In January 2014, I submitted an entry to Berkeley’s Business Plan Competition. I spent 2 weeks writing 15 different versions of the executive summary, team description, and business model canvas. I didn’t make it past the executive summary stage, but the experience really helped me better understand what I was trying to build (including influencing early pivots).

I won’t talk about tips on what to write, there are a lot of really good posts already out there (this, this, and this), but I do want to point out two key strategies on how to write.

1. Say what you want to say (, record it), then write it — One of my managers gave me this amazing tip for explaining hard topics. First tell it to yourself out loud, you’d be surprised how many misunderstandings you’ll catch yourself making. Once you clear these all up, then you’re in a much better position to communicate what you want
2. Check-off the ideas you want to hit twice, as you’re writing and two revisions later — I made a list of the ideas I wanted to cover, and after hitting everything, I had written 3 pages. In the process of parrying down to the requisite single page, I actually lost many ideas. They were too shortened to be recognizable.

Finally, some of my favorite editing tips & tricks that apply to pretty much anything I write:

• Give yourself a rest day before reading the draft you just wrote — This lies very counter to my natural instinct to finish something and then stop. But nothing beats fresh eyes. Four of my versions were complete re-writes as a result of waking up and realizing that what I wrote before was not great.
• Read drafts aloud, with a pencil underlining every word — Combats the mental inclination to “fill in the blanks” and highlights basic syntax and spelling mistakes that you’re definitely making.
• Try to cut out “so,” “that,” “like,” — If it doesn’t sound polished in a speech, it doesn’t sound polished in writing either.