What if your first big real estate win gave you false confidence for what came next?

Mike and Lijia Deaton walked away from corporate careers to build a land flipping business, and it worked. But when they expanded into multifamily syndications, things got more complicated. In this episode, they open up about what it really takes to run a land business like a business… and the tough lessons they learned trying to scale into bigger assets.

From spreadsheet optimism to investor stewardship, the Deatons share what’s worth chasing, and what they’d never do the same way again

🎙️ What we cover:

• Why land was the right entry point for their first business
• The overlooked discipline of mindset in real estate success
• How they structured their transition out of W2 jobs with a 12-month runway
• The truth about multifamily: floating rate debt, team dynamics, and where things go wrong
• How to evaluate partners before the pressure hits
• Why systems and boring operations still win the long game

The bold truth? In real estate, it’s not the deal it’s the operator that makes or breaks it.

Learn more about Mike & Ligia Deaton:LinkedIn:

• https://www.linkedin.com/in/michaelbdeaton/ YouTube:
• https://www.youtube.com/@mikeandligia web:
• https://flippingdirt.us/freedom/
  

🎧 Listen now: https://www.youtube.com/@TheRealEstatePessimist/videos 📍 Find us on all platforms

YouTube: https://www.youtube.com/@TheRealEstatePessimist/videos

Spotify: https://open.spotify.com/show/30iW9NGVaPVqIBZqf8iNd5?si=aa41afe7b90b4315

Apple: https://podcasts.apple.com/us/podcast/the-real-estate-pessimist/id1785003692

🎧 Want more from Kristi? Hear how she’s helping locals become developers in their own communities by removing the gatekeeping.

→ Listen to the Local Real Estate Developer Podcast: https://www.youtube.com/@LocalRealEstateDeveloper/podcasts

#realestateinvesting #mindsetshift #entrepreneurjourney #fearvsprudence #therealestatepessimist #developmentlife #propertyinvestor #startscared #riskandreward #truthaboutrealestate

If you’re not plugged into a real estate investor community, you’re missing the fastest way to grow your portfolio, find deals, and skip costly mistakes. The right real estate networking group can be a total shortcut connecting you to people, knowledge, and opportunities you’ll never get alone.

In this episode of The Real Estate Pessimist, Kristi and Erik break down the single most underrated hack in real estate: surrounding yourself with the right people. Not the “complain and coast” crowd… but a real investor community that pushes you to grow, makes you smarter, and brings deals straight to your lap.

We cover how to find them, how to make them work for you, and why knowing when to leave is just as important as joining in the first place.

What you’ll learn in this episode:

• The key differences between paid and free investor communities

• How to spot (and avoid) the time-wasters and tire-kickers

• The hidden ROI of paying to be in the right room

• Why entrepreneurship gets lonelier the more successful you become—and how to fix it

• Simple ways to build relationships that lead to actual opportunities

• How to create your own community if you can’t find the right one

• The signs it’s time to exit a group and move on
  

Bold truth: If you’re trying to do this alone, you’re already at a disadvantage.

🎧 Listen now: https://www.youtube.com/@TheRealEstatePessimist/videos 📍 Find us on all platforms:

YouTube

https://www.youtube.com/@TheRealEstatePessimist/videos

Spotify: https://open.spotify.com/show/30iW9NGVaPVqIBZqf8iNd5?si=aa41afe7b90b4315

Apple: https://podcasts.apple.com/us/podcast/the-real-estate-pessimist/id1785003692

🎧 Want more from Kristi? Hear how she’s helping locals become developers in their own communities by removing the gatekeeping.

→ Listen to the Local Real Estate Developer Podcast: https://www.youtube.com/@LocalRealEstateDeveloper/podcasts

#realestateinvesting #mindsetshift #entrepreneurjourney #fearvsprudence #therealestatepessimist #developmentlife #propertyinvestor #startscared #riskandreward #truthaboutrealestate

What do you do when a hurricane wipes out your dream just three months after you buy it?

Most people quit. Mike and Dawn didn’t.

In this episode of The Real Estate Pessimist, we share the raw, no-fluff story of two Midwest entrepreneurs who bought an iconic bar on Kristi’s home turf—Fort Myers Beach—only to watch it get annihilated by Hurricane Ian. But instead of walking away, they rolled up their sleeves, rallied a broken island, and started rebuilding something even stronger.

This isn’t just a comeback story.

This is what it looks like when locals lead.

💥 What we cover:

• How Mike and Dawn lost a business, then tripled their impact in the community
• The emotional (and financial) rollercoaster of post-disaster investing & rebuilding
• Why insurance isn’t a magic fix. Just ask their $8M rebuild
• The behind-the-scenes of navigating FEMA, permitting, and red tape
• What really motivates a local developer to rebuild when big players jump in.
• Why locals with grit are the future of community development

Truth bomb:

Storms will come. It’s not about what gets destroyed. It’s about who chooses to be resilient, get back up, and become a beacon of hope for those around them.

