Learn on someone else’s dime

I remember being a senior in college and thinking about my possible career choices. After 16 years of school, I was just so excited to be working and out on my own.

But as I looked at all the jobs offered to me, none of them seemed glamorous enough.  I wanted to change the world, not be on the ground floor of some massive corporate ladder.  I’d worked way too hard filling myself with all this knowledge and experience to be working for the man.  I also kind of wanted to get into startups.  Not just into startups, I wanted to be running the startups.  But I really didn’t have a clue how, nor did I have an idea.  I felt lost.

And that’s when my dad gave me this little tidbit of wisdom:

Learn on someone else’s dime.


That was just the little nudge I needed to go look for an entry level startup job.  I found an incredible one—as an intern for a site called MocoSpace in Boston. At the time it was the largest social network focused exclusively on mobile, and I joined the company right after it had received its first round of investment from General Catalyst.

I pretty much did whatever the founders or the head of product needed me to do.  At one point, I was needed to go check out every competitor in the space and screengrab everything that happened on their site.  It was so mundane. I didn’t yet have the product expertise to design my own products, so the best I could really do was gather all the information so that the rest of the team could use it.




But while working for MocoSpace, I soaked up all the goodness of being in a startup.  I was there as we brainstormed new product ideas and got to watch all the different pieces of the team put them together.  Ideas spiked out, engineers working on them, feedback from customer service – the whole little machine of a startup was taking shape in my head.

I was there as we celebrated small wins like a conversion uptick on our login page.  Something I had never even thought people cared about.

I was there as our customer service team grew from 1 person to 5 people and Gmail started to fail them.  And then just as quickly resolved by installing a ticketing system.

And what made all of this so interesting was that the company was going through hyper growth.  The whole social networking industry was in its infancy, so every little decision mattered.  Because the company was growing so quickly, the problems we encountered changed day by day.  After a few short months the entire company had changed before my eyes.  It literally doubled in size.  And finally, feeling that I had learned enough, I decided it was time to leave and start my own startup. A few months later, we founded OpenVote.




Throughout each of my last three startups, little bits of wisdom gained during my entry level MocoSpace experience have been important.   MocoSpace was a really good company, so I didn’t learn a whole bunch of things not to do. And although they didn’t grow to the size of Facebook, they’re still a really strong company and I proudly copy as much as I can from how they built their team.  I’m so glad I had the opportunity to learn from them before going out on my own.

So if this resonated with you, here are a few tips for deciding which entry level job will be best suited for you.


Tips for Picking an Entry Level Startup Job

Pick a rocket ship

The single most important factor on whether you’ll have a good experience is whether the company you join is exploding with growth or not. Because when companies explode with growth, everyone who is entry level today will be experienced leadership three months from now.  There will simply be so many opportunities to get things done that you will have the ability to grab hold of whatever experience you want.  When a company is stale or declining, the inverse is true.  So irrespective of everything else, pick the company most likely to succeed.


Get in early

The best learning is when you get to see the company grow around you.  If the company already has a hundred or two hundred people, it may still be a startup, but it is really a late stage startup, and all of the tremendous learning opportunities are already gone.  When you join a company that size, you’ll get the benefits of a really good training program and you’ll surely work with outstanding people, but you won’t be a huge part of helping the company grow.  When there are just 25 people or less, nothing will be created for you and half your time will be spent building the company itself.  The risk goes up, but it’s certainly worth it.


Teach yourself a new industry

All too often I see young job seekers limiting themselves to products they’ve used themselves.  If you’re fresh out of college or even a few years into your career, don’t expect that you’ve already had your most important work experiences.  Just because you’ve done an internship here or a job there doesn’t mean you are already pigeon-holed into one industry.  At 42floors, almost all of us knew nothing about commercial real estate before we started, but each person that joins has to learn the industry quickly.  It’s actually a great way to start a job because you approach each problem with a fresh set of eyes.


Work with fabulous people

The actual job that you do may or may not be the perfect fit in the long run. A lot of our entry level jobs at 42floors are account management, which means spending a bunch of time on the phone. While you clearly need to be able to do that job, it doesn’t mean that is what you’re going to do the rest of your life.  Most of what you’re going to learn is through osmosis of the people around you.  So if you’re not blown away by everyone you meet during the hiring process, look elsewhere.  You don’t want to be learning bad habits, especially because you might not know at the time that they’re that bad.


Do one hour of research before you apply

Not only do you need to use the product and the competitor’s product, but you need to research the company itself – who the founders are, follow their Twitter accounts, read everything in the media. For one, it will help make you much more likely to get the job. But two, you want to really have a sense of who the company is because their story is going to become part of your story.  It only takes an hour.




And now a shameless plug.

42floors, my startup, is now hiring for a bunch of non-technical entry level positions (we’re always hiring hackers).  Our site is blowing up right now with massive demand that we simply can’t keep up with. We’re hiring as many account management specialists and sales people as we can – all entry level positions.  For those of you who don’t know our site, it makes it easy to search for commercial real estate.   And over the next year we need to reach out to virtually every landlord and broker in the U.S.  We’re going to build a really big team of people to do it, but right now the account management team has just a single person.  It’s going to be an incredible experience for whoever joins the team right now.  Not in 3 months, not in 6 months, but right now because right now is when you get to be there as part of the foundation.  The whole system doesn’t really work yet.   You’ll have to figure out everything as you go along. Not just like how to do the job, but also how to build up the team around you.

Megan started just last week and she is already busy interviewing and hiring for people to work with her.  You’d be doing the same thing. And all of a sudden just days into an entry level position you need to become good at interviewing because whomever you hire may work with you for the next several years.

Right now everything is run off a collection of inconsistent Google docs.  We just signed up for Salesforce but haven’t installed yet.  So just days into your job, you’re going to have to help us figure out how to make everything organized and efficient.

This team is going to grow to 20-30 people and we need your help to support that.  Right now our office is way too many desks jammed into a 2,500 square-foot unit (which by the way is still stunningly awesome – see the pictures here).  But we just signed a lease for a 7,500 square-foot kick-ass office in Soma, and we’re going to need your help to build it out for your team.

Startups are usually run totally flat and ours is an extreme example of that.   There will definitely be people to support you, but you have to be someone that is not only capable of figuring things out, but prefers it that way. And you have to be good at the job itself; you need to be able to pick up the phone 75 times a day and convert 90% of the time.  While you’re trying to master that, you need to be good at helping train the next person, and once you realize that that doesn’t scale, you also have to be good at developing a training program – and very quickly your job has changed three times.

It doesn’t matter whether you know about commercial real estate or not. We’ll teach you that part.  And it doesn’t matter whether you have experience in sales or account management. We can help you with that part as well.  But you need to love all things startups. You need to be super motivated.  And if you are those things, you should totally apply for a job here.



Discuss on Hacker News.

1 response
Jason, Thanks so much for the wisdom that you so often share on the blog. Sounds like your past thoughts about jumping into the startup game after college are similar to my current ones - dive in head first, learn as much as you can, and grow grow grow. I have an interview with Megan today and couldn't be more excited. Hope to meet you soon! Jacob