How I Quit My Job, Moved to California, E-mailed Tim Ferriss, and Got Angel Investment


Don’t Quit Your Day Job

There’s a depressing old adage: “Don’t quit your day job.” It has the same ring as “You can’t fight City Hall,” it seems specifically designed to prevent people from trying.

I loved my job in Manhattan. I was an account manager at a Flatiron marketing agency called Mirrorball with a really awesome team and a great culture. It was a “work hard, play hard” ad shop with cool clients and fun coworkers. Then one weekend in May of 2012, I read Kill Your Inner Wantrepreneur and it got some gears turning. I had an idea for an event marketplace called Speakeasy. In retrospect it was really just a clever event ticketing idea, but I was determined.


A New Startup Idea

My roommate Anthony and I quickly covered the walls of our loft with post-it notes. We designed every screen, every feature, and every little use case we could think of. We were on to something, we thought. Anthony was a newly unemployed developer and I, a sales and marketing guy. I figured I could work nights and weekends, and maybe get somebody on oDesk to build the MVP and we’d see where it went. Anthony disagreed and said you never get any good work from freelancers, and we should work on it full time.

Each day at work the idea grew on me. I pitched anybody who would listen, and eventually I convinced myself this was such a great idea I should devote myself to it fully. Within a month I had given my notice at work, and committed to living on my savings for however long it would take.

The decision to leave New York was not hard. New York is kind of like a daily punch in the face, I am from there originally, and I was eager to check out the west coast.


Before our first investor meeting at First Round Capital. They said no.


Heading West

Two weeks later, we moved to California. We stayed with a friend in Potrero Hill while we were getting ourselves situated, and started emailing investors constantly. We must have emailed about 300, got lots of warm intros, taken some calls, had some meetings, but were always met with a polite no.

Bringing Them to Us

We remembered another old adage: “Work smarter, not harder.” With all Paul Graham’s advice about “hacking non-computer systems,” it occurred to us we just needed to do something that would get investor attention and make them come to us instead of emailing all of them.

We brainstormed for about a day before we came across the Dressrush deck, aka “the pitch deck heard round the world.” We had the idea of making a funny parody of the deck, but with even fancier javascript effects. They used impress.js, so we used a library called jmpress.js that allowed you to map your slides into 3D space. The resulting deck was pretty spiffy (broken link sorry) and kind of hilarious if you had seen the original deck.


Sending it Out

The next day, we wrote a blog post about the process and about our deck. Among the people I decided to send it to was Tim Ferriss, with whom I had a mutual friend, but it was still a pretty cold e-mail. I said something like, “Hey Tim, I heard you do some angel investing. Check out our deck and let us know if you’d like to chat.”

Tim replied about 6 hours later. He said he was going to pass. My heart sank a little until I read the rest of the e-mail. He said really liked the deck, and he tweeted about it.


What happened next was pretty surreal. Tim had about 500,000 followers at that point and this definitely got us attention. We received calls and emails from investors all over the country. One of the investors was from Southern California and he asked for a meeting the following week. We rented a car, drove down, and shook on it. The deal closed two weeks later.


As an aside, my biggest regret is that I didn’t read The Lean Startup before I quit my day job, but otherwise, the old adage is true: Work smarter, not harder. Use your time efficiently, find clever shortcuts, and you will be able to achieve the same tasks in a fraction of the time. I have no doubt we could have gotten investment the old fashioned way eventually, but when it comes to standing out from the crowd, this is the kind of hacking you should be thinking about.

h/t to r/startups for inspiring this blog post!

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