By choosing purpose and principles over traditional metrics, zillennial founders are having their cake and eating it, too

Before Barack Obama hit the campaign trail for Kamala Harris, he made an unexpected appearance at his rally 16 years ago — not in person, but on a cereal box. Back then, Brian Chesky and his co-founders were desperate to save their struggling startup, with maxed-out credit cards and no funding in sight. They took a chance producing limited-edition cereals of presidential candidates, including “Obama O’s”, a move that gave them the financial lifeline they needed.

Today, that startup — Airbnb — operates in more than 100,000 cities worldwide, with 26 offices, 6,907 employees, and an estimated global economic impact of $100 billion.

Brian Chesky, now 43, was just 27 when he co-founded Airbnb. Like other prominent founders — Jeff Bezos (30), Steve Jobs (21), Mark Zuckerberg (19), and Bill Gates (19) — Chesky was considered a young entrepreneur. Paul Graham, founder of Y Combinator, once remarked that venture capitalists often view 32 as a cutoff, saying, “After 32, they start to be a little sceptical.”

It’s an attitude echoed in research. MIT professor Pierre Azoulay and his team published a paper in 2019 titled “Age and High-Growth Entrepreneurship”, which found that the average age of successful entrepreneurship was 42. For high-growth startups, only 10 per cent of founders are 29 or younger. 

Yet, despite the odds, young founders under 35 run approximately 42 per cent of all new firms. While just 4.6 per cent successfully scale up, these companies play an essential role in encouraging a wider risk-taking appetite and bringing about high-value productivity gains.  

Workplace ninjas

Does this mean that young founders should be discouraged from starting a venture? 

Not quite. A recent 2021 paper by economists Kathryn Shaw and Anders Sørensen found that young founders who become serial entrepreneurs see revenues nearly double between the first and second firms. Early experience in building a business, even if it doesn’t become a unicorn, often lays the groundwork for future success. 

More than ever, there is a renewed definition of what “successful” entrepreneurship means to young founders. Compared across generations, youths today are 1.6 times more likely to start a business, and in Asia, almost three-quarters of them aspire to do so before 40. For many, the optimal age is around 27.

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This age range is currently occupied by a generation between millennials and Gen Zs (for Gen Z slangs by McKinsey, see here), called zillennials (also called “cusper”). While there is no Pew Research Center definition for this sandwiched generation — most accept it broadly as between the 1990s and 2000 — there are some popular indications. Zillennials grew up in a unique era: sharing a family computer, moving from portable CD players to iPods, and witnessing the rise of YouTube and social media influencers.

More distinctively, zillennials are less driven by the wild commercial success that once defined entrepreneurship and more by purpose and meaning. This was partly influenced by the coming-of-age period that saw a generational recession, pandemic, wars, and massive layoffs, putting traditional trappings of success — house, family, cars, career ladder — out of reach. Instead, they aim to build businesses with social value, appealing to “inclusive, sustainable customers” who prioritise DEI, community, and environment.

Yet, this generation carries the “hustle” tradition of the millennials (“Girlboss” era), where the goal is to outperform and be great at what you do. They sit at the middle ground, constantly pushing and pulling, wanting to be the best but also wanting to slow down and seek meaning. 

This middle-straddling has given rise to the view that zillennials make the best managers. As ‘workplace ninjas, ’ they navigate the generational mix in the workforce — boomers, generation X, millennials, and Gen Zs — while being accountable for delivering what is necessary to keep the lights on. 

What zillennials teach us

But this balance comes at a cost. Increasingly, the psychological price of being a young entrepreneur has surfaced. The many roles of making payroll, meeting investor targets, organisational disputes, and vicious competition often are “traumatic events” that come with young businesses, especially with startups’ innate high risk of failure. 

For zillennials, this is incredibly taxing, as they try to create more egalitarian, open, well-being-centred, and flat workplaces while striving to meet the excruciating demands of financial targets, especially during funding winter. “It’s like a man riding a lion,” a young entrepreneur described. “People think, ‘This guy’s brave.’ But he’s thinking, ‘How the hell did I get on a lion, and how do I keep from getting eaten?’

Seeing how zillennials straddle between generations of almost opposing ends is not just observing a generation transitioning — it offers lessons. It shows us that while meaning and purpose at work are essential, the hard work and grind, including the unpleasant parts, matter in building something that lasts. 

Ultimately, toxic expectations and disregard for well-being can be as damaging as financial failure. Identity need not be tied to work and our career is not nothing — it could be our community, a place of self-expression, and where we find satisfaction. This, I believe, is not just the zillennials’ quiet whisper — it’s a powerful reminder of the future we’re all shaping together.