What Gossip Girl taught me about entrepreneurship


What can a primetime TV show about the drama-infused social lives of 20 year olds living in the Upper East Side whose great-great grandparents had so much money that they don’t need jobs teach about success in entrepreneurship?

Not even a very nice car...

Not even a very nice car…

Enter gossip Girl: a revealing glance into the seemingly-glitzy, yet actually completely eff’d-up lives of people who have nothing but time on their hands and money in their wallets.  And what do they do with time when they’re not shopping for the perfect Patek Philippe to match their exactingly-chosen two-button, peak-lapel Canali suit, paired boldly with Salvatore Ferragamo Corrado shoes, Hermes Arc en ceil tie, Tiffany Metropolis cufflinks, and Ralph Lauren Purple Label Aston Gingham shirt?

Systematically fucking each other over, that’s what.

Ceaseless love triangles (I think there were a few love quadrilaterals), occasionally with someone from–gasp!–Brooklyn!…

…faux, fluid friendships formed around manipulation and chicanery…

…all for the sake of being the “it” girl…the “queen bee”…or using their trust funds to start companies with the purpose of proving to the world that they can “do it all on their own”.  …wut?…

…all neatly compacted into 1-hour segments that I like to watch on Netflix when I’m bored.

I hadn’t watched Gossip Girl for about a year, until it popped up as a recommended video on Netflix.

“Do I want to get myself back into this?”, I pondered…”‘cuz you know when you start, you’re not gonna stop watching until the very end.”

“Fuck it”, said I, and I took the plunge.

Sidenote- please do not think poorly of me, a 23 year old guy, for watching Gossip Girl.

Me excited after a Gossip Girl episode.

Me excited after a Gossip Girl episode.

My official excuse: Gossip Girl is not only an extraordinarily revealing commentary on the lives of rich people (though, for all I know, they’re making it up), but also exudes immensely cunning interplay between the main characters.

Or something like that.

But I will have you know this:

What I learned about entrepreneurship came from exactly that: the immensely cunning interplay between the main characters.

And in that sadistic, cynaical cunning emerges a lesson that I use today as I launch my Kickstarter campaign.

Get a load of this:

NB- If you’ve never seen Gossip Girl before, a.) I’m sorry, and b.) when reading this, just know that these people are all really rich except for where explicitly noted and enjoy screwing each other over…should be enough info to understand what I’m talking about.  Thx, -ed.

In Season 5, the Van Der Woodsen (Lilly, the mother; and Serena, the daughter) meet, for the first time, Serena’s cousin, Charlotte (Charlie) Rhodes.

Oh what an exciting occasion!..except for one thing.

Charlie Rhodes wasn’t the actual Charlie Rhodes…this Charlie Rhodes was hired by the real Charlie’s mom (Lilly’s sister, Carol) to get her little fingers on the real Charlie’s trust fund.

Problems like this--only even more first world than this meme--are the bulwark of a Gossip Girl episode.

Problems like this–only even more first world than this meme–are the bulwark of a Gossip Girl episode.

The real Charlie Rhodes was…as it turns out, attending acting school in NYC, completely oblivious to what was going on.

The question quickly becomes: how does the fake Charlie Rhodes–really a working-class girl named Ivy Dickens who is enamored with her new Upper East Side life–keep her cover, especially when A.) Ivy’s old, vengeful boyfriend from LA “happens” to run into her in NYC, and her boyfriend meets and befriends Serena??

The boyfriend quickly figured out the ruse, and feeling vengeful (and looking to make a slick buck in hush money),holds it way over her head.

When you’re committing identity fraud, have an angry ex-boyfriend actively trying to screw you over,  what do you do?

You plan way ahead, that’s what.

And it works marvelously.  When finally confronted by Max in front of Lilly and Serena, Ivy stunningly convinces them both that Max is lying (despite all of the evidence to the contrary).  She does all of this on top of actively pursuing social stature in the almost CIA-style researched gossip scene that is the Upper East Side.

And even when it’s once-and-for-all proven that Ivy Dickens is actually not Charlie Rhodes some 20 episodes after the ruse began (it became kinda obvious when the real Charlie Rhodes stepped into the scene), Ivy still manages to inherit most of the real Charlie’s grandmother’s estate.

If that’s not pro status, I don’t know what is.

OK, obviously this is scripted, and serves as a dubious proxy for a “real life” analogy.

But the extent to how Ivy was able to balance so many lies on top of each other…while simultaneously trying to become the “it girl”…is mesmerizing.

Take out the “cover up illegal stuff” part (and more importantly, the doing illegal stuff part), and you have an excellent Gossip Girl analogy to entrepreneurship that has served me well a million times over:

Plan ahead…way ahead…and line things up to fall into place.

All I know is it better involve alcohol.

All I know is it better involve alcohol.

When you woke up in the morning, do you know what’s going to happen to you today?

Did you plan out that you need to spend 3 hours today working on your venture sending out e-mails, because you need to have 10 potential customer interviews done by the end of the month, because you want to launch in March of next year?

Or did you think “maybe I should read more into this startup stuff when I’ve got a free second”, and get no reading done, but somehow found a way to spend 3 hours on Facebook?

At one time in my life, I sucked at planning and setting goals.  It cost me tons of time and almost-unbearable frustration.  I wasted so much time on a daily basis that I almost sunk all of my ventures.

But I don’t dance to that tune anymore.  Today, each and every day is structured with schedules that tie into mid-term tactical and long-term strategic goals.

In the time since organizing myself, I’ve gotten twice as much work done in half the time.  I don’t waste my time on things that don’t matter.  I do only what’s important.  That’s allowed me to recruit beta testers for Focosos, design a website for FusionCase (my Kickstarter project), and write this blog, all at once.  I have time to line everything up the way I need, which increases my odds of success.

Take FusionCase

FusionCase will launch on Kickstarter on January 30th, 2013.  Today is January 18, 2012.  Notice I’m out here promoting my Kickstarter launch 44 days before it will ever see the light of day on Kickstarter.

kickstarter-logo-k-colorAnd don’t think I’ve just been writing cute blog posts: I’ve been hustling around the Connecticut startup scene, meeting folks and building up behind-the-scenes support for our project.  I’ve been vetting startup groups in nearby NYC and Boston, and planning which meetings to go promote at; not only which meeting, but also what we’ll say, if we’ll have a booth, etc.  (My detailed marketing plans, strategy, and results are shared in-depth with members of the Kickstarter Insider’s Club; sign up here if you want to be a part of it).

Those truly in pursuit of startup success don’t leave things to chance.  They plan.

If my Kickstarter fails, it sure as hell won’t be because I left something on the table.

It worked–somewhat exaggeratedly so–in Gossip Girl.  It’s been working for me as I pointed out, and it’d work for you too.  I’ll be writing in the next few months about the specific planning that every entrepreneur needs to go through…stuff I learned the hard way when I wished I had someone guiding me as I guide you.

Let me leave you with 2 questions, tell me what you think in the comments below:

1. TV’s usually a waste of time, but have you (like me) learned something from a TV show that was actually useful (History Channel and Discovery don’t count!  We’re talking couch-potato comfort-TV shows only).

2. What do you find difficult about being organized?





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