Insanity: The Secret of Entrepreneurship

“Very tough to sleep most nights of the week.  Weekends don’t mean anything to you anymore.  Closing a round of financing is not a relief.  It means more people are depending on you to turn their investment into 20 times what they gave you,” writes Paul DeJoe, founder of Ecquire, about being a startup CEO.

While The Social Network movie officially made entrepreneurship sexy, in reality, it is hard work, sweat, and tears. And to really make it, you have to be at least a little bit crazy to keep going despite constant failure.

Here is why entrepreneurs are insane:

1. Living In An Alternate Reality

Face it, you are a rebel, a crazy one and a troublemaker!  Apple’s Think Different Advertisement said it best:  “Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently. They’re not fond of rules. And they have no respect for the status quo. You can quote them, disagree with them, glorify or vilify them. About the only thing you can’t do is ignore them. Because they change things. They push the human race forward. And while some may see them as the crazy ones, we see genius. Because the people who are crazy enough to think they can change the world are the ones who do.”

Steve Jobs, perhaps the greatest entrepreneur of our time, is known for bending the world to his will. “In his presence, reality is malleable. He can convince anyone of practically anything,” writes Apple computer scientist Andy Hertzfeld. “Amazingly, the reality distortion field seemed to be effective even if you were acutely aware of it, although the effects would fade after Steve departed. We would often discuss potential techniques for grounding it, but after a while most of us gave up, accepting it as a force of nature.”

This attitude of seeing reality differently, is most apparent in Sillicon Valley, where most technology entrepreneurs live:

“High unemployment? Crippling debt? Not in Silicon Valley, where the fog burns off by noon and it’s an article of faith that talented, hard-working techies can change the world and reap unimaginable wealth in the process. “We live in a bubble, and I don’t mean a tech bubble or a valuation bubble. I mean a bubble as in our own little world,” says Google Chairman Eric Schmidt. “And what a world it is: Companies can’t hire people fast enough. Young people can work hard and make a fortune. Homes hold their value. Occupy Wall Street isn’t really something that comes up in daily discussion, because their issues are not our daily reality.”” writes Brad Stone in a great article titled “It’s Always Sunny in Silicon Valley”.

2. Constant State of Rejection

Insanity is believing in your product so much that even when 1000 people say no, you still forge ahead, become more agile, and iterate over and over while injecting moderate updates to your product with hopes of bringing to market a new way of seeing or doing something. It is then, and only then, after living in a constant state of rejection, that you – through a tiny pinhole – see the light.

Entrepreneurs live in a constant state of rejection. They’re turned down by investors, by customers, and sometimes by their own friends and families. The successful ones see rejection as an opportunity to learn more and to find new ways to challenge traditional thinking to get what they want.

Skype was turned down by 40 venture capitalists before finally getting funding. In 2011, Skype was sold to Microsoft for $8.5 BILLION.

Pandora was rejected by VCs 300 times before finally raising funding, which had to go out as back pay to employees who’ve been working without pay for the past two and a half years. Now, the company is trading on the New York Stock Exchange and worth billions.

What about all the other rejected startups? Check out Bessemer Ventures anti-portfolio. Oops? These certainly would have been incredible investments, but they were all turned down for different reasons.

As founder and angel investor Chris Dixon puts it, “if you aren’t getting rejected on a daily basis, your goals aren’t ambitious enough.”

“I regard every defeat as an opportunity.” – Jean Monnet

But the thing about successful entrepreneurs is this: …when they fail, they do not waste much time lamenting; blaming; or, at the extreme, quitting. Instead, regarding the failure as a learning experience, they try to build upon its lessons in their future endeavors. (From Creating Minds: An Anatomy of Creativity Seen Through the Lives of Freud, Einstein, Picasso, Stravinsky, Eliot, Graham, and Ghandi)

3. All Work, No Pay

“Insanity is often the logic of an accurate mind overtasked.” – Oliver Wendell Holmes

It is no secret that becoming a successful entrepreneur takes more than a few sacrifices, especially when it comes to sleep and free time.

“As a startup CEO, I slept like a baby. I woke up every two hours & cried,” said Ben Horowitz, who previously co-founded Opsware, which was acquired by Hewlett-Packard for $1.6 BILLION, and is now the co-founder of venture capital firm Andreessen-Horowitz.

Founder of Twitter and now Square, Jack Dorsey currently works 16 hours per day, 8 hours at Twitter and 8 hours at Square. Mark Zuckerberg puts in 16 hours per day as well just on Facebook. These founders are definitely not alone.

While working as much as 90 hours per week is not uncommon in some industries such as law or finance, keep in mind that entrepreneurs who are just starting out do not get a paycheck for their work every two weeks, and there is no guarantee they ever will. Entrepreneurs understand the mindset of delayed gratification, the ability to wait in order to obtain a larger reward. The more sweat equity they put into their efforts, the larger the reward. In many instances, it may not be $1.6 billion dollar reward, but with relevance it may be a new contact, a new feature, a pivot or a realization altogether that their product sucks.

In 2008, Evernote had about 2 weeks worth of money left and founder Phil Libin was planning to shut down the company in style the next morning. At 3am, as he was ready to go to bed, on edge with the fear of having to tell his staff the bad news, he received an e-mail from a Swedish Evernote fan. The email’s back and forth quickly turned into a Skype chat, and within 20 minutes, Libin and his fan worked out a basic agreement for a $500,000 investment, giving Evernote another six month of runway and saving them from bankruptcy. This chance investment, at the most perfect time, gave the company the time it needed to figure out their product and reach the point it has today. Evernote has recently raised a $70 MILLION Series D round at a $1 BILLION valuation.

Entrepreneurs don’t just see the world differently, they create it, and that requires at least a little bit of insanity.

Request a call with some of the entrepreneurs mentioned in this post:

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  • Chevan

    So true.

    • Dan Martell


  • Joss IHate-fb Candy

    I’m a serial entrepreneur (or the king of harebrained schemes) & I’ve barely made a penny from most of my ventures but I refuse to give up. I hate the way the world works & I won’t be it’s slave. I’m an expert at rejection & totally crazy. Bothered? I don’t earn a fortune but still make a living MY WAY & that’s what makes it worth it.

    • Dan Martell

      I like your style!

  • Mata

    Excellent Article! Worth sharing and I did!

  • Chrissy

    I feel normal reading this 😉 Thank you for a wonderful post!

    • Chrissy

      Ooups…”felt” not “feel”.

    • Dan Martell

      Knowing that it’s normal is step 1) … then leveraging that feeling to create wonders is step 2). Just keep moving forward. All the best.

  • FitMissy

    OMG! So true! All the way!

    • Dan Martell

      Appreciate the comment.

  • Steve Piercey

    great article..thanks Dan

    • Dan Martell

      Thanks Steve!

  • FfionKitchenGadgets

    Great article

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  • Mack Thomas

    Great article. Im finishing my forthcoming book.”Entrepreners Dont Cry”, Im in need of true entrepreneur’s me (Mack Thomas) at

  • mony1