Dust Yourself Off & Try Again: 8 Famous Founder Failures

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BUSINESS STORY 🗞️

How Failure Breeds Success

In the world of entrepreneurship, success is glorified, while failure is swept under the rug. The truth is, failure is an inevitable part of the journey to success. Many of the most successful entrepreneurs and business leaders we know and love today have experienced major failures before achieving their breakthroughs.

And while we sweep it under the rug—we shouldn’t. There is something about about failure that we really get behind. Humans love an underdog story. David vs Goliath, LeBron James vs the 2016 Golden State Warriors, Rocky vs Ivan Drago. It takes courage to fail and try again.

Wanna be as successful as Rocky? Read on.

But don’t take my word for it. Rocky Balboa said it himself; “It ain't about how hard you hit. It's about how hard you can get hit and keep moving forward.” Let’s dive in and take a look at some great leaders who took a knockout punch but climbed their way back up from the canvas.

Sir James Dyson & his 5217 failures

I’d like to get us started by highlighting a famous inventor, industrial designer, farmer, and entrepreneur who has failed more than most in history—Sir James Dyson of Dyson company.

*And yes, this is the guy that invented that gross but somehow awesome hand dryer you use in every airport you visit through.

Credit; Stuart McClymont.

Dyson’s most famous invention is the ‘bagless vacuum cleaner’ using cyclonic separation, inspired by a sawmill that separated sawdust using centrifugal force.

But this story is about the science of suction, this is the story of a man who was determined to bring an idea to life—no matter how much the mischievous twins of failure and bewilderment wreaked havoc with his plans.

Supported by his wife's salary as an art teacher, it took Sir James thousands of attempts, but he finally broke through.

I made 5,127 prototypes of my vacuum before I got it right. There were 5,126 failures. But I learned from each one. That's how I came up with a solution. So I don't mind failure. I've always thought that schoolchildren should be marked by the number of failures they've had. The child who tries strange things and experiences lots of failures to get there is probably more creative.

- Sir James Dyson

The first Dyson, the DC01.

No comment really.

Before long the Dyson became synonymous with the industry and household goods and he went on to create the Airblade hand dryer, bladeless Air Multiplier fans, the Supersonic hair dryer, the Corrale straightener, and many more products used across the globe today. Dyson’s net worth is estimated at over $13 billion dollars today.

The super pumped, Travis Kalanick

Although Travis Kalanick is often spoken of in the same breath as disgraced landlord-cum-billionaire Adam Neumann, he actually created a company, Uber, that is incredibly valuable today. And then he went on and did it again with the lesser known CloudKitchens—most recently valued at $15B.

A polarising figure in tech.

His first venture, Scour, ended in bankruptcy due to a $250 million lawsuit by 33 of the world's biggest media companies, and his second, Red Swoosh, had financial troubles before he co-founded Uber.

Fashion designer Vera Wang

American famous fashionista Vera Wang, best known for her elegant and sophisticated wedding dress and haute couture collections, didn’t hit the ground running success wise. Born in New York City in 1949 to Chinese immigrant parents, for most of her youth Wang pursued figure skating, aspiring to compete in the Olympics. Unfortunately, she bombed out of the 1968 U.S. Olympic team, leading her to transition into whatever came next.

Young Vera.

Design #1.

Next for Vera was college, followed by an entry-level job at Vogue magazine. She rose to senior fashion editor, a position she held for 17 years, but was eventually overlooked for the editor-in-chief role in 1987. She resigned from Vogue to join Ralph Lauren as a design director, but it wasn’t until she turned 40 that she would start her own business. Thanks to that business, Vera today has a net worth of $250 million dollars.

Walt Disney

Walt Disney’s imagination and entrepreneurial spirit helped shape modern entertainment, but his early foray into business didn’t signal he was second coming of Jesus for creativity. Born in Chicago in 1901, Disney’s love for animation was there from a young age. He founded Laugh-O-Gram Studios after working briefly in advertising.

Walter Elias Disney.

Despite local buzz and modicum of success in their retelling of famous fairy tales, Laugh-O-Gram filed for Chapter 11 bankruptcy in July 1923 due to ‘poor business management’. 

The main reasons for their struggles was a partnership gone bad. Young Walt and company had a contract for six animated shorts with Pictorial Clubs, Inc. of Tennessee, with Pictorial agreeing to pay US$11,000—equivalent to $200k+ today. The problem was they only paid $100 in advance and went bankrupt a few short months later.

Little Red Riding Hood.

Undaunted, Walt packed his bags for Hollywood, where he and his brother Roy founded Disney Brothers Studio. They would create Oswald the Lucky Rabbit shortly after, only to discover their distributor had taken ownership of the rights and the animators. Chalk that down as failure numero dos for the visionary Walt Disney.

