Try, Try, Try Again: An Essay


  1. In the book Gamestorming, Dave Gray and his fellow authors make the argument that if you know Point A and you know Point B, it is very easy to plot the steps necessary to get between the two points. And they ask the more important question – what happened when you don’t know what Point B is? They argue you need a completely different set of tools to make that journey into uncertainty.
  2. Carpe diem, quam minimum credula postero or “Seize the Day, putting as little trust as possible in the future.” We rarely hear the 2nd half of that.
  3. Daniel Cates is 21 years old and in 2010 he earned $5.5 million playing poker online, a million dollars more than his nearest competitor. Journalist Jay Caspian Kang, in his profile of Cates for New York Times Magazine says ” If an 18-year-old online whiz can play 12 hands at once, then by his 19th birthday, he is no less experienced than a career gambler who has sat for a dozen years at the big-money table at the Bellagio.”

  4. TED conference curator Chris Anderson believes online video is accelerating innovation. He points to Jon M. Chu and his dance troupe Legion of Extraordinary Dancers. “Because of the web, specifically online video, dance [is] evolving in Internet time. A series of challenge videos by rival groups of street dancers had created an upward spiral of invention as they strove to outdo one another. The best videos were attracting tens of thousands of views. Much more than pride was at stake. Chu knew something weird was happening when he saw a YouTube video of Anjelo Baligad, a 6-year-old boy from Hawaii who had all of the moves of a professional.”
  5. The Lean Startup movement, started by Steven Blank and now being taking to a whole new level by Eric Ries, combines the philosophies of agile programming with the methodologies of the Toyota Production System. In relationship to failure, Ries argues that projects that that require extensive specifications, months long development, and follow-on quality checking acquire ever increasing amounts of risk the longer the time between the idea and its release. “Minimum viable product” is the lean startup term for putting out only what is necessary to gather customer feedback. This eliminates the risk early in the process and with frequent iteration the product is never far from the (paying) customer and his wants.
  6. FailCon (yes, this is a real conference)
  7. Cursor founder Richard Nash asked me the other day what the implication of 3-D printing is for publishing. The direct corollary is print on demand. To this point, publishing has looked at POD technology, whether Espresso machines or Ingram’s buildings full of HP printers, as a mechanism to mitigate inventory risk. That is certainly important, but what if these “batches of one” technologies could be used to make publishing more innovative?
  8. In The Adventures of Johnny Bunko, Dan Pink  uses Diana the chopstick evoked genie to deliver  Lesson One : There is No Plan. He distingishes between Intrumental Reasons and Fundmanetal Reasons for career choices. Instrumental reasons are one that imply that it will lead to something else. Fundamental reasons are “inherently valuable, regardless of what it may or may not lead to.”  “[Sucessful people] take a job or join a company because it will let them do interesting work in a cool place–even if they don’t know exactly where it will lead.

  9. Another term from the lean startup methodology is pivoting, the practice of changing a component of your business model to improve your chances of overall success. In the startup phase as a company searches for a business model, a company may pivot several times.  While this might be viewed as failure, the opposite viewpoint would be that this extends the life of a young company as it adapts to better suit the needs of customers. Twitter was a side project after the primary product – a tool for podcasting called Odeo – was made obsolete when Apple added podcasts to iTunes.
  10. US Air Force Colonel John Boyd referred to the iterative process as the OODA Loop – Observe, Orient, Decide, and Act. Boyd believe the person who could complete the loop faster and more often would win the battle. Boyd never wrote a book, but many including Tom Peters have seeked to apply his theories to the business setting.
  11. The New York Times Magazine on their September 14, 2011 in their education issue asked “What if the Secret to Success is Failure?” According to research- zest, grit, self-control, social intelligence, gratitude, optimism and curiosity are the keys to success.

  12. Authors are starting to test titles and subtitles using Google Adwords. They create ads with their titling and then test various iterations against keywords that match with the contents of the book. Measuring the click through rates shows which titles produce better response. This ability to acquire feedback instantaneously and in large quantity is changing the way we develop products.

  13. Etsy is creating a marketplace for small batch arts. Kickstarter is funding small projects with patrons acting as investors; projects that couldn’t be created through commercial sources. Startup incubators like Y Combinator and Techstars are combining small sum angel investing, compressed development cycles, and high touch mentoring to produce a whole new set of startups. Grameen Bank has created microloans for people in developing countries to pursuit their dreams. These are all incredible examples of how the scale necessary to launch new products has dropped by two to four orders of magnitudes.
  14. “It’s better to fail spectacularly than to succeed tenatively.” –Roshi Jiyu-Kennett

  15. Derek Sivers, in his new book Anything You Want, says he misunderstood persistence: “Success come from consistently improving and inventing, not persistently doing what is not working.”
  16. Just Start: Take Action, Embrace Uncertainity, Create The Future by Leonard A. Schlesinger, Charles F. Kiefer & Paul B. Brown. The book was originally published as Action Trumps Everything: Creating What You Want in an Uncertain World advocating a simple three step process:

    Step 1. Make sure what you are about to do is something you really care about. It’s silly to launch into the unknown if you don’t.

