Reprintable Interview Questions - Personal and Advice

Do you have any mentors in Manhattan or elsewhere?

I do have a mentor - Richard Branson. We met in Toronto at the Spoke Club years ago and bonded instantly over the fact that we both started magazines when we were 15. He's an incredible man, very down to earth and always genuinely interested in what I'm up to. I really admire him and love spending time with him.

Do you meet many people in media?

I actually have quite a lot of friends in media. I've become good friends with the features editor of Town and Country - we go to dinner and swap stories. He tells me about the crazy press trips he gets sent on. He's gotten to race prototype race cars through southern France, and fly jets... he has so many great stories!
I met Helen Gurly Brown at an Oscars party in LA, and Tina Brown at the Talk Innovators and Navigators conference at Bacara Resort in Santa Barbara.

Do you have any brothers or sisters?

Yes, I have a brother named Simon who I'd do absolutely anything for. When we were kids we used to used to fight like cats and dogs but now we're best friends. He's a brilliant guy. He gives talks at aerospace conferences and he's always looking for ways to better the world.

What do you see yourself doing in the future?

I will be focusing on growing my online businesses. My goal is to double their size every year. We are also in the process of launching several other sites to create a larger network. I also really love putting on charity events, so I'm sure I'll continue to do that too.

Where do you live in New York? What is your apartment like?

I rent in a pretty famous building in the West Village. It gets referenced in lots of novels, like the Shopaholic series, and Mandy Moore lives on my floor. Anne Hathaway used to live in my building, and there's lots of models and 30-ish professionals. Josh Lucas told me that my exact suite used to be Jennifer Connely's and I must have moved into it right when she moved out. He said she lived here with her son for about a decade.
My apartment has a bedroom on the second floor and is covered in huge pieces of art. The ceilings are about 20 feet tall and the bedroom looks over into the living room. I just got shot, in my apartment, for the pilot of Digital Cribs. My place is so full of gadgets - I'm such a geek!

What are you passionate about doing in your spare time?

I started a two events companies called The F.A.M.E. Project and Open Social Sundays about a year ago.
Open Social Sundays puts on monthly brunches with about 40 people. It started out as CEO's in dot com, but it's expanded now to include fashion designers, editors at magazines like Vogue and Town and Country, art dealers and actors. The F.A.M.E. Project stands for fashion/arts/media/entertainment, and is mostly cocktail and dinner parties for people in film and tv, fashion designers, media/editors, celebrity actors, models, and execs in the entertaiment and fashion industry.
All profits from both events companies are donated to charity. I pick a different charity each time, and give out a postcard with information about the charity and what people can do to continue to help after they leave. Instead of charging for the brunch, I ask for a donation of their choice amount, and raise extra funds through silent auctions and sponsorship. It's a lot of fun and I love watching everyone make new business contacts and friends. [Read more ABOUT HILARY'S EVENTS.]

I'm working on some other ventures as well. I'm starting two brand new sites and another events company that's based on the New Faces casting concept. I'm also working on developing a reality show based around New Faces. I'm really excited about it!

Indulge me for a few minutes and describe your day (Thursday), please, with as much stop-watch accuracy as you can manage.

