During the spring and summer of 2018, I negotiated a possible acquihire of Checkly/moi with Datadog. The process began when a representative from Datadog emailed me to inquire about Checkly and potential integration benefits for both customers. We discussed the possibility of integrating dev accounts, testing, and marketplace features. This initial contact was likely a reconnaissance mission, as I later received a follow-up message indicating a closer partnership between Checkly and Datadog. The meetings progressed with multiple Zoom calls, in-person discussions, and coffee breaks, where we discussed various topics, including the Datadog product, my background, and the company's direction. I met the two founders of another startup that Datadog had acquired, who shared their experience integrating their product into the larger company. The CTO also spoke with me about technical challenges and growth. An NDA was signed before my trip to Paris, ensuring open communication about technical details. Despite discussions with multiple people at various levels of the organization, no concrete offers were made, but I kept working on Checkly as if nothing was happening. Ultimately, Datadog decided that I would have to move to Paris for an agreement, which was a deal-breaker for me due to personal and professional reasons. The experience was valuable, and I learned a lot about the process and the company, even though it didn't work out.