Going It Alone


The other day I watched a webinar with two managing directors about what it takes to join Techstars.  The first discussion point was about solo founders.  I’ve been wrestling with how to talk about my own status as a solo founder so I am going to try to create a narrative about not just why I think I can be successful, but also possibly help other entrepreneurs formulate their case.

The theory of a ‘team’ to start a new company is that you bring together people with complementary skills.  Typically at least one is technical and one product/business focused.  I think this strategy is really useful for young founders.  Their breadth of experience is just not broad enough to extrapolate how to handle new situations on the side where they have limited expertise.  I’ve noticed this more in the past few years as I get more face time with newly minted college grads in our office.  Note that we hire some very well qualified candidates from top schools, but they still lack skills (architecture, customer focus, basic understanding of business, politics).  But if you put a few younger people together, you usually cover enough ground to make them effective.  In which case, multiple co-founders make sense.

Between my finance degree, accounting stints, and years in consulting, I have a pretty solid background for understanding ‘business’.  I’ve spent a number of years recently as both project manager (making sure a team gets things done) and product manager (setting the vision for what the team is going to do).  No one would call me a ‘techy.’  However, I have fairly decent SQL and database design skills.

But what I really do well is something that many can’t.  I can work with a customer to craft a vision for the product, design a flexible solution for that problem and then communicate that concept to a development team.  Over the past 14 years of being at Fidelity, I have been coordinating these efforts with teams in North Carolina, Texas, Boston, Ireland, India, and China, all from our home base here in NH.  At the worst, my dev team was split among 4 of these sites simultaneously.

Sometimes I did well.  My most recent design challenge leveraged 20+ developers working on a solution in multiple sites on different components and technologies.  We came in on time and under budget.  Other projects were not so successful.  On one, our inability to convert large datasets accurately, led to missing our install window by a full quarter.  I have worked dozens of complex projects and learned from each one.

These experiences have proven to me one undeniable and consistent fact.  It is the strength of the design that was the most important factor in our success.  We worked most effectively when I was in sync with the team, communicating the concepts to the developers, letting them work through the details in the code.  Between shifting sites, pro-serve resources and changes with business partners, we are always cycling new associates in and out.  As long as I could brief them on the vision, their part in the whole picture and what was expected, things went well.  Unfortunately, perpetual change is a reality on any project, and subsequently managing that change is a critical skill to success in a project that is scaling.

Further, when I truly understand the problem and 100% own the solution design, I can work with any team.  Experience affords you the ability to talk to people and build a relationship because inevitably you have shared lessons that help bridge the gap of newness.  Team is more than proximity or friendships.  It is empathy, understanding, communication and setting clear goals.  It is also culture.  Books such as Extreme Ownership, and Team of Teams have taught me lessons that I use to build culture every day.

As I look to head out on my own and build TheMissionZone in earnest, I have decided that being a solo founder with a virtual team, is the optimal strategy for me.  (I also plan to write code, because it is a valuable skill.)  I believe that creating the infrastructure where I am able to grow an organization designed to scale right from the outset, is the best way to deal with challenges that will arise later.  Also, since I am not 100% sure what parts of the product are best to develop first, I can’t necessarily nail down the skills needed for a technical co-founder.  Flexibility now, is my most important HR asset.

There is also the ‘too many chiefs’ problem.  And I don’t believe this should be understated.  I keep hearing about startup founders that fight, disagreements on vision, market segment, etc.  Given all the input that is available through customers, colleagues, coaches, mentors and even through professional meet-up groups, a CEO really doesn’t lack objective opinions.   A co-founder has the potential to muddy the decision making process.  Right now, I don’t need that.  I need to move fast and break shit.

And then there is the whole ‘adult’ problem.  I am old.  There is no “living on ramen” for me.  I couldn’t convince my peers to quit their job to come join me.  Getting paid in equity for a 23 year old living at home is fine, but it doesn’t feed the kids.  My network are all adults, they have real lives and families.  Would they quit and take a pay cut for a paying job with equity and added flexibility without the political BS of the corporate world?  Probably.  At some point I will start making those calls.  I may be able to get myself into a comfortable position to quit my day job, but I can’t reasonably expect that of others.  Many of these friends continue to be advisers and I lean on them constantly.

Given what I have laid out above, I know I would function well as a solo founder.  But how does this fit into a general set of personal characteristics and approach that might help determine if you might also be well suited as a solo founder?  I will try to spell out those desireable characteristics below…

  • Have a rock solid design.  Create a design based on components so you can leverage a disparate team
  • Design for interoperability of the plug in components
  • Know your culture before you start, it can always evolve, but there has to be a foundation and understanding for those that join.  People want to know what they are walking into
  • Have a plan of how you will scale the team both temp resources and full-time
  • Be sure you define roles well.  Have experience motivating and inspiring teams, coaching underperformers where necessary
  • Have a broad network and feel comfortable tapping it
  • Know your MVP before you build it.  You should already know the first test case and tackle it.  Pivot later
  • Have damn good project management skills and understand how to work in a matrixed environment with multiple priorities
  • Be awesome at communication.  Know how to write clearly and coherently.  Know how to draw pictures to communicate with those for whom English is not their first language
  • Be humble and work with your customer to define a true requirement and how to solve problems most effectively.  Don’t just survey, understand the answers to questions
  • Have some sort of technical skills.  Understand how code has a logical progression and data tables can impact code.  Know how to communicate in boxes and lines.
  • Be able to visualize how rules based code will enable you to scale and not create hard-coded technical debt.  Recognize each of those tradeoffs
  • See the big picture of product and customer and revenue and partners
  • You must have basic accounting/finance skills.  Know time value of money, budgeting, spreadsheet modeling with variables, and product costing

This is not a complete list by any stretch.  I will continue to evolve this post over time.  Please give me feedback in any form!

There is no belayer or grigri when you are a solo founder.  So climb when ready…  Climbing!

About Josh Rutstein

I am an aspiring entrepreneur and hopeful political candidate. Father of 2 very special girls, husband to an amazing woman, and passionate American. I snowboard whenever possible and follow a 20x mentality for exercise. I also play golf and ultimate frisbee and am a die hard New England Patriots fan and season ticket holder. Everyday I wake up wanting to make this country a better place, someday I hope to actually succeed.
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