Contact info:

• https://www.thewhalefmb.com/
• Instagram: @thewhalefmb
• Facebook: facebook.com/thewhalefmb
• Dawn Miller on facebook
• dawnmiller@thewhalefb.com

🎧 Listen now: https://www.youtube.com/@TheRealEstatePessimist/videos📍 Find us on all platforms:

YouTube: https://www.youtube.com/@TheRealEstatePessimist/videos

Spotify: https://open.spotify.com/show/30iW9NGVaPVqIBZqf8iNd5?si=aa41afe7b90b4315

Apple: https://podcasts.apple.com/us/podcast/the-real-estate-pessimist/id1785003692

🎧 Want more from Kristi?

Hear how she’s helping locals become developers in their own communities by removing the gatekeeping.

→ Listen to the Local Real Estate Developer Podcast: https://www.youtube.com/@LocalRealEstateDeveloper/podcasts

#realestateinvesting #mindsetshift #entrepreneurjourney #fearvsprudence #therealestatepessimist #developmentlife #propertyinvestor #startscared #riskandreward #truthaboutrealestate

Ever wonder what seasoned investors wish they never did? And what they'd double down on in a heartbeat?

We’re pulling back the curtain and spilling the dirt on the deals we regret, the lessons we paid dearly for, and the five best decisions that changed everything.

This is the real stuff no one brags about on social media. The things we’d never do again, and the wins we’d fight for every time.

In this episode, we get raw about:

• Why we wish we started investing sooner

• The one thing we ignored (that almost wrecked everything)

• What we did with our primary homes that totally changed the game

• How the wrong partnerships and bad vetting cost us big

• What actually makes real estate worth it (and what doesn’t)
  

Truth Bomb: Sometimes the best move in real estate… is the deal you don’t do.

🎧 Listen now: https://www.youtube.com/@TheRealEstatePessimist/videos 📍 Find us on all platforms:

YouTube: https://www.youtube.com/@TheRealEstatePessimist/videos

Spotify: https://open.spotify.com/show/30iW9NGVaPVqIBZqf8iNd5?si=aa41afe7b90b4315

Apple: https://podcasts.apple.com/us/podcast/the-real-estate-pessimist/id1785003692

👀 Want to become a STR Expert with Erik’s help? https://eriks-academy.teachable.com/p/str-in-an-hour

🎧 Want more from Kristi? Hear how she’s helping locals become developers in their own communities by removing the gatekeeping.

→ Listen to the Local Real Estate Developer Podcast: https://www.youtube.com/@LocalRealEstateDeveloper/podcasts

#realestateinvesting #mindsetshift #entrepreneurjourney #fearvsprudence #therealestatepessimist #developmentlife #propertyinvestor #startscared #riskandreward #truthaboutrealestate

😬 Knowing when to walk away. That’s the real skill no one teaches.

In this episode of The Real Estate Pessimist, we sit down with Stephanie—flipper, coach, and proud survivor of one of the most emotionally expensive deals we've heard. She opens up about the flip that started with a $5,000 non-refundable earnest money deposit… and ended in a gut-wrenching lesson on ignoring red flags and losing more than just money.

Here’s what we cover:

- Why she knew she should walk from the deal… and didn’t

- The slippery slope from a $70K rehab to a new build

- How ignoring your instinct can cost you big time

- What to do when you're in breach of a hard money loan

- Why flipping isn't the same as building wealth- And how she bounced back with boundaries, clarity, and six flips a month!

🔥 Bold Truth:The $5K loss would’ve hurt. But the real cost came from not trusting herself.

🎧 Listen now: https://www.youtube.com/@TheRealEstatePessimist/videos

📍 Find us on all platforms:

YouTube: https://www.youtube.com/@TheRealEstatePessimist/videos

Spotify: https://open.spotify.com/show/30iW9NGVaPVqIBZqf8iNd5?si=aa41afe7b90b4315

Apple: https://podcasts.apple.com/us/podcast/the-real-estate-pessimist/id1785003692

Connect with Stephanie Lombardo:

Instagram @flippinempire

YOUTUBE: @iamstephlombardo

skool: https://www.skool.com/flippin-launch

👀 Want to become a STR Expert with Erik’s help?https://eriks-academy.teachable.com/p/str-in-an-hour

🎧 Want more from Kristi?Hear how she’s helping locals become developers in their own communities—without the gatekeeping.→ Listen to the Local Real Estate Developer Podcast:https://youtube.com/playlist?list=PLgKpTF3d5DZ1Mf6tpbxC3Uq9Lz899uohD&si=Tb530nMJfEQjR49E

#realestateinvesting #mindsetshift #entrepreneurjourney #fearvsprudence #therealestatepessimist #developmentlife #propertyinvestor #startscared #riskandreward #truthaboutrealestate

Ever feel like the government is just there to block your deals, stall your permits, and jack up your taxes? What if we told you the government could actually speed you up if you know how to play the game?

