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5 Seriously Successful Entrepreneurs with Surprising Starts (And Why They’ll Go Down in History)

It’s not necessarily a grand gesture or overnight success that skyrockets business icons to the top.

It’s often the small things – the gut choices we make every day – that influence the course of our own history.

In some cases, success springs from a mix of hard work, dumb luck, and more perseverance than many can imagine.

Uber, McDonald’s, Starbucks, Apple, and Amazon are among the biggest, most valuable brands in the world.

Today, these businesses are massively successful – but they were started by entrepreneurs who worked their way up from the bottom. In fact, you might be surprised by the events and circumstances that led to their success.

Often the most meaningful business stories – the ones that become the stuff of legends – are those that inspire us to pursue our own ambitions. So, let’s dive into the surprising origin stories behind these five industry giants that do just that.

5 Entrepreneurs Who Will Go Down in Sales History – and How They Got Their Start

1. Uber Co-Founder Travis Kalanick: He Used Old-Fashioned Cold Calling to Fuel a Tech Empire

Uber Co-Founder Travis Kalanick

The newest business on our list today, Uber’s short history is peppered with controversy. From complaints about its workplace culture to a nasty legal battle with investors, Uber’s emergence on the tech scene has certainly made waves.

Though co-founder Travis Kalanick recently stepped down as CEO, he’ll be remembered for disrupting the traditional taxi industry and building one of the most influential, notorious tech companies in the world.

So, how did Kalanick get his start? What were his original plans for Uber? How did he get this controversial business up, running, and dominating the industry?

You might assume that such an innovative tech giant relied on forward-thinking growth hacks to power its success – but that’s not the case at all.

One of Kalanick’s first moves to get Uber up and running was good old-fashioned cold calling.

As Kalanick puts it: “I went to Google, typed in San Francisco chauffeur or San Francisco limousine, I just filled out an excel sheet and I just started dialing for dollars, right?

“The first ten guys I called, three of them hung up before I got a few words out, a few of them would listen for like 45 seconds and then hung up, and three of them said ‘I’m interested, let’s meet. And if you’re cold calling and three out of ten say ‘let’s meet’, you’ve got something.”

Kalanick went from cold calling limousine drivers to growing Uber into an empire valued at $68 billion.

What can we learn from this? Cold calling is alive and well!

Not only is cold calling (or cold emailing) a tried and true method of getting through to your customers, investors, or users, but it’s also key to validating your concept.

Can you get your target customer or investors on the phone? Are they willing to listen to you? Do people like what you have to say – or do they brush your idea off as a pipedream?

2. Ray Kroc, Who Opened the First McDonald’s Franchise After a 34-Year Career in Sales

ray croc mcdonalds

For anyone who’s ever felt it was too late to chase a new dream or start a business, Ray Kroc is proof that anything is possible and there are no expiry dates on success.

Kroc got his start selling paper cups and milkshake machines. He spent 34 long years as a salesman and didn’t open his first McDonald’s franchise until he was 52 years old. When Kroc passed away in 1984, his fortune had grown to $500 million.

In his own words, Kroc “was an overnight success alright, but 30 years is a long, long night.”

It’s hard to imagine the modern day fast-food landscape without those iconic golden arches, but Kroc stumbled up McDonald’s while selling Mutimixers to fast food retailers. Each of his Multimixers could churn five milkshakes at once, so when Dick and Mac McDonald purchased eight of his machines for their small California burger chain, Kroc was compelled to find out what kind of operation they were running that they needed to mix forty milkshakes at once.

Clearly, he was impressed with what he saw.

Despite opposition from his friends and family, Kroc opened the doors of his first McDonald’s franchise on April 15, 1955 and sold $366.12 of burgers, French fries, and triple-thick shakes.

Kroc went on to buy the business from the McDonald brothers in 1961, putting his entire life savings on the line to do so.

Within ten years opening his first McDonald’s franchise, Kroc was at the helm of a growing empire there were more than 700 locations across the country.

Kroc has basically lived out an entire career in sales before he took a risk on McDonald’s. Today, his legacy is the world’s largest burger chain, serving 68 million customers daily.

The takeaway? It’s never too late to achieve your dreams – if you’re bold enough to believe in yourself.

Kroc said himself, “I guess to be an entrepreneur you have to have a large ego, enormous pride, and an ability to inspire others to follow your lead.”

3. Starbucks’ Howard Schultz: From Rags to Riches to International Coffee Mogul

Starbucks’ Howard Schultz

It’s important to remember that success is rarely linear. Sometimes we need to take a small step back to gain a new perspective before we can realize our potential.

Howard Schultz is famous for growing Starbucks from a local Seattle coffee chain to an international addiction. However, he took a huge step back from the Seattle coffee shop before he was able to bring his vision to life.

Here’s how his story played out:

Growing up in poverty instilled Schultz with a drive to attain financial security. He started off in sales at Xerox before moving on to a Swedish company that supplied equipment to companies like Starbucks.

The Seattle coffee shop caught his eye by placing an unusually large order of drip coffeemakers. That’s when Schultz decided to pay the owners, Gerald Baldwin and Gordon Bowker, a visit. He was immediately impressed by their passion for coffee and dedication to selling a high-quality, niche product.

In fact, Schultz was so enthralled with Starbucks that he spent the next year persuading Baldwin to hire him as the director of retail operations and marketing.

