5 Businesses That Almost Failed and Why It Pays to Keep Going

Jayson DeMers
4 min readAug 6, 2020

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Photo by craig hellier on Unsplash

No matter how good or promising your business idea is, there will be times during your entrepreneurial career that you’ll question whether or not your company will ever be a success. The overnight, rags-to-riches stories of explosive popularity have permeated our collective startup culture, leading young and inexperienced entrepreneurs to believe that this is a typical trajectory for businesses, but this simply doesn’t reflect reality.

The truth is, most successful businesses experienced hardships, sometimes for years before finally turning a corner and experiencing a skyrocket in popularity and revenue. If their entrepreneurs had taken a look at the numbers and thrown in the towel, some of the biggest, most popular companies we know today would have never reached their cultural landmark status.

Take a look at these five companies as particularly enlightening examples:

1. Apple. Apple’s story is well-known to most of you, but it’s worth repeating for its sheer scale. Originally building early momentum and offering truly unique, game-changing products, Apple’s innovation and popularity plummeted over the course of 12 years after figurehead Steve Jobs left in 1985. At the time Jobs was rehired back in 1997, the company was operating at a loss and creeping closer and closer to bankruptcy every year. But after a successful rebranding campaign, a new iMac, and the steady restructuring of consumer expectations, Apple turned around to become one of the biggest and most successful companies in the world we know it as today. This, after a 12-year downward spiral.

2. FedEx. Most of us don’t remember FedEx suddenly emerging as a major logistics competitor — in fact, it’s been around since 1971, but not as the $30 billion corporate giant we know it as today. After a few years of steady operations, rising gas prices and logistics nightmares were causing the company to hemorrhage money, losing a million dollars a month. At one point, company funds got as low as $5,000; thanks to some skillful positioning (and a little Blackjack), the company managed to skirt past this colossal dry spell and become the self-sustaining profitable behemoth we all recognize.

3. Airbnb. Airbnb is another multi-billion dollar company, and one that is often recognized as a shooting star in the world of startups — a player that seemed to emerge overnight and grow into something monumental. However, this wasn’t exactly the case. When Airbnb started back in 2008, it struggled to find any footing; prominent investors all over Silicon Valley passed on the idea, and the team had to resort to some patchwork financial fixes — such as creating custom cereal boxes — to make ends meet. After unrelenting persistence, the team eventually found the investments they needed, and built the empire you know.

4. Evernote. Despite some recent trouble, Evernote has been a massively successful app (and company), and the clear leader in terms of note-taking and organization software. In 2008, when the company was still young, founder Phil Libin made the hard decision to shut the company down, once and for all, upon realizing that it probably was never going to take off. Then, in a strange twist of fate, an overseas investor pledged $500,000 to give the product more momentum — that one extra push was enough to give Evernote the foundation it needed to succeed.

5. Reddit. Reddit is currently one of the world’s most popular online platforms, with more than 169 million unique visitors per month, but it didn’t start out that way, and it nearly failed several times along the way. When it launched in 2005, it had zero visitors, like every other website at the time. After waiting a while and realizing the users weren’t going to come all by themselves, the founders started inventing fake accounts and holding fake discussions on the platform until some visitors started noticing and trickling in themselves. They essentially faked their way to the top upon realizing that the success wasn’t going to come by itself (or come easily).

What’s the moral of the story here? ‘Never give up’ seems a bit too clichéd and non-universal — there are definitely times when quitting truly is the best option. Instead, the moral is that you shouldn’t take the early signs of failure too literally or as unchangeable. Maybe you aren’t attracting lots of users, or maybe your revenues aren’t growing as fast as you’d hoped, but if you have a good product and a good team, there’s always a chance to succeed.

If you follow the above stories, the trend isn’t just “sticking it out until you make it.” All these entrepreneurs recognized that their businesses were failing, and decided to change something rather than let the idea die. If you believe in yourself, don’t let your ideas die — let them transform and get another chance at life.

For more content like this, be sure to check out my podcast, The Entrepreneur Cast!

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Jayson DeMers
Jayson DeMers

Written by Jayson DeMers

CEO of EmailAnalytics (emailanalytics.com), a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!

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