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Why my first startup in the Valley flopped

On May 1, 2011, I exchanged stability for variability: I quit my job at Zynga and began the journey of building a product and a company…

Why my first startup in the Valley flopped


On May 1, 2011, I exchanged stability for variability: I quit my job at Zynga and began the journey of building a product and a company with my good friend Ben Bloch. We had good momentum and an excellent support team. We took a small friends-and-family round and began crafting a new communication tool that would enable close friends to quickly meet up. Our first iteration of Whim was complete in approximately four months, and we began distributing it to some of our close friends. We soon identified certain flaws in the product, by listening to our beta users and observing how the service was being used. The second version was a big improvement but still wasn't there. We were convinced we nailed it on our third iteration, but ultimately we never achieved any type of product market fit. Everyone knows startups are hard, but not everyone experiences the hardships. In an attempt to keep it short and sweet, I'll identify four key factors that led to our demise.

Identifying a problem vs. fabricating one

Were people really in need of a new way to gather? Did the existing tools suck as much as we thought they did? We greatly underestimated these questions and naively assumed that there should be a better way to get close friends together. The reason Instagram became so popular and achieved the level of adoption it did was that it identified real problems in the mobile photo sharing space and tackled them head on. This delighted users because they were used to such a poor prior experience. Consumer applications that do this are golden. I am still not convinced that any of our competitors such as Ditto, and GlassMaps will break through and gain mass adoption because of one simple fact: They are all trying to modify human behavior, and if your offering isn't 100 times better than the current solutions, then you are going to fail.

Changing consumer behavior

Simply put, we were trying to replace SMS, email, and phone communication. These were our biggest competitors, not the plethora of other services that tried to compete with ours. I am not saying that services should not attempt behavior modification, but if they do, they have to make people feel like their product is something they could not live without prior to its existence. It has to be magical. We were trying to convince people to first, download an app, and then use it over their built-in communication tools. We had some nifty features, such as location tracking, user presence, and proximity-based friend notifications, but these were not enough to retain users and change their mindset. We saw a lot of people give us a shot and then immediately drop off after their friends did not use the application, or they became annoyed by getting yet another set of notifications that didn't add much value.

Delaying the inevitable

We should have identified that our service was not adding much value and moved on six months in and not waited a year to cut our losses. This would have given us six months of runway to think up something else and give that a shot. By the time we came up with another idea, we were at the end of our funding cycle. Raising more money and going in for round two of the fight was not something Ben and I took lightly. Do we struggle trying to bring another product to market while living together in a one-bedroom apartment on a tight budget? Or do we step away, do something else, and give it another shot when the time is right? Ultimately, we chose the latter because we didn't believe as strongly in the new idea we came up with. If it were something we absolutely wanted to try then the outcome might have been different.

Not incubating

Over-confidence is dangerous. Ben and I were convinced we could go at this process alone and bypassed applying to YCombinator or 500 startups. We truly thought that we knew enough of the right people to get things rolling. I quickly learned that unless your product has mass appeal and traction, or you are Kevin Rose, high-profile angels are not going to throw money at you. Therefore we needed to seed ourselves with credibility. The network and credibility that a team gets when they are part of a good incubator is priceless and well worth the equity loss. We ended up applying to YC at a later stage and got an interview but didn't get in. If we had gone through several products and applied multiple times, our chances of getting in would have been higher — and who knows if I'd be writing this blog post today.

All in all, this was a great experience. I learned so much, and the outcome was favorable for both us and our early investors. I have no regrets and would do it all over again in a heartbeat. I ended up joining a great crew at WillCall, where we are trying to redefine the way people experience live music. I am very passionate about it, and I am in early enough to be impactful and have a stake in the success of the company. I couldn't ask to be part of a better group of people and wake up everyday with a huge smile on my face, because I know we have the opportunity to make a huge impact and flip an entire industry on its head.

My message to everyone who is thinking of taking the leap is to go balls out and never be afraid to fail. The biggest failure in my book is not trying to pursue your dreams. Now get out there and live your dreams!