Today, he books his own flights.
“There are no car pickups, no assistant managing your calendar,” says Mitra. As CEO of Humanizetech. ai, a generative AI-powered software-as-a-service company that he founded in 2024, the 57-year-old is now embracing the chaotic energy of the startup world.
He wouldn’t have it any other way. “Ab nahin to kab?” he asks. If not now, then when?
SECOND WIN
That question is being asked by a growing number of senior corporate executives in their 50s and early 60s who are choosing entrepreneurship over retirement, board positions and advisory careers. Unlike first-time founders in their 20s and 30s, these executives are not chasing entrepreneurship as a career option. They are embracing it as a second act.
Alpana Parida, 62, has known the whirlwind of corporate life. She headed marketing and merchandising at Tanishq, ran the brand consultancy DY Works, repositioned L&T and built brand architecture for IHCL. Now, she is happy to be known as the founder of Tvarra, which makes helmets specifically designed for women and children. She says it addresses a massively underserved opportunity in a country where nearly 30 crore women and 60 crore children ride pillion every day.
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“I am a late-stage entrepreneur, while continuing to serve on boards of Nestlé and Nykaa, and that is what my life is centred around today. What I’ve learnt is simple—entrepreneurship at a later stage in life gives you the freedom to define your own terms. No one gets to decide when you should retire. The energy remains the same as it was at 40; what grows stronger is wisdom, networks, perspective and the courage to build with far greater conviction,” says Parida.
Senior founders bring with them something that younger founders often spend years trying to build—credibility, relationships, industry knowledge and a deep understanding of how businesses actually work.
THRILL OF CREATION
For many, the trigger is surprisingly similar. After years of operating at scale, they miss the thrill of creation.
“At a certain scale, the job stops being about creating something new and becomes about protecting and optimising what exists,” says Ritesh Srivastava, 51, who spent 16 years leading and building data and AI strategies in large organisations, with leadership roles at Jindal Steel and BharatPe. That realisation led him to launch Tavastra, a startup accelerator focused on co-creation, in 2025.
Like many executives making the leap, he wasn’t looking for another big corporate role. He was looking for the zero-to-one journey again—the messy, uncertain phase where ideas are still being shaped and every small win matters.
The startup ecosystem has also changed dramatically. Technology infrastructure that once required significant investment is now available off the shelf. Products can be built faster and cheaper than before.
But if starting has become easier, succeeding has not. “The hard part has moved,” says Srivastava. “It’s no longer mainly the engineering. It’s distribution and sales.”
That observation resonates with 53-year-old Abhijit Tannu, who has cofounded Mavs AI, which helps organisations use generative AI without exposing sensitive information. Before that, he held leadership positions, including as CTO at L&T Infotech and Seclore.
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For Tannu, the question was straightforward: why start over at 50-plus when a comfortable advisory career was available?
The answer arrived soon enough. “Mavs AI was actually born over a cup of chai,” he says. The idea emerged during a discussion with the CIO of a bank whom he had known for years. What began as a casual conversation evolved into a business.
It is also a reminder of one of the biggest advantages senior founders possess. Trust. “That doesn’t happen to a 25-yearold who is cold-emailing strangers,” says Tannu. “It happens because of trust you’ve compounded over years.”
Those relationships become sounding boards, design partners and customers. The ability to call someone who will give honest feedback can shorten the journey from idea to execution.
Harit Nagpal, CEO of Tata Play and an investor in a handful of startups including Parida’s Tvarra, says backing an early-stage venture is fundamentally about betting on the individual rather than the product itself.
“When we invest in a startup, we are not investing in a product, we are investing in a person. Every startup is essentially an experiment, and what you are really backing is the experimenter. The more experienced the entrepreneur, the greater the courage and conviction they bring to navigating uncertainty. Not every experiment unfolds the way you envision, and knowing when to course-correct requires judgment that often comes with experience,” he says.
Citing Alpana as an example, Nagpal says she demonstrated exactly that quality — the willingness to take a bold bet and, when the original plan ran into challenges, the ability to pivot decisively and reshape the venture.
“Not every employee becomes an entrepreneur. Those who think entrepreneurially eventually make that leap. In the end, entrepreneurship is less about where you work and more about an attitude towards taking risks, adapting quickly and building something of your own.”
Srivastava says a senior executive’s track record changes the nature of conversations with investors and customers. As they have managed scale, unit economics and complex tech rollouts, they spend less time establishing credibility and focus more on execution.
Mitra sees a similar advantage. Humanizetech. ai operates in a business-tobusiness environment where access to decision-makers matters. The network Mitra and colleagues have built over decades is one of the company’s valuable assets. “The credibility and trust in that network are the biggest assets,” he says.
Yet if experience provides advantages, entrepreneurship extracts a different price.
The biggest challenge, founders say, is not money. It is ego. The corporate identity that took decades to build can disappear remarkably quickly.
For founders who start late, entrepreneurship often begins with a hard question: what are you willing to walk away from to build something new?
