The Unexpected Journey: When Startups Succeed for Different Reasons
Instagram, Netflix, Slack – these platforms have become so integral to people's lives, it's hard to believe they began
The most successful startups often have the messiest origin stories. Whilst business schools teach you to stick to your plan, the real world rewards those who are smart enough to abandon it.
Instagram, Netflix, Slack – these platforms have become so integral to people’s lives, it’s hard to believe they began as very different products. What we call “overnight success” is usually the result of years of failed attempts, unexpected discoveries, and the wisdom to recognise when something isn’t working.
Here’s the uncomfortable truth about why startups succeed: the companies that make it rarely succeed for the reasons they originally intended.
When Your Side Project Becomes Your Main Project
Stewart Butterfield never meant to revolutionise workplace communication. His company, Tiny Speck, began developing a game called Glitch. After a brief launch in 2011, Glitch was returned to beta and by 2012, Butterfield declared the concept wasn’t viable. However, the internal communications platform Tiny Speck had created to communicate between US and Canadian offices turned out to be the real opportunity.
That internal tool became Slack. The messaging app Slack officially launched in 2014 and became a unicorn ($1B+ valuation) the same year. By 2017, Slack had grown to millions of daily active users and achieved a multi-billion pound valuation.
The game that was supposed to make Butterfield rich failed spectacularly. The tool they built just to coordinate their team changed how millions of people work.
This pattern repeats constantly in startup land. The thing you build to solve your immediate problem often becomes more valuable than the thing you set out to build. YouTube started as a dating site where people uploaded videos of themselves. Few people took advantage of YouTube’s value proposition, so its founders pivoted and let people upload videos of any kind.
Sometimes the most successful product is hiding in plain sight, masquerading as a feature or a tool.
The Wrong Target Market Can Be the Right One
Kevin Systrom built Instagram as something completely different. An early version, known as Burbn, included check-in features, photo-posting options, and the ability to earn points, among other functions. It was cluttered, confusing, and trying to do everything.
But Systrom and his co-founder Mike Krieger decided it was too cluttered, so they pared it down to only posting, comment, and liking features — and rebranded as the app users now know as Instagram. The simplicity of Instagram as a visual platform is ultimately what helped it stand out.
The lesson? Sometimes success means taking away features, not adding them. Sometimes it means serving a completely different audience than you originally planned.
Shopify’s founders learned this the hard way. Shopify’s founders launched the platform in 2004 as an online storefront for selling snowboarding gear, which was at the time known as Snowdevil. The e-commerce shop didn’t gain much traction, but the founders realized the platform they built had potential. The team decided to rebrand not as a store in and of itself, but as a way for other online retailers to sell their wares via the web.
They went from trying to sell snowboards to helping thousands of other businesses sell everything. The infrastructure they built for their failed shop became the foundation for a multi-billion-pound company.
Timing Beats Strategy Every Time
Bill Gross’s Ted Talk “The single biggest reason why startups succeed” revealed something that makes many entrepreneurs uncomfortable: timing is the single biggest factor that determines why startups succeed.
All the strategy in the world can’t save you if you’re too early or too late to market. Being too early is as bad as being too late to market.
Consider Zoom’s explosive growth during COVID-19. While Zoom was already gaining traction as a reliable video conferencing tool, its use skyrocketed during the COVID-19 pandemic when remote work and virtual meetings became the norm. The timing of the global shift to remote work played a huge role in Zoom’s explosive growth. But it doesn’t always have to be a major global event. Also, Zoom had already been there for 9 years to become an “overnight success”.
Nobody could have predicted a global pandemic, but Zoom was positioned perfectly when the world suddenly needed their solution. They succeeded not because they had the best product (there were plenty of video conferencing tools), but because they had the right product at exactly the right moment.
The same timing dynamics destroyed other companies. iExplore launched its site in February 2000 in the peak of the dot com boom. And then the dot com bubble burst in March 2000, a month later, making it immediately an uphill slog right out of the gate. Had we launched three years earlier, riding the momentum of the dot com boom wave would have made it much easier to grow the business. Or even worse, nobody could have predicted 9/11/01 and the negative impact that event would have on both the economy overall, and especially the travel industry.
Perfect timing often looks like luck from the outside, but it’s usually the result of being prepared when opportunity strikes.
When Your Customers Use Your Product Wrong (And That’s Right)
Some of the biggest successes come from companies that noticed their customers were using their product in completely unexpected ways.
Groupon originated as an online platform called The Point, which allowed people to come together to support causes that were important to them. When the company added a feature called Groupon that enabled users to collectively bargain for discounts, they found that it caught on far more than the cause-based functions ever had.
The founders thought they were building a platform for social activism. Their users wanted discounts on restaurants and spas. Smart founders follow their customers, not their original business plan.
Twitter faced a similar moment. Twitter launched in 2005 as Odeo, a platform for discovering and subscribing to podcasts. But thanks to iTunes, Apple loomed large in the podcast space, so Odeo decided to pivot. When Jack Dorsey suggested a microblogging platform during a company brainstorming session, nobody could have predicted it would become the primary communication tool for world leaders, activists, and anyone with something to say in 280 characters or less.
The key is paying attention to what your users actually do, not what you think they should do.
The Accidental Billion-Pound Mistakes
Netflix started by mailing DVDs to people’s homes. The company initially operated a mail-order service through which customers could order DVDs to rent that were sent directly to their homes. But as demands for digital content grew, Netflix not only began offering access to movies and TV shows online, it also began producing its own original programming.
They could have stayed in the DVD business. Blockbuster certainly thought that was the safer bet. Instead, Netflix cannibalised their own successful business model to chase something that seemed riskier but had more potential.
PayPal’s journey was even more convoluted. PayPal’s first foray into the payments space happened during the Palm Pilot era, and the platform got its start as a way of sending “IOUs” between personal devices, after initially launching as a security software company. The service didn’t catch on, but the company then shifted into enabling money transfers via email.
They went from security software to Palm Pilot payments to email money transfers to the payment processor that powers much of the internet today. Each “failure” taught them something that made the eventual success possible.
The Problem with Having a Plan
The startup world loves origin stories that sound clean and inevitable. “We saw a problem, built a solution, and changed the world.” The reality is far messier and far more interesting.
Most successful startups succeed because they were willing to:
Pay attention to unexpected signals. When users started using your product differently than intended, that’s data, not failure.
Abandon sunk costs. Just because you’ve invested time and money in an idea doesn’t mean you should keep pursuing it if something better emerges.
Follow opportunity over ego. Your original idea might be brilliant, but if the market doesn’t want it, brilliance doesn’t matter.
Stay curious about why things work. When something starts working unexpectedly, dig into why. That insight often contains the seeds of your real business.
Move fast when you spot the right moment. Timing windows don’t stay open forever. When you find product-market fit, even if it’s not what you originally planned, run towards it.
The Real Lesson
Understanding why startups succeed isn’t about luck—it’s about hard work that intersects with market timing opportunities. But luck favours the prepared mind that’s paying attention.
Why startups succeed has little to do with executing their original plan perfectly. They succeed because they were smart enough to recognise when their plan wasn’t working and agile enough to pursue something better.
Your startup probably won’t succeed for the reasons you think it will. That’s not a bug in the system – that’s the feature. The market is smarter than any individual founder, and it will teach you things about your business that you never could have planned.
The question isn’t whether you should have a plan. You should. The question is whether you’re willing to abandon that plan when you discover something better.
Because in the startup world, the most successful journeys are the ones that end up somewhere completely different from where they started. And that’s exactly as it should be.
