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– Nassim Taleb

“Being an entrepreneur is an existential, not just a financial thing.”

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Here's What We're Covering:

I am obsessed with origin stories. Every time I meet someone I want to know why they are the person they are.

If they are where I want to be then I go digging in their history for the secrets that got them to this magical place. This post is the result of years of digging for gold.

Something weird happens after collecting a certain amount of stories. It goes sort of like this (and I mean “sort of” in the most “sort of” sense):

  • 0-100 stories: You see paths beginning to emerge. You are convinced the key is out there.
  • 101-200 stories: You feel that you are on the cusp of discovering the secret.
  • 201-400 stories: You begin to see more subtleties. The keys that aren’t actually keys.
  • 401-700 stories: You see so many conflicting paths that you begin to lose faith in finding “a way”. The superficial differences fall away. You come back to the core attributes of entrepreneurs in a big way.
  • 700-1000 stories: You begin to appreciate the stories of entrepreneurs as stories—events colored heavily by terrible memories and the narrative fallacy. You fully realize the necessity of self-reliance to an entrepreneurial life while appreciating your dependence on others. The stories make you more self-aware and more present instead of making you feel there is another path you should be on. You realize the importance of context, temperament, and opportunity.
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For Every Entrepreneur, There is an Equal and Opposite Entrepreneur

Some entrepreneurs (John Rockefellar and Steve Jobs) read virtually zero books. Others read constantly and say it’s completely necessary (Charlie Munger and James Altucher).

Some entrepreneurs start with zero money (Oprah) while others started with silver spoons (Warren Buffett).

Some entrepreneurs succeeded huge right away (Mark Zuckerberg and others in the news) while others didn’t succeed until later in life (Ray Kroc, Colonel Sanders).

Some entrepreneurs start many businesses (Richard Branson) while others only start one or two (Sam Walton).

Some are obsessed with numbers; some with story.

Some succeed by improving products incrementally; some succeed by disrupting entire industries.

Some get talked about in the news constantly; some quietly show up in the Forbes 400 once a year.

Some have a passion for the product; some just have a passion for business.

Some were mentored; some were not.

Some closely followed systems that worked before; some totally broke the rules.

Some define themselves as entrepreneurs; some don’t.

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Why We Need Stories of Other Entrepreneurs

With all this conflicting information it may seem like there is no reliable lesson to learn from the stories of other entrepreneurs.

It is certainly a bad strategy to read the Steve Jobs biography, drop acid, start yelling at people and justify your delusions. Jobs broke every rule in the every business book out there. He was able to do that because he compensated in ways that you don’t.

Jobs’ biography is still a powerful tool for entrepreneurs.

Here are some of the ways we benefit from hearing the stories of other entrepreneurs:

  1. Our realm of possibility is expanded. These are stories from the real world. The world we live in. If other human beings have created situations like that then there is no reason we, as human beings, can’t do things of the same magnitude.
  2. They become humans. When you hear about Lincoln being depressed, Theodore Roosevelt being sickly, Richard Branson being dyslexic, Rockefellar not reading a thing, or any of the other weaknesses of other entrepreneurs our excuses begin to fall away. There is always someone who started from a worse place than you.
  3. You begin to see what kind of entrepreneur you are. You may read a book about Mark Zuckerberg and feel hopeless, then talk to an entrepreneur you meet and find his story more relatable.
  4. You get inspired to take action. Hearing about the adventures of others makes us want to go on an adventure of your own. You don’t get to venture into Middle Earth but you can prototype and sell that invention you’ve been thinking about for years. Hearing the story of another entrepreneur may ignite or re-ignite (and re-ignite and re-ignite) your fire to build your business.
  5. Entrepreneurship becomes redefined. When you see the wide variety of entrepreneurs out there you realize that an entrepreneur might not be exactly what you thought. The assumptions you had about what is required to become an entrepreneur might be wiped away.
  6. Your fears are made smaller. If you hear about someone navigating certain challenges you may find yourself more confident in your ability to tackle them.
  7. You may be given a direction. We live our lives according to narratives that we tell ourselves. These narratives are defined by what we take in. Oftentimes, a story of an entrepreneur will inspire us to move in a certain direction.
  8. We are given warnings. No two paths are the same. There are similar road blocks that we all find ourselves facing. Knowing about these ahead of time makes it much easier to face them. We may even be able to avoid certain road blocks. By standing on the shoulders of giants we can adventure further (and come back with stories about totally new road blocks for future travelers).

