In response to the article on the Entrepreneurial Generation, I’ve been discussing with friends a specific part:

AND that, I think, is the real meaning of the Millennial affect — which is, like the entrepreneurial ideal, essentially everyone’s now. Today’s polite, pleasant personality is, above all, a commercial personality. It is the salesman’s smile and hearty handshake, because the customer is always right and you should always keep the customer happy. If you want to get ahead, said Benjamin Franklin, the original business guru, make yourself pleasing to others.

It has made me wonder whether it makes sense to try not offending people with strong positions and opinions. Do nice guys get ahead by not taking a position?

I’ve often not ventured a strong opinion as it’s rare to find a situation without a lot of nuance and oftentimes in discussions I have nothing to gain by being offensive. It’s far easier to state the sides than take a side. In fact, I’m never forced to take a strong position unless I’m making a decision for business. I’m beginning to rethink this general approach and in fact embrace the idea of taking only strong positions in anything I elect to opine or make a decision on. I’m inspired by something incredibly insightful and powerful that one friend wrote back to me:

Strong opinions are important because you need to believe in something to guide your decisions in order to accomplish anything. It’s the difference between being an author and a book reviewer. The author has to decide what is important and what should be cut and what the point of the book is.  Every word that is in the book is there because the author decided it should be there.  The book reviewer can read a book and comment on the decisions that were made by the author, but he will never be able to write a book because he can not make the important decisions, he can only comment on the decisions others have made.  Being well rounded and understanding that both sides of an argument have pros and cons is easy.  Its moving past that and making a decision that is hard. As an entrepreneur by definition you can’t be content to accept both sides of the coin and sit idly by.  You have to consider both, and then fully commit to one.  Strong opinions lead to vision, because only when you have made a decision about what is important and what is right can you start to see how the future should be.

After PaperG took on investors a number of years ago, I realized we needed to begin communicating with a new group of people who cared about the future of the company. Before, we just had our founders and our customers which made it pretty easy to figure out what to share and what not to share with who or who not. Soon, we would have many more employees, advisers, and other supporters which would all want to know what’s going on with the company.

Wondering what other founders did in this situation, I stumbled upon an interesting solution by Larry Page and Sergin Brin. They wrote Founders’ Letters since the time of their IPO. Going through them gives you a glimpse into the minds at work behind the impressive growth of Google. They don’t go into the blocking and tackling of day to day operations nor all the money they were making for their shareholders. Instead, they focus on the progress and vision for the company. These letters also always end with the name and signature of the founders.

           

I admired this approach. It was a simple and easy way for the founders to directly communicate with everyone who cared about what they created. So often the voices of the founders get drowned out by the time the company reaches the size of Google, so it’s all the more impressive they have this forum.

Communicating well is hard in a growing company as I’ve come to learn and you need as many ways as possible to share your thoughts on the future to keep everyone on the same page. We have been writing our own “Letters from the Founders” to all our employees, investors, and advisers once a quarter.

Since starting this practice, we’ve been able to better stay in touch with all our stakeholders and get offers for help in specific areas from them. It had begun as a one way street but it’s beginning to become a valuable conversation starter about the future.

I wish more companies would write these founders’ letters regularly — it’d be fascinating to hear what founders have to say to the world. 

I recently saw Midnight in Paris, an excellent film about a modern writer who thinks other artists’ lives and times are better than his own and gets to hang out in Paris at night with historic literary figures before they reach their prime. The film’s message concluded that we always glorify others’ lives and times when in fact our own can be as interesting (or as mundane). It resonated with me now that I’m living in San Francisco which is beginning to see the second Internet boom and many aspiring entrepreneurs move into town in hopes of capturing some of that excitement and glory that made up the dotcom boom of the late 90’s.

