Startup lessons from Ben Silbermann, Founder and CEO of Pinterest

As a part of our Summer Fellowship Program, we bring in influential speakers from around the valley each week to share their insights, lessons learned and tips with our teams.  The program has now been in place for six years, so with recent fellowship classes I have been fortunate to pull from our list of alumni when curating the speaker list. One of those alumni, Pinterest CEO Ben Silbermann, was generous enough to join us this past week for lunch with our fellows and alumni from past years.

During lunch, Ben shared details of his background and thoughtfully explained the journey of how he came to be CEO of one of the hottest startups in the consumer internet space.  He also shared a number of insights and lessons which I think we can all learn from:

Hire Great People, regardless of if you have a defined role for them:  Ben shared that one of the things he is thankful he did in the early days was to hire people that he thought were great people even before he knew exactly what their role would be. Great people, he explained, can add value in various roles and often provide key solutions to problems that arise throughout your lifecycle.

Learn from No:  Whether you are seeking funding, making offers to potential employees or trying to build partnerships, as a startup you are going to hear the word no a lot.  What makes Ben a great entrepreneur is that he recognizes that most of the time, people are saying no for a good reason.  He had the patience, self-awareness and intellectual honesty to evaluate the situation and make the necessary changes.  Whatever the reason for No, Ben stressed the importance of using it as opportunity to learn and to correct so that you are moving your company into a position where you can start getting some yeses.

Decide what will make you happy and commit 100% to doing it:  One of the things Ben said he learned early on was that while being an entrepreneur meant that he had control over what he was building and doing, it also meant that he lost control over a number of things like a steady paycheck or the resources of a large organization.  But, ultimately, the tradeoff was worth it for him to keep going.  His advice to the group may seem simple and obvious, but it can be hard to follow!  He was convincing – you have to find what makes you happy, because ultimately, that is the person you have to answer to first.  Building a startup is really hard, but if you are doing something you love or building a product you are passionate about, it is one of life’s greatest rewards.

Foster your co-founder relationships:  Like any relationship, you are going to have some ups and downs as founders so it’s important to foster a good, highly communicative relationship with your co-founder(s) so that you can make it through those rocky days. Again, it may seem fairly straightforward, but it is one of those things that requires consistent attention and can make all the difference.

Recognize what you don’t know and tackle it head on: This was less of a tip and more of an anecdote that Ben shared, but one that I thought was worth mentioning.  Every weekend, he reads a different business book in an effort to hone his business, marketing or technical skills.  Having a ready appetite to learn and grow as a person and a leader is no doubt a part of Pinterest’s secret sauce and something I encourage any entrepreneur to foster throughout their careers.

It was tremendous to have so many alumni back at Lightspeed and thanks again Ben for your time and thoughts.

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