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Learn from this investor’s $100m mistake
In 2010, a Grammy-winning artist passed on investing $200K in an emerging real estate disruptor. That stake could be worth $100+ million today.
One year later, another real estate disruptor, Zillow, went public. This time, everyday investors had regrets, missing pre-IPO gains.
Now, a new real estate innovator, Pacaso – founded by a former Zillow exec – is disrupting a $1.3T market. And unlike the others, you can invest in Pacaso as a private company.
Pacaso’s co-ownership model has generated $1B+ in luxury home sales and service fees, earned $110M+ in gross profits to date, and received backing from the same VCs behind Uber, Venmo, and eBay. They even reserved the Nasdaq ticker PCSO.
Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.
Does this sound familiar?
I’ve built a shit ton of things. Just not for me.
For years, I helped other people grow their businesses.
Funnels. Email lists. Ads.
Clients got the assets. I got the invoices.
And I am fine with that because I needed to do what I needed to do.
But, I realized I stopped building systems for myself.
No brand. No list. No compounding trust.
Just wham bam, thank you… Corey.
This is a recurring theme with our generation.
What We Did for Others
Elizabeth, my podcast guest this week, gets it.
She helped turn a little etiquette brand into a $1.2M machine.
Built media campaigns with CNN. Landed clients like FedEx and Visa.
But she never built anything with her own name on it.
Me? I wrote ads and optimized funnels… while ignoring my own.
That’s the Gen X curse: we’re great at building things for others—
But we rarely paused long enough to build something for ourselves.
What We Never Gave Ourselves
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We haven’t been building personal brands.
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We haven’t been documenting our wins.
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We haven’t been building audiences we could bring with us.
Not because we were lazy.
Because we were too busy surviving.
But here’s the thing:
If you’ve ever built momentum for someone else,
You already know how to do this.
You just need to turn the camera (and the system) around.
What’s Changing Now
There’s no going back to the way things were.
AI isn’t just replacing tasks—it’s replacing people who don’t own anything.
That’s why Elizabeth’s story hit so hard.
And it’s why I’m building my first real system now—with my name on it.
The One-Way Door (Naval’s Paradox)
I saw this video from Naval Ravikant who said:
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“When you truly work for yourself, you won’t have hobbies, weekends, or vacations… but you won’t have work either.”
Naval Ravikant
It’s a paradox every solopreneur faces.
Once you taste the freedom of working on something that’s yours—
Of expressing who you are through what you build—
You can’t go back.
It’s not work-life balance. It’s work-life integration.
And it’s a one-way door.
That door’s open. And I’m walking through it for good this time.
That’d the Redefining Retirement in a nutshell.
The Late Bloomer’s Advantage
Here’s what we’ve got going for us:
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We’ve lived the stories that people care about.
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We’ve built stuff (we just forgot to document it).
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We’re not chasing clout because we’re chasing meaning.
The momentum we could’ve had?
It’s still there. Just waiting for us to turn the key.
AI Prompt Of the Week
Grab a free ChatGPT account (chat.openai.com) then copy and paste it into the chat box to discover your perfect topic – one that combines your experience with what people actually want to read about.