Do You Really Know Bill Gates? The Myth of Entrepreneur as Risk-Taker

Photo: Laughing Squid/Scott Beale

Before I had to establish my no-blurb/no-review policy for books due to volume (picture: one day’s mail), I received an e-mail from Rick Smith, the founding CEO of the World 50, one of the most exclusive senior executive networking companies on the planet, with members and contributors like Bono, Francis Ford Coppola, and Phil Knight…

He was interested in having me look at his new book Leap, and I suggested he send it along with the understanding that I might not have the time to read it. To tell the truth, it took me a looong time to bother flipping it open, as the subtitle “How 3 Simple Changes Can Propel Your Career from Good to Great” is–in my opinion–devoid of sex appeal and misleading. It should be subtitled “How to Propel Your Life from Good to Great.” “Career” is not the right word at all.

I finished the book in two sittings.

Finally, here was a book that destroyed the myth of entrepreneur as risk taker, using case studies ranging from start-ups that became Fortune 100 companies, to Live Aid and the Girl Scouts.

One of the most frustrating types of resistance I encounter when talking about lifestyle design or entrepreneurship is a general response along the lines of: “That’s great for you, but I have kids and a mortgage. I’m not a risk-taker.”

The fact of the matter is, most of the uber-successful entrepreneurs I know hedge their bets and place small bets while keeping one foot on secure ground. This often includes testing the waters while employed full-time, as Rick himself did before creating World 50 from nothing. Most of them never gamble in real-life, and a decent percentage don’t invest in the public market (like me) because of the lack of control. Are there mavericks who lay it all on the table for the big win or cataclysmic loss? Sure. But don’t believe, just because the media likes to highlight such daredevils, that they are the majority of kick-ass founders. They aren’t.

Here is an excerpt from Leap that shows just how far off most perceptions of entrepreneurs are.

In this case, we start with Bill Gates.

Putting All the Chips on the Table?

Growing up as I did, with an early interest in business, it was almost impossible not to envy people like Gates, and even measure myself against them. Gates had placed all his chips on the table at one time and walked away richer than Croesus. And me? Well, I’d never even sat down at the table. The way I saw it, I couldn’t.

I graduated from a state university with a stack of loans to repay. No sooner had I begun to dig my way out of personal debt than I met my wife (who failed to bring her own shovel). I remember her father joking with me soon after we got engaged. “Son,” he said, “I want to let you know about Lori’s dowry—you get her student loans and her bad teeth!” He laughed from deep in his chest. I moaned from the same spot. Add to that three children born within five years, and I felt like I was slogging through quicksand.

If only I was in a different position, I used to think. If only I had the courage to take on more risk, like Bill Gates, like lots of others I used to list to myself. And then finally, years later, I realized that that’s not how it happened at all.

William Henry Gates III was born October 28, 1955, in Seattle, Washington, to a family with a rich history in business, politics, and community service. His great-grandfather had been a state legislator and mayor, his grandfather was the vice president of a national bank, and his father was a prominent and very wealthy lawyer.

Because young Bill excelled from his earliest school days, especially in science and math, his parents saw that he was enrolled in prestigious Lakeside Prep, known for its intense academic environment. This was in the late 1960s, when the world of computing was just beginning to peek over the horizon and carried a golden price tag. But no problem. To assure Lakeside’s students wouldn’t be left behind, the school held a fund-raiser and, with the proceeds, rented what it thought would be a year’s worth of time on a computer owned by General Electric.

Bill Gates, his close friend Paul Allen, and a few others torpedoed that plan in a big hurry. They started hanging out in the computer room day and night, learning everything they could, even to the detriment of their other academic obligations. Within a matter of weeks, the expected year’s worth of allotted computer time was gone, but that was no problem either. The school simply struck a new deal, this one with Seattle-based Computer Center Corporation, to get additional computer time at good rates.

That might have worked if young Gates and his friends hadn’t immediately started (a) hacking into CCC’s security system so they could reset the meter that tracked computer use and (b) crashing the system just for fun. They were caught, and the company banned Gates and his cohorts from its computers for several weeks. (The thought of Gates and Allen as the godfathers of a hacking subculture that has cost Microsoft and the world overall hundreds of billions of dollars does indeed boggle the mind.) But again, the exile was only temporary.

CCC’s business was beginning to suffer from the system’s weak security and the frequency with which it crashed—many of the same flaws Gates and his friends had been exploiting—so the company offered the gang a deal: find the bugs and pinpoint the weaknesses in the system, and they could have unlimited use of the computer.

