When Things Don’t Go According To Plan: TechCrunch50


Founders need to be agile, able to adjust in real-time as situations develop. You must also develop thick skin (founder armor) and become extremely comfortable with rejection.

One story I have not told before is how Workstreamer was rejected for TechCrunch50 at the last minute. Jason Calacanis himself delivered the bad news But ー getting rejected from the event was only part of the bad news.

It was early days of Workstreamer and our project was being developed by an outsourced development team in India. Admittedly in over our heads, we had been doing everything possible we could to help translate the ideas in our heads into the code being written thousands of miles away. Few people in the world at that time were familiar with the concept of feeds and stream, let alone those living in a culture far removed from platforms like Twitter and FriendFeed.

Collectively we felt that an appearance at TechCrunch50 (THE hot event to launch a product) could be the validation we needed to secure funding. Again, our first call or two had gone very well. Even the demo worked, which was saying a lot at that point.

So we get on the phone with Jason and he breaks the bad news: the team likes us and we’re building the right product. The problem is that a friend called and wants to launch his product, which by the way, is the exact same concept — except much better executed, funded by Founders Fund and founded by one of the all time great founders. Ouch. Yes, it was Yammer, who then went on to win the entire competition.

While it was an extremely hard pill to swallow, I remember getting off that call and wanting to give up. We were devastated. In retrospect, these are defining moments that inevitably happen on the startup journey. You can choose to view them as signs of rejection, that the world is telling you to give up. Or, you can choose to view them as validation that you are working on a very valuable problem and you will need to either level up or adjust other strategy levers.

In the end we did pivot the product and go on to raise money. Timing isn’t everything but it’s a lot, especially in the world of startups. As a founder it’s best to focus on what you can control and remember that you will be tested – all the time – and it’s your job to be flexible enough to navigate the land mines thrown at you.


You might also enjoy:

Thanks for stopping by!

If you’d like to receive occasional updates and new writings from me sign-up below and never miss an update.