On this episode of Alignment for Impact, Matthew Naylor sits down with Crumdale Specialty founding partners Jake and Brian to reflect on the journey of building a company rooted in alignment, culture, and long term impact. They share their personal paths into entrepreneurship, from law and finance to insurance and healthcare, and how early relationships, curiosity, and a willingness to ask why shaped Crumdale’s operating philosophy.

The conversation explores how leadership, accountability, and trust became the foundation for a people first culture, including the now famous Crumdale Code and its emphasis on integrity and respect. Jake and Brian walk through how Crumdale approached innovation differently by integrating risk financing, healthcare services, cost containment, and technology into a single aligned platform. At its core, this episode is about building something meaningful by putting people first, embracing transparency, and proving that when alignment exists across the ecosystem, everyone can win together.

On this episode of Alignment for Impact, host Matthew Naylor sits down with Kelly Brady to explore what it really means to move from transactional insurance brokerage to true healthcare consulting. Kelly shares his path from Wisconsin into the employee benefits space, the mentors who shaped his approach, and how his role has evolved into one focused on partnership, education, and long term impact for employers and employees alike.

The conversation breaks down the unique dynamics of the Midwest healthcare market, the rise of level funded plans, and the challenges employers face when pharmacy costs spiral out of control. Kelly walks through a real client case where Crumdale Specialty helped intervene on high cost specialty drugs in a way that protected both the employer and the employee experience. At its core, this episode is about alignment, transparency, and empowering employers and employees to become better consumers of healthcare without fear or disruption.

On this episode of Alignment for Impact, host Matthew Naylor sits down with Jim Andrews to unpack a career shaped by grit, loyalty, and an athlete’s mindset. Jim traces his journey from growing up in Philadelphia to competing and coaching at the Division I level, then navigating a winding professional path that took him from coaching and hospitality into sales leadership at high-growth tech companies. Along the way, he reflects on lessons learned from mentors, failures that forced growth, and the discipline required to lead teams through uncertainty.

The conversation dives deep into Jim’s transition into healthcare entrepreneurship and the early days of building Crumdale Specialty from the ground up. He shares what it takes to create a people-first culture, why standards matter more than titles, and how trust, autonomy, and shared values can fuel rapid growth. At its core, this episode is about leadership, alignment, and building something meaningful without losing sight of family, character, and purpose.

In this episode of Aligned for Impact, Matt Naylor is joined by Angie Martinez of Dean and Draper to discuss her nearly three decade career in employee benefits and what it takes to advocate for employers in an increasingly complex healthcare system. Angie shares how her journey from personal lines insurance to employee benefits shaped her passion for client service, data driven decision making, and empathy for both employers and employees. The conversation explores rising healthcare costs, limited data transparency, vendor fatigue, and the importance of vetting solutions that truly improve outcomes rather than adding noise. Angie also reflects on leadership in account management, emphasizing steadiness, empathy, and clarity of purpose as essential traits for long term impact in the benefits space.

In this episode of Aligned for Impact, Matt Naylor sits down with Justin Burgess to explore how resilience, service, and transparency shape effective leadership in healthcare. Justin shares his journey from growing up in a family run restaurant business in New Orleans to becoming a leading voice in self insured employee benefits, including how experiences with Hurricane Katrina and the BP oil spill shaped his grit and servant leadership mindset. The conversation dives into fixing misalignment in healthcare through transparency, fiduciary responsibility, pharmacy cost containment, and human centered advocacy. Justin also reflects on entrepreneurship, culture, and the importance of doing hard things daily as a way to drive meaningful impact for employers and employees alike.

In this introductory episode, host Matthew Naylor explains that Aligned for Impact focuses on the idea that meaningful results happen when people, purpose, and performance are aligned. He shares how growing up with dyslexia, competing in athletics, working in a family business, and building a career in healthcare shaped his leadership philosophy and passion for improving a misaligned healthcare system. The show will feature entrepreneurs, brokers, and industry leaders working to create transparency, innovation, and better outcomes in both healthcare and business. Matt ultimately hopes listeners leave each episode with practical insights they can apply to create impact in their own lives and organizations.