The Real Estate Pessimist
By RE Pessimist
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Episodes: 50
Description
The Good, bad, and the truth about real estate investing!
Don’t let the name fool you. We’re not here to be negative. We’re here to be real pull back the curtain and show you what’s behind those highlight reels.
I’m Kristi Kandel: RE developer & investor. My cohost Erik Stenbakken, and I are bringing you the unfiltered stories behind the deals. The ones you don’t see on social media.
And the wisdom that only comes from actually living it.
Because real estate isn’t all private jets and passive income.
Sometimes it’s evictions and 3 a.m. plumbing disasters.
And we’re here for all of it.
| Episode | Date |
|---|---|
|
The Episode We Never Thought We’d Record… The Final Chapter of The Real Estate Pessimist | EP50
|
Dec 17, 2025 |
|
When Your Best STR Burns To The Ground… What Happens Next? | EP#49
|
Dec 10, 2025 |
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Title: The $550K Rehab Nightmare That Tried to Break Her (But Didn’t) | Megan Ahern | EP#48
|
Dec 03, 2025 |
|
Reinvention Isn’t Free: How to Pivot Without Going Broke | EP#47
|
Nov 26, 2025 |
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From Rock Bottom to Runway: The Episode You Didn’t See Coming (w/ Alan Underwood) | EP#46
|
Nov 19, 2025 |
|
Changing the Game: When a Direction Change Is Right vs. Wrong | EP#45
|
Nov 12, 2025 |
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🔥 When the Fire Hits Home: Maui Investors Who Survived Disaster | EP#44
|
Nov 05, 2025 |
|
Know When to Hold ’Em: Real Estate Cycles No One Talks About | EP#43
|
Oct 29, 2025 |
|
Dollhouse, Diva… Disaster? The Rehab Story You Won’t Believe | EP#42
|
Oct 22, 2025 |
|
“Must Be Nice” Is a Myth: The Real Cost of Playing the Real Estate Game | EP#41
|
Oct 15, 2025 |
|
The Invisible Traps That Can Kill Your Deal Before It Starts - Garland Harris | EP40
|
Oct 08, 2025 |
|
We’re Building the Place Our Community Actually Needs (Before the Dirt Is Even Bought) | EP39
|
Oct 01, 2025 |
|
From Teen Hustler to a $70K Loss: The Lesson Every Real Estate Investor Needs | EP38
|
Sep 24, 2025 |
|
Good News Bad News or Good Clickbait? Why Your Sources Are Making You Broke | EP37
|
Sep 17, 2025 |
|
From Burnout Doctor to Real Estate Freedom: How One Couple Rebuilt Life on Their Terms | EP#36
|
Sep 10, 2025 |
|
From Idea to Buy Box: Starting a Real Estate Venture Together | EP35
|
Sep 03, 2025 |
|
Land Flipping Worked. Multifamily Taught Them Even More - Mike & Ligia Deaton | EP34
|
Aug 27, 2025 |
|
Real Estate Investor Community: The Shortcut Most People Ignore | EP33
|
Aug 20, 2025 |
|
Hurricane Ian Leveled Their Dream. You Won’t Believe What They Did Next | EP#31
|
Aug 13, 2025 |
|
🎙️ 5 Big Mistakes & 5 Wins We’ll Never Regret | EP#31
|
Aug 06, 2025 |
|
I Should’ve Walked From the $5K... Featuring Guest Stephanie Lombardo | EP#30
|
Jul 30, 2025 |
|
The Government: Gatekeeper, Partner, or Pain in the Asset? | EP#29
|
Jul 23, 2025 |
|
From Climbing Half Dome to a Burning Poop Plant: How One Investor Survived It All | EP#28
|
Jul 16, 2025 |
|
At first, we thought it was a bad idea… | 🎙 EP# 27
|
Jul 09, 2025 |
|
The Contractor’s Confession: Real Estate Truths from Both Sides of the Hammer - Tyler Madden | EP26
|
Jul 02, 2025 |
|
Why Every Real Estate Partnership Needs a “Pre-Nup” | EP#25
|
Jun 25, 2025 |
|
The Truth About Live-In Flips, Marriage, and Building Through the Chaos | EP#24
|
Jun 18, 2025 |
|
Help! I’m in a Funnel and I Can’t Get Out! | EP#23
|
Jun 11, 2025 |
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Congrats, You Just Made the Worst Financial Decision of Your Life | EP#22
|
Jun 04, 2025 |
|
I’ll Just Do It Faster Myself — How That Mentality Is Sabotaging Your Freedom | EP#21
|
May 28, 2025 |
|
🔥 Someone Tried to BLOW UP His Investment?! Real Estate Pessimist Podcast ft. Mike Sgandurra | EP#20
|
May 21, 2025 |
|
Fast & Furious Real Estate? Why Social Media is Wrecking New Investors | EP#19
|
May 14, 2025 |
|
From 875 Houses to Hotels, Real Wealth, & What Actually Matters: Keith Blackborg Tells All | EP#18
|
May 07, 2025 |
|
🤔 The One Thing That Almost Every Successful Investor Ignores | EP#15
|
May 06, 2025 |
|
What do faith, purpose, BetterLife, $25K backflows, and a rogue Instagram comment have in common? | EP#17
|
Apr 30, 2025 |
|
Swiss Army Knife for Life – Voiceover, Real Estate, and the Power of the Three-Foot Toss | EP#16
|
Apr 23, 2025 |
|
30 Years, Market Cycles, and a Whole Lot of Lessons: Real Estate Wisdom Rachel Chwaszczewski | EP#14
|
Apr 09, 2025 |
|
The Unexpected Jedi Mind Trick That Makes Real Estate Investors Rich! | EP# 13
|
Apr 02, 2025 |
|
Improvise, Adapt, and Overcome: Craig Parsons—The Man Who Does What He Says and Figures It Out 🛠️🏡 | EP #12
|
Mar 26, 2025 |
|
PART 2: Wait! Don't Buy a Short-Term Rental... Yet! 🏖️🚫 | EP # 11
|
Mar 19, 2025 |
|
🚨 PART 1: The Short-Term Rental Market is Changing – Are You Prepared? 🚨 | Ep #10
|
Mar 12, 2025 |
|
How to Win in Real Estate When the Odds Are Stacked Against You 🏠 | Ep #9
|
Mar 05, 2025 |
|
7 Reasons You’re Not Ready to Scale (Yet!) – Avoid These Costly Mistakes! |EP #8
|
Feb 26, 2025 |
|
🎥 The Truth About Real Estate: Exposing Myths, Lies, and How to Play Your Own Game | EP #7
|
Feb 19, 2025 |
|
How We Stopped Playing It Safe and Built Real Estate Wealth with Grit, Risk, and a Little Crazy | EP #6
|
Feb 12, 2025 |
|
They Said She Couldn’t Buy a House… So She Bought a Duplex Instead! How April Beat the System | EP #5
|
Feb 05, 2025 |
|
🎙️ Mindset: The Key to Surviving and Thriving in Real Estate | #4
|
Jan 29, 2025 |
|
When Homeland Security Kicks in Your Door: Real Estate Horror Story Turned Win | # 3
|
Jan 22, 2025 |
|
How to Lose Half a Million Dollars on One Door | # 2
|
Jan 19, 2025 |
|
Beyond the Hype: What Real Estate Investing Really Takes | #1
|
Dec 12, 2024 |