Gboyega Adebayo was used to working fifteen-hour days in consulting before launching Yencil, a website that allows users to buy and sell documents for a small fee. As a consultant, Gboyega sifted through mounds of paperwork and endured endless meetings. On hard days, he reminded himself of the perks of the business. He could travel the world, claim expenses, and enjoy upgrades and rewards. Then Covid changed everything.
Well, almost everything. Gboyega’s workflow didn’t slow down, but he was stuck in a small home office. There was no work-life balance and he was emotionally depleted. When his wife told him they were expecting their first child, he knew it was the perfect opportunity to reinvent himself professionally.
Gboyega is the baby of his family. At family gatherings, his older siblings would all watch in amazement as he navigated the internet like a true digital native. When Gboyega toggled between multiple apps to find a document for his sister, who was ten years older, his family watched with envy. “You should turn this into a business,” his sister said.
Gboyega didn’t take his sister seriously at the time. She’d commented partially in jest, and Gboyega was still consulting full-time. Besides, he lacked any formal technology training – he was no coder – to take on a new business venture. Still, he was intrigued, and his sister’s comment foreshadowed the next chapter of Gboyega’s career. This is the story of Yencil.
From Joke to Genuine Idea
Gboyega’s interaction with his sister in late 2019 stuck. Why did some people find it so hard to source documents online? Gboyega approached her suggestion like a consultant. Could he create a marketplace where people shared documents they’d created? He drew up a business plan that turned the casual idea into a potentially viable business.
Gboyega had no time to explore the opportunity further. His work hours were already insane. But all of that changed when the pandemic arrived. “I worked sixty to seventy hours a week, accelerating my career. I was on a path to making partner. But I felt like I could do much more.”
As a child, Gboyega had dreamed of becoming a rich entrepreneur. Until now, however, he hadn’t identified a passion or idea to pursue. He’d simply fallen into consulting because he was good at talking to people. Now that he had an idea that he believed in, he needed to channel his energies: What type of helpful tools would he offer? How long would it take?
He called one of his closest friends from college, Les Ragsdale, for honest feedback. If this was a crazy idea, he would return to consulting. Not only did Les like it, but he also wanted in, and soon they were on Zoom calls fleshing out the business.
But working with friends can be tricky. They were practically brothers, and neither wanted the business to jeopardize their friendship. They committed to being friends first and business partners second, hoping to never lose sight of their friendship in their pursuit of success.
Les and Gboyega soon brought on another close friend from the University of Virginia, Marc Hall, whose background was in cloud engineering. Thinking ahead, a partner who knew cloud storage and infrastructure would help the entire team navigate these big expenses as they grew.
Going Big Without Going Broke
The founders decided to focus on Microsoft and Adobe documents first. What if someone created an Excel document to help them balance their budget and wanted to share it with the world? They first looked online to ensure they wouldn’t reinvent the wheel.
Although they found plenty of document-sharing platforms online, most specialized in an industry (tourism, finance) or program (Excel). How could the Yencil team serve a larger audience while still billing themselves as the go-to site for niche industries? Was that an oxymoron?
Gboyega explains: “We didn’t want to brand ourselves into only one industry or category. Amazon starting with books proved that starting narrow was a successful strategy, and we believe that variety is an important part of our value proposition. So, starting with the Microsoft Office Suite plus Adobe PDF felt like a good balance of being narrow but not just being another niche website.”
Helping People Monetize Their Work
Irrespective of industry, Yencil’s goal was to help people earn money for sharing documents they’d created. Gboyega says, “We want to be the foundation of your side hustle and its growth. Our obsession is saving our customers’ time. For sellers, our product (and future products) will prioritize saving time as your side hustle evolves into a business.”
People looking for passive income don’t always have time to navigate loads of content. Yencil wanted to keep things simple. Customers would sign up and upload files in just a few minutes. The software would incorporate credit card processing to accept payments from buyers. The team also wanted to provide customers with analytics to help them better understand their target audiences. All of this would cost money that the team didn’t have.
