The Untold Story of Chegg PT 1
My name is Ousama Haffar and I was one of the early guys at Chegg.

While Chegg isn't a Zynga or a Facebook story that attracts the oohs and ahhs of Silicon Valley, I would love to share a bit with you about what I learned about entrepreneurship and being scrappy during my time at Chegg as founding member of the team from 2006-2010 and how we went from $0 to over $100M in revenue.

Chegg originally start its life as a college classified site that attracted 60,000 students across the country to buy and sell your everyday college type items; t-shirts, mini fridges, old beat up Pontiacs, etc. Our team was about 5-7 people, mostly engineers and I focused mostly on product, marketing and whatever odd jobs that needed a hand.

In our early days we attracted a couple hundred thousand visitors to our website each month, mostly buy building a campus marketing team and doing your traditional marketing. We would give away pizzas, flyer in dorms work with student organizations to create swap meets at the end of the semester and even created a textbook exchange.

Well, back in 2006 the name of the game in Sillicon Valley was user generated content and eyeballs. We dreamed of building this vibrant and massive classifieds business that could be monetized by advertising in each vertical in the already $200BN college market. In reality, we hit the same problem most marketplaces hit, the good ole' 80-20 rule. Users seemed to love browsing the site but never felt like posting items for sale. And as a result we hit a growth ceiling. Well, back in 06 and 07 with Facebook's popularity storming off and sites like Youtube changing the world, most web startups felt most strongly about generating users, and well when your user growth hits a wall...you're in trouble. So we did what any startup with a million bucks in the bank looking for quick fix to growth problems would do, Marketing Promotions.

So, me being the marketing/product guy thought hmmm...what would college students want that would make them tell all their friends and magically grow our user numbers overnight? In 2007 that answer was the hottest item on the market, the Nintendo Wii. So with a couple thousand bucks in hand and a skill for finding sellers of the hottest gift on the planet we went to work and secured a supply of 6 Wiis. Here comes the kicker, we planed a promotion to sell them for the insanely low price of $99 on our wonderful classifieds website and promote it using Deals of America, Fat Wallet and sending an email to our user base.

What happened was predictable, but nevertheless exciting. A fresh line of oxygen and the beginning of my misery. Within an hour after launching our promotion the website came to a standstill, our server couldn't handle the traffic and our best case scenario turned into a nightmare. Meanwhile, some college hackers thought it would be fun to hit our site with a D.O.S and as soon as we were up and attracting hundreds of thousands of users we were down and scrambling to get it back up and running. The pure exhilaration of seeing an idea become an instant hit to turning away tens of thousands of users was just a taste of the the roller coaster of emotions I would experience over the next 3 years at Chegg.

We finally got the site back up and running and within seconds the Wiis sold out. We thought to ourselves wow, our "Hatch of the day" as we called the promotion was a mega hit and it's time for us to start repeating it day in and day out. With a $50,000 budget I went to Frys, scowered amazon and found the most popular college items of the day and loaded a back room with marketing inventory for our daily deal sales. Within the week the website seemed like a vibrantly growing community, the word was quickly spreading and our story to investors seemed bright and optimistic, the day was saved thanks to the Hatch of the Day, or was it...

Part 1 of 6