So you want to join a startup

I’ve seen some posts out on the ‘net about working with startups, and I thought I would use my 9 years of startup experience, combined with my 3 years of big-company experience, to provide my readers with some insight on how to prepare to work for a startup, and what to expect at a startup. Note that I am not going to justify why you want to work at a startup, or debate the relative merits of startups and larger companies. Those topics are well covered. I’m just talking today about what you should know and expect.

How to prepare:

1. Save 1 to 3 months worth of expenses, more would be better

    Startups often have rocky pay cycles. On occasion, you may be asked to go without pay, or go on half-pay for a time, in order to make ends meet. If you can’t afford to go 1 – 3 months without income, don’t work for a startup. Also, that’s just a bad thing in general.

2. Be prepared for the Joy/Gloom curve

    In the ocean of world capitalism, big and medium companies are the ocean liners, virtually impervious to storms. Startups are life rafts, tossed about wildly on the seas of high finance. You will hear great news one day, and depressing, frustrating news the next. “We got the deal with BigCo! YES!”, and the next day: “We’re getting sued by CompetitorCo, CRAP!”
    I will admit that this is highly stressful, but it is part of what makes startups interesting, challenging and rewarding.

3. Match your skills to what the startups need

    Startups need generalists – people who can do just about any job. Your expertise at operating the T5404-b collating copy machine is not a skill that a startup’s management will find useful. Expand yourself, and make sure that you are strong in the general capabilities of your role.

4. Let go of deep, complicated business case analysis

    Startups rarely (if ever) have time for deep business case analysis of decisions. If you enjoy making large-scale multi-year forecasts to justify every decision you make, then you’ll probably be very frustrated when the CEO says ‘to heck with that, we’re doing X’ after about 15 minutes of discussion.

What to expect

5. Be prepared to do just about anything.

    In my time at the various startups I’ve worked at, I’ve loaded and unloaded trucks (as a product manager), emptried trash (as a CTO), bought coffee and whiteboard markers (as a chief architect). I’ve chased down thieving employees, fixed servers by candelight, slept on the floor in my office, hand-built whiteboard stands, and personally couriered rackmount Linux servers from Atlanta to Washington DC, carrying an awkward 40+ pound box through the airport. And I’ve gotten off easy! I know of other people who have taken turns fixing the leaky roof of their building, sprayed for bugs and a lot of other unpleasant things completely unrelated to their job function.

    But I did them because they needed to be done, time was of the essence, and conserving cash is very important.

6. Expense checks will take a long time to arrive

    You’ll probably have to use your personal credit cards to help keep the company moving. It is safe to assume that the company will lag in paying you back.

7. Don’t count on, or expect good health insurance or 401k matching

    For a long time, 401ks were expensive to setup, and startups wouldn’t even offer them. Now, they’re not nearly as expensive, but you certainly can’t expect matching funds out of a company that has little to no revenue. Health insurance is similarly meager. If you’re used to great coverage that guarantees all sorts of perks, you will be disappointed in the choices you are given at a startup. And sometimes those choices are “We don’t offer a healthplan.” In which case, you’ll just have to go out and find some yourself.

8. Expect to go to many fewer conferences and/or training seminars

    You’ll learn a tremendous amount from your day-to-day job, so for the employees of startups, training seminars are often superflous. Conferences would be nice, to keep up with new events and meet new people, but unless those meetings lead to new sales, they are probably a bad idea.

9. Expect to have more to do than you can handle, and expect little recourse from your boss

    I deal with this pretty much every day. Too few people working on too many “must do” projects, all of which needed to be wrapped up 3 months ago. This is one of the most frustrating aspects of startups for me, because I know that there’s no magic “money spigot” in my bosses office that lets him hire three more employees to take up the work. But the work still needs to be done. In theory, multitasking is less efficient than single-minded focus. In practice, if you can’t work on project A until you get a phone call, then you work on project B. And once you get the phone call, you are obliged to switch back to project A, because it is in worse shape.

10. Expect a lot less formality

    If you enjoy a highly professional environment where everyone treats each other with maturity, politeness and grace, then you will probably not enjoy startups. Soda-can baseball, flipflops, practical jokes, pingpong tournaments, conga lines – all part of the startup experience.

11. Every day is a chance for you to show (and win) leadership

    More than anything else, startups need projects to have ownership – people who are committed to seeing the project finished and working. If you are willing and able to do that, you are valuable, regardless of your experience level or your title. No one cares about titles. In startups, we care about results. Note that ownership is very valuable, but seeing the project through to success is priceless. Don’t take on projects that can’t succeed.

12. Passion is more important than experience

    Related to the previous point – startups are about passion. They are about caring about success, about recognizing that you are making a difference in the day-to-day lives of all of your comrades. Passion helps you weather the storms, it helps you to find the energy to do what must be done. It helps you accept the bad with the good, helps you step up and take command – because you care about this company and you want to make it succeed.

This is my list. I’m sure I haven’t thought of everything. If you have suggestions on things to add or things to clarify, I welcome your input.

Thanks!

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