REIA Radio

Jasmine Greenwaldt jumps on REIA Radio to share how she went from art professor to real estate investor—and why that shift made sense once she got serious about freedom, ownership, and building something that lasts. We talk about getting started, taking calculated risks, and what it’s like running rentals when you’re not down the street to “just stop by real quick” (because that’s how people end up with a new full-time job called S...

They kick things off with some end-of-year chaos and friendly trash talk, then shift into a serious update on a newly purchased Omaha property that’s being repositioned into long- and mid-term rentals. From there, the conversation turns into a mix of strategy, war stories, and lessons learned the hard way.

Owen and Ted break down hard money and private lending—what it is, why it matters, and how understanding the rules (an...

In this episode, we sit down with Jason Woodward and unpack a real-life investing journey that starts with flipping boats (yes, boats) and turns into building a real estate portfolio while still working a full-time W-2. Jason shares how learning the basics through coaching and community gave him the confidence to finally take action—and why the “right room” can speed up your timeline by years.

Jason walks through the early deals—inc...

In this Real Estate Rundown episode, Owen and Ted get into the practical side of AI—how tools like ChatGPT can help you spot your “zone of genius” (and your blind spots) so you can stop doing the work you secretly hate and start delegating like an adult. They share a solid prompt passed along from their buddy Colin Schwartz, compare “nice” AI vs “tell me the truth” AI, and talk about why unfiltered feedback can be a cheat code for ...

Jay and Ashley are back nearly 200 episodes after their first appearance, and they don’t sugarcoat what the last few years have looked like: raising a big family, trying to run a business together, and realizing how fast “life stuff” can spill into “work stuff.”

They get real about what’s working right now in the market—Zillow Preferred leads, staying in front of past clients, and being consistent even when motivation is nowhere to ...

In this episode, we break down what’s really going on with New York City’s housing crisis — from strict rent control and proposed rent freezes to a billion-dollar bailout for “distressed” landlords. We talk about how rising insurance, taxes, and maintenance costs crush owners when income is capped, and what happens when the city steps in with taxpayer-funded rescue plans. Is this sustainable, or are we just kicking the can down the...

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...

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, nation...

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 mo...

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 choosin...

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 (equ...

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 dema...

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 a...

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...

Jason “Wojo” spent years doing what entrepreneurs are told to do: grind harder, stack wins, chase the next deal, and assume life will sort itself out later. On paper, it worked. In reality, it cost him his marriage, his health, and his peace. In Episode 262 of REIA Radio, Wojo opens up about what happens when your definition of success quietly burns down everything that actually matters, and how he rebuilt his life by making his bu...

In this Halloween edition of The Real Estate Rundown, Owen and Ted break down why you shouldn’t sleep on land.

They walk through a real-world model where a specialized team handles everything—from finding and entitling the dirt to bringing fully leased, brand-new commercial bays online in about a year. You’ll hear how investors can step into turnkey triple-net projects, leverage pre-leased spaces, explore condo-izing bays, and use l...

In this episode, Ted and Owen sit down with Jennifer Newby, a fearless DIY homebuilder turned developer whose story proves that grit and curiosity can outbuild any limitation. From tearing down her first house with a sledgehammer to constructing luxury homes from scratch, Jennifer turned “learning as you go” into a full-fledged business model.

She shares how she and her husband built their first home using YouTube videos, library bo...

In this wild Real Estate Rundown, Ted Kaasch and Owen Dashner dive into the unpredictable world of real estate — and life. Between Ted’s Doberman swallowing a metal grill brush (yes, really) and Owen’s six-figure boiler replacement saga, this episode hits every note from chaos to comedy.

They share the hidden costs of major repairs, lessons from managing large multifamily buildings, and the headaches that come with insurance deadlin...

In this episode of REIA Radio, hosts Ted Kaasch and Owen Dashner dive into their recent adventures at two major real estate events — the National REIA Owners Conference and BP Con in Las Vegas.

Ted shares behind-the-scenes stories from meeting national speaker David Pickron and reveals how REIA groups nationwide are evolving. Owen breaks down his top takeaways from Chris Voss, including three negotiation “Golden Nuggets” that can ch...