🔥 Someone Tried to BLOW UP His Investment?! | Real Estate Pessimist Podcast ft. Mike Sgandurra🚨

Has the ATF ever called you about one of your real estate deals?Didn’t think so.

But that’s just another day in the investing life of Mike Sgandurra — and in this episode, things get unhinged in the best way.

From a near-bombing of his Cybertruck 🚛💥 to a 4-year-long out-of-state reno gone off the rails — Mike's story is the chaotic cautionary tale every investor needs to hear so you can avoid similar challenges.

Join co-hosts Kristi Kandel and Erik Stenbakken as they dive into:

🔧 Turo hacking gone sideways

🏚️ The 4-year rehab project from hell

🧠 The mindset it actually takes to survive

📉 Why playing the long game is the only way outThis one’s not just about real estate.

It’s about resilience, risk, and how to keep moving when everything goes to sh*t.

👉 Listen now.

🎧 New episodes weekly on The Real Estate Pessimist Podcast — where we tell the good, the bad, and the TRUTH about real estate investing.

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 #RealEstatePodcast #RealEstateInvesting #InvestingStories #REICommunity #PodcastGuest#TheGoodTheBadTheTruth #WTFRealEstate #TuroNightmare #CybertruckDrama #NotJustTheHighlights #RentalFails #CarHacking #ResilientAF #ThisReallyHappened

Would you learn how to drive by watching Fast & The Furious?

Then why are so many people learning real estate investing from Instagram reels and TikTok gurus?

In this episode of The Real Estate Pessimist: The Good, The Bad, and The Truth About Real Estate Investing, Kristi Kandel and Erik Stenbakken break down hyperreality — the blurry line between what’s real and what’s just for show in the real estate world (and life).

We’re pulling back the curtain on: → Fake door counts → Burnout business models → Curated social media highlight reels → Chasing goals that aren’t even yoursThis is the stuff nobody talks about — but everyone needs to hear.

Because in real life? There are no stunt doubles. No filters. No shortcuts.

Just the truth about building a real estate business (and life) that actually fulfills you — not just looks good online.

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

#realestateinvesting #RealEstatePessimist #KristiKandel #ErikStenbakken #Hyperreality #RealEstateTruth #RealEstatePodcast #InvestingAdvice #SlowGrowth #AuthenticLiving #Entrepreneurship

What happens after the big win? After the exit, the accolades, the passive income?

In this no-BS episode of The Real Estate Pessimist Podcast, Kristi Kandel and Erik Stenbakken sit down with Keith Blackborg— CPA, high-net-worth advisor, real estate investor, and the guy whose team bought 875 houses.

But this isn’t just a flex-fest—it’s a soul check for every investor out there.

💥 We talk divorce scares and treasure chest proposals.

💥 Wealthy clients who looked rich but felt empty.

💥 What really happens when you sell your business and lose your identity.

💥 The painful truth behind hotels, hedges, and hustle culture.

💥 Plus, his 8 Portfolio Guidelines that could save you millions in regret.

Keith doesn’t hold back. From almost getting stabbed in a foreclosure to walking away from it all—this one hits differently.

If you’ve ever asked:

“What’s my enough number?”

“Why am I still grinding?”

“How do I build real wealth without losing my soul?”

Then pause the highlight reels. And hit play on this.Because this is the real talk behind the spreadsheets. And it might just be the most valuable hour of your year.

#HustleCulture is loud. But so is your inner voice saying, “There’s gotta be more.” This is that “more.”

👀 Watch now and share with someone who’s chasing more but might be missing what matters.

The Real Estate Pessimist Podcast

👉 The Good, The Bad, and the TRUTH about real estate investing.If you're into #RealEstateTruth

Connect with Keith:

https://www.financialjourney.life/

https://passiveinvestorevent.com/

https://www.linkedin.com/in/keithblackborg/

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

#WealthWithoutBurnout, and #FinancialFreedom with depth, this episode is for you.#PassiveIncomeRealityChecks

#WorkOptionalGoals #MarriageAndMoney #IdentityAfterExit #PortfolioProtection

The One Thing That Almost Every Successful Investor Ignores | EP#15

✨ Must-watch for anyone who's ever thought "I'll be happy when..." 💥

Spoiler alert: that moment never comes.In this episode, Kristi Kandel and Erik Stenbakken drop the truth bomb that nobody in the real estate game wants to admit—success is boring.

No flashy cars. No 100 doors in 6 months. Just the same hoodie, same systems, same daily habits… repeated for years.

We talk about:

*Why Erik wore the same “mechanic” shirt for two decades—and how it made him wildly successful

*Kristi’s moment of “making it

” (dock, dolphins, dream house) and why it still didn’t feel like enough

*How boring, repetitive consistency is the actual superpower of successful investors

*Why “more doors” might be killing your freedom

*The dangerous illusion of “arriving” and how social media has us all chasing mirages

*How to define YOUR version of success (spoiler: it might look like daily walks with your dog and no one blowing up your phone)

This one’s not just for newbie investors. It’s for anyone who’s already in the game and wondering if there’s more to life than chasing the next deal.

