For Calvin Carter, technology has never been the starting point. People are.

In this episode of Decision Points, Calvin Carter, Founder and CEO of Matic, shares a career defined by identifying friction and building systems to remove it. From the earliest days of the internet to the rise of mobile and now artificial intelligence, Calvin has consistently operated at the edge of major technological shifts. His work focuses on translating emerging capabilities into real-world outcomes.

He reflects on his early exposure to entrepreneurship, his instinct to recognize where technology is heading, and the belief that has guided his work from the beginning. Start with human problems, not technical possibilities. That approach shaped his path from building early web experiences for major brands to founding Bottle Rocket, where his team helped define the modern mobile ecosystem for companies like Chick-fil-A, Southwest Airlines, and NPR.

With Matic, Calvin is applying that same discipline to healthcare. He explains why many AI efforts fail. They begin with the technology instead of the user. Matic takes the opposite approach. The company studies the daily experiences of doctors, patients, and administrators, then embeds intelligence directly into those workflows. The goal is simple. Reduce friction, improve care, and return time to the people inside the system.

Calvin also shares his perspective on leadership. He emphasizes culture, empathy, and surrounding yourself with people who are motivated to serve others. He outlines a framework built on passion, persistence, and conviction. His view is direct. Long-term success is not defined only by outcomes. It is defined by how those outcomes are achieved.

This conversation offers a clear view into building at the edge of innovation while staying grounded in human impact. For investors, operators, and business leaders, it reinforces a simple principle. The most valuable systems are built by understanding where the system is broken.

William Short built his career through a combination of disciplined thinking, curiosity, and a consistent willingness to pursue improvement in complex systems. His path reflects a steady progression from early entrepreneurial projects to leadership roles in healthcare services, financial products, and large-scale benefits administration. Today he serves as Executive Chairman/CEO of AmeriFlex, one of the largest independently owned providers in its sector.

In this episode of Decision Points, Scott Wood sits down with William to walk through the decisions that shaped his approach to business, leadership, and long-term growth. William discusses his early years in Kansas City and the formative ventures that introduced him to technology, process design, and customer behavior. He explains how those experiences influenced his thinking as he entered the workforce and began identifying areas where financial products and health-related services could be improved.

The conversation explores William’s time at UMB Bank, where he identified an underutilized medical savings program and developed a white paper that helped leadership recognize a broader opportunity. That initiative contributed to the creation of UMB Healthcare Services. William describes the lessons learned in product design, regulatory navigation, and building trust in an emerging market category.

William outlines the transition to AmeriFlex, describing how he approached evaluating the business, restructuring operations, and positioning the organization for scalable growth. He also shares the rationale behind relocating to Texas, the expansion into Workforce Go, and the internal disciplines required to manage multiple ventures. Throughout the discussion, William highlights the importance of balancing mind, body, and soul, and how writing two books as a dyslexic author helped refine his communication and thought processes.

His insights offer valuable perspective for founders, operators, and investors seeking clarity around innovation, organizational discipline, and the long-term development of complex service platforms.

When you are responsible for reshaping a skyline, vision is not optional. Derrick Evers carries that expectation with a steady confidence shaped by his early years in Detroit. Growing up off Seven Mile taught him how to recognize real challenges and how to keep moving when the circumstances were difficult. Those lessons continue to influence his leadership today.

In this episode of Decision Points, Scott Wood sits down with Derrick Evers, Co-Founder, Managing Partner, and CEO of Kaizen Development Partners, for a detailed discussion of the decisions and relationships that shaped his career. Derrick describes his upbringing, the influence of his parents, and the transition from Detroit to Texas A&M, where he began to recognize the value of disciplined preparation and mentorship. He explains how these foundations helped guide his early steps into commercial real estate.

The conversation explores Derrick’s progression from general contracting into important roles at Trammell Crow Company and Staubach. Each stage introduced new expectations and expanded his understanding of leadership, strategy, and organizational growth. Derrick speaks candidly about his experience with the Neil Richards Group, the strain of building a business within someone else’s structure, and the cost of staying aligned with personal and professional values.

Derrick describes how these experiences led to the creation of Kaizen Development Partners. He explains why the principle of continuous improvement forms the basis of the company’s identity and how that philosophy has informed both team selection and project strategy. Today, Kaizen is engaged in several major initiatives, including the new Dallas Convention Center and Chalk Hill, a 130-acre mixed-use development designed to create long-term community impact.

Throughout the episode, Derrick reflects on the principles that guide his decision-making. He speaks about the influence of faith and family, the importance of disciplined leadership, and the responsibility to pursue growth with intention. His insights offer a clear and grounded perspective for investors, operators, and leaders navigating complex environments.

Bob Sambol grew up inside the hospitality world. His father owned restaurants and bars in Manhattan, and Bob spent much of his childhood in those rooms learning how people work and how service creates value. Those early experiences shaped a leadership style grounded in work ethic, consistency, and a clear understanding of what it means to build trust in a customer-driven business.

In this episode of Decision Points, Scott Wood sits down with Bob Sambol, founder of Bob’s Steak & Chop House, for a detailed look at the strategic decisions behind one of Dallas’s most recognizable restaurant brands. Bob discusses his upbringing in the Bronx, the influence of his family’s work ethic, and the early exposure that introduced him to the pace and responsibility of hospitality. He also describes the decision to leave for Miami at twenty-three, the rapid progression that followed, and the lessons learned managing operations at a young age.

