The Road Less Traveled: A Strategy for Business And Life

I was attending a finance careers talk at the London Business School a few months ago. The speaker asked a cohort of students to scan the QR code on the screen to complete a survey. The attendees were asked to type in the name of their dream employer.

As the responses came in, the text size of the most frequently selected responses grew larger and larger. Two minutes later, the screen was filled with just a few names. Blackstone, Goldman Sachs, and JP Morgan took up most of the screen.

This reinforced my belief that applying to these companies was not the way to go. Unless you want average results, doing what everyone else does is probably not the best strategy.

A better strategy would be to apply to smaller and lesser-known companies that you can grow with. You can take on more responsibility and make more of an impact at smaller firms. Depending on what you want out of life, it's a better strategy than being a small cog in a large system.

I also thought about how many of the most successful finance leaders took unconventional paths to get to the top. The current and former CEOs of Goldman Sachs and many leaders of the large banks didn’t start off in those banks.

Jamie Dimon’s unconventional career:

Jamie Dimon, the CEO of JP Morgan, built the company into the prestigious (and arguably most successful) financial institution it is today. After completing his MBA at Harvard, he rejected offers to work at Goldman Sachs and Morgan Stanley. Instead, he went to work for Sandy Weill at American Express - as his assistant. Weill was an entrepreneur who had sold the securities brokerage firm he helped build to American Express for $950 million. Dimon wanted to learn from him.

Most graduates of top business schools would not take the opportunity to become an assistant after two years at an elite school. But Dimon's priority was experience and opportunity, not status. Two years later, in 1985, Weill left American Express, and Dimon followed suit.

Weill wanted to build another financial service company. He purchased a troubled consumer finance company called Commercial Credit for $7 million. At 30, Dimon found himself the CFO of Commercial Credit. Dimon was good at what he did, so much so that his business approach was described as ‘surgical.' Weill was the strategist and dealmaker while Dimon would focus on day-to-day operations.

Through a series of transactions and turnarounds that involved various financial institutions, Weill and Dimon created Citigroup. At the time, Citigroup was the largest financial services firm in the world.

The creation of Citigroup was groundbreaking in the world of finance. Citigroup was the first company that offered a full range of financial services, from commercial banking and insurance to brokerage services and asset management. Sandy Weill had finally fulfilled his mission of building a ‘financial supermarket.’

It wasn’t long after the formation of Citigroup that Weill asked Dimon to resign. The pair had gotten into disputes about succession, and Dimon had to leave.

Dimon was out of work for a period of time. Jeff Bezos reportedly offered him a job at Amazon during that time. In March of 2000, Dimon was appointed as the CEO of Bank One, a struggling bank based in Chicago. Dimon successfully turned Bank One around in just a few years and orchestrated its acquisition by JP Morgan. Since then, Dimon has grown JP Morgan into one of the most successful banks in the world.

Tim Cook’s leap of faith:

In a recent interview with the Wall Street Journal, Tim Cook recounted his experience in making the decision to work for Apple in 1998. Before moving to Apple, Cook worked for Compaq. Compaq was the leading personal computer maker at that time with a ~20% market share.

Meanwhile, Apple was struggling and had a roughly 2% market share. Steve Jobs was asked to join as Apple’s CEO a year earlier to turn things around. Cook’s instinct was to not follow the crowd, so he joined Apple.

Their success formula: Entrepreneurs and their uncommon journeys

The most interesting stories are, by definition, unconventional. Here are a few unconventional experiences of well-known people, in the form of an equation.

✨ Steve Jobs (Apple): College drop-out + calligraphy class + Atari job + trip to India + HP internship + assembling and selling computers -> Co-founded Apple

👟 Phil Knight (Nike): Student athlete (runner) + accountant + Stanford MBA + import/export of Japanese shoes -> Founded Nike

💼 Sara Blakely (Spanx): Door-to-door fax machine saleswoman + DIY clothing experiments + $5,000 savings -> Founded billion-dollar brand Spanx

🎬 Dwayne "The Rock" Johnson: College football player + unsuccessful Canadian Football League stint + pro wrestling star -> Hollywood's highest-paid actor

📺 Reed Hastings (Netflix): Math teacher in Swaziland (Peace Corps) + failed software startup + sale of Pure Software -> Co-founded and transformed Netflix into a streaming giant

💸 Peter Thiel (PayPal & Founders Fund): Stanford law degree + securities lawyer + tech startup founder -> Co-founded PayPal and Palantir, became influential VC at Founders Fund

📚 Ben Horowitz (Andreessen Horowitz): English literature major + failed job as technical support rep + co-founded Opsware -> Became co-founder of top VC firm Andreessen Horowitz

🏠 Brian Chesky (Airbnb): Design degree + struggling artist + air mattresses rented to conference attendees -> Co-founded Airbnb

🌐 Sheryl Sandberg: Harvard Business School + U.S. Treasury Department + VP at Google -> COO of Facebook (now Meta)

The Most Interesting Man In The World:

You’ve probably seen images of the "Most Interesting Man in the World" from the Dos Equis commercials. It was frequently used as a meme back in the 9gag days.

In the commercials, the character is depicted through flashbacks showing some of his extraordinary feats. He’s seen arm-wrestling in a remote bar, jumping off cliffs, climbing mountains, or freeing a trapped animal in the wild.

His memorable adventures and outgoing personality make him a likable person. Viewers wanted to emulate his sense of thrill and fearlessness. He was an aspirational figure for audiences.

The campaign was highly successful because it tapped into a universal desire to lead a life full of excitement and curiosity. He encouraged people to embrace adventure with his famous tagline: “Stay thirsty, my friends.”

The Most Interesting Man In The World was inspired by the unconventional lives of Ernest Hemingway and Sir Richard Burton—two legendary figures who embraced adventure and became symbols of bold living.

Hemingway, known for his courageous spirit, lived a life full of high-stakes adventures. He was a war correspondent, an avid hunter, and a deep-sea fisherman, drawing on his extraordinary experiences to infuse his writing with authenticity and grit.

Sir Richard Burton, a 19th-century explorer and linguist, immersed himself in diverse cultures and ventured off to unknown regions of Africa.

Both men took paths that broke with convention, making their lives unforgettable.

Choosing the unconventional and adventurous path can be rewarding in many ways.

It stops complacency and instills in people an enjoyment and appreciation of life.

Choose the unconventional path, take on more responsibility, and go on an adventure.

It won’t be easy to take the leap of faith, but you have to trust that it will be rewarding.

It opens the realms of possibilities.

Take the path less traveled.