And now, the paths!

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17 Paths to Entrepreneurship

The following are proven paths of successful entrepreneurs. Some are famous entrepreneurs and some are unknown except to their friends. Some are from history and some are kicking ass right now. Some are billionaires and some haven’t become millionaires yet. Some are composites of a couple of real people.

These stories come from executives public companies to Internet marketers to YouTube celebrities.

(Note 1: I guarantee the essence of every story is dead-on but I am telling these stories from memory. Some details might not be exactly right. That’s fine because the important part is the path, the lessons learned.)

(Note 2: If you want to know more about any of these stories just let me know in the comments.)

(Note 3: This is a bit long. If you don’t want to read the whole thing, at least ready #17)

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1. Greg: College Dropout to Engineer to Salesman to Entrepreneur

Greg grew up with no money. He lived in a crappy neighborhood with a single mother who instilled in him the belief to upgrade their circumstances.

In middle school he began tinkering with robots. Later, he began engineering software.

He never finished college yet somehow (he knew his stuff) he got a job at IBM, then at a startup.

He thought he knew what was up so he started his own startup. It failed. He had a family to support so he went back to work.

He was making $100,000+ a year but his family was growing and growing. He wanted to make more money.

He looked around and saw that salespeople were often out-earning the executives of companies he was working at.

He learned to sell. He failed at selling for a while. He kept learning and got good at it. He started earning a ton of money.

He still hated working for other people and cringed at making so much money for someone else.

He private-labeled the product he was selling to gain some autonomy. After a while he was killing it with that, but felt that the quality of the product was holding him back.

He made the leap to entrepreneurship again. He hired a couple programmers and had them build a better piece of software.

He’s been leading his industry ever since.

The Path: Engineer >> Salesman >> Selling a private-labeled product >> Selling his own product.

Where did the leap to “successful entrepreneur” happen? When he began selling the private-labeled product on his own? When he sold his own product? Who cares?

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2. Ben: 6 College Degrees to Consultant to Executive to Entrepreneur

Ben grew up in poverty.

Then he accidentally had a kid when he was 17.

The most consistently profitable group of entrepreneurs I’ve interviewed have come from nothing. There is nothing in the world can make you appreciate money as much as a distinct lack of it. And there is nothing that can force you to do something about it more than having an infant’s hungry belly.

(Louis C.K. has said that the moment his daughter was born his career was transformed. He realized that he needed to treat his profession, well, professionally and from that point on has continued to elevate his success artistically and financially.)

Ben used the G.I. Bill to get educated 3 B.S. degrees and 3 Masters degrees in everything from computer science to psychology to management.

After college he worked at McKinsey Consulting (the most respected consulting agency around and a breeding ground for entrepreneurs and future executives) with the same intense drive that fueled him through college.

He then got on the board of a growing tech company and took it public. He did this a couple more times.

Then he went out on his own. He has started and sold 4 successful startups. Failed at 1. And is currently growing another.

The Path: College >> Consultant >> Executive >> Entrepreneur

This is the path taken by a lot of graduates of advanced business schools. It is becoming less popular as entrepreneurship becomes a more viable path on it’s own but it is still somewhat common.

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3. Johnny: Mowing Lawns to Mowing More Lawns to Paying People to Mow Lawns

Johnny grew up lower-middle class.

Early in high-school he realized that he wanted to buy more things than his parents could or would buy him.

So, like neighborhood entrepreneurs you read about, he began mowing lawns.

He gave away some free mowing services to get people hooked, then charged a minimal fee.

He kept knocking on doors and offering free cuts to get more customers.