In this episode of The Real Estate Pessimist, we get into the good, the bad, and the ugly truth about working with the government in real estate. Erik and Kristi unpack how the government is your silent business partner whether you like it or not, and why ignoring them can tank your project or cost you a fortune.

We share the wins, the losses, and the times we got totally blindsided by shifting regulations (like that zoning mess in Maui 😳).

💥 What we cover:

• Why the government is your default partner in every real estate deal
• How to read the "weather forecast" of your city and predict regulation changes
• Real stories of projects that got shut down or fast-tracked
• How to build relationships with city officials (and why it matters)
• Insider tips on taxes, zoning, inspections, and permits
• The danger of “ask forgiveness later” strategies in real estate
• Grants, tax credits, and incentives most investors overlook

🎧 Listen now: https://www.youtube.com/@TheRealEstatePessimist/videos

📍 Find us on all platforms: YouTube: https://www.youtube.com/@TheRealEstatePessimist/videos Spotify: https://open.spotify.com/show/30iW9NGVaPVqIBZqf8iNd5?si=aa41afe7b90b4315 Apple: https://podcasts.apple.com/us/podcast/the-real-estate-pessimist/id1785003692

👀 Want to become a STR Expert with Erik’s help? https://eriks-academy.teachable.com/p/str-in-an-hour

🎧 Want more from Kristi? Hear how she’s helping locals become developers in their own communities by removing the gatekeeping.

→ Listen to the Local Real Estate Developer Podcast: https://www.youtube.com/@LocalRealEstateDeveloper/podcasts

#realestateinvesting #mindsetshift #entrepreneurjourney #fearvsprudence #therealestatepessimist #developmentlife #propertyinvestor #startscared #riskandreward #truthaboutrealestate

What do near-death climbs, 3 a.m. sewage emergencies, and a full-blown partnership rescue mission have in common?

They’re all part of Corey Harrelson’s wild real estate story — and we unpack every gritty, gut-wrenching, and somehow still inspiring detail in this episode of The Real Estate Pessimist.

Corey isn’t your typical investor. He doesn’t flex Rolexes or pitch you passive income fairytales. He buys “ugly” mobile home parks, deals with literal poop fires, and still comes out standing — not because it’s easy, but because he’s built for the climb.

🎯 Inside this episode:

• The real reason Corey walked away from a successful engineering career

• Why a Half Dome blizzard became the ultimate investor training ground

• The $50,000/month mistake that nearly cost him everything

• How one lender phone call changed the entire game

• The behind-the-scenes breakdown of mobile home park investing

• What syndicators and back-of-napkin pro formas don’t tell you
  

Takeaway truth: Real estate isn’t just about numbers. It’s about resilience. And sometimes… sewage.

🎧 Listen now

📍 Find us on all platforms

Youtube: https://www.youtube.com/@TheRealEstatePessimist/videos

Spotify: https://open.spotify.com/show/30iW9NGVaPVqIBZqf8iNd5?si=aa41afe7b90b4315

Apple: https://podcasts.apple.com/us/podcast/the-real-estate-pessimist/id1785003692

#RealEstatePessimist #MobileHomeInvesting #RealEstatePodcast #AffordableHousing #REIReality #PartnershipsMatter #PoopPlantFire #RealEstateFails #RealEstateResilience #CoreyHarrelson #DeveloperLife #REICommunity #PassiveIncomeMyth #BehindTheDeals #UnfilteredRealEstate

What if the thing you're most afraid of… is actually the thing you're supposed to do next?

In this raw and unfiltered episode, Kristi and Erik rip the mask off of fear — not to shame it, but to understand it. Because let’s be honest: fear’s gonna ride shotgun on your journey. The trick is not letting it drive.

We break down the difference between irrational fear and wise prudence, and more importantly — how to tell the difference when you're standing at the edge of a decision that could change everything.

Whether you’re thinking about quitting your job, buying that property, or finally launching that thing you keep talking about… this one’s for you.

In this episode:

• The real difference between fear and prudence (and why it matters)

• Our go-to fear assessment tools you can steal today

• Stories of leaving security behind to chase something better

• How to stop your ego from running the show

• Why calculated risk is the only kind worth taking

• What happens when you finally get brave enough to bet on yourself
  

💥 Real truth: You don’t need to kill fear to move forward. You need to learn how to listen to it without obeying it.

🎧 Listen now: https://www.youtube.com/@TheRealEstatePessimist/videos

📍 Find us on all platforms:

YouTube: ⁠Watch here⁠

Spotify: ⁠Listen here⁠

Apple: ⁠Tune in here⁠

📄 Free Fear Assessment Worksheet: Download the tool we use to make decisions with clarity → Access it here

👀 Want to become a STR Expert with Erik’s help? Jump in here

🏗 Ready to go from podcast listener to Local Developer with Kristi’s guidance? Programs, tools, and support to help you build what matters → localrealestatedeveloper.com

#realestateinvesting #mindsetshift #entrepreneurjourney #fearvsprudence #therealestatepessimist #developmentlife #propertyinvestor #startscared #riskandreward #truthaboutrealestate