📉 Real talk. No fluff. No fake flexing. 📈 Just the good, the bad, and the TRUTH about real estate investing.

👉 If your feed is too exciting, you might be doing it wrong.

🎧 Tune in now and ask yourself: What if boring is exactly what success looks like?#realestateinvesting

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

#entrepreneurtruth #slowandsteady #RealEstatePessimist #successmindset #financialfreedom #boringisbeautiful #kristikandel #erikstenbakken

What do faith, failure, purpose, BetterLife, $25K backflows, and a rogue Instagram comment have in common?

They’re all part of how Kristi Kandel and Erik Stenbakken — two wildly different real estate investors — somehow ended up co-hosting a podcast together.

In this special behind-the-scenes episode of The Real Estate Pessimist: The Good, the Bad, and the Truth About RE Investing, we’re not talking asset classes. We’re talking soul. Calling. Alignment. And how you actually find people who get you...even if you've never met in person.

We unpack:

• The real story of how Erik and Kristi met (spoiler: it started with sass).
  

• Why having 50 doors isn’t enough if your why is broken.
  

• The secret power of a strong buy box... for people.
  

• Why every investor needs community — and how to build one from scratch.
  

• Faith, integrity, generosity, and why giving now matters more than waiting for “someday.”
  

This one’s not about the next hot market. It’s about you — your values, your purpose, your ripple effect.

👉 So if you're chasing wealth but feel like something’s missing… this episode is your mirror.

🎧 Listen to the full pod now

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

#PodcastClip #PodcastEpisode #NewEpisodeDrop #PodcastReel #RealEstateTalk  #REICommunity #LifeOfAnInvestor #RealEstateJourney #FaithAndBusiness #CoHostStory

Jamie Hill—The Voice Behind the Brands, the Investor Behind the Fear, and One of My Closest Friends

Featuring: me (Kristi Kandel), Erik Stenbakken, and the one and only Jamie Hill (@voicesbyjamiehill)

This episode? Whew. We laughed, we nodded so hard our necks hurt, and honestly—I probably need to go back and re-listen with a notepad in hand.Because when Jamie talks? You shut up and soak it in.

Whether it’s behind the mic for a major brand or behind the scenes of her real estate journey, she keeps it raw, honest, and wildly insightful. She’s not some overnight success story. She’s one of us. She overthought, hesitated, ran the numbers ten times, and still bought the damn house.

Inside the episode, Jamie gets real about:

*What it’s actually like to be a voice actor in today’s world (hint: way more than just having a “good voice”)

*Why she left rent control behind and bought her first place—even when the mortgage was double her rent 😬

*How she went from “this terrifies me” to owning multiple properties*The disaster with a big box store that messed up her floors three times (and how she made it right)

*The power of the “3-foot toss” and why small, doable steps > big, blind leaps

*Why she didn’t go big—and still came out ahead

If you’ve ever been stuck in analysis paralysis, scared to move forward, or wondering if you’re “doing it wrong”… this one is for you.

Jamie’s story isn’t all sunshine and spreadsheets—it’s real, layered, and full of those “ohhh yep, been there” moments. It’s also a reminder that you don’t have to be fearless to get started—you just need to be willing.

Also… our friendship? Yeah, it’s been a lifeline. From our nearly identical first properties to dealing with the same kind of contractor chaos, it’s wild how parallel our journeys have been. This episode is proof that having someone in the trenches with you changes everything.

🎧 LISTEN NOW to hear the good, the bad, and the truth about real estate investing (and why sometimes… it’s just about the next 3 feet).

👇 Don’t forget:

✅ Subscribe & Like

✅ Comment if a contractor has ever personally disrespected your sanity

✅ Share with your “I want to buy but I’m scared” friend—they need this

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 #TheGoodTheBadTheTruth #RealTalkRealEstate#VoiceOverAndRealEstate #WomenWhoInvest #FriendsWhoInvestTogether#StartWhereYouAre #ThreeFootToss #SlowGrowthIsStillGrowth#FirstPropertyFears #RealEstateForRealPeople #ContractorNightmares

We’ve all seen the HGTV dream—buy a house, slap on some paint, and flip it for a fortune. But what if we told you that’s… not real life?

On this episode of The Real Estate Pessimist Podcast, we’re sitting down with Rachel Chwaszczewski (@intentionalpropertyadvisors), a 30+ year real estate veteran who’s been through it all—market crashes, foreclosure crises, fix-and-flips gone sideways, and the hard reality of building a real estate business from the ground up.

Rachel started her career in title work, getting a firsthand look at the mechanics of real estate deals. From there, she moved into fix-and-flips, new construction, and ultimately building her own successful companies.

