What I Wish I Knew When I Was 20

One of my favorite podcasts is Entrepreneurial Thought Leaders put out by the Stanford Technology Ventures Program. Entrepreneurial Thought Leaders is a lecture series with guest speakers from across different fields and industries. David Heinemeier Hansson of 37Signals, Mark Pincus of Zynga, Robing Li or Baidu, Steve Ballmer of Microsoft, and a great many of other founders, entrepreneurs have spoken at Entrepreneurial Thought Leaders. So when Tina Seelig, the person that runs the Stanford Technology Ventures Program, came out with a book I knew to put it on my Amazon wishlist. Sadly no one bought me anything off my wishlist so I bought it myself to read over the winter break.

A lot of the stories and lessons Tina dives into in What I Wish I Knew When I Was 20 she talks about lectures she gave back in May 2009 and in April 2006 at Standford’s Entrepreneurship Corner.

In What I Wish I Knew When I Was 20, Tina gives some important lesson on creativity, opportunity, and having the right attitude to invite both creativity and opportunity in what you are doing. For example, she speaks of having her students develop failure resumes and to highlight lessons learned from making mistakes. Her reasoning behind failure resume can best be summarized by the following quote from her book.

It’s a quick way to demonstrate that failure is an important part of our learning process, especially when you’re stretching your abilities, doing things the first time, or taking risks. We hire people who have experience not just because of their success but also because of their failures.

Aside from taking risks, and not being afraid of failure, she speak a lot of about having the right attitude to invite the correct atmosphere for success. A persons perspective is important to success, in one because each person defines what they consider a successful venture. Like in the movie The Social Network, where the Sean Parker character says “A million dollars isn’t cool. You know what’s cool? A billion dollars is cool.” For some people success is defined by having 500 million obsessive-compulsive users, and for others it’s about having 1000 paying customers. It is often the case that people let others define their success, but the truly successful are those that define their own success. And defining success has a lot to do with a person’s values and attitudes.

I took a lot of value away from What I Wish I Knew When I Was 20. For example, create a failure resume in Google Docs. I’ve also learning to try to negate the effects of negative thoughts, especially when trying or learning something new.

Here are some choice quotes from What I Wish I Knew When I Was 20:

  • Problems are abundant, just waiting for those willing to find inventive solutions.
  • Steve Jurvetson, a partner at the venture firm Draper Fisher Jurvetson, describes failures as the secret sauce of Silicon Valley.
  • Students are told that it is much better to have a flaming failure than a so-so success.
  • On reflection, there appear to be five primary types of risks; physical, social, emotional, financial, and intellectual
  • Experts in risk management believe you should make decisions based upon the probability of all outcomes, including the best- and worst-case scenarios, and be willing to take big risks when you are fully prepared for all eventualities.
  • Being too set on your path too early will likely lead you in the wrong direction.
  • Planning a career should be like traveling in a foreign country. Even if you prepare carefully, have an itinerary and s place to stay at night, the most interesting experiences usually aren’t planned.
  • The harder you work, the luckier you get.
  • Even when we think we’re paying full attention, there’s usually so much more to see.
  • I realized afterward that thinking about how you want to tell the story in the future is a great way to assess your response to dilemmas in general. Craft your story now so you’ll be proud to tell it later.
  • A few years ago I took a creative writing class in which the professor asked us to describe the same scene twice, the first time from the perspective of someone who has just fallen in love, the second from the point of view of someone who has just lost child at war.
    You shouldn’t take yourself too seriously nor judge others too harshly.

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