After stepping back from her agency during a challenging pregnancy, Cole Shihan taught herself AI automation from bed and went on to build an online education business.
SINGAPORE — When Cole was placed on bed rest during her pregnancy in early 2024, the business she had spent years building suddenly became much harder to manage.
A mother of two and former digital agency founder, Cole had built an agency that she describes as a seven-figure business, with a significant portion of its work coming through government tenders. The business involved managing employees, suppliers, subcontractors, overhead and lengthy payment cycles.
Then her pregnancy forced her to slow down.
“I was running a lot of things,” Cole says. “When I got pregnant and had to be on bed rest, everything started to fall apart. What used to be flourishing now had me as the bottleneck.”
For someone accustomed to working constantly, the experience became a turning point.
Learning AI From Bed
While spending much of her time on bed rest, Cole began teaching herself AI automation.
Initially, her goal was practical: find ways to reduce the amount of work that depended directly on her.
But as she experimented with AI tools and automation, she began seeing another possibility — building services that could be delivered remotely while giving her more control over her time.
“I was working 18 hours a day, seven days a week,” she says. “I'd get home when my kids were already asleep. This way, I could be with them every night.”
Her first opportunity came through someone she already knew. A friend paid her USD 500 to build a website, fully built by AI.
That first project gave Cole a starting point. She continued developing websites, exploring AI automation and looking for clients through direct outreach.
She called potential customers, sent cold emails and continued refining the services she could provide remotely.
“It's a volume game,” she says.
She later began finding clients through Upwork, where she says one website project paid USD 6,350.
From Learning AI to Teaching Others
Cole’s experience eventually led her to create an online education business focused on helping others learn practical AI-related skills.
She currently operates two online communities on Skool.
Her established community, Paid With AI, has more than 1,000 paying members, according to Cole. The community focuses on practical skills related to AI, client acquisition, websites, funnels and automation.
Her second community launched more recently and focuses on helping members learn how to build an AI agency from the ground up.
The newer community gives members daily tasks designed to provide a structured learning process, with a goal of helping participants work toward securing their first paying client within 30 days.
Rather than positioning AI as a shortcut, Cole’s approach centers on learning practical skills and applying them to real business needs.
Building an Income While Staying Home
Today, Cole’s work combines online education with AI automation services and website development.
She reports earning more than USD 20,000 in September and approximately USD 15,000 in October. These figures are self-reported, include revenue from client services and teaching, and have not been independently verified.
Cole says the majority of her work is now remote, allowing her to operate her business without the daily routine that previously required extensive time away from home.
“I'm 99% remote,” she says. “I don't have to meet clients. I get paid before I start working.”
For Cole, however, the most meaningful change is not simply the way she earns an income. It is the time she now has with her children.
“I can be with my kids every night,” she says. “Teaching, automations and websites, all from home. I couldn't be happier.”
Her experience has become the foundation for Paid With AI, where she now shares the skills and processes she developed while rebuilding her own working life.
Community Now Open
Paid With AI's newest community is currently open to new members at paidwith.ai/sell.
The community offers a free seven-day trial, followed by a membership price of USD 149 per month. Members can cancel at any time.
Free resources and guides are also available at paidwith.ai/resource.
Individual results can vary, and Cole’s personal experience and reported earnings should not be interpreted as a promise or guarantee of income for other participants.
About Paid With AI
Paid With AI is an online education community founded by Singapore-based agency founder Cole Shihan. The platform focuses on practical applications of AI, including automation, website development, client acquisition and other skills used to provide services to businesses.
According to Cole, more than 1,000 paying members currently participate in her Paid With AI community, while her free weekly newsletter reaches more than 5,000 readers.
Learn more at paidwith.ai.
Media Contact
Cole Shihan
Founder, Paid With AI
Email: cole@paidwith.ai
Website: paidwith.ai
