How Lyft and Uber Taught Me to Think Differently
“Growth is never by mere chance; it is the result of forces working together.” - James Cash Penney, founder of J.C. Penney
The Growth Paradox
Some of the fastest-growing companies in history have collapsed under their own weight. Why? Because growth alone isn’t enough. What matters is how you grow.
Too often we get trapped into thinking that scale is everything. If that were true, every company that expanded quickly would succeed. But we’ve seen this isn’t the case. Quick growth doesn’t always mean lasting growth.
Real success isn’t just about getting bigger. It’s about knowing when to make things better, when to adapt, and when to take risks.
The Old Playbook Is Breaking
The traditional management approach goes like this: Optimize everything. Scale at all costs. Manage to what’s easy to measure.
This playbook is becoming a trap for modern businesses. The next 2-3 years will be an extinction event for businesses stuck in old patterns who can’t adapt fast enough.
The companies that survive won’t just grow differently. They’ll think differently.
What I Learned in the Trenches
I spent six years at Lyft and Uber. We took risks and embraced uncertainty. We redefined how cities move and altered entire industries.
That kind of growth doesn’t come from following a formula or a playbook. It comes from frameworks that help you know when to focus on efficiency and when to take bold risks.
Here’s what I discovered: Success requires blending different ways of thinking.
Manager thinking focuses on consistency and improving what works
Entrepreneur thinking focuses on creating new paths for growth
Harmonizer thinking combines both to handle real-world complexity
What You’ll Learn
This “minibook” series is intended to show you how to blend these different approaches. Our world isn’t a perfect equation you can solve. It’s messy, changing, and human.
Drawing from my years at two of the most disruptive companies of our time, you’ll discover:
How to tell real data from ideal data and avoid chasing perfect information that doesn’t exist
Why flexible alignment beats rigid goals and how rigid goal-setting can kill innovation
How different types of workers need different management and why one-size-fits-all approaches fail
When to use structured thinking versus judgment and how to match your approach to your problem
Why growth needs more than just optimization and how to invest in ideas that don’t scale yet but become tomorrow’s advantages
How to develop “Harmonizers” in your organization—people who bridge different types of thinking and tackle messy problems that drive breakthroughs
Why This Matters Right Now
AI is taking over routine tasks. The future of work is changing. Your employees’ daily tasks will evolve. But humans remain essential for handling unpredictable and creative challenges.
Building for today and tomorrow means two things:
Address immediate challenges
Stay alert for future opportunities that don’t fit in spreadsheets
Whether you’re a CEO driving growth, a manager improving operations, or a founder ready to disrupt, this minibook offers practical insights. It’s for any organization that wants to thrive when change is the only constant.
A Personal Note
We learn by doing. In my six years in the rideshare world, we did a lot.
These lessons combine real experience with deep study and research. I’m an economist who spent 12,000+ hours operating in the startup world. These ideas come from the Lyft Guide to Making It Happen and Uber’s OG values.
Most importantly, this work comes from love for my teammates and what we built together.
Note: This is the introduction to Growth Isn’t One Sided—part 1 of 12 articles exploring how organizations grow without breaking. Each article focuses on one framework for balancing efficiency with innovation. [The complete minibook will be available here.]