How To Create a Career in Startup land & Why I'm sleeping Above a Pub in England
Three Month's later, I've decided to write again
How? How, John, do I get a job at a startup? How do I apply? Who should I email? What should I say?
These are questions I hear almost every day from friends, colleagues, and even strangers I meet while traveling. The answer, my friend, is hustle. But when I say hustle, I don't mean working yourself to the bone in a dead-end job and hoping it pays off; most of the time, it won't. When I say hustle, I mean be direct in your communications and get creative with your strategy, all at scale.
Look, I'm not some boomer saying, "Listen here, kid, there are no shortcuts in life." What I am saying is, "Listen here, friend; there are no shortcuts to building a career that you want, you need to work hard to show your value and willingness to work."
What you must understand is; a startup is someone's baby, and it does not matter if I introduce you, the chairman of the board gets you in the room, or you get an introduction from Jesus himself, back to write you a kind two-line email, you are still going to be assessed on merit. Why? Hiring at startups is based on a simple question: can you solve a significant problem for us? If the answer is yes, you sometimes get a job; if the answer is no, you don't. Most of the time, there is not even a job open, but if you can show that you can solve a problem for the team, one might appear.
How do you show your value? Email the founder with the issue you have identified in their company and propose a solution. You probably won't get a response. Identify a new problem and send a new solution. On about the 8th email, someone might start to remember that you had half a helpful idea and shoot you a note, asking you if you might care to elaborate. At this point, you still won't have a job; you should not even be talking about working at the company; you should be focused on solving the problem. Fast forward three months, and you continue to produce quality ideas and introductions for the company, and it's taking up a big part of your nights and weekends. In that case, it's reasonable to ask the CEO if they could drop you a few bucks so you can make this a part-time gig, justifying putting more hours into the project.
But let's not get it twisted: you will send endless emails that get no response, you'll solve a problem for a company, but they won't have the cash to pay you until their next funding round. You will be doing this for five or ten companies at once, feeling like you are drowning in free work, and the reality is, you are, and that's the price of getting a job built for you rather than filling a random role.
I've spent nearly seven years messaging people cold and asking how I could help them, took part-time roles, and continued this cycle for my entire career. It has been challenging, and tomorrow will be challenging, too, but it's a hardship that I am choosing. I'm willing to go through years of hard times, because I want to work with the best founders and investors. Getting a shot to work with the best takes a lot out of me and will take a lot out of you if you choose to go down this path. It's not one I can recommend to everyone; this is simply the answer to the question, "How do I get to do what you do? How do I get a job at a startup?"
Taking my own advice to heart: I recently decided that I'd like to spend part of my summer helping the startup community in Cambridge (UK) and hanging out in England. So I cut my holiday in London short, took a train to Cambridge, slept above a pub, woke up, took down a few coffees, and asked strangers for directions until I knocked on the Dean of the Business School's door. I walked in, shook the man's hand, told him I'd like to contribute to his community this summer, and he pointed me to the leadership team for the entrepreneurship center. I'm on hour 4 of sitting in the lobby, waiting for a meeting, hiking backpack full of clothes next to me. I'll send more emails, maybe host a pitch contest in a local pub, and build a name for myself in the community, people respect hard, legitimate work; that's what I am going to provide. And you know what? it might not work out for me here in England, but I won't go home without having a few pints and letting the good people of Cambridge know that I can provide value to their startup ecosystem, if they choose to involve me in it, well that's a question out of my hands. All to say, if you don't get creative with your strategy, be direct, and show value, it's pretty hard for someone to go to bat for you when you do make your ask, whether it is to be a mentor in the startup community in Cambridge for the summer or strategy hire at a startup.