In 1970, Computer Center Corporation ran into financial trouble that would eventually put it out of business, but by then, Gates and Allen had found a new computer home at the University of Washington, where Allen’s father worked. Lakeside also pitched in: during Gates’s junior year at the prep school, the administration offered him a job computerizing the scheduling system. Over the summer, Gates and Allen wrote the program, which coincidentally assured that Gates was assigned to classes with mostly girls—a sequence straight out of a nerd’s revenge movie.

In the fall of 1973, Gates left Seattle to begin his freshman year at Harvard, part of his preprogrammed life plan. Allen, who almost certainly could have been admitted to Harvard along with his pal, chose a different route. He wanted hands-on experience, but the two remained in close contact, often discussing the potential of one day starting a company, and at the end of Gates’s first year at Harvard, Allen moved closer to Boston so they could continue to pursue the still-vague possibilities. Then, in December of Gates’s sophomore year, the vague future began to take on a more exact face.

On a visit to Harvard, Allen stopped at a convenience store and noticed the current issue of Popular Electronics magazine. On the cover, under the title “World’s First Microcomputer Kit to Rival Commercial Models,” was a picture of the Altair 8800. Energized as he had never been, Allen showed the magazine to Gates, and within a few days Gates had called the maker of the computer, Micro Instrumentation Telemetry Systems (MITS), and told them that he had written a BASIC computer program that could be used on the Altair.

This was a lie. Gates and Allen were just trying to gauge interest from the company. But MITS was deep in its own deception: the computer shown on the cover had not been developed yet, and even the prototype had been lost in shipping. Still, the magazine article had generated interest far exceeding expectations, so MITS asked Gates and Allen to come in and demonstrate what they were thinking. Only then did the two set out to write the code. Gates focused on programming while Allen worked on simulating how it would work on an Altair 8800, which they didn’t have.

At the meeting eight weeks later, the program worked perfectly, and MITS arranged a deal to purchase the rights to Gates’s BASIC. Gates would later say that it was at this moment he knew the software market had been born. Yet, despite his growing certainty of the opportunity in front of him, Bill Gates waited another 12 months, until his junior year, to drop out of school and, with Allen, form Micro-Soft. And even then, the company might have amounted to little more than a footnote in the history of software without Bill Gates’s mother.

Long active in community service in the Seattle area, Mary Maxwell Gates became the first female president of the United Way of King County and eventually chair of the executive committee of the national United Way, then one of the most influential nonprofit positions in the world. Serving on the exec committee with her back in the early seventies were, among others, John Akers, who would later become the CEO and chairman of International Business Machines (IBM), and John Opel, who preceded Akers in both positions.

Mary Gates mentioned her son’s new business to Opel, who by many accounts then relayed this information to other top IBM executives. There’s no definitive record of what got said when to whom, but only a few weeks after Mary Gates got the ball rolling, IBM took a huge chance by contracting with Bill Gates’s fledgling company to develop an operating system for the company’s first personal computer. The success of both the IBM PC and the Microsoft Disc Operating System (or MS-DOS)—and the sweetheart deal that let Microsoft retain rights to its software—is what ultimately made Bill Gates the richest man on the planet.

Experience, Not Faith

So, did Bill Gates walk away from one of the world’s most coveted degrees toward an uncertain path? Well, he did ultimately make decisions from which there would be no turning back. That part of the myth is dead on. But was Gates a great risk taker? That’s a more complicated story.

His family’s money and position provided cover for his youthful computing hijinks and helped assure that he would have the best education available. As for the famous Harvard dropout story, he didn’t really. Rather, he took a formal “leave of absence,” a kind of emotional umbilical cord that kept him tied to Harvard long after he had vacated the campus, just in case things didn’t work out. But by then, he had already turned the odds in his favor. After half a decade of dancing with the opportunity, beginning early in high school, he had already covered most of his downside risks. He knew, for example, that he loved the work, and the early Micro-Soft had projects in the pipeline.

What’s more, Gates had validation that both he and Allen were highly competent with this new technology, and he could see that the topside potential was huge. The industry was just emerging, and his mother was in the particularly influential position of head of a United Way executive committee that also included two future CEOs of the world’s dominant computer company. As they say, it’s often not what you know but who your mother knows that can land you billion-dollar contracts.

Far from being one of the world’s great risk takers, Bill Gates might more accurately be thought of as one of the world’s greatest risk mitigators. And in that, he is not alone. The simple fact is that everyone is afraid of risk at some level, including everyone I interviewed for this book. That’s a given of human nature. But the further fact is that Door No. 3 is a myth, whether we’re talking about the myth of Bill Gates or the myths that we privately tell ourselves.