The conversation examines the founding of Bob’s Steak & Chop House in 1993, the financial pressure of the early years, and the relationships that sustained the restaurant during its most challenging periods. Bob explains how a strong focus on product quality, service consistency, and disciplined management contributed to long-term brand strength. He also describes the pivotal moment when national attention, driven in part by influential customers, shifted the trajectory of the business.

Throughout the episode, Bob reflects on the principles that guide him as a founder and operator. He discusses loyalty, accountability, and the long runway required to build a brand that lasts. For leaders, investors, and operators, his experience offers a clear view of how disciplined execution and consistent values form the foundation of enduring businesses in competitive industries.

Mark Winters built his career at the intersection of leadership, structure, and strategic decision-making. His work spans engineering, Fortune 50 environments, early-stage ventures, and the development of frameworks that are now used by leadership teams across the country.

In this episode of Decision Points, Scott Wood sits down with Mark Winters, entrepreneur, co-author of Rocket Fuel, and a leading EOS Implementer. They examine the experiences that shaped his approach to organizational performance. Mark discusses his early life in Poteau, Oklahoma, the academic shift that moved him from engineering to business, and the time he spent at Procter and Gamble, where he learned important lessons about accountability and operational discipline.

The conversation follows Mark’s early entrepreneurial ventures, including the launch of a cyber café concept, the challenges of capital structure and investor alignment, and the lessons learned inside organizations such as Amoco and a Los Alamos startup. He explains how these experiences informed his thinking on leadership behavior, decision-making, and the realities of building and scaling companies.

Mark reflects on the development of the Visionary and Integrator model, the role of EOS in supporting organizational clarity, and how leadership chemistry influences long-term success. He also previews his upcoming book, Visionary, which encourages leaders to confront blind spots and strengthen their impact over time. His insights offer founders, executives, and investors a clear look into the frameworks that support sustainable organizational growth.

Real estate markets reward those who understand cycles, manage risk, and recognize when to create their own path. Adam Herrin has built his career at those intersections. From Celina, Texas, to Division I football at Rice University, to the deal rooms of HFF during the Great Financial Crisis, his trajectory reflects disciplined thinking, strategic repositioning, and a willingness to act when others hesitate.

In this episode of Decision Points, Scott Wood sits down with Adam Herrin, Founder and Managing Partner of Formation Interest, to examine the decisions and inflection points that shaped his development as an operator and investor. Adam discusses the early discipline that competitive athletics instilled, the lessons learned working through the 2008–2009 downturn, and how visibility into distressed capital markets sharpened his understanding of risk, timing, and execution.

Adam details his progression from analyst to producer at HFF, the launch of an industrial capital markets team, and the strategic rationale behind co-founding Urban Logistics Realty. He reflects on the complexities introduced by the pandemic, how shifting visions required a reset, and why choosing to start again offered the clarity needed to build Formation Interest with intention. He also addresses the core principles that guide his approach to leadership, team construction, and sustainable business practice.

The conversation offers a clear view into how Adam evaluates opportunities, balances quality of life with professional ambition, and thinks about long-term value creation in competitive real estate sectors. His experience provides investors and founders alike with practical insight into market cycles, strategic differentiation, and the discipline required to build platforms that last.

For Will Coleman, frustration with ride-hailing turned into a vision for something better. As co-founder and CEO of Alto, he set out to create a new kind of mobility company—one built on consistency, safety, and hospitality.

In this episode of Decision Points, Will shares how a decade at McKinsey prepared him for the leap into entrepreneurship, and how a dinner-table conversation with his wife sparked the idea for Alto. Launched in 2018, Alto took a radically different path than its competitors: a vertically integrated model where drivers are employees, vehicles are company-owned, and every ride is designed to deliver the same trusted experience.

Will opens up about the turbulence of building a company in a volatile industry. When COVID-19 hit, Alto saw revenues fall 96% overnight. Instead of folding, they doubled down on their strengths—cleanliness, safety, and service—emerging stronger with expansions into Houston, Los Angeles, and beyond. Strategic partnerships, including a recent deal with Uber, further demonstrate Alto’s ability to adapt and scale.

Looking ahead, Will shares his vision for the autonomous future. With infrastructure already in place, Alto is positioning itself to integrate self-driving technology seamlessly into its service—bridging human-driven and autonomous rides under one consistent brand. More than just a tech story, Alto is also an employer story: offering benefits, stability, and culture in a gig economy defined by uncertainty.

For Dr. Jessica Gomez, leadership begins with empathy. From the south side of Chicago to the helm of one of Dallas’s most respected mental health organizations, her story is a testament to purpose, perseverance, and the power of community.

In this episode of Decision Points, Scott Wood sits down with Dr. Jessica Gomez, Executive Director of the Momentous Institute, to explore her journey from aspiring physician to nationally recognized psychologist and nonprofit leader. Jessica shares how formative experiences growing up in Chicago shaped her drive to help children and families, and how that calling led her to the Momentous Institute—a century-old organization at the forefront of mental health, education, and community impact. She discusses the decision to pivot from medicine to psychology, her early years serving through the Salesmanship Club, and her evolution from practitioner to executive.

The conversation dives into leading through the pandemic, implementing the Entrepreneurial Operating System (EOS) to strengthen organizational clarity, and scaling the Institute’s programs nationwide—from the Momentous School to their groundbreaking Change Maker curriculum. With a goal of impacting one million lives by 2031, Jessica shares a vision that extends beyond traditional therapy, reaching into workplaces, schools, and communities across the country. Her message is clear: investing in mental health isn’t just a social good—it’s a foundation for stronger, more resilient organizations and lives.