How to Stand Out Like Derek Zoolander

Become the King of Confidence in Your Ecosystem

Sarah Hodges
Startup Grind
5 min readOct 21, 2016

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Derek Zoolander: King of Confidence

I cut my teeth on Boston’s startup scene in 2011. Tech was turning a new chapter, and the energy was off the charts. The action was moving to the city, as entrepreneurs and VCs traded in route 128 for Kendall Square. Katie Rae was at the helm at Techstars, leading a class of supercompanies like GrabCad, Help Scout and Promoboxx. BostInno was starting to take flight as a destination for startup news. It was the beginning of a new era.

It was also a whole lot easier to get noticed back then. As Mayor Walsh kicks off Women Entrepreneurs Boston (WE BOS), a week-long initiative to help advance women entrepreneurs, I can’t help but think how fortunate I was to come onto the scene when the scene was so much smaller.

Over the past few years, our startup ecosystem has erupted with activity. According the Boston Redevelopment Authority, high tech employment in Boston has grown from 4.6 percent to 6 percent, as a proportion of total employment, from 2010 to 2014. That’s good news for Boston, but challenging news for entrepreneurs hoping to float to the top in the swelling sea of the new tech landscape. When it comes to the innovation economy, it’s harder than ever to cut through the noise.

So what’s the playbook for standing out today in tech?

Build Something That Matters

Creating something that matters is table stakes for getting your name on the map. Forget news for the sake of news; focus on being recognized for your impact. Consider why your idea is game-changing, then relentlessly build toward your vision. When I launched Intelligent.ly with Dave Balter back in 2012, we created our company purely with the intent of connecting people in the startup community to learn from each other. The outpouring of support was unbelievable and the word of mouth awareness spread like wildfire. Getting noticed starts with building something of value. Do something remarkable, make a meaningful contribution to the world, the rest will follow.

Sing Your Own Praise

We all devour the BostInno Beat when it hits our inbox everyday. We can’t deny the influence of digital media on shaping our perceptions of the rising leaders in our community. But sometimes the most exciting people and companies aren’t the ones on the tips of our tongues.

Remember the old adage about a tree falling in the woods? If you build something incredible, but keep quiet about it, you won’t make it on anyone’s radar. While there are a few exceptions to the rule, most of the people you hear about often make a concerted effort to shape their brands.

Confidence is key when you’re preparing to push yourself into the spotlight. HubSpot VP of Culture & Experience, Katie Burke, recently wrote a standout Medium post recently in which she refers to the “best supporting actress syndrome” many women experience in the workplace. Rather than pursuing leading roles (like CEO), they settle for supporting roles — roles that feel more ‘attainable’. Countless studies have shown just how devastating this confidence gap between men and women can be to our careers. Creating awareness about why your business is noteworthy starts with believing you are.

With the self-assuredness of Derek Zoolander, you’ll be ready to walk the fine line between egotism and healthy self-promotion. Don’t humblebrag — we can see right through you. Do find creative ways to highlight your achievements. I’m a big fan of bolstering other people you respect and admire while sharing your own wins. Celebrating a new product launch? Consider whether there are other entrepreneurs you can weave into your announcement to create a more engaging story. Everyone wins.

Stack Your Corner with Supporters

Every entrepreneur should have a network of sponsors who can champion your cause — an invaluable group in helping you make a name for yourself. I’m a Partner at Pillar, a new early-stage venture capital fund in Boston, and we’ve seen just how critical it is for entrepreneurs to have a community of supporters rallying for their success.

To help meet this need, we partnered with a group of world-class CEOs and executives as co-founders in Pillar, people like Jason Robins (@DraftKings), Jeremy Hitchcock (Dyn), Ellen Rubin (ClearSky), Corey Thomas (Rapid7). All are actively involved in making introductions to prospective customers and providing guidance to our entrepreneurs.

We’re not alone in connecting entrepreneurs with vocal supporters.

Last year, Sarah A. Downey and Diane Hessan partnered with Accomplice to found Rev Boston. The program digs deep to identify high-potential leaders who might not otherwise be on our collective consciousness, connecting the group with with a network of industry and venture capital leaders. Sarah has done an incredible job advocating for the next generation of women leaders in Boston; she’s not just talking about raising awareness — she’s getting it done. If you know anyone who should be in Rev 3, now’s your chance to nominate her here.

Consider the people who naturally advocate for you already. Get in the habit of regularly reaching out to inform your sponsors about your recent accomplishments — and don’t forget to share your gratitude for their support.

While it’s not as easy as it was a few years ago to build your brand in Boston tech, there’s still a solid recipe for success — build something that matters, don’t be afraid to promote yourself, and have a little help from your friends.

Sadly, we can’t high five on Medium. Just add your ❤ below.

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