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99 Problems: Gilt Groupe's Founders On Dealing With Frenemies

Alexis Maybank and Alexandra Wilkis Wilson also offer advice on being in business with friends and what to do when you don't want to recommend someone for a job.

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Alexis Maybank and Alexandra Wilkis Wilson started flash sale site Gilt Groupe in 2007. A year ago, the company was valued at $1 billion. Alexis and Alexandra share the story of how they went from best friends to best friends and hugely successful business partners in their new book, "By Invitation Only." They answer your questions about fashion, career, and friendship below.

A friend is helping me build a website for a business I’m working on. This friend is doing me a big favor, really — I’m mostly paying her through dinners here and there since I don’t have a large budget for marketing but I know a website is integral to my project. But since I’m not paying her real money I’m not really at the top of her priorities list. I think she wants to help me and see me succeed and make the site good, but she also wants to do her PAYING jobs and have a life. I want to get the ball rolling on this thing and execute my vision, but I don’t want to be too overbearing or unreasonable and ruin our friendship. How do I balance this when both my friend and business are very close to my heart?

We are big believers in communicating. You need to find the right moment to speak openly and honestly with your friend to tell her how you feel. Explain that your friendship comes first, but that your website is incredibly important to you. Explain to her why speed is critical and why your website is integral to your project. Don’t assume that she knows all of this, she may not. You may also want to ask her if there is anything more that you can do to motivate and incentivize her? She may have a good answer for you that you hadn’t considered. And finally, have you considered compensating her with stock options in your future business? If your friend becomes an owner in your business, you might find she becomes a lot more motivated to finish the task at hand. There is truth to the phrase “You get what you pay for.”

I have a wonderful job at a company I love. There is a job opening here that is a pretty great opportunity. I happened to mention it to a friend who is in my line of work and wants the job, but I am mixed about recommending her for the position for two reasons: one, I'm not sure she's right for it, and two, in all honesty, I feel competitive with her sometimes, and I don’t want to encounter that on a day-to-day basis should she in the slight chance land the gig. Can I get out of recommending her? SHOULD I? Or should I suck it up and just pass her name along?

This is a tough situation. You need to consider your friendship, the good of the company and your own role in the company. If you genuinely feel that your friend could be a positive addition to your company, than deep down, you probably feel like you owe it to your company to recommend her. However, you will need to speak with your friend and openly communicate some of your fears about being competitive and how working for the same company could impact your friendship. There is no such thing as over-communication, but if you avoid certain conversations, you may find yourself being regretful later. If you have any doubts as to her skill sets for the role, then you probably shouldn’t be recommending her and that will probably be a relief to you!

I’m in business school and I notice that the male-female working relationships are a bit strained. For some reason a lot of guys end up working in all-male groups and a lot of women end up working in all-female groups. I know studies show that mixed workgroups tend to perform the best and I don’t want to feel like I’m short-changing myself by not having that experience in class. How can I bridge the gap with my male classmates?

A good place to start bridging the gap would be through existing relationships. Are you currently friends with any males in your class? Do you have a good relationship with any of the guys or do any of your female friends know any of the males well? If so, reach out to a man you know and openly express your interest in partnering together. It probably would help to highlight any of your skill sets that the all male groups may be lacking.

I work in a very professional environment that requires buttoned up office attire, but my boyfriend's a filmmaker. Who's in a band. When we meet up after work, everyone else looks cool in jeans and t-shirts, while I look like a corporate dork. How can I transition my work wear to grunge bar-appropriate without doing a total wardrobe switch?

Layers, layers, layers… Sometimes shedding layers in clever ways can evolve the corporate look into cool. It is hard for any woman to make a skirt suit become grunge bar-appropriate, so maybe stick to separates consisting of pants with jackets or you can work with dresses. Think about carrying some fun accessories like chunky jewelry or platform heels in your handbag to spice up your look after you leave the office. Lastly, think about investing in a really cool leather jacket which you can wear to and from work but not in the office.

As a hobby, I make bags and wallets from recycled materials. My friends love them, and I've made a little money selling to friends-of-friends. I have no business knowledge or formal training, and while some people tell me “starting a business is all about common sense,” I have no idea where to begin. Investors? Mini trunk shows? How do I take the next step and make this into a real business?

First of all, congratulations! We love hearing about people who turn their hobbies and passions into a potential business. We are big believers in finding partners with complimentary skill sets (as well as personalities). Do you know someone who has more of a business background who might be interested in teaming up with you in some capacity? Do you have friends who might know someone?