Jaclyn Johnson is the 33-year-old founder and CEO of Create & Cultivate, an online platform and offline conference business. It's her second self-funded company and one she says is set to make just under $10 million in revenue this year.
Her events, draped in millennial pink, have drawn thousands of attendees in the past six years. The conferences have hosted an array of bold-faced names including now-British royal Meghan Markle, beauty mogul Kim Kardashian West, actress/producer Issa Rae and feminist icon Gloria Steinem.
Still, as she writes in her new book "WorkParty," it wasn't long ago when she struggled with the lowest points of her professional career. This era, and the lessons she took from it, have shaped her as a leader and an entrepreneur.
In 2009, just a few years out of college, Johnson was on top of the world. She was working a six-figure job at IAC, the corporate parent today of companies Tinder and Match. But after a year on the job she was given an ultimatum: take a salary cut or move across America to work for IAC's sister company Citysearch.
"When I was transferred at my job from New York to Los Angeles, I went in like 'big hopes, big dreams,' I'm going to have this new job that's really exciting," Johnson tells Make It. "And spoiler alert: I ended up getting laid off in that job. So, not only am I in a new city, I no longer have a job and I had zero connections."
This sparked an era Johnson calls the "Pizza Cry-Fest 2009," where she slept in everyday and opted for pizza over pep talks for three weeks. Afterward, she was too embarrassed to do more than email and hole herself up inside her apartment.
Within a few months she had put herself back into the outside world. She freelanced and ran her lifestyle blog "Some Notes On Napkins." This blog and other work led to partnerships with brands such as Ralph Lauren, Mercedes Benz and Target.
Those partnerships, in turn, led to visibility. After hearing Johnson speak on a panel at a fashion event, the trade show's president approached her and said, "I want you to be our director of marketing."
"It was enticing, I was three months into freelancing and I wasn't having killer success at the time," Johnson recalls. "The thought of a nine-to-five, health benefit situation sounded great, but all of a sudden it was like I blacked out and these words were coming out of my mouth: 'No, no. You should hire my agency.'"
The exec agreed and asked her to travel across the country for a pitch.
"I went home and I was like, 'What did I just do? I don't have an agency this is all a lie,'" Johnson says. "But I came back and told my business partner at the time, 'We need to file an LLC. We need to start a company, we need to get a website and then we need to fly to New York and pitch this client."
It's an approach that more young entrepreneurs should take, writes Johnson in her book. "You're never going to have all your ducks in a row or the experience you 'need.' So all you need, at least at the onset, is the gusto to say 'yes.' Confidence begets confidence." For Johnson, her confidence and excitement came from the fact that she knew she could accomplish what she promised.
She and her then-partner landed their first account and soon after launched No Subject, a marketing company, in 2010. "I think one of the best qualities of being a young entrepreneur is naivete," Johnson says. "Having nothing to lose is the best feeling in the world because you're able to bring things to the table that you're not really sure you can necessarily do."
While running No Subject, Johnson still felt isolated and wanted to meet with other like-minded women entrepreneurs. With nothing but the money she saved from her previous jobs and some income from No Subject, Johnson put together the first iteration of Create & Cultivate conference, attended by 50 people, in 2011. For three years, she lost money on the conferences.
Johnson continued to run No Subject on her own, hustling to make events happen. "When you're a small business owner, it means you are H.R., you're finance, you're the creative director, you're the account executive, you're all those different things and that can last for a very long time and it did with me," she says. "We wanted to get clients so bad sometimes that you know we were willing do whatever it took."
At times, that meant toggling between hosting events and bussing tables for them, all while wearing fancy dresses and high heels. On another occasion Johnson scrambled to create the illusion of a bustling office and a big team to win a coveted client. She purchased IKEA desks and paid friends to work from No Subject and look busy.
"It worked and it was awesome. That client ended up being a client for close to five years," Johnson says. "I told them that story at one point and they just thought it was funny."
In 2016, she sold No Subject to Small Girls PR for an undisclosed amount and invested $50,000 from the acquisition into Create & Cultivate. After the sale and what she calls a successful year in the stock market, Johnson had a reported income of $700,000 in 2017. But she notes that isn't her normal salary as she usually makes around $160,000 a year. Johnson currently oversees 10 full-time employees and has yet to take on any outside investment.
"When I first started my companies, I was so emotional and passionate and every failure, every bump in the road felt like the end of the world. It was really soul crushing," Johnson says.
"But as a boss and a CEO for the past 10 years now, when things come my way I'm able to handle them more meticulously, more strategically and less emotionally, which is a lesson you learn over time. It does get easier and you get better."
Like this story? Subscribe to CNBC Make It on YouTube!