z on life

The most useful thing I have learned in my whole process of startups, and maybe even life for that matter, is the importance of the phrase “know what you don’t know”.

It is crucial to learn everything you can from everyone in your life, be it friends, family, engineers, venture capitalists, or complete strangers. Being able to learn means you know what you need to look for from each these interactions. Knowing what you need to look for means knowing what you don’t know. You should go into every interaction knowing exactly what new information you can extract. This isn’t selfish, it is merely efficient learning. Besides, you probably have lots of cool stuff to offer in return.

When people don’t know what they don’t know, they are bound to fail again and again. Unfortunately, this happens all the time, especially to those who are young or inexperienced. I have been definitely been guilty of it too, so I’m no exception. Knowing what you don’t know keeps you searching with tunnel vision, and if that great idea or strategy isn’t directly in front of you, you’re never going to hit it. From the perspective of success over a long period of time (let’s say, a career), this is so dangerous. It’s a recipe for having a long, tough, excruciating string of failures.

Not knowing what you don’t know is like tweaking variables in an equation to find the local maximum. Knowing what you don’t know means you are going to throw that whole notion away and find new variables you can to use to find the global maximum. Think outside the box, and throw away all of the artificial constraints you’ve put on your thought processes.

When planning, strategizing, or thinking, here’s some questions to think about:

1. What concepts have I previously written off as ‘not-relevant’ to me?

2. Who would have a new outlook on this and why?
3. What about me or my experience is limiting how I look at things?
4. Are there any tangential skill-sets or knowledge that I can acquire?
5. Can I draw intuition from whole other areas, industries, genres?

If you adopt the “know what you don’t know” mindset, you go through extremely fast cycles of self-revision, become a wider/deeper thinker, and convey to others that you have put ego or image aside in exchange for great self-advancement. That’s the mark of someone who wants to win.

I can’t help but quote a great book written by Neil Postman and Charles Weingartner called “Teaching as a Subversive Activity”, recommended by the wise Jared Kopf. Knowing what you don’t know is all about maximizing your ability to learn, and in this book they talk about the characteristics of learners. They say that good learners:

1. Have confidence in their ability to learn

2. Enjoy solving problems
3. Know exactly what is relevant to their survival
4. Rely on their own judgement to spot good and bad advice
5. Do not fear being wrong
6. Are not fast answerers
7. Are flexible
8. Have a profound respect for data and information
9. Do not need to have one irrevocable solution to a problem

It’s clear that many if not all of these things are drivers for or can be driven by knowing what you don’t know. Nice! I can rest easy knowing that someone who actually knows what they are talking about agrees with me.

Very recently I moved from Pittsburgh, PA to sunny San Francisco, CA. I’ve only been here a few weeks for real now, but the differences in the city are pretty obvious. I wanted to share my thoughts on how you would make Pittsburgh into San Francisco:

1. Increase property values by 500% 
2. Add slides and hot tubs to the nightclubs 
3. Stop everyone from caring about their NFL team
4. Turn 1 in every 4 people into Facebook app developers

It’s pretty unlikely this will happen any time soon, and obviously this is somewhat less than serious. But in reality, from the perspective of an entrepreneur, what does Pittsburgh need that San Francisco already has? The following are four items that are for real.

•  A wealth of capital (financial + social)

This is completely straightforward. There’s more money in a top tech fund here than all of Pittsburgh combined, and the concentration of talent and knowledge is simply astounding. Of course, the venture community in Pittsburgh has likely hit a carrying capacity for the amount of deal flow, so it’s not like simply adding more money fixes the problem (imagine a logistic growth curve math problem where you add more wolves but keep the number of sheep fixed). This is a standard chicken and the egg problem that has to be attacked from both angles.

•  Open, cutting-edge idea flow

Entrepreneurs in the bay don’t see success as a zero sum game and are willing to share strategies for success. Especially in the space of viral and user acquisition plays, we’ve seen a number of big wins in the recent years building and manipulating a core of techniques shared by a number of great entrepreneurs. Successes can coexist, and by being open and accepting this, the bay area has created a self-fulfilling loop of staying ahead of the rest of the world with some of the best information flow I have ever seen. Too much secrecy is dangerous.

• Building for the long-run

We’re going through a process of hiring right now, and it is interesting to think of things not just in terms of skills, but much more so in terms of trust and long-term relationships. When you’re in a small pond, you’re willing to bet on skills because you need to get the job done. When you’re in a big pond, you need to be on trust and long-term value because the payback of these seemingly softer things greatly outweighs any feature or any component of a product that a hire will get you in the next 6-12 months. At the end of the day you’re betting on the people more so than the tangible thing they can immediately provide you. A good question to ask yourself is ‘would you unconditionally work with any and/or all members of your core team again?’ Entrepreneurs should bet on themselves and their teammates to succeed in whatever, even if the current venture fails miserably.

•  Stars that have serious gravity

Pittsburgh needs to make very visible a set top-notch entrepreneurs who others badly want to work for. Simple jobs are great, but at the end of the day a job boils down to a corporate position P with skill needs A, B, C that provides salary X and Y stock options. Long-term career growth is much more than money today and a resume line item tomorrow. Would you rather work at Microsoft, or be Bill Gates’s right-hand-man? What if the latter meant half the pay? I would argue that in many startups, you can work with truly awesome people and not even sacrifice those other elements. The question is, are these people visible? And does the common person know what that relationship will do for their career? Better yet, does the diamond in the rough fledgling entrepreneur know who these people are that can jump start his or her career? Just some thoughts…more to come…