Quitting Google, a surprise pregnancy and what I fear most .... marketing!

Are startups financial suicide? (I'm still trying to decide.)

Ten months ago I quit my job at Google to dive back into startup land. This was actually the second time I quit Google, the first being in 2009 when I left to co-found Shoes of Prey, a custom shoe startup. That business – which raised $25m and generated about ~$10m in annual revenue by the end – ultimately failed after about 10 years.

Post-failure, I wrote an article boldly claiming that “startups are financial suicide”, and then slinked off to work for Google again, much like someone in their late 30s might move back in with their parents.

Me on my last day at Google (August, 2022)

I had another four fantastic years at Google, working in the Next Billion User team as a Product Manager, undertaking field research around the world – India, Indonesia, Mexico, Brazil and Kenya – trying to discover how to best serve new internet users. In the process I was extremely lucky to co-found an experimental Google product, called Task Mate, which allowed people to help Google with micro tasks, for example long-tail language translation, in exchange for payment.

But, as good as the free food was, I eventually missed building new, scrappy things with lots of freedom. I decided to leave again.

Two weeks after quitting Google, my wife realized she was pregnant! A baby is a very happy thing to be sure, but it certainly will put a more solid time horizon on this very self-indulgent adventure I’ve embarked upon.* Worse, I’ve discovered that, while I enjoy the “making” part of startups – or the “arts and crafts” part, as Mihai, my old tech lead on Google Reader would say – I don’t really enjoy the “go to market” (GTM) part. Which, unfortunately, is probably the most important piece! At Shoes of Prey and Google we had many brilliant people to work on GTM. As an Indie Developer, it’s completely on me, but not something I terribly enjoy.

After a few false starts, I’m now working on Mottle – a “build your own” chatbot startup. I’ve got some paid customers, which is great, but there are many problems yet to be solved. And, to be honest, even though I know a lot of the theory, I’m feeling overwhelmed, often by a strong sense of imposter syndrome.

I’ve decided writing these things down might help. We maintained a blog in the early years of Shoes of Prey, and that was massively helpful in terms of getting people’s honest feedback about things, and also just sharing what we’ve learned. I hope to try to recreate that as much as I can. So please join me on this adventure.

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Thanks for reading!

~Mike

* We recently welcomed our daughter Hana into the world. She is an absolute joy!

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