animation of lady teaching a class and then creating oils in a kitchen
Maya Ish-Shalom
Maya Ish-Shalom
Work & Money

5-Figure Side Hustles

Boss sisters earning $15,000 to $40,000 a year outside of their primary jobs share secrets to getting paid.

Christy Pruitt-Haynes, 42
Day job: Human Resources Strategist
Side hustle: Buying investment property
Income: About $40,000 a year

The Nashville native lived in her first home for three years before renting it out after she moved and eventually selling it for a profit. Pruitt-Haynes had purchased the property back in 1995 when she was 20 years old through a first-time homebuyer program. “It was zero down and I only had to qualify for a mortgage that was 60 percent of the purchase price, which was $65,000. The other 40 percent was an interest-free grant, and repayment was deferred on that portion of the loan for five years. That made my initial mortgage only about $300 a month for the first five years.”

She repeated this pattern each time she purchased a new residence for herself: renting out the old one, then selling it. In 2012, having sold six of her homes, the Trading Spaces fan decided to purchase subsequent properties as investments. Her hustle incorporates two strategies: buying and holding (aka becoming a landlord) and rehabbing then reselling (aka flipping).

Pruitt-Haynes purchased the most recent house she flipped for $140,000, spent about $50,000 on renovations and sold it for $245,000 — a profit of $55,000. “After it was finished in April, I held it for a month. Watching the market, I knew things sold quicker in May,” she says.

These days, the mompreneur has made house flipping a family affair with her husband, daughter, mother, sister and niece involved in different aspects of the business. “As a Black woman, I know others like me were excluded from the opportunities of owning property for many years,” she says. “Real estate is one of the ways to create generational wealth, and that is something that I wanted my 15-year-old daughter and 18-year-old niece to see. And I needed the girls to know they are capable of not only owning their primary home, but also of owning additional homes and helping to create that possibility for others.”

Keys to her success: Pruitt-Haynes works with a realtor who knows what areas to invest in and specializes in finding properties that need to be rehabbed. She’s found contractors she can trust. She belongs to a Facebook group for real estate investors in her city and watches the market for sales trends.

How you can get started: Rising occupancy rates and a surge in rental growth favor investors who are landlords. Home-selling markets are cyclical, with profits for flippers declining for the time being. That’s just one reason now is the time to invest in education before purchasing investment property when the market heats up. Start learning for free at sites such as investopedia.com, thebalance.com and thestreet.com. Some pricey house flipping seminars are scams . Don’t fork over money to anyone promising to make you rich.

Hilary Beard, 56
Day job: Journalist and author
Side hustle: Personal development coaching
Income: About $15,000 to $20,000 a year

No stranger to reinvention, Beard left her corporate career decades ago to become an award-winning journalist and author. The Great Recession of 2008 caused her to take another leap of faith. “I felt called to do something greater than myself. I didn't have any work for nine months, but somehow I felt I'd be fine. I took everything I'd ever learned that I thought might be helpful to someone in distress — from how the brain operates when we're afraid to how to write a business plan — and packaged it to offer as a free community course,” says the Philadelphia native.

After Beard presented her free, eight-week seminar to 435 members of her megachurch, her fellow parishioners began telling her, “You could charge for this.” Beard says, “I had no idea. I was just sharing and trying to do something helpful for people.”

In 2011, Beard enrolled in a year-long coaching program. Helping others live their best lives has been her side hustle ever since. “Coaching gives me a revenue stream that I control,” she says. Once or twice a year she offers a group coaching program, which includes in-person and videoconference sessions. Although members of her church are her main clientele, she’s developing a social-media marketing plan to grow her business.

Now, she’s helping others take that leap of faith. “As a result of working with me, people who are outgrowing their job or career push past fear, uncover their current passion and develop a strategy,” she says.

Keys to her success: In addition to her year of training, Beard got unstuck by shifting gears and taking stock of the skills and knowledge she’d amassed, personally and professionally. Then she began figuring out how to monetize them. To others seeking a rewarding change, she says, “Move in that direction and the universe will put together your path.”

How you can get started: Search “life coach” at the U.S. Department of Labor’s Bureau of Labor Statistics (bls.gov) for details about the profession.

Emorie Vasquez, 38
Day job: ESOL (English for Speakers of Other Languages) teacher
Side hustle: Holistic health care sales
Income: About $18,000 a year

The Newnan, Ga., resident turned to essential oils to help her youngest daughter with her respiratory and immune support health issues. Because the natural remedies worked so well for her daughter, the mother of two started working with the doTERRA essential oils company as a holistic health care educator. Vasquez speaks at retreats and businesses, and clients purchase essential oils through her personalized web page.

Vasquez is paid a weekly commission and monthly bonuses based on sales. She also gets a percentage of sales made by salespeople she personally enrolled. “Our team currently has 500-plus customers and builders [recruits]. Fifty percent are on monthly orders and the other fifty percent order every couple of months,” she explains.

Keys to her success: Vasquez connects with clients via the company’s social media. Free samples and word-of-mouth also help to attract new clients. “I keep customers by adding them to our virtual group, checking on them and inviting them into my home to learn how I personally use these products,” says Vasquez, who diffuses oils and drinks water infused with citrus oils like bergamot, wild orange and grapefruit as part of her own wellness regimen.

How you can get started: In multilevel or network marketing, individuals sell products and services such as cosmetics, jewelry, supplements, fitness systems and phone services, often through word-of-mouth and direct sales. Typically, distributors earn commissions for their own sales as well as sales made by people they recruit. Many such companies sell quality merchandise at fair prices. But the Federal Trade Commission cautions that not all network marketing programs are legitimate. Also, out-of-pocket costs for training, inventory, registration or marketing can add up. Learn more by searching “multilevel marketing” at consumer.ftc.gov.

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animation of lady teaching a class and then creating oils in a kitchen
Maya Ish-Shalom