This month we want to introduce Bailey Drake, founder and CEO of Orangutan – an app designed to help parents find & book babysitters on-demand. Bailey has been staying with us for the last month and has been working non-stop on her business. Discover her great story and how she came up with this amazing startup idea!

# 7 : Bailey Drake, founder and CEO

Bailey is a native of Charleston, South Carolina, who just recently moved from New York City to San Francisco. Bailey has been babysitting since the age of eight, loves coffee and good bourbon, is a gifted photographer and graphic designer and has designed a killer business model to revolutionize the way Mom’s and Babysitters engage. But let’s back up. Bailey attended the University of South Carolina where she studied Marketing & Management before, as she calls it, “self graduating”. After 3.5 years she realized she never wanted to work for a company that deduced she had the skills and knowledge they were looking for simply because she had a piece of paper that said so. She spent the next three months traveling to Nepal, Bali, & Australia. This was not a ‘I need to go find myself’ trip as you would suspect from a recent dropout, yet a ‘I need to get lost and have an adventure’ trip. “It was great,” she says. Bailey always knew she wanted to work for a startup. With a background in business and design she thought what better way to round out her arsenal of tools then to learn how to code. So, upon returning stateside, Bailey attended Epicodus, a full stack web development bootcamp in Portland, Oregon. After the course ended she started looking for jobs, as one does. She knew eventually she would start her own company but wanted to have the experience of working at a startup before starting her own. But you know what they say about plans….

This brings us to one crisp fall day where Bailey was watching the documentary The Startup Kids (definitely recommended). When talking on the topic of coming up with startup ideas it was said, something along the lines of, start a startup based on a topic you know well and are passionate about. Bailey thought, “What do I know well & am passionate about?,” her response was: bourbon, coffee, & babies. After going through the options she came to the conclusion that she didn’t want a bar, didn’t want a coffee shop and sure as heck didn’t want a baby. She brushed starting her own startup aside & went back to looking for job. It was shortly after this when talking with a friend who was in search of a flexible job that babysitting was brought up. Bailey, at this point, realized that the current players in the babysitting market weren’t fulfilling the needs of the end users. It wasn’t until her dad encouraged her to develop the idea further and see what comes out of it that she started to give the idea more weight. It’s been said that one of the earliest challenges a startup faces is giving it a name and logo. Bailey told herself that if she could name it and design a logo in four hours then she would continue down the trail of developing the idea out. She named it, designed the logo, and never stopped. She moved to New York to build her network and to focus on building Orangutan. In search of a CTO and to expand her network she decided to come check out San Francisco resulting in her moving into Startup Basecamp.

Some of the hardships I had to face…
Bailey said one of the hardest things about starting a startup, in general, is people are constantly trying to poke holes in every aspect of how you’re building your company. “Can’t let ’em get to ya,” she says. She says her current challenge is finding the right person to help champion Orangutan to market (She’s looking at you iOS developers). Bailey says putting yourself out there & expanding your network, helps solve this.
Has StartupBasecamp been useful?
“Yes, It’s been great living in an environment of people that are determined o make things happen”

To future entrepreneurs…
“Don’t stop fighting for your idea. Some days will be harder than others but wake up everyday and chase your vision”

Read smart, think smarter

Read smart, think smarter Bailey recommends: “The Narrow Road” by Felix Dennis. She says it’s a quick read and it’s one of those books that “tells it like it is”, giving a non sugar coated walk down the road to success.

Bailey’s motto…
Take risk, regret nothing, travel often.

Stay tuned with Orangutan

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