Did you or anyone you know ever get into the billboard advertisement business?

Anything that's worth anything has some kind of a headache to it.

I never said the headache was permanent.

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Is it profitable? Worth the headache?

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A friend of mine did very well starting his own business. A few hundred Billboards. Sold to Lamar. Now he's starting another.

Depends on what you are thinking.

If you're talking soup-to-nuts running your own operation, you'd better know what you're doing. Involves scouting optimal locations. Understanding local ordinances. Dealing with property owners. Negotiating leases with them. Procuring materials, construction teams, safety and efficiency during construction. Contacting advertisers and contracting with them, maintaining the boards, long hours on the road searching for new locations, etc., etc.

It is a challenging gig, but rewarding if you master it.