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A startup story – Notes from “Founders at Work- Hotmail”

I’ve been reading the book “Founders at Work” – Stories of Startups’ Early Days by Jessica Livingston to get a better idea of how some well known startups came about and to (hopefully) gain some inspiration from the interviews with their founders.

The Hotmail story was particularly interesting:

Interestingly, enough Sabeer said earlier this year about cryptocurrencies:

“the dotcom bubble had companies with viable business models, as opposed to cryptocurrency-related projects which he believes don’t. He added that ideas which have not been implemented should not be valued at billions of dollars.”

I tend to agree with Sabeer. While companies were overvalued during the dot com bubble, they often did have millions of users and were onboarding users at an exponential rate. The same rate of adoption hasn’t really been seen in the cryptocurrency markets yet, leading me to believe that we are perhaps either:

Anyway, I digress.

On founders

I find the relationships between cofounders to be particularly important. A startup at the end of the day depends heavily upon the relationship between the founding team and it has been increasingly the case that there are typically two co-founders for some of the most successful startups.

Points that stood out to me:

On the startup idea

People like to think startups have this incredible idea right off the bat and they just pursued that, leading to an eventual exit or a billion dollar series B round. It typically doesn’t seem to be the case that startups even stick with the original idea. However, the basic tools being built out or the lessons learned initially are usually used in the final product. Apart from that, every startup seems to have a separate story about how they arrived at their final form.

With hotmail, the story progressed as follows:

Lessons:

There are more of these lessons peppered throughout the book, but luck and timing seem to play a far bigger role in the success of most companies than founders (and their investors) would like to admit. Practically no one uses hotmail now and today, Microsoft’s email market share is at <10%. Sabeer and Jack were unable to recreate their success with hotmail in their succeeding ventures.

This short 2 year story reminds me that starting a company is best viewed as an asymmetric bet with a fat-tail, with the main constraint being time (If we could make infinite independent bets, many flawed strategies in real life would work well). Having a longer term view allows many dependent smaller bets to be made within the scope of a single larger bet (one company), and improve its probability of success. But nothing quite beats timing and following the trend.

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