The Hardest Question: Why Are You Building This?

If you’ve been on the founder rollercoaster as long as I have, you accumulate a stack of résumés—not just for the businesses that worked, but for the ones that taught you the most brutal lessons. Over the years, I’ve jumped into the fray for every reason imaginable:

• The Opportunity: I spotted a clear market gap and felt compelled to fill it.
• The Crew: A few smart friends wanted to build something cool together.
• The Corporate Call: A big partner needed a product co-founder to spin something up.
• The Impulse: Sometimes, just for the sheer, misguided excitement of starting something new.

Through all those ventures, the one constant—the engine that kept me going—was an almost desperate need to push forward and show progress, if nothing else but to myself. I leaned heavily on the feedback of those who had run the gauntlet before, the mentors who could open doors, and the early wins that validated the effort.

The Scar Tissue of the Journey

My approach to building has changed dramatically as I've built up layers of scar tissue. When you’re starting out, you feel invincible. The reality is, most of those early ventures hit the wall for a variety of reasons, most of which, in hindsight, were entirely avoidable:

• Stupid, Avoidable Mistakes: The top of the list is always the dumb things I should have known better than to do.
• The Wrong Founding Team: Realizing too late that chemistry, work ethic, and vision weren’t aligned.
• An Incomplete Understanding of the Market: Building a beautiful solution for a problem no one was actually willing to pay to solve.
• Chasing the Hype: Building for the sake of the pitch deck, not the product-market fit.

The mistakes weren't what defined the journey; it was the lessons they hammered home.

The Litmus Test: Asking the 'Why'

Now, as I work with early-stage founders who are in the messy phase of "figuring shit out," I start every conversation with the same foundational question: "Why are you building this?"

I dig past the polished mission statements and the projected revenue figures. I try to get them to the core of their motivation with a few strategic follow-ups:

• What's your vision? Can you articulate the world you want to create, not just the product you want to sell?
• Would you continue to solve this problem if you weren't getting the funding/accelerator support you are today?
• Would you do this if you had to toil away in obscurity? The vast majority of startups don't get the rocketship PR coverage you see on social media. Would you keep pushing if you had to operate outside the spotlight?
• Would you also do this without hordes of people cheering you by your side?

This is the ultimate stress test. Does the passion exist independent of the external validation, the cheerleading, or the media narrative?

The most difficult and essential realization a founder can have is that the path you choose—venture-backed, bootstrapped, lifestyle—is a fundamental lifestyle choice. It dictates your pace, your accountability, and your eventual exit.

The "right" reason is whatever aligns with your deeply held purpose. If you love the craft, you might be happier bootstrapping a profitable small business. If you are obsessed with creating massive, world-changing scale, then the VC route might be your path.

Find Your Tuning Fork

The journey only becomes sustainable when the founder’s internal 'Why' is stronger than the market’s inevitable 'No.'

But even the strongest 'Why' needs guidance. This is why you must find the people who are going to stick by you through this journey—they're your tuning fork. They are the co-founders, early employees, and non-investor mentors who know your core mission. If you start to drift toward chasing shiny objects, sacrificing long-term value for a quick PR hit, or getting lost in the weeds, they are the ones who can strike that original note and help you re-calibrate.

The worst mistake is chasing someone else's definition of success. Finding that true North Star motivation is the only way to endure the scar tissue and keep pushing that boulder forward.