E4: Work Shouldn't Feel Like Work (And Why I Just Said No to $5 Million)
Published August 15th, 2025 • 25 minutes
I just said no to $3-5 million.
Partnership came in last week. Legitimate opportunity. Two years of 'some grinding and minimum work' for life-changing money.
My spreadsheet said yes. My gut said absolutely not.
For the first time in my founder journey, I listened to my gut.
Here's why that was the smartest business decision I've ever made.
Everyone's Wrong About "Grit"
- Y Combinator: 'Do things that don't scale.'
- VCs: 'Grow at all costs.'
- LinkedIn influencers: 'Hustle through the resistance.'
Bullshit.
If something consistently feels like work - if you're dreading it, delaying it, making excuses - that's not resistance to push through.
That's your brain protecting you from the wrong path.
I've been building since 2019. Multiple companies. Supposedly know what I'm doing.
But every time I followed 'smart business advice' that felt wrong, it ended badly.
Every time I trusted my gut over my business plan, it worked out.
The $15K Google Ads Story
Our major lending partnership was on the line. They wanted traction. Volume. Results.
Solution was obvious: spend $15K on Google ads, drive conversions, keep them happy.
Every advisor said do it. Every framework said it made sense.
For weeks, I kept thinking 'I'll decide tomorrow.' Then 'I'll decide next week.'
When you're delaying a decision for weeks, you've already made it. You just don't want to admit it.
I never ran those ads. Lost the partnership. Best decision I ever made.
Because here's the thing: I've never spent money on ads in 6 years of building companies.
Not because I'm cheap. Because it goes against everything I believe about building.
I build products people want to talk about. I don't buy their attention.
The Payday Loan Test
Company calls me up. 'We'll pay you 30% of every loan amount.'
That's serious money in lending. Could have made bank.
My immediate reaction: 'Absolutely not.'
Didn't even think about it. Just knew.
Because high-interest loans felt wrong. Doesn't matter how much they pay.
At SimpleDirect, from Day 1, till now, we rank lenders by what's best for customers, not what pays us most. We've never compromised on this. Not once.
The moment you optimize for your revenue over customer outcomes, you're building the wrong business.
The Silicon Valley Myth
- 'You need to move to San Francisco.'
- That's where real founders are.'
- 'That's where the money is.'
Moving felt like playing someone else's game.
Toronto felt like home.
Staying in Toronto gives me:
- Lower costs, higher quality of life
- Access to Canadian grants and programs
- Different perspective from the echo chamber
- Ability to build authentically
Plus, geographic arbitrage isn't just financial. It's psychological.
Building where you want to be vs. where you think you should be changes everything.
The Sunday Night Test
Here's my business metric that beats revenue:
How do you feel Sunday night?
If you're dreading Monday morning, your spreadsheet might look good, but your business is broken.
Energy levels don't lie.
I can build AI tools for 12 hours straight and feel energized.
Put me in a partnership negotiation for 2 hours and I'm completely drained.
That's not laziness. That's data.
Your energy tells you where your natural strengths are. And in an AI world, your natural strengths are your only sustainable advantage.
Why AI Changes Everything
AI is about to eliminate every excuse for doing work that drains you.
All the boring, soul-crushing tasks? Automated.
The only work left will require human creativity, passion, intuition.
Which means if you're not naturally drawn to what you're building, you're screwed.
Everyone can use the same AI tools now. Everyone can build similar software.
The only differentiation left is you.
Your unique perspective. Your authentic voice. Your natural obsessions.
If you're grinding against your nature, you'll get out-hustled by someone for whom that same work feels like play.
Building vs. Business Development
I love building SimpleDirect features. Solving technical problems. Creating AI tools.
I hate traditional business development. Partnership calls. Networking events.
This taught me something crucial:
I'm a builder, not a dealmaker.
So I structure everything around building. I hire people who love the relationship side.
I focus on what energizes me. They focus on what energizes them.
We're not the same. And that's the point.
The Framework
Four questions I ask myself:
Does this energize or drain me?
Am I delaying this decision because I don't want to face it?
How do I feel about Monday morning?
Is this who I actually am, or who I think I should be?
If any of these feel off, that's your alarm system.
Listen to it.
What This Isn't
I'm not saying follow every whim.
I'm not saying avoid hard work.
I'm not saying ignore market feedback.
I'm saying: distinguish between temporary discomfort (normal) and persistent misalignment (warning signal).
When something feels like grinding against your nature for months, that's not grit. That's stupidity.
The Compounding Effect
When work doesn't feel like work, you can sustain it for years.
You wake up excited about problems instead of dreading solutions.
You make better decisions because you're energized, not depleted.
You create authentic differentiation because passion is impossible to fake.
This compounds. Someone grinding against their nature will burn out. Someone working with their nature will compound.
Guess who wins long-term?
The Controversial Truth
Sometimes the best business advice is to ignore business advice.
Your heart knows before your head does.
I've left millions on the table by following my gut instead of conventional wisdom.
And I'd do it again tomorrow.
Because building the wrong thing successfully is still building the wrong thing.
Why This Matters Now
We're entering a world where everyone has access to the same tools.
The same AI models. The same development frameworks. The same growth tactics.
Authenticity becomes the only lasting competitive advantage.
If you're not building from your natural strengths, someone else will out-execute you from theirs.
The Bottom Line
Work shouldn't feel like work.
If it does, you're either doing the wrong work, or doing the right work wrong.
Trust your instincts. They're smarter than your business plan.
Your gut reaction to opportunities tells you everything about alignment.
In an AI-first world, that alignment is everything.
Think I'm crazy for walking away from $5 million?
Email george@founderreality.com - I'll read your take in the weekend bonus show.
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