This episode is recorded live, and is best enjoyed on YouTube. Watch the episode here.
While Bob is visiting San Francisco for two weeks, he is sitting down for conversations with legal tech innovators and entrepreneurs "in their natural habitats" – places in the Bay Area they consider special. Today, in the first in this series, Bob sits down for lunch with Alex Su, chief revenue officer at Latitude Legal, over Thai iced tea and tofu dishes at Phnom Penh House, a Cambodian restaurant in Alameda that Alex considers something of a personal institution, frequenting it for both family meals and business meetings.
Alex's career path is anything but linear. He started as an associate at Sullivan & Cromwell in New York, clerked for a federal judge in Chicago, then drifted through a plaintiff's firm, a brief solo practice, and ultimately a leap of faith into legal tech sales – joining e-discovery company Logikcull in 2016. From there, he moved to Everlaw, then to Ironclad, where he served as head of community development, building a reputation that spread well beyond any job title.
That reputation was shaped in large part by TikTok, where Alex's comedic, self-effacing videos skewering law firm culture – partners, associates, privilege logs and the absurdities of BigLaw – earned him more than 100,000 followers, got shared inside Ironclad's internal Slack, and ultimately helped land him his next job. It's a story of accidental virality and deliberate reinvention that mirrors the broader shifts he sees in the legal profession.
Now at Latitude Legal, an ALSP providing on-demand legal talent to law firms and corporate legal departments, Alex represents a kind of poetic symmetry: a lawyer known for championing "alternative careers" working at an "alternative legal services provider" — a label he thinks has outlived its usefulness, given how mainstream flexible legal talent has become.
Bob and Alex also dig into the current state of legal AI – what's overhyped, what's underhyped, and why the pandemic was arguably a bigger inflection point for legal tech adoption than generative AI. Plus, Alex and Bob reflect on Bob's three decades of covering legal innovation, the stubborn persistence of the billable hour, and why the justice gap remains stubbornly wide despite all the talk of disruption.
It is a wide-ranging and candid conversation – one you may want to watch on video instead of just listening to the audio.
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Chapters
00:00 Intro to Today's Lunch: A Special In-Person Series
04:45 Career Transitions: From Law to Legal Tech
23:27 Going Viral: The TikTok Journey
25:10 Balancing Humor and Professional Identity
26:54 Redefining Career Paths for Lawyers
28:39 The Evolution of Legal Careers
30:35 Innovation in Legal Practice
34:07 The Impact of the Pandemic on Legal Technology
34:28 The Future of Legal Technology and AI
38:10 Navigating Uncertainty in Legal Services
40:18 The Ongoing Relevance of Traditional Legal Models
42:11 Personal Reflections and Future Outlook
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