Growing up in an entrepreneurial family, Vlada Lotkina, CEO and co-founder of ClassTag, saw firsthand the successes and failures that come with pursuing your dreams. It was that inherited pioneering spirit that drove Vlada to emigrate from Ukraine to attend the University of Pennsylvania’s prestigious Wharton School for her MBA.

Vlada had a few different business ideas but it wasn’t until her daughter began preschool that she fully dove into entrepreneurship. In fact, it was the overwhelming experience of teacher-parent communications that inspired Vlada to create ClassTag, a platform focused on better connecting parents with their students’ teachers.

On this episode of Defining Moments, Vlada explains how she transformed a common obstacle into an app that now benefits more than 25,000 schools and 4 million families.

When Gail Sexton Anderson began working in third-party fertility nearly 25 years ago, she dreamed of opening a one-stop-shop that would give prospective parents all the resources to face the challenges ahead. Whether it’s mental, emotional or educational support, Gail is determined to provide it to her clients.

On this episode of Defining Moments, Gail shares about her personal journey through motherhood and how it led her to open an empathy-driven center where women, men, and intended parents can seek the help and agency they need to start a family.

Lendio's CEO, Brock Blake, gives an update on this new round of Paycheck Protection Program (PPP).

The latest round of PPP comes with bolstered support for the businesses that need it most, including: the ability to receive a 2nd PPP loan for borrowers who previously received a loan, funding specifically earmarked for performance venues and BIPOC-owned businesses, provisions to help ensure that the smallest businesses can secure these essential loans, and better support for hard-hit industries like restaurants.

It took quitting a corporate job and living in Morocco for a year for Sam Frank, co-founder of and partner at Four Twelve Roofing, to realize that his heart belonged in the city he’d grown up in.

Sam was inspired by the incredible design projects and architecture he saw in Morocco and wanted to bring that kind of beauty to Baltimore. There was just one problem: He didn’t have any experience in construction.

On this episode of Defining Moments, Sam explains how a beer and an insulation project introduced him to his co-founder Shea Frederick, what makes a sexy roof and why he’s in no rush to abandon Baltimore for larger cities.

Natural ability is a useful starting point, but the trait that will push you over the finish line is grit. Navy SEAL veteran and Madefor co-founder Pat Dossett admits that he isn’t the best at anything, but he is extraordinarily resilient.

After studying hard to get into the Naval Academy, Pat earned a highly competitive place in SEAL school. When his military career ended, he embarked on another challenging path: entrepreneurship.

On this episode of Defining Moments, Pat explains how Madefor aims to change lives, the SEAL skills that translated to business — no, demolition isn’t one of them — and why long-lasting change starts with small steps.

Sometimes being green means charging ahead even when everyone else is applying the brakes. Robin Chase is a serial transportation entrepreneur, but she had no idea what she was getting into with her first project — and that’s how she pushed the market forward.

Robin is the co-founder and former CEO of Zipcar, the car sharing service that connects members to available cars nearby, which they can use for an hourly or daily fee. It’s a recognizable model today, but being first came with unseen obstacles.

On this episode of Defining Moments, Robin explains why honesty is the best customer service policy, why she’s worried about new shared-transport companies, and how ditching cars for bikes can set us free.

In March 2020, Jesse Jacobs had big plans for growth. He had founded Samovar Tea, an organic small-batch tea company, nearly 20 years ago, and he was ready to expand from his four retail locations.

Of course, the state of the world quickly shifted. For Jesse, the challenges of 2020 led to redefining growth and finding opportunities outside the walls of his tea cafes and lounges.

On this episode of Defining Moments, Jesse explains how he’s managed to shift his business online, allowing him to reach more people and teach them the benefits of tea and mindfulness. He also shares how meditation has helped him through his journey — which, you’ll learn, has included quite a few obstacles.

Lawyers get a thrill from a fight. And Noam Cohen and Hannah Genton, founding partners of transactional law firm CGL, are taking on a major opponent: cultural expectations that lawyers must burn themselves out in exchange for high salaries and big bonuses.

CGL is a distributed law firm, meaning that its attorneys work wherever they want and on their own schedules. As long as they give clients exceptional service, they’re in charge of their own hours and where they spend them.

In this episode of Defining Moments, Noam and Hannah explain why so many lawyers burn out under the traditional “BigLaw” model, how shunning a centralized office empowers them to offer competitive rates and why happy attorneys have better relationships with their clients.

Leaving the beaten path and forging your own can lead to success — but not without obstacles. Liz Mumford, co-owner of creative agency Mabble Media, is still charting the best course.

One thing Liz believes in firmly is giving her staff a work-life balance that can help foster their creativity at work. After all, it’s the drive to be different and imaginative that sets Mabble apart.

On this episode of Defining Moments, Liz talks about keeping her staff in a creative state of mind, helping the wider community through the pandemic, and playing catch-up to businesses that took a different approach to handling the COVID crisis.

Improv training teaches you to deal with the unknown. But Lillie Frances, owner of Chicago Comedy Company and Laugh Out Loud theaters, says nothing could have prepared her for 2020.

“You would think that as an improviser, I'd be better at this stuff, but I hate ambiguity. I hate not knowing when everything's going to end and we're going to be back up and running in full swing,” she says.

On this episode of Defining Moments, Lillie talks about incorporating mask-wearing into an improv play, looking out for her staff and working on diversity, and attempting guilt-free relaxation as a small business owner.