Thankfully, Les is a full-stack software engineer. The team would be able to keep costs lean by building everything in-house. Gboyega says, “Front end, back end, everything. Les did it.” This kept costs down, and everyone kept their day jobs while they figured out how to find clients.
Finding Clients While Everyone Worked Full-Time
Gboyega had never been a salesman, but he was eager to spread the word. Les had built the platform, and despite originating the idea, Gboyega wanted to prove his worth. “My industry experience was technology business management, which is the most buzzwordy thing in the world. I help technology organizations operate like a business. While Les was building, I thought, ‘I need to do something.’ Let me start talking to folks. Let’s start talking to potential customers.”
Starting a podcast wasn’t part of Gboyega’s plans, but it gave him a platform to network with other entrepreneurs. He asked fellow founders for advice and encouraged them to spill the grittier side of building startups. Their stories helped him avoid making the same mistakes. Gboyega jokes that his podcast became a bit of a cheat sheet for future founders (but mostly himself).
“I wanted to talk to entrepreneurs and aspiring entrepreneurs, the side-hustlers, everyone,” Gboyega says. “I don’t aim to be Guy Ross. I don’t want to talk to a multibillion-dollar company. They’re just going to romanticize the night they slept in their car. I want to talk to you the night after you slept in your car.”
Gboyega and the team also experimented with direct messaging potential customers on social media, reaching out to Facebook groups and Reddit threads. Gboyega explains, “As we gain a better understanding of where our target customers live, we can pull them into the sales funnel. We are looking for awareness, interest, consideration, and ultimately, conversion.” They also reached out to their LinkedIn and social networks to talk up Yencil and get their earliest customers.
Jumping in With Eyes Wide Open
It’s at this part of the story that Gboyega discovered he was about to become a father. His consulting firm also wanted him to stay on as a director. But Gboyega knew that something would have to give. He couldn’t run two full-time jobs while spending time with his baby. This is when he decided to go all in. And, as Gboyega says, “It was scary because diapers are expensive.”
But Gboyega didn’t rush from corporate executive to bootstrapped founder. First, he outlined how much money he needed each month to survive, converting his savings into an entrepreneurial runway. He found gig work and independent contracting opportunities that gave him both time and flexibility so that he didn’t burn through his safety net.
It wasn’t just the diapers, but it was losing the steady paycheck that was most frightening. “When you’re running low on sleep, you don’t see a paycheck hit your account on the fifteenth, and you get your fiftieth ‘not interested’ email from a prospective client, negative self-talk can creep in. You start wondering if you made the right decision to put your family through the discomfort.”
Ultimately, Gboyega relied on the support of his wife: “My wife is amazing. She supports my ambition, the Yencil vision, and trusts that I’m giving everything to make this a success for our family and not just my ego. In addition to being a working supermom, she puts in that extra oomph to give me the additional time and emotional grace to work on Yencil.”
Gboyega also credits therapy with providing him with tools to combat self-doubt and help him stay mindful of how his entrepreneurial journey impacts all of the people in his life. “To me, mental fortitude is eighty percent of the battle as a full-time bootstrapper.”
As a big believer in therapy, Gboyega urges all founders to be mindful of their feelings because the journey can shake your core and lead to premature pivots or indecision. “For a lot of BIPOC founders, the primary (or only) obstacle is money – the capital to start, or the money to see the idea through. The unfortunate reality is that getting funded or getting a loan is harder for BIPOC founders. But I would advise not to solely focus on the money. Instead, focus on understanding and managing your fears and emotions that are wound up in the money.”
Yencil is currently in the growth phase and gaining momentum. Gboyega doesn’t regret his decision to make it his full-time job, but there are days when he finds himself wishing for his old paycheck. He’s savoring the time he spends with his new baby, his wife, friends, and extended family. It takes a village, after all.
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