The Multifamily Real Estate Experiment Podcast

MFREE 112 Trailer # 2 with Christine Healey: Can Personal Passions Shape Professional Wins?

Shelon Hutchinson Season 3 Episode 112

Aloha, It’s Shelon "Hutch" Hutchinson here! If you’re enjoying 'The Multifamily Real Estate Experiment' podcast, please like, comment, and share our episodes to help us reach and inspire more people. Thank you for your support!

In this episode, Christine Healey and Hutch head into the Focus Round and cover everything from startup equity to stand-up comedy — literally.

Christine opens up about nearly joining Airbnb in its early days, the missed opportunity that stuck with her, and how it shaped her views on ownership vs. income. She talks about why equity isn’t just for founders or tech insiders — and how veterans, career changers, and professionals can use it as a real wealth-building move when the timing is right.

She also dives into the difference between working with a big-name investment firm and a boutique firm that actually knows your name — and why real trust and clarity matter more than flashy branding.

And just when you think it’s all numbers and strategy, she flips the switch and reveals her love for stand-up comedy — proving that sharp analysis and unhinged humor can live in the same brain.

This one’s packed with mindset shifts, real talk, and unexpected laughs.

#EquityMindset #VeteranInvestors #OwnMoreOfAmerica

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Thank you to all of our listeners!!! We would love to hear from you!!!

Email me at:
hutch@hsquaredcapital.com

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Track 1:

We're gonna go through the focus round, Christine, What do you do for fun? Standup comedy. Oh, you're a comedian. I love to watch it. very rarely I'll do an open mic or some sort of performance, but I'm just a fan of comedy all around. What is the biggest investment opportunity, you almost passed on, but you didn't? I do remember I was almost an early adopter of Airbnb in a sense. Okay. I started using it when it was still a bit sketchy when you'd go stay in, some person's house and I wish that I had just gone to work for Airbnb and been part of the early building of that company. Christine, how do you explain complex ideas or complex deals simply, to busy investors? Communications, having a passion for my clients. I don't want them to be intimidated by this market. I want them to really understand, and so that's my commitment. If I explain it to you one way and it's not catching on, I'll explain it to you a different way and spend that time with you that you need to feel comfortable. What is one thing you wish you understood earlier about, pre-IPO investing? I think a lot of people, especially when faced with a new type of investing, they default to working with one of these big companies, big platforms. Okay. And I think that's a mistake because you can work with someone like me. Where you're gonna be a focus of mine. What do you attribute to your ability to thrive, in such a high stake space? I genuinely love what I do. I find it really fun. I really love serving my clients, and so genuinely enjoying what I'm doing.