• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

eBay will pay nearly $50 million after employees reportedly sent a Massachusetts couple a bloody pig mask, cockroaches and death threats

2

Current price of oil as of July 28, 2026

3

The millennial generation is split in 2: an older crowd with boomer-style comfort, a younger set going 'back to the early 1900s'

1

eBay will pay nearly $50 million after employees reportedly sent a Massachusetts couple a bloody pig mask, cockroaches and death threats

2

Current price of oil as of July 28, 2026

3

The millennial generation is split in 2: an older crowd with boomer-style comfort, a younger set going 'back to the early 1900s'
Tim Cook

Why Risk-Takers Make the Big Bucks

By
Steve Tobak
Steve Tobak
and
Entrepreneur
Entrepreneur
Down Arrow Button Icon
By
Steve Tobak
Steve Tobak
and
Entrepreneur
Entrepreneur
Down Arrow Button Icon
February 27, 2016, 3:00 AM ET
Apple Unveils New Versions Of iPhone 6, Apple TV
SAN FRANCISCO, CA - SEPTEMBER 9: Apple CEO Tim Cook stands on stage during a Special Event at Bill Graham Civic Auditorium September 9, 2015 in San Francisco, California. Apple Inc. unveiled latest iterations of its smart phone, forecasted to be the 6S and 6S Plus and announced an update to its Apple TV set-top box. (Photo by Stephen Lam/ Getty Images)Photograph by Stephen Lam — Getty Images
Add Fortune on Google for similar content.

This piece was originally published on Entrepreneur.

What’s more exciting, a cross-country skier trudging across the terrain or a downhill racer risking life and limb at 90 miles per hour? Of course it’s the latter, and that’s why we watch.

Even in professional sports like tennis where physical injuries rarely occur, it takes guts to compete with millions watching and everything on the line, not to mention the drama of two athletes competing head to head to win.

No risk, no reward. It’s the same in business. And let me tell you something, folks. Just because you call yourself an entrepreneur, doesn’t make you a bigger risk-taker than a company employee.

Take the CEO of a public company, for example. It was just as risky for Tim Cook to get up on stage and bet big on the Apple Watch as it was for Steve Jobs to go up against Big Blue with Apple’s groundbreaking “1984” Super Bowl ad 30 years earlier.

That was not the first time Cook took a flying leap. In 1994, he gave up a 12-year career at IBM to become an executive at computer distributor Intelligent Electronics. When the company unraveled, he joined Compaq, the world’s largest PC maker, but left after just six months to help Jobs turn around struggling Apple.

In 2013, Cook decided to risk a third of his compensation on Apple’s performance versus the rest of the S&P 500 over an eight-year period. Make no mistake, there’s no upside and no small print. He simply chose to lead by example and forfeit what amounts to more than $100 million if the company under performs.

The following year, Cook, who grew up in a working class family in the south, became the first Fortune 500 CEO to publicly come out as gay. The man has guts, I can tell you that. That willingness to put his own butt on the line and hold himself accountable is why he now runs the most valuable technology company on Earth.

There are very few Tim Cook’s in the world; far fewer than you probably realize.

The vast majority of people follow the path of least resistance and lowest risk. That’s precisely why so few take big chances, accomplish great things and make the big bucks. That’s as true today as it ever was, but you’d never know it from the way we represent ourselves online.

If you believe our profiles, we’re all entrepreneurs, leaders, CEOs, investors, best-selling authors, award-winning speakers, experts, gurus — the absolute greatest thing since Bill Johnson shocked the world by becoming the first American male to win a gold medal in alpine skiing at the 1984 Winter Olympics.

But here’s the thing. You don’t get to decide how successful you are. The market alone makes that determination. No matter what label you decide to bestow upon yourself, until you take some serious risks and the market decides you’re as valuable as you think you are, you haven’t proven a thing and the rewards won’t follow.

I know a lot of you think of yourselves as entrepreneurs when, in reality, you’re just self-employed or solopreneurs, as it were. Not only is that not the same thing, it’s not even in the same ballpark. And if you dream of making it big someday, or at least becoming financially secure, I’m afraid you’re in for a rude awakening and I’ll tell you why.

You’re simply not putting enough on the line to expect that kind of return.

You could argue that opting to go it alone instead of working a full-time job is taking a risk, and maybe that’s true. But I suspect it’s just as likely that you’ve chosen a lifestyle with the perceived benefits of being your own boss, ruling your own destiny and having the flexibility to do what you want, when you want.

