Key Insights
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1. Uncomfortable Risk Creates Outsized Experience.
At FanDuel, facing potential shutdown by the NY Attorney General and a failed merger with DraftKings, Sanjay deliberately chose to stay. He reasoned that even if the company failed, the crisis management experience was invaluable and offered more professional growth than years at a firm. Lawyers must be willing to lean into the uncertainty of being a legal executive in a highly regulated, yet gray, area.
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2. Legal Must Drive Strategy in Regulated Industries.
In industries like sports betting and crypto, the legal department is not just an advisory or sign-off function. Legal strategy fundamentally drives the business, dictating promotions, commercials, partnerships, and market entry. This context allowed Sanjay to be more than "just a lawyer" but a business-savvy executive.
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3. Networking is Relationship Capital, Not Transactional.
Sanjay achieved the coveted in-house sports role not through blind applications, but by deliberately building genuine relationships with people he respected, without expecting anything transactional in return. This "relationship capital" later became his primary source of deal flow for advising and investing.
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4. Incentives Must Be Aligned Via Equity.
Traditional endorsement deals paid large, fixed fees, which created a "bare minimum" relationship where the athlete's incentive ended upon payment. Equity deals (rev share or stake) align the interests of the brand and the athlete, often leading to massive outsized returns for the athlete (e.g., Jordan and Nike) and requiring greater effort from them for the shared outcome.
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5. To Advise, Just Start
Lawyers should transition into advising by simply offering their help for free or on a success-fee basis to people in their network who are building things. The experience gained from scaling and launching businesses—and the mistakes learned—is what makes the advice valuable

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6. Closing Insight

Your professional comfort zone is where learning stops. Leverage your current role to take calculated risks that promise exponential experience, enabling you to eventually trade the stability of a title for the flexibility and control of an entrepreneurial career.