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Olaseni Bello has been a JAG officer in Afghanistan, a Wall Street lawyer, a founder and the lawyer behind Intuit's AI agents. Then he stopped, on purpose, to work out what the next season of his life is for.
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 Umberg runs the legal department at Globality with two lawyers. He says one good lawyer can now do the work of two or three, and the days of building a legal fiefdom are over.
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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http://www.youtube.com/@PhotonPodcast
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