In this episode of Founders Future, host Elliott Boll sits down with Caroline Woosenfranzia’ the founder of Uppercut First, to explore her entrepreneurial journey and vision for the future.
Caroline shares her motivation for leaving the corporate world—where office politics often overshadowed execution—and how she built a thriving consulting business focused on performance, impact, and results. She also reveals a major milestone: Uppercut First is celebrating its fifth anniversary, and she is launching a new venture—an eco-friendly offsite and event space in Lisbon, designed to help companies reset, strategize, and improve collaboration in a unique environment.
The conversation touches on key trends in leadership, including the increasing mobility of executives across companies, as well as the challenges of scaling a business. Caroline highlights how her sales expertise made the transition to entrepreneurship smoother but notes that packaging her knowledge into a structured offer was one of her biggest early hurdles.
She also shares insights into innovative approaches to company offsites, particularly how neurodiverse individuals process information differently. She describes how her new business will create engaging, digestible learning experiences using storytelling, gamification, and hands-on metaphors to improve retention and collaboration among teams.
As the episode wraps up, Caroline leaves founders with a thought-provoking challenge: How much do you really know about your company’s data, and how accurate is it?