    Step 2. Don’t over-think. Don’t imagine what might happen. Get started with what you’ve got in hand and take a small, start step toward your goal and find out.

    Step 3. Evaluate what you learn, and if you like the results take another step. In other words: Act. Learn. Repeat.

  17. Paul Graham saysBeing relentlessly resourceful is definitely not the recipe for success in big companies, or in most schools. I don’t even want to think what the recipe is in big companies, but it is certainly longer and messier, involving some combination of resourcefulness, obedience, and building alliances.”

  18. The First Try – Overcoming Fear

    The Second Try – Overcoming Failure

    The Continual Try – Embracing Iteration


1 –

2 –

3a – [Blank] –

3b – [Ries]

4 –

6 –

7 –

8 –

10 –

Suggested Reading:

  • The Lean Startup by Eric Ries (Crown, Sept 2011)  – In my opinion, this is the most important book of the Fall 2011 season.  The idea of iteration is one of several points in the book. I believe this book is the roadmap for how entrepreneurship will practiced.
  • Little Bets by Peter Sims (Free Press, April 2011) – Sims writes a whole book on the idea of making lots of little bets, rather than focusing on a few big ones. He uses stories from Pixar and Frank Gehry as well as research from Carol Dweck and Mihaly Csikszentmihalyi. This is a good book that pulls together a bunch of ideas around how it is less risky to more chances.
  • Obliquity by John Kay (Penguin, April 2011) – The subtitle is “Why Our Goals Are Best Achieved Indirectly.” This book makes the clear case that our lives our full of “pivots.” The book description makes the case very well: “The best way to achieve any complex or broadly defined goal-from happiness to wealth to profit to preventing forest fires-is the indirect way. As Kay points out, we rarely know enough about the intricacies of important problems to tackle them head-on. And our unpredictable interactions with other people and the world at large mean that the path to our goals-and sometimes the goals themselves-will inevitably change. We can learn about our objectives and how to achieve them only through a gradual process of risk taking and discovery-what Kay calls obliquity.” This is fun, big idea book.
  • Do More Faster by Brad Feld and David Cohen (Wiley , Oct 2010) – This is written by two of the founders of startup incubator TechStars. It might be better described as an anthology of writings of startup CEOs, mentors, and other associated with TechStars. This format normally worries me, but in this case the book really works.
  • Gamestorming: A Playbook for Innovators, Rulebreakers, and Changemakers by Dave Gray, Sunni Brown, and James Macanufo (O’Reilly, July 2010) – This book is 70+ tools that can be used in group setting for generating and evaluating new ideas. I have not seen a collection of tools like this all in one spot. For the iteration trend, this is a very tactical book for people who are doing the work.
  • Brilliant, Crazy, Cocky: How the Top 1% of Entrepreneurs Profit from Global Chaos by Sarah Lucy – Lucy is a journalist who has written about technology for BusinessWeek and now the website TechCrunch. In this book, she examines what is going around the world in countries like Israel, China, India, Brazil, Indonesia, and Rwanda and why startups are thriving in these developing regions.
  • Business Model Generation by Alexander Osterwalder and Yves Pigneur (Wiley, July 2010) – This book is being held up by the leaders of the Lean Startup movement as a critical book for formulating business models. This project started as a self-published experiment that has gone on to be commercial published with great success.
  • SuperCrunchers by Ian Ayres (Random House, 2007) – The argument here was using vast sets of data to make decisions is vastly superior to experts. If you have the datasets, regression is the tool of choice as Netflix does when they make recommendations. If you need to generate datasets, randomization or A/B testing fills in the blanks. The book contains straight forward explanations and examples of both methods.
  • Anything You Want by Derek Sivers (Domino Project, June 2011) – Sivers shares 40 lessons he learned through the creation, growth, and sale of CDBaby, a retailer that specializes in selling music for independent musicians.
  • Adapt: Why Success Always Starts with Failure by Tim Harford
  • Culturematic: How Reality TV, John Cheever, a Pie Lab, Julia Child, Fantasy Football . . . Will Help You Create and Execute Breakthrough Ideas by Grant McCracken (my review here)

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