An Entrepreneurial Workshop

My wife aptly calls my latest side gig, a dream job. It involves mentoring a group of National University of Singapore students who choose to reside in Silicon Valley for a year. Part of the program involved me conducting a workshop on entrepreneurship.

I wanted to start the session with a personal story and a little humble bragging, so I told this tale:

This T-Shirt was made in 1999. Like all great Silicon Valley companies, the first thing we did when we raised $5 million, was to get a T-shirt made.

In 1998, when I started the company, ecommerce was like what AI is like today. It was the future, the next big thing. And of course, Amazon was the media darling even in its infancy then. They were still mainly selling books and maybe just starting to move towards CDs and DVDs. In fact, hardly anyone shopped online at the time. Way less than 1% of all goods were sold through websites.

At the time, I thought the more use case of online shopping was to use the internet to research what you want to buy, but then go to your usual brick and mortar stores and to make the actual purchase - “Look Online, Buy Offline”.

Venture capitalists are a bunch of lemmings and in 1998, they were all marching towards the ecommerce cliff. I needed a way to get my contrarian point across. So, I told my prospective investors: Amazon may be the longest or most famous river. But it’s a lonely river. It's definitely not where the people are. The most populous river is Ganges (half a billion souls, more than 10x Amazon). And that’s why we are Project Ganges, a site that folks go online to buy offline.

It’s 2025, and Amazon is one of the biggest companies in the world while my startup died, so I was clearly wrong. But telling the story of the two rivers Amazon and Ganges helped vividly illustrate a contrarian path. It got my company its first $5 million and my name on the front page of the Wall Street Journal.

Looking back, I realized how using the metaphor of the two rivers made my startup pitch more memorable than any b-school 2x2 framework could do. My students were preparing for their own startup pitches, and I wanted them to avoid the same insipid powerpoint presentations that we’ve all seen a million times and instead, be inspired to tell their own stories in their own voices.

I wanted to avoid boring my students for the rest of my workshop. I figured instead of a lecture of all my hard-found “wisdom”, they should try to figure out how to incorporate entrepreneurial principles into their own startups. After all, this was meant to be a practical workshop.

I had a germ of an idea after lamenting that in our current craze for always pursuing the current thing, we’d forgotten the OG lessons that were being formed and distilled during the time when I was struggling to do my own startups. Seminal concepts such as crossing the chasm in the technology adoption cycle, how to avoid bigger competitors early on that you ultimately want to disrupt and how to validate the core premise of your own company. I wanted them to learn the nuances of these lessons contextualized within their own startup ideas.

With the advent of AIs, I thought maybe students could reacquaint themselves with 3 seminal books of my generation by chatting with LLMs as their study partners. And so, a week before the workshop, I started a chain of messages (click on the screenshots if you’d like to follow along too!):

Taking inspiration from the Jeff Bezos meeting technique, I gave the students the first hour to read on their own and figure out how to apply the lessons of the books to their own startup, and then craft a short story or anecdote. In the second hour, they would each share their story and we would all reflect and help improve on it.

In battle, no plan survives contact with the enemy. And so it is with startups – and with conducting workshops! I had preconceived notions in my head of how successful the workshop could be. In my head, I was this brilliant orator, inspiring all the kids. In the actual event, I felt awkward and self-conscious.

When I went my rounds interacting with the students, I was often met with earnest but puzzled looks. I realized the gulf of things I wanted to impart and the need to break things down to more digestible bits. I had committed the oft-made mistake of trying to cram too much in a two-ish hour session.

I was skeptical initially when a group of students experimented with cloning their voices in the hope of always being able to comfort their ailing grandparents suffering from dementia even when they were not available. But their infectious, earnest enthusiasm and excitement over their proof of concept won me over.

I was totally psyched when another group told the stories of 3 patients whose lives would be drastically different with stem cell therapies. But the costs of procuring such stem cells were prohibitive. Their startup aimed to change that by harvesting stem cells from menstrual blood, which like the best ideas seem so obvious only in retrospect. I loved how they crafted and told their story.

I really enjoyed interacting with the students and helping them find the core of their idea that they can build upon. Reflecting back, In the future, I may trim it down to just one startup concept to try to dissect and apply. I have my bias for Clayton Christensen’s “Sword and the Shield”.

I can see why my wife describes my entrepreneurial mentor role as a dream job. It is energizing to interact with the next generation of entrepreneurs. It’s almost like getting a glimpse into the future. I have thought deeper as to what is the essence of a successful startup. Unlike most ventures, almost by definition, a successful startup is one that didn’t exist before. How do you come up with rules and principles for creating something that no one has had prior experience of? That is the challenge and I'm still an ardent student. This workshop made me a better entrepreneur

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If you have read this far, and found my writing pretty disjointed. First, thank you for reading this far. Second, you’re absolutely right - this was the unanimous feedback I received in my writing gym. And yet, I’m leaving the piece as such, because I want to hold on to this feeling of discomfort. It’s the closest feeling I have whenever I’m stuck in a new venture and not really seeing much success. Will I be able to power through and emerge victorious with a polished piece that feels right every which way you look? I’m not sure - that’s probably the source of a lot of the discomfort

But I want to leave you on a happy note. So speaking of something who has pushed through and is absolutely killing it, do check out Andrew Chen’s recent posts. I love how he extends the Idea maze to the Growth maze. The subsequent piece then examines how startups navigating this idea maze as a whole will affect the entire entertainment industry. Genius!

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Thank you

Rick Lewis

,

Marie Friberger

,

Emily Ann Hill

,

Simon Emslie

,

dxh

and

Louie Bacaj

for your much appreciated feedback, support and helping me “be less independent”!