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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode of Beyond the Case, Sohin Shah sits down with Ray & Monica Harrigill — founders of The Sunray Companies and fellow Harvard Business School OPM participants — for a conversation packed with hard-earned wisdom, mental models, and first-principles thinking.
From restaurants to salons, spas, hotels, and more, the Harrigills have built and scaled a multi-business portfolio grounded in integrity, disciplined risk-taking, and a shared belief that leadership is a “we, not I” journey. We talk through the frameworks that guide their decisions, how OPM (including insights from Linda Applegate) sharpened their strategic focus, and why sometimes the most important step in entrepreneurship is simply taking the shot.
This is a story about building as partners, thinking long-term, approaching risk thoughtfully, and developing people so the whole organization can rise. As Ray says, entrepreneurs need both the hope to believe a better future is possible and the discipline to make principled decisions while building it.
Here are the Top 10 Takeaways from the conversation:
- “Take the Shot” — Hope Is a Strategy
Entrepreneurs act before certainty. Linda Applegate’s framework resonated: narrow the field, find the opening, and take the shot — even with shaky legs. - First Principles: People + Process
Their model: People build businesses. Processes sustain them. Leaders step out of operations so scale can happen. - Ray’s Shoe Philosophy
His dad said: “When you put your shoes on, decide if you work for yourself or someone else.” Early seeds of ownership and agency. - Integrity Is Non-Negotiable
If a leader bends 5%, the team bends 15%. The rule: don’t bend — ever. - Their Relationship Is the Operating System
Monica leads people and culture; Ray leads growth and finance. Clear lanes create alignment without ego. - Instinct + Analysis
Gut drives speed; analysis drives safety. Their decision-making blends both. - Debt as a Tool
Ray jokes: “I bathe with debt.” Their view: use debt, don’t fear it, and manage downside risk intentionally. - “I → We” Is the Leadership Upgrade
Monica’s lesson: leadership becomes real when you stop saying “I” and start saying “We.” - Teach Kids to Build, Not Receive
“A gift isn’t sustainable.” Their children are taught to work, grow, and sustain themselves. - Constant Learning Wins
Their reading list: Think and Grow Rich, Extreme Ownership, Scaling Up, and Who. Books matter not just for information — but for timing.
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