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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In this episode of Notes to My (Legal) Self®, host Olga V. Mack speaks with Heath Morgan, in-house attorney and author of The Memory Project, about memory, identity, and the long-term ethical implications of AI adoption.

Drawing from his experience in cybersecurity, compliance, and AI governance, as well as his speculative fiction work. Heath explores what happens when technology allows us to preserve, replicate, and even converse with digital versions of ourselves.

Together, they explore:

• Why AI forces us to confront legacy in ways social media never did• The concept of “conversational time travel” and digital personas of the past and future

• How companies may face a two-market reality: privacy as default vs. privacy as luxury

• The hidden risks of unintentional AI adoption inside organizations

• Why in-house counsel must move from reactive policy drafting to intentional AI governance

If you’re an in-house lawyer navigating AI implementation or questioning how emerging technologies will reshape privacy, identity, and ethics, this conversation challenges you to think several steps ahead.

Explore more episodes, insights, and reflections at:

www.notestomylegalself.com

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In this episode of Notes to My (Legal) Self®, host Olga V. Mack speaks with Rina Wang, former Assistant General Counsel at AI startup Prepared, about what it really means for lawyers to build a career inside venture-backed startups, especially during periods of uncertainty, hypergrowth, and rapid change.

Drawing from her journey across litigation, multiple venture-backed startups, and a recent acquisition by Axon, Reena offers a candid perspective on what lawyers should expect when they step into startup life.

Together, they explore:

• Why uncertainty isn’t a flaw of startups; it’s a defining feature

• How one year in a startup can feel like 10 years in a Fortune 500 company

• What it means to make career decisions with limited information

• How lawyers can shift from risk-avoidance to value creation in fast-moving environments

• Why startups force accelerated learning, leadership, and personal growth

If you’re a lawyer considering a move into a startup or questioning whether speed, ambiguity, and change are worth the tradeoff, this conversation offers an honest look at the realities behind the hype.

Explore more episodes, insights, and reflections at:

🌐 www.notestomylegalself.com

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