What to Look For When Considering Working for a Startup

Over the last couple of years, I’ve consulted with a lot of companies. Fortune 500s, global brands, mid-size companies, and a whole lot of early stage startups. Seed round, Series A, Series B. You get the picture. I’ve seen the entire range. Not to brag, but to say this: I’ve had a front-row seat to how different businesses operate, and I’ve learned a lot about what really matters if you’re thinking about working at a startup.

Startups are exciting. There’s no denying that. You get to help define the company. You make decisions fast. You see your work reflected out in the market way quicker than you ever would at a later stage business. But they also come with risk. Resources are limited. The runway isn’t always long. Markets shift. Some of these companies will be around in ten years. A lot won’t.

So if you’re considering making the jump, here are the things I’ve learned to look at:

1. Look at the founders.
This is the biggest one. Who’s leading this thing? What’s their background? What kinds of companies have they built before? Have they had exits? Have they failed? Do they have experience that makes sense for what they’re trying to do now? If someone’s only ever worked in tech and suddenly they’re launching an apparel company, you have to pause.

Go watch their interviews. Read what they’ve written. Study their track record. At an early-stage company, the founder is the company.

This is a little random and I know it might be controversial but whenever I look to invest in an early stage company, I go look at the founder’s Instagram. If most of the posts are of them traveling on vacation, it’s a red flag.

2. Look at the investors.
It’s not just about whether they’ve raised money. It’s about where the money came from. Is it from reputable firms that have backed other successful companies? Is it friends and family money? Is it a group of angels with different agendas? Follow the money, as they say. Because most startups will need to raise again, and the quality of the investors determines whether they’ll be able to. If you can, even ask to talk to someone on the board. Ask them about their vision for the company and see how it aligns with those of the CEO