The Best Time to Become an Entrepreneur Was Before AI. The Second Best Time Is Right Now.

A few weeks ago, a former colleague — twelve years at a regional bank, consistently high-performer, recently told his contract wouldn't be renewed — sent me a message that stayed with me.

"I keep waiting for the right time to do something of my own. I just don't know if I have what it takes."

I've been coaching senior professionals through transitions for years, and I hear versions of this constantly. The waiting. The self-doubt. The sense that entrepreneurship is for a particular type of person — younger, more reckless, maybe with a trust fund and a garage in Silicon Valley.

I want to offer a different frame. Because I think most people who believe they've missed the window are looking at this exactly backwards.

The Ground Has Shifted — And Not Only in the Ways People Fear

The same forces that are making traditional employment less secure are, simultaneously, making entrepreneurship more accessible than it has ever been in human history.

Let me be specific.

For most of the twentieth century, starting a business required three things that were genuinely hard to access for most people: capital, technical skills, and distribution.

You needed money to build a product, hire people, and sustain yourself through the uncertain early years. You needed engineering or specialist capability that took years to acquire. And you needed a way to reach customers — which meant expensive advertising, physical presence, or relationships built over decades.

All three of those barriers have been dramatically reduced. And AI is the primary reason why.

What AI Has Actually Done to the Cost of Starting a Business

Consider what was genuinely impossible five years ago but is now table stakes for a solo founder or small team.

You can build a functional product — software, content, a service platform — without engineering skills, using tools that weren't available to anyone at any price a decade ago. You can run your entire marketing operation with a fraction of the headcount that a comparable business would have required in 2015. You can have access to analysis, research, and strategic thinking that used to require expensive consultants or large internal teams.

Midjourney generated roughly US$500 million in revenue in 2025 with around 100 to 160 employees. Anthropic ran its entire growth marketing operation with a single person for nearly ten months. Klarna cut its workforce by roughly 40% while more than doubling revenue.

These are not outliers. They are signals of a structural change in what it takes to build and operate a business. And if that's true for companies at scale, it's even more true for someone starting something new — where the speed and cost advantages of AI compound most powerfully.

The capital requirement for validation — for testing whether an idea has legs before committing fully — has collapsed. The skills gap, while real, is narrower than it has ever been. And distribution, through digital platforms, communities, and content, is more accessible to an individual with genuine expertise than it has ever been.

The Economy Has a Jobs Problem That Only Entrepreneurs Can Solve

Here's the part of this conversation that most people aren't having plainly enough.

AI is making companies structurally leaner. Not as a temporary correction — as a new equilibrium. DBS announced plans to cut around 4,000 contract and temporary roles over three years as AI absorbs the work. These are not positions that will be refilled when the economy picks up. They are roles whose underlying function has been automated.

In previous disruptions, there was always a bounce-back. The internet economy stumbled, but it still needed people. Factories replaced farms, service industries replaced factories, and new categories of employment emerged to absorb the displaced.

The honest question — one economists are genuinely uncertain about — is whether AI creates enough new job categories to replace what it displaces. Nobody knows. But here is what we do know: the only mechanism in economics that reliably creates net new jobs is entrepreneurship. New businesses, serving new needs, hiring new people.

This is not an abstract principle. It is the structural reality your former colleagues are navigating. And it means that the people who build the capacity to create, rather than simply deliver, will be disproportionately positioned for what comes next.

The Experience You've Accumulated Is Not a Liability

Here is one of the most persistent myths about entrepreneurship that I encounter in coaching conversations with senior leaders: the belief that the window has closed. That the right time was earlier — when you were younger, more flexible, unburdened by a lifestyle and a reputation and people who depend on you.

I want to challenge this directly.

The academic research on entrepreneurial success by age is not what most people expect. A study of high-growth startups in the US found the average age of a successful founder at the time of founding was 45. Not 24. The founders with deep domain expertise, established networks, and hard-won judgment about what customers actually want significantly outperform their younger counterparts.

What looks like a liability — the weight of experience, the relationships built across decades, the pattern recognition that only comes from having been in the room when things went wrong — is actually your edge.

The new constraint is not experience. It is mindset. Specifically: the willingness to tolerate being a beginner again. To sit with uncertainty. To make something from scratch without the infrastructure of a large organisation behind you.

That is uncomfortable for most high-performing professionals. I know, because I went through it myself. But it is learnable. And it is worth learning.

The Frameworks We Learned Don't Fit the World We're In

One of the reasons smart, capable people hesitate at the threshold of entrepreneurship is that they try to apply the strategic frameworks they know — and those frameworks were built for a world that no longer fully exists.

Porter's Five Forces assumed relatively stable industry structures. Blue Ocean Strategy assumed you had time to find an uncontested market before competitors arrived. The Lean Startup assumed a pace of iteration that even the leanest startups can now dramatically accelerate with AI.

The new entrepreneurial logic is different. The barriers to entry have collapsed — which means competitive advantages are more temporary, but the speed of getting from idea to revenue has also compressed. What used to take eighteen months of validation can now happen in weeks. The cost of being wrong has fallen. The cost of waiting has risen.

This is not a reason to be reckless. It is a reason to reframe what it means to be ready.

What I Tell the Leaders I Coach

When a senior leader comes to me sitting with the question of whether to build something of their own, the conversation I've learned to have is not about whether the conditions are right. The conditions have never been more right.

The conversation is about what you are uniquely positioned to create — and for whom.

You have domain expertise that took decades to accumulate. You have relationships and credibility that cannot be manufactured. You have seen, from the inside, which problems don't have good solutions yet. You understand how decisions actually get made in the organisations you've spent your career inside. That is not nothing. That is, in fact, exactly what the market needs from someone who has lived it.

The question is not whether AI will take your job. The question is whether you'll use the same forces that are reshaping the employment landscape to build something that belongs to you.

My former colleague eventually stopped waiting. He spent six months validating an idea in the space he knew best, using AI tools to do the research, build the first version, and reach the first customers — at a cost he could absorb without quitting his day job. By the time he went full-time, he had paying clients and a model that was working.

The best time to start was years ago. The second best time is now. The third best time does not exist — because by then, someone else will have built what you were sitting on.

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If you're a senior leader sitting with the question of what's next — whether that's building something new, pivoting your career, or navigating what AI means for your role — I'd love to have that conversation. Book a complimentary strategy call here.

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Adeline Tiah is an ICF PCC Certified Executive Coach based in Asia, with 28 years of corporate leadership experience across global MNCs. She specialises in leadership transformation, high-performing teams, and culture change — and is the author of Reinvent 4.0, a guide to leading with purpose in an age of disruption.