The Real Estate Pessimist

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.

The Real Estate Pessimist is a education podcast hosted by RE Pessimist, with 50 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

RE Pessimist hosts The Real Estate Pessimist, a education show with 50 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

• 

  Episode #50

  The Episode We Never Thought We’d Record… The Final Chapter of The Real Estate Pessimist | EP50

  Dec 17, 202549 minS1

  <p>What happens when the podcast built on telling the truth… tells you its own truth?</p><p><br></p><p>In this milestone Episode 50, we sat down in person for the very first time and peeled back the curtain on everything. The wins, the wounds, the lessons, and the twist no one saw coming. This isn’t just a recap. This is the capstone. The closing chapter of The Real Estate Pessimist Podcast. And wow… it hit us harder than we expected.</p><p><br></p><p>We talk about why we launched this thing in the first place, why it...

  ListenShow Notes
• 

  Episode #49

  When Your Best STR Burns To The Ground… What Happens Next? | EP#49

  Dec 10, 202545 minS1

  <p>What do you do when your dream luxury short term rental literally burns to the ground with guests on the calendar and a five year plan tied to it?</p><p><br></p><p>In this episode of The Real Estate Pessimist, Kristi and Erik sit down with their friend and accountability pod mate, Anthony Guerra, to unpack what really happened the morning he got that text of his beautiful mountain cabin fully engulfed in flames. This is not a highlight reel story. It is Section 8 headaches, slumlord regrets, a pandemic pivot, a luxury STR win, and then a...

  ListenShow Notes
• 

  Episode #48

  Title: The $550K Rehab Nightmare That Tried to Break Her (But Didn’t) | Megan Ahern | EP#48

  Dec 3, 202554 minS1

  <p>Ever had a deal that tested every ounce of grit you’ve got? The kind that makes you question if you even want to do this anymore? That’s this story.</p><p>🔥 Episode Summary:<br>Meet Megan Ahern. A Nebraska flipper who thought she’d done it all… until she bought a sevenplex sight unseen. What started as “a great deal” turned into a six-month eviction saga, stolen AC units, collapsing walls, and a $550K rehab that nearly took her down. But instead of walking away, Megan fought through it. In this episode, she shares the raw truth about how she s...

  ListenShow Notes
• 

  Episode #47

  Reinvention Isn’t Free: How to Pivot Without Going Broke | EP#47

  Nov 26, 202527 minS1

  <p>Thinking about changing the game? Cool. Just know reinvention charges admission.</p><p>You’ve heard the ads: “no risk, guaranteed.” That’s cute. Real life has costs. In this episode, Kristi and Erik get painfully honest about the price of reinvention with money, time, ego, identity, and how to decide if the pivot you’re itching to make is strategy or self-sabotage. </p><p>We walk through the gut checks, the math, and the mindset so you can move forward in uncertainty without lighting your portfolio on fire.</p><p>What we cover:</p><p>Counting the cost: cash runwa...

  ListenShow Notes
• 

  Episode #46

  From Rock Bottom to Runway: The Episode You Didn’t See Coming (w/ Alan Underwood) | EP#46

  Nov 19, 202551 minS1

  <p>What if real estate isn’t the destination at all. Maybe it’s just the vehicle that gets you to who you’re meant to be?</p><p>Alan Underwood walked through loss, identity collapse, and the brink… then rebuilt purpose one tiny action at a time. Today he’s developing ADU-based multifamily in San Diego, flying medical missions with Angel Flight West, and reminding all of us why the doors and dollars only matter if they serve a bigger why. This is the “un-podcast” episode about life, perspective, and the truth behind the highlight reel, and we promise you haven’t he...

  ListenShow Notes

Recent guests on The Real Estate Pessimist. Study who booked and why before you pitch.

Based on semantic analysis of episode topics and host coverage, this show is a strong guest fit for executives in:

Industry fit is computed by PitchCentric using vector embeddings of the show's episode catalog.