I had the opportunity this week to co-host a dinner party where we were fortune to have some amazing guests come join us. Discussion ranged in topic from Yahoo to Y-Combinator. The accomplished and successful figures unleashed their full personality in a way that reading about them on blogs and Twitter couldn’t capture. I had a moment where I felt similar to main character in Midnight in Paris in that I was surrounded by some of the emerging leaders who didn’t even realize how they will be revered by their successors in the future.

When someone pointed out how “unscalable” this event was in terms of spreading the knowledge and friendships, another person pointed out that “well, sometimes the most unscalable things are the most meaningful.” I think that’s true and I hope to have many such unscalable nights in the next year.

I ask myself now, what would a Midnight in San Francisco look like? Who would be cool to just get a drink with? Who doesn’t realize they are going to be a big deal and is looking to spend time with strangers wanting to learn?

Photo of the View From Dinner by Dan Martell

Recently, I was struck by how two esteem leaders in technology have both remarked on how you cannot connect the dots looking forward but only backwards. 

Sheryl Sandberg, the COO of Facebook, was recently profiled in The New Yorker:

Asked what she can imagine doing next, she responds, “I’m actually quite happy with Mark and the company. I always tell people if you try to connect the dots of your career, if you mess it up you’re going to wind up on a very limited path. If I decided what I was going to do in college—when there was no Internet, no Google, no Facebook … I don’t want to make that mistake. The reason I don’t have a plan is because if I have a plan I’m limited to today’s options.”

Steve Jobs gave a great commencement speech at Stanford:

You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever.

This advice goes against all notions of “career management” or “career ladders,” which imply some steady progression that can be controlled. The world just doesn’t work this way because there is always so much changing. The rules, norms, and conditions are never constant.

Can you imagine President Obama as a kid making plans to be the leader of the free world? The options of his day would be quite limiting to plan a life around. He certainly didn’t follow the normal education track or career trajectory, but he made it work out in the end. This idea doesn’t mean you should limit your ambition or goals but making such long term plans is almost a futile exercise since you and the world will inevitable change along the way. 

Whenever people ask me what I plan to do in the long run (hi mom!), my answer is I don’t have a plan. I just want to do interesting and challenging things, which will never be predictable by their very nature. Technology as a sector almost by definition fits these criteria since it’s in the business of new breakthroughs.

I trust the dots will all make sense backwards. 

While at a startup event hosted at the offices of Tokbox, I was talking to a bunch of entrepreneurs and noticed a bit of a pattern to the initial part of the conversation, which leads me to wonder whether within social groups, if there is always a set of routine, customary questions to begin with. People at the event typically would ask:

1. Where do you work?
2. What’s the pitch?
3. How many employees?

This series of questions would replace the set from college:

1. Where are you from?
2. What dorm are you living in?
3. What do you study?

These questions all probably represent the lowest common denominator of identity. They also represent the desire to find common ground between people. I believe people innately want to bond which makes them feel like they are benefiting from taking an interest in you and helping you out. I’m a big believer that people will want to do what they can to help you achieve your dream (see The Alchemist). That’s why I’m stunned when people refuse to talk openly about what they are working on or want to accomplish. It’d be like any person flatly refusing to talk about themselves in any basic manner.

In the startup world, this refusal comes in the form of the “stealth startup.” The founder of such a startup says he or she is working at a stealth startup and refuses to answer any further questions. All the sudden, the conversation feels one sided and almost antagonistic. You can’t help someone with something you don’t know about. After the “stealth bomb” is dropped, it no longer feels like you are both working together towards a common end so you almost don’t even want to talk to them anymore.

So if you want people to take an interest in you and help, then share with them. Don’t go stealth. If you do, you may get less attention than you want. 

Anxiety, Freud is said to have explained, is when you irrationally react to a simple stick as if it were a dangerous snake. Fear is when you react to a dangerous snake as if it were, well, dangerous. Anxiety is dysfunctional, but fear can be good: It helps protect us from things that are dangerous—such as risk taking. Entrepreneurs, in my experience, develop a healthy fear of what can go wrong. They just don’t let it paralyze them.