Jasmine Greenwald 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 Stress).

Then we get into the real stuff: long-distance management, short-term vs. long-term rentals, insurance headaches, and contractor relationships—aka the part of real estate nobody brags about, but everyone eventually learns the hard way. Jasmine shares what she’s focused on next and the mindset that keeps her moving forward even when a project gets messy.

If you got value from this episode, follow/subscribe to REIA Radio, leave a quick review, and send this episode to a friend who still believes every contractor will “be there tomorrow.”

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...

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 (and structuring deals correctly) can open up opportunities without you doing every project yourself. They also get into marketing that actually moves the needle, including why consistency beats “perfect,” and why authentic content tends to win over polished, robotic posts.

On the operations side, they unpack the parts nobody puts on Instagram: tenants trying to bypass the property manager, tech issues that turn into lockouts, neighbor drama that escalates fast, and why having boundaries (and the right team) keeps you from being on-call 24/7.

They wrap with a quick debate on Airbnbs vs hotels, plus a teaser for an upcoming episode featuring an out-of-state short-term rental story packed with insurance and contractor headaches.

If you got value from this episode, follow the show and leave a 5-star written review—it helps more investors find the podcast.

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, 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—including a first flip that turned into a brutal (but useful) education: old houses, plaster and lath surprises, scope creep, hard money pressure, and the reality of paying for mistakes. He breaks down how he funded projects (including hard money and a 401k loan), what he’d do differently now, and how his strategy evolved from heavy DIY to “do less, hire more.”

We also get into what it looks like investing in today’s market—when properties don’t fly off the shelf in a weekend anymore. Jason explains why multiple exit strategies matter (flip, rental, midterm rental, etc.), how he handled a property that sat longer than expected, and what features can quietly kill demand even after a good rehab. And then there’s the townhome curveball: a deal that should’ve closed… until an HOA insurance problem nuked the finish line.

Along the way, there are some classic REIA Radio moments—like randomly getting a call from the very coach being credited for the entire journey… while recording live. Because apparently the universe has a sense of humor.

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/
...