You don’t have to be fearless to make dramatic changes in your life. Transformative change isn’t propelled by raw courage. It’s “sparked” by a series of events that build exposure and experience, both of which help to create asymmetric risk. Through sparking, the upside opportunity is confirmed while downside risk is mitigated. Ultimately, the leap—when it comes—is not one of faith but of experience, even of comfort, just as it was for Gates.


Interested in more behind-the-scenes stories? Check out Leap. It can be read in two quick sittings and will get you off your ass to do whatever it is that you aspire to do.

Related and Suggested Posts:

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The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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188 Replies to “Do You Really Know Bill Gates? The Myth of Entrepreneur as Risk-Taker”

  1. Great read, and pumped to get this book. Given the downturn in events recently, I’ve taken a part-time job…wasn’t my dream, but it was necessary for sure. What is interesting is that I find I get MORE done without the hyper-stress felt in the winter/spring. Having a bit of cashflow helps me focus and build. It’s seems then important to discover you’re own threshold for risk/stress and try and exist there. Easy to say, hard to do. Experience is the only guide.

    Love your blog Tim.


  2. I know a few entrepreneurs in the UK and France and the funny thing is that they don’t really have that much in common other than they only take a bet when they can calculate the risk. The risk appetite changes from person to person but none of them go into anything blindly.

    btw, I enjoyed the post, thanks.

  3. Tim,

    I already new some part of the story of Bill Gates but the details here are very inspiring.

    Mass media contributes to spread the poker player entrepreneur type which is why most people never start their businesses.

  4. Books like Outliers, Blink (which I a currently listening to) and I presume Leap is that they are one sided. This is perfectly natural of course, but what about the people who took amazing risks to achieve, or who didn’t come from the “right ” environment?

    I will read the book because it sounds interesting, but I while I am reading I will try to remain aware that just like everyone else I tend to look for evidence that confirms what I already believe to be true.


  5. Tim,

    I read your book last year in one night and, in eleven short months, have entirely changed my circumstances. I have achieved DEAL. But, I still work for the same company because I love the project I’ve been trying to launch for five years, the company itself, and its customers. In fact, now I work MORE instead of less, make the same money, and haven’t started any side business. But that’s irrelevant. Your “buffet” offered me the meal I wanted.

    DEAL is exactly the incremental step taking you just mentioned in one of your replies to someone who practically accused you of reciting Gladwell’s thesis in Outliers (an excellent read).

    As with the comparisons with Gladwell, I can see how you’re looking at it from a different angle. Incremental risk taking is the only risk taking I know. Why make it black and white and ruin years of hard work with some 50/50 luck?

    Tim, while lots of your blog posts are irrelevant for this audience of one, this post today re-affirms I should stay subscribed.

    Thanks for taking the time to read this sir.

    Kevin Vandriel

  6. Hey Tim,

    I am going to go out and buy fifteen of your books (update version) and give half to my most influential connections and the other half to a couple local libraries here in LA.

    Keep up the amazing work!

  7. @Liam McIvor Martin

    RE: Any suggestions to help motivate university students into entrepreneurship?

    After spending 5 years teaching little kids in Taiwan English and 29 years teaching “adults” to leave me alone and let me do what I want to do, what I’ve learned is that it’s all about “framing.” Your students can’t see the gems that you see in the text because the text doesn’t relate to them. If they’re my age or younger, I’m sure a title change to “The 80 Hour Gaming Week” would have motivated a few of them… lol

    I also HIGHLY recommend “Got Game” (for both gamers and “old guard”).

    @Lloyd Budd FRESH! Tim! We’re waiting… 😉

    @Reijo Agreed 100%! The Alchemist has the SCIENCE!

    @Ergest Good lookin’ INDEED! I’m gonna have to put some money in the bank and order that! Or get my girlfriend to do it… 😉

    @Dynasty I accept your challenge! First I’m going to get my book back from the guy that stole mine and donate it to the downtown library, I’ll figure out my next move after that. 🙂

  8. Fabulous story. I’m usually deterred by too much text (being completely ADD as most people in my generation generally are) but this one got my attention.

    My entrepreneurial friends and I were just talking about the risk about going about your own thing today. Now I feel so much better. It doesn’t have to be all about having nothing to eat and complete desperation. Woot!

    Thanks so much Tim. I just bought the book (also recommended yours to my friends)!

  9. I like reading your work because you seem very curious and creative in your relationships to things, so big thanks for the explorative spirit.

    This article didn’t move me particularly, for a few reasons I think. Firstly, it is largely a historical account of another guy, and secondly because the point you were making seemed to be how you don’t need to take big risks to be an entrepreneur, but the example seems to be of a guy who had the freedom to be creative and curious with his career/lifestyle because he came from money and was in a wealthy school that gave him access to the technology forming the latest upcoming trends. What I draw from this is that if there was a myth about Gates being a risk taker, than it was wrong, he was simply a product of good breeding, financial security should anything go wrong, and being in the right place at the right time. I don’t think your example helps your argument, but like your stuff for the most part old bean. Thanks

  10. Hey Tim,

    I’m a first-time commenter at your site – been here many times.

