



Hello,
Welcome—I'm glad you're here.
If you’re anything like me, you didn’t become an entrepreneur because it was the easy route. You chose this because something in you couldn’t not build, question, create, or explore.
A few years ago, I hit a wall. From the outside, things looked great—venture deals, startup wins, packed calendars. But inside? I felt disconnected.
I had all the “success markers” and none of the clarity. I was building fast but couldn’t tell if it was in the right direction. And worse—I wasn’t sure why I was doing any of it anymore.
So I did something unexpected: I got back on a motorcycle.
That ride cracked something open. It reminded me of who I was before the noise, before the pressure, before I started measuring myself against someone else’s version of success.
That’s why I created the Key Drivers Assessment.
It’s a tool to help you strip things back and get honest with yourself. To uncover the motivation beneath the business. To realign with the reason you started in the first place—or the reason you know you need to start now.
This isn’t just an exercise. It’s a recalibration.
And if you let it, it can change how you lead, how you build, and how you define success from here on out.
The Key Drivers Assessment is a self-guided exercise that helps you:
1. Identify your primary entrepreneurial driver (Wealth? Legacy? Freedom? Creativity?)
2. Understand the strengths and blind spots that come with it
3. Make better decisions that align with your values, not just your to-do list
It’s designed to help you reconnect to what matters most—so your next move isn’t just efficient, it’s true.
How does it work?
It’s short. It’s honest. And it’ll make you think.
You can complete it on your own or with your team—but don’t overthink it. This isn’t about scoring points. It’s about clarity, not perfection.
And when you're done? You’ll have a decision filter you can come back to anytime you need to course-correct.

Ross O'Brien
Founder, Investor, and fellow road-tested entrepreneur
Think of the Key Drivers Assessment as a compass to help guide you. By identifying your core entrepreneurial driver, you’ll finally have language for what motivates you, clarity on what drains you, and direction for where you go next.
Uncover your core entrepreneurial driver so you can stop guessing and start building with purpose.
Use your results as a decision filter—so you can say yes to what matters and no to what doesn’t.
Get clarity and momentum without scrapping everything. One insight can change your whole trajectory.

Because when your purpose finally clicks, everything else starts to fall into place.
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