The Dream

Reading Gurbaksh Chahal’s The Dream nearly left me in an existential panic.  At the age of twenty-nine, he’s done almost everything.  He’s dropped out of school (age 16), started his first company (17), sold it for $40 million (18), started his second company (22), sold it for $300 million to Yahoo! (25), published an autobiography (26), appeared on The Oprah Winfrey Show (26), started his third company (27), received an honorary university degree (28) and shaken hands with President Barack Obama (29).

He’s not even thirty.

The Dream chronicles Gurbaksh Chahal’s meteoric rise from the gang-ridden streets of San Jose to becoming one of the world’s youngest and most successful billionaire-entrepreneurs.  It’s a brilliant book, but it isn’t for everyone.  This book hasn’t been written for people who merely want to succeed.  This is a book is for people who want to win; to get to the top and stay there.

The Big Idea

The Big Idea: The biggest takeaway from the book

Identify Your Goal and Focus On It Like A Hawk

"You will have bad days. There will be setbacks. You will have more than your fair share of failures. But at the end of the day, you pick yourself up and keep going. That’s the Big Secret of Life. You fall down, you get up… Fight like hell. Defy the odds… Some people think success is the best revenge, and they may be right, but for me it’s much simpler than that: Success is its own reward."
- The Dream, page 252

There it is.  That’s what the book breaks down into.  Need it even shorter? Here you go:

  • Find a way to make a living doing what you enjoy – no, what you’re passionate about
  • Force yourself to get through the bad days for the chance to enjoy the good ones
  • Fight to win and keep fighting until you get to the top – but retain your moral perspective
  • Keep fighting to stay at the top, because others will keep trying to pull you down

Gurbaksh enjoyed the thrill and excitement of the dotcom bubble of the late 90s.  He enjoyed studying companies that started off penniless, grew quickly without making any money at all and yet ended up being valued, bought and sold for several millions of dollars each.

He parlayed this interest into a passion in order to understand what made these companies – and their investors – tick, and figured out how he could leverage these findings to his own advantage.

Was it easy? No.

His father tried his hand at investing and got burned when the dotcom bubble burst.  The family had to suffer the humiliation of moving one step down on the economic ladder, but that was part of the challenge; yet another the obstacle to be overcome.

Gurbaksh soon identified online advertising as the death of traditional media, and realized that the online advertising industry was still a nascent enterprise, one that had yet to be consolidated by big players.  This represented an opportunity that was just waiting to be seized.

By doing his research, he found that he didn’t really need technical knowledge in order to operate on the web – he simply found others who could build his online advertising tools for him.  Partnerships were key, so he leveraged them judiciously and worked the scale and expanse of the web to pitch his business to potential customers over a period of several weeks, build up a reputation with a few clients at a time, and then focus on growth.

While he was busy making money hand over fist, “reality reared its ugly head” (page 78).  Turns out it wasn’t the crash of the dotcom bubble that he had to worry about – it was a shabby partnership.

Insight #1

An actionable way to implement the Big Idea into your life

Two Eyes Look Ahead, Three Eyes Look Behind

"Watch your back. Somebody should make a T-shirt that says: “For every back, there is a knife.”"
- The Dream, page 110

His business partner turned on him, called foul and played it equally well.  Now all of a sudden his business stopped operating, customers threatened deadlines and cash inflow dipped into the red.

The same thing happened later on in his career, too.  After selling his first company to a former competitor, his new business partners double-crossed him, filed a lawsuit and forced him to settle by attacking his reputation.

In the first instance he turned the tables on his erstwhile colleague.  Research told him that his partner was in poor standing with his business’s service providers.  By carefully positioning himself as a hero to his clients and surreptitiously undermining his rival’s standing with service providers, Gurbaksh pushed his partner into near financial ruin, removed him from the equation and soldiered on with business as usual.

In the second case, the challenge was the lawsuit itself.  “Any determined person can sue anyone over anything… Business people have to accept that as a reality of doing business. Still, it’s deeply troubling… At the end of the day, it seemed that the motivation behind this suit had one aim: to ruin my chance to get [my company] off the ground.” (page 178).

He had to settle – the lawsuit was causing the business to bleed cash and was destroying his reputation, which, of course was its intended purpose all along.

This was a lesson learned: always surround yourself with people who are at least as good as you are, who want you to succeed and who are not afraid of providing reality checks along the way.  Strength is the only natural safeguard for success, and strength can only be maintained through friendships, partnerships and personal growth.

Insight #2

An actionable way to implement the Big Idea into your life

Death From Above - Always Occupy the Higher Ground and Defend It

"Always negotiate from a position of strength. If you need something from the other guy, you’ve already lost. People want what they can’t have. Become the thing people want."
- The Dream, page 233

How do you move into a position of strength?

  • By making sure your business makes it a point to attract only the most talented and intelligent employees
  • By building and nurturing strong relationships with all of your stakeholders
  • By incorporating an intense focus on quality and execution into your business’s DNA
  • By always keeping an eye peeled on your competition

As the author puts it, “I didn’t reinvent the wheel. I simply found something that captured my imagination, and then I figured out how to do it better than the next guy” (page 235).

Make sure all of your efforts incorporate at least as many of the above recommendations as possible. The more you pursue, the more effective your efforts at creating value will be, and the faster your business appeal will rise.  Funnily enough, so will the price you command.


I loved The Dream because of the candor with which it was written. This is a no-holds-barred narrative infused with the confidence of a person who has nothing to lose from sharing his knowledge.

The sheer openness with which he shares his experiences and bares his deepest successes, failures, regrets and lessons is itself a lesson which reinforces the primacy of failure and criticism as the best of teachers.

Here’s a challenge:  when was the last time you excused yourself from doing something you wanted to do?  Write the excuse down.  Always carry a notebook with you and make sure to write down your thoughts every time you feel that you’re procrastinating or looking for a reason to avoid following-through with something.

Just write it down. Then, one day, just flip open the notebook and take a look at the litany of excuses that your mind has come up with to ensure you don’t do what you should have done a long time ago.

And before you pass out, make sure to pick up a copy of this book so you’ll wake up with it clenched in your hand.

Let’s go hunting.

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Prashanth Gopalan

ABOUT Prashanth Gopalan

A freelance blogger, writer and wordsmith based out of the twin-cities of Toronto and Waterloo, Prashanth uses his background in biotechnology, economics, marketing and communications to turn (some) wheels at Goose Educational Media...
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