A Guide to Career Hacking

It seems like every other week I am getting a call from an old friend or new introduction asking for career advice.  The narrative is usually pretty similar:  Smart people reach a certain point in their college education where they start thinking about career aspirations.  They look back at a couple years of miscellaneous coursework, and realize that they quite simply have no idea what they want to be “when they grow up”.

Our university system does an impressively terrible job of helping students iterate through career options.  Switching majors is somewhat stigmatized (which didn’t stop me from doing it three times in three semesters of school), and a huge percentage of majors do absolutely nothing to help students hone in on a career.  Students end up graduating feeling no closer to a career choice than when they started school.

I’ve had enough of these conversations over the past several months that I’ve finally decided to collect my general advice into a guide of sorts.  What follows is a mode of thinking about career decisions that has served me well so far.  As Brad Feld is fond of saying, “It’s just data”, and should be treated as such.

My advice is this:  Hack your career decision by rapidly iterating through several possible options.  Find industries that interest you, and hone in on testable ways to explore them as career options.  Check your assumptions about finances, time, and location to maximize your freedom to explore.  Finally, don’t be afraid to aggressively test these hypotheses, and be prepared to fail in doing so.

To do this, start by defining your interests:

1. Identify markets/industries that interest you.  I advise starting at the industry, rather than the job function level for several reasons.  First, job functions change dramatically over the course of a career.  You start as an engineer, get promoted to manager, and end up as an executive.  You start in marketing, move over to sales, and end up in business development.  So driving towards a potential function is often counterproductive in the short term.  Second, industries in which you have a genuine, long term interest are likely to keep you engaged regardless of the actual function you are fulfilling.  In my time at Onswipe and Taykey I’ve done everything from sales to hiring to project management, and thoroughly enjoyed each one.  This is because I had already discovered a passion for the overall industry in which I was working.

2. Hone in on testable experiences.  Prior to dropping out of college, I had three opportunities under consideration.  The first was the three month Associate position that I ended up being lucky enough to receive at Techstars.  Second was being an apprentice to an individual who led leveraged buyouts of distressed corporations.  Third was working for a military contractor in Afghanistan, doing QA on vehicles returning from combat situations.  These options were quite literally all over the map, but that was the point.  Each represented a bold, aggressive move into an industry that interested me, and each was an opportunity that would have been impossible to pursue in the traditional college framework.

3. The three month hypothesis.  Focusing on the Techstars opportunity, I knew that I needed to test whether tech could truly be a long term passion for me.  This meant taking a tremendous leap of faith:  three months in NY, no salary, and no guarantee of a job offer upon completing the program.  I planned a budget which allowed me about fourteen weeks of runway, and arrived in New York with my laptop, five changes of clothes, one set of sheets and one towel.  I planned and executed a lifestyle designed to minimize distractions, and worked 18 hour days, 7 days a week to maximize my exposure to mentors, founders, and learning opportunities.  The entire strategy was unsustainable on a long term basis, but that was precisely the point.

After defining my interests, I had to check my assumptions.  Overcoming your core career and lifestyle assumptions is the first step to actively hacking your career options.  These assumptions often fall along three lines:

1.  Finances:  What is your financial position?  Do you have savings?  Debts that can be deferred in any way? What are your living expenses?  Where can you eliminate inefficiency?  I was lucky to have several advantages in this regard:  I was intensely debt intolerant, and had chosen a State school specifically to avoid quickly being saddled with large student loans.  I was an inherent workaholic:  The summer after my Freshman year of college, I worked two jobs nearly full time:  From 9am to 4pm I handled the marketing for a SaaS software company, and from 5pm to 1am I worked as a waiter at a local restaurant.  Consequently, I had saved up enough cash to make an aggressive decision like moving to NY.

2.  Time:  Perhaps the biggest lie of American culture is the concept of the linear lifestyle.  You graduate high school and go to college.  Graduate college, get a job.  If you’re a high achiever, return to school for a graduate degree.  Back to work.  Get married.  Have kids.  On and on and over and over again.  The faster you can separate yourself from that mode of thinking, the better off you will be.  Taking three months at age 20 to pursue a potentially life changing career opportunity absolutely cannot damage your long term prospects.  When presented with a choice that has enormous upside, and a tremendously limited long term downside, you take it.

3. Location:  The geographic “hub” effect is as strong as ever, regardless of how social technology has changed the way we communicate.  I wanted to work in tech startups, and lived in Raleigh, NC.  I knew I needed to  relocate in order to accelerate my career, especially if I was going to pursue a three month hack.  I hear from too many students located in places like Atlanta or Madison who want to work in tech startups.  My first advice is always to move to a hub as quickly as possible.  You simply cannot replicate the serendipity and opportunities that come with living in New York or Silicon Valley.  Regardless of the industry you want to hack, find the hub and move there as soon as possible.

Once you’ve defined your interests and checked assumptions, you should have developed at least one testable hypothesis worth pursuing.  Having settled on the Techstars Associate position as my top choice, I simply had to go out and execute.  As always, this is the hardest part.  I left my friends, girlfriend, and network behind in Raleigh, NC.  I moved to a city I had never even visited, knowing that I was about to burn through every penny of savings I had worked so hard to accrue.  I threw myself into an industry I knew almost nothing about, in an environment where I was the youngest person by at least half a decade.