    Great stuff!

    I was inspired to comment here today, though, because I’m glad someone is telling it like it really is. As a former scientist, I can tell you that what holds true for winning the Nobel Prize holds true for big business. It takes work, a series or good luck, happenstance, money, and planning.

    The cliche, “There’s no free lunch” is overused and popular for a good reason. Because there is no free lunch.

    Thanks for the work you are doing to change the world. Cheers!

  11. Hey All 🙂

    OMG, you guys rock! I emailed @MiltownKid and here’s what I said,

    ” I just posted a comment; donating updated version of Tim’s book to local libraries. Perhaps, you would be interested in donating at least 1 book to a local library? If so, post your generosity on Tim’s blog.”

    He’s his response (freak’in amazing) ” @Dynasty I accept your challenge! First I’m going to get my book back from the guy that stole mine and donate to the downtown library, I’ll figure out my next move after that. :)…I’ll get my friend in Taiwan to do the same thing…”

    And no joke, his friend from Taiwan got a hold of me.

    Thanks so much for your tremendous support. Join the fun and celebrate with kind generosity. Many, many, thanks.

    Have a fabulous night 🙂

  12. Hello, Tim. I’m a Chinese reader for your book <>. My english is poor so I hope you can understand what I said. I just read the first chapter and start to action. I want to build a company and be a CEO. I start to find some success CEO and email or SMS to them. I begin to do this the day before yesterday. I have email two CEO but nobody reply.

    Suddenly, I remember you. You are a success CEO and like to help others. so I come to your blog and ask you two question.

    I’m 21 years old and one years later will graduate the college. I have no forte, but want to build a technology company,like Internet company,mobile phone company and so on.Can I success?

    I know nothing about how to build a company, only a dream. but I will do. Can I success?

    I almost know your answer , I can success. But I want to hear your suggest still. The two question is only want to recognize you. And can you teach me what to ask when I first time to email a CEO?

    Your friend is so many and the comment is so so many , I hope you can see my comment.

    Your chinese must good because you come to China so many time, so I translate my poor english to chinese.







  13. interesting topic. I always like different perspectives on the same person. I think that way everybody can learn whatever he needs to learn from it. For example one person can be a karate master and an excellent cook. If I want to learn cooking I’ll book such a course with him and if I’m interested in karate I’ll go to his dojo.

  14. Bill Gates had the advantages of connections and know how on starting a business, but anyone can (and should) do it – social media is a great way of making connections and there is plenty of practical knowledge on the web on how to create a business. – after all entrepreneurs and small business are the people who will turn the economy around

  15. Bill Gates was in the right place, at the right time in history doing the right thing. Obviously, his passion was the driving force behind it all. How else could someone go for a decade without taking a vacation!

  16. Hello I’m Italian and reading this post I can tell you that the story is completely different from that translated into Italian, is very similar to that of the film Pirates of Silicon Valley. From what I can understand Bill Gates took advantage of the opportunities that had simply, has recognized and exploited them. everything is to understand the opportunities. Opportunities are words, we have before us the letters, combining letters we create our own opportunities.

  17. So, I just finished the book, and I highly recommend it. Very good stuff, especially the last chapter. Rick notes that in biology, variation is necessary for evolution, and we should think similarly in finding our “vocation.” Finding something that is the best fit for you is aided by gathering various experiences and then “evolving” from those experiences to your ideal work.

    There also seems to be some concern in the comments that this recommendation for the book is non-authentic because of the potential financial benefit to Tim, but this does not seem to be a well-founded fear. In this “business”, nothing can be more important than trust. Tim has thrived at what he does not because of some marketing scheme, but because he makes a positive impact. He has my trust because 1. his book is very good and 2. every book he recommends is also very good. I have read most of the “restricted reading” that he suggests, and these are all excellent reads. Do you think Tim would want to break our trust by recommending some crappy book so that he can make a few cents on the dollar for every book sold? That just isn’t worth it. Trust pays.

    If this book was recommended by Tim and it was a crappy read, I wouldn’t read more books that he suggests. Short term gain of a few pennies, but a long term loss. Even though there may be some monetary gains for this recommendation, that is fine by me, because the bottom line is that I benefited from this recommendation.

    To many companies fail to realize this concept. They just take the money and run, and while this works in the short run, it is simply non-sustainable. Any product can do well initially, but if its crappy, people stop buying it.

