Today's economy

Four questions before you join that start-up

By Kevin Press,

Comments (4)

I had a coffee yesterday with a friend who is looking for a marketing role. Like a lot of professionals out of work these days, she’s finding it hard to get her foot in the right door. We talked mostly about the benefit of not focusing too sharply on just one or two specific industries.

Image of a ribbon-cutting at a business grand opening.She asked me if I thought joining a start-up would be a good idea. As it happens, I did it myself about 20 years ago. Here’s the quick version of the story I shared with her.

I landed my first real job in 1989 as the editor of a trade magazine serving the Canadian landscaping industry. As someone who grew up allergic to grass (and, by extension, cutting the grass), it’s fair to say I was not a subject matter expert.

What I liked about the work, though, was the young publisher who hired me. He was a good guy who taught me a lot about how to put out a magazine every month. When he left to launch his own publication for professionals in the Canadian sign industry, I didn’t have to think too hard about joining him. The deal was simple. I’d be his editor for a few months (working at night and on the weekends while I kept my day job) in exchange for a percentage interest in the new magazine. When he could afford to pay me a salary, I’d join him full-time.

That happened, eventually. But so did a crushing recession that saw annual gross domestic product growth in Canada plummet from 5% in 1988 to almost zero growth in 1990. A year later, the economy shrank 2.1%. Things never got so bad that we had to close the business; we eked out an existence publishing out of a Richmond Hill, Ont. home office.

In retrospect, I wish it had crashed and burned more quickly. Half a dozen years later, we were no further ahead, financially or otherwise. It took me almost that many years again to get my career back on track.

But of course joining a start-up doesn’t guarantee poverty any more than it promises riches. If you’re lucky enough to work with the right people, with the right work ethic and a good idea, it can be a career-making move.

Yesterday, I spoke with Ari Aronson about how to evaluate a start-up job opportunity. He’s founder and executive recruiter at Ari Agency, a boutique recruitment firm that places professionals in digital marketing and media roles across the country.

There are four questions you need to ask:

  1. How’s the funding? Start-ups typically offer poor salaries. You’ll probably be looking at a low number that comes with the promise of equity in the company or significantly more money down the road. The question is whether or not the company can make it far enough to reward you for your patience. A lot don’t, not because the people don’t work hard or because their idea is weak. They just run out of capital.
  2. Is your role clearly defined? “Start-ups aren’t always well organized,” said Aronson. “Are the roles and responsibilities clearly outlined?” There’s nothing wrong with a job description that includes an “all other duties as required” line. But a company that lacks a clear delineation of duties is almost certainly poorly run. Don’t go there.
  3. What kind of hours will you need to work? If you’re put off by long days, then a start-up probably isn’t for you. But even for those really committed to a job, things can get out of hand in a small operation. “There might be some expectation around the culture and how they work,” Aronson told me. Some management teams demand employees not only work as much as they do, but that they work in the same way they do. In other words, if all-nighters are the norm, you may be expected to follow suit. “You’ve got to know what you’re stepping into,” said Aronson.
  4. Does the leadership have a track record of success? No matter how impressive the team is and how good their idea is, look for people who’ve launched successful businesses before. Look for pros who know how to write a business plan and manage a profit and loss statement.

These aren’t questions that come with clear right or wrong answers. It’s about your comfort level with the situation you’re considering. What’s most important is that you’re clear about the opportunity. If you’re short on details, tread carefully.

More career tips:

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Lucas on

I have joined 3 start ups in the past. To anyone who is thinking about joining a start up, please remember that the most valuable thing in your life is time. Please walk away at any time you are not absolutely convinced that the company will hit it out of the park. Otherwise, you will lose your time and you will be out looking to start all over again from scratch.

Best of Blogs – Plutus Awards on

[…] If you’re contemplating joining a start-up, this article by Brighter Life is a must read since it covers the Four Questions Before You Join That Start-Up. […]

Best of Blogs - Plutus Awards on

[…] If you’re contemplating joining a start-up, this article by Brighter Life is a must read since it covers the Four Questions Before You Join That Start-Up. […]

Paul Gagliardi on

Those are 4 very great questions to ask. Another question that comes to mind is if the company has the team or individuals in place with the necessary skills.

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