The Art of Failing Well: A Story of Resilience and Growth

Entrepreneurial Pursuits

Growing up, I aspired to become both a tenured university professor and a successful startup founder. However, life had other plans, and I never achieved either goal. I didn't even receive an interview for an academic position, and all six of my attempts to launch startups ended in failure.

Failure #0: Professor Ron

In elementary school, I dreamed of becoming a brain surgeon. However, my surgical aspirations were extinguished in high school biology class when we dissected fetal pigs and I discovered my squeamishness. I traded my surgical scrubs for a computer keyboard and set my sights on AI instead.

In 1991, as a freshly minted PhD, I applied to computer science departments but faced disappointment as the field was entering a downturn and universities were overwhelmed with applications. My lack of publication record and an unconventional conference paper proved insufficient to secure an interview.

Lesson learned: Academic research is not a panacea, and timing plays a crucial role.

Failure #1: FlowNet

During a summer internship at MIT, I collaborated on a hardware design for a computer network called FlowNet. Though our prototype outperformed competition significantly, it faced an insurmountable obstacle: Fast Ethernet was on the horizon.

Lesson learned: Frontal assaults on infrastructure and standards are perilous.

Failure #2: IndieBuyer

After the Google IPO, I embarked on my first entrepreneurial venture: IndieBuyer, an online platform for independent films. Despite a promising idea, our lack of funding and traction forced us to close up shop.

Lesson learned: The movie business presents formidable financial challenges.

Failure #2.5: Evryx

Though I was not a founder of Evryx, a reverse image search company, I became actively involved after being approached to serve as acting CTO. Despite promising technology, internal conflicts and a hostile shareholder vote ultimately led to the company's demise.

Lesson learned: Even smart people can make irrational decisions that have devastating consequences.

Failure #3: iCab

Inspired by the success of Uber, I founded iCab with the intention of developing a ride-sharing app in Saigon. However, our inability to secure a supply chain of drivers rendered the project stillborn.

Lesson learned: A brilliant idea is not enough; execution is paramount.

Failure #4: Virgin Charter (nee Smart Charter)

In 2010, I co-founded Smart Charter, a company that aimed to revolutionize the private jet industry through centralizing demand and automating scheduling. However, a premature acquisition by Virgin, combined with a misunderstanding of market dynamics, ultimately doomed the venture.

Lesson learned: Be cautious about partnering with those who may not fully understand your industry's complexities.

Failure #5: Founder's Forge

Seeking to address credit card fraud, I envisioned a company that would seamlessly integrate transactions and record-keeping using digital signatures. However, after extensive efforts, I faced an impenetrable barrier: the banking industry's staunch resistance to innovation.

Lesson learned: Never underestimate the power of the banking industry to suppress disruptive ideas.

Failure #6: Spark Innovations

My last entrepreneurial attempt sought to create a spreadsheet-like interface with a SQL database back end. Despite signed contracts with three launch customers, they mysteriously backed out without explanation, leaving the company's fate uncertain.

Lessons from a Lifetime of Failures

My journey through six and a half failed startups and one unsuccessful academic career culminated in an unexpected realization: failure, if handled with resilience and introspection, can lead to personal growth and contentment.

Through these experiences, I gained invaluable lessons, developed my character, and ultimately found happiness in the person I had become - one who could confront setbacks, learn from them, and emerge stronger on the other side.