    A good investment matures over time, and building trust is one of the finest investments you can make.

    1. Thank you for the comment, Tony. It is a great read. I encourage anyone who thinks I post _any_ book for financial gain to sign up for Amazon affiliate and give it a go. Even if you sell hundreds of books, which only a well-read blog can, it’s pennies compared to anything else most people could be doing.

      If I were blogging for money alone, I’d have both advertising on this blog, right?

      Thanks again and all the best,


  18. Hi Tim:

    Gee whiz after reading all of these comments I sort of wish now that you chose another chapter to feature from The Leap.

    Folks this book is NOT about Bill Gates and/or “who you know vs. what you know.” And it def is NOT similar to Outliers.

    It’s about how to find “the place where your deep gladness and the world’s deep hunger meet” as Frederick Buechner speaks about.

    It’s a tool box for people who may not know what they want to do yet are moderately or very certain it’s not what they are currently doing. It’s also for those that are on the path but want it to become more easeful.

    After you take Smith’s primary color assessment test he asks you to lift it up beside this ruler. What could you create with your gift that would be Big, Selfless and Simple?

    Now mind you Selfless doesn’t mean unprofitable. In fact the funny thing is those are usually the ideas that really generate. Meet the needs of the market place. That is job #1. And when you really focus on other people and their needs and where and how those needs can be met by your service then you’ve found yourself a hit. Just like you did Tim by meeting the need we all had to not work crazy hours every week.

    Thank you for featuring this book and always turning me on to powerful people and useful information. You never waste my time and I thank you so much for that.

    Warm regards, Kim

  19. Hey Tim, I was wondering if you could put your random show as it’s own topic in your topics menu or have it’s own button at the top menu of your blog. Also if you could throw it in itunes so I could subscribe to it that would be equally awesome.

    with a smile,


  20. Thank you, Tim. I’ve been riding the entrepreneurial roller coaster for a couple of months now, and this post reminds me that I’m creating my muse the right way. I’m using only cash, and I’m wrapping up the last 5 hours of a music degree while I start my business (not the one in my URL–that’s for quick money). I won’t miss a beat if the muse fails (but the market testing reminds me that it has potential).

    So the “career-path” umbilical cord, the worst-case scenario analysis, and the support of positive people made pursuit of this idea inevitable. Take heart, everyone.

    Thanks for being so positive! Haha.


  21. TIm

    I have read your book, it’s great.

    Anyway, I think becoming richer depend on cognitive and thinking.

    So, listen other oppinion of richers, it will be advantage for listener.


  22. Interesting post, but maybe you can explain to a foreigner: Why is “career” on the cover such a bad thing? Any negative connotation I am missing? I thought it sounds rather positive..

  23. I find it funny that you picked a picture of MC Frontalot and no one has picked up on that (or at least mentioned it). In that gaming world he’s a bit of a mini celebrity. I was actually expecting you to writing something about him in the article. Just found it funny. 🙂

    Good article though, thanks.

  24. Hi, I am compelled to share a few of my thoughts here..!!

    (1.) In Tim’s book besides all the concepts (that are excellent), I think the most important one is “To begin with the end in mind”.. So the question is “Do you want to be the richest man or among the richest men in the world ..!!”

    (2.) Though, by reading about people like Bill Gates and his likes, you may generalize a few things, but again quoting from Tim’s book – different people have used different methods and approach to achieve success and all of them are right. Make your choice and take the road that’s best for you.. but do not forget where you want to reach so that you begin with the end in mind !!!

    Hence …

    (3.) I look at money as a resource to buy things that I need or want but if one has to pay for money (yeah !! you have to SPEND your time making money.. so that’s a price !!) in denominations of the most limited and scarcest resource called TIME then one is very poor, cause if you have money in your pocket but no time to spend(read as enjoy) it then I pity you, cause you are living “below the line of time poverty”… !!!!

    4 Cheers to the 4 hour work week… !!! and 164 hours enjoyment week… !!!

  25. @Eric: Also foreigner, here. (insofar as anyone can be a foreigner on the interwebs)

    “Career” has a negative feel to it for me as well. When I see “Improve your career”, I think about climbing the corporate ladder, sucking up to managers and getting promoted to a larger cubicle.

    I guess most people here are after “lifestyle design”, which would often involve ditching the whole corporate thing and doing something independant.

    That’s my take, anyway.

  26. Love the discussion about the word “career”. Actually, Tim was right, it is the wrong word for the message of the book. In fact, I had a major fight with my publisher about changing it. In the end, we left it, because it at least narrows down the audience initially (you cant reach every group until you have directly reached one group). Who knows, may change with the next printing.

