouTube, Facebook, and Instagram so you don’t miss future episodes.

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/
...