From Failure to Success: The Unlikely Journey of a Tech Entrepreneur

speaker1

Welcome to our podcast, where we dive deep into the world of tech and entrepreneurship. I'm [Your Name], and today, we're on a unique journey to explore the highs and lows of a tech entrepreneur who has faced numerous failures but emerged wiser and more resilient. Buckle up, because this is going to be an exciting ride!

speaker2

Hi, I'm [Your Name]! I'm so excited to be here today. So, let's start at the beginning. How did you first get into tech, and what were your early ambitions?

speaker1

Great question! Growing up, I had two major life ambitions: to become a tenured university professor and to found a successful startup company. My role models were people like Rodney Brooks, who made a big splash in the AI/Robotics world in the early 1990s. I originally wanted to be a brain surgeon, but my high school biology class with fetal pig dissections revealed I was more squeamish than I thought. So, I traded my surgical scrubs for a computer keyboard and set my sights on AI.

speaker2

That's an interesting journey! What challenges did you face when you started pursuing your Ph.D. in AI during the AI winter?

speaker1

Oh, the AI winter was a tough time. It was the early 1990s, and the field was in a bit of a slump. I sent out my CV to CS departments, but the timing couldn't have been worse. Universities were getting hundreds of applications for single openings, and my publication record wasn't strong enough. I didn't even get an interview. So, I stayed at JPL, where I had been working, and my career there had its ups and downs. Eventually, I realized that scientific research was not what I had imagined. It's a deeply human endeavor, intertwined with ambitions and foibles. I learned how to work the system, but I became less proud of the work I was doing, and the entire field seemed mired in stasis. So, I quit.

speaker2

That's a powerful realization. Moving on, you mentioned a project called FlowNet. Can you tell us more about it and what happened?

speaker1

Sure! FlowNet was a project I worked on during my time at MIT with Rodney Brooks. We had this brilliant idea for a new computer network design that would have been more than an order of magnitude better in price-performance than the competition. We built working prototypes, and we had meetings with VCs, but none of them gave us a term sheet. Fast Ethernet was coming, and although it would be expensive at first, it would quickly get commodified and beat out any potential competition. We built our prototypes in 1993, Fast Ethernet came out in 1995, and we folded up the tent in 1997. The lesson learned is that direct frontal assaults on infrastructure and standards are very unlikely to succeed.

speaker2

That's a tough lesson to learn. But you did have a stint at Google, right? How did that go?

speaker1

Yes, I joined Google in 2000. It was an interesting experience. On a personal level, I count it as a failure. My tenure there was marked by a series of screwups, and I had a serious case of impostor syndrome. I lasted a year and then went back to JPL. The IPO allowed me to pursue my entrepreneurial ambitions more seriously, but it also taught me that even success can come with its own set of challenges.

speaker2

That's a really honest reflection. Let's talk about IndieBuyer. What was the idea behind it, and what happened?

speaker1

IndieBuyer was my attempt to do something in the entertainment space. The idea was to be Netflix for independent films. We would sell DVDs with a money-back guarantee, and the returns would provide data for a recommendation engine. The long-term goal was to intelligently match niche products with niche audiences. It was a plausible idea, but I was funding it entirely from my own pocket, and after a couple of years with very little growth, I lost my nerve and decided to pull the plug. We couldn't attract any outside investors because we had already launched and weren't showing much traction. The lesson learned is that it's really hard to make money in the movie business.

speaker2

That sounds like a challenging but valuable experience. What about Evryx? Can you tell us about that one?

speaker1

Evryx was a bit of a half-failure. It was an early pioneer in reverse image search. The company used an algorithm called SIFT to match an image taken with a cell phone to a library of stored images and provide information about whatever was in the image. I was involved, but not a founder. The company had a crisis when the founder/CTO was behaving erratically, and my friend, the CEO, had to fire him. I came aboard as acting CTO, but the company ultimately folded in 2007 due to the financial crisis. The lesson learned is that even smart people can do incredibly stupid things. The CTO, for example, voted against the financing because he didn't want to be diluted, which ended up making his intact share of the company worthless.

speaker2

Wow, that's a wild story! Moving on, how about iCab? What was the idea, and how did it compare to Uber?

speaker1

iCab was a brilliant idea, but it was stillborn. I was in Saigon on a cruise, and I thought, 'Why isn't there an app to connect people with taxi drivers?' I founded iCab, and we built a prototype app. But we couldn't figure out how to procure drivers. We tried pitching the idea to cab companies in LA, but they weren't interested. Meanwhile, Garrett Camp and Travis Kalanick had the same idea and founded Uber. The lesson learned is that a brilliant idea is not enough; you have to execute. And sometimes that requires another brilliant idea.

speaker2

That's a great lesson. What about Virgin Charter? That sounds like a big project.

speaker1

Virgin Charter was a billion-dollar idea. The private jet market is incredibly fragmented and inefficient. I came up with a plan to build a centralized clearing house for demand, which would route the fleet much more efficiently. The plan was to offer a lead generation service to brokers, then to operators, and finally, a centralized scheduling service to minimize empty legs. It was a brilliant plan, but my co-founders decided to sell the company to Richard Branson before we launched. They changed the business model to be directly consumer-facing, which was a mistake. The market is very rarified, and treating customers like ordinary consumers didn't work. The lesson learned is to be careful who you take on as a partner. Success in one industry doesn't necessarily translate to success in another.

speaker2

That's a tough lesson, but an important one. What about Founder's Forge? What was the idea behind it?

speaker1

Founder's Forge was an attempt to solve credit card fraud. I saw the potential in using digital signatures for e-commerce. The problem is that the credit card protocol is fundamentally broken, and the credentials can be reused. I came up with a plan to hide the fact that I was trying to solve credit card fraud by presenting it as a different product addressing a different problem. The idea was to provide a service that coupled transactions and record-keeping to guarantee they always remained in sync. But I needed a bank to move money around, and the banks turned out to be an impenetrable brick wall. They all initially showed interest but then backed off without explanation. The lesson learned is never to underestimate the capacity of the banking industry to stifle innovation.

speaker2

That's a fascinating and frustrating story. Finally, what about Spark Innovations? What was the idea, and what happened?

speaker1

Spark Innovations was a product motivated by the observation that people use Microsoft Excel for purposes it was never intended to serve. We built a product with a spreadsheet-like UI but with a SQL database on the back end. We had three launch customers lined up, but they all suddenly lost interest and didn't tell us why. It was a similar situation to the banks. My partner had to quit because he needed a paycheck, and I tried to pivot the company, but it didn't work. The lesson learned is that sometimes, despite your best efforts, things just don't come together.

speaker2

That's a powerful journey. Despite all these failures, you've come out the other side wiser and more resilient. What's the biggest takeaway from all these experiences?

speaker1

The biggest takeaway is that failure is not the end. It's a learning opportunity. Each failure taught me valuable lessons, and those lessons have made me a better entrepreneur and a better person. I've learned to be more adaptable, to question assumptions, and to be more strategic in my approach. And, of course, hitting the jackpot with Google didn't hurt, but I really believe that my current happiness comes from the person I've become through these experiences.

speaker2

That's an inspiring message. Thank you so much for sharing your journey with us today. It's been a pleasure chatting with you.

speaker1

Thanks for having me! I hope our listeners found this conversation as valuable and engaging as we did. Until next time, keep failing, keep learning, and keep growing!