Today was one of those days when it was nearly 1pm before I was free to sit down and make my daily to-do list. There was water damage in my apartment, one of our awesome engineering candidates took an amazing job offer with a top video game studio instead of us, and I was way behind on all of the PR / marketing stuff I’m doing because we haven’t hired someone for the position yet. Typical, stressful day in the daily life of an early stage startup CEO.

So I sat down at the counter of a diner near our accelerator and started writing down my daily to-dos in the nearly-full, leather-bound Moleskine notebook I’ve used to keep myself and my thoughts organized for the past couple of years.

I just happened to open my notebook to an entry from 11/12/2011 (about a year ago) entitled “Skills I Want to Acquire.”

At the time I wrote this piece I was 15 months into my career at Microsoft and had just finished off a stressful pre-Thanksgiving crunch period, and I was starting to think about what I would need to learn in order to run a new startup.

I remembered how I felt when I wrote it – desperate to try my hand at starting a company for the second time1, but unprepared by my own standards.

I wrote this list as a roadmap to prepare myself for startup #2:

Skills I Want to Acquire – 11/12/2011

  • How to work with a team of developers
  • How to manage developers operations
  • How to manage a product lifecycle and iteration
  • How to measure customer engagement and how to incorporate those learnings into product design
  • How to build an online revenue channel
  • How to build a production + web and mobile service
  • Natural language processing + machine learning
  • How to build a developer platform / API
  • How to build a team
  • How to quickly prototype ideas and test them in market
  • How to manage a team
  • How to raise capital
  • How to acquire early customers
  • How to do great front-end development
  • How to build a brand

To be clear: these are all things that terrified me.

These are things I didn’t know or think I would be good at, but I knew I needed to learn them in order to realize my goals.

Today I went through this list and made the following notes:

Skills I Want to Acquire – 11/12/2011 updated 12/3/2012

  • How to work with a team of developers – done
  • How to manage developers operations – done
  • How to manage a product lifecycle and iteration - done
  • How to measure customer engagement and how to incorporate those learnings into product design - done
  • How to build an online revenue channel – done
  • How to build a production + web and mobile service – done, at scale
  • Natural language processing + machine learning – not done
  • How to build a developer platform / API – done, at scale
  • How to build a team – done
  • How to quickly prototype ideas and test them in market - done
  • How to manage a team – done; will be a lifelong process
  • How to raise capital – done
  • How to acquire early customers – done
  • How to do great front-end development – in-process
  • How to build a brand – done, but different than I expected.

To my immense pleasure, I had learned how to do most of these very scary, unfamiliar things in just a year! Of course I haven’t mastered them all yet, but I’m at a point where I feel confident that I can do any of these things competently at any time for our company and our team.

Given my day to day responsibilities at MarkedUp, I can’t imagine a world where I don’t know how to do most of the things on this list; it’s remarkable to think just a year ago that all of this stuff was alien and frightening to me.

Seeing this list and thinking about the progress I made from a year ago made instantly lowered my stress level and reminded me just how much progress one can make in a relatively small amount of time. It made me forget about all of the things I tell myself I’m doing wrong every day.

You are the ultimate judge of your own success, and I judge myself as having a really successful year so far.

If you want to do something hard like start your own company, start by sitting down and making a list of the things you need to do in order to get there, start trying to do them, and then review your progress against goal. You might be really surprised with how far you can get in a short period of time!

Now I’m going to get back to work on the next set of things I know I need to learn…

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