The Real Estate Pessimist
Podcast Description
The Good, bad, and the truth about real estate investing
Podcast Insights
Content Themes
The podcast centers on the challenges and lessons of real estate investing, with themes including overcoming financial barriers, the importance of mindset, and navigating unexpected disasters. Example episodes include April Vogt's journey to purchasing a duplex despite financial limitations, the impact of mindset on real estate success, and cautionary tales involving property crises such as dealing with law enforcement raids and major financial losses.
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.
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 everything. But instead of walking away, he doubled down and turned an 11-acre farm into a cash-flowing, mixed-use property and carving a new path forward.
Here’s what we cover:
Jack’s first hustle at 13 that lit his entrepreneurial fire
How he scaled a landscaping business to $3M+ before 20
Buying duplexes as a teenager and learning the hard way about bad tenants
The $70,000 loss that could’ve ended it all
Turning a farm into a real estate goldmine
Why speed, risk, and resilience are Jack’s secret weapons
The bold truth: Every investor takes losses. The great ones learn to make them count.
Connect with Jack:
Instagram: jackhartigan20
LinkedIn: Jack Hartigan
🎧 Listen now: https://www.youtube.com/@TheRealEstatePessimist/videos 📍 Find us on all platforms: YouTube: https://www.youtube.com/@TheRealEstatePessimist/videos Spotify: https://open.spotify.com/show/30iW9NGVaPVqIBZqf8iNd5?si=aa41afe7b90b4315 Apple: https://podcasts.apple.com/us/podcast/the-real-estate-pessimist/id1785003692
🎧 Want more from Kristi? Hear how she’s helping locals become developers in their own communities by removing the gatekeeping.
→ Listen to the Local Real Estate Developer Podcast: https://www.youtube.com/@LocalRealEstateDeveloper/podcasts
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Disclaimer
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