Many conversations with other twenty something year olds out of college seem to gravitate inevitably towards what we’re doing with our lives — as in, what’s the point in what we’re doing and should we continue doing it? I often hear people ask what is “the narrative of my life?” as though their story will be told to posterity, which is an interesting way to examine what you’re doing and whether it is worthwhile.

After listening and participating in many of these dinner table conversations, I’ve settled on a framework for myself specifically and possibly more generally. I think it’s far easier to wonder “what does the world need” rather than “what do I want to do.” One is concrete and the other is fuzzy, if not whimsical. Before money and glory, I think people want more than anything is to feel like they have an impact on what they work on and that what they work on matters on some level. By pursuing “what the world needs” it’s far easier to avoid things that don’t feel like they don’t matter since you probably are already unsure whether it’s what you truly want, let alone whether it matters to anyone else.

I’ve decided for myself that the problems most interesting and worth spending my life solving break down as follows:

1. Access to Information (data, news, know how, etc.)
2. Access to Capital (funding, credit, etc.)
3. Access to Sustenance (food, air, water, etc.)

These basic inputs have massive “leverage” or multiplicative effects on output for people. Improving access to these inputs enables people to do a lot more in their respective fields and improves living conditions everywhere. On a high level, information helps people do anything better and make better decisions. Capital enables people to pursue opportunities otherwise impossible or risky. Sustenance simply makes life possible and enjoyable.

I will go into further detail in what I’m doing, what I want to do, and why I care about each problem in coming posts.

I’m sure there are other fields that have large impact that I may be missing. What are big problems that you are happy to work on for the rest of your life or that you know other people are dedicating their lives to solving?

Reading the biography of Amazon.com’s CEO, Jeff Bezos, I came across this quote on hiring:

“One of [Jeff’s] mottos was that every time we hired someone, he or she would raise the bar for the next hire, so that the overall talent pool was always improving,” said Nicholas Lovejoy, who joined Amazon in 1995 as the fifth employee. Bezos put the philosophy this way: Five years after an employee was hired, he said, that employee should think, “I’m glad that I got hired when I did, because I wouldn’t get hired now.”

I thought this is a terrific approach to hiring. At first, it seemed to conflict with some common advice about hiring only A-players. How could you hire better people in the future if you already were hiring the best?

I realized the way to reconcile these bits of advice is that there are A-players for different stages of the company and also some A-players who can scale across stages. Hiring people who will do a great job at the current scale and have the potential to punch above their weight class can still leave room for “even better” future hires who come from even larger scale organizations where they succeeded. In spite of how far I’ve taken my company, PaperG, from its inception, I am still in awe of outside executives interested in working with us who have far more experience and success to date from their times operating much larger companies. 

PaperG is in the midst of a mini-hiring spree (expanding the team by about 20% in a month) to help us as we scale the business to enable some of the largest media companies go after one of the most exciting markets, local advertising. In some open positions, we just need to compare whether the new hire is much better than someone already in a similar position.

In other open positions, we have to think whether the new hire will be doing a better job than a founder could if he did it full-time. It’s a high bar —  but even founders should want to feel lucky they were the ones to start the company and not be the ones who are applying for the competitive position. 

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.