I roll out of bed at about 8:45am, shower and throw on a casual Tory Burch dress. I had a new programmer and a new designer starting today, so I made sure they were welcomed to the team and had instruction on what to do from the relevant project manager. I read over some internship applications, and pick a couple of good ones to interview when I get back from Burning Man. Then I'm off to the roof of SoHo House, the famous private members club, to have lunch with Tamsin Lonsdale, who founded The Supper Club, which is a private club that holds society-type events and dinners. She recently appointed me as an ambassador for the club because I have a large network of friends who are doing cool things. Basically, they'll throw a bunch of very high-end and fashionable events for me and I can invite people that I think would make a good member. After lunch, I have a quick meeting with Derek from Glam, to go over some details of our partnership and tell him about the new sites I'm creating. I am meeting the CEO of Glam next week for coffee. Then I run back to the office for a couple of hours to do some more work. At 4:30pm I have a meeting with Toby from Mint Digital, who shows me a proposal he made on how Mint can work with New Faces to produce large sponsored contests. They mostly only work with Fortune 50 clients, but he saw an opportunity with New Faces, which is really exciting! After that, I have a quick drink at Bobo, with my friend Victor Harwood, who produces several large conferences, such as Digital Hollywood and CES. From there I run home and quickly change into my nude Gucci dress, slip on some heels, grab my Rafe clutch and run off to a gallery opening in Chelsea, where a friend's art is featured. I stay for about 20 minutes, then I'm off to a dinner party at Norwood, another members club, with a bunch of friends. The topic was "State of the world: political policy" and we each had to bring one new person to introduce to the group. After dinner, I quickly stop by a BlackBook magazine party. I stay there for about an hour, then I go to a party at Scott Lipp's loft, which is packed with top supermodels, since he owns ONE Model Mgmt. My friend Michael Houghton's band is performing (with Tommy Hilfiger on the guitar!), and they are fantastic, so I try not to miss an opportunity to see them. My friends are going to The Box after, but at 2am I opt to go home and get some rest so I can do it all again tomorrow without being tired.

How did you become a part of the New York/Hollywood scene. When did that transition between Port Hope web geek and Manhattan scenester take place?

Living in New York, and being in the Hollywood and modeling scene, you just naturally meet celebrities here and there. I hung out with Josh Lucas at Sundance and then we both texted each other at the same time to invite the other to Anne Hathaway's dinner party at the incredible apartment she had with her ex. It's funny, New York is so small in certain circles that it's normal to find out that just coincidentally you have ten friends in common.

What famous person has been the most thrilling to meet and why?

Helen Gurley Brown definitely sticks in my mind because she founded Cosmopolitan magazine and, although it's not nearly a favorite of mine, she made it very successful and I have to respect and admire that. Jackie Collins is another person I respect. She has sold over 30 million books (which is not an easy thing to do - my father is an author - I know!) and is still so down to earth and friendly. Geoffrey Rush, Sofia Coppola and Hilary Swank were amongst the nicest and most talented people I've met. Besides that, Brad Pitt and Johnny Depp really have that obvious star quality in person. They are both absolutely gorgeous.

Do you keep in touch with any school friends from Canada?

Yes, although it's harder now that I live in New York City and rarely see them. Facebook helps though! I went to Trinity College School out in Port Hope, and a lot of my friends were from all over the world. My best friends from high school are actually living in Europe, Asia and Australia now.

What has been the most exciting part of having your own magazine, ebooks and online portfolio company?

I love getting feedback from clients and readers. It's especially great when I get emails from people who have read my modeling ebooks (sold on NewFaces.com) and want to let me know how much it has helped them and how much closer they are to achieving their goals because of the e-book.

What advice would you give to other young entrepreneur's to turn their dream into a reality?

Don't get discouraged. Starting a successful business takes more work than you think but it's doable if you have the will and determination to keep pushing yourself until you've reached your goal. Oh--and make sure you have a viable business plan that fills a gap in the market or is an innovative approach. Think everything out thoroughally.

Any motivation tips for young people?

Just believe in your dreams. Believe that you can get there. Don't slack or party too much. It's okay to relax but instead of watching TV why not read a book in a park or by the fireplace and actually learn something? I never watch TV - it's such a time-waster! The other important advice I could give is never do drugs or cigarettes. Seriously. I've never tried them but I've seen a lot of people waste away because of them. Just stay away.

What impact does the media have on young girls?

I think the media can have a very negative effect on girls self image. The media portrays an ideal that doesn't exist without a makeup artist, stylist, lighting, photo touch-ups and often hours of exercise a day - not to mention breast implants! How are girls going to be happy with themselves if they think they're expected to look like that in order to be attractive or sexy?

What makes you happy in life?

Spending time with my friends and my family makes me happy. When I was 25, I bought my parents a sailboat, and I love spending time together sailing when I visit them.

What advice can you give them to improve their self-esteem?

Don't compare yourself to the images in magazines. They're not real - they're fantasy. Concentrate on developing yourself as a person - learn things, take classes and read books, not superficial magazines. Get outside and don't wear makeup when you're not going out. You'll be surprised what a difference these things can make on your outlook on life.