On a business trip to Milan, Schultz was exposed to Italian coffee culture, which was unlike anything he’d ever seen stateside. The espresso bars of Milan served cappuccinos, knew customers by name, and showed Schultz that coffee could offer a much more personal experience.

When he returned home, Schultz was bursting with new ideas for Starbucks – none of which Baldwin and Bowker were interested in trying. So, rather than ignoring his gut to appease his bosses, Schultz left Starbucks behind to open his own Italian coffee shop.

Before he was able to get his shop, Il Giornale (“the daily” in Italian), off the ground, Schultz needed to get his hands on $1.6 million in funding. He was turned down by 217 investors, but persevered to secure the funds he needed.

“In the course of the year I spent trying to raise money, I spoke to 242 people, and 217 of them said “no,” Schultz wrote in his book, Pour Your Heart Into It. “Try to imagine how disheartening it can be to hear that many times why your idea is not worth investing in.”

In August 1987, about two years after leaving Starbucks to focus on Il Giornale, Schultz purchased Starbucks for $3.8 million. He became the CEO of Starbucks Corporation and grew it from six stores to over 1600 stores worldwide.

4. Steve Jobs Learned the Power of Ideas Selling “Blue Boxes” Illegally in the 1970s

Steve Jobs Apple

Years before co-founding Apple, Steve Jobs’ first business was building and selling illegal telephone-hacking “blue boxes” in the 1970s. The boxes mimicked certain tones that were used to make long-distance phone calls, allowing people to make free calls around the world.

As teenagers, Jobs and his friend (and eventual Apple co-founder) Steve Wozniak were fascinated with blue boxes and decided to learn how to build one themselves. They designed and built the world’s first digital blue box and gave them to friends and family.

Though the pair gave up their venture when they were almost caught by the police, they earned around $6000 selling their blue boxes. Wozniak also claims he tried to prank call the Pope by pretending to be Henry Kissinger, though the Pontiff was sleeping at the time.

Jobs said the magic of it was that “two teenagers could build this box for $100-worth of parts and control hundreds of billions of dollars of infrastructure in the entire telephone network in the whole world from Los Altos and Cupertino, California. That was magical.

“Experiences like that taught us the power of ideas. The power of understanding that if you could build this box, you could control hundreds of millions of dollars around the world and that’s a powerful thing. If we hadn’t have made blue boxes, there would have been no Apple.”

Not only did their success with the blue boxes teach Jobs and Wozniak how to work well together, but it also gave them confidence in their ability to design and build technical solutions.

5. Amazon Founder Jeffrey Bezos Left a Cushy Corporate Job to Sell Books Out of His Garage

Amazon Founder Jeffrey Bezos

Jeffrey Bezos was inspired to start Amazon during the internet revolution of the 1990s, when he realized the huge potential of selling goods online.

At the time, Bezos was the youngest-ever VP at D.E. Shaw & Co., but his entrepreneurial drive wasn’t satisfied with life on Wall Street. The more he learned about the internet, the more he dreamed of building his own web-based company. So, he quit his lucrative job and went all in on bringing his vision to life.

“The wakeup call was finding this startling statistic that web usage in the spring of 1994 was growing at 2,300 percent a year,” Bezos explained. “You know, things just don’t grow that fast. It’s highly unusual, and that started me about thinking, “What kind of business plan might make sense in the context of that growth?”

Next, he came up with a list of twenty potential items he could sell online. Once he decided books were the ideal product (due to the sheer volume of titles available and the limited shelf space of physical retailers), Bezos started his business out of his garage.

For almost a year, Bezos and a team of five created the systems that would make Amazon.com simple to navigate. They also learned how to source books and developed tools that would allow the site to function as a “virtual community,” like the recommendations feature that suggests titles based on a customer’s purchase history.

In 1995, Amazon.com launched with over one million books for sale and the punchy tagline “Earth’s Biggest Bookstore.”

Within the first month, Bezos was doing $20,000 in sales per week and raised $8 million in funding by the end of the year.

Fast-forward to 2017, and Amazon is the largest online retailer in the world, generating over $61 billion in annual revenue.

Amazon has since acquired over 44 companies, including Zappos and the Washington Post, and currently employs 97,000 people.

“We are stubborn on vision. We are flexible on details…we don’t give up on things easily. Our third-party seller business is an example of that. It took us three tries to get the third-party seller business to work. We didn’t give up.

If you’re not stubborn, you’ll give up on experiments too soon. And if you’re not flexible, you’ll pound your head against the wall and you won’t see a different solution to a problem you’re trying to solve.” -Jeff Bezos

What Mark Will Your Business Make on the World?

Each of these companies (and their founders) will go down in history as icons of success, and the inspiring, perplexing, and unusual origin stories behind them lend further credence to their status as legends.

When the going gets tough and you feel like you aren’t making progress, it can help to reflect on these tales of famous entrepreneurs who faced the odds, overcame adversity, and made a lasting mark on their respective industries.

Free Download: The Beginner’s Playbook to Running a Cold Email Campaign

If you want to elevate your own success story to the stuff of legends, you’ve got to start with the basics. After all, everyone starts somewhere – and this could be where you can start launching more effective cold email campaigns.

Want to learn how to craft the right subject line, message, offer, and follow up sequence for your email campaign? This free guide will show you how!

Download The Beginner’s Playbook to Running a Cold Email Campaign

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