After eight months or so his friend wanted to make some money. Johnny offered to pay him to help mow lawns.

Johnny kept mowing lawns for free and getting more customers. This meant he kept hiring friends to mow lawns.

When it was time to graduate Johnny’s parents pressured him to go to college. Mowing lawns is fine for a high school gig, but you really need a college education to make it in life. Nope, Johnny just wanted to mow more lawns.

Most of the friends he hired moved away to college and his workforce was cut in half… while there were a ton of lawns that needed cutting.

Johnny and his team put in insane hours to get all the lawns cut and immediately hired on some younger kids from his high school.

Johnny felt a new pressure to make this lawn care thing a real business. Between his friends going to college and needing to prove to his parents that he didn’t need to get a degree to “make it in life” he was driven to grow.

He began reading about business and talking to local business people. He continued to grow his business slowly. He expanded his offerings, hired an accountant, and pretty soon found himself too busy managing his employees to actually mow the lawns.

By the time his peers were graduating high school Johnny had made nearly a million dollars. He had a small fleet of trucks and knew more about business than any of his friends coming out of the top business programs.

Johnny kicked ass.

The Path: Provide a Service >> Pay Others to Provide that Service

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4. Pat: Crappy Office Job to Internet Marketer to King of Affiliate Sales

[Okay we’re 1900 words in and we’re on the 3rd story. It’s time for rapid-fire path analysis!]

Pat was an architect getting paid crap (most do). He listened to internet marketing podcasts every day on his commute.

He actually liked being an architect but his boss didn’t like him being an architect… so he got fired.

Inspired by the podcasts he listened to, he created an ebook that helped people pass the exam to become an architect. (He just packaged pre-existing knowledge into a form others could us.)

He began making a few thousand bucks a month and quickly made more money off that than he did as an architect.

Then he began teaching people about this brand-new skill set he had: making money from packaging your knowledge. (This meta approach has been uber-successful online—you just keep showing people how to do what you just did.)

Pat doesn’t charge for any of his knowledge but manages to make over $80,000 every month. Most of this money is coming from affiliate income. Nearly half of that revenue is from Bluehost. How?

  1. He gains trust with his audience.
  2. He recommends they use Bluehost.
  3. He made a video and blog post showing them how to use Bluehost.
  4. They buy Bluehost.
  5. Bluehost pays Pat.

The Path: Job>>Teach people how he got the job (make a little money)>>Teach people how he made money teaching people how to get the job (make a bunch of money)

5. John: Military to (Everything) to Podcasting to Teaching

John served in the military for 7 years after college. When he got back he set off to be a good civilian.

Law School was no good. Startup scene was no good. Real estate was no good.

He bounced around. While bouncing he started listening to podcasts.

The podcasts he wanted to listen to didn’t update often enough. He was on the road five days a week and they only put out podcasts one day a week.

Aha! John created the first 5-day a week business podcast.

The consistency and quality of the podcast rocketed it up.

People would not stop asking him podcasting questions. They wanted to know how they could create their own podcasts.

So, like Pat, John decided to teach what he had learned. Unlike Pat he would charge for his nitty-gritty instructional information.

He created a course and community to help people start and grow their podcasts.

He launched it for $200 at first. It was rough around the edges and there weren’t a ton of people in there. It grew over the next year, John added a ton of content, and the community took on a life of its own. Today he his charging $1200.

He made nearly $300,000 in August.

The Path: Military>>Bouncing Around Jobs>>Start and Grow Podcast>>Teach People to Start and Grow Podcasts

I should mention that his first attempt at making money (besides ads) with his podcast was a failure. Then he launched another product that pretty much failed. Then another kinda-sorta-not-really success. Only then did he create his podcast.

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6. Hugh: Rejected Writer to Accepted Writer

Hugh had been writing for decades but wasn’t able to sell anything.

He didn’t think of giving up, though. Not because he was so strong or anything like that. He just liked writing. If nobody ever bought his writing he would still write.

