When to start paying others instead of DIY?

[Dan Stewart]

Hey Guys,

So I have two businesses that are starting to take off. Our vacation rental business and my fishing charter business. My dad has always taught me to just get things done and if you can fix it yourself, why pay someone else? In some cases where I am too far away from our properties or don't know how to do it, I have been paying others. If I can get a job done quicker with some help, I have paid a buddy to come over and help me. With my dad being an extremely knowledgeable contractor, pretty much anything that comes my way I can get done on my own or with dads help. However, lately, I am starting to wonder if I should start hiring more out. I am not getting rich by any means doing these two businesses. However, I am starting to wonder if I was hiring out more if might be able to get more accomplished doing something else more productive. 

 What are your thoughts on this? When do you know it's the right time to put more work in other peoples hands?

I would also like to start thinking about my next deal. If I do this, I will definitely need more help.