What to spend on and why is a complete and utter judgement call and quite subjective. The examples have to be pretty extreme before you can declare wasteful.

What to spend on and why is a complete and utter judgement call and quite subjective. The examples have to be pretty extreme before you can declare wasteful. Maybe they are, but all you can really say is that you have two different approaches and personalities, and that is something you have to figure out before getting into bed with someone who either doesn't work the way you approve of or understand. They may think you are sabotaging the business by being too myopic and focussing on the wrong details. Failing to deliver the load of goods by avoiding buying the truck or the fuel, or attract the right driver, or attract the right customer. Personally the cost of such a retreat wouldn't matter to me at all. What would matter is if the employees consider it just more insufferable work imposed from out of touch bosses, or actually a good thing. What is the stated purpose of the reatreat? Is that purpose valid? Does it actually attain that purpose? It sounds like you have no idea about any of those questions or their answers. Is that because they were never communicated or the cofounder has no idea either, or might it just be that you don't see it and it's really just a limitation of your own? An event like that is not automatically damning, but acting like it is, is actually a bit of a red flag against you, as though you don't recognize any indirect values and only think that spending money is bad. There is always the "in this economy" excuse. It can be said every day forever, and so is actually meaningless. A retreat like that is more likely to be a bad idea if it's some horrible forced-fun work-intruding-on-personal-time thing that only the boss wants, no one else wants, and the boss has no coherent plan and purpose that maybe makes it correct to initially override what everyone says they want.