Last fall, executives at Pinterest were inching toward an agreement to acquire Verishop, an online shopping platform that Pinterest had been negotiating with for at least two months, according to two people familiar with the situation. The deal could have helped the internet scrapbooking service accelerate its belated commerce efforts.

But the talks hit a wall as Pinterest’s CEO, Ben Silbermann, delayed making a decision on terms for a deal, frustrating Imran Khan, the former Snap executive who led Verishop, and Khan’s team, the people said. Silbermann may have had something else on his mind. Days after the Verishop talks stalled, news broke that PayPal was in talks to acquire Pinterest for $45 billion, conversations the Pinterest deal makers in charge of the Verishop talks weren’t aware of, the people said.

A few days later, after the PayPal and Pinterest talks collapsed, Silbermann was ready to make a deal for Verishop. Pinterest made a $500 million stock and cash offer to Khan for the company, according to one of the people. But it was too late. Silbermann’s handling of the discussions, including the plodding pace of the process, had soured Khan on the deal, the people said.