A Beautiful Failure

Taylor Stockdale
While on a plane this fall, I was skimming CNN’s Money when I came across a story entitled “Hosain Rahman’s Beautiful Failure.” The headline grabbed me. Earlier that day, I had had a conversation with the Freshman Dean at Harvard about the essential qualities needed to succeed in our nation’s most selective colleges and universities. Resiliency, inner strength and moral courage were three of the top characteristics mentioned. It got me to thinking.

In this age of zealous parenting (I can say this because I am as guilty as anyone), when we give out trophies for just about everything, I wonder if we are teaching our children how to fail and pick themselves back up? Are we teaching students to be resilient and determined? And most importantly, are we inspiring them to have the moral courage to do the right thing when it counts the most?

But the CNN story caught my attention for more than just the headline about failure. As I began to read it, I soon realized that Hosain is a Webb alumnus – someone I knew well back in the early 1990’s and a graduate of the class of 1993.
You can imagine my deep sense of pride as I read about Hosain’s bold move, which saved his highly successful company. If my premise is right – that the true measurement of a school’s success is found in its alumni – then Hosain’s story is yet another testament to Webb.

After graduating from Webb and then Stanford with a degree in mechanical engineering, Hosain went on to start a tech company called Jawbone – a highly successful Silicon Valley company which initially specialized in hi-tech headsets.
While at Webb, I remember Hosain as a tall, lanky affable kid with a wonderful smile, a quick wit and engaging personality. He always lit up the dining hall, the library, the chapel, or the pool deck when he entered. I smiled when he was described in this article by venture capitalist Ben Horowitz as “a relationship person, the sort of social savvy, influential connector described in Malcolm Gladwell’s The Tipping Point.” But Hosain is so much more than this. At Webb, he was known for his fierce commitment to honor, his strong work ethic, his sharp mind and creative mindset.

As Hosain and his business partner grew Jawbone, they revolutionized the wireless headset industry, and then ventured into other products, including the Jambox and the UP bracelet. The UP bracelet is a game-changer in the area of personal health and health monitoring. It is a hi-tech bracelet and app that monitors your movements, intakes and sleep, and then provides information for making positive changes to your routines to improve your health.

In November of 2011, Hosain and Jawbone released the UP bracelet in time for the Black Friday sales. As the story is told, UP soon came under criticism from its many customers. For some reason, the bracelet was not transmitting the information properly and was shutting down. Hosain and his employees were distraught. Jawbone, still a fairly new company, had only released a few products in its history. And with the online communities buzzing with how poorly the UP Bracelet was functioning, Jawbone was in a dire position. In the heat of the moment, when everything looked grim, Hosain, hunkered down, developed what he called a War Room at his Silicon Valley headquarters, and with his entire company went into crisis mode in an effort to find out what was wrong with the device and fix it as soon as possible.

During these times of despair, Hosain is described as being strong, vigilant, clear minded and focused despite severe sleep deprivation and around-the-clock attention on this high-pressure, critical situation. As CNN outlines, it was in the heat of the battle one night that Hosain decided to write a letter to his customers, investors, and other stakeholders. But it wasn’t the usual defensive letter of faint apology and vague generalizations on the prognosis of the product in the future. Rather, it represented a sharp contrast to anything that had been written up to this time. It was honest, direct, and complete.

Hosain took full responsibility for the mishap, and offered all customers their money back, regardless of whether they returned the product. “We are so committed to this product that we’re offering you the option of using it for free.” What turned out to be a technical problem with the circuits, was a watershed moment for Hosain and for his company. The UP bracelet and Jawbone are absolutely thriving today, but that letter is now cited as having saved the company. The response from the Silicon Valley toward Hosain and Jawbone was one of total respect. At the epicenter of the hi-tech universe, it was an old-fashion, honest, straight forward, well written letter which had the greatest impact of all.

Failure, as we all know, is inevitable. And great leaders fail often. The goal of a great education shouldn’t be about teaching students how to prevent failure. Rather, it should be about how best to respond when failure occurs. Hosain, in the heat of the battle, chose to think boldly and creatively, act with honor and moral courage, and to lead with distinction through the crisis. He saved his company and his employees jobs as a result. The Webb mission in action, again.

In the last issue of Webb, I made a plea not to use rankings to determine the quality of a school or a college. Rather, the best measurement of success is to look at the end product – the alumni. And by that I don’t mean the wealth of the alumni, but the lives they choose to lead and the decisions they make when times are tough. The alumni of a school or college tell the real story.

As you read this issue of Webb, I hope you enjoy the many stories and examples of this extraordinary education in action today, and the many alumni who embody our values so well. The story on genetics highlights the importance of developing both creative thinking and moral courage in an increasingly complicated world. Our feature on women’s colleges underscores the effectiveness and importance of our unique two-schools-on-one campus framework for honoring the formative differences of boys and girls in meaningful ways. And the remarkable photo essay on the chapel that reminds us all of our spiritual core as a school community as we all work hard so that our students will have the fortitude to meet failure head on and do their school proud.

Read More News

Alumni News

List of 4 news stories.


Webb News

List of 4 news stories.

  • Lifelong Learning: The Third Education Revolution

    In this fascinating article in The Atlantic, writer Jeffrey Selingo dives into the argument many economists, educators, and work-force development professionals are making today--our education in early life does not seem sufficient for the needs of our 21st century economy. The third wave, as he describes, will be one of continual training and education and retraining. Read more in The Atlantic.
    Read More
  • Alumni Events April 2018: New York, Philadelphia & London

    Alumni, family and friends are invited to join Head of Schools Taylor Stockdale and special guests for three events this April in New York City (April 11), Philadelphia (April 12) and London, England (April 14).
    Read More
  • Winter Sports Round-Up & Honors 2018

    Once again, Webb athletes had a strong showing across the board during the 2018 winter season. Led by WSC soccer, which finished the season League Champions and with a deep run into CIF, both VWS and WSC athletics posted very positive results. VWS Water Polo also finished its league play in second place.
    “It is always great each season to not only see our athletes and teams be successful on the field of play, but to see them learn and grow as individuals and part of a community,” said Director of Athletics Steve Wishek.
    Read More
  • VWS Dean of Students Sarah Lantz holds a portrait of Vivian Webb

    Women of Webb Around the World

    In honor of International Women's Day, the Alumni Office recognizes the Vivian Webb School's 1,355 alumnae around the globe.
    Read More

Sports Blog

List of 4 news stories.

The Webb Schools Boarding Preparatory School California Private School Financial Aid Paleontology College Placement Top Academics Faculty Ph.D Community Fun