The loss of Oswald led Disney to create a new character, Mickey Mouse, in 1928. The character’s popularity went crazy with the release of ‘Steamboat Willie,’ ushering in a new era of animated sound cartoons—as they were called at the time. The rest is history.

Disney went on to pioneer feature-length animation with ‘Snow White and the Seven Dwarfs,’ which revolutionised the industry, and helped Walt expand into television, theme parks, and live-action film, creating an empire now spanning Mickey Mouse to ESPN.

Bonus: The Disney flywheel

The business flywheel—more recently made famous by Jim Collins in ‘Good to Great’ and also in the content marketing of Hubspot—was also something Walt focussed on. In the 1950s, years after his failed beginnings, Walt detailed a flywheel that created momentum across all of his business assets.

Merchandise licensing fed into his parks, which in turn fed into his studio and theatrical films, which would then feed into music and tv and Marvel, and Star Wars, and Ratatouille (ok, not these last few) and so on and so on.

The Disney flywheel.

It’s a powerful concept that I have loved since I understood it and this image shows the innovation and foresight Walt had in what he was building. Not all of these elements have stood the test of time—but most have.

Jack Ma of Alibaba

Jack Ma, the founder of Alibaba, had a difficult path to becoming one of China's most successful entrepreneurs. His story is a lesson in overcoming adversity. Ma was born in Hangzhou in 1964, and faced a mountain of rejections in his formative years.

Ma, far left.

After graduating from Hangzhou Teacher's Institute in 1988, Ma applied for countless jobs—including the infamous application at a local KFC—but was rejected from all of them.

I went for a job in the police department but they didn't consider me eligible. When KFC started in my city, I even went there. There were 24 applicants out of which 23 were recruited except me.

- Jack Ma

Eventually, he found work as an English teacher, earning a modest salary. His early entrepreneurial efforts also included a translation business and a failed directory called China Pages.

But the failures did not stop there. After he failed many of his high school exams, Ma failed to have his Harvard application accepted 10 times.

83% sure this is legit.

After founding Alibaba, he failed his bid for US expansion. He failed in a role-reversing takeover of Alibaba investor, Yahoo, when they hit leaner times. And he failed to make any logical sense a few years ago, when debating Tesla founder, Elon Musk.

As of May 2024, Alibaba has a market cap of ~$186 billion dollars and Ma—a personal wealth of $25 billion.

Colonel Harland Sanders

Kentucky Fried Chicken (KFC) founder Colonel Harland Sanders—yep, real person/moustache—was a relentlessly determination character. Born in 1890 in Indiana, the Colonel had a tumultuous early career, working a slew of jobs such as a farmhand, insurance agent, and steam engine stoker (that sounds hard).

In the 1930s, he moved up in the world, running a small service station in Corbin, Kentucky, where he served homemade fried chicken to passers by. His unique blend of 11 herbs and spices was a major hit, leading to Sanders opening a restaurant and motel.

Does he look like your grandpa or is it just me?

In the 1950s though, disaster struck. Construction of a new interstate highway was set to bypass his restaurant, and the Colonel was forced to sell the property at a loss. Broke and living on a small pension, he drove across the country pitching his fried chicken recipe to restaurant owners. He offered franchises in exchange for a small commission on each piece of chicken sold.

Over a thousand rejections later, he found his first partner and began building what became a franchise empire. By the 1960s, KFC was booming globally, and Sanders sold the business for $2M while remaining the company’s spokesman. Today there are 25,000+ finger licking’ good KFC outlets in more than 140 countries around the world.

J.K. Rowling’s Chamber of Failures

Joanne Kathleen Rowling—or J.K.—began writing Harry Potter in the early 1990s while struggling as a single mother. Finding it tough to provide for her daughter, she wrote the manuscript for ‘Harry Potter and the Philosopher's Stone’ in cafes around Edinburgh, famously using her daughter’s nap time to build out her wizarding world.

Author of the year.

In simpler times.

After finishing the book, Rowling sent the manuscript to 12 different publishers and faced rejection from each and every one. Finally, Bloomsbury Publishing agreed to publish the book, influenced by the publisher’s young daughter who loved the story. Despite an initial print run of only 500 copies, the book quickly gained traction, and Harry Potter became the cultural phenomenon we know today, selling 500 million copies, and leading to films, merchandise, theme parks and a soon to be released HBO series.

Q: Are 2nd time founders actually more successful?

While preparing for this piece I took a little look into the data around second time founders and whether they are in fact, more likely to succeed. To be honest, what I found (hard to find good data on it, this is ancient) was conclusive, but not stark. Here is what we found:

  • First-time small business owners have a success rate of 18%.

  • Business owners who failed in the past have a slightly higher startup success rate of 20%.

