“Success is not money; it’s when you put your head on the pillow at night and think, have I impacted people’s lives in a positive way?”

My favorite food is: Sushi My pet peeve is: People who don’t put things back where they belong

Lil Roberts

Helping small business owners level up

AN UPBEAT APPROACH. Lil Roberts is a profoundly positive person. Her attitude to life – people-driven, family-orientated and community-minded – has propelled her through a series of successful businesses, the first of which she started when she was 27. “I love the human condition, I love to build teams, and I love to solve problems. The combination of that has led me in life to be a serial entrepreneur.”

Lil’s outlook on life is reflected in her latest company, Xendoo, a cloud-based fintech platform specializing in online bookkeeping and accounting for small business owners. It’s a sector she’s incredibly passionate about supporting. “I believe small business owners are the backbone of America. When you think about all the big corporations in America, they all started as small businesses. Howard Schultz started Starbucks as a one-store small business.”

Xendoo has built technology that provides business owners with financial visibility to help them better understand the health of their business. “We deliver financial peace of mind to them. Taking the stress off of owners translates into them spending more time with their staff, family and ultimately focusing on doing what they love, building their business.”

A CULTURE OF CARE. While Lil is building a company that she hopes will become a household name, she chiefly measures its success by its impact on people’s lives. “Success is not money; it’s when you put your head on the pillow at night and think, have I impacted people’s lives in a positive way?” This attitude extends to her team, where she focuses on hiring heart-led people who are as kind to customers as they are to their fellow team members.

“I love to see people become part of our company. I’m very work-family oriented because of the childhood that I lived. I want the team to have an environment where they can continuously learn and feel safe and stable. When I see them get married, buy a house, have kids, and it’s all happened during their time at the company, I feel so unbelievably proud.”

Lil’s background is particularly untraditional for an entrepreneur. Raised in a low-income family in South Florida, several close family members passed during her childhood, including her father, when she was ten. She credits much of her enduring positivity today to her fourth-grade teacher. “It was a pivotal year for me. He would tell us stories in class that opened my eyes to the fact that life didn’t have to be the way I was living it and that all things are possible. It laid a foundation that has carried into my entrepreneurial journey; that although things may seem as they are, it doesn’t mean that they have to be as they are.”

Before Xendoo, Lil started her career as an engineer installing ATMs before becoming a sales representative for photocopiers and fax machines. She founded her first company, a systems integration business, in the early 1990s. Fast-forward to today, and she admits it’s still “extremely difficult” as a queer woman to raise money for a startup. In her typically unflappable nature, Lil’s outlook remains unwaveringly positive. “That just means that I have to run faster and jump higher. So, let’s go - let’s run faster and jump higher!”

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Presented with Pride Here is the first collection of one hundred incredible and inspiring LGBTQIA+ venture-backed entrepreneurs featured in this year's Gaingels 100.