Is your aspiration truly yours?
My startups were born from gigantic ambition. In both cases, I wanted to impact millions of people worldwide. It didn't take long for this to translate into a billion-dollar goal. The company would be worth billions and/or I would become a billionaire if I achieved my objectives.
A 10-figure target might seem enormous and overwhelming, but the simplicity of this goal makes some things easy. It becomes the success metric, and everything that leads to company growth, or more specifically its valuation, seems to point in the right direction.
While grand ambition can push an entrepreneur forward, it can be dangerous and lead to a demotivating place, potentially fatal to your startup's trajectory. Losing motivation because your initial aspiration seems impossible mid-journey won't just be bad for the company—it can make your life incredibly boring at minimum.
That's why, before it's too late, it's worth asking:
Is your aspiration really yours?
In retrospect, I see that the desire to make a difference in the world, measured by positive impact on millions of people, was genuinely mine. But the billion-dollar story came from entrepreneur references I share little with. In the entrepreneurship world, the most repeated stories are of such resounding success that they become anecdotal. They're the legends of dropouts like Steve Jobs, Mark Zuckerberg, and Bill Gates, who found success very early. For a long time, my inspiration was to be someone like them. That's what being impactful meant. Not anymore.
Today when I ask myself if I'd like to be Mark Zuckerberg, I immediately picture him in court apologizing to families who suffered irreparable losses (like children who reached the point of suicide due to mental health damage caused by social media).
So how did this goal of entrepreneuring toward the billion get injected into my mind?
It's not just that the stories are anecdotal. It's the entire industry built around such stories. Your company is only a startup if it's growing a lot; to keep growing exponentially, it'll need venture capital; and it'll only be interesting to a venture capitalist if it's a fund returner. In other words, success means having a billion-dollar exit.
You want to be successful, so you need venture capital and need to aim for the billion. Right?
Wrong!
The closure of my second startup, Pannacotta, happened at a peculiar moment. It was a whirlwind of emotions tied to entrepreneuring on the crest of the Artificial Intelligence wave, more reminiscent of getting continuously pounded in the middle of a tsunami. With each new OpenAI launch, it was said that thousands of startups would die prematurely. I don't know if that's the case, but that multi-billion-dollar game of giants made it clear that this aspiration serves only a few.
While this insane AI battle continues accessing billion-dollar aspirations that will push some founders to that destiny and thousands of others to fall far short, something else happened. For most founders, this was precisely when the capital game became more difficult. The downturn after the infinite capital party of 2021. The rule was now to be profitable and keep growing.
But wait, if the game changed and you can grow while being profitable, was the aspiration right?
I saw many founders talking about entrepreneuring differently. Even contemplating what some might call, in a slightly derogatory tone, lifestyle businesses. I saw founders choosing different paths that make much more sense for them than living an aspiration that isn't theirs. Rather than continuing to pursue a dream that doesn't belong to them.
The environment influences your aspirations
This is very common. Your friends, colleagues, and even enemies can invite, inspire, or challenge you to pursue certain things. From extremely negative things like addictions and compulsive behaviors to physical health goals like getting out of sedentary life and running a marathon, to choosing to go to law school because your father really wanted it. After all, who chooses to go to law school if not due to environmental influence?
Most of the time, a good aspiration is better than no aspiration, even if it's not yours. But for a long and hard journey like entrepreneurship, you need a deep connection with what you're pursuing. I recommend questioning this frequently and as early as possible, because you might reach a point where your freedom of choice becomes compromised.
Is the VC track toward billions the best path for you?
To explore a very practical example, let's dive deeper into this question. Pursuing accelerated growth through venture capital toward billion-dollar exits might be your authentic dream, making you jump out of bed every day. But if it's not, you might find yourself in a situation where you've committed to the point of making your own dream unviable.
How? If the idea was to build a billion-dollar empire, but along the way you diluted your stake in the business to the point where your percentage is single digits, there's a high chance of frustration.
Even if all conditions, like liquidation preferences and your exit value, work in your favor, a billion-dollar business still won't convert to a billionaire founder.
If you haven't chosen this path yet, the opportunity for a much earlier exit, but with a much more relevant stake in the company, might make your future lighter and richer.
Or, depending on your aspiration, an exit might not even make sense. Perhaps your greatest joy is running the day-to-day operations of the company with total freedom. If it's profitable and you don't have investors, this perspective can be financially delicious too.
Do your assessment
Enough examples and provocations. The idea isn't to convince you that you need to change paths or regret following a trail that wasn't what you'd prefer. The goal is to provoke your intentionality.
A simple framework to help your assessment can be summarized in 3 questions:
If I reach where my aspirations lead me, would I want to continue doing the same thing or drop everything and completely change my life?
Does the life I project for myself, pursuing this aspiration, align with the life I'd like to have in the coming years? Does the journey make sense for the next few years?
If I had the option to exit here without harming anyone (e.g., selling the company now or even shutting it down without disappointing anyone), would I want to continue pursuing my current path?
Every choice brings duties and responsibilities. Freedom isn't about not having to answer to anyone or having no commitments. Freedom is being able to choose to do what you're already doing because you have a choice.