Lady Boss Podcast with Courtney Wright Courtney Wright

John Cerasani has carved a unique path in the business world, marked by bold decisions and remarkable success. His journey is not just a story of financial triumph but a testament to the power of perspective and the courage to challenge the status quo. At just 27 working in corporate America, John noticed a stark disparity between his contributions and his compensation. This moment of clarity propelled him to reevaluate his career trajectory and explore the realms of entrepreneurship.
And ever since then, John has redefined success on his own terms. He navigated the challenges of entrepreneurship with determination and strategic insight and today, is a source of inspiration and guidance for those looking to break free from the constraints of traditional employment.

Elizabeth Scott of Elizabeth Scott Design Group doesn’t just know design – she knows business, too. After creating her brand with custom home design, she started looking at ways she could branch out to build passive income. She combined her passion of design with a unique “rinse and repeat” model that is helping her business not just grow, but thrive.

Listen in to this mini-episode for takeaways on how you can find new opportunities within your business and why it’s so important to have multiple income streams.

Trish Thomas, a serial entrepreneur and 4x founder, is the Co-Founder and Chief Eating Officer of Whole & Free Foods. An early innovator, Trish founded and sold her first company four years after graduating from college. In the ‘90s, she built the first safe online community and a decade later had scaled transmedia entertainment properties to 100 countries in 65 languages. Trish has consulted on digital strategies for IBM, Dreamworks, Hasbro, Redbox, and Nissan to name a few. Trish pioneered a collegiate curriculm on how to improve the psychological resilience of founders as a means of improving start-up success rates. Currently, she is faculty teaching her entrepreneurship model at Northwestern University, and was the former Director of Entrepreneurship & Innovation at Lake Forest College. A food-loving, vibrant, connector of people, Trish is mom to six boys and is extraordinarily grateful when someone else makes dinner – especially if every body can eat it!

Nichole Wilson, is the Co-Founder and President of Whole & Free Foods. Nichole knows how to build, scale, and manage triple bottom line teams. Previously, she lead the R&D strategic planning process for PepsiCo’s $33B food portfolio, crafted Frito-Lay’s first Environmental Sustainability Strategy, pioneered alliances between M&A and R&D to create platforms to invest in smaller companies, like Sabra and Spitz, and managed the top tier brands Doritos and Fritos. She began her career in investment banking, and most recently led the $40MM investment portfolio for Chicago Beyond. A mother of two, Nichole’s family has experience with dietary restrictions that she believes should not define them. Determined and unafraid of what others call “impossible,” she uses her super powers to find unexpected solutions to big problems worth solving.


Every Body Eat® isn’t just a snack company, it’s a promise to create a world where everybody feels included.

On this episode we sit down with Dana (Rebecca) Gordon, third-generation jeweler who was born with diamonds in her DNA.

She was raised in the industry, often spending hours behind the scenes at her father's factory. During the summer of her sixteenth birthday, she travelled to India with her father and returned home with her first collection. To her shock and delight, it sold out in 48 hours. Each summer thereafter, she continued designing and selling her pieces. Soon, this hobby began to turn into a passion.

Dana did not initially set out to follow in her family's footsteps, but had her eyes set on law school. But in 2007, after graduating from the Gemological Institute of America in Carlsbad, California, she founded Dana Rebecca Designs. Wanting to create an accessible luxury fine jewelry brand, her business is built on the simple but important idea your jewelry should make you feel as comfortable as your favorite t-shirt and as amazing as your little black dress. Dana Rebecca Designs strives to create luxurious, everyday pieces women are excited to buy for themselves and gift to their loved ones.

Listen in as we hear about her journey in the family business, how she sets her company apart, and why it’s important to be open and honest with your community.

As a trusted leadership coach and consultant, today’s guest Amy Riley has worked with hundreds of leaders one-on-one, and thousands more as part of a group, to fully step into their leadership, create amazing teams and achieve extraordinary results.

Amy is also an internationally renowned speaker, author and consultant. Her new book, “The Courage of a Leader: How to Inspire, Engage and Get Extraordinary Results”, is a #1 international best-seller. With over 2 decades of experience developing leaders at all levels, we are excited to have her share about authenticity, clarity, and the courage it takes to develop your leadership legacy.

Katie May, mom of three and a small business owner, deftly balances motherhood with creating fashion collections from her home.

Her fashion journey began at 21 when she opened a clothing store in Madison, WI, where she honed her skills as a buyer, manager, and designer. After becoming a mother, Katie turned her creativity towards crafting clothes and pajama dresses for her daughters, which gained traction through her popular Instagram account.

This natural growth into the realm of social media influencing led to the establishment of her online shop, where she enlisted a team of skilled sewers. In 2021, the arrival of Emmaline, alongside sisters Windsor and Arabella, became the driving force behind the rebranding of her venture to EWAMAY. The brand now emphasizes high-quality, sophisticated pieces, specializing in matching mommy + me collections, as well as custom hat making and leather belts, showcasing Katie's dedication to family and design.

Listen in to hear Katie May’s entrepreneurial journey and how she’s handling the demands of fashion, influencing, and motherhood.