Alan has been a lawyer for more than 30 years. He was a senior associate at a large Bay Area law firm in the 90s, went in-house, then ran his own law practice, and has worked at companies including GitHub and Adobe and on contract with Apple. He is now Legal Counsel at OpenAI and the founder of DealDiligence.ai, an AI native law firm focused on due diligence for private equity and corporate development.

In this episode he talks to Photon Legal CEO Amit Koshal about what makes OpenAI different from every company he has worked at, the senior partner who threw his first draft back at him and why he is grateful for it, the year he was diagnosed with stage three stomach cancer while his wife was pregnant with twins and his first startup was going to market, why law firms were too slow to buy his legal tech product so he turned it into a law firm instead, and why "stay in your lane" is both the best and worst advice a lawyer can get. He also explains what entrepreneurship taught him that law school never did, and the one thing he says a GC's job is really about.

For the in-house lawyer who has wondered whether they could build something themselves, the founder who has pitched law firms and waited months for a decision, the young associate still waiting to be told what to do, and anyone who has been told it is too late to start, this conversation is for you.

Clarissa is Chief Legal Officer at Pindrop, whose technology analyzes more than a billion calls a year and has helped prevent over two billion dollars in fraud. By 35 she had been assistant counsel to the President in the White House, a partner in a large law firm and general counsel of her first tech company. She has taken a company public, studied ballet and worked as a choreographer in college, and now endows law school scholarships and a professorship in law and technology.

In this episode she talks to Photon Legal CEO Amit Koshal about the McGovern ruling and why the exemption she won is a higher bar rather than a loophole, the eight tough chapters of her career, why she runs three frontier models from three different labs on anything that matters and makes them argue, the blunt rule she gives her team of seven about AI, what she now sends to outside counsel and what she refuses to pay them for, and why she picks mission and people before title. She also explains the one lesson from the White House she still uses, and the story her father told her that she says is behind every unconventional call she has made since.

If you have ever been told by outside counsel that the law simply does not say that, a founder wondering whether your legal team is ready for AI, a junior lawyer afraid a machine just took your job, or anyone waiting for the storm to pass before getting on with life, this conversation is for you.

Olaseni spent twelve months in Afghanistan as a US Army JAG officer, serving as chief of detention operations across seven provinces in the east of the country. After the Army he went to Wall Street, then business school, then tech, as product counsel at Meta and at Intuit, where he worked on the AI agents inside Intuit's products. He came to the US at ten, has founded a company, and is now on an intentional pause to reflect and write.

In this episode he talks to Photon Legal CEO Amit Koshal about what a year of deciding who to hold and who to release taught him about operating in the gray, why the Army's bias for action stopped serving him once he left it, how AI has democratized information without making any of it more relevant to the facts in front of you, and why getting a product from zero to one in half the time can multiply the legal risk instead of halving it. He also explains why a rainy ride in a Waymo left him staring at the windshield wipers, and the one question he believes should sit in front of every product decision.

Whether you are a product counsel signing off on AI features, a GC whose business teams now arrive with their own AI research, a young lawyer wondering what you have that a model does not, or anyone who has run hard for a decade and never stopped to ask why, this conversation is for you.

Tom is General Counsel at Globality, where he became the company's first dedicated general counsel. Before that he spent about five years at a law firm practicing M&A, and he still does pro bono work. He is not a coder, but he has built his own AI agents for privacy, commercial, corporate and employment work, an intake system that tells colleagues when a contract does not need legal review, and a contract review setup where his playbooks produce the first pass of redlines.

In this episode he talks to Photon Legal CEO Amit Koshal about why great general counsels are business strategists who happen to know the law, the exodus from law firms between years three and five, how he set up each of his AI agents in three or four hours, why half of every contract review he does now goes into his playbook rather than the document, and what he asked outside counsel for when EU customers started sending him DORA addendums. He also gives a straight answer to a question he says people are reticent to answer out loud, and tells the story of the 36th straight hour on an M&A deal when he realized he did not want the life at the end of the path.

GCs running legal with a team they can count on one hand, law firm partners wondering why clients now expect the bill to come down, law students who have heard that AI does the first draft, and anyone who has looked down a hallway at the life they were working toward and wondered whether they wanted it: this conversation is for you.

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