I don’t blame you, we all have a lot of things to deal with. I wouldn’t worry about ending up in debt from it if you are a tech worker with a significant financial cushion.

I wonder if there’s an opportunity here for a “free travel consultant” who will sign up for credit cards for you, take a cut, keep you up to date on the benefits you’ve accrued, and act as a travel agent, booking trips in a way that maximizes the value of the benefits. If done well, it might make life simpler instead of more complicated.

You can't just keep signing up for credit cards and get benefits. They will decline you soon.

True, but you can get thousands of dollars a year in benefits if you optimize it.

Sure. The "free travel consultant" just wouldn't work.

Why not? If they take 25% of a few thousand per year, that’s hundreds of dollars of annual revenue per customer - great if they can do it mostly through software.

That's a cool idea--I would probably give it a try.

"then ended up with thousands of dollars of credit card debt a few years later because they got carried away. No thanks. "

That really isn't necessary. I haven't paid a single cent in interest in 18 years. Get the credit card, buy a few things, pay it off and throw the card away.

If you have a business you most likely have the discipline to not be stupid.

I know it isn't necessary--just pointing out that pride often goeth before fall with these things, and since people who are otherwise financially successful are unlikely to admit to these kinds of problems, it's easy to have a skewed idea of how common they are. I know people who are financially savvy, business owners, etc., but still have had debt troubles at various points in their lives.

Probably true. After all, being in debt is the "American Way" :-)