No shortage of those.

Death by a thousand great ideas

Originally published on my personal website in April 2012.

found·er¹ (noun)
a person who establishes an institution or settlement.
the excited founders of a Silicon Valley startup

At first, my co-founder Rahmin and I felt like we could do anything. We hadn’t set out with an idea — it was just, “Let’s start a company!” We’d found each other through a shared interest in continuing education, but we were interested in taking six months without committing to a specific path. “Just be curious,” said one of our advisors. Sounds like fun, right? It is fun, at least for a while.

We had a lot going for us as co-founders. We worked well together, we were both startup veterans, and we shared a lot of values. We were good coaches for each other. We found wonderful advisors — seasoned Silicon Valley founders who graciously came by every week or so to peek in and give feedback.

Over nine months together, we built a strong user-centered product discovery and testing cycle. We interviewed at least a hundred people and we ran several experiments to validate hypotheses. We developed elaborate customer archetypes, ran surveys, and iterated through Lean Startup-style learn-build-measure loops.

We were in pursuit of a great idea. A brilliant idea that elegantly solved an audacious problem. An idea with clean lines and graceful curves, horizontally and vertically dovetailing the interests of many.

found·er² (verb)
(of a plan or undertaking) fail or break down, typically as a result of a particular problem or setback.
the startup foundered because of leadership troubles

But from the beginning, we bore the curse of too much freedom. We could get through one or two loops for a given problem space, but it was too easy for us to abandon an emerging model at the first or second hurdle. New ideas are gangly and unrefined, and we were impatient. We’d stick with something for a week or so, then we’d develop an excuse:

  • “I don’t think there’s a real business here.”
  • “There’s a business here, but it’s too small.”
  • “We found something that’s nice to have, not need to have
  • “We can’t play to our strengths in this problem space.”
  • “We didn’t hit a high enough viral coefficient with our prototype. There’s no way we’ll get critical mass.”
  • “I shared the idea with so-and-so, and he wasn’t excited.”
  • “Remember… ‘six months of openness’…”

One of us would lay down the excuse, and the other would respond by proposing an exciting New Idea. We’d clear the whiteboards, pull down hundreds of stickies, and start over.

Some of the excuses were totally valid, but underneath it all, I felt that Rahmin and I were afraid. Our creative latitude was unsettling. We were skirting around on the surface of all these ideas, but because we hadn’t agreed on a single deeper purpose or vision that had brought us together, we weren’t standing on solid ground. Our fears prevented us from going deep in a single direction. One day we were a social network for generosity, and the next day we were reinventing the university.

We noticed this about ourselves, and we both took a lot of time on our own to see if we could uncover some deeper whys that would give us a deeper commitment. We wrote about it. We shared stories with each other about what had led us to this moment, and why we thought we should be starting a startup at all. This was helpful but it didn’t get us into alignment.

The fact is, committing to a problem space with someone is scary. We tried to choose but no choice stuck. We were frustrated that after a handful of user interviews in a new direction, a great idea hadn’t sprung out fully formed. So we changed course. We did more exploring, in the Stanford d.school sense. Our IDEO-approved product discovery methods felt like productivity. We’d have done well as experience design consultants. And while it felt liberating to clean the slate week after week (“glad we don’t have to solve that problem”), there was always a baseline uneasiness. We didn’t have the manic drive to make something — we were pushing ideas around instead.

If our office was an incubator, we were dancing on the eggs while trying to change the light bulb.

I think the startups worth starting happen to their founders as a compulsion. In our efforts to move forward, Rahmin and I were guilty of feigning excitement around some of the ideas. I think this came from the pressure of working full-time without an idea.

Given another few months, we might have found a groove. But our indecision was a symptom of our struggles to take, share, and delegate leadership. This is a very personal discovery. Looking back today, we both felt guilty about not being the Alpha Founder. But there’s no such thing as the Alpha Founder. Every team is different, and “alphaness” is a shifting role that depends on circumstances. The real challenge is to balance the open exploratory creative space with the finality of locking things down, making hard choices, and sticking to them.

Eight months in, and still without the clarity we sought, we decided to give ourselves a deadline: we’d have a pitch and start looking for funders in three weeks. We’d have to own the idea completely in order to confidently pitch it, so this was a good litmus test for our desires. A week later, after many discussions of our interests and values, of where we’d been and where we wanted to go with our careers, we decided to call it quits. I’m proud of us for walking away from something that wasn’t working, and for remaining close friends through it all.


Lessons Learned

  • Your process is your own. I love that Lean Startup exists. I love that the processes have been formalized and written down for the sake of managing the chaos of a startup. This is a great new development. But process is too important to delegate to any book or method. Bruce Mau: “Process is more important than outcome… If process drives outcome, we may not know where we’re going, but we will know we want to be there.” I think that’s very appropriate for startups.
  • It’s a very personal journey. You will hit personal boundaries and weaknesses really quickly and repeatedly. If you’re willing to listen, you’ll learn a lot about yourself and hopefully adjust in time. What you learn about yourself may turn out to be your best outcome from the startup.
  • Too much openness will kill you. You can’t continue to stay open forever and expect to get somewhere. Especially around vision: it needs to be locked down early, so you can focus on the nuts and bolts and really make headway in understanding the product/market fit for a given instantiation of your vision.
  • Conflict is so important. There’s deep honesty in conflict done well. You can avoid a lot of blind alleys by closely examining differences. It pushes you through barriers.
  • Questions must remain unanswered. You will never be able to answer all the critical questions. It’s easy to question things at too high a level when you should just charge ahead, at least until you gain momentum.
  • Have a third person around. If you are working with only one other person, you should have a third person with whom you meet weekly. This person’s job will be to call you out on whatever bullshit you and your co-founder have convinced yourselves of in the past week.
  • Idealism is good. Yes, you will have to balance it with reality. But don’t lose sight of what got you into this in the first place. Startups really can change the world.
  • Process makes perfect. Amid the chaos, find calm in routines and processes. But don’t prescriptively follow someone else’s best practices. Take time to consider and improve your processes. Notice when they don’t work, and talk about it. Your process will be different from everyone else’s.
  • Fold new processes carefully into your working style. If you are taking up a new process for the first time, like Lean Startup, you’ll probably start by fully adopting it and pushing hard on the boundaries. But at some point, you need to take the best bits from it and incorporate them into what you already do well.
  • Find lots of alone time. William Deresiewicz is right about the value of solitude. Take long walks. It worked for Thoureau, Gandhi, and Jack Dorsey.
  • Frequent changes of your vision are not “pivots.” Pivots are changes in strategy toward an existing vision.
  • To learn about the problem, build. Keep iterating, on paper or on screen, at whatever resolution you can manage. The cycle of design-prototype-test will help reveal what you’re doing and why.
  • To develop an elegant solution, build an inelegant one first. You have to start somewhere. Just start! Why are you reading this list! Go do it.

Thanks to Siobáhn Cronin, Rahmin Sarabi, and Jacob Gordon for feedback.

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