In this episode, host Olga Mack sits down with Jessica Nguyen and Nada Alnajafi for an honest and energizing conversation about what happens when in-house lawyers build beyond their day jobs, and how personal brands, communities, and bold decisions create real leverage.

Nada Alnajafi is Senior Corporate Counsel and Lead Legal Ops at Franklin Templeton and the founder of Contract Nerds, a community she built from a passion project into a thriving business later acquired by DocuSign.Jessica Nguyen is Deputy General Counsel at DocuSign and Head of Contract Nerds, with a track record of building legal teams and scaling legal technology companies from early-stage startups to successful exits.

Key insights from this episode:

• How side hustles can evolve into strategic business assets

• Why email lists and community ownership matter more than social followers

• How to evaluate risk as an in-house lawyer• What founders should consider before selling their business

• The emotional realities of acquisitions, and how to navigate them

• Why lawyers must rethink risk aversion and embrace upside

This episode is for in-house lawyers, founders, legal operators, and anyone wondering whether they can build something meaningful beyond their role without walking away from it.

Takeaways:

• Build with generosity first, monetization follows value

• Strategic partnerships matter more than short-term offers

• Preparation and organization accelerate opportunity

• Lawyers are uniquely equipped to build, if they embrace the upside.

• Alignment beats adrenaline in both business and life.

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