Founder’s Journey: The Problem with Solutions

Call me crazy, but after spending the last 17 years as a Venture Capitalist, I’ve finally returned to my roots and am sitting once again in the Founder’s seat. At the ripe old age of 54, I’ve traded my seat as an Investor for the rollercoaster ride in the Founder’s seat. Consider this post the first in a series of field notes from the trenches: Equal parts confession, revelation, and therapy session.

Today’s revelation? The asymmetry of certainty between problems and solutions.

Let’s start with a very basic framework that I used every day in my role as an Investor. It didn’t take hearing thousands of pitches to realize that at the core of each Startup is the pairing of a problem statement and a solution statement.

The problem statement is the Founder’s way of explaining a problem they’ve discovered and an articulation of why it’s a gigantic and profoundly painful problem.

The solution statement is the Founder’s way of articulating a better way of solving the problem they described in the problem statement paired with a narrative explaining why their users are likely to agree.

But I’m reminded of something both obvious and profound now that I’m back in the Founder’s seat:

Even though I can present my problem and solution statements with equal storytelling elegance, the certainty behind the problem and solution statements aren’t close to the same!

When you spot a problem worth solving, it’s like discovering a new continent. You can map it precisely, document its features exhaustively, and articulate exactly why it matters. The problem statement becomes your north star: clear, compelling, and unwavering.

But solutions? They’re mirages. What looks solid and complete from a distance reveals itself to be merely an outline when you get closer. That brilliant solution you’re ready to shout from the rooftops? It’s mostly wishful thinking wrapped in confident packaging.

I find myself in this exact position as we speak. My problem statement feels bulletproof. It’s backed by research, validated through countless conversations and supported by data. My solution seemed equally solid…until I started peeling the onion with my co-Founder and early ride-or-die team.

Every day reveals new questions and problems I haven’t considered. The elegant solution I’ve been pitching feels like a child’s drawing compared to the architectural blueprints it will need to become.

The temptation is to keep the illusion alive and to maintain the facade of certainty when speaking to potential team members and Investors. After all, who wants to follow a Leader into battle who admits they’re not entirely sure where they’re going?

But the truth is that we need to find talent that embraces this uncertainty. They’ll need to understand that the initial solution is merely a hypothesis. The real solution will emerge through iteration, experimentation, and the collective wisdom of a team looking at the problem through different lenses.

And even then, it’s only the starting line for the ultimate reality check: Users. They’ll take our precious solution and use it in ways we won’t have imagined and highlight flaws we’re blind to. That’s when the real work begins.

This journey from problem certainty to solution discovery isn’t a bug in the founding process; it’s what it’s all about. It’s where the magic happens, where true innovation emerges, and where I’m hoping to earn some new battle scars as a Founder.

So my advice? Fall in love with your problem statement, not your solution statement. Be humble about what you know and honest about what you don’t. And remember that the gap between your initial solution concept and what eventually works is where the real journey takes place.

Onwards and Upwards.

April 28, 2025