Nothing to Lose, Everything to Gain

"From the outside it looks as if I have this great, easy lifestyle. The truth is I’ve never made a million dollars easily, and I’ve made many millions of dollars."

- Nothing to Lose, Everything to Gain, page 1-2

Some of the most astonishing successes in the business world have come to those whom the odds are stacked against. Ryan Blair, author of Nothing to Lose, Everything to Gain, is one such person. As a young boy, Ryan Blair reaped the benefits of a middle class lifestyle. His father had instilled within him “a risk-reward mentality” (10), and Blair displayed a considerable level of business acumen at a young age (exemplified best when he outsourced his chores to friends and kept the profit). But his life descended into a harrowing nightmare when his father became addicted to drugs. Ryan and his mother moved out of the family home into an economically depressed and unsafe area. Blair explains, “By the time I was seventeen I’d been arrested nearly ten times; I’d been asked to shoot a man to prove myself to the gang I was accepted in; I’d broken into and robbed every business within a mile radius from my house; I’d been dragged home in the middle of the night by police officers; I’d sold firearms with disastrous results; I’d gotten convicted for strong-arm robbery. Finally, after many of these episodes, I found myself sitting in a jail cell in Juvenile Hall, faced with four years. Every day I watched people leave the jail and wished I were among them.” (68) He vowed to be better: to get an education and a job. He was released early and did just that. By the time he was in his early 20s, Blair had made his first million with the sale of his first business venture. In his words, his success came from a mentality of “nothing to lose and everything to gain”.

The Big Idea

The Big Idea: The biggest takeaway from the book

Don't Let Anyone Steal Your Milk

"A lot of people come into my office with a front. They talk, and talk, and talk. And I test them."
- Nothing to Lose, Everything to Gain, page 23

Ryan Blair credits his street smarts and nothing-to-lose mindset as his “greatest assets”. In the book, Blair uses an analogy for his street smarts: stolen milk. When he was serving his imprisonment in Juvenile Hall at the age of 17, he quickly learned the rules of the game. New prisoners were subjected to a number of tests to determine whether they were “tough” or “domesticated” (i.e. willing to roll over and allow anyone take advantage of them). For example: “What would happen if I bumped into him? Or better yet, what would happen if I walked over and asked him for his milk during lunch? Was he going to jump up and fight? Or was he going to hand it to me and say he didn’t want it? … Soon you’ll be taking his milk every day. And so will everyone else.” (23-24) Blair has applied this psychology to the business world to considerable advantage. Many people build up a façade, and Blair uses the principles he learned in prison to discover the real person behind that mask to determine if that’s a person he’d like to work with.

“I start by asking for specific names, people they’ve worked with. Or I’ll ask a business-model question that only the real deal would know. You had millions in sales, huh? So what was your cost of goods sold? What type of EBITDA (Earnings Before Interest, Taxes, Depreciation, and Amortization) did you have? Where’d you bank? Wells Fargo? So were you with the private bank at Wells Fargo? Who’s your rep over there?” (23) Blair adds, “If the person can’t answer these types of questions in detail, he is either a complete scam, or he wasn’t actually responsibly for the success of the business he’s referencing.” (23) Asking this level of detail will help you in trusting your own instincts, as well, as you will see below.

Insight #1

An actionable way to implement the Big Idea into your life

Say No

"If you were to take only one thing I tell you and apply it to your business and your life, apply these words: if you say yes to too many seemingly good ideas, then you have one bad idea of a company and a poor management culture."
- Nothing to Lose, Everything to Gain, page 87

There’s this misconception that entrepreneurs and business managers have to be superheroes; that we have to juggle every seemingly viable venture that comes our way. Perhaps it’s because we see so many successful moguls who seem to have their hands in every pot, and think that that’s the key to fortune and success. Ryan Blair admits that he, too, has fallen prey to this trap. “I’ve learned this the hard way,” he says. “I tried to do too much and, well, I did too much. I didn’t focus on my company’s core competencies or the largest value creator on the list, and it cost me millions, in cash and in lost opportunities.” (87)

Doing something for the sake of doing it is a fast road to disaster and failure. You should only take on something new when it’s directly in line with your core objectives, or when it’s absolutely necessary to sustaining your business. You may feel uncomfortable in saying no the first time, so keep Blair’s words in the back of your mind when it proves difficult: “In my entire career I’ve never looked back and thought I should have said yes to something. In fact, it’s quite the opposite. My million-dollar mistakes… are rooted in not saying no often enough.”

Insight #2

An actionable way to implement the Big Idea into your life

The Path Is All Math

"Don’t get emotionally attached to projects. It’s math, not emotion."
- Nothing to Lose, Everything to Gain, page 86

Emblazoned above Ryan Blair’s desk are the words “The path is all math.” The mantra is quite simple. Rather than allowing your emotions to take over and make decisions for you, use math instead. For Blair it’s a maxim that has proved to be true time and time again. He offers an example to help illustrate his point.

When the call centre at ViSalus, his nutrition and weight-loss company, was experiencing delayed wait times (one of the cons to a quickly expanding business, and a customer service issue we’re all painfully aware of), the impulse to just hire more operators can be strong.  Instead, Blair advises hiring “someone to look at the data and study the analytics. When is the highest call volume occurring, and where is it coming from? Is there a way to survey the customers to find out why the majority call in the first place? Can their questions be answered via e-mail, online chat, or in some other way?” (86)

While this approach will take longer to implement, it’s the right business decision.  Not that that makes the decision any easier.  Just as learning to say no can be difficult, so can learning to avoid using your emotions in business situations.  As Blair reminds us, as entrepreneurs we are creative people, and learning to use math can be a challenge. But it can also mean the difference between growing a business and filing for bankruptcy.


As Ryan Blair says, “I’ve had the chance to ask world-champion athletes, billionaire businessmen, award-winning actors, and platinum record-selling musicians about how they achieved success; and what I have found time and time again is the same response: the journey to the top of your chosen field is filled with effort and sacrifice, self-teaching, and total commitment.”

This book is not merely inspirational; it also offers a lot of pragmatic advice – both from Blair, and his own personal heroes. Chapter 18, as an example contains sound advice on acquiring a lawyer, punctuated with Blair’s favourite quotes from such luminaries as Mark Twain, Sun Tzu, Jeff Bezos, Abraham Lincoln and Jay-Z, making it fun to read, too.  Nothing to Lose, Everything to Gain truly delivers on its promise to get you into that nothing-to-lose mindset, no matter where you’re starting from. You too will be able to think and make the kind of decisions that has made Ryan Blair both fearless and successful.

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Andy Budgell

ABOUT Andy Budgell

Andy is the Managing Editor at Actionable Books. A graduate of the University of Waterloo's English Rhetoric and Literature program, Andy brings a love of words to Actionable, and complements the team with his distinct writing ability, amazing customer service, and a passion for film.
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