Quick brain-dump of some clear, brutal lessons I have personally learnt doing a few startups over the past five years or so. I’ll maybe add to and unpack these at a later date, but these lessons are hard won.
Lesson #1 if it involves someone else’s copyright content, stay away. It will end in tears & disappointment.
Lesson #2 It can *never* hurt to spend an extra week or two just talking through the whole thing before beginning.
Lesson #3 If Google enters your space, pivot sooner than later. Seriously.
Lesson #4 Operate a single veto over senior hires – either total love or don’t hire that person.
Lesson #5 Get your employment contract and shares/options in writing, in clear language. Stick it on the wall.
Lesson #6 For all the user research in the world, if you wouldn’t use it there’s probably something wrong.
Lesson #7 As unsexy as it is, *start* with powerful email marketing and metrics systems from day one. Not an add on.
Lesson #8 If you are spending a week per month just covering your arse for the board meeting, you’re doing it wrong.
Lesson #9 A simple clear vision to rally behind is *not* optional. A startup tries out many things, but if they all align to the vision, momentum is never lost.
Lesson #10 Don’t put money in if you have talent (code, design, hustling, writing) – there’s loads of money around, not much talent.
Lesson #11 Avoid dilution with good employee share pools, and try not to accumulate massive liquidation preferences – you will lose interest when your potential upside < earning potential as a talented n.