The Real Estate Pessimist

What happens when the podcast built on telling the truth… tells you its own truth? 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...

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? 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....

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. 🔥 Episode Summary: 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 reh...

Thinking about changing the game? Cool. Just know reinvention charges admission. 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. We walk through the gut checks, the ma...

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? 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 ma...

Ready to toss your plan and pivot? Sometimes that move saves your sanity… and sometimes it quietly wrecks your progress. We get real about the line between evolution and distraction in your investing journey. Kristi and Erik break down how to tell if you’re shifting for the right reasons (alignment, runway, ROI, season of life) or just trying to escape the boring middle where the real work happens...

What happens when the fire doesn’t just burn homes, but the market itself? On this episode of The Real Estate Pessimist Podcast , we sit down with Mike and Caroline Neubauer , Maui-based investors, parents, and podcast hosts who’ve lived through it all: the wildfires, the pandemic shutdowns, the short-term rental backlash, and came out still fighting. Mike, a former firefighter turned photographer...

Know When to Hold ’Em: Real Estate Cycles No One Talks About | EP#43 Ever feel like everyone else in real estate is dancing to a different beat? Welcome to the silent disco of investing—where everyone’s moving, but no one’s on the same song. In this episode, we pull back the curtain on something most investors never talk about: personal market cycles. When to hold. When to fold. When to press paus...

Dollhouse, Diva… Disaster? The Rehab Story You Won’t Believe | EP#42 What do you do when your “perfect” Victorian turns out to be sitting on… grass? No footer, rotting studs, tribunal fights, a neighbor who sues everyone, and a contractor who ghosted the scope. Yeah this one’s a ride. Michelle Correa went from 22 doors in under 12 months to the kind of structural nightmare that makes seasoned inve...

“Must Be Nice” Is a Myth: The Real Cost of Playing the Real Estate Game | EP#41 Ever looked at an investor’s highlight reel and thought, “Must be nice”? Cool. Let’s talk about the dues. Episode Summary: In this one, we go full Mythbusters on the lie that real estate investing is easy or that it ever will be. Kristi Kandel (developer/investor) and Erik Stenbakken (STR operator/agent) peel back the...

Everyone says what you don’t know won’t hurt you. But in real estate development? What you can’t see can destroy your deal before you ever pour a slab. In this episode, we sit down with Garland Harris an architect, developer, and straight shooter out of Houston. He pulls the curtain back on the “invisible” dimensions of real estate: deed restrictions, surveys, easements, utilities, and all the uns...

What happens when you stop waiting for perfect deals, and build the thing you wish existed? We’re pulling back the curtain on a project that has Kristi at a 75/10 on the excitement scale: an 8–10 acre, multi-sport + wellness + food + music destination in Southwest Florida. This is the real-time, messy-beautiful start: reverse-engineering sites with the county, phasing the rollout, courting partner...

What happens when your first big real estate wins get wiped out by a $70,000 loss? Do you quit or turn it into fuel? In this episode, we sit down with Jack Hartigan , who started hustling at 13, built a landscaping company into millions, and then jumped into real estate as a teenager. Jack’s story is raw and real: from early wins and shiny cars to a brutal tenant disaster that nearly erased everyt...

Are you making real estate decisions… or just reacting to headlines? In this episode, we get brutally honest about “news” vs. information. Erik (STR + long-term investor) and Kristi (developer who lives in zoning meetings) break down where investors get spun, how to separate fact from fear, and the simple habits that keep you from chasing hype—or hiding from opportunity. We’ve been burned, we’ve l...

What do you do when the career you worked your whole life for becomes the thing that’s breaking you? When the 70-hour weeks, sleepless nights, and the paycheck you thought was secure suddenly vanish—what do you do next? In this episode of The Real Estate Pessimist , I sat down with my cohost Erik and his wife Gelerie to uncover how they went from overworked physician + freelance photographer to bu...

If you’ve ever wondered how to go from a real estate investing idea to a crystal-clear buy box , this episode is your playbook. We’re showing you—in real time—how two experienced investors are building a new real estate venture from scratch and deciding exactly what to buy (and what to skip). In this episode of The Real Estate Pessimist , Kristi and Erik pull you behind the scenes as they explore...

What if your first big real estate win gave you false confidence for what came next? Mike and Lijia Deaton walked away from corporate careers to build a land flipping business, and it worked. But when they expanded into multifamily syndications, things got more complicated. In this episode, they open up about what it really takes to run a land business like a business… and the tough lessons they l...

If you’re not plugged into a real estate investor community , you’re missing the fastest way to grow your portfolio, find deals, and skip costly mistakes. The right real estate networking group can be a total shortcut connecting you to people, knowledge, and opportunities you’ll never get alone. In this episode of The Real Estate Pessimist , Kristi and Erik break down the single most underrated ha...

What do you do when a hurricane wipes out your dream just three months after you buy it? Most people quit. Mike and Dawn didn’t. In this episode of The Real Estate Pessimist, we share the raw, no-fluff story of two Midwest entrepreneurs who bought an iconic bar on Kristi’s home turf—Fort Myers Beach—only to watch it get annihilated by Hurricane Ian. But instead of walking away, they rolled up thei...

Ever wonder what seasoned investors wish they never did? And what they'd double down on in a heartbeat? We’re pulling back the curtain and spilling the dirt on the deals we regret, the lessons we paid dearly for, and the five best decisions that changed everything. This is the real stuff no one brags about on social media. The things we’d never do again, and the wins we’d fight for every time....

😬 Knowing when to walk away. That’s the real skill no one teaches. In this episode of The Real Estate Pessimist, we sit down with Stephanie—flipper, coach, and proud survivor of one of the most emotionally expensive deals we've heard. She opens up about the flip that started with a $5,000 non-refundable earnest money deposit… and ended in a gut-wrenching lesson on ignoring red flags and losin...

Ever feel like the government is just there to block your deals, stall your permits, and jack up your taxes? What if we told you the government could actually speed you up if you know how to play the game? In this episode of The Real Estate Pessimist , we get into the good, the bad, and the ugly truth about working with the government in real estate. Erik and Kristi unpack how the government is yo...

What do near-death climbs, 3 a.m. sewage emergencies, and a full-blown partnership rescue mission have in common? They’re all part of Corey Harrelson’s wild real estate story — and we unpack every gritty, gut-wrenching, and somehow still inspiring detail in this episode of The Real Estate Pessimist . Corey isn’t your typical investor. He doesn’t flex Rolexes or pitch you passive income fairytales....

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 importa...

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...