Riley O'Brien

I advise founders, startups, venture capital funds, and strategic investors on how to build, scale, and exit with intention. My practice spans the full lifecycle of private companies—from incorporation and governance to financings, acquisitions, and everything in between. Having practiced in the US, Canada, and Bermuda, I bring a cross-border lens to structuring deals and navigating complexity. I work regularly with regulated investors (including financial institutions and BHCA-regulated entities), and I focus on sectors where innovation meets regulatory nuance: life sciences, biotech, fintech, software/SaaS, AI, and digital health. I also maintain an active pro bono practice, supporting nonprofit and mission-driven founders with structuring, governance, and early growth. If you're working at the intersection of technology, capital, and change—let’s talk. Attorney Advertising. Prior results do not guarantee a similar outcome.