He was able to eat by captaining ships and working at a bookstore. He wrote every morning before working.

Hugh decided to start putting his writing up on a blog. He got involved with other writers online and discovered self-publishing.

He spent a bunch of years publishing to nobody but some weirdos online.

That group of weirdos grew. Slowly.

Then he published a short story that a lot of people liked. They liked it so much they passed it around.

Hugh wanted to give more of this story that was wanted. He wrote it and released it bit by bit.

It got so popular that a major publisher offered to publish it as one book.

Now he can release any book he wants whenever he wants.

Is he an “entrepreneur”? I don’t know. It certainly feels like it.

The Path: Write for fun (out of compulsion)>>Make money at day job>>Self-Publish for tiny group of people>>Get approached for massive deal by publisher.

7. Scott: Affiliate marketer to Author-Entrepreneur

Scott’s soul was sucked out of him by affiliate marketing (apparently not the fun kind) and so he went looking around for things to do.

He liked writing and he had heard about some authors making a decent living selling ebooks on Amazon.

He wrote a few, they didn’t sell.

He wrote a few more and they began to sell. He was writing about a book a month. Just 10,000-15,000 word documents about making money online.

Again, he got tired of talking about making money online. He made a series of fourteen children’s books. They bombed.

After a period of “damn it all” he went back to writing ebooks. This time he would write about things that he liked: personal development and habits.

These are all $0.99-$4.99 ebooks that Amazon mostly gives away for “free” now on their Kindle Unlimited program. Scott gets nearly $2 every time someone “borrows” one of his digital books for free from Amazon.

Last month Scott made more than $60,000.

You know what he’s working on now?

Exactly. A course to teach people how to make money selling ebooks.

The Path: Affiliate Marketer>>Write books about stuff Scott learned as an affiliate marketer>>Children’s books (?)>>Write books about personal development>>Create course about writing and making money with books

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8. Alan: Failed Cop to Factory Worker to Factory Owner

Here’s another path with an old-school feel.

Alan grew up poor. He just wanted to make money to drive cars that could get girls.

He tried to be a cop but failed the test.

He didn’t know what else to do so he started working at a factory. Not a high-tech factory, one with century-old equipment.

He worked there for a couple decades.

Decades. That’s a long, long time.

He learned the whole time he was there. Learned about the machines, the business, and the people. The owner grew to trust him.

Alan was able to take a small piece of ownership of the company.

After another few years, he owned it outright.

The Path: Failed Cop>>Factory worker for 20 years>>Fraction-owner of factory>>Owner of factory

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9. Forrest: Stupid Guy Goes From One Crazy Situation to the Next

Forrest grew up being ridiculed for being poor and stupid. The one girl he loves doesn’t love him back.

Forrest went into the Army where he meets Bubba, who convinces him to go into the shrimping business with him after the war.

Unfortunately, Bubba was killed and Forrest was taken on a whirl-wind of events. He met with JFK, Elvis, Lyndon Johnson, and Nixon. He made massive change wherever he went but was too stupid to realize it.

After many years Forrest stumbles on a shrimping boat and learns the shrimping business. It’s not long before he starts Bubba Gump Shrimp.

You can still eat at Bubba Gump Shrimp today.

The Path: Failed relationship>>Army>>Everywhere>>Make History>>Start Bubba Gump Shrimp

😉

(That’s the only fake one, I promise!)

10. Ryan: College Writer>>Assistant to Bestseller>>Marketer>>Bestselling Author-Entrepreneur

While in college Ryan wrote a bestselling author a letter—this magical letter got him a job working for the bestseller. He takes time off college to seize the opportunity (but keeps the option to go back).

Ryan is an avid reader and takes extremely detailed notes about what he reads. He approaches another bestselling author and becomes his research assistant (and consequently his mentee).

Ryan has learned an amazing amount about writing and marketing from his independent studies.

In his late 20’s he becomes the marketing director at a major brand. During this time he also markets multiple bestselling books.

He decides he wants to become an author and so he writes about how he pulled off his marketing stunts.

