😬 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

Think your contractor is out to get you?

What if the truth is… you just never spoke the same language to begin with?

In this episode, we sit down with Tyler Madden — a licensed GC turned investor turned truth-teller — who’s here to tell you what actually goes wrong on remodels, why most investors sabotage their own flips, and how to avoid the all-too-common contractor blame game. This one is full of hard truths, dry humor, and real-life bruises from the trenches.

Here’s what we get into:

• Why your contractor “screwed you” might just be code for you gave zero direction

• What Tyler learned after losing $200K (yes, actual money, not “missed upside”)

• Why real estate isn’t a finish line, it’s a practice

• The one shift that makes contractors WANT to go the extra mile for you

• The biggest myth investors believe about flipping

• How to set up your own scope of work — even if you’re not a GC

• Why active income businesses might just be the ultimate wealth hack

  
  

Hard truth:
Real estate isn’t a magic slot machine. It’s a messy, relentless, rewarding game — and only the self-aware survive.

🎧 Listen now: https://youtube.com/@therealestatepessimist?si=v6hw0PJVQ3QrFgrq

Find us on all platforms — link in bio

#realestatepessimist #remodeltruths #flippinghouses #generalcontractorlife #realestateinvesting #constructionfail #realestatelessons #houseflip #developmentwithoutgatekeeping #localrealestatedeveloper #thetruthaboutrealestate

💥 Thinking about teaming up on your next deal? Ask yourself this first: What happens when it ends?

In this episode of The Real Estate Pessimist, Kristi and Erik get into the realest real estate convo that nobody wants to have — what it takes to build a strong partnership... and how to prepare for the moment it might fall apart. From awkward money talks to who's actually unclogging the toilet at your Airbnb, we cover it all.

🧠 Here’s what we dive into:

• Why “I like you” isn’t a good enough reason to start a business

• How to ask awkward but essential questions before you partner up

• What roles, responsibilities, and expectations you need in writing

• Our own partnership stories — the good, the bad, and the “we’re still friends somehow”

• How to exit a deal without burning every bridge on your way out
  

Real talk: Ambiguity is the enemy of alignment. If it’s not in writing, it’s already a risk.

Find us on all platforms 👉 https://www.youtube.com/@TheRealEstatePessimist/videos

🎧 Link in bio!

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

Ready to go from podcast listener to Local Developer with Kristi’s guidance?

Whether you're just getting started or ready to go all in, we've got the tools to help you build what matters in your own backyard.

→ Programs & Resources:⁠ https://www.localrealestatedeveloper.com/⁠

#RealEstatePessimist #PartnershipsInBusiness #RealEstatePodcast #REITruth #BusinessBreakups #RealEstateInvesting #BehindTheScenesREI #PassiveIncomeMyth #KristiKandel #ErikStenbakken #InvestingWisdom #DeveloperDiaries #LocalDeveloperLife #RealEstateLessons

What if your biggest real estate wins came right in the middle of your worst life storms?

In this raw and real episode, we sit down with Jeff and Lexie—two powerhouse partners in business and marriage—who’ve flipped houses while flipping life upside down. PTSD, chronic illness, zero paychecks, and a truck window smashed by a random dude with a 2x4 (yes, really)... and somehow they still came out the other side stronger, together.

This isn’t just a story about live-in flips. It’s about:

• The REAL cost of doing real estate with your spouse

• Learning skills the hard way (YouTube University, anyone?)

• How trauma and hardship forced a change in direction

• The emotional toll of investing while the rest of life falls apart

• What true partnership looks like behind the scenes
  

This is the kind of episode we wish existed when we started. Not filtered. Not fabricated. Just the real journey.

🎧 Listen to the full episode now: https://www.youtube.com/@TheRealEstatePessimist/videos

Connect with Jeff & Lexie:

@jeffandlexie

@thecampfiremastermind

@stacheinvestor

www.bodenmullerproperties.com

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

Ready to go from podcast listener to Local Developer with Kristi’s guidance?

Whether you're just getting started or ready to go all in, we've got the tools to help you build what matters in your own backyard.

→ Programs & Resources: https://www.localrealestatedeveloper.com/

→ 90-Day Masterclass: https://www.localrealestatedeveloper.com/build-it-course

→ Apply for the Mentorship Program: https://www.localrealestatedeveloper.com/dev-mentorship

#realestatepessimist #realestatestory #marriedinvestors #liveinflip #truthaboutrealestate #flippinghouses #realestatepartnership #behindthescenes #overcomingobstacles #slowgrowth #communityovercompetition #buildtogether #propertyrehab #investingwhilemarried #realestatelife

Ever feel like you’re being sold to but can’t quite put your finger on it?

You probably just walked into a funnel — and surprise — you’re not alone.

But what if we told you that knowing where you are in the funnel could be the key to unlocking free value, high-impact connections, and even a shortcut to real results?

