Start With Who You Are
Entrepreneur Office Hours - Issue #311
Aaron’s Note: I’m handing over the reigns for the issue intro this week to my Duke colleague and collaborator, Shep Moyle. To learn more about Shep’s background and connect with him, give him a follow over on LinkedIn.
When I start coaching a new founder, I don’t begin with their product.
I don’t ask about their market size, their roadmap, or their latest fundraising round.
I begin with three questions:
Who are you?
Why do you exist?
What do you really want?
You’d be amazed how many brilliant, driven entrepreneurs can’t answer them.
They can confidently tell me about their total addressable market. They can walk me through their next sprint. They can rattle off investor feedback and hiring plans. But when I ask what they truly want — as a human being, not as a founder — they pause.
And almost always, they say the same thing:
“That’s a really good question.”
And it is a really good question. Because, until you can answer those questions with clarity, you’re just renting someone else’s definition of success.
The Most Undervalued Competitive Advantage
Clarity isn’t a nice-to-have in entrepreneurship. It’s the foundation of everything:
Your focus
Your energy
Your decisions
Your culture
Your resilience
Clarity is what separates momentum from motion, and it’s what keeps you moving when the world gets messy (which, by the way, it always does).
I’ve lived this. I spent three decades building and leading a company through every imaginable high and low. And the truth I learned during that process is the greatest danger to a founder isn’t failure. It’s drift.
Drift Is What Happens When You Lose Yourself
When you drift, you forget why you started. You begin chasing the urgent instead of the important. You measure yourself by everyone else’s scoreboard. And somewhere along the way, you lose the thread of who you are.
That’s when founders burn out, teams lose faith, and great ideas die. They don’t die from competition. They die from confusion.
So let’s go back to the Three Questions and how they help solve the problem of drift:
1. Who are you?
I’m not asking for your title. I’m asking about your identity — what you stand for when everything’s on the line.
2. Why do you exist?
I’m not asking for a mission statement. I’m asking what purpose would still matter to you if nobody ever noticed.
3. What do you really want?
I’m not asking about your exit strategy. I’m asking what success looks like when the applause fades.
If you can answer these questions honestly, you unlock something founders rarely talk about: Alignment.
Your decisions start matching your values, your team feels your authenticity, and your company becomes a reflection of who you are, not just what you do.
That’s the moment leadership shifts:
From external → internal.
From hustle → purpose.
From noise → clarity.
Before You Build Anything Else… Build This
Before you build your next product, hire your next team member, or pitch your next investor, stop and answer these three questions:
Who am I?
Why do I exist?
What do I really want?
Until you do, every strategy and metric sits on sand. But once you’ve done it, everything aligns. The right people find you, the right opportunities appear, and the work starts to feel less like grinding and more like living your purpose.
That’s the real lesson, that’s where founders become leaders, and that’s the clarity every entrepreneur deserves before chasing the next great idea.
-Shep
This week’s new articles…
The Wrong Way to Build a New Startup
Inexperienced founders always make this same mistake, and it’s why so many new companies fail.
The Tragic Way AI Is Destroying 25 Years of Entrepreneurship Progress
In lots of ways AI has been great for startups, but there’s one huge problem founders are completely ignoring.
Office Hours Q&A
QUESTION:
Why do so many people seem to think they need a cofounder?
Every time I talk about wanting to start something, people immediately ask, “Who are you doing it with?” Like doing it solo isn’t even an option. I get startups are hard, but I’m not sure having a cofounder automatically makes things easier. But maybe I’m wrong?
- Jules
This is one of those questions I get asked a lot and I’ve answered it before. But I appreciate how you framed it — not as a demand for a cofounder, but as an honest wondering about whether going it alone is even possible.
Sure, it’s possible. But remember that startups are unbelievably difficult. Even the smallest ones. And not just emotionally difficult. I’m talking practical issues, too. There’s always more to do than one person can reasonably manage. You’re the CEO, the product manager, the marketer, the customer service rep, the salesperson, the janitor — all at once. That’s not just exhausting. It’s unsustainable. Heck… if you’re all by yourself, what happens if you want to go on vacation? Or what happens if you get sick!
Even if you could somehow handle the sheer volume of work, there’s still an even bigger problem, which is blind spots.
No matter how smart or experienced you are, you’ll always have gaps in perspective. You’ll miss things. You’ll overestimate things. You’ll solve the wrong problem. And, without someone else in the trenches with you, it’s very hard to catch those mistakes before they hurt you.
This ability to balance you is what a good cofounder brings. Having a cofounder isn’t just about more labor. It’s also more clarity, and sometimes even friction in the right places. In other words, it’s someone to tell you “no” when you’re too confident or “yes” when you’re losing steam.
To be fair, you don’t technically need any of that. But should you be open to finding one? Absolutely — especially if you’re already feeling the weight of going it alone.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer.