What do Jony Ive, Boyd Multerer and Tony Fadell have in common?

Nowadays Jony Ive is a superlative designer and one of the main executives running the show at Apple. His design acumen and personal relationship with Steve Jobs propelled him through the ranks and his personal brand is closely tied to such big product names as the iPhone, iPad and iWatch.

Gaming fans recognize Boyd Multerer’s vast contributions to Xbox Live and Xbox One at Microsoft. He recently left his long time employer recently, and is now doing independent secret stuff.

Tony Fadell of course, is the Nest CEO, who recently sold his smart thermostat company to Google for a staggering $3.2B.

A foot in the door

So what do they have in common? Technical and design talent, obviously. Energy and determination, no doubt. But what else?

It so happens that at one point in their careers all three of them worked as contractors. Ive started as a consultant at Apple through his design agency, Tangerine. Multerer put a foot in the door at Microsoft by working on a contract basis for three years before eventually joining the company and Fadell designed the iPod as a contractor at Apple prior to starting Nest.

A new meaning

Interestingly, while Apple and Microsoft hire contractors often, many startups are more reluctant to do so. The reason is that startups want to build a team that will stick together through the highs and lows and invest in their own culture. They feel that freelancers are too mercenary to take up key roles, especially early on in the company's life.

This reputation has been bolstered in recent years by the rise of freelancer marketplaces like oDesk/Elance. A company can hope to find a freelancer there, typically for a short term gig – maybe write some code remotely, design a logo or do some admin, with hourly rates driven down by international competition.

These sites have created a great opportunity for companies to get work done cheaply and created new job opportunities for professionals around the world. In the meantime though, the meaning of the word freelancer in people's minds has been altered. Many now equate freelancers to the masses of cheap online labor rather than to genuine craftsmen like Ive, Multerer and Fadell.

It's easy to dismiss freelancers as seeking only short term cash in exchange for their services, but the reality is more nuanced.

Startups and contractors

Startups offer freelancers a wealth of opportunities to try their hand at new technologies and industries while earning a living without committing over the long term like startup employees, whose salaries are typically low and who only accumulate a significant upside as their shares or options vest over time.

With the steep decline in the cost of starting a internet company, the number of startups has skyrocketed of late. But the rate of startup success has not increased accordingly. Most startups fail - which is one of the reasons why so many freelancers, while enthusiastic about working at startups, are reluctant to take the plunge as full time employees.

What would go through your mind if an early-stage startup founder approached you, pitching his idea and hoping you'll join his crusade? You might be swayed if they're persuasive and you believe in the project. If you're not that sure and you know how most startups fare, you might be reluctant to accept a huge paycut for the foreseeable future in exchange for the pursuit of what may very well be a pipe dream. On the other hand, working with passionate people in an environment where everything is possible certainly beats your day job working a BigCo. So what should you do?

A middle ground

Freelancing offers an interesting middle ground - you still get paid decently and you don't commit to the long haul. If after a while you decide that the startup is going somewhere and that like working there, you're more likely to join them permanently. Meanwhile you can keep your eyes open for other opportunities.

In our experience, just as Jony Ive, Boyd Multerer and Tony Fadell switched from contract positions to permanent engagements, we don't believe that there is a magical border between freelancers and employees. It's simply human nature to wait for the right opportunity before committing to anything long term, and today's work market enables qualified pros to make a living freelancing, sometimes enjoying a lifestyle that would have been inconceivable only a few years ago.

At Sevendays we initially focused all of our efforts on freelancers. Our clients - almost only startups - kept asking if we could also propose people for full-time, permanent positions. We initially assumed that our job seekers were only interested in freelance work, but we were wrong.

We asked them if they would be interested in taking up full-time positions, and to our surprise more than 50% said they would, given the right opportunity. Since then we've accepted requests for both permanent and freelance opportunities, with equal success.

Better than an interview

Of course starting with a freelance contract can also be beneficial to the startup. Why commit to hiring an employee when you can test their skills and culture fit for a while before deciding that it's a match made in heaven.

Finding the right employees is a challenge for any startup. Screening and interviewing candidates has its limits - how will you know whether the candidate actually gets things done and gets along with the rest of team? Some startups have adapted well.

Buffer has gone public about their 45-day bootcamp during which they hire the candidate on a freelance basis. At the end of this period, both sides are able to decide whether to continue, and if things don't work out then the contract simply expires. It works as a double opt-in mechanism, favorable to both sides.

Time will tell whether other startups will follow suit.

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