The Start-Up Diaries – Volume 1


Monday – Must make a note of how this all began. I was staring down at the subway tracks, where my broken Blackberry was blinking its last gasps of life. The fifth phone I’ve lost this year. Noticed that as the sound of its clicking keys receded from my brain, a enormous calm came over me. Certainly my employer, one of the few reputable investment banks left in this town, would be happy to replace it. But not sure I really want it back. An enormous energy began welling up in my brain. Realized that what I need is a way to figure out exactly what I was doing in the moments before I dropped, then kicked, my Blackberry under the oncoming A train. Like one of those black boxes they have to on airplanes to record what happened before the crash, but this would be for my own life. Maybe, I found myself thinking, I could create a mobile app to do this. It could be a sort of personal archive, a security system and a social network. Suddenly realize I’m standing on the platform with a massive erection.

Tuesday – Cornered the squirrely looking IT guy who is always standing alone in the smoker’s corner playing with his iPhone. Sidled up and made casual conversation, sports, weather, then mentioned I had an idea for an new app that I thought seemed promising. “Is it a game?” he asked, not bothering to look up from his phone. Felt my temperature rising, but tried to remain calm and explain that it was a mobile, local, social network for users to archive, share and discuss moments of crisis in their lives. “You gonna make it?” he inquired. Took a deep breath and explained that I was looking for someone who knew about computer programming and thought that maybe he could help. He told me about an event happening the next night, Find a Co-Founder, that some friends of his from the start-up world were planning to attend. A rush of excitement comes over me. Must go home and work on a name.

Wednesday – Arrive early to the hip East Village rooftop bar where the Co-Founder event is being held. Took the day off work and purchased new iPhone, Droid Incredible, iPad and Galaxy tab. Joined a dozen social networks and improved my Klout score by six points. Haven’t slept in 36 hours. Read the complete archives of Fred Wilson, Paul Graham and Brad Feld. Experimenting with names for my app., and seem like front runners. A group of young, pale men arrives and head to the bar. I sidle up and hit them with my pitch. “I don’t see how you would tie that into daily deals,” says a tall, pimply one. “Do you have a LaunchRock page?” asked a fat, bearded one.  Explain that there is a huge market opportunity here, and recount the story of having to replace my Blackberry five times in a single year. If I could quantify the moments before each phone was lost, I explain, what might I learn about myself? “You have a Blackberry!” says the fat one, laughing. Explain that I’m a executive at a large bank. The group goes silent for minute before the pimply one blurts out, “Are you looking for a co-founder?”

Thursday – Emails are piling up from the office but I ignore them. Stayed out till 4am talking with @wizdev, I think his real name is Derek, the fat one from the bar, who I have taken on as my co-founder. Caught a few hours sleep and woke up to draft my pitch deck. @wizdev is a member of a new-coworking space, Bubble House, and has arranged for us to meet a prominent venture capitalist. According to Derek we should aim for a $500,000 seed round and then, six months down the line, an A round at $5 million pre. Need to get traction among influencers. Thinking @CharlieSheen might have a few moments he would like to review with Realized I know his broker and am reaching out for an intro.

Friday – Today is officially my last day as a banker. Have moved into Bubble House and stayed up last night having “idea jam” with my new office/roomates. @wizdev says the our seed round is on Angel List now and that the attention has been “huge”. Hoping to blow out the seed round to maybe $1 million and get the app ready in time to launch at SXSW next year. Fingers crossed that my girlfriend understands why we need to cancel our vacation to St. Barts. Trying to sort out the difference between Ruby and something called Mongoose DB. Considered e-mailing some of my old co-workers from the bank to let them know what I’m up to and ask for some input, but decided they would steal the idea, as our bonuses are not what they used to be. Plus, I haven’t felt this free or excited in years. #winning #byebyebanking #startuplife

Saturday – Disaster! Met with @wizdev’s VC friend, who turned out to be associate, not principle, not partner. He said that his firm has already invested in a similar service which is set to launch later this month. Also turns out Black Box has been trademarked by a daily deal service targeting the African-American surprise birthday market.  Domain names are already taken for and, a social network for the BDSM crowd. Told my girlfriend about postponing our trip, she asked why I hadn’t been home in days or, apparently, going to to work. Explained about the start-up and quitting the bank. Strangely, she began to cry. Felt a bit strange myself. Left the house for a long jog to collect my thoughts (track my progress on Runkeeper). Decided it’s time for a pivot.

Sunday – Woke up this morning to find one of my office mates at Bubble House has “rooted” my Android devices and jailbroken my Apple ones. Claims he was “liberating” them, but I’ve lost my notes from the last week and can’t seem to use either to connect to the web. Had a dream last night: I was wearing roller skates and doing some sort of dance routine. The crowd was chanting, “Pivot, pivot, pivot” and I jumped in the air, spinning around, but didn’t come back to the ground. I floated up through a opening in the roof and soared higher and higher. Woke up and realized the best part of the airplane ride is all the stuff that happens before the crash. Decided to change course and create world’s best flight simulator for tablet. Need to call @wizdev but all my phones are broken. Think I’ll go down to BestBuy and pick up a new Blackberry. The Start-Up Diaries – Volume 1