Dionnie Wynter Pfunde’s Business Success Story

She was putting herself through college as a 16-year-old single mom. She was defying the odds. Then, in her first year of law school, Dionnie Wynter Pfunde was thrown a curveball: an unexpected second pregnancy.

“I decided I wasn’t going to stop. I literally went to final exams in the morning and gave birth that night. A week later, I was back in classes again,” she says.

Now the founder of Wynter Immigration Law, a Tampa-based law firm helping immigrants navigate the path to United States citizenship, Wynter Pfunde, born and raised in Jamaica, attributes her success to more than just hard work.

Resilience, grit, and asking for help were all factors. Here’s what she wants current and aspiring entrepreneurs to know about her story and how to thrive long-term.

Side Hustles: A Family Tradition

A mother and high school graduate at 16, Wynter Pfunde spent the next six years working various jobs in the Jamaican tourism industry while putting herself through college.

“I’m from a family that’s always had side hustles. From an early age, I saw that the best opportunities came from entrepreneurship,” she says. “Then, my dreams of being an entrepreneur were put on hold as I had to grow up quickly and support my firstborn.”

Odd jobs helped Wynter Pfunde take care of her daughter, and when money was tight she got financial help from her family. On one occasion, the aspiring lawyer’s mother pulled money out of her retirement account to help her daughter pay for college – a move considered by some to be a personal finance faux pas, but ultimately depends on the situation.

“She gave me everything she had. She always dug into her savings to make sure my tuition was paid. My mother is the hero of my story; if it weren’t for her, I wouldn’t be an entrepreneur today.”

To Get Your Roadmap for Success, Ask for It

Wynter Pfunde emigrated to the U.S. shortly before her 21st birthday with a big dream: she wanted to become a lawyer and have her own law practice. However, she wasn’t sure how to accomplish that goal or what next steps looked like.

“I didn’t know what it meant, I didn’t know about LSATs or bachelor’s degrees—I just knew I wanted to become a lawyer,” she recalls.  

Wynter Pfunde’s mother helped her get clarity by taking her directly to the lawyer who had previously helped with their family’s immigration. 

“I walked into his office in Manhattan, on some godawful high floor, with glass everywhere,” she says. “I was absolutely impressed with not only how nice his office was, but also with how he was treating my mom, an immigrant woman.”

“I told him I wanted to be a lawyer. He told me what it meant and how to become a lawyer in the best way he possibly could. I took that information, along with some information I’d gotten from my cousin, and created a step-by-step plan to accomplish my goal.” 

Remember to Ask for Support, Too

Wynter Pfunde notes that these requests aren’t just about gaining clarity; they’re also about asking for the support you really need to make everything work.

“Law school was a nightmare. I would drop my children off at the local library so that I could study,” she says. “My kids were at the library so much that the librarians knew them. Every spare moment was spent studying or watching my kids.” 

“To pay my bills, I signed up for every social assistance program available, sold furniture, worked at the prosecutor’s office, was a teaching assistant, and did anything and everything I could do.” Wynter Pfunde notes that her family’s propensity for side hustles taught her how to go out and drum up the money she needed to make ends meet.

To Scale Up, Charge the Value You Create

Even as an attorney, Wynter Pfunde notes that she wasn’t making real money in the early stages. 

“I wasn’t a savvy businesswoman. I wanted to help my community, so I let people pay what they could,” she says.

It wasn’t until 2015 that Wynter Pfunde made the tweak that would skyrocket her business results. Tired of being a bill collector due to low price points and payment plans – and feeling that she had done her part to help the community – she decided to raise her prices by 300%. 

Clients continued to sign on at these new rates, and the increase in revenue helped Wynter Pfunde hire contractors, engage service professionals, scale her business growth, and better serve her clients. She also joined several masterminds, such as Ladies Who Leverage, a mentoring accelerator for female entrepreneurs, which expanded her mindset.

“Being surrounded by professional women redefined what a true and successful businesswoman is for me,” she notes.

Today, Wynter Pfunde has one contract attorney, three paralegals, a legal assistant, a fractional CMO, and a P.R. person. She outsources her social media content posting. She also started Wynter Immigration Law Academy, an online training program for immigration lawyers to learn how to create a successful law practice. Systematizing her business has led to multiple six-figure months and corporate contracts. 

Each of the businesses has created financial independence for Wynter Pfunde and her family. She feels good that she could give back to her mother before she passed away and to the other family members that supported her. 

“Not everyone is going to choose you, and that’s okay,” she says. “Understand your value. I absolutely enjoy the freedom my business now gives me.”

Wynter Pfunde is living proof that staying focused on your dreams can help you overcome even the most challenging of obstacles. Her closing advice is short and straight to the point:

“Stay hungry, stay consistent.”