  • Business owners who started a successful startup in the past have a business success rate of around 30% when starting a new venture.

To be honest, I was a little underwhelmed. We have been told that we learn from our mistakes and come back bigger and better again. ‘What doesn’t kill us only makes us stronger right?‘ Well that data does indeed back that up—but 2%?

I did find the data I expected to see in a chat with Anthropic’s Claude, the problem is it refused to give me sources and after tireless searching I finished with the stance that this was actually a hallucination.

You suck Claude.

The hunt for more data really did turn up dry. The debate was raging on Reddit a couple of years ago, and I also found the same discussion on Hacker News all the way back in 2008.

Advanced maths x 1 trillion.

If it is in fact 2% benefit from all the learning you have from your first failures then it is still meaningful. In business, every day is a fight until your dying breath, so if you can scratch and claw your way to a couple of extra basis points, you’d take it.

Bill Gates and Traf-O-Data

The man synonymous with Windows 95 and the greatest software launch in living history, Bill Gates, also failed at his first startup venture. Yes, sure, he was 17 years old chronologically and 12 years old visually—but a failure is a failure.

Bill Gates & Paul Allen, Lakeside School, 1970.

In 1972, whilst still high school, Bill Gates and Paul Allen created a traffic data analysis system called Traf-O-Data, intending to provide traffic data processing services. They had a decent idea, but the business struggled due to technical issues processing raw traffic data using early microprocessor technology. They also had market challenges.

It seems municipal governments—their primary target—weren’t as interested in outsourcing traffic data as expected.

The failure taught Gates lessons about market and customer needs, which he applied when founding Microsoft, the most valuable company in the world today.

Traf-O-Data.

And another Bill—me

The least famous example from our list today, is me, and my first startup AdventureFit. We took people all around the world on adventure holidays. We trained, hiked and climbed our way all across the globe. All while drinking a few beers, enjoying a burger or two and having as much fun as humanly possible.

Base Camp, circa 2017.

And like most of our other entrepreneurs and their failures, I thought I was creating the greatest company in the world. But as Ernest Hemingway said in The Sun Also Rises; “How did you go bankrupt? Two ways. Gradually, then suddenly.”

I remember the moment I asked my team what they thought we should do moving forward, sometime in our fifth and final year of operations. They told me the truth—we should shut it down.

The moment I got off the meeting, I cried my little founder eyes out for a few minutes, then took a few deep breaths and moved on with my life.

And a load more famous failures

  • Milton Hershey. Experienced two failed candy businesses before perfecting a caramel recipe and finding success with Hershey’s chocolate.

  • Brewster Kahle. After the fall of his early company, Thinking Machines, his WAIS technology was commercially unsuccessful before he founded the Internet Archive.

  • Stephen King. Faced numerous rejections for his early work, and his first major novel, ‘Carrie,’ was initially discarded before being saved by his wife.

  • Sylvester Stallone. Struggled to find acting opportunities and lived in poverty before writing and starring in ‘Rocky,’ which became an international hit.

  • Abraham Lincoln. Lost multiple elections and faced early business setbacks before eventually becoming president and leading the nation through the Civil War.

  • Winston Churchill. After the Gallipoli disaster, he was sidelined politically and faced public criticism before returning to lead the UK through World War II.

Summary

The idea of this piece was not to tell you that if you try and fail, you’ll learn, and you’ll learn, and you’ll eventually inevitably be successful. No—the idea was to highlight the fact that we fail. We all do, for to fail is to be human.

But in that failure there is hope. Hope that maybe, just maybe, we can be the one that finally breaks through. I leave you with this quote from His Airness, Michael Jordan.

I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.

- Michael Jordan

And that’s it! I hope you enjoyed reading this one dedicated to all the famous failed founders out there.

TWEETS OF THE WEEK 🐣 

If you don’t already follow him—Aakash is a great follow on Twitter for all things product and technologu.

Same goes for Greg here. I love this take on revenue per employee. In January we instilled RPE as one of our core metrics at Athyna. So much so that it’s one of the 5 metrics in our company health check in our monthly All-Hands.

Oh yeah, and speaking of Athyna—here is a shameless plug for us. Keep us in mind if you are hiring globally. Incredible talent, matched with AI-precision, at lightning speed. That’s us.

BRAIN FOOD 🧠 

Interviewer: “Where are you taking Facebook at this point?

Zuckerberg: “There doesn’t necessarily have to be more. A lot of people are focussed on taking over the world or doing the biggest thing and getting the most users. I just want to focus on a really cool college directory product.”

Ambition grows over time.

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Apollo: We use Apollo to automate a large part of our 1.2M weekly outbound emails.
Deel: the only HR platform with everything you need, for everyone.
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And that’s it from me. See you next week. 🫡 

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