Cindy McLaughlin
Co-Founder/ Chairman & CEO
Style for Hire
Who inspires you?
My amazing team! They pull off an impossible amount of work with competence, good humor and kindness.
Why are you an entrepreneur?
I’m not sure what else I could be. I love working for myself, and get frustrated in environments that aren’t entrepreneurial. Strangely, I feel more confident as a CEO than in any other job I’ve ever had.
Where do you see your company in the next five years?
We’re working hard to capture and grow the personal styling market. If we can be a hub for the lion’s share of styling advice (and transactions), I’ll be a happy lady.
How is your company different from your competitors?
We have a unique blend of celebrity horsepower, scale (we have 150 stylists, and counting), a national presence, and the unique ability to build broad national relationships with partners who provide value to us, to our stylists, and to our clients.
What was a defining moment in your career?
Wow. That’s a hard question. There have been so many moments where my career could have flourished or fallen apart. I think our first major round of fundraising was a really big deal for me. It was external validation well beyond the nice things people would say about us. I’ve always known we have something special in this company, but to have a large group of very smart and accomplished people (Thanks Golden Seeds + NY Angels!) put their money, support and connections behind us, felt great.
What is your next step with your company, your career?
I take life one day at a time these days. My singular focus is to make Style for Hire a success, which means that it’s a self-sustaining and self-reinforcing entity that’s maximized its potential on the open market. After that, I’ll want to take a bit of a breather (start-up life is intense in all the ways we know), be with my family, and consider my next company.
How did you finance your business when it was at the early stage? (Self-funded, crowd-funded, Angel Investor, VC)
A mixture of self, friends + family, and angel investors. I love those people.
Tell me something about yourself that we don’t know already.
I’m an incorrigible night owl. I love the hours between 12-2am. They let me be quiet and get stuff done, or watch Hulu like a zombie if I need to zone out. I’ve never been otherwise. It’s probably not healthy, but sleep is just too boring.
What is your guilty pleasure? (Real Housewives, Chocolate, 50 shades of Grey, etc)
I’m hooked on WordHero for Android. It’s like Boggle, but with online competition from people around the world.
If you had one year that you could say was the best year of your life what year would it be? Why? How old were you?
Probably my junior/senior year abroad. I was 19, lived a semester in Madrid, the summer on L’Ile de Re (an island off the coast of La Rochelle, France), and another semester in Strasbourg. Everything was an adventure, everything was larger-than-life, and I’ve never laughed as much in my life.
Describe a time you failed. What did you learn from that experience?
There have been many. I had a pretty devastating experience working for a large department store conglomerate. I was summarily fired after about 10 months. I lay awake for weeks trying to understand what happened, and why I couldn’t seem to do what others did so well. I realized that I loved thinking about and talking about and designing the Vision for what the company should be, which ultimately was disruptive to an organization that had already made its decisions about the future, and was in pure execution-mode.
I think that what makes me a good entrepreneur — the ability to paint a picture about the future and get people excited and working toward that — is what made me a failure in an environment when the vision was dictated by executives well above my pay grade.
What do you do fun?
Hang out with my family. Do crossword puzzles with my mom. Take long walks and talk with my friends. Climb mountains, when I can convince anyone to do it with me.
Do you have a hidden talent?
I can speak Munukutuba —a Bantu language— and Ob, whobich obis oba lobanguobage thobat woborks lobikes gobibboberobish.
What is your favorite mobile app?
I still spend most of my subway time on Google Reader or my Kindle (for Android), but (and this is geeky) I also like my banking apps, that let me deposit checks by taking pictures of them. Smart. Easy. Useful.
What do you do to help focus?
I take breaks when I need them, which allows me to concentrate for insanely long periods when I have to.
Cool Kid or Nerd in High school?
I was an awkward nerdy kid who tried way too hard to be cool. I’m pretty sure my red Esprit bag helped my case, but it just. Wasn’t. Enough.
Any words of advice for up & coming entrepreneurs who are trying to get their products noticed?
I think one of the most important traits for an entrepreneur is perseverance. You’ll do pitch after pitch after pitch after endless, mind-numbing pitch, before you get enough exposure that people start coming to you. You’ll find your reward one day when someone you’ve never met comes up to you and says, “I love/hate/have seen/have heard of your company!”
What are the three must have Fall trends that every stylish woman should own?
A deeply cool work bag (mine’s Phillip Lim 3.1 from Barney’s COOP) A jeweled collar (Karl at Net-a-Porter) Printed jeans (mine are from Zara)
What is your favorite trend for the season?
I still live in loafers and brogues, which have been in for a few seasons now. I’m getting old, so comfy is a major consideration.
What does it mean to be business savvy?
Not sure, but if you know anyone who is, we’re always looking for employees at Style for Hire.
What was the best advice ever given to you? Who gave it to you?
“Baby keep ya head up, when the road is hard never give up” — Tupac Shakur
Who is your ICON?
Nate Silver, political statistician from the NYT
What is your definition of perseverance?
I’m pretty sure that doing an interview at 10:30pm on a Friday would qualify. :)
Keep up with Cindy: Twitter, LinkedIn, Facebook, and Style for Hire
This interview was conducted by WIM intern, Jadine Joseph