Sitting across the table from me was a weary entrepreneur. That isn’t to say that the typical entrepreneur is always bright and cheery…I think most of us look tired yet hopeful—excited but exhausted.
But this entrepreneur had something else in his eyes…was it regret? Resignation? I couldn’t pinpoint it as he started to tell me his story.
He began by briefing me on his illustrious career—working for a large hospital chain in India—and retiring with flying colours. He spoke about this part of his career with such pride and joy. And retirement had not extinguished the fire in him.
He found this wide gap in oral screening in India—especially for oral cancer. What baffled him was that funds had been allocated among various national programs but the budgets always lapsed. And he had concocted the perfect tool that would be key in oral disease screening—it was portable, could be battery operated, but didn’t replace the dentist—it empowered them.
So he built a team, invested his savings and put in 5+ years of his retired life into bringing this device to market. What he accomplished was impressive—he didn’t have a technical background and he wasn’t an engineer. Yet he developed a medical device, got it clinically validated, got it approved by the appropriate regulatory authorities and brought it to market.
He had done everything by the book…anyone listening till this point would say he had done everything right. And yet, the business failed to gain momentum.
I reflected on this after our meeting. He had an addressable market. The venture was properly funded. He was solving a problem. He had a working device. Doctors had positive feedback. And yet—he couldn’t get the business off the ground.
Was there a problem more fundamental…more primitive than what met the eye?
Now it’d be tremendously easy to play “hindsight 20/20” and point out mistakes made along the way. And I don’t want to get into the mechanics of whether he had a concrete business plan, correctly identified the customer, or achieved product—market fit. The questions that stayed with me were more personal. Is there something beyond the quality of the idea or the strength of the business plan? Is there a “special sauce”? Could this business have been more successful in another entrepreneur’s hands?
Does entrepreneurship have an expiration date?
The more I thought about these questions, the more I thought about a few personal dimensions of entrepreneurship that could give me some answers:
Capacity for reinvention
Personal runway
The founder’s relationship with the venture
These may sound straight from a business school textbook…but bear with me:
The Capacity for Reinvention
We’ve all been told time and again that being an entrepreneur means that you’ve got to wear multiple caps—especially in the first few years of the business. You’ve got to be a salesman, a fundraiser, an accountant, maybe handle logistics, hell even take care of housekeeping.
But wearing multiple hats isn’t simply about performing different tasks. It requires the ability to repeatedly become a beginner.
If you’ve had a long and illustrious career before starting your first business - are you mentally equipped to take on novice roles? Is there friction in wearing other caps?
Experience undoubtedly gives an entrepreneur advantages. It can provide judgement, credibility, relationships, and a deeper understanding of an industry. But experience can also harden into identity. If you’ve spent your entire career seeing yourself in one way, it can be difficult to become whatever the business needs next.
But entrepreneurship demands repeated reinvention.
The question is not whether you would “do anything” for your business. The real question is: what does “anything” mean when the business asks you to become someone you’ve never been before?
Personal Runway
We generally speak about runway in financial terms: how many months can the company survive before it runs out of money? But founders have a personal runway too. That runway includes money, health, energy, relationships, and emotional resilience.
Every entrepreneur carries a personal life into the business. That doesn’t mean they’re less committed…it makes them human. And our professional and personal ambitions don’t always move according to the same timeline. A founder may be prepared to take an enormous risk in one stage of their life and find that same risk irresponsible at another.
Timing matters.
When a founder’s circumstances align with the needs of the business there can be tremendous amounts of growth. But when they don’t, it can be frustrating. Businesses never respect the founder’s preferred timing.
And it doesn’t matter how committed you feel towards your business…you’re trying to give it your everything. But when the weight on your shoulders constantly pulls you down, you may not be able to get back to the surface.
The Founder’s Relationship with the Venture
This dimension of an entrepreneur is probably the most difficult to assess. Every venture demands conviction. An entrepreneur must believe in something long before the evidence surfaces and continue to believe even in the face of rejection.
But conviction and attachment are not the same thing.
Conviction says, “This problem is worth solving.”
Attachment says, “The problem has to be solved, but my way and on my terms.”
The longer an entrepreneur works on a business, the harder it becomes to separate the venture from their identity. After 5 years of effort, the oral screening device was no longer a product…it became a part of the founder’s image—maybe even the final chapter through which he hoped to define his legacy.
A healthy relationship with the business requires the founder to separate the problem from the solution—and the solution from themselves. Sometimes as a founder the most important thing you can do is to not hold on. Maybe you’ve got to bring in a partner, or give another person authority, or step aside to allow the business to become something different from what was originally imagined.
And yes, I am aware how difficult that can be.
So, does entrepreneurship have an expiration date?
If we’re speaking about age…then no. (Sorry to disappoint, but the answer isn’t so black/white)
Older founders don’t have a monopoly on being stubborn, just as younger entrepreneurs don’t have a monopoly on energy or adaptability.
What may expire, is the fit between a particular founder and a particular stage of a business.
The “special sauce” of entrepreneurship could be less about having a fixed collection of traits and more about remaining capable of honest adaptation. Can you reinvent yourself when the business changes? Do you have the personal runway for what the venture requires? Do you love the business deeply without making it inseparable from your identity?
If you’ve answered no to some or all of the questions…then let me save you some time…if it smells foul it’s probably expired.
The title for this article came from a post I read from Dan Koe…it really resonated with me. Rarely do you see that kind of conviction from seasoned professionals stepping into business for the first time in their “later years”. And I don’t think it’s a coincidence that you see delusionally optimistic entrepreneurs who are young and inexperienced.