People love it, he’s everywhere. A year later he launches another book.

He decides to start saying “no” to money. He wants to come out of hyperdrive.

The Path: College-writer>>Writer’s assistant>>Other writer’s researcher, assistant, mentee>>Marketing director>>best-seller going hardcore>>chilling while best-selling

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11. Elliott: Trainer to YouTube Personality to Internet Marketer

Elliott was always obsessed with strength—physical, mental, spiritual. He became a physical trainer to help build strength in people starting with their bodies.

It was tough at first, people didn’t know what to make of his teaching.

He kept going though. He kept reading about all the types of strength and becoming a better trainer.

He wrote a book but only a few people bought it.

A friend told him he should market it online.

“How?”

“You’ll kill it with videos.”

So he started making videos.

A year went by with him posting once a week and nothing happened.

He decided the answer was to make more videos. He released 5 videos a week, Monday through Friday.

He got some results. Then he decided to go even harder. 14 videos a week, 2 a day.

Elliott immediately saw an increase in views and ebook sales. He also saw huge improvement in his performances on videos.

Today he has nearly a million people subscribed to his YouTube channel. Every event or class he gives is sold out immediately.

The Path: Trainer>>Write a book>>Go to YouTube (Fail)>>Do YouTube Right

12. PewDiePie: Play Games to YouTube Lame to YouTube Famous

This is nearly the same as the above path except for one thing: Pew isn’t trying to sell anything. He’s just trying to entertain.

Like many guys in their teens, Pew was obsessed with video games. His parents didn’t tell him to stop playing… so he didn’t. And he got really freaking good.

So good that he could win while constantly cracking jokes about what’s going onscreen.

Apparently Pew got sick of talking to himself one day so he started recording himself playing the games.

People loved it and he became the most-watched guy on YouTube.

The Path: Get really good at something>>Be able to express your personality>>Record yourself and put it on YouTube

(This path has been followed by a ton of different people. There are girls making a killing doing makeup tutorials or talking about Pop Culture. FreddyW began uploading special effects videos he made with friends and now has millions of subscribers.)

13. Paul: Computer Science Degree to Art School to Artist to Entrepreneur to Venture Capitalist

Paul got a computer science degree and then decided to study art in Europe.

He struggled to make it as an artist, doing odd jobs to pay for paint.

He was putting canvas on a frame on day in New York when he heard about some financial guy making millions and millions of dollars. He heard the guy speak and thought, “I’m smarter than this guy, I can make money.”

And so he dropped the canvas and set out to try and start a startup.

He did.

There were a few failed attempts. Bad ideas executed poorly.

Paul was sleeping on a mattress in a small room, along with the two other cofounders. They needed make the thing work.

And they did.

After a few more years of ups and downs Paul was able to sell out and walk away with about $100,000,000. He made the money he set out to.

He then began writing about his experiences. Teaching others from the lessons he learned. His essays began to get extremely popular online. Then he gave a speech to college kids about startups. Their reaction was incredible. More than he ever expected.

He created a new kind of venture capital firm that helped small companies prove their validity and raise more money.

The fund’s companies now have a valuation of over $30 billion.

The Path: Learn Programming>>Study art>>Try art>>Get poor>>Use programming knowledge to work on a startup

hip-hop-funny

14. Jay: Ghetto to Artist to Businessman

Jay grew up in the ghetto. He rapped and rapped and finally got famous for it.

Once he got a lot of attention he was able to make a lot of money for rapping. He was a successful artist.

With his money and the connections he gained from being in the music industry Jay was able to start his own record label.

The Path: Rap for nobody>>Rap for a few people>>Get paid to rap>>Pay people to rap

15. Logan: Job to Startup to Job to Startup

Logan has spent the last fifteen years with entrepreneurial ventures that have, for most of the time, turned out just well enough for him not to have to get a job.

He’s started blogs, bought and sold domains, created marketplaces, all sorts of stuff.

Logan would push a new project forward. Something was missing, something wasn’t clicking.

For the first time ever he’s begun to create real, consistent wealth.