    The negative connotation is exactly related to the traditional corporate ladder. Sure, that is still the goal for some, but not for many these days. I think those attracted to Tim’s site and conversation are drawn, as I am, to the notion that life should be lived uniquely, and not along a path set superficially by someone else.

    The last chapter of my book, The Leap, is called: A Perspective on Life-Work Design (certainly a term inspired by Tim’s Lifestyle Design). The point of this entire chapter is that everyone’s ideal path is unique to them, if you only have the courage to pursue it.

    (from the last chapter): “What you are doing now is a matter of record. What you should be doing – what work is right for you, what career track will bring you the greatest fulfillment, what summit to be looking at the world from, where your leap should be taking you – is utterly personal and singular. A million monkeys at a million word processors couldn’t begin to scratch in print the surface of possibilities. That’s where the real clarity lies, where careers become callings. That’s where your future begins.”

  27. Love the story. Really shows where people come from.

    In life I always like to remember if someone has done it before then you can achieve it to. When you look at stories like this risk is only a perception in your mind.

    I really am waiting for your health book to come out. Can you work really hard on it as I have finished the 4 hour work week and ready for the next offering.

  28. Bill Gates isn’t lucky – he is driven and focused, and able to both seek out and see opportunities when and where they arise.

    There is actually, a classical treatise on this type of “luck” in someone’s own words – The Conquest of Gaul – Julius Ceasar. A lot of plebes in Rome probably thought he was lucky to .

  29. Tim,

    Just got back home after a 12 hour car ride listening to the 4HWW twice.

    WOW! I am pumped!

    I just signed a sweet deal with a company in NJ, and we are moving forward with my invention. The DCT “Diver’s Communication Torch” will be on the market in 2 Months. After 5 Years it has finally happened. Thanks to reading and listening to your book and acting and doing it.

    I want to send you one as I know you are a certified Scuba Diver.

    Thanks for everything, and I hope to run into you while I am globetrotting, The dives will be on me… buy the beers after.



  30. I can’t help it but I notice a lot of discussion on LUCK and RISK. Which I believe are very deceiving if discussed on their own.

    Many successful people mention Luck as a contributing factor to their success. I believe they use that word to sum up events and things in their life they’d rather not discuss or wish not to share (secrets, not too proud moments). You are lucky if you win a million in a lottery – no doubt. But as far as business strategy or concept – find it very useless. How do you replicate and objectively measure someones luck?

    RISK – another very useless variable to discuss on its own. Of course RISK exists, you are at risk the minute you are born. Everything you do in your entire life involves risk. LIFE is a very risky endeavor. Amazes me why are people so afraid to go into business because of this variable. We are OK with short term risks, but no one likes to make a life changing decision because of risk.

    Yet, so many people marry a partner just to divorce them and loose half of everything (better yet, do it over and over, helloo), engage in activities resulting in short term pleasure knowingly risking long term goals – in other words we do so many stupid things everyday that are risky – but don’t even bother questioning them. Yet we all think of our-self as exceptionally bright.

    Don’t ask yourself whether risk exists or not, whether it is bad or not. Ask yourself how it BLENDS and coexists in your life. ALWAYS consider risk with all the other variables involved in creating your life. One of the most important partners of risk is PROBABILITY.

    INCREASING the odds and PROBABILITY of your success is the name of the game. Risk all of a sudden becomes a very relative term.

    Rambled enough here. Aren’t you luck to read this long post? 🙂

  31. Tim — GREAT THREAD

    I think a lot of folks are missing the point here.

    1) Un-informed Optimism

    —2) Crash-Burn Escape Velocity

    3) Informed Optimism

    Escape Velocity has two roots: 1) Humility (an “ability” or “skill,” in terms of speed, at recognizing truth and submitting to it) and 2) Forward Moving Will-Power.

    Will and Humility (given the above definition) can we ever move-forward and submitt to self-realized genius.

    I have a site going live in 6-8weeks (Hero Talk); wherein we are playing with the biggest names in Military and 1st Responder Training — we have an 18,000,000 community with total top-down and bottom-up groundswell.

    We’ve been at this for 18 years and NO-ONE (including ourselves) has made a dent in PTSD Training owing to training costs.

    I meditated on the Success / Failures of Youtube and Facebook and came up with a new model.

    You are 100% Right — When you talk about “The Myth of the Entrepreneur” — who was I even 6 months ago, just another mid-level trainer. Now I’m working with the biggest names.

    Thanks for Shining the Light Brother,


  32. Hi Tim and all

    I’m trying to get ideas for my ‘muse’ which for me will be an internet based business which I can run without giving up my ‘day job’ in the first stage.