In this episode, Kristi and Erik pull back the curtain on funnels — the good ones, the shady ones, and how to make sure you’re in the right one for YOU.

We’re breaking down how marketing funnels really work in the real estate world, how to spot the traps, and how to walk through one with your eyes open.

In this episode:

• How real estate funnels are built (and how you’ve probably been in one)
• Kristi’s honest take on building her first funnel after 17 years of referral-only biz
• When free actually is valuable (and when it’s just bait)
• How to evaluate courses, masterminds, and coaches without getting burned
• Why asking better questions makes you a better investor
• What Fanta, fried wontons, and funnel hacks have in common (yes, really)

The only real shortcut in business: mentorship

Truth bomb: Being in a funnel isn’t the problem. Not knowing you’re in one is.

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

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

Ready to go from podcast listener to Local Developer with Kristi’s guidance?

Whether you're just getting started or ready to go all in, we've got the tools to help you build what matters in your own backyard.

→ Programs & Resources: https://www.localrealestatedeveloper.com/

→ 90-Day Masterclass: https://www.localrealestatedeveloper.com/build-it-course

→ Apply for the Mentorship Program: https://www.localrealestatedeveloper.com/dev-mentorship

#realestatepessimist #realestatementorship #honestrealestate #businessfunnels #investingtruths #localrealestatedeveloper #funnelstrategy #shortcutsmartnothard #growthmindset #realtalkrealestate

Congrats, You Just Made the Worst Financial Decision of Your Life What would you do if your own dad told you your first flip was a total disaster…

Right after you bought the house?

That’s exactly what happened to DJ Dubuono.

But spoiler alert: it turned out to be the start of everything.

In this episode, Kristi Kandel and Erik Stenbakken sit down with DJ—one of our Local Real Estate Developer alums—for a wild ride through live-in flips, family dynamics, bad drywall jobs, and the high-stakes lessons you only learn when the money’s already on the line.

This one’s for the people who are in it for real. No fluff. Just the truth.

What we cover:

Why live-in flips are either genius or insanity (or both)

How DJ’s dad predicted failure—and why he wasn’t entirely wrong

The DIY mistakes that turned into construction wisdom

The importance of managing expectations with contractors

How to document everything (or pay the price later)Scaling up flips and raising capital the real way

DJ’s first-ever sight-unseen deal—and the septic system scareWhat mindset, patience, and pessimism really look like in action

Truth bomb: Nobody cares about your project like you do. So either learn the details—or get ready to pay tuition.

Find us on all major podcast platforms. Search The Real Estate Pessimist New episodes every week.

This isn’t just about real estate. It’s about getting real.

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

Ready to go from podcast listener to Local Developer with Kristi’s guidance?

Whether you're just getting started or ready to go all in, we've got the tools to help you build what matters in your own backyard.

→ Programs & Resources:⁠ https://www.localrealestatedeveloper.com/⁠

→ 90-Day Masterclass:⁠ https://www.localrealestatedeveloper.com/build-it-course⁠

→ Apply for the Mentorship Program:⁠ https://www.localrealestatedeveloper.com/dev-mentorship⁠

#realestatepessimist #liveinflip #firstflipstory #contractorproblems #househackgonewrong #investortruths #realestateeducation #flippinghouses #localdeveloper #realtalkreels #entrepreneurjourney #realestatementorship #truthaboutrealestate

Think freedom means doing everything on your own?

Think again.

In this episode of The Real Estate Pessimist: The Good, The Bad, and The Truth About Real Estate Investing, Kristi Kandel and Erik Stenbakken get brutally honest about the mindset mistakes that keep entrepreneurs, investors, and business owners stuck in survival mode.

We dive into:

→ Why “I’ll just do it myself” is costing you time, energy, and growth

→ How to spot the hidden pain points you are creating by avoiding systems

→ Real examples of SOPs (Standard Operating Procedures) that buy your time back

→ How building simple systems can set you free to scale, breathe, and actually live your life

Freedom is not doing it all yourself.

Freedom is building the machine that does it with you.

🎧 Listen to the full episode now: https://www.youtube.com/@TheRealEstatePessimist/videos

Find The Real Estate Pessimist Podcast on all platforms

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

Ready to go from podcast listener to Local Developer with Kristi’s guidance?

Whether you're just getting started or ready to go all in, we've got the tools to help you build what matters in your own backyard.

→ Programs & Resources:⁠ https://www.localrealestatedeveloper.com/⁠

→ 90-Day Masterclass:⁠ https://www.localrealestatedeveloper.com/build-it-course⁠

→ Apply for the Mentorship Program:⁠ https://www.localrealestatedeveloper.com/dev-mentorship⁠

#RealEstatePessimist #KristiKandel #ErikStenbakken #RealEstateInvesting #EntrepreneurMindset #BuildTheSystem #OperationalFreedom #DelegationSkills #BusinessGrowth #SOPsForLife #RealEstateTruth #WorkSmarterNotHarder #EntrepreneurLife #RealEstatePodcast