Leaving my startup to join Dropbox

This will come as a surprise to many of my friends who don’t already know. I am leaving Padlet and joning Dropbox starting July.

After months of giving Padlet a shot, my co-founder and I realized that we’re just not meant to be business partners.

We were very close friends. We often talked about what the world should look like and how we could , together, make something that people wanted. We always thought we’d end up starting a company together.

However, the fact was that we had come from two very different worlds. Although we are both engineers, and had briefly worked together in college on small projects, our experiences since college had been vastly different.

He had joined a startup straight after undergrad and been an engineer throughout. I had gone into management consulting, and then dabbled in product and corporate strategy. He had learnt how to build world class products and features, and I had learnt how to develop the right strategies to take products to market and to build operations. He had mostly been an individual contributor and I had worked with teams, small and large. I had taken a keen interest in business skills and he despised the term “business”.

However, for some reason, we had always wanted to work together on a company. We just figured we are good people and friends. We’ll be fine.

We realized later. That was very short-term thinking. Long story short, our friendship was not strong enough to weather the ups and downs of start-up life, and without a formal  structure to the partnership, something had to give. We were just way too different in the way we thought about building a company.

Mutually, it was decided that I leave the company. So, I did.

I have since joined the Business Operations team at Dropbox. Its a fantastic opportunity to take a very successful business even farther and revolutionize the way people work. I am really excited about this phase of life! More on this in the days to come.

Even though 6 months is not a long time for a startup co-founder, I did learn a lot of valuable lessons, some of which are included below. I would strongly urge you to also read this awesome post by Harj Taggar, and this one by Naval, about the same issue of co-founders.

Dividing roles and setting expectations.

Startup founders get lots of mixed advice on this topic. Some advisers will tell you to not divide roles early on. Its too early to divide roles. Each co-founder should be helping out in whichever way needed at that stage of the company. Others will often say that you need complimentary skill sets. If one is the tech wizard, try and find a co-founder that has business experience.

My experience is slightly different. There is no right or wrong answer to this, but if you have never worked together before (even if you have been friends), be completely open and honest about how you perceive your and the other co-founder’s skills. Of course they are great people. That’s the bare minimum to form a partnership. Talk about the hard and soft skills each brings to the table and use that as a way to gauge roles that would be fit for each.

If each founder doesn’t feel that the other is pulling their weight or that they themselves aren’t contributing enough value, its time to talk about roles and expectations.

Open and brutal communication

I had written a post about communication for startup co-founders back in March. I guess it was about the time we started seeing the cracks in our business relationship. However, by the time we started talking about it, we had built up enough resentment and distrust. It was difficult to have a productive conversation and see a way out, without it getting too personal.

We both tried, and we both failed. I guess, we were just too late. Harj says it best in his post –

Sometimes I’ll see a team acrimoniously break-up one day over a seemingly trivial thing, despite having seemed calm and fine for months. It almost always turns out there was some simmering ongoing issue that neither founder brought up.

Well, I hope this helps some others out there. I continue to be an avid supporter of Padlet and hope that it goes on to achieve further successes.

As for what’s next for me – Dropbox, here I come!

  • Onward and upward!

  • Baptiste Picard

    Lively and intense journey! All the best for your new adventure at Dropbox :)

    • thanks Baptiste! hope all is well on your end?

      • Baptiste Picard

        Yes all fine! I won’t have the opportunity to pass by the energizing area of San Francisco this year unfortunately but will discover a country I’ve never been before: India :) So quite excited!