He joined our importing program less than six months ago and is making well over $40,000 each month. The coaching and community support helped break down whatever barriers were holding him back.

The Path: Job>>Miscellaneous Internet Projects>>Job>>More Miscellaneous Internet Projects>>Job>>Importing Course>>Importing Business

16. Cindy: Trainer to Law School to Politician to Personality to Entrepreneur

Cindy dropped out of high school and started working.

She built a political career that most people would be happy ending up with. Then she got bored and went to the ARMY. Then went to Law School, got a crazy job offer and turned it down to home school her kids instead.

Yeah, somewhere in there she had kids. And was a fitness trainer.

Then her kid went to school

She had energy and dreams.

She wanted to start a business. She had an idea but didn’t know the first step to take.

Cindy messaged me on Facebook “Will you coach me?”

“Okay.”

We changed her business model to leverage her strengths, we got rid of the blocks she’d been having, and we put a system in place. Now Cindy’s business is up and running and soon she’s going to be the Queen of all things wellness.

(Oh, by the way, she’s now teaching what she taught as a trainer—just on a bigger scale.)

The Path: High School Dropout>>Entire Political Career>>ARMY>>Law School>>Unschooling mom>>Wellness Business Owner

sara-forbes

17. Sara: Communication Degree to Law School Reject to Disney Park Worker to Fax Saleswoman to Hosiery Inventor to One of the World’s Richest Women

Sara graduated from FSU with a Communications degree. Have you ever heard someone talk about that degree being useful?

She wanted to go to Law school but couldn’t perform. She ended up getting some crappy job at Disney and doing standup on the side. No good.

She began selling fax machines and kicked ass. By the time she was 25 she was training other people to sell fax machines.

When she was 27 she invented some new hosiery. She invested a bunch of time and $5,000 of her savings in researching and prototyping the things.

She kept on keeping on. Slowly perfecting her product and brand. Bringing it in front of more and more people. Slowly gaining the support she needed to make the thing work.

Now she’s worth a billion dollars.

The Path: Law School Rejection>>Disney job>>Standup Comedy>>Saleswoman>>Inventor>>Drudgery>>Tenacity>>Billionaire

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18. Usef: Somewhere to Somewhere to Here to There to There

Usef wasn’t in an ideal situation.

There was confusion in society about how to make a living and what it meant to live well.

The economy was going through the biggest shift since the Great Depression and Usef was caught in it.

Usef wanted to know which path to follow, which way would work.

Usef got educated about the new economy, applied the education, and ended up in a totally unimagined place.

The Path: Wherever you’ve been>>Here>>Learning>>Trying>>Failing>>Trying>>Failing>>This thing>>That thing>>Winning(>>Failing>>Winning…)

Your path is going to be your own whether you try to “blaze” it or not. There’s no telling where your life will lead but you can certainly aim it. What works? You can’t know until you test it. These are crazy times and it’s up to you to not become crazy with them.

Wrapping This Up...

What do you think?

What paths are interesting to you?

Did you figure out any of the paths?

Let me know below!

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Author

Avatar for Kyle Eschenroeder
Kyle Eschenroeder

Thanks for taking the time to read this! Let me know what you think - the good, the bad, the ugly - in the comments below.

I'm an entrepreneur (more in the StartupBros About Page) in St. Petersburg, FL

  • Avatar for Todd Jensen Todd Jensen says:

    This is the most encouraging article I’ve ever read. There’s a message in here that many people desperately need (even people who don’t think of themselves as entrepreneurs or future entrepreneurs): that we may be right on track, even if it feels like we’re floundering. And instead of only offering a fleeting hit of inspiration and optimism, you tell that story in a way that sinks in, because it rings so true.

    I hope you keep writing, Kyle. Thank you for sharing it.

  • Avatar for Jeff Jeff says:

    This is got to be one of the funniest/motivational posts I’ve recently read

  • Avatar for Mae Mae says:

    Love the article and would like to share it with our trainees, though I feel it doesn’t showcase sufficient female stories to do so.