Lessons From Three Decades of Deal Sourcing with Glenn Oken

In this episode, we sit down with Glenn Oken to trace how business development in private equity has evolved from 1989 to today, and what’s been lost (and gained) along the way.

Glenn reflects on the early days of deal sourcing, when private equity was barely an industry, competition was thin, and there were no CRMs, playbooks, or automated workflows to lean on. What existed instead was judgment, creativity, persistence, and a relentless focus on building real relationships — often face to face.

We explore how sourcing moved from hustle-driven relationship work to a more process-heavy function, why in-person connection still matters despite efficiency tradeoffs, and where experience beats financial engineering, especially in the lower middle market. Glenn also shares what it takes to survive the emotional reality of BD — the work that doesn’t bear fruit, the thrill of the hunt, and the long game of trust-building.