Recent years have shown us that no company is recession-proof…not even the biggest or most established ones. In 2015 I was headhunted from my job at a large group of hosting companies to do marketing for an API startup. A few months ago I was headhunted from that to do marketing for another (web hosting) startup. Between these jobs and having interviews with other startups in the past, they’re normal to me so I’m still surprised that people tend to view them as risky.

In 2008, fresh out of uni, I got a job working for a catalogue company. Three days after I started, they started making redundancies. I was lucky enough to keep my job, but others didn’t. Rather than being a startup, it was an established medium size company in a pretty old-fashioned industry with high overheads and a customer base that largely didn’t use the internet at all.¹ You’d think that seeing redundancies and the redundancy process in my first ever full-time, permanent job would make me more risk-averse, but they didn’t. What the experience highlighted for me was the importance of doing something interesting, that I believed in, where I could use my skills and develop them further.

Since then I’ve made several jumps in and around the tech industry. I’ve had five jobs in eight years, plus several interviews for all kinds of places, which a lot of people would probably say is a warning sign (one of my favourite mottos is ‘Never settle’). I’ve grown my salary. I’ve made companies five figures a month. Everyone’s a winner.

Having said that, I much prefer working for small companies. I enjoy my work, and because of that I like to get on with it. I’m not a fan of corporate bullshit, so if you ask me what super power I’d have, I’ll probably answer “China”.² I hate wasting time, so startups are ideal. It’s important to me to make a visible difference, and it’s important to me to feel like I’ve achieved something significant. Startups tick those boxes for me. But by their very nature they’re a different story every time. So how do you minimise risk by picking a good one to work for?

What to look for in a founder

The short version:

• Complete, relentless, unyielding belief in their concept.
• Incredibly deep understanding of their industry and target audience.
• Commitment that matches their passion.

The long version:

You can generally get a good idea of what the founder is like and how committed they are just by talking to them in person. I went for an informal chat with a guy creating a startup that sounded pretty interesting on paper. After meeting up with him, it turned he had a full-time ‘traditional’ business, didn’t have much experience in the tech world, and had hired a developer to make an app for him. Immediately this was a huge red flag to me: someone else’s side project isn’t my career. From this I knew straightaway that I didn’t want to pursue it further. Plenty of people are jumping on the app bandwagon, but the success stories are always from people who have a good track record in their field, are dedicated, are backed by an excellent team, and have great contacts. The founder’s passion has to be coupled with commitment.

A good founder has a good balance of natural intelligence and a practical business mind. If there are multiple founders and they successfully cover these traits between them and work well together, that’s fine. If it’s a single founder or disagreements seem rife, alarm bells should be sounding.

Ask the founder(s) what their ultimate goal is for their startup. Expect success and money to be in there, but you can tell a lot from the other things. Industry fame? Providing the world with something new and needed? To fund something else? To provide the best life for their family? The experiences along the way?

It’s worth mentioning that a good founder will doubt himself or herself at times. Can they really do this (again)? Will they really disrupt the industry? What if they don’t meet their own expectations? This is all perfectly normal, because you’re working with people who relentlessly demand the best for themselves, their companies, and their achievements. This is why you’re working for them. The worst thing in the world is working for people who don’t give a shit.

The whole funding thing

The short version:

• Where is the money coming from?
• Do they have a clear vision and plan for how money will be spent?
• Do they have specific goals and timeframes?
• Do they seem on the ball with money generally?

The long version:

Lots of people have been taught that it’s rude to bring up the topic of money…especially someone else’s. For startups, this rule goes straight out of the window. It’s perfectly okay to ask how the business is being funded; in fact, many founders are keen to talk about it and will bring it up before you do. They should be able to discuss their funding plans and successfully communicate to you that they’re clear on rough estimates of costs (how much they need for running the business, how many customers they need to make a profit, etc.)

If they’re bankrolling it themselves, great, but for me personally, they have to have had huge proven success already. Both startups I work/have worked for have sold their last businesses for millions and re-invested a large chunk of that money wisely. One of the startups has external investors on top of that, but I joined them before they secured funding. Was that risky? Maybe. What convinced me was that the founder already had strong, proven investor interest, plus a clear plan for where investment was headed and how much they wanted to raise (we ended up exceeding that target). If the startup you’re considering already has funding, what stage are they at? How much have they raised so far? When are they planning their next round of funding? How long can they survive without another round/making profit?

The product

For me this comes down to two things:

• How interested am I personally in the product?
• How well do I think I can sell it?

