some key lessons i have learned from twenty years of success and failure as an entrepreneur.


insecurity drives me. i used to think i was afraid of failure, now i think i am more afraid of success.

i am never fully successful, but i always soon will be

i never know enough about what i am about to do

we all get old, our kids grow up in front of us, our relationships mature and take unexpected directions, some ebb away

computers are coating everything we do, all the time, everywhere we look

all we have is our ideas, our emotions, our ambitions, our relationships, our time, our attention

i am 43. most of the people that i work with are in their late 20's

what will my team remember about me? that i had vision. that i was intense. that i was a teacher. that i tried to do too many things at once.

my job is to be concerned when things are going too well, and confident when things are going too badly. like a shock absorber.

money is not the goal, its just a means of helping you work on what you want, with whom you want, when you want

i doubt i will ever give up trying to create something new

when i am anxious or afraid i tend to make impulsive decisions

sometimes i am too impressionable and act on the last thing that somebody told me


start a company when you envision an inevitable solution to a problem that is getting bigger

keep your head up, and make people laugh. if you are not approachable, you will not get valuable feedback. mbwa = management by wandering around

whether expressing or denying our emotions, they drive our actions.

put each person in the right role, surround them with great people, and focus them on a meaningful goal

your company is an expression of your desire to create something bigger than yourself

teach people how to use their unique skills to create something new

if you are at ease and confident in your decision, why ask for feedback? you will get some, and then you will frustrate the person who gave it to you.

follow your vision with absolute conviction, but make sure you listen for advice on how to get there

have difficult conversations now. and keep having them.

make sure your team feels comfortable enough to tell you the things that they think you don’t want to hear

delegate don’t abdicate


culture is like concrete: if you wait too long to set it properly, it will be impossible to reset later on

focus on making employees feel like owners

titles cost you nothing, but its dangerous to over-inflate them

smart goals- specific / measurable / achievable / realistic / time-based

call everybody a co-founder, as every member of a great team is constantly finding new ways of adding value

allow team members to award each other stock: it enhances the feeling of ownership and clarifies where respect is earned in the org

some of your early co-founders will not be around for your later co-founders. it’s ok.

if you do culture right, you won’t have to ask your team to work hard. but you will need to help them prioritize.


hire people based on three criteria: do they have unique skills? are they willing to do what’s necessary to win? are their values in line with yours?

find people that are hungry to succeed, identify what they can do uniquely well, and put them in roles where they can perform best

only work with developers who are driven to create applications that make users happy. give them the space they need to code.

B players turn A players into B players. remove B players.

take chances on people who have big chips on their shoulder- failing, being doubted, needing approval…

the ideal team is big enough to build anything you want, but not so big as to be able to build more than you need.


investors are like step parents: they care about you but you are not related to them

there is nothing like numbers to ruin a good story

it’s not about the money, it’s about the money

raise money when you can, not when you have to

dress british, think yiddish

focus on the individual investor, not the firm

unless you are exiting, don’t over optimize around valuation.

startups fail because they run out of money

in a bull market, lucky people think they are smart


your goal is to make people smile when they experience your product

the right user interface will permit you to add features over time without complicating the experience

find an exceptional creative developer, give him the support he needs, and challenge him to build something that he will be proud of

as somebody once said, if you aren’t embarrassed by your first version then you waited too long

better to add features after launch than remove them