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Write the story you want to tell

Rails/Angular developer, Entrepreneur & YC alum. Previously built and sold Clickpass.com. Now O(only)TO at Brojure.com and part time partner at Entrepreneur First.

Every time I pitched my last company, Clickpass, I ached to be telling a story I hadn’t written. I desperately wanted to say how “we did this and learned that so we did the other”, the problem was, we hadn’t. We spent a long time building something that we didn’t expose quickly enough to the public and weren’t fast enough to change once we did. 

One day, in the hope it would make our investment story a little more interesting, Mike Maples sent me and Immad to the IMVU offices where we listing avidly to the (not yet famous) Eric Ries as he told his now fabled account of their beginnings.

Unlike most startups from whom you hear little except funding and exit, the IMVU story was written in its middle. Authors worry a lot about the last paragraph and as entrepreneurs we worry a lot about the final exit. You live a story in the two thousand paragraphs of the middle, not the last one and you live a company in its building, not its exit. 

IMVU was fascinating because it was a shaky start, a great middle and I don’t even know what the ending was but I sure as hell remember the story. If there was success to be had in the market, their strategy made that success almost unavoidable and exit a detail rather than a destination.

IMVU made me want to take control of our narrative. I yearned to show how we too were making success inevitable. Unfortunately, the story we’d written was dull and our success was anything but inevitable.

And when I say “we’d written”, I mean “I’d written”. My team was good. Extraordinarily good. So good I groan at not having had the experience to realise as much at the time. Immad was the best developer I’ve ever worked with and David was a simply incredible designer.

I was however not the best CEO. Not the worst but not the best. I was very inexperienced and, like many CEOs, very, very frightened. I’d forgotten just how consistently frightened until meeting an old friend with whom I’d hung out in our YC summer of 2007. She laughed when I made some reference to feeling more relaxed this time round and reminded me how I’d once mentioned waking up every single day that summer feeling utterly terrified.

She was right. I was scared. Very scared. I was scared for a lot of reasons but the main one was that I didn’t know where we were going. I didn’t know where to lead us and so I couldn’t. I didn’t know what story I was writing.

So in building my new company, Pingpanel, I’ve taken to writing the story of the company as it grows. Every time something interesting happens, a big release, new customer, a potential new hire, fundraising etc., I write it down and on the first of every month I tell the story via email to my angel investors.

The interesting effect of telling the story is that it forces you to write it and not just write it but write it well. Everyone wants to tell a gangbuster of a story and knowing you have to tell one creates a back-pressure that forces you to write one. Too often we thread our narrative retrospectively, an apologetic answer to a forlorn pitch deck. 

By building the pitch deck live I build the deck, and the company I want to present. What have I done this month that’s worth a bullet, worth a slide? Would I really want to explain how those four weeks disappeared without even a footnote to show for them? Not that I’m focussed on investment, far from it but there’s nothing like asking someone to part with their cash to clarify the reasons why they should.

When in doubt as to what I should prioritise, I now ask myself what will make the most compelling retelling. Is the audience really baying for a montage of coding or is it clear to all that I’m just avoiding cold-calling? Is the order-book overflowing and should I really keep selling or would the rational listener not just ask me why I didn’t get out and recruit? 

I can always rationalise the work I’d like to be doing but the pride or guilt that accompanies an imagined retelling is a great indicator of the work I should be doing.

It was therefore with a smile that I read Pixar story-boarder, Emma Coat’s 22 Rules of Storytelling. If you haven’t read them, do so: they’re great. They’re also incredibly applicable to a startup. Or to life. If only to avoid Ben Mezrich adding his own dramatic falsifications, I recommend becoming the author of your own narrative.

If you liked this you might also enjoy: The 22 rules of Startup Storytelling