Recently, at a gathering of corporate professionals, someone asked me if I would trade my e-commerce pioneer status to that of an entrepreneur who followed the e-commerce trend a decade later and achieved financial success. It was an interesting question, because behind every celebrated success or tragic failure lies a hidden truth: timing and luck shape startup outcomes more than strategy or execution.
Airbnb launched in 2008, right in the middle of the global financial crisis. Homeowners were desperate to make extra money, and travellers wanted cheaper stays. Perfect timing. Now imagine Airbnb launching in 2005, during the housing boom. People were flush with cash and didn’t need to rent out spare rooms to strangers. Airbnb may have remained a quirky idea or a failed experiment.
At Indiaplaza, India’s first e-commerce startup, we built from scratch content aggregation, logistics, online payments, and customer education in 1999, long before the country was ready for online shopping. Internet penetration was low, credit cards were a luxury, and the market didn’t exist yet. A decade later, Flipkart launched in a transformed ecosystem consisting of cheap data, smartphones, venture capital support and cash-on-delivery. Same idea, different timing.
Timing can create new industries overnight. Paytm was building a wallet app in November 2016 when demonetisation, a once-in-a-lifetime policy shock, made digital payments a national obsession. Millions of Indians downloaded Paytm, and a fintech startup became a household brand overnight. A stroke of luck few business plans could predict. Zoom had been quietly growing for years when the pandemic hit in 2020 and, suddenly, it became the world’s default communication platform. On the flip side, Oyo Rooms, which had been expanding aggressively, saw its business collapse overnight when Covid struck.
Webvan, the American online grocery startup from the dot-com era, built massive warehouses and logistics networks, burning over a billion dollars before people were even comfortable shopping online, and collapsed spectacularly. Two decades later, the same idea is thriving globally, thanks to smartphones and changed consumer habits.
Timing can also destroy market leaders. BlackBerry dominated the smartphone market in the mid-2000s but failed to pivot when touchscreens and mobile internet took off. Apple and Android seized that moment with a much sharper sense of the turning tide.
Such stories underline that luck, often in the form of macroeconomic cycles or consumer readiness, influences startup outcomes. That doesn’t mean founders should simply surrender to fate. Skill still helps entrepreneurs survive long enough for luck to find them. You can’t control the waves, but you can learn to surf.
So the next time a startup soars or crashes, look beyond the headlines and ask what if they’d started five years earlier, or five years later? The answer might just be the real story behind every “overnight success”.
(The writer is a serial entrepreneur and best-selling author of the book ‘Failing to Succeed’; posts on X @vaitheek)
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Published on November 10, 2025
