You begin to sail the raft, you start fishing while out in the open seas. You reach another island and sell the fish, figure out that is the way you can have an easy life since you can pay other people to procure food, water and wood with fish. You build a better boat, hire more people and repeat the process.
You now have a huge rowing boat that goes very far out at sea since there are no fish left close to land, you now fully depend on the people on that boat to make it alive to the next island. There are people who row, people who fish, people to cook, people that are on the lookout for fishing spots and islands.
Your partner notices a guy who eats more than the average rower on the boat, but rows less. You throw him overboard. A fire starts near the rowers, but the rowers continue rowing. Turns out the guy you just threw overboard he always put out fires. You find another rower, tell him to put out the fire. He throws water over it. It is now worse. You figure out the fire is the cook's fault for using too much oil. He only used so much oil because the lookouts thought fish oil is good for their eyes so they can see more ahead. You know this to be only partially true, but they don't seem to understand and even though the fire happened they still demand their food fried in fish oil.
You throw one of the lookouts in the water to make an example. The lookouts stop eating deep fried food. Now the people who fish complain they work too much. Turns out the deep fried food gave the lookouts energy to shout at the people who fish where to fish at. Now, the people who fish need to stop what they're doing and go to the lookouts for information. Because of all the extra effort the people are doing, you are now out of fresh water in the boat.
Congratulations, you now know how a CTO feels like.