I was lucky enough that my first test ended with a “success” in the traditional sense.  I found the industry I loved, and received my dream job offer from Onswipe within less than a week of my budgeted runway coming to an end.  However, like any good experiment, an alternative resolution could have equally been seen as a success.  I could have found that I had no passion for the tech industry, and received no dream job offer with impeccable timing.  This would not have been a failure, but simply a refutation of my initial hypothesis.  With a relatively minimal time investment, I would have narrowed my list of potential career options, and learned an enormous amount in a short period of time.

Although these “hacks” are built around short term tests, they are not at all designed to optimize for short term success in the traditional sense.  This is no get-rich-quick scheme, or a way to circumvent paying the dues required to advance in your chosen field.   The primary goal is to learn, not to quickly make money or get a dream job offer.

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We Rejected Dan Shipper (And What I Learned About Hiring)

Edit:  To clarify some confusion over on Hacker News: Dan reviewed this post in its’ entirety before it was published. I gave him final say on whether or not it was published or submitted here.  He thinks the entire thing is pretty funny and will probably jokingly hold this over my head for months.


Last Thursday I jumped over to Twitter and saw this via my friend John Exley:



I was  blown away by the post and thought it was great to see this sort of thing written about an awesome guy like Dan.  I agree entirely with Jason Freedman’s thoughts on hiring, and loved seeing him put everything into his strategy of courting top talent.  It was cool to see Dan earning some (well deserved) attention for the following he has built over the past 2 years through his blogging and various projects/products.

The story also was cause for a little humor and embarrassment on my part.  See, a little over one year ago Dan Shipper applied for an internship at my last company.  And we rejected him.


Dan applied via our jobs page.  His application listed some interesting experience (Blackberry app development when he was still in high school, two small webapps), but nothing immediately relevant to our needs.  He also listed a few things that seem funny to look back on now:  His first semester college GPA, and his role as high school senior class president.  Altogether, it was an interesting application- but quite frankly, not very different from many similar applications we received from college students looking to work at a startup.  I sent him a quick response thanking him for his submission and looking to schedule a brief interview.

Here’s where Dan began to differentiate himself.  He followed up persistently (we were in the middle of Techstars at the time and had trouble coordinating an interview time), and kept me up to date on the explosion of Wheremyfriends.be, a simple webapp he had built with his friends Wesley and Ajay.  We finally found time to schedule a lunch, and he and I ended up spending half of an afternoon talking about product, startups, and education (I had recently dropped out, while Dan was committed to staying at Penn).

After our long conversation, it was clear that Dan had the mentality and intellect of an A Player.  He was young, driven, and extremely intelligent.  But in a review between myself and the company cofounders, one sticking point kept coming up:  Not enough relevant development experience.  We were trying to build a core front end team that had an existing passion for mobile/tablet, and Dan was a square peg in that round hole.  So we rejected him.

Rejecting someone you genuinely liked interviewing is tough, and I thought the least I could do would be to introduce him to other internship opportunities that might be a good fit.  I connected him with the awesome founders of Artsicle, where he ended up interning for the summer. Dan was extremely gracious about the entire thing, and I was happy to see him end up in a good situation.

Of course, looking back on it, the fact that we rejected the guy who is now being publicly courted by a well regarded startup like 42Floors is pretty funny.  However, in reflecting on this story, there are a few important lessons to learn as an early stage startup:

1. Look for talent at all levels: At the time that Dan applied, we had no plan in place for hiring technical interns.  We were focused on building out our “core” tech team, and really weren’t prepared for talented but raw engineers to step in and contribute.  We ended up rectifying this situation and finding two incredibly talented engineering interns, but we missed on Dan and several other potential candidates.  In a startup environment that is a constant battle for talent, early stage companies simply cannot afford to pass on talent at any level.  When we were absolutely buried with product needs in the weeks leading up to launch, we wouldn’t have given a damn if Dan did or didn’t fit our neat round hole of a job description.

2. Always hire A Players: This is repeated often enough that it’s a truism in the startup community, yet we still got this one wrong when it came to Dan.  As a startup, if you have the opportunity to bring on an A player in a low risk role (like an internship), you do it.  No questions asked.  Because finding A players is tough.  When one drops into your lap, you don’t hesitate or shuffle through your available job listings.  You pull the trigger.  In a company of less than 10 people, A players will naturally fall into the role that best suits them.  They will contribute at a high level, and attract other high level contributors to join the team.

3. Treat People Right: I could have easily made the mistake of sending Dan a polite rejection email and nothing else.  Instead, I followed up and worked hard to help him find another opportunity that made sense.  We got coffee the next time he came to the city, and met up when our schedules allowed over the summer.  I took something that could have easily been a negative interaction and turned it into a positive opportunity to build a friendship.  Whether we end up working together, competing, or just staying in touch throughout our careers, it’s great having a smart friend just an email or phone call away.


In our email banter about the blog post and subsequent Techcrunch and Hacker News coverage, Dan joked that maybe I finally owed him an apology for our rejection.  Even though that statement was made entirely as a joke, I don’t mind eating crow:  Like 42Floors made their offer as an open letter of recruitment, consider this my open letter of apology.

Making decisions in a startup is hard, and you absolutely cannot get every one right.  I’m lucky that this mistake turned into a positive (and humorous) learning experience.  Congratulations to Dan on one hell of a year, and best of luck to Jason Freedman and the team at 42Floors in courting A Players like Dan.





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