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The Perks of Being an Outlier CEO Instead of looking at the challenges of being an outsider, examine all of the advantages.

By Caren Maio Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.


In school, the unpopular kids sit alone at lunch. Some of them just don't fit in. In business, it's much the same way. Fitting in is just as important. It's the fast track to networking, perks and promotions. But what if you're not part of the club?

I'm a female CEO of a New York real estate technology startup -- an outsider to my industry in more ways than one. New York is 2,563 miles from Silicon Valley, the epicenter of new tech ventures. Real estate and technology companies are predominantly captained by men. Investors and customers alike can be sternly skeptical when a younger woman from the advertising world comes to transform how they do business in their fields.

Being an outsider comes with plenty of challenges. But this article isn't about that. I'm here to say, without reservation, that these same differences can be an advantage -- and have been for me. As an outsider, you're freer to innovate and can see solutions others miss. Being different means you stand out from the competition, which can be an asset. And it's far from a lonely struggle. Underdogs often build close-knit networks to help each other find their way. It hasn't been an easy path, but here's how being an outlier has given me an unexpected edge.

Related: Warning! Your New CEO Might Be a Square Peg in a Round Hole.

You see what insiders miss.

When I launched my company, Nestio, in 2011, I wasn't a real estate insider. I was a frustrated renter, tired of showing up at listings in Manhattan only to find the units had been already leased. It was clear to me that the system was broken. After doing some research, it became obvious that outdated technology was the root of the issue. In an era of cloud-based apps, landlords were still using spreadsheets and whiteboards to track inventory.

Now, this wasn't a new problem in any sense. Apartment hunting in New York has always been a headache. But people inside the industry had gotten so used to it that they couldn't see any alternatives. We sensed an opening for technology to wipe away the clutter because we hadn't become trapped in it.

We've seen the same scenario in many industries. Disruptive innovation sometimes comes from people with little connection to the sector. They can translate it into some of the strongest business ideas. AirBnB founders Brian Chesky and Joe Gebbia were trained as industrial designers before upending the global hotel industry. Apple made computers and MP3 players before its revolutionary iPhone tossed mobile phone giants Nokia and Blackberry to the wayside. Established leaders can get stuck recycling or making small improvements to their older ideas, missing out on newer ideas outsiders create.

You stand out from the crowd.

When you're an outsider, you will stand out. You're unique. You're memorable. Own it. People will look at you differently, for better or worse. You can turn this to your advantage, although you may have to work at it.

Tesla CEO Elon Musk stands out in the automotive world as a former software entrepreneur with no ties to Detroit. But he embraced this difference. Where big car companies hedged their bets on green technology (Chevy's mid-market Volt ran on electricity, but kept a gas engine to charge the batteries), Tesla pursued an uncompromisingly different vision -- an all-electric performance car. Had Musk tried to blend into the pack and taken fewer technological risks, there likely wouldn't be a years-long waiting list for Tesla's new Model 3 right now.

Related: Why These 5 Franchises Stand Out From the Crowd

For me, being an outsider made it tough going when I started Nestio. Early investors were concerned with committing to someone too far from Silicon Valley to engage with closely, especially since I didn't have a proven track record. But I embraced and emphasized what made me different, and eventually investors came around. They saw they needed to diversify away from the familiar and their home turf, and the biggest investors in my last two funding rounds came from the West Coast.

You connect more deeply.

People form their own connections with others of similar values. It may take some effort for outsiders to develop a network, but the bonds can be deeper and more rewarding than being in the in-crowd, in my experience.

Female entrepreneurs in particular face unique challenges. Fewer than 18 percent of U.S. venture-funded companies had at least one female founder in 2014. And companies run by female CEOs receive just three percent of total venture capital investment. These disparities are magnified in tech, where women account for just 26 percent of the total workforce and only an estimated eight percent of developers.

But despite (and perhaps even because of) these hurdles, powerful networks -- both formal and informal -- have evolved. Sheryl Sandberg's Lean In movement has given rise to dedicated circles of women in tech seeking peer support. Groups like Girls Who Code offer free camps to close the gender gap. And organizations such as Astia and Springboard Enterprises help female-run companies access capital, partnerships and mentorship.

Related: Women Entrepreneurs Underestimate Themselves: What We Can Do About It

Personally, I've found great support in informal connections. Through shared speaking engagements, shared investors and networking events, I've met other female entrepreneurs who got their start around the same time I did. We connect for breakfast or drinks to talk honestly about issues many business people wouldn't whisper about -- benchmarks for compensation, what mistakes we've made and what struggles we've overcome. Business can often be a cut-throat affair, but we share knowledge and connections because we appreciate the mutual challenges faced and want to see each other win.

You rarely get to choose whether you're an outsider or not. Sometimes age, gender or ethnicity makes that decision for you. Other times, being an outsider is necessary to creating the change you want to make in the world. Don't fear this position, or be ashamed of it. Outsiders have an uncanny habit of seeing and achieving things that insiders overlook.

Caren Maio

Founder and CEO of Nestio

Caren Maio is founder and CEO of Nestio, a residential leasing and marketing platform. Follow her @CarenMaio

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