The LinkedIn hack that turned a penny into $100,000

Today, Jack Smith is an advisor to Shyp, a successful packaging and mailing-on-demand startup that just raised a sizable $50 million.

But back in 2011, he was the co-founder of Vungle, a new London-based video advertising startup looking for seed funding. And when they heard about a new startup accelerator program called Angelpad that was offering $100,000 to young startups, they knew they wanted in.

The problem was that Angelpad had over 2,000 applications for the one remaining spot. The chances that Vungle's application would even get read, let alone accepted, were slim to none.

And so, Smith turned to extraordinary measures: Breaking the rules of the then-new LinkedIn advertising system to create an appeal for entry into the program that only Angelpad founder and ex-Googler Thomas Korte would see.

"Hustle means finding out the rules of the game you're playing and breaking them," Smith told a crowd at today's HustleCon event in San Francisco, where startup founders share successful tactics.

LinkedIn was the obvious choice for this experiment because it was less crowded than Google or Facebook and easier to target, Smith says.

Smith went through a trial-and-error process of figuring out what he could get away with in a LinkedIn ad, which is definitely not designed for this kind of individual targeting.

For example, LinkedIn wouldn't approve any ad with a direct link to Vungle's appeal to get into the Angelpad program, so he used a URL shortener and changed where the link went after it was approved.

"I love breaking websites," Smith says.

More importantly, Smith figured out the hard way that he couldn't target a LinkedIn at just one company - in this case, Angelpad - and that the minimum target was seven companies. Listing Vungle itself as one of the seven, he now had to target it at 6 other companies.

Smith opted to aim his ad at Angelpad, as well as a selection of Korte's ex-coworkers, colleagues, and investor friends.

The ad itself? A big picture of Korte's face:

If you clicked it, it took you to a video landing page, where Vungle co-founder Jaffers explained why he thought the company was a great fit for Angelpad:

Korte's friends who were targeted by the ad all called him, extremely amused by Smith's hustle. He gave in and e-mailed Vungle back:

"You got my attention, that's cool, but take it down now," Smith recalls Korte telling him.

At the last second - literally days before the Fall 2011 class started - Korte and the Angelpad team took a chance and let Vungle in. The additional wrinkle was that the program needed the company to move to America, permanently, and within those few days it did.

The punchline to all of this is that because LinkedIn (at that time) let advertisers pay per 1,000 clicks, and only Korte had clicked on it, the cost for them to get into Angelpad - and get that $100,000 - was one single solitary penny.

Since then, Smith and Vungle used similar LinkedIn ad tactics to get the now-defunct Color Labs as a client, at a cost of $2.78. It worked on Spotify ($16) and Angry Birds developer Rovio ($3.24), too. He says that LinkedIn has since gotten a lot more strict about what it approves, but it was good while it lasted.

One time, he recalls, a lawyer threatened to sue, but Smith told him it was fine, only the company could see it, and asked to speak to someone in business development.

"And he did," Smith says.