Ross Darwin came to fintech investing at Portage after years spent in education—first doing education consulting with publishers, school districts, and universities, then investing in edtech and future-of-work at Owl Ventures, where he tracked how education overlapped with financial literacy and wellness. That history shows up in how he evaluates founders today: he looks for proof that a product actually improves outcomes and for a credible plan to sell into complex, multi-stakeholder environments, rather than just being drawn to an exciting idea.