Your questions for this will depend on your job role and how much you care about products generally. As a marketer, I set myself the requirement of believing in the product. If I have my doubts about it or I don’t care about it, I’m not going to do the best job I can, so there’s no point in pursuing it. Two further questions come into play at this stage: 1) Do I think people will want/need this product? 2) Do I think that this startup offers a viable and realistic solution to a genuine problem?³

The perks

The tech industry, and startups in particular, are renowned for their perks. Over the course of my career I’ve been to theme parks, had literally hundreds of meals out and takeaways in, been bowling, been drinking more times than I can count, been to parties and awards ceremonies, travelled first class across the UK, had lots of shiny Apple stuff to use, had a wealth of games consoles and table tennis tables and Internet of Things enabled rooms at my disposal…and much more.

What have I valued most over the course of this time? Pay increases and bonuses, my tickets and travel to tech events paid for, and the opportunity to speak at Google. None of those were ever listed as perks in the job descriptions. Probably the only benefit that’s been a genuine deal breaker for me is no dress code, which is pretty much a standard in the industry now.

Simply put: If they can’t hire staff without the perks, they’re not a good company to work for. You’re not going to leave a company because another one lures you in with a better table tennis table. If your question isn’t, ‘What kind of salary, share options, and holiday leave are we talking?’, but ‘What Playstation games do you guys have?’, you should be applying for a job at Game instead.

The more perks a company has, the more it’s trying to a) keep you in the office b) use it as a reason to avoid giving you a decent pay rise and/or c) maximise its tax relief. The work-life balance line is already blurred thanks to the internet, and while I’m always in favour of meals and drinks out, it’s really fucking annoying to here the tap…tap… of ping pong balls when you’re trying to meet a deadline.

The rest of the team

Hiring the best people is the most important thing. If they’re looking to hire the cheapest people rather than the best people, is it really a startup you want to work for? I want people around me who are stimulating and who I can learn from (even if I’m learning things that are nothing to do with my job!). Every single member of the team is incredibly important in a startup, and everyone makes a lot of difference. There’s no slacking off and you’ll end up pitching in wherever you’re needed, but the upside is that you pick up new skills, strengthen your employability, and feel appreciated.

If there’s an existing team, find out as much about them as possible and meet them (or at least speak to them) beforehand where possible. Find out what the plan is regarding future hires – will there be any? Where will they be based? What kind of job will they do? And just like any other potential job, decide if you like what you’ve seen so far.

The future

This is the tricky bit; no one has a crystal ball. However, any glimpse you can get of the long-term vision helps. How does the founder (and the team) see the future? What are the short-, medium-, and long-term goals? When will they sell, and who are they likely to sell to? If you do want a job for 20+ years, or even 10+ years, then a startup probably isn’t for you. There are curves of growth and achievement, but you know at some point it will be sold on, and the new buyers may or may not want to keep the existing staff. This is true for many tech companies, whether they’re typical startups or not. This is why it’s so important you trust the founders. There are founders who will give you a year’s notice and a nice payout and even help you find a new job, and there are founders who will pull the rug out from under your feet with no notice or help whatsoever; if you’re lucky they’ll wave to you from the Caribbean.

Other people, particularly those who are used to corporate life or have been through collapses before, err on the side of caution. Some people want job security and somewhere they can stay for 20+ years, and I completely understand that. That’s totally opposite to my way of thinking, because I like new challenges, but I get that it’s not for everyone. I like to leave companies after giving them a solid foundation and a clear vision of where their marketing is headed, with all the tools and strategies they need to carry on without me. I also live in a smallish city that has far more than its fair share of tech companies and tech startups, and I happen to be more web savvy than a lot of marketers, purely because I’ve been involved in the industry since I was a teenager. There are plenty of job opportunities out there in the tech and startup worlds, and it’s far better to be in a growing industry than a dying one. Skills are always transferable to another company in the tech startup world, and everyone is desperate to hire tech-minded people.

There are some huge advantages. Everyone is really supportive of a startup and people want to help you out where they can. You’re there at the start to grow something special from scratch. You’re working with people who are extremely intelligent and passionate and not burned out from doing the same paperwork in an endless hierarchy of middle management who are also burned out.

To me, it’s a bigger risk to work for a small/medium sized company that isn’t growing and has only marginal growth for the past few years, or a company that heavily relies on another company for its success, or a company in a dying industry, or a company with large overheads. The recent recession and years of economic turbulence has shown that only smart businesses are safe, so is it really that risky to leave an established company for a startup? In my opinion, it’s not. If the company looks good and the people look good, just go for it.