E5: Why Simple Always Beats Sophisticated (And How I Wasted 2 Years Building Complex BS)

I spent 2 years and hundreds of thousands building a sophisticated quant trading firm. Hired 5 engineers. Built complex algorithms. Backtested everything. Result? Couldn't beat the S&P 500.

Then I discovered Bogleheads on Reddit. Bought 8-10 simple index funds and household names in May. It's August now. I'm up 5.5% in 3 months doing absolutely nothing.

The pattern is everywhere:

• SimpleDirect: Built a complex web platform for contractors. They just wanted to text and call.
• Team management: 14 people = chaos and performance reviews. 5 people = family vibe and faster execution.
• Investment: Years of sophisticated algorithms < 3 months of simple index funds.

Here's what I've learned: In an AI-first world where everyone can build complex features cheaply, simplicity becomes your competitive advantage. Complexity doesn't equal better results.

The four questions I ask myself now:

1. Can this be simpler?
2. What would happen if I removed this entirely?
3. Am I adding complexity to feel smart or to get results?
4. Would I explain this approach to my grandmother?

Real examples from building companies since 2019:

• Why our contractors prefer AI phone agents over fancy dashboards
• How cutting from 14 to 5 people made us execute faster
• The Bogleheads approach that's beating Wall Street sophistication
• Why simple SaaS tools always win over feature-bloated alternatives

The truth: Most of us think complicated = better because that's what we're taught. But the simplest approach usually wins. Your customers want solutions, not complexity.

The framework: Start with the outcome you want. Work backwards. Cut every unnecessary step. Ask yourself: "What's the easiest way to make this happen?"

In an AI world, everyone can build complex features. The winners will be the ones who resist the urge.

Disagree with my approach? Email [email protected] - I'll read your perspective on the weekend show.

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