The Quiet Questions I Ask Potential Founder-CEOs
I have been reflecting on the many conversations I’ve had with first-time founder-CEOs over the years — those one-on-one encounters where someone is venturing down this path for the first time and looking for honest perspective. Since I write this blog to reach and support more people than I could ever meet with personally, I want to capture the essence of those conversations here. What follows are the questions I ask, the counterpoints I raise, and the litmus test I apply — in hopes of supporting your own self-reflection before you leap.
When a first-time founder finds me — via an intro, a talk, or some other path — we get through the pleasantries and background, and then they start asking what’s really on their mind. To help, I try to uncover their goals and motivations. Why? Because those goals and motivations are what will, and should, shape the purpose, strategies, and organization of the business they want to build and their ability to sustain the effort to accomplish their goals.
Deciding to found a company is a significant leap. The process will demand far more than most first-timers appreciate going in: time, energy, personal savings, risk tolerance, stress, and sustained uncertainty. I want to understand how clearly they’ve reckoned with those costs — and that naturally leads into a discussion of what potential benefits and motivations could make the investment of all those resources genuinely worth it.
Here are the most common reasons I hear for wanting to found a company — along with the counterpoints I share, because they tend to be underappreciated.
“I don’t want to work for a boss.”
Counterpoint: As a founder-CEO, you have to figure out what to do about everything — building a product, selling, fundraising, managing your numbers, navigating regulations and taxes, marketing, hiring, firing, cybersecurity, contracts, and on and on. The list is genuinely endless, and the responsibility to learn enough to handle it — often yourself, especially early on — is a constant. A brilliant technical co-founder once told me that the most surprising thing about building a startup was that there was frequently no one to call for help on critical things he knew nothing about, but still had to get done. And being your own boss, it turns out, can be profoundly lonely.
“I want to solve a problem no one else has solved.”
Counterpoint: Before proceeding on this basis, do your due diligence seriously. Are you sure no one else has solved it? How do the people who have this problem handle it today — and are they sufficiently dissatisfied with their current solution to switch? Is the problem truly significant if no one has yet bothered to solve it commercially? And critically: will someone pay enough for your solution to make it worth building a business around?
“I want the freedom to do what I think is best.”
Counterpoint: You may not have a traditional boss, but you will have a demanding set of stakeholders you are accountable to — investors, team members, customers, suppliers, regulatory bodies. Balancing their often competing needs on very limited resources can feel far more like a straitjacket than freedom. The early romantic notion of autonomy tends to collide quickly with reality.
“I want to make an impact.”
Counterpoint: This is actually one of the more durable motivations, and worth taking seriously. Impact can be easier to see in a startup because everyone is closer to the customers whose lives are — hopefully — improved by what you’re building. That proximity can be a powerful reason to get out of bed every day and pour your heart into the work. That said, creating meaningful impact through a startup is still fiendishly hard, and there may be other paths to impact worth honestly considering before you commit.
“I’m confident my concept will succeed.”
Counterpoint: The vast majority of startups fail — after founders have spent every penny of their personal savings trying to make them work. Occasionally, the stars align, and a venture succeeds beyond anyone’s expectations, but statistically, that outcome is rare. The fact that you can easily recall startup success stories is largely a function of survivorship bias — the cognitive error that occurs when we focus on the ventures that made it through a selection process while overlooking the far greater number that didn’t, simply because failures are less visible and rarely covered in the press. For every wealth-generating success story, there are thousands of startup corpses we never hear about, leading us to overestimate both the odds of success and the reliability of any given strategy.
“I want to make money/build wealth.”
Counterpoint: Building a startup requires resources — usually over an extended period of time. If it were straightforward, anyone could do it and few would value the result. Building something genuinely valuable typically means draining your personal savings and navigating the always-difficult process of raising outside capital. Given the odds and the true opportunity costs involved, most founders will struggle to break even — let alone generate meaningful wealth. While some do build something valuable enough to create returns worth spreading across all equity holders, most will not. And, sometimes, a steady salary will give you more savings in the bank.
As one of my own early mentors did for me, I will often try — deliberately — to dissuade the potential founder as we explore their motivations. If I can talk someone out of it, that’s actually useful information: they likely don’t yet have sufficiently strong conviction in themselves or the opportunity they’ve identified. It’s a litmus test. If a few pointed questions in a short conversation can shake your resolve, you probably don’t yet have all the pieces in place to slog through everything that lies ahead. Better to discover that now.
But sometimes — not often, but sometimes — a founder has identified a profoundly important and genuinely painful problem, has developed an innovative and valuable way to address it, and brings the breadth of skills, creativity, and tenacity required to actually build a business around it. Those are the ones worth doing. And I won’t be able to talk that person out of it.
So before you jump into the deep end, make sure you know why you are jumping — and make sure that building a business is genuinely the best way to solve the problem you’ve identified. Spend some time honestly reflecting on where your strengths lie and what role you might be best suited for. Big, successful companies require a variety of complementary people and skill sets to get there, so you don’t need to be everything. But you do need to be honest with yourself about what you bring, what you don’t, and whether your motivations are durable enough to sustain you through the years it will likely take to build something worth building.
The questions aren’t meant to discourage you. They’re meant to prepare you — and to make sure that if you do leap, you’re leaping with your eyes open.