    I need a little help – I have an MBA (so I shouldn’t be too bad at general business stuff), but I’ve always been corporate and building entrepreneurial muscles is new for me. Now it’s really just about identifying business opportunities and the challenges of starting up online.

    What do you think of the following books:

    Moonlighting on the Internet

    (Yanik Silver with Robert Olic)

    The Online Professor’s Practical Guide to Starting an Internet Business

    (Danielle Babb)

    Are there any others I should look at?

    Many thanks in advance

  33. Hi Tim,

    More than the risk-reward scene, you can’t ignore the fact that Bill Gates was little more ahead of his time than anybody and saw first what was coming. Even such an ability is extremely rewarding and if it was only about taking risks to succeed then Las Vegas would’ve seen unmanageable crowd. But there’s no denying the fact that not all the moms are capable of clinching deals for children!


  34. hi fans of tim-

    I’m wondering if anyone’s come across any of Tim’s thoughts on personal RELATIONSHIPS in addition to the blog about the value of irritating people?



  35. I just came across this post today and I thought to myself; this is the exact situation I am in”.

    It’s a common assumption that those who have become successful entrepreneurs risked everything to get where they are.

    Keeping our families secure (as we so think of it) by having a job that pays the bills, seemingly allows us to reduce the risk of starting our own venture.

    The ultimate goal is financial independence, but it’s important to satisfy the basic needs of those who need you.

    Bit by bit, we’ll get there.

    Thanks for the great post Tim!

  36. I have to agree with Shane on Outliers being more absorbing than Blink. i didn’t get to the end of the latter which is unusual for me when reading a book.

    Outliers had little to do with risk, for me it was saying success is a combination of being in the right place at the right time and putting in a LOT of work.

  37. We see it everyday… being an entrepreneur is risky, but in fact, NOT BEING one is even riskier.

    It may be slower at first, but in the long run it pays off tenfold 🙂

  38. I’ve had a sneaky suspicion that this was the majority route with entrepreneurs being that I’m doing the same plan myself. One year in to my first business, I’m still working full time for another job until the see saw turns just enough where the “risky” jump is nothing more but a small step. I suppose there are times to gamble, but it’s nice feeling the water first!

  39. Hey Tim,

    Calculated risks, rather than just any risk, is what lets you achieve your goal faster.

    You make bold moves to focus on the big wins, but you don’t mindlessly try stuff. You plan and figure out what would be the most effective way to do something that’ll give you most of the results (80-20 style), and take your risks there.

    Looking at the phrase ready-fire-aim, you do indeed fire and just do it (hope me linking to an article I wrote isn’t spammy – just thought it’s relevant and helpful to the topic)… but that ‘ready’ stage is where you calculate the firing beforehand. It isn’t simply called fire-aim for a reason.

    You have limited ammo, so you want to make it count. You can’t predict the future, but you can analyze your choices and focus on the 80-20 ones.

    Mindless risks leads to wasted resources. Calculated risks leads to big wins.

    Great reminder to take risks but to be selective and make them calculated,


  40. hey tim,

    nice article! i think bill is a great Entrepreneur, he makes shit to gold 🙂

    we can learn a lot from those people.

  41. Just a thought :

    I´d put the definition of risk-taking differently : people like Gates are able to exactly calculate risk – what they finally “take” is a specific degree of uncertainty – not risk.

    And obviously they manage uncertainty better than their fellows.



  42. Hi from Mexico.

    Just an update:

    I’m guessing this post is from 2009. As of March 10, 2010, Forbes Magazine considers Carlos Slim the richest man on the planet, just .5 billions up from Gates. Financial markets go up and down.


  43. The Bill Gates story has always fascinated me, well at least the parts I was aware of. This article has highlighted other points that I wasn’t aware of so it’s been quite an eye opener for me as I have tried to model myself around entrepreneurs like Bill Gates.

    It’s really about perceived risk. You could say Bill Gates took a risk from leaving Harvard (although technically was a ‘leave of absence’) he still had to make a decision that most would of faltered on.

    I agree with you though Tim, in my view I would more see him as a risk mitagator rather than risk taker 😉

    Thanks for the post.

  44. At some level everything we do is a risk, from crossing the street to eating a burger. The key is to have as much informtaion as possible about the risk versus the reward, then make the decision

  45. I’m mos struck my Bill’s constant planning and creativity. WE always assume brilliant business leaders “fell” into their position, but chance and balls are a great combo!

  46. Tim, I’m a little late responding to this one but wanted to point something out. The idea of the entrepreneur as a “risk taker” I believe stems from the statistical data that says 9 of 10 businesses fail in the first year (I think I remember the numbers correctly) and that 9 of 10 of those businesses fail in some relatively short period thereafter. What those statistics fail to point out is how well conceived were those businesses and were the founders starting a business or painting themselves into a position of self-employment? Few of the small business owners I know really had much of a plan say nothing of having a planned virtual architecture that will allow them to remove themselves as the choke point in the business.

