Digging for Smiles & Digging Out of Crisis: Ryan Schmitt’s Story of Resilience

In this episode of the Legacy Builders Podcast, Kyle sits down with Ryan Schmitt, Founder & CEO of Petticoat Schmidt, to unpack the extraordinary journey behind one of Florida’s fastest-growing heavy civil construction companies. Ryan shares the origin of the business, the early leap of faith, and the brutal season he calls “The Valley of Darkness,” where stacked job losses, financial collapse, and overwhelming pressure nearly took everything he built. Through transparency, grit, and the support of his wife, mentors, and team, Ryan walked “into the punch” every day—emerging with a renewed vision for leadership, culture, and purpose. His mindset, accountability systems, and commitment to open-book management helped transform a struggling company into one defined by resilience and unity.Ryan also reveals why he chose to sell 30% of the company to his employees through an ESOP, creating shared ownership and long-term wealth for the people who helped rebuild the business from the ground up. He discusses the spiritual and personal rhythms that anchor him, the importance of faith and family in leadership, and the habits that keep him performing at his highest level. This conversation highlights what it truly means to lead with humility, build a culture where people matter, and create a legacy that outlives you.Stay connected to the conversation by joining us on your favorite social media platform! https://linktr.ee/legacybuilderskm