Decision Points E64 – From Pressure to Purpose: A Real Estate Legacy Rewritten with Bill Cawley
Decision Points13 Mai 2025

Decision Points E64 – From Pressure to Purpose: A Real Estate Legacy Rewritten with Bill Cawley

Bill Cawley’s life is a testament to the power of second chances. In this episode of Decision Points, the Chairman and CEO of Cawley Partners opens up about the trials, triumphs, and turning points that shaped his extraordinary path - from a small Midwestern town, through the depths of addiction, to the heights of commercial real estate success. Bill shares a deeply personal account of battling alcoholism, missing his shot at college, and becoming a father at age 18. With only $300 and a ster...

Episoder(89)

Decision Points E89 – Calvin Carter: Building the Future by Removing Friction: AI, Healthcare, and Human-Centered Innovation

Decision Points E89 – Calvin Carter: Building the Future by Removing Friction: AI, Healthcare, and Human-Centered Innovation

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 frictio...

21 Apr 1h 5min

Decision Points E88 – William Short: Strategic Innovation, Operational Discipline, and Building Durable Enterprises

Decision Points E88 – William Short: Strategic Innovation, Operational Discipline, and Building Durable Enterprises

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 f...

7 Apr 48min

Decision Points E87 – Derrick Evers: Detroit Resilience, Strategic Leadership, and Building for Long-Term Impact

Decision Points E87 – Derrick Evers: Detroit Resilience, Strategic Leadership, and Building for Long-Term Impact

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 Mil...

24 Mar 55min

Decision Points E86 – Bob Sambol: Heritage, Leadership, and Building an Enduring Hospitality Brand

Decision Points E86 – Bob Sambol: Heritage, Leadership, and Building an Enduring Hospitality Brand

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...

3 Mar 49min

Decision Points E85 – Mark Winters: Frameworks, Leadership Clarity, and the Discipline Behind Entrepreneurial Operating Systems

Decision Points E85 – Mark Winters: Frameworks, Leadership Clarity, and the Discipline Behind Entrepreneurial Operating Systems

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 developmen...

17 Feb 59min

Decision Points E84 – Adam Herrin: Strategic Risk, Market Cycles, and Building Platforms with Purpose

Decision Points E84 – Adam Herrin: Strategic Risk, Market Cycles, and Building Platforms with Purpose

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 Divisi...

3 Feb 52min

Decision Points E83 – Reimagining Rideshare: Will Coleman and the Creation of Alto

Decision Points E83 – Reimagining Rideshare: Will Coleman and the Creation of Alto

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, ...

16 Des 202540min

Decision Points E82 – Charting a Path to Mental Health Leadership: Dr. Jessica Gomez and the Future of the Momentous Institute

Decision Points E82 – Charting a Path to Mental Health Leadership: Dr. Jessica Gomez and the Future of the Momentous Institute

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, pe...

9 Des 202542min

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