If that’s the case, you’ve actually chosen the past of least resistance and, in practical terms, that’s more or less the same thing as low risk. That’s all well and good, but I wouldn’t expect anyone to throw you a parade and bestow riches upon you. The tradeoff between risk and reward is very clear about that.

Look at it this way. The day you call yourself an entrepreneur, a leader, a CEO, an expert, whatever, is the day you give yourself a label, and that’s all it is. It’s the day you call yourself a downhill racer before putting on your first pair of skis.

Cook may never have founded a company, but that doesn’t make him any less of a risk-taker than those who do. Even though you work for someone else, if you put yourself out there, take big chances, and hold yourself accountable to be the best at what you do, the risk-reward tradeoff will go your way.

More from Entrepreneur:

Bill Gates Says Apple Should Cooperate With the FBI

Apple’s Tim Cook on Leadership: ‘The Most Important Data Points Are People’

5 Things You Don’t Know About Apple CEO Tim Cook

The irony is, a lot of people who work for others are far bigger risk-takers than those who think of themselves as entrepreneurs. And they’re also far more likely to reap the rewards.

About the Authors
By Steve Tobak
See full bioRight Arrow Button Icon
By Entrepreneur
See full bioRight Arrow Button Icon
Add Fortune on Google for similar content.

Latest in

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • TikTok icon
  • YouTube icon

Latest in

Eddie Smith Jr driving a boat
SuccessWealth
He worked 100-hour weeks to save a nearly bankrupt boat company. At 83, he’s just turned down $400 million for it—and gave it all to charity instead
By Preston ForeJuly 29, 2026
2 hours ago
Two female founders want to prove the best successor is another founder
NewslettersMPW Daily
Two female founders want to prove the best successor is another founder
By Emma HinchliffeJuly 29, 2026
2 hours ago
Bernard Arnault, CEO of LVMH
SuccessPersonal Finance
LVMH CEO Bernard Arnault reveals he owned nearly 20% of Netflix, but cashed out too early—his stake could be worth up to $60 billion today
By Emma BurleighJuly 29, 2026
2 hours ago
Millionaires are leaving the U.K. in droves thanks to tax hikes—but the CEO of $1 billion tax platform says it’s their ‘social responsibility’ to stay
SuccessWealth
Millionaires are leaving the U.K. in droves thanks to tax hikes—but the CEO of $1 billion tax platform says it’s their ‘social responsibility’ to stay
By Orianna Rosa RoyleJuly 29, 2026
3 hours ago
Costco’s $14 million email settlement: Who qualifies for an up-to $500 payment and how to claim before the Aug. 24 deadline
RetailCostco
Costco’s $14 million email settlement: Who qualifies for an up-to $500 payment and how to claim before the Aug. 24 deadline
By Sydney LakeJuly 29, 2026
4 hours ago
obama
PoliticsElections
Obama got ‘whooped’ by a Paralympian on the basketball court — now he wants Iowa to send him to the Senate
By Hannah Fingerhut and The Associated PressJuly 29, 2026
4 hours ago

Most Popular

eBay will pay nearly $50 million after employees reportedly sent a Massachusetts couple a bloody pig mask, cockroaches and death threats
Law
eBay will pay nearly $50 million after employees reportedly sent a Massachusetts couple a bloody pig mask, cockroaches and death threats
By The Associated Press and Leah WillinghamJuly 28, 2026
21 hours ago
Current price of oil as of July 28, 2026
Personal Finance
Current price of oil as of July 28, 2026
By Joseph HostetlerJuly 28, 2026
1 day ago
The millennial generation is split in 2: an older crowd with boomer-style comfort, a younger set going 'back to the early 1900s'
Real Estate
The millennial generation is split in 2: an older crowd with boomer-style comfort, a younger set going 'back to the early 1900s'
By Nick LichtenbergJuly 25, 2026
4 days ago
Jamie Dimon says his stockbroker father taught him to invest with a 'brutally hard' childhood game
C-Suite
Jamie Dimon says his stockbroker father taught him to invest with a 'brutally hard' childhood game
By Sarah GlodekJuly 29, 2026
11 hours ago
Why did a $154 billion CEO just endorse stripping most Americans of voting rights—and taking us back to the 19th century?
C-Suite
Why did a $154 billion CEO just endorse stripping most Americans of voting rights—and taking us back to the 19th century?
By Nick LichtenbergJuly 27, 2026
2 days ago
The brutal math behind Gen Z's lonely weekends: $15 drinks are driving a generational 'spending hangover'
Economy
The brutal math behind Gen Z's lonely weekends: $15 drinks are driving a generational 'spending hangover'
By Nick LichtenbergJuly 28, 2026
1 day ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.