Should I go work at a start up?

That was the question posed to me by a former colleague who has been working at a big company for donkey’s years – in the tech world, that’s about 5. And who has a lot of experience and some great educational credentials. And, like most important decisions in life, the answer was, it depends. I thought it might be useful for others so I thought I would jot don my thoughts and advice. Basically, there are overall points and then specific points about a start-up that you should consider.

Start-ups In general

Are you okay with failure? Most start-ups fail and yours is likely to be one of the failures. I particularly liked Marc Cenedella’s post on failure at entrepreneurial ventures. Most of the time you’re failing and you’ve got to push your way through it. Having failure on a CV can still be restrictive – especially more so here in the UK. If you can deal with that, it’s a start.

Are you a hustler? Working at a start up is a slog. It can be hard, filled with disappointments and at times it can really get you down. It’s not only founders that have to be relentlessly resourceful (hat tip to Paul Graham and this post on Y-Combinator talking about characteristics of YC founders), it’s everyone in the first 100 who have to hustle to get shit done.

Do you value short-term cash? More over one day at Yahoo! than I have in a year as a founder. But I’ve learnt a lot more so far. I’m an extreme case. Most start-ups pay in promise and a lot of the promise doesn’t pay out (see question one). If you need a higher salary think twice about joining a start up.

Are you patient? If you’re joining a start-up you need to make a commitment. To get the real value out of any equity you’re looking at 3, 5 or 7 years from the start. To get real experience you need to see through a couple of pivots, strategic shifts, partnerships and growth in customers. If you’re not willing to see it out why join?


Do you believe in the team? If you’re joining a start-up you should think (at least a bit) about the opportunity like an investor. Chris Dixon has a great post on this when he talks about the Dropbox opportunity that he missed by looking at the competition in the market rather than the team. If you’re not sold on the team running the ship then you’re going to have trouble trusting decisions.
Do you like the space or the technology being used? Something has to keep you hooked to the company. If you’re not thinking about the product, the market, or the technology being used in the company you’re going to get bored and not be able to really make a difference.

How well are they funded? Are they likely to raise money? Joining a 2 person company as employee number 3 with a couple of million in the bank is a great ratio. Joining a 10-person company with only 100K in the bank is a tough sell. Even if you don’t know the exact amounts there are some great resources to be able to check the status of the team/company. Looking up the investors, looking up the team on Linkedin and seeing what they’ve invested in or what they’ve done in the past can be a decent indicator for future success or at least their ability to stick around.

I’m sure there’s lot’s more that I’ve forgotten but I hope this is a useful starting point for people considering working for a start-up, I’m sure there will be other points in the comments.

  • laura

    thank you Farhan, great advice and food for thought…