It was 2009 when Dave Green was standing in line at the post office near his Los Angeles home and a woman approached him to ask about his T-shirt. He was wearing a shirt with the words “Mystery Trip" on the front, a nod to quirky trips he'd been setting up for his friends since the late '90s—he'd take his friends to visit various places around L.A., without telling them where they were going in advance.
“Here was this random person in line asking me if she could book a trip for her husband's birthday," Green remembers. “I'd never really thought of it as a business until that moment."
Turns out, it was the right moment. A longtime corporate recruiter, Green was going through a divorce and looking to bring more levity in his life. Taking friends on these trips made him happy, so he decided to offer the woman a trip for her husband. Not too long after, Green decided to make it a full-blown business, naming it Mystery Trip, and notified his network. Inquires came pouring in, and pretty soon he had a solid side hustle.
In 2011, he received $1,000 from The Awesome Foundation, and in 2012, he was written up in the local press as a "best of" activity in L.A. By late 2014, corporations were interested in what he was offering. He quit his full-time job the following year and hasn't looked back. These days, he puts on trips for big companies in cities across the country. He has a small staff and expects to bring in around $600,000 in sales by the end of 2019.
Not bad for a side gig.
Believe that you not only have a good idea, but that you can do it. You have the skills and smarts and know-how to surround yourself with the right people and take your side hustle to the next level.
—Dave Green, founder, Mystery Trip
More than 1,300 miles east in Oklahoma City, Amy McCord Jones is pulling in similar revenue numbers with her company Flower Moxie, which enables brides to purchase wedding flowers straight from wholesalers at affordable prices. McCord Jones is a former chemist and turned to software sales a few years into her chemist job because the sales role involved travel and she wanted to see the world.
While she enjoyed being on the road, she also kept her eyes open for side hustle opportunities. In 2007, she and her family purchased a wedding chapel in an up-an-coming part of Oklahoma City and started holding weddings at the venue. When she was laid off two years later, she felt relief.
“I was ready to leave my corporate job; I would fly home on Friday night and then plan weddings all weekend," she remembers. “It got to be too much."
But by 2014, she was getting burned out on wedding planning and decided to try to cut out middlemen in the flower industry. The plan worked and today she's in the process of selling the chapel and running Flower Moxie full-time.
“Today, I have 65 wholesalers that I work with from across the country," she says. “I will send orders from brides to the wholesalers and then organize the shipping and picking up. The business has done really well; in my first year I was bringing in around $5,000 to $10,000 per month and now we are bringing in around $20,000 to $60,000 in sales every month."
Interested in turning your side hustle into a profitable business? Here are a few tips to help you move toward profitability.
1. Stick with it.
“A lot of success comes from perseverance," says Green. “People will say no to you and you will start doubting yourself; that is normal. Set daily, weekly and monthly goals for yourself. If you are working a full-time job, this may mean staying up late and getting up early [...]. Be willing to do those things.
"Everyone will have an opinion about what you're doing; it will be up to you to filter them out and focus on the task at hand."
2. Get your finances in order.
Even before she was laid off, McCord Jones worked hard to live below her means—something she recommends for anyone who has a side hustle.
“If you don't have a lower cost of living, you will set yourself to be dependent on a corporate salary," she says. “Give yourself breathing room, and look at your expenses. [...] And having six months worth of savings before you quit your full-time role is always a good idea."
In addition, it pays to talk with lenders about small-business loans and small-business credit cards. Especially when cash is tight or you're waiting on inventory or payments from clients, these strategies can help save your side hustle and make it even more viable as you consider leaving a salaried job.
3. Delegate the things you dread.
“Make an 'I dread this' list," suggests McCord Jones. “And force yourself to hire people. One of the biggest things I see business owners fail at is to think they can do finances, taxes, SEO, marketing, you name it, and in reality they have no interest in doing those things. If your side hustle is making money and you think you could dedicate your time elsewhere, hire for the things you hate."
4. Believe in yourself.
“Ultimately, success comes down to believing in yourself," says Green. “Believe that you not only have a good idea, but that you can do it. You have the skills and smarts and know-how to surround yourself with the right people and take your side hustle to the next level."
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