Her boss wouldn’t promote her because she "smiled too much.” Now her million-dollar business gives her a lot more to smile about.

When Kathy Goughenour asked her boss what it would take to get promoted at her marketing job in telecommunications, he advised her to get an MBA.
"It took me two years … because I trusted that that was really what was holding me back,” she recalled. “I got the MBA. The very next promotion was to a woman half my age.” At the time, she was 40.

"So I went to my boss and said, ‘Now tell me why I didn’t get the promotion?’” she said. “And he goes, ‘You want to know the truth?’ And I said, ‘I wanted to know the truth two years ago.’ And he said, ‘You laugh and smile too much. And until you change that about yourself, you will never go any further in this company.’"

She left and started her own business as a virtual assistant, one where her big smile was not a liability. Today, she runs Virtual Expert Training from her home in the woods of Black, Missouri, training future VAs to start their own businesses. She built Virtual Expert Training to more than $1 million in annual revenue, all the while having fun and donning her signature headgear, the tiara, in her virtual classes.

Kathy spoke at a webinar I moderated with Helena Escalante, entrepreneur-in-residence at the New York Public Library Thomas Yoseloff Business Center, on April 12. (The next event, on building multiple revenue streams, is today, May 12, at noon EST. You can register here; recordings will be sent to all registrants.)

We designed this virtual seminar to empower professionals, especially those navigating job loss or employment insecurity—with the tools and mindset needed to start and grow their own business quickly. Many people are considering entrepreneurship for the first time, not out of luxury but necessity. The good news: Some of the most iconic companies in America were born in downturns. And it’s very possible to move from idea to income rapidly.

Kathy spoke on a panel with Jason Allan Scott, a serial entrepreneur and former Y Combinator founder who has started businesses in events, podcasting, and pet health supplements, and Evan Fisher, founder of Unicorn Capital, a business plan writing firm, and founder of FreelanceMVP, a community for freelancers. Last week I did a deep dive into Jason’s advice on starting a business rapidly; next week I’ll look at Evan’s.

For today, I’m going to look at Kathy’s practical, inspiring strategies for launching a side hustle, freelance service, or scalable solo business on a shoestring.

Tip #1: Stop waiting to start your business … until you have everything in place, everything is perfect, and you know exactly what you want to do.

“What I have found working online since 2001 is that you change what you do constantly,” she said. “You change who you work with depending on what's happening, how you like it, or don't like it. And the faster you start making some money and doing the work, the faster you know how to do that."

"And then you just move on to the next thing and the next thing and the next thing. It's just amazing. This is what I did not know when I was in the corporate world, that there are so many ways to make money."

Tip #2: Stay open to the opportunities all around you.

When Kathy started the business, she and her husband were buying and selling real estate. That was when her antenna went up: She noticed many real estate agents were unsure of how to market their businesses.

“I said to the real estate agents, ‘Your marketing is terrible, your website sucks.’ And they said, ‘Fix it for me,’" she recalled.

“I can do that,” Kathy told herself. Using Google, she researched the steps she needed to help them improve their sites. She didn’t know she was becoming a virtual assistant until she asked a real estate agent if she could work from home. He said ‘Yes,’—and told her she was a virtual assistant. That was the first time she saw her services as fitting under that label. “So that's how I got started,” she recalled. That was in 2001.

Tip #3: Have an ideal client in mind.

One benefit of having your own business is working with the clients you want, as long as you sell something they want to buy. “It’s as easy as thinking about ‘Who needs what I'm offering, or who do I most like to work with?’” said Kathy.

Once you know the answers, update your LinkedIn profile to state what you offer and who you work with, she recommended.

Tip #4: Find a comfortable way to sell.

Once you’ve identified your ideal clients, make the most of opportunities where you are interacting with them. Ask, “Have you ever worked with [fill in the blank of what you're wanting to do]?” she suggested.

“Let's say it's a bookkeeper,” she continued. “Ask them, ‘Have you ever hired a bookkeeper? Great. What did they do for you? What was your favorite part? What was your least favorite? How much did you pay? What do you feel like you would pay?’”

After 15 minutes of asking potential customers questions like this, she said, “You get tons of great information … and about 20% of them say, ‘And by the way, I was looking for a bookkeeper. Well, I'd like to hire you.’ That's how I did it.”

Tip #5: Reach out to potential allies with the same target customers as yourself.

When Kathy was a real estate VA, she contacted website companies and asked them if they were having problems keeping their clients.

If they said yes, she’d ask, “What's the reason?” Often, it was because they didn’t know what to post or lacked the time to create it. She would then ask, “What if you refer people to me? And I refer people to you. You refer people to me who need the content … I refer people to you who need a website.”

“And that's how I built my business to over six figures,” she said. “Just that. I did nothing else.”

Tip #6: Pay attention to requests you can’t fill … yet.

“People would say, ‘Can you do blah, blah, blah?’” she recalls. “I'd say, ‘Can you spell that? Sure. Let me get back with you on what I'll charge you for it.’ I would go Google it and figure it out.”

Tip #7: Look for opportunities outside of your local market.

Once Kathy’s VA business was humming, she realized she could earn more outside of her local market. “I'm in the Midwest, and Midwest houses are cheap compared to those on the coast,” she says. “So I very quickly stopped marketing to local people and started marketing to those multimillion-dollar homes in California, the state of Washington, and Boston.”

She raised her prices until she hit a ceiling she set when it came to closing sales: “50 percent yeses, 50 percent no's is when I know I've got the right price,” she says.

Tip #8: Keep your overhead low.

Kathy recommends using free tools such as Gmail and Google Docs, and low-cost services such as PayPal or Stripe to get paid.

“Even if it's creating training that you want to sell, you could do it all there for free,” she says. “So don't buy a bunch of stuff. You don't need anything yet—just start making money.”