The Real Estate Pessimist

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 whe...

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-l...

💥 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’...

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.

Thi...

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...

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 liv...

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 spo...

🔥 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 i...

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 pul...

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.

...

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… rep...

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 talki...

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 ...

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 es...

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

✅ Ho...

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 wate...

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 ...

What worked for STRs in 2020 won’t cut it in 2024. The game has changed, and if you’re not paying attention, fees, taxes, and regulations could wipe out your profits. 🏡💸

In this episode of The Real Estate Pessimist Podcast, Erik Stenbakken and Kristi Kandel expose the realities of STR investing today:

🔥 The New Landscape – How investors, municipalities, and HOAs reshaped the market.

⚠️ Regulation Crackdowns – Why cities are...

🎙️ Welcome to the Real Estate Pessimist Podcast—the good, the bad, and the truth about real estate investing!

In this episode, Kristi Kandel and Erik Stenbakken sit down with Vish Muni, a seasoned real estate investor, obstacle race enthusiast, and mindset powerhouse from Austin, Texas. Vish shares his journey from starting small with duplexes to navigating complex commercial deals like TripleNet leases and industrial outdoor stora...