#fdhbs

On Tuesday I wrote about how founding a company is a lot like dating.  It was a tongue-in-cheek post to describe my views on “running experiments” and “prototyping”.  However, I couldn’t help but feel that I neglected a lot of genuine content.  I didn’t talk about my own struggles deciding whether to take the founding plunge.  I didn’t share any of the lessons learned as a solo founder.  And frankly, I skirted past true reflection.

Well, this is the (first) post to change that.

For (more) background, I spent the last semester working on a startup I believed I was perfectly suited to found.  It sat at the intersection of several past experiences in SaaS (D3 Security, Wildfire), healthcare IT (aptitude LLC) and behavioral health.  And was consistent with my broader vision: that our fragmented healthcare system would become “mapped” through virtual networks.

I actually returned to this idea after setting it aside earlier in the year.  I couldn’t help but feel that I too quickly dismissed the opportunity; it was more a result of convenience and timing that I “put it to bed” than fully vetting and evolving the concept.  So, I hit the ground running diving into prototyping and “selling”: I mocked-up vaporware, created a demo video and made a pitch deck. 

I won’t go into the nitty-gritty details about what did (and didn’t) validate the concept.  But instead wanted to expand on the very personal challenges I struggled with.

First, it was (at times) really lonely.  As a solo founder, I often found myself lost in conflicting thoughts.  I was riding a rollercoaster by myself: one conversation would feel like a complete beating, the next completely exhilarating.  It was a challenge to stay motivated week-to-week, to stay accountable to myself. 

Second, trying to read the “tea leaves” across multiple, often contradictory meetings seemed nearly impossible.  Were the “sold” or “not sold” customers right?  How much negative feedback was a result of technology “skeptics”?  Could I simply design around the potential challenges or did they make the concept “dead on arrival”?

Finally, I felt a constant tension between two roles: the passionate entrepreneur and the venture capitalist.  As much as I wanted to believe I was “right” (and on the cusp of creating the next great healthcare IT startup), as much as I wanted to will my startup into existence, I couldn’t help but play the role of skeptical VC. 

I really struggled with this.  On the one hand, great VCs dig into the market dynamics, customer incentives and revenue opportunity.  On the other hand, great entrepreneurs are fanatically passionate about their vision.  They see something that others don’t, that a model can’t forecast.  I constantly wondered: am I striking the right balance between each?  Am I teetering too far in one direction? 

As a result, I’ve come to a few lessons that will be core to my entrepreneurial journey (and hope they're cause for reflection for aspiring entrepreneurs).

1.       Quickly find mentors and a support network

As I said, founding a company can be lonely (especially as a “lone wolf”).  But mentors are invaluable to test hypotheses, provide encouragement and as forcing mechanisms to “do the work”.  For me, I looked for a balance across healthcare experts (Graham Gardner @ Kyruus), product development (Tom Eisenmann @ HBS) and other entrepreneurs (Rock Accelerator, iLab).

However (looking back), I often felt like I used my mentors more as sounding boards than as pseudo- team members.  In the future, I’ll do a better job of sharing what I’m hearing from the field to really dig-in into the startup’s challenges together.

2.       Mock-up a “business plan” prototype (and work on it over time)

I realize business plans are out-of-favor.  But to help “read the tea leaves”, it’s worth the time to not just capture what you’re hearing from the field, but also synthesize that into your startup’s story.  

Think of it as a “rough prototype” of what a business plan would be.  What is the core problem you’re solving? What hypotheses do you have?  Are you validating demand and business model? 

As an example, I used a Google doc to track insights from all my meetings.

3.       Spend as much time on “recruiting” as “customer development”

I don’t think I spent enough time “recruiting” potential team members (and co-founders).  Though I attended the odd hackathon and talked to almost anyone who would listen, there was still (a lot) of room for improvement in building out a team.  Realistically, you can only go-it-alone for so long.

Luckily, I’ve ended up meeting a team that might bring my vision into the world.  However, it’s come with another takeaway: stay committed to your long-term vision, but don’t be dogmatic about its early execution. It'll help you build the team and expand your horizons about what’s possible.

4.       Understand your own founder profile

Really, the takeaway is trust your gut: understand what will give you confidence to take the “plunge” and what kind (and scale) of business you want to build.  For me, I’m unlikely to be a truly “spontaneous” entrepreneur even though I’m highly optimistic about what’s possible.  I’m just far too analytically-minded to dive right in without doing the work.

I’ll admit: that’s one corny title for a startup blog post.  But (recently) it’s really occurred to me how much founding a company is like dating. 

For background, I’ve spent the last twelve months exploring two startup ideas in depth (one is still evolving post- HBS’s Rock Accelerator) and kicked around countless others. I’ve also thought a lot about how you know when to take the proverbial founding “plunge”. 

It’s clearly not an inconsequential decision: it’s a significant commitment of time, opportunity cost and capital.  And is only magnified once you raise funding (given the fiduciary duty that comes with it).

Now, back to dating. 

I think you’d be hard pressed to find someone that would propose on day one. 

Instead, there’s a somewhat predictable process: you have a first date (make paper prototypes), meet the parents (do customer research), move in together (run a live experiment), and discuss careers and family (vet the business model). 

Essentially, you’re "de-risking" a potential life-long commitment by testing hypotheses and gathering as much information as possible.  And like any great entrepreneur, you've always got an “exit” strategy.

In the end though, every founding story is different.  Sometimes it’s love at first sight.  Sometimes it’s years of dating.  And sometimes it’s a chance meeting.  But as long as you’re in the “game”, you’re bound to stumble upon “the one”.

As for me, I’ve definitely been dating.  Though can’t say I’ve fallen in (startup) love.

p.s. credit due to Wildfire Co-Founder and CEO, Victoria Ransom, for inspiring the “love at first sight” title during a conversation in July 2013