I worked on a breach where during the investigation we found reverse tunnels out of the network (back to the VP's house) where he'd been working on stuff unbekn

I worked on a breach where during the investigation we found reverse tunnels out of the network (back to the VP's house) where he'd been working on stuff unbeknownst to the firm. They had a VPN to a competitor that a sales engineer had setup when they were exploring collaboration, that had never been closed. Their DMZ was awesome on paper (cool color chart) but was literally non-existent. The final icing on the cake, their network equipment and firewalls were all second hand with existing firewall rules left when new ones were added. After printing out the rules.. at the very bottom ANY/ANY. There wasn't a lack of money, hundreds of millions were dumped in by investors. Everyone there had the i'm an engineer so I don't have to follow rules, that's for the sales guys attitude and that more than did them in from a security perspective.