Why Being a Founder is the Most Challenging Thing You’ll Ever Do
By: Elizabeth Van Rooyen
Tags: Entrepreneurship, Business, Venture Capital, Life, Startup

So congrats — you’re a founder! You’ve leapt into the unknown and done something most people will never have the guts to do. At first, it’s all excitement, and you’re full of juice. Then — slowly — customers start churning, deals fall through, people screw you over (because yes, that’s business). And gradually, your doe-eyed optimism fades, you find the weight of the world on your shoulders, and pressure rising while motivation diminishes.

As NFL player-turned-venture-capitalist, Ryan Nece, aptly said in one of my favourite podcasts with Notation Capital,

“I would much rather run down the field and hit a 300lb lineman over and over again than start a company from zero.”

As a founder, most of your time may seem spent running into linemen time and time again, weakening your physical and mental strength each time you get up to run towards the end zone.

I went to a talk by a FinTech entrepreneur not long ago, who was relaying his most vivid memory since founding his company. He recalls sitting at his desk years ago on the eve before his startup’s monthly pay run, with his three maxed credit cards beside him, and only enough runway for one more pay cycle after a recent funding round had collapsed. A week later, they landed their largest enterprise client at the time, who committed to a year’s subscription in advance. This led them to close several other high-value deals, which had investors banging their door down — and now the company is worth $500m+.

However exhausted you get, and — as tricky as it is to imagine — your next touchdown is just around the corner.

This is proven by many multi-billion dollar companies and their founders, who didn’t have the most natural starts to their now-empires. Here are some of my favourite stories of the greats that might make you feel better when clutching your next credit card bill:

Founders of Airbnb, Brian Chesky & Joe Gebbia

The accommodation booking platform we all know and love, Airbnb, initially started as a quick way for the struggling designers to earn enough money to pay rent in their San Franciscan loft. Brian and Joe began renting out air mattresses on their floor for $80/night. Now at a reported valuation of $31 billion, they are one of the most valuable startups in the world.

Co-Founder of Twitter, Evan Williams

Evan Williams first began with a startup called Odeo, a podcasting platform which was successful to the point of raising their Series A round before being made irrelevant by iTunes’ launch of Podcasts. Instead of claiming defeat, Williams and fellow Odeo creators began refocusing Odeo to centre on publishing 140 character ‘statuses’. Twitter was born — which is now one of the most successful social media platforms to date.

Founder of Apple, Steve Jobs

Steve Jobs founded Apple out of his parent’s garage at age twenty and turned it into a $2bn company within ten years. He was subsequently fired from his own company by Apple’s Board. This led Jobs to create a competing company, NeXT, to sell high-end computers. Apple eventually bought NeXT for its operating system and Jobs was once again back at his baby, and built it to the Apple we all know and love today.