When Slack launched an $80 million fund to invest in startups for its messaging service in late 2015, Awesome.ai was one of three firms that were the first to get funding. It was also the first to shut down.

The startup, which made a chatbot that lets teams share work updates through Slack, ran out of cash after eight months and couldn’t raise more. Van Miranda, the founder, said there were a lot of reasons for his failure, like the lack of a clear revenue model and his inexperience running a startup. But he said a large part of it had to do with the fact that investors were skeptical whether Slack’s users would pay for apps within the service.