When I was 19, I dropped out of college with my best friend, Wesley, to move to San Francisco and launch a tech startup called FamilyLeaf.
This might sound obvious in hindsight, but it turned out to be way more difficult than we assumed it would be, even with world-class seed investors and incredible support from everyone we knew. Startups are not glamorous. As inexperienced young founders, we were forced to grow up pretty quickly.
There were many surprising life lessons that hit us hard. For example, when trying to start a business, unlike school or even most jobs, there are absolutely no shortcuts to success. No element of “prestige” or “advice” will help your startup succeed in the Wild West of the open market.
Eventually, attaining achievements I thought were my personal, ultimate goals ended up being underwhelming.
Like a typical college kid, I naively thought having our names and website in the New York Times would bring us unbeatable traffic. New customers and users would flock to our website because they read about us in their Sunday newspaper.
But, when we were finally featured, it had no significant impact on our traffic.
Either people like your product and use it, or they stop using it and never come back; the New York Times does not have a say.
It’s something surprisingly hard for young, first-time founders (most of whom were stellar at “playing the system” of school) to get their heads around.
That being said, without early attention (good or bad), you won’t have any users at all. If you remember, before everybody and their little sister started using Snapchat, it was most notoriously known through a series of malicious articles for being just a “sexting” app.
All that parental controversy helped convince millions of rebellious kids to download Snapchat, and the rest is history. At the end of the day, startups live and die by self-promotion.
So, in our naive brazenness, we pulled off some pretty aggressive schemes to get more attention for FamilyLeaf and our other projects. You can argue that some of the stuff below was stupid, and I definitely don’t recommend doing any of it yourself. This is just one team’s story.
Even through the stupidity, at least we were resourceful and persistent, and through our experience, I learned those are the most important qualities when it comes to building a startup.
1. Ambushing A Famous Venture Capitalist At The Airport
My freshman year, I flew out to LA to check out Coachella. But, right before I left, Wesley and I learned (along with our friend Dan) we snagged a competitive interview spot for the startup incubator, Y Combinator, the following weekend.
We were planning to pitch a weekend project called, Readstream, but it was extremely beta and barely functioned at that point.
@ajaymehta yeah I'm here. Probably on the same flight back to NYC — Fred Wilson (@fredwilson) April 18, 2011
@ajaymehta I'm six rows back from gate 2 sitting next to @thegothamgal who has black and white hat on — Fred Wilson (@fredwilson) April 18, 2011
On the Monday after the festival, I was exhausted and waiting for my flight home at Long Beach airport. I looked up, and saw a face I vaguely recognized. It was Fred Wilson, an influential NYC-based venture capitalist I followed on Twitter.
Dan and Wesley had just sent over the latest build of our app, Readstream, and without even taking a look myself, I approached Fred and asked if he’d take a look at our new app and give us advice for our Y Combinator interview the following week.
I must have been an embarrassing combination of over-enthusiastic and dog-tired, but Fred and his wife, Joanne, were more than gracious in hearing out my amateur pitch and checking out the rough beta. Later that week, he retweeted Readstream to his 300k+ Twitter followers, and he introduced us to some very helpful NYC-based angel investors.
The Lesson: Even if there’s a strong possibility of you looking like a fool, don’t be afraid to put yourself out there. In a startup’s early days, lack of fear and resourcefulness can be your greatest assets.
2. Creating a Twitter Meme To Make Fun of the People We Were Hoping Would Invest In Us
While we were trying to prepare for our Y Combinator interview, Wesley had the silly late-night idea of creating a parody account based on the “Y U NO” meme that was blowing up on Reddit.
Wesley and I started cracking some very off-the-wall Internet humor jokes, and before we knew it, the account attracted follows from tech journalists and even YC’s own staff. Down the line, TechCrunch used the Twitter account as the frame for writing a whole story about our upcoming interview (honestly, I still can’t believe they published this).
The Lesson: The press is much more accessible than you might think. From the outside, getting a write-up in TechCrunch seemed to me like an impossible task. Yet, after just a couple weeks of tweeting insane jokes, there we were.
3. Wearing Handmade T-Shirts in Front of an Audience of the Best Investors in Silicon Valley
This one is self-explanatory. At the end of the Y Combinator program, there’s an event called “Demo Day,” where all the startups have the opportunity to pitch themselves to an intimidating room of the most powerful and respected investors in Silicon Valley.
We wanted custom t-shirts so they would remember FamilyLeaf, but we were too myopic to get them printed ahead of time. So the night before, we finger-painted ourselves some FamilyLeaf official tees.
The Lesson: Be flashy if you have to. Being memorable is better than being forgotten (in most cases). Still, in retrospect, we honestly probably should not have done this.
4. Translating Our Entire Website Into Chinese For One Good Press Story
My cofounder, Wesley, has family in China, and because so many social networks (like Facebook) are censored over there, it’s difficult to communicate with his family members online. So, we thought, let’s take advantage of China’s Great Firewall, and generate some attention by making FamilyLeaf available over there so other families like his could use it to stay in touch.
One problem: We first had to translate our entire website so Chinese speakers could understand it. We decided it was worth it. After a few long nights of translation (and many volunteer hours put in by Wesley’s dad), the site was ready.
We released it to the press and big tech blog Mashable wrote about it: "Facebook Photos Slip Through Great Firewall, Arrive in China."
The Lesson: Don’t be afraid to undertake ridiculous schleps to get some relevant press, or access to a new audience. Press angles are everywhere you look, but they require some effort to uncover. In the early days, do things that don’t scale.
Ajay Mehta is a technology entrepreneur and an early team member at Tilt.com, where he wears many hats. You can find him on Twitter at @ajaymehta.