Falguni Nayar knows that journey. She was 50 when she founded Nykaa in 2012. She says for latestage entrepreneurs, the real barrier is not risk appetite but sacrifice. Reflecting on her decision to leave Kotak Mahindra Group, she says the shift demanded far more than giving up a paycheck. “When I quit Kotak, there was a lot I gave up— financially and in terms of position and the recognition that comes with it. Crossing that barrier is often the hardest part,” she says.
For founders who start later, entrepreneurship often begins with a harder question than ambition: what are you willing to walk away from to build something new.
Falguni Nayar believes that for late-stage entrepreneurs, the real barrier is not risk appetite but sacrifice. It means stepping away from financial security, professional stature and a deeply internalised identity. Reflecting on her decision to leave Kotak, she points out that the shift demanded far more than giving up a paycheck. “When I quit Kotak, there was a lot I gave up, financially, in terms of position and the recognition that comes with it. Crossing that barrier is often the hardest part,” she says.
That mindset, she suggests, requires a reorientation of what success looks like. Drawing on Ithaka, the poem by Constantine P. Cavafy that her daughter Adwaita once shared with her, Nayar sees entrepreneurship as a journey where the value lies as much in the experience as in the outcome. The learning, setbacks and evolution along the way are not by-products. They are the point.
A firm believer in compounding and long-term commitment, Nayar argues that building something meaningful requires optimising for enduring outcomes rather than immediate rewards. “It is about complete conviction, what we often call dhun sawar hona, where commitment, including the monetary commitment, has to be substantial,” she says.
In that sense, age can be an advantage. While younger founders may spot emerging ideas early, executing at scale often demands the judgment and pattern recognition that come with experience. For Nayar, the edge lies in the ability to stay the course on ideas that may not yet have widespread validation.
“The people who succeed,” she says, “are often those willing to back what others don’t see yet.”
PAST LIFE
Mitra recalls one of the hardest adjustments he had to make after leaving the corporate world: “You realise that the brand your business carried had a significant role in your recognition.” The phone does not ring as often. Emails can go unanswered. Meetings are not automatically confirmed.
The lesson, he says, is perseverance without entitlement. “The startup world is like a blank slate. It gives you an open canvas, but it also takes time to find the colours that make the picture beautiful.”
For executives accustomed to leading large organisations, the shift can be humbling.
Corporate life comes with an invisible support system: HR, legal, finance and operations teams and specialists who quietly solve problems in the background.
Founders soon discover how much of that infrastructure they relied upon. “The sharpest change is losing the institutional safety net,” says Srivastava.
The founder becomes responsible for every thing, from strategy and fundraising to operational details that would never have appeared on a corporate executive’s desk.
Tannu remembers catching himself thinking: “I used to have people for this.” In his previous roles, teams executed plans. In an earlystage startup, the presentation deck, customer follow-up and product issue often return to the founder.
Yet what initially feels humbling later becomes liberating. “There’s an honesty to building with your own hands,” he says. “I’m closer to the product, closer to the customer and learning faster than I have in years.”
There are other changes too at the leadership level. Large organisations reward alignment, predictability and risk management. Startups demand speed, adaptability and direct action. The founder’s behaviour becomes the culture.
Tannu recalls a recent customer issue. His team found the problem did not originate from their product. The easy way would have been to point that out and move on. Instead, he joined the call and helped solve it . “I didn’t give a speech about customer-first culture. I just did it.” In a startup, culture is rarely built through presentations. It is shaped through daily actions. “When you build from scratch, you are the culture,” says Tannu.
LATE-STAGE FOUNDERS
Investors are increasingly paying attention to this emerging founder profile
Davesh Manocha, founder of early-stage investment firm CDM Capital, says the number of senior executives launching startups is steadily rising. But experience alone is not enough. “We assess whether they can use their industry expertise, networks and credibility to create an advantage while showing the adaptability, speed and resilience needed to build an early-stage company,” he says.
The strongest signal, says Manocha, is not age but the ability to combine domain expertise with founder-like urgency. That can be particularly valuable in enterprise software, fintech infrastructure, manufacturing, compliance and other sectors where trust, regulation and long sales cycles create barriers that experience can help navigate.
As Nayar says, while younger founders may spot emerging ideas early, executing at scale often demands the judgment and pattern recognition that come with experience.
For years, the startup ecosystem celebrated the mythology of youth, the first-time founder, the college dropout.
But another set of founders is here. They arrive with decades of operating experience, hard-won industry relationships and a clearer understanding of customers that many younger founders don’t immediately possess. They are not starting companies because they need a job. They are doing it because they still feel the pull of building.
The irony is hard to miss. After spending years climbing the corporate ladder, many are drawn back to the beginning, to small teams, uncertain outcomes and the possibility of creating something from scratch.
The corner offices may be behind them. The entrepreneurial itch, it turns out, is not.
And for a growing number of executives in their 50s and 60s, the question is no longer whether they can take the risk. It is whether they can afford not to.
As Jagdish Mitra puts it: “Ab nahin to kab?”