Your First Job : Startup or Established Company


You are a recent college graduate. Congratulations. Now what? If you’re like most Americans, you’re facing a huge college loan, payments beginning soon, and dates looming to vacate your cushy college room, say goodbye to your friends, and weigh moving back in with your parents vs. striking out to find a job. In other countries, you still have the same choices to make, i.e.

  • Move to a new city vs. stay in what you know?
  • Soul-crushing large company, or Energy-crushing new company?

To make things more interesting, you might even choose to strike out in a new city. A third one, away from your campus, your parents and to a new city entirely. What sort of company should you apply for? You have lots of choices, not a lot of time, and credit cards racking up, and the parental line of credit winding down.

Conventional wisdom

Job Safety. Job Security. A paycheck. Benefits. Retirement.

Conventional wisdom stated that you prioritized your job search immediately out of school along these lines. Your parents probably lived this way for you their whole lives, prioritizing steadiness and security, over flashiness and variety, our gratitude to them, so that you could *hopefully* live an uninterrupted and rich childhood and adolescence. There’s nothing wrong with this view, and you’ll find yourself returning to that view, at least once in your adult life. For your sake, and for your family’s – I guarantee it.

In today’s age, these values are personified in career choices ranging from established, large startup to large companies with several hundreds to thousands of employees and a worldwide presence.

The New, Venture Capital-inspired wisdom

Well, Peter Thiel obviously didn’t want you to goto college, as brilliantly depicted in Silicon Valley, season 1, but too late for you now. But VCs, do ask that you join a startup immediately. Here’s typically what they say.

  • You’re young – you have unlimited potential.
  • You’ll make a ton of money.
  • You’ll get priceless experience.

That’s great. Here’s what VCs really mean.

  • You’re young so you can work hard in the hope of getting a lot, but realistically getting little to nothing.
  • No, you won’t; we will if you work your ass off and we’re all lucky, and you may get something, but no guarantees. Oh, in the meantime, take less salary in exchange of this maybe-useful equity. We guide CEOs to hire employees who do this. This is a red flag for most interviews, asking for money over equity.
  • You’ll get *an* experience.

VCs and CEOs need an endless supply of talented, low-cost labor, who are reeled in by the promises of experience and riches, or is it rich experience?, extending a familiar dorm-like existence, both at work and at home, with snacks and co-living, but dig deeper and you’ll notice somethings.

Typically no 401k. Little to no career management. Few opportunities for growth, especially the earlier stage you join. Thinking quarter to quarter, poor planning etc.

The most frustrating thing will be working hard with a lot of first-timers, figuring stuff out, but often learning the wrong lessons. Here’s what you can do instead.

My Take

Your goal should be to find the perfect mix of paying off your debts, learning as much as you can and building experience, but also learning the *right* way to do things. Yes, there is a *right* way to learn about finances, capitalization, depreciations etc. Yes, there is a *right* way to learn pair programming, writing user stories and conducting user research. Yes, there is a way to take pride in your work and have a large impact. I see so many startups flounder in trying to think ahead, form a roadmap, run efficient engineering processes and part of the blame is in the gun-to-the-head reality of most early startups. You simply don’t have the time. Better to iterate quickly, make mistakes. But realize, the other reason is a shared lack of experience, as a lot of these startups are learning, as first-timers, from other startups who themselves have learnt from blogs and other resources and fixing themselves as they go. You have the rest of your career to learn from mistakes, choose to start instead on a solid foundation.

And, that is all doable by working for a large late-stage startup, one ready for an exit, or a public, maybe large, company. Yes, everything that’s old is new again. But not for the conventional reasons above.

In working for a public company’s technology group for example, you will have access to multiple training programs, learn what agile is or its many different incarnations in team product development, learn what an epic, story or task is, how to do estimations and pointing. As you progress through the company, you will learn about finances, about budgets, hiring, redundancies in teams and why that’s a good thing, and voluntary and involuntary attrition and retention numbers. You’ll have access to a diversity team and can get involved in efforts to change the face of your company, and learn why that’s important. Depending on your focus, perhaps even the ins and outs of working with a public board, mergers and acquisitions and the like. In short, you’ll get access to a variety of departments, areas of knowledge and more importantly, since the stakes are real, and therefore higher, you’ll build up a powerful arsenal of tools that you can deploy in the future.

Further, if your goal is to travel and maybe enjoy a secondment abroad, you’ll get to apply for a large startup’s overseas office, or a global location with an MNC. You’ll work hard, form great relationships, get to travel and learn on the company’s dime. You’ll learn the right vs. wrong way of doing things, because with the stakes as high, you’ll be quickly corrected if you aren’t sure of how to check in code, create a finance budget, deliver training, manage product teams, because there will be teams, programs and managers who can teach you just that. There’s something about the brutal reality of the public markets, or circling the event horizon prior to entry, that forces a strict leveling up, and you’ll benefit from those lessons.

And know what’s cooler? During this time, you’ll enjoy benefits like bonuses that you can stash away for a rainy day, or for your own entrepreneurial adventure, 401k with full match that is your future, the sooner you start compounding, and get to live in exciting cities. Then, develop other interests, hobbies, brands and figure out what you really really enjoy and don’t enjoy.

And then, after a few years, you might have a network, some savings, a retirement account. A group of friends who think about the same problems. Maybe even at the same company. Perhaps you’ve worked with smaller companies and startups and they take a liking to you. And then you can think about launching something of your own, or accepting an offer or soliciting one, to join a startup.

But, when you do so, you’ll be joining as a sensei, a master of project management, programming, business development or handling millions of dollars. Working across boundaries, peoples and teams. You might have to learn some cultural differences (they’re mostly overrated and most involve shorter-term thinking) but at least you’ll always know the right way to do things and could teach others a thing or two. Most importantly you may see or prevent noob operator mistakes, an amateur error or two and help right the ship.