Entrepreneur’s Experience of Homelessness is Her Springboard to Success

By Laura McCamy

3 min read

“I really do believe that hitting rock bottom early can actually be a benefit,” says Crystal O’Connor (pictured), founder of business coaching site Moxie Entrepreneur and author of the new book, Unleash Your Moxie: A Girl’s Guide To Becoming Fiercely Bold, Incredibly Happy & Practically Superhuman. “You will far exceed the success of someone who has been handed everything early on.”

She should know: She started out her adult life homeless at age 18. That early experience helped her build the resilience she needed to risk starting her own business.

Struggling on the Street

After graduating high school, O’Connor moved into a beat-up Datsun 210 to escape a bad family situation. She went to work and to community college classes and then drove around to find a safe place to sleep at night. “I didn’t have much to my name,” she says. “I had a pillow. I cherished that pillow,” she recalls. “There was a lot of shame involved in that.” She soon found it difficult to keep up the façade that she was living a normal life.

After a couple of months, O’Connor couldn’t face another night on the street. She cancelled all her classes, sold her books for $40 and used the money to stay in a hotel. She started looking for a full-time job that would allow her to rent an apartment. “I had to start thinking differently,” she says. “I remember using a pay phone as if it was my residence.” She sent out resumes and camped out in front of the pay phone waiting for calls.

It was this time in her life that taught O’Connor to “ask for the sale” — to take a risk and ask for exactly what she needed and wanted. When O’Connor got a job interview, she felt insecure because she didn’t have much experience or the right clothes. But she borrowed a dress and showed up for the interview. She got the job. “I made it happen with what little resources I had,” she says. “A lot of times it’s just showing up.”

Ups and Downs

O’Connor’s new job paid her enough to rent an apartment. By the time she was 23, she was able to go back to college. She built a career in sales and marketing. She got married. Then, in her mid-30s and with three small children, O’Connor went through a divorce. She was making what she thought was a good income from her sales job, but it wasn’t enough to pay the bills. In 2008, the recession delivered the final blow, as the clients she worked with began to go under. “I realized I had to do something drastically different,” she says.

She started by blogging and connecting with other bloggers. In 2009, she launched Fearless Ambition Magazine, an online publication with the aim to empower entrepreneurs. “In my mind I saw publishing being the foundation” of entrepreneurial enterprise, she says.

Unleashing Her Moxie

In 2010, O’Connor founded Moxie Entrepreneur. She has worked as a consultant with everyone from solopreneurs to big corporations, helping entrepreneurs develop multiple revenue streams and offer their services to groups in order to increase their profits. “Because of that high leverage, the profit margin is much wider; it can fund your business,” she says. “Leveraging your business as soon as possible is the most important thing.”

O’Connor notes that she often works with clients who have great websites but little or no revenue because they aren’t creating urgency and turning prospects into customers. “It doesn’t have to be pushy,” she says. “It could be in conversations at a networking group. It could be asking for referrals. It could be having a sale on your Facebook fan page.”

Her early journey into and out of homelessness forced her to learn how to put herself forward, even when it felt scary. “Moxie is asking for the sale. It’s stepping out. It’s marketing yourself,” O’Connor says. “Sometimes feeling silly because you’re doing something everyone else isn’t doing.” She advises other entrepreneurs, especially women, to get out there and follow your vision, even if you don’t feel completely qualified. “You’re never going to completely feel prepared,” she says.

Information may be abridged and therefore incomplete. This document/information does not constitute, and should not be considered a substitute for, legal or financial advice. Each financial situation is different, the advice provided is intended to be general. Please contact your financial or legal advisors for information specific to your situation.

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