Entrepreneur with ADHD used AI to stay on track. Now it’s a core part of his company.

Josh Driver, CEO of Indianapolis-based Selflessly, jokes that he’s practically in a common law marriage with his AI assistant, named Phil. (That’s short for “philanthropy,” which is Selflessly’s focus.) They’re a good match: Phil handles much of the administrative drudgery and helps clients figure out their philanthropic strategies so Driver can stay focused on big-picture strategy and client relations. But they get into the occasional tiff, and Phil can overstep his bounds. In fact, he recently went way off script with a client. Such an episode points up the risks in turning over so much responsibility to AI. But Driver sees Phil as an indispensable tool and interwove it into Selflessly’s recent from-the-ground-up platform rebuild. His interest in AI’s potential was piqued once he began using it to bypass some of the pitfalls of having attention-deficit/hyperactivity disorder. Recent episodes of the IBJ Podcast have focused on potential long-term risks of the widespread use of AI. In this week’s edition, we use Selflessly as a case study in how AI is being used by a small business right now. Driver also discusses his early career in emergency medicine — specifically, burn and wound care — and how that led him to technology and nonprofits.