A MIT graduate on 3 things he learned when his first startup failed

Photo credit: Luke Pamer

Getting a good education is the recipe to a good job and a good life. That’s what I heard as a kid growing up in Hong Kong.

After 30+ years:

• I hold 3 degrees from MIT and University of Waterloo (whose students, as Paul Graham said, were better than any universities)
• Worked in management consulting, large corporations and startups that got acquired.

Yet, none of it prepared me for being a co-founder.

I had a great time in Yahoo, managing a team of over 20 staff and being responsible for tens of millions of dollars in revenue across the region, but I was tired of the corporate life. An opportunity came by and I became a co-founder, together with a fellow MIT alumni. It was my co-founder’s idea, but since I did not know how to build software, I took on the role of “everything else”: partnership director, community manager, content marketer, etc.

With two MIT alum whose resumes included brand names such as Bain & Company, IBM, Morgan Stanley, Yahoo!, one would think that we have a better than average shot. Unfortunately, the venture did not last even a year, and here are 3 things that I learned from being a first time co-founder. I hope they will be of use to you.

1. Understand the technology you are building  

I was lost. All the education and work experiences did not prepare me in tackling the day to day of building a startup.

When I was an employee, I had very specific tasks and scope. As a founder, I had to make decisions on what needs to be done, and that’s not always clear. I was a trained engineer – a semiconductor designer. I did not understand anything about web software or the technology and product development process used in startups. As a co-founder, you need to have background knowledge of these technology and methods. Without them, you can’t make informed decisions and add value to your team. When issues arise and the schedule was delayed, I could only ask why, but not offer a practical suggestions or solution. It resulted in tension between my development team, my co-founder, and myself.

I now understand that the early days of starting a startup is very different, compared to already having a team of 10+ people. There are specific skills and processes that founders should know when building the early foundations of the company – when you are taking it from 0 to 1.

2. Have the tough discussions early

We incorporated the company based on a 50-50 equity set-up. We did not have titles as we didn’t think it mattered. The truth was, we were avoiding the talk. We wanted each other to feel equal and be “in it together”, but I now understand that this is the worst set up between founders. It simply means no one is in charge.

We also did not spend sufficient time talking about our motives and vision for the company. All that avoidance only made things worse when we were facing other issues down the line.

3. Your startup has to be your life mission 

The last and most valuable lesson I have learnt – your startup has to be your life mission. Our startup was in the fashion and lifestyle space. At that time, there was a new trend in the fashion ecommerce space: content driving commerce. Startups such as Polyvore, Refinery29 and Meilishuo (China) were making TechCrunch headlines and doing well. Fashion was hot! We figured that we can combine my cofounder’s technical ability and interest in fashion, with my experiences in affiliate marketing and advertising to build a great company, potentially selling to other media companies, even Yahoo!. It was a match made in heaven – a market opportunity and a complementary skill set.

Soon, I spent my day and night talking to fashion bloggers and brands. I was attending local “fashion summit” and meetup groups, trying to impress the community and get them on our platform. My “interest” quickly turned into dread. I dreaded having to dress to impress, to memorise the nuances of Alexander Wang’s spring collection. I dreaded that I had to pretend that I am passionate about fashion.