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HOUSEKEEPING 📨

Because my personal media diet seems to be a never-ending stream of negative news, I often escape by watching funny videos on YouTube, one of which I present to you below: the 100 funniest Red Bull soapbox crashes. I promise you it’s worth your time.

On a serious note, big hugs to all my Venezuelan readers. I have many friends in and outside of Venezuela, and I am thinking of you and yours today, and hoping that the events of the last 36 hours lead to a prosperous future for a sleeping giant of a country. Now, let’s dive into today’s post.

BUSINESS STORY 🗞️

Dust Yourself Off & Try Again: Famous Founder Failures

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 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.

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 the Dyson company.

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

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 before he finally broke through.

Before long, 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 worldwide today. Dyson’s net worth is estimated at over $13 billion dollars today.

The super pumped, Travis Kalanick

Travis Kalanick is often spoken of in the same breath as landlord-cum-billionaire Adam Neumann, for his ousting from Uber, the $172 billion dollar giant he co-founded. He has since done it again with the lesser-known CloudKitchens, which was most recently valued at $15B in 2021.

But it’s not all been sunshine and UberEats for Travis. His first venture, Scour, filed for bankruptcy after a $250 million lawsuit from 33 of the world's largest media companies, and his second, Red Swoosh, faced financial difficulties before he co-founded Uber. A double failure, before two ginormous wins.

Fashion designer Vera Wang

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

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 that he was the second coming of Jesus for creativity. Born in Chicago in 1901, Disney developed a love of animation from a young age. He founded Laugh-O-Gram Studios after a brief stint in advertising.

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 a focus for Walt. In the 1950s, years after his failed beginnings, Walt introduced a flywheel that created momentum across all 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, TV, Marvel, Star Wars, and Ratatouille (ok, not these last few), and so on and so on.

It’s a powerful concept 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.

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.

After founding Alibaba, he failed his bid for US expansion. He failed in a role-reversing takeover of Alibaba investor Yahoo when it 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 has a personal wealth of $25 billion.

Colonel Harland Sanders

Kentucky Fried Chicken (KFC) founder Colonel Harland Sanders—yep, real person/moustache—was a relentlessly determined 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 passersby. His unique blend of 11 herbs and spices was a major hit, leading to Sanders opening a restaurant and motel.

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 worldwide.

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.

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 to learn from our mistakes and come back bigger and better. ‘What doesn’t kill us only makes us stronger, right?‘ Well, the data does indeed back that up—but 2%?

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

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.

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 most significant 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.

In 1972, while still in 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.

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.

Like most of our entrepreneurs and their failures, I thought I was building 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 out of 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.

Further study

• The Four Types Of Managers & How To Manage Them - March, 2025

• The Negative CAC Media Pyramid - March, 2025

• Strategism: How Companies Are Owning Emojis - May, 2025

And that's it! You can follow me on Twitter and LinkedIn, and also don’t forget to check out Athyna while you’re at it.

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TOOLS WE RECOMMEND 🛠️

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