Rosen had been working full-time doing business development for a West coast startup, running around town trying to clinch deals, all so he could afford to spend his free time working on his own startup, Speakergram. Being a young entrepreneur was running him down.
“As luck would have it, that night I came down with one of the worst colds I’ve had in recent memory,” says Rosen, who estimates he was getting three hours of sleep a night between his day job and his startup. “After about a year-and-a-half on the grind, there have been multiple times when I was either a little tired or under the weather and thought about passing on an event or a meetup, but every time I ended up going because something in the back of my head said, this could be your break.”
So that Monday, Rosen headed down to General Assembly, the swank new startup space in Flatiron. Exiting the elevator, he could sense the buzz, and sure enough there was Dave McClure, one of the most prolific investors to come out of the PayPal mafia, surrounded by a school of eager young startups pitching him their projects.
When Rosen finally got his chance to chat, McClure was ready to leave, but he invited Rosen along to private dinner. The evening was packed, but two ended up sitting next to one another, and afterwards Rosen got a chance to demo Speakergram. It seemed like a great connection, but Rosen figured that was all. A few days later, his phone rang. It was McClure, offering him a chance to be part of his program, 500 Startups, a seed fund and startup accelerator.
“I was driving home and I remember thinking, don’t be such a fucking idiot, just call this guy and tell him to get his ass out here and stop wasting time with this bullshit,” says McClure. “It wasn’t the most strategic decision I’ve ever made, but I tend to go with my instinct. Sam had that starry startup look in his eyes, seemed like had been hoofing it for a while, and had built a product that addresses a problem I actually have myself.”
Speakergram, Rosen’s startup, is web tool for public speakers. Instead of struggling to juggle inbound requests, users create a page on Speakergram. Anyone interested in booking them uses that page to communicate dates, payments and other details. It’s a funnel and a filter that targets a specific group of users, the kind who are also happen to be terrific influencers and investors.
“Basically I said to him, how fast can you get on a plane?” recalls McClure. “I gave him the weekend to decide.”
Rosen did a quick gut check and pulled the trigger. He was leaving behind his girlfriend, his team and his day job for the chance to devote himself to his startup full-time. “My plan is to come back to NYC to run my startup, but of course, there are no guarantees,” says Rosen. “I think the number one thing I’ll get in California is the ability to dive fully into SpeakerGram and really give it my all. I’ll probably still only get 20 hours of sleep every week, but at least it’ll all be spent working on my company.”
bpopper [at] observer.com | @benpopper