105: From AOL Lawyer to Purpose-Driven Deal Maker with Jan D'Alessandro.

Stuck - Expert Career Advice with Rob and Jamal

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Episode Overview

Meet Jan DAlessandro, who pioneered remote work at AOL in the 90s and now directs billions in corporate philanthropy at Pledge One Percent. Her story shows how lawyers can leverage their skills far beyond traditional practice into business development and social impact.

Key Topics

• How Jan invented working from home at AOL in the 1990s
• Transitioning from corporate law to business development
• Building win-win partnerships across tech, media and entertainment
• Creating sustainable corporate giving programs
• Navigating career transitions in times of uncertainty

Key Quotes

"I got to a point where I thought, I don't really care about the indemnity clause. And then I realized - you can't do this job anymore because somebody needs to care about that. And it wasn't me."

"Culture eats strategy for breakfast every day."

"As a lawyer, you're trained to think critically... to not take things at face value and see how you can turn it into something positive for both sides."

Practical Insights

• Use your legal training as a foundation for other roles:
  • Critical thinking
  • Negotiation skills
  • Deal structuring
  • Understanding multiple stakeholders
• Look for opportunities to merge your professional skills with personal interests
• Consider how your expertise could apply to emerging fields like AI
• Focus on building win-win partnerships rather than just transactions
• Stay connected to what energizes you, even if it means changing roles

Key Lessons for Career Transitions

1. Be honest with yourself about what naturally energizes you
2. Look at what you spend your free time doing - there are jobs related to any interest
3. Focus on transferable skills rather than just industry experience
4. Don't underestimate the value of your professional training in new contexts
5. Consider how emerging technologies like AI create new opportunities in familiar industries

Guest Bio

Jan DAlessandro pioneered work-from-home practices at AOL in the 1990s before transitioning into business development roles at major tech companies. As head of Pledge One Percent's Equity Initiative, she's helped direct over $2.5 billion in corporate philanthropy. Her career spans law, tech, entertainment and social impact.

Resource Mentioned

• Marianne Williamson quote: "Playing small doesn't serve the world"
• Cheryl Sandberg's gratitude journaling practice
• The Innovator's Dilemma by Clayton Christensen

About Stuck

Subscribe to Stuck on Apple Podcasts, Spotify, or wherever you get your podcasts. Email us at [e-mail]. Produced by Rob Curtis, Jamal Stockton, and Ximena de la Tijera.

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This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera