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How One Student Turned $5k Into a Successful Beauty Startup

Prettier Please's stylists at work
Prettier Please's stylists at work

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Plenty of desk-toilers are bitten by the entrepreneurial bug at some point, but only a handful actually take the steps to get those bespoke bow ties for hamsters ™ off the ground. Count Prettier Please's Olivia Cranin among the few: the former marketing manager traded in her cushy Hearst gig for Columbia Business School. And, less than a month after graduation, her company—which sends makeup artists and hairstylists to your apartment for blow-dry-bar prices—is already profitable.

We sat down with Cranin (while her Prettier Please team took us from 'I think I brushed my hair this morning?' to fancy) to talk B-School, the fashion and beauty startup boom (she counts Hukkster's Katie Finnegan as a mentor), and what it's really like to work for yourself.

Quick! Tell us about your background, career-wise.

I just graduated a few weeks ago from Columbia Business School. I went to undergrad at Colgate University in upstate New York, and then I was working for four years in marketing at Hearst before I went back to school.

Why did you decide to leave your marketing job and go to business school?

I was at Hearst, but at a start-up that was incubated within Hearst and I was a marketing manager for that business. It was a personal finance app. I was one of the first employees, the second person on the marketing team, and then it grew a lot. I felt that I learned so much from building a new business, and then my job stabilized and I wasn't necessarily learning as many new things anymore. I felt like going to business school would give me a broader set of skills.

Did you always want to be an entrepreneur?

Yes, I knew that I wanted to do something in startups. A smaller and more open, collaborative working environment works better for me. I think that these blow dry bars are awesome—it's the new manicure, and affordable—but they're over capacity. I knew that there was a better way.

Were most of your classmates working on apps and more tech-focused ventures?

I'd say it's rare to find someone in business school who isn't working on a startup involving technology. I wouldn't define our company as a technology business, but it's still important to what we do. We take all of our appointments online, for example.

How did the idea for Prettier Please come about?

I started Prettier Please with my classmate as part of a "Launching New Ventures" class. We created a business plan to solve a problem that was very frustrating to us. We're at that age where all of our friends are getting married, and we have, if not a wedding, then a bridal shower, or engagement party or bachelorette party every weekend.

You always want to look a little special, and get your hair or maybe your makeup done, but spending your day running between appointments is stressful. Making yourself look better should be enjoyable, and it wasn't, so Prettier Please was a way to solve that problem.

What was your initial investment? How much money did it take to get your company off the ground?

My partner and I put in $5,000 and now we're profitable. So we haven't put any more of our money into it.

And what did that money go towards? Paying stylists?

Our stylists are independent contractors, so we don't pay them a salary. We give them a commission. That money went to things like getting our website up, doing some initial branding, uniforms, and getting our stylists set up with product sets.


Olivia Cranin

Was it difficult to run this business while you were still in school?

There were pros and cons. The obvious con is just time. But there were a lot of positives. We worked through the whole business plan in "Launching New Ventures." We went through everything from finding your market to building your financial model.

Were your professors open to it?

Business school is different from undergrad. You have a ton of free time. This year of school, I used all my free time to work on building Prettier Please as an independent study and I took a lot of classes that helped develop the company.

Are people into the idea of having stylists come to their apartment?

There are so many services that come to your home, in New York especially: cleaning services, Seamless, Couchsurfing. I think there is this increased comfort level.

Do your stylists work for you full-time?

We're very flexible with our stylists. They set their own schedules with us. Some work at a salon Monday through Friday and work with Prettier Please on Saturdays and Sundays. Some people have salons that open at 10am so they'll do early morning appointments.

What is your most popular service?

Blowout is the most popular service but it's time-of-day dependent. The blowout and makeup package, which is $120, is a close second, especially on the weekends.

What's the booking process like? How much information do customers typically give?

People in New York are always in some sort of rush. We try to do everything we can to make the time our stylists are there as efficient as possible. Customers typically book online, and then after you book you'll get a confirmation and you'll have a very brief survey that is a pre-consultation. We'll know what type of hair you have, what type of look you're going for, and if you're going somewhere special.

Your stylist will text you when he or she is on their way, like 30 minutes before your appointment. So if it's a blowout, he or she will remind you to have your hair wet before they get there. The stylists will also have a our lookbook on their smartphones when they get to the appointment, so you can look at the photos and get on the same page.


A customer, getting fancy.

How have you been getting new customers?

It's pretty much by word of mouth. I grew up in New York and went to high school here, so it's started as a personal network and friends-of-friends-of-friends kind of thing. We've done some partnerships with companies like StyleCaster.

Through Columbia Business school we did our thing for Spring Gala, which is like business school prom. And we were on Gilt City, which led to a lot of new customers who did not buy on Gilt but whose friends told them about it.

Do you have any plans for expansion?

I mean definitely geographical expansion. First, just the tri-state area. Then bigger cities like Chicago, L.A., San Francisco, and Philly. In terms of what we offer, broadening our service selection. Some people have talked about adding brows. I'd love to sell products. Both through our site and a select set of products from the actual stylist.

Would that be your brand or brands that you like?

TBD, but for hair we use Blow professional products. Stylists and customers really seem to like them. In terms of makeup, if the makeup artist is going to use a particular color you're not going to have that with you it makes sense to be able to buy it right there.

What do you like about being your own boss?

I love being involved in every part of the business. Especially early in a company, you get to work on everything from marketing to technology to finance and raising capital. I'm always switching from one focus to another, and that's the best way to learn.

And what do you find challenging about working for yourself?

This is a service business, and we're always responsive to our customers. I don't feel like I ever have a minute off. I work from the minute I wake up in the morning. I get up in the middle of the night, I'm glued to my phone. I want to make sure that everything is running smoothly. We're very customer-facing, so I need to be ready to interact with them at all times.

Who do you admire in the fashion and beauty startup world?

Obviously Birchbox and Rent the Runway. They've both done such an amazing job of bringing community into their sites. We definitely have a similar vision for the Prettier Please online experience. In the same way you can see how real girls look in Rent the Runway's dresses, we want to show how girls who may have similar hair types or skin tones to you look in our hair and makeup offerings.

I went to college with one of the founders of Hukkster, Katie, and she's been incredibly helpful with introductions. She's been such a great resource for talking through visions of our business.
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