Over the past 8 years I have started 6 companies. I sold two and one is growing fast. I have also advised dozens of ambitious entrepreneurs. Across all companies, I have built ten different products to varying degrees of success *.

Here is a list of general thoughts on startups:

  • Build something people want. It sounds like a no-brainer, but people need to be reminded to build something people want. When building products the quickest way to finding out if someone wants what you’re building is to ask them! Finding a problem that people currently have is a good starting point. Validating that people have this problem and then building solutions that solve these problems is at it’s core the most straight forward way to start out.
  • Focused experimentation. When building a new product it is unlikely that you will start out with a clearly defined problem. It is important to invest time up-front to clarifying a set of hypotheses that you are solving. Do everything you can to avoid building software at this stage. A mockups, design compositions, and test landing pages can help save a lot of time!
  • Stay Focused. Generally, a “see what happens” attitude creates products and projects that switch focus quickly and without structure will waste time. With a structured approach one can produce useful data points and insight. Start by including a general thesis statement and a couple testable hypotheses. These hypotheses should be shared with the entire team. Everyone on the team should understand what is being tested and why. The group can be allowed to work individually or in coordination with others towards proving or disproving the thesis. Any work beyond proving/disproving the thesis should be avoided.
  • Complexity hides shortcomings. I find that it is very easy to over complicate things. Complexity hinders growth and learning by distracting you from important matters. Complexity tricks you into a false sense of accomplishment (busy work). Strive for simplicity.
  • Ignore vanity. Obsessing over vanity metrics, unnecessary or seemingly random marketing gimmicks prior to product market fit, premature partnerships or collaborations with other companies that can distract the team from finding product market fit, and otherwise pointless expenses of time and energy are a good marker of an inexperienced or unskilled founder. How do you know a metric is vain? You want to brag about a certain metric, but you know that it has no bearing on your business actually making money.
  • Simplify! I don’t know what you are building, but I can guess your product too complex. Go back to the basics. Build things that solve problems that real people have. In most cases cutting away to the deeper issue at hand allows you to find a very simple problem and sometimes (but not always) a simple solution.
  • Build for a vision. The entire team must believe in the vision and make every decision towards furthering this goal. Every ounce of energy not put towards fulfilling your vision is a waste.
  • BE BOLD! The emotional roller coasters of the startup life is not for the feint of heart. If your startup is struggling, delayed, or languishing, then days can feel like an endless grind. Be bold! Own it! Be it!
  • Always be selling. If you are the founder and you are not talking about your product, team, or service all-day, everyday, then you will lose. I played the humble card one too often. I apologized myself out of many opportunities.
  • Just one more feature! Stop pinning growth of the company on features. Don’t tell people that you are waiting until you have feature “X” before you really push. What if you never complete feature “X”? Seems like quite a risky proposition and story to pin on your product. Do you really need to build “X”? Are you sure?
  • Wabi-sabi. Finding life balance and running a startup is futile.. Accept and embrace incompleteness and being in a state of works in progress. Trying to build product, acquire users, raise funding, stay focused, hire people, experiment, learn, communicate effectively, project a sense of control and vision, keep vendors paid, work to direct the team towards the companies goals while also fulfilling their own needs… can become a bit much. Prioritizing and focusing can help.
  • Probably not gonna work. Don’t kids yourself. Most of your ideas are wrong. Act knowing that things may fail. Proactively construct your roadmap and sprints to incorpate, adjust to, and account for learning.
  • Reflect. Take personal inventory frequently and reflect occaisionally. It is important for small startup founding teams to find their center, but not dwell. It is also good from a personal standpoint to build a periodic history of lessons learned: listing what you thought would happen, what actually happened, and what you learned.
  • Curious Strive to stay curious, and interested, act as if you are still a young scientist that doesn’t know.

  • Having a mission. Beyond startups, a founder that aims to fulfill a (healthy) personal mission is a force with which to be reckoned. Finding this personal mission is hard. It helps to experiment with ideas, but then to be very specific about what success means in the context of your mission.

Ex. My personal mission is to help and empower people. One way I aim to do this is by helping 1000 people build a home or pay for their housing. I want to empower people by helping them learn how to learn. The reason why I supported an acqusition by the cryptocurrency company OpenCoin was that I believed their goal of “distributing wealth on a global scale” fulfilled two things: helping give people money would let them pay for their housing. It would also help them be self sufficient for earning an income by working to lower costs for transmitting $ and for cutting out the multiple layers of people between transactions (c.f. Africa).

From a macro view, the points I have shared involve solutions that grow increasingly in complexity at the sake of a clear purpose. Maintaining a clear purpose is critical.

Notes: Products I’ve built: I Can Has Cheezburger? kittehs, I Has a Hotdog! whargrrrbbls, co-authored a NYT Best-selling humor book under the pen name “Professor Happycat”, built a couple social media plugins for Wordpress (plurk), MyChamberApp local and mobile advertising for Chamber of Commerce members, WhatChefsEat restaurant recommendations from chefs worldwide, LeiFresh shifting consumption of imported food by helping people track and buy locally grown food, HawaiiFareSurfer finding the lowest airfare from anywhere to Hawaii, simplehoney was a personalized hotel search engine based on traveler preference, IWantHoney was a mobile shopping wishlist that help people track and share the things they want, was acquired by digital currency company Ripple