When venture capital investors shied from funding travel startups in the months after the pandemic hit last year, Elad Gil sensed an opportunity. The investor asked TripActions CEO Ariel Cohen if he could invest in his startup, which provides travel-related expense management software for businesses. The deal didn’t happen—Gil initially suggested a share price that was lower than what Cohen wanted, said a person familiar with discussions—but as the outlook for travel brightened late last year, Gil came back with a higher offer.

In January, Gil co-led a Series E round in TripActions that valued the Palo Alto, Calif.–based startup at $5 billion. He did so alongside VC firms Andreessen Horowitz and Addition, each of which manages funds worth billions of dollars. At the time, the size of Gil’s investment in TripActions, $40 million, was unprecedented for someone who operates as a solo venture capitalist, investing his own and other people’s money without other partners or support. But it was nothing compared to the head-turning investments Gil, 47, would make in the following months.