At the close of 2018 we signed the articles of dissolution for Voterheads, Inc. The site lives on under the ownership of my previous partner, without my involvement.

This was a very difficult step for me. I spent the last six(!) years of my life on the project, writing the majority of the codebase in use (my apologies in advance), and putting thousands of hours and dollars into it.  I’d like to believe we did indeed move the needle in making City and County legislation easier to track and follow, but I know I can’t be part of that journey anymore. This post-mortem is my first attempt to make sense of and learn from the experience

I believe/hope every step in life is worthwhile if you can learn something from it.  These are my thoughts and opinions fresh from the experience and so are probably still both raw and biased.  I don’t expect my co-founders will have all the same feelings but I hope when I look back on this post in later years that most of it will ring true.

What Went Wrong

Of course, if everything had gone correctly what’d be the point of a post-mortem, eh?

  • Ancillary Market:  When we first started Voterheads, it was a consumer facing application with nothing but ‘Advertising Revenue’ as a model to viability.  However, the consumer market we had at least some understanding of; both of my founders had worked on consumer-facing project and businesses.  I had worked with and understood local government from a product and consulting side, so our current model was already one step out of my lane for me. As we presented our solution, we found someone willing to hand over money for our product (*gasp!*): a regulated industry that was impacted by local government.  We quickly moved into this area as a product offering before our consumer-facing product was fully baked, and found ourselves in a B2B market in which we had neither experience nor contacts.  We managed to sell more subscriptions, but each one was like pulling teeth, as it was a Sisyphean process of skirting by gatekeepers of what ended up being a small market potential of companies with enough revenue and scope to care about local governments across a large area while at the same time sufficiently impacted by them.
  • Partial Pivots:  We may have made a success of moving to serve regulated industries exclusively, but I didn’t want to fully pivot, thinking (and convincing my partners) that we could do both, and potentially eventually even more.  Frankly, I didn’t want to move forward with the company unless it could both do good and do well.  However, this left us spread too thin, where progress went *way* too slowly as we spent too large a percentage of time manually fulfilling the requests of existing customers to retain them and their revenue.
  • Taking Funding Too Early:  One impetus of the pivot was because we had taken on funding.  Not a lot, by Silicon Valley or frankly any other standards, but enough; enough for us to latch on to the first smell of revenue without having an honest discussion about whether it was the right way to go, or pivoting away quickly enough when it didn’t yield sustainable results.
  • CoFounder Mismatch:  This is a tough one.  I dove in too quickly based on not much more than a few conversations and a recommendation, and without us spending enough time working together.  At the same time we took on legal services from an incubator that set up articles of incorporation that chained us together and threw away the key. By the end of the second year our discussions became laced with mistrust. There are several key points throughout the years at which one of us just should have walked away.  Instead, by year three the well was poisoned; every interaction left a bad taste in my mouth and I looked forward to the next about as much as root canal work…. but I was in love with our progress and our potential, that I felt we could outgrow the issues.  We tried a few more times to work together. While both sides may have given an honest effort, we ended up at the same point. Even during the dissolution, there were accusations thrown about that showed a deep-rooted distrust of the relationship.
  • Imposter Syndrome & Paralysis:  There were a few times

What Went Right

  • Tech Stack:  Yeah, I know, Ruby on Rails is so uncool, it doesn’t work for anyone and doesn’t scale.  Well, I never got to the size of Twitter, so I can’t tell you about scaling issues.  Ruby scaled to our size of several thousand users just fine, let me test out and grow out a ton of ideas in the process, and was both incredibly forgiving and incredibly fun.  I’ve been working with React and Redux lately; the amount of boilerplate for simple operations makes me wonder if it’s really just a rage quit game delivered via npm.
  • CoFounder Fit: My other co-founder had previous businesses and knew all the ups and downs (and now mostly downs) that he was signing up for.  Yet he did it anyway, stuck through most of it, and delivered a ton of great work product.  Most importantly, he’s been a great team member: listening, talking through strategy and next steps, sometimes challenging me but always supporting ‘the cause’, and always willing to take on a task within his skillset, and even some outside them.
  • Team: We’ve had some amazing people working with us, who saw the vision and who often gave their all to it.  Thank you.
  • Users: There is nothing more rewarding in your professional career than sharing what you’ve created and hearing someone say “That’s amazing!”.  Those moments of delight might have kept me going longer than I should have, but I wouldn’t trade them for anything.  Thank you to everyone who interacted with us and with the product over the years.  I wish I could have done even better for you.
  • Family:  My family, and especially my wife, have been more patient and supportive than I deserve.  I’ve tried my best to ‘balance’ home and work life, but know there are times I’ve fallen short.  I need to publicly thank them for putting up with me and my many foibles.

What Now

I love working in the civic space and with Cities.  I currently work with several in the Carolinas on an regular basis and love being able to work with them to assess, recommend, and implement projects that make them more effective in delivering solutions to their citizens.  I get to ‘do good’ for communities all around me.  At this point, I’m focusing on closing out my time with Voterheads honorably,

Voterheads at the Democratic Convention

doing good things for the Cities with which I work, and if I find an opportunity that gets me excited to be more effective and help more Cities, then I know I’ll be ready to take on that challenge with a few more notches under my belt.  In the meantime, if you’re part of a City that needs a technologically unbiased but unabashedly sympathetic look at your strategy and how it relates to technology, please come find me.

In the meantime…. due to the weekly cycle of council meetings being published Friday afternoon and customer QA, I’ve had maybe a dozen weekends off over the last six years.  I’m looking forward to enjoying a few of those this year with time to learn and think about a slightly larger scope while enjoying and appreciating a little more of the moments available with my family.  I’ll continue to blog and write here and at cityilluminated.com,

So, if you’ve been part of the journey so far, thank you:  for your time, your attention, and your support.