Andrew Epstein, General Counsel at Demandbase, joins The Abstract to share his journey from Big Law to GC before the age of 35. In this wide-ranging episode, Andrew unpacks lessons learned from early bets in privacy, how he scaled legal operations with intention, and his forward-thinking approach to legal tech and AI. With candid stories from LiveRamp, tips for structuring lean teams, and reflections on mentorship and mindset, this episode is full of practical insights for legal leaders navigating change.

Key Insights:

1. Take the Nontraditional Path Early

Epstein’s first legal internship wasn’t at a firm or courthouse — it was with the Washington Nationals’ GC’s office, where he learned more about business than baseball. “Everyone else talked about their favorite player. I talked about impact,” he recalls. That mindset landed him his first big law offer later on.
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2. Don’t Be Just Another Associate

At O’Melveny, he deliberately joined the smaller, growing transactional group instead of the powerhouse litigation team. That gave him the chance to run deals early and collaborate across time zones — LA, London, and New York — learning speed, ownership, and how to build trust under pressure."
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3. Go In-House Before You Think You’re “Ready”

His pivot to LiveRamp under then-GC Vanessa Wu came just as privacy law was exploding. He left firm life right when his partners thought it was “a huge mistake.” It wasn’t. “I wanted to color outside the lines,” he says. The risk paid off — he ended up managing one of the most complex spinouts of the decade.
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4. Managing the Axiom–LiveRamp Split: “We Sold Our Parent”

Epstein helped navigate the unique sale where LiveRamp effectively sold its parent company, Axiom. He worked on building new systems from scratch — contract management, intercompany agreements, and team realignment. “We had to run as an independent business overnight,” he says. The team even got to ring the bell at the NYSE — a highlight moment in a grueling process.
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5. Scaling Legal at Demandbase: Build Lean, Hire Smart

When Epstein joined Demandbase in 2021, the company had two legal professionals and ambitions to go public. His first hires: a privacy lead and a legal ops head. “Without legal ops, I couldn’t have made the argument for headcount or automation,” he says. He focused on keeping the team lean, blending lawyers with contracts managers, and measuring performance through turnaround time and deal velocity.
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6. How He’s Using AI Today

Demandbase’s legal team automates all NDAs via CLM with AI. If the model detects risk, it routes to legal; if not, it auto-signs. “It requires me to say — I’m comfortable with that risk,” he says. His mantra: AI for leverage, not replacement. He even takes prompting courses to lead by example. “My team knows — every week, I’ll ask, ‘What did you do with AI this week?”.
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7. Build a Peer Group Before You Need One

From early mentors at O’Melveny to GC dinners and Slack groups, Epstein credits his network with accelerating his growth. “When I don’t know something, I ask. That’s the best investment I’ve made,” he says.
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8. Advice for Young Lawyers

“Get out of comparison culture. Don’t measure success by what others have. Measure it by what impact you want to make.”
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9. Closing Insight:

“AI won’t replace lawyers — but lawyers using AI will replace those who don’t.”

Epstein’s philosophy is simple: stay curious, stay human, and never stop iterating.

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