The Real Estate Pessimist

💥 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...

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 t...

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,...

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 alum...

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, en...

🔥 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 r...

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 r...

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...

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...

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 talk...

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. W...

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 ha...

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, fa...

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 wi...

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&#3...

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. ⚠️ Regulati...

🎙️ 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...

7 Reasons You’re Not Ready to Scale (Yet!) – Avoid These Costly Mistakes! Scaling your real estate portfolio sounds exciting, but growth without the right foundation can lead to costly mistakes. In this episode of The Real Estate Pessimist Podcast, Kristi Kandel and Erik Stenbakken break down the 7 biggest red flags that could hold you back from successful scaling. Here’s what we cover: ✅ No syst...

Welcome to The Real Estate Pessimist Podcast —where we dive into the good, the bad, and the truth about real estate investing. 🎙️ In this episode, Kristi Kandel and Erik Stenbakken unpack the hype surrounding real estate, debunk common misconceptions, and share how they transformed hesitation into action, building wealth one deal at a time. What You’ll Learn: 🚩Why "highlight reels" on s...

Ever wondered how everyday people break into the world of real estate investing and unlock opportunities they didn’t even know existed? 🏠 In this episode of The Real Estate Pessimist Podcast , hosts Kristi Kandel and Eric Stenbakken share their personal journeys from being stuck in the "hamster wheel" 🐹 of active income to discovering the life-changing machine of real estate investing....

🔥 💰 They Said She Couldn’t Buy a House… So She Bought a Duplex Instead! How April Vogt Beat the System & Bought Real Estate on a Bartender’s Salary! You are NOT going to want to miss this episode of  @TheRealEstatePessimist  Podcast! We sat down with April Vogt, who started investing in real estate when she literally couldn’t afford real estate. That’s right, she couldn’t qualify for a singl...

🌟 Episode Summary: In this episode, Kristi Kandel and Erik Stenbakken dive into the critical role mindset plays in real estate investing and life. It’s more than the numbers and strategies. It’s how you navigate setbacks, take ownership, and find the courage to move forward when things get tough. 💪 Kristi and Erik share personal stories of challenges, like rebuilding after hurricanes, tackling f...

In this episode of The Real Estate Pessimist Podcast , Kristi Kandel and Erik Stenbakken dive into a story that’s as shocking as it is full of lessons for real estate investors.  🏡 Imagine closing on what seems like the perfect fourplex only to find out Homeland Security is busting into one of the units because it’s a stash house for the cartel. 😳 Kristi shares the jaw-dropping details of inheri...

In this episode, Erik Stenbakken dives deep into a real estate nightmare—a project gone so wrong it ended up costing nearly $500K. This isn’t just any horror story; it's a detailed breakdown of how things can spiral out of control in real estate development and what you can learn from it. 🔗 Link to full show: https://youtu.be/rhwsZYLUAxo What You’ll Learn in This Episode: 🤦‍♂️How Erik went f...

Welcome to the very first episode of The Real Estate Pessimist: The Good, Bad, and the Truth About Real Estate Investing. In this episode, Erik and Kristi Kandel introduce themselves and share the mission behind this podcast: to uncover the raw, unfiltered realities of real estate investing. We dive into our personal journeys, sharing the pivotal moments that shaped our paths, including some of ou...