Real founder insights about surviving the AI commoditization era
Published October 24, 2025 • Based on Founder Reality Episode 34
Also available on: Apple Podcasts • Spotify • YouTube
I just finished Morgan Housel's "The Art of Spending Money" and it hit me like a brick.
Five years ago, when I was broke and running SimpleDirect out of my Toronto apartment, I read his first book "The Psychology of Money." It changed everything about how I think about earning money.
Now, three years later, with two profitable companies and actual money in the bank for the first time, I realized I had zero framework for spending decisions. I was just winging it.
That's dangerous when you're 27, your businesses are growing, and you suddenly have options you've never had before.
The Problem With Having Options
Here's my situation: SimpleDirect is profitable and growing. ANC is scaling as our AI venture studio. For the first time in my entrepreneurial journey, money isn't the constraint.
But that creates a different problem.
My friends are moving everywhere. Panama. Europe. San Francisco. New York. They're all saying the same thing: "George, you can afford to live anywhere now. Why are you still in Toronto?"
The question haunted me: Should I spend more on lifestyle? Reinvest everything into the business? Save aggressively for some future goal I haven't defined?
I didn't have a system for making these decisions. And asking ChatGPT felt like cheating.
Lesson 1: True Wealth Is Autonomy, Not Assets
Housel's first big point: the highest return on money isn't luxury goods or status symbols. It's control over your time and independence.
The ability to choose what you do and when you do it—that's real wealth.
He draws a distinction between being rich and being wealthy. Rich people have lots of assets. Wealthy people have freedom.
This hit me hard because three years ago, we were struggling to pay credit card bills. Money was so tight I was stress-eating ramen and avoiding certain subway stations because they reminded me of how broke I was.
Now suddenly I have options. Two paths, actually:
Path 1: Upgrade Everything Move to Manhattan or San Francisco. Join the tech scene. Pay $4,000+ for a one-bedroom because that's where "real founders" live.
Path 2: Optimize for Freedom Move to Thailand, Portugal, or Sri Lanka. Lower cost of living, better lifestyle, probably better mood. Wildlife, beaches, the whole digital nomad dream.
I chose a third option: Stay in Toronto and build optionality.
Not because I love it here (though it's fine), but because staying gives me the freedom to choose later. This is my base. In the future, I might have multiple bases.
The ability to move when Canada gets too cold, or when a project requires me somewhere else, or just because I want to—many people can't do that. They're locked into mortgages, jobs, expectations.
I was just in London a few weeks ago. Loved it. But I'm not rushing to move there permanently because I want to preserve the option to go anywhere.
Lesson 2: The "Enough" Problem Most Founders Never Solve
Every morning on the Toronto subway, I see the same thing: sleep-deprived people who clearly don't want to be going where they're going. Even at 6 AM, you can see the stress.
That's what happens when you don't control your time.
But here's the trap: even as entrepreneurs, we can fall into the same pattern. We just replace "working for a boss" with "working for the next funding round" or "working for the next revenue milestone."
Housel's second lesson: you need to define "enough."
Without a ceiling, you end up on an endless treadmill. $1 million becomes $10 million becomes $100 million becomes $1 billion. It never stops, and it makes your life miserable.
I've been trying to define my "enough" number for months. What does financial independence actually mean to me in concrete terms?
For SimpleDirect revenue. For ANC growth. For personal net worth.
Once I hit that number, everything else becomes choice instead of necessity. That's freedom.
I'm not sharing my specific numbers (email me if you're curious), but I'm forcing myself to write them down. Because without that definition, I'll just keep chasing the next milestone forever.
Lesson 3: The Status Purchase Trap
The third lesson hit closest to home: most of our big purchases are status signals, not utility.
Before any major purchase now, I ask myself: "Would I buy this if no one else knew about it?"
If the answer is no, it's a status purchase. And status purchases are freedom killers.
This applies to business decisions too:
- Are we buying this tool because it solves a problem, or because everyone else uses it and it makes us look sophisticated?
- Are we hiring because we're over capacity, or because 10 employees sounds better than 5?
- Are we raising funding because we need capital, or because announcing a round makes us look "legitimate"?
I've fallen into every one of these traps.
Three years ago, when we had 14 employees, I thought we looked like a "real company." The reality? It was chaos. One-on-ones, HR processes, performance reviews—none of it added value.
Now we're back to 5 people. We ship faster, communicate better, and everyone's happier. But for months, I resisted downsizing because I thought it would look like we were failing.
Status thinking almost killed our productivity.
What I'm Doing Differently Now
1. The Freedom Filter Every decision gets filtered through: "Does this increase or decrease my autonomy?"
Moving to San Francisco might open networking opportunities, but it would lock me into a $6,000/month apartment and a culture that measures success by funding announcements.
Staying in Toronto with the option to travel gives me more freedom, even if it's less impressive.
2. The Enough Exercise I'm finally writing down my numbers. What does "made it" actually look like for SimpleDirect? For ANC? For my personal net worth?
This isn't about limiting ambition. It's about knowing when I can shift from survival mode to optimization mode.
3. The Status Purchase Rule Before any major expense: "Would I buy this if no one knew about it?"
This saved me from upgrading our office space just to look more established. Our current setup works fine. The upgrade was pure ego.
The Spending Audit That Will Shock You
Here's your homework: use ChatGPT or Excel to categorize every dollar you spent in the last three months. Business and personal.
Ask yourself for each expense: Utility or status? Freedom or fiction?
I promise it will be shocking. Last year when I did this, I found $1,500/month in subscription services we weren't using. But the real value wasn't saving money—it was understanding my spending psychology.
How many expenses were driven by what I thought I "should" buy as a successful founder versus what I actually needed?
Why This Matters for Founders
As entrepreneurs, we control both sides of the equation: how much we earn AND how much we spend.
Most founders optimize for earning. Few optimize for spending.
That's the opportunity.
Wealth isn't about how much you make. It's about how much control you have. And spending is where you either build that control or destroy it.
The goal isn't to spend less. It's to spend consciously. To use money as a tool for freedom instead of a signal for status.
Because at the end of the day, the founder who can work from anywhere, say no to deals that feel wrong, and choose projects based on interest instead of necessity—that founder has already won.
Even if their bank account is smaller than the founder trapped in the status game.
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