40K to start working for yourself-WWYD?

There are so many factors in this. With a family to support depending on your wife's job, I don't think 40k is near enough unless you had some great business plan and a group of investors.

Could easily be done with $0.01. Success is when hard work meets preparation.

What do you want to do? Are you passionate about it? Do you already posses knowledge on and of it?

In college I had no scholarships and no financial help from my family. I did have an abundance of tools and a working knowledge of how to fix things. I was a handiman all throughout school. If I didn't work I didn't eat. But I loved what I did and I still get phone calls from people I worked for or their friends asking me to come do work.

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Assume this hypothetical family could totally live off of spouses income for 18 months.

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Okay - is $40k enough to get into one of those independent vending machine routes? I mean, it isn't enough to franchise anything. $40k of inventory is nothing, so you're not going to be able to sell anything in volume.

Does the hypothetical person have a craft or trade, such as building cabinets, furniture, etc.? At the high end, custom level, that can still be lucrative. You will need to build a network of contacts to get to customers who want custom cabinets/furniture built.

A web based retail shop might work if you can acquire/produce specialized items with a steady demand - you can at least keep the overhead low with such a model.

I know it is common sense, but you have to find a market that is underserviced and develop the skills and experience to operate within that market.

Otherwise, you're going to be really scrapping for customers in a bloated/saturated market (think personal injury lawyers - the guys at the top are making a fortune, by spending a fortune on advertising - and that's a profession requiring extensive education, licensing, etc.)

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Experience with insurance has been on the consumer commercial side, not selling. More knowledgeable about real estate than anything (although that might not be saying much). Have had some success with a couple investment properties, and I know the market, just have to learn the actual hard parts-contracts/deeds/etc....

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Well - real estate or insurance, you're not just going to jump out with your own agency - you're going to go to work for someone else - at first. Now, being on commission, that $40k may provide some cushion, but we're already talking about living on the spouse's income for 18 months. There should be little to no overhead in working as a realtor or insurance agent for someone else.

Certainly $40k isn't going to buy someone out of their agency or realty - at least not one worth buying.

Start taking steps towards your new business while you are still employed. Take a seminar, study some books, etc. Also try to actually make part time $$$ on it before taking the plunge.

Toe in the water approach is better than jumping right in in this instance.

There are a lot of businesses for sale, and some offer owner financing. If you found the right one who would work with you for 40K down then you could potentially walk into an existing business that is already cash-flowing. There are a lot of crappy businesses for sale too though, so do your homework on why the business is for sale if you go that route.