Run Your Playbook, Not Someone Else’s

95% elation, 5% terror. That’s my perpetual state in thinking about my personal playbook as a seed VC. Developing, refining and iterating on that playbook is the single key to my success but it’s also characterized by small datasets, long cycle times, inevitable mistakes. What I mean by playbook in this case isn’t Homebrew’s overall strategy or best practices for managing a fund. I don’t think it’s a ‘personal brand’ as an investor either, or at least marketing is an output of a playbook, not an input. Instead my playbook is the combination of three understandings:

  • Who am I?
  • What do my customers (entrepreneurs) need?
  • How do I execute on the intersection of the above two points?

I’ve written before on my belief that self-awareness is the consistent trait among all my investor role models – that’s the Who portion. The What portion comes from a POV around technology entrepreneurship in general. The How is about resource allocation. End of year is a traditional time to step back and think about how one spends their time. As a new VC I’m confronted most consistently by the opportunity cost of where does the incremental hour go since there’s always another valuable hour of work to be done – another person to meet, another emerging technology to learn about, another event to speak at, another commitment to honor. Each of these in a vacuum is ROI positive so you can’t just say “I’ll do anything which has some positive short-term benefit.” Even prioritizing just by perceived ROI won’t give you a consistent strategy – that would be like designing a product as just a collection of high priority features rather than an integration solution which solves actual problems (sidenote: LOTS of products feel like collections of features. They usually struggle). So your playbook is not just a collection of formations but a system, one which says “here’s all the things you can do in order to win” and will continue to build/refine your own skills to execute.

I see lots of VC playbooks that I know aren’t going to be the one that feels 100% right to me. There’s the Social Investor who maximizes coverage by being at all the right events, tireless working crowds, networking. There’s the Research Lab Investor who stays close to hardcore technologies being pioneered on university campuses. The Cerebral Investor who develops their own systems and frameworks through which to see the world and pattern matches against them. And so on. Each one of these approaches have some tactics which feel familiar to me but I know running the entire playbook would be a failure. At best, I’d be a silver-medal version of someone else.

This post isn’t going to conclude with a summary of my Playbook (which is still just conceptual in nature) but I’ll share a few of the things that I’ve tried during 2014 to help me figure it out.

  • Ask your role models how they spend their time – at a really granular level. Figure out some of the rituals they do – the first 15 minutes of their day, the last half hour. What do they think about at a day/week/month/quarter level of separation?
  • Pick some people you admire in your field who are very different than you are – try to figure out their playbook (at a high level). Is there overlap in your playbook? Maybe that’s a signal to discard some of what you’re doing to focus on more unique activities. For example, I look at a bunch of different industry conferences that are buzzy and attended by many investors but not by any of the investors who I feel most similar too. For me that’s a confirming signal that it’s a good use of time in many playbooks but not mine. (sidenote, I’ve realized that I don’t have FOMO so much as FONBI – fear of not being invited).
  • If you work in a team – as I do with Satya – understand where your playbooks overlap and where you differ. This helps to ensure that your partnership – like the best products – are greater than the sum of their parts.
  • List your blind spots or what makes you uncomfortable. Decide which are deficiencies you need to overcome and which you will be aware of but not worry about. Once something has been put in the “don’t worry” box, stop comparing yourself to people who excel in those areas. Stop beating yourself up for not being as charismatic, analytical, etc as some person you put on a pedestal. You get further building on your strengths and being aware of your weaknesses than you do trying to make sure you’re average across the board.

So put this post in the “thinking outloud” category – if folks take different (or similar) approaches would love to hear about them.

2 thoughts on “Run Your Playbook, Not Someone Else’s

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