Paul Epstein will take the stage at BSCAI’s 2026 Executive Management Conference to present “Winning Customers: Attracting and Retaining Fans for Life.”
His hot take? Monday isn’t a drag — it’s your best day to get ahead of the competition. We talked to the former NFL and NBA executive about how the habit of “winning Mondays” transforms performance and how leaders can connect purpose, culture, and ownership to drive success.
What motivated your transition from sports executive to leadership development?
I’ve always believed people, talent, and culture are a competitive advantage. Show me the quality of your people, and I’ll show you the quality of your business. In every high-performing organization I’ve worked with, success comes down to the quality of habits — championship habits.
The most important habit I witnessed in nearly 15 years in the NFL and NBA is what I call “Winning Monday.” It’s a weekly high‑performance reset.
Winning Monday leads to winning days, which stack into winning weeks, months, and ultimately your most successful year. It’s a habit any leader or team can apply in any industry.
What parallels exist between pro sports and contract cleaning organizations?
What works in sports works anywhere, because people drive performance in every field. When organizations prioritize talent development, create learning environments, empower people to take ownership, and allow their strengths to shine, results follow.
In sports and in contract cleaning, the hardest part is delivering results consistently. My recognition as a top thought leader who gets results stems from this same “Win Monday” principle. If you win your Monday, you set a momentum pattern for the entire week — 52 times a year. That’s how teams and businesses turn consistency into competitive advantage.
You’re known as the “Why Coach.” How can leaders reconnect with purpose and inspire their teams?
My life changed during a San Francisco 49ers leadership retreat focused on discovering your “why” — the core purpose at the center of your personal operating system. I started teaching it to my sales team, and soon coaches, players, and HR all wanted in. That’s how I became the “Why Coach.”
Think of your purpose as a compass:
- At the center is your why — the deeper reason you do what you do.
- Your values define who you are.
- Your beliefs shape what you stand for.
- Your decisions and actions reflect how you show up.
When a leader aligns how they show up with who they are and what they stand for, three things happen: authenticity, consistency, and confidence. And when leaders model purpose-driven behavior, teams feel it. Clients feel it. Culture strengthens.
Losses happen. How can leaders turn unfavorable circumstances into an advantage?
I call this playing offense in a defensive environment. Defense is everything that makes success harder — change, uncertainty, setbacks, adversity. Those conditions aren’t your fault, but you can choose to make them your responsibility.
Early in my career with the Los Angeles Clippers, we were ranked near the bottom of the league, and media labeled us the worst franchise in sports. Yet our sales team went from 28th to 2nd in the NBA by rallying around a simple idea: if we couldn’t sell results, we would sell hope.
Anytime you’re trying to get people to believe in a service, a vision, or a better tomorrow, you’re selling hope. Ownership, responsibility, and accountability win — especially when circumstances don’t.
And the best place to start building that ownership?
Start on Monday.