Author: Greg Wymer

by Chris Keshian MBA ’22, MIT delta v Program Manager

The Martin Trust Center recently presented an 8-part “Antifragile Speaker Series” in response to the COVID-19 crisis. This is the first in a series of blog posts that are meant to shed some light on what it means to be antifragile, and why it so important for entrepreneurs.

In his 2007 book, The Black Swan, author Nassim Taleb describes a world shaped by rare, unpredictable, outlier events. Antifragile is his 2012 response to Black Swan, in which Taleb proposes a theory on how to deal with such an uncertain world. Rather than attempting to predict the unpredictable, he proposes building systems that are antifragile because “fragility can be measured; risk is not measurable.”


  • Things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty.
  • Anything that has more upside than downside from random events (or certain shocks).

So how can this be applied to entrepreneurship?

While each specific entrepreneurial journey requires different skills and competencies, one thing they all share is the need to operate under uncertainty and ambiguity. Succeeding and staying sane throughout the chaotic entrepreneurial process necessitates an antifragile mindset –- one that improves as a result of this volatility.

No matter how much you prepare, it is impossible to account for all the externalities that may affect your fledgling company (i.e., you will never be able to accurately measure risk). Over the past six years, through many failures, I have learned to apply the concept of antifragility to my own mental and emotional roller coaster that results from these externalities. As a result, I have been better equipped to deal with the setbacks I have encountered.

Four antifragile principles have allowed me to learn and grow through these difficulties.

1) Maintain a bias toward learning and personal growth, instead of financial success.

  • keep a growth mindset
  • become an organism that learns and grows regardless of the situation (good, bad, or ugly)
  • shift your metric of “success” from the amount of money made to the amount of learning and growth you undergo

2) Keep your eyes open when you’re getting punched in the face.

  • stay AWAKE and AWARE during the difficult times
  • channel and embrace the discomfort of the experience, then figure out what to learn from this

3) Develop the ability to flow with randomness.

  • cultivate and maintain internal peace
  • accept a perspective of the universe as a force that is conspiring to provide a learning experience through each situation

4) Follow an approximate direction, not a detailed roadmap.

  • court optionality and serendipity
  • have a system rather than a goal
  • treat each obstacle as a potential new path forward
  • maintain a sense of open-minded optimism

In this series of blog posts, I will more deeply define these principles, and reference some applicable insights from Nassim Taleb, Carol Dweck, Viktor Frankl, Mihaly Csikszentmihalyi, Marcus Aurelius, and Scott Adams. I hope you enjoy reading and take something away that you can apply to your own mindset.

This is the first in a series of five posts. Read the others here: