Over on Quora, Max Levchin provided a great response when asked about his greatest lessons in entrpreneurship:
Among Max Levchin‘s lessons learned as a young entrepreneur, which are the greatest?
It’s usually better to have a cofounder than go it alone.
Being an entrepreneur is not about being in love with an idea, it’s about being in love with running a company.
Having a highly homogeneous (background, education, values, preferences, etc) very early team is better than not — cuts down on time-wasting arguments.
You can have successful teams where people hate but deeply respect each other; the opposite (love but not respect among team members) is a recipe for disaster.
If there is any doubt about hiring a candidate for your first 5-6 positions, there is no doubt — do not.
You cannot hire a cofounder.
Do not allow senior managers to develop long-term grudges against each other. You will have to arbitrate those later, a huge time sink.
All compensation information eventually becomes public, and usually eventually == very quickly.
In many cases “working from home” is not really working.
Most often, when someone wants to leave your company, you should let them. Chasing them with offerings of money and power messes up the incentives of others.
Intra-office romance is usually (but not always) bad news.
Figure out one thing each of your investors is genuinely really good at, and insist they help you with that. Among other things it will save you from their help in other areas.
Consider on occasion whether the adjective “relentless” applies to your team. If not, you probably need to step it up.
Leadership by example is the most effective type. If you expect the troops to crank through nights and weekends, better be there yourself, even if you aren’t actually involved in the task at hand. It’s a little irrational, but it inspires people.
One usually raises money on great story or great results. Raise before, or right after launching. Don’t plan to raise a few weeks after launch.
Having a large and complicated cap table is rarely a good idea. Few committed angels is better than $5k from everyone and their brother.
Board meeting should never be product strategy debates. Double true that for product tactics.
Have a cardboard box at board meetings where attendees must deposit their mobile devices at the start for the entire duration of the meeting. At the very least suggest that idea.
Serve food at board meetings.
If you have a cofounder, give them a board seat. If you can, keep one more for yourself, and leave it empty. You’ll need it later.
Cofounders (under usual circumstances) should have same amount of equity.
Raising money between May 20th and August 10th, and Nov 10th through January 15th is somewhat harder than during any other time of the year — many VCs vacation during those times.
Never, ever agree to participating preferred.
Redemption rights are actually OK (it seems to be an East Coast thing), if placed a bunch of years out. Startups shouldn’t be in a limbo for that long anyway.
If you are going for a big raise at a huge valuation, consider the resulting pref overhang (and its impact on future employee motivation) very carefully.
You are not designing for yourself, and shouldn’t be. Most people using the Web don’t understand (most of) what makes it work and don’t want to. Design for those people — there are many more of them than you