Startups: The Untold Reality Behind The Glittering Success Stories

I came across this fascinating podcast last week – Hosted by Deanne Rhynard the discussions centre around the realities behind success stories. The f’ing up podcast aims to ‘normalise the feelings of failure we all experience throughout the career journey’.

From founding doomed startups to big successes and then back again I wanted to explore some of the stories I’d heard from founders or people I’ve met over the years as well as some of the more well known anecdotes. This is all in a bid to highlight the fact that for many, more time is spent failing winning! But that is ok – by discussing this and understanding the environment we find ourselves in we can build up more collective resilience.

Much in the same way that social media can portray a very inaccurate picture of reality, the hyped stories of startup founders and their successes can give younger product practitioners a false sense of hope as they embark on their career.

Financial Struggles

Despite its current status as a household name, the journey of Airbnb’s founders, Brian Chesky, Joe Gebbia, and Nathan Blecharczyk, was far from glamorous. In the nascent stages, they grappled with financial instability, resorting to selling cereal boxes to sustain their venture. Remember Airbnb is over 15 years old! Another thing to note is that the companies or unicorns that we see today have often been around far longer than you think. In 2008 Airbnb got $20,000 funding. IN 2023 it was worth more than $75BN.

Emotional Toll

Before Instagram became a billion-dollar acquisition for Facebook, co-founder Kevin Systrom navigated a tumultuous emotional landscape. Moments of self-doubt loomed large, and there were instances when he contemplated abandoning the venture altogether. Even a rebrand in 2016 made international news when the new logo was lamented by so many users. You can read more about Instagram’s journey here in ‘No Filter: The inside Story of Instagram’ 

Another more personal story comes from a friend of mine who successfully exited his entertainment business a few years ago. Whilst financially he is set for life he always regrets that he didn’t spend time with his children in their formative years – no amount of money can ever compensate for that.

Team Dynamics

Uber’s ascension to success was marred by reports of a toxic workplace culture and internal discord among its leadership. Former CEO Travis Kalanick’s aggressive management style and controversies within the company cast shadows over its journey. Uber’s story is symptomatic of many ‘successful’ product companies. Success may mean they become a household name, an indispensable app on your device and have hundreds of millions of users a month but underneath all of this are many facets that are not so rosy. Lack of profit, toxic culture, continuous lay-offs and poor mental health of employees are just some of the knock-on effects that permeate many tech companies.

Market Challenges

I helped set up Mind Candy 20 years ago. After a false start the company went on to reach hundred million dollar valuations, everything seemed set on a wild exit. And then the failure to move to mobile meant that suddenly the world of Moshi Monsters was no more. CEO Michael Smith left and turned to meditation to deal with the incredible stress that journey had cost him. His timing could not be more on point – after co-founding, a reaction to the very stress that the failure of Mind Candy had caused him, he went on to build a mental health empire which is now worth $2BN.


When I moved into the start-up world in my early twenties I drunk the KoolAid. I was told that I would be a millionaire. That we would be changing the world. Reach a billion users. And so on. Some of these things may have happened. Some did not. But what I was not prepared for was the enormous pendulum effect of this world that ricochets from euphoric success to abysmal gut wrenching failure. There are some entrepreneurs who play the long game – an old friend of mine for example has moved from a music start-up in the 90s, to a T shirt start-up in the 2000s and to online streaming now. He’s trodden a solid, steady path and has slowly built his own personal empire both financially and in terms of corporate achievement. He hasn’t had the abject failures that I’ve witnessed in most other organisations. But he’s the minority. Most successes I have encountered and even my own have been fraught with difficulty, uncertainty and failure after failure.

If you’re considering embarking on any journey (even outside the start-up world) then know that you have to be passionate, work extremely hard and be persistent above everything else. What I see in individuals who have eventually landed on their feet is this relentless belief that no matter what they will succeed. Behind every success story are a hundred failures. Be kind to yourself and others if you’re on this road!