The lack of a single, “the buck stops here” leader until too late in the game
No separation between the technology organization and the product organization=
Too much PR, too early
Too much money
Not close enough to the customer
Slow to adapt to market reality
Disagreement on strategy both within the Company and with the Board
Overto
Kiko
EventVue
RiotVine
Didn’t focus on learning & failing fast until it was too late
Didn’t care/focus enough about discovering how to market Eventvue
Didn’t make compromises in early hiring decisions – choose expediency over talent/competency
Weasable
And this worked really well for foursquare thanks to the mayorship. If I tell someone I’m the mayor of a spot, I’m in an instant conversation: “What makes you the mayor?” “That’s lame, I’m there way more than you” “What do you get for being mayor?”. Compare that to talking about Gowalla: “I just swapped this sticker of a bike for a sticker of a six pack of beer! What? Yes, I am still a virgin”. See the difference? Make some aspect of your product easy and fun to talk about, and make it unique.
On-Q-ity
Tigerbow
Sonar
Gowalla
Lesson learned:
Growth is the only thing that matters if you are building a social network. Period. Engagement is great but you aren’t even going to get the meeting unless your top-line numbers reach a certain threshold (which is different for seed vs. series A vs. selling advertising)
HelloParking
We felt that in order to survive we had to get our numbers up. We tried just about everything to juice growth, some ideas being more successful than others.
Everpix
GroupSpaces
Formspring
Standout Jobs
Salorix
Delight
FindIt
Findory
Exfm
I re-learned the importance of a team, one that balances the weaknesses of some with the strengths of another. As fun as learning new things might be, trying to do too much yourself costs the startup too much time in silly errors born of inexperience.
I learned the necessity of good advisors, especially angels and lawyers. A startup needs people who can provide expertise, credibility, and connections. You need advocates to help you.
Manilla
Blurtt
Skyrocket
Do not launch a startup if you do not have enough funding for multiple iterations. The chances of getting it right the first time are about the equivalent of winning the lotto.
Twitpic
Money stopped coming in the door.
In addition to a lag in sales, new product challenges arose and pretty soon I began to question myself. With each pitch following that period of doubt—whether it was to a girl at a party or an interested investor—my enthusiasm and perceived confidence dwindled.