  47. Did you ever watch the movie “Pirates of Silicon Valley?” It’s basically this entire post, but they go into a lot more detail in certain areas. They also include a lot more about Steve Jobs, and the Apple/Microsoft competition. This article reminded me of it, and I figured that if people haven’t seen it, and they are interested, they should check it out.

  48. Really like the post. I have been in the middle of keeping one foot in and one foot towards the future. I always give myself an excuse saying that I am too busy to work on my own project after a long day at work.

    Also at work I am not happy at all. It isn’t awful, but I feel I could be doing much more. When does it become too far trying to hold on to something while working toward something else? Do you have to wait until you are successful at something else before you can move on to the next project?

  49. Hi,

    As soon as I read the title I wanted to know more: mainly because I disagreed completely due to some previous scientific readings I had done while studying Epidemiology at Cambridge University.

    I have attached the link to one article in Nature Magazine entitled “The Innovative Brain”, which principally explores the difference in risk taking behaviours of entrepreneurs and other business actors. Interestingly enough, the article was published in Nov 2008, just less than a year before Tim wrote this one.

    Of course, there are different approaches to the same problem or observation, but this scientific evidence, I believe, could be a pertinent addition to the cogitation one can have on such a topic.

  50. Hi from Mexico.

    Just an update:

    I’m guessing this post is from 2009. As of March 10, 2010, Forbes Magazine considers Carlos Slim the richest man on the planet, just .5 billions up from Gates. Financial markets go up and down.


  51. Bill Gates decision was a calculated risk; well though out and well planned. It’s not like he jumped in head first without a solid plan. Life is full of risks; sometimes not taking a chance is a risk by itself because you risk not ever reaching your dreams.


    I’m looking for a little random advice to help me think straigt and act right.

    My father’s got a pretty successful electrical engineering company here in Brazil and he’s the Superman-do-it-all of it. He has put his WHOLE time and life on it. A couple of years ago he started burning out of all the effort, but is still keeping his business.

    The cup will be passed on to me if I want, which I do but I’m no electrician and also still want to keep living my life outside of the work. Thus I’m looking to apply what I learnt in T4HWW and automatize as quick as possible. I already started making my moves.

    I need an Elance type website for the Portuguese speaking world. Does anyone knows of one?

    Some case studies would be VERY, VERY welcome to help me guide through this as I also have to prove to him that this is possible and it won’t kill the company in the process.

    I can be easily reached at cabeludorafael-at-gmx-.-de.

    I’ll also be checking this post for any tips, tricks and the like.

    Cheers all,

    Raffy from Brazil

    1. By the way, I apologize if my post seems completely misplaced. I just know that Tim’s blog is probably one of the top places where knowleadgeable people gather therefore here I am, searching for wisdom.

  53. Definitely imagine that that you stated. Your favorite reason appeared to be at the web the easiest thing to take into account of. I say to you, I certainly get irked even as other folks think about worries that they just do not know about. You managed to hit the nail upon the highest and defined out the entire thing without having side effect , other people could take a signal. Will likely be back to get more. Thank you

  54. In order to build a brick wall, you must lay each brick separately to reach the final product. From looking and studying successful people, I have learned that it is crucial to not jump from beginning and expect to reach your goal immediately. You must learn each important step along the way. Thank you for this post and introducing me to yet another great role model.

  55. My question is, was Microsoft really an IBM venture and they were looking for a front man to head the job? IBM, not looking to be a monolith accused of having domination over the market, and seeking to avoid anti-trust issues, needed to spin off their software division. Enter the well-connected Gates Family.

    Big IT, from the get go has been developed for eugenics efforts. “Track, trace and database!” The father Gates being involved in Planned Parenthood and mother with IBM. IBM supplied the computers for the NAZIs during WW2 to help them in their efforts to catalog all the prisoners. William and Mary Gates. A match made in heaven.

    Their son just gets the honored job of heading the software division of IBM, renamed to Microsoft to divert attention.

  56. I am an avid hockey fan but also a fan of business entrepreneurs like Daryl Katz. He paid $200 million for the Edmonton Oilers in 2008 and he is currently working to refocus his efforts to build Canada’s largest mixed use-sports and entertainment district. He is by far one of the most successful businessmen in North America. Check out this link for more info about his current business dealings.

  57. Great and insightful on overall. Bill Gates knows it well, success doesn’t follow those who fear risks. You have to try again and again only by that can you realize you can really do something.