She’s breaking down:

✅ The truth about investing through market crashes (including ‘08)

✅ The biggest mistakes new investors make (and how to avoid them)

✅ Why boring, sustainable investments are often the smartest moves

✅ The real cost of real estate success (hint: it’s not just money)

Rachel has built multiple businesses that actually last—not just flashy success stories that disappear in the next downturn.

If you think real estate is all about fast flips and easy wins, this episode will open your eyes.

📲 Connect with Rachel & Her Companies:

🌐 Intentional Property Advisors – Helping investors create smart, strategic real estate portfolios.

🌐 Practical Luxury Builders – High-end new construction, fix-and-flip, and workforce housing development.

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

Did you know Yoda had some of the best real estate investing advice ever?

"Do or do not. There is no try."

That’s the essence of a Buy Box—a simple yes or no filter that separates winning investors from those stuck in analysis paralysis.

On this episode of The Real Estate Pessimist Podcast, Kristi Kandel and Erik Stenbakken break down:

✅ Why a Buy Box is the #1 tool for making smart, fast real estate decisions

✅ How most investors start backwards—and lose time & money

✅ The real difference between a great deal and a time-sucking nightmare

✅ The buy boxes we use and how they make investing easier and more profitableReal estate success isn’t about looking at more deals—it’s about looking at the right deals.

If you’re not filtering ruthlessly, you’re not investing—you’re gambling.

Don’t forget to subscribe, like, and share with an investor friend who needs this strategy!

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

#RealEstateInvesting #BuyBox #Underwriting #SmartInvesting #InvestmentStrategy #FinancialFreedom #ShortTermRentals #RealEstateMindset #PassiveIncome #WealthBuilding #TheRealEstatePessimist

In this gripping episode of The Real Estate Pessimist Podcast, Kristi Kandel and Erik Stenbakken sit down with Craig Parsons. A man who started in construction at just nine years old but didn't jump into real estate investing until five years ago. 

And when he did? Buckle up.

Craig's story is one of resilience, creativity, and sheer grit. From a flooded building to shattered storefront windows to a tenant-induced waterfall, he's seen it all. And through every unexpected twist, Craig found a way to adapt, learn, and come out stronger.

Here’s what you'll discover:

🏔️ The Hiking Revelation: How a 210-mile trek with a stranger sparked Craig's real estate journey and his dream of hiking the Pacific Crest Trail.

🔥 The $5K Property Purchase: How Craig scored a property with just $5,000 down through savvy negotiation.

💥 Disaster After Disaster: Flooded floors, frozen pipes, and ceilings caving in. How Craig handled each crisis without throwing in the towel.

💡 Creative Financing Wins: How Craig leveraged private loans and seller financing to build his portfolio when traditional lenders said no.

🎯 Mindset Mastery: Craig's unshakable belief that "if it were easy, everyone would be doing it" and how that attitude helped him weather the storm.

From childhood job-site adventures to becoming a full-fledged investor, Craig’s story is a testament to perseverance and thinking outside the box.

🎧 Tune in to hear how Craig turned setbacks into stepping stones and how you can apply his lessons to your own investing journey.

Subscribe & Share! Your support helps us continue to share the good, the bad, and the truth about real estate investing.

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 #RealEstateInvesting #PropertyInvesting #AirbnbHosts #ResilienceInRealEstate

Before you jump into the world of vacation rentals, you need to listen to parts one and two of The Real Estate Pessimist Podcast.

In this can’t-miss episode, Kristi Kandel and Erik Stenbakken break down how the short-term rental game has changed—big time.

From sky-high guest expectations to professional scammers, the days of easy money with Airbnbs are over. But that doesn't mean you can't succeed. It just means you need to know the truth before you buy.

👉 Here's what you'll learn:

🔥 The Guest Behavior Shift: Why guests now expect resort-level experiences and leave 1-star reviews over traffic you can't control.

💥 The Professional Scammer Playbook: How some guests manipulate platforms like Airbnb and the steps you can take to protect yourself.

📉 Revenue Reality Check: Demand is up, but inventory has skyrocketed. Learn why your projected profits might not match today's market.

🌊 Drowning in Details: Why STRs aren't passive income—unless you’re okay with no profit.

💡 Consumer Trends Shifting: How booking windows have changed and what it means for your cash flow.

If you've been sold the dream of easy STR income, buckle up. Kristi and Erik share the real, raw, and sometimes ridiculous side of hosting—like the time a guest complained about crumbs under the trash bag. 😳

🎧 Listen now to get the unfiltered truth about the current STR landscape and how to navigate it like a pro.

Subscribe & Share! Your support helps us keep delivering the good, the bad, and the truth about real estate investing.

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 #STRInvesting #VacationRentalTips #AirbnbHosts #RealEstateTruth