How I Inadvertently Ran an MIT Student Hacking Contest For $3,001

It was 6:30pm on a random Tuesday evening in Cambridge. There I was, carefully counting a wad of crisp $100 bills in an unmarked white envelope.   I was parked in my car on Main Street, a block from the MIT campus.  The bills were new enough that they sort of stuck together.  The first time I counted them, I counted only 28 and had a brief moment of panic. There were supposed to be 30.  But, two more recounts, and I was fairly certain that there was $3,000 in the envelope.  This was the closest I think I've come to feeling like I was doing something illicit.  I was just waiting for a police officer to walk up to the car and tap on my window.

I was scheduled to hand this cash over to people I had never met.  At 7pm.  In a classroom at MIT's Stata Center (it's the building that Frank Gehry designed that looks like it came out of a Dr. Seuss book)

The $3,001 was payment for what was intended to be an inbound marketing contest.  The funny thing is, I inadvertently ended up running a hacker contest.  But, looking on the bright side, the payment could have gone as high as $50,000 (which would have maybe required a black briefcase and sunglasses).  So in some sense, I got off easy.  "This could have been much, much worse," I told myself.

Here's the story of how I ended up handing an envelope full of $100 bills to two complete strangers.

The Founder's Journey Class at MIT

Back when I was a grad student at MIT (this is back in the 2005/2006 timeframe), I took a class called “New Enterprises” with Ken Zolot and Howard Anderson.  It was the class to take if you were a student at MIT and had entrepreneurial leanings.  It's where I wrote the original business plan for HubSpot (the only business plan I've ever written).

Ken Zolot went on to teach a new class called “Founder's Journey” (6.933) .  Students were primarily undergrad computer science majors.  Ken invited me in as a guest speaker, and I've been a regular guest lecturer ever since.

My topic at this guest lecture  has generally been inbound marketing.  To make things fun and interesting, I often hold a small contest/exercise during class (I've done this in other classes I teach as well).  The cash prize was generally between $20 and $100 (usually based on how much cash I had in my pocket at the time, and the nature of the exercise).  It often involved some sort of inbound marketing task:  Write a title for this blog post, figure out some SEO keywords for this company, etc.

 “Hey, why don't we make this more interesting…”

A week before I was scheduled to speak to the current Fall term class of “Founder's Journey”, Ken reached out to me and suggested we might want to try a more “in-depth” exercise.  Something the students would have a few days to complete, instead of a few minutes in class.  I thought that was a good idea, and noodled on the idea a bit.  I then sent Ken this fateful email.

I will summarize the rules for you:  Each student first sets a goal for themselves in terms of how many retweets they're trying to get.  They then try to post a tweet that gets that many (or more) retweets.  Simple enough, right?

Now, the astute among you will immediately recognize a couple of issues with this proposal:

1. I don't specify a maximum payout.

At the time, what I had in my head was: “It's kinda hard to get people to retweet something that much.  I have 160,000+ followers on twitter, and even one of my popular tweets might get 100–200 retweets.”  None of these students is going to have that kind of following, ergo, the likely payout will be $20 –  $50.  And, if someone's really good and gets a couple of hundred retweets, so be it.

2. I'm not explicit about what methods are considered legitimate/fair to acquire the retweets.

My topic was inbound marketing, and part of what I was hoping to  teach/convey is that a) it's hard to get people to retweet.  b) it helps to experiment with different kinds of tweets (humorous, useful, controversial, social good, etc.)

What ended up happening was this “perfect storm” of mistakes in structuring this exercise/contest.

“I thought to myself:  Self, we have a problem…”

So, on Thursday night (t minus 6 days to the class), tweets with the #foundersjourney starting showing up on my radar.  Not surprising.  That's the evening the class is held, so Ken had clearly given the students their assignment and the game was on.

Several of the tweets were amusing, like this one:

But, when I saw this tweet, I knew I had a potential problem.

Uh oh.  Exactly 300 retweets (as stated in the tweet) — all of them looking like bots.  That's when I thought to myself, “Self, we have a problem…”  I realized that I had not explicitly stated that one couldn't set up a robot army to do the re-tweeting (that kind of defeats the whole purpose  of the exercise, which was meant to be about inbound marketing).  But, the rules are the rules.  I had set myself up, and was prepared to pay the price.

Now, I just needed to figure out what that price was going to be.  So, I sent an email to Ken to ask the simple question: What were the top 5 retweet bids/projections?  (Remember, per the rules, I wouldn't have to pay out any more than what someone had bid).

"The top bids are: 50,000, 11,000, 10,000, 5,000, and 3,000", he said.  “Holy crap!”, I thought.  This is going to get interesting.

Later, I saw this tweet.

The tweet didn't have 3,259 retweets at the time — but it was climbing steadily.  The contest ran for 3 days, and as you might expect, I watched intently as the story unfolded.

Once the contest ended, I knew I was likely going to be out a fair amount of money.  I didn't know how much, because I didn't know what Paul's bid was.  But, I had a sneaking suspicion it was going to be relatively close to the 3,259 bid.

So, I figured, what the hell — let me just reach out to this guy and get the skinny.  It's also when I had the idea to write this blog article.  I figured “Hey, maybe we can turn this into somewhat of a happy inbound marketing ending. ”  I later learned that Paul and Tim (a classmate) had agreed to join forces and attack the challenge together.

30, Fresh, Crisp, $100 Bills

So, last night (Tuesday, December 5^th), I went in to teach the Founder's Journey class (as scheduled).  I met Paul and Tim for the first time, handed them an envelope with 30, crisp $100 bills, while their classmates looked on with a combination of admiration and envy, and then went about my business of convincing a bunch of undergrad computer science students that marketing was usually necessary, and that inbound marketing was the way to go about it.

Paul tweeted a picture of the cash later that night.  Here's that picture.

Here's a video of them hacking away (don't worry, there's no sound, so it's safe for work -- or classrooms

CAPTCHAs, consoles and cash, Oh my!

I went ahead did an email interview (this is all before I actually met the guys).  Here are the questions I asked, and their responses.  Only minor editing..and I've added some of my thoughts in italics.

Closing thoughts and lessons learned