I don't know why you assume those tasks are similar in difficulty. In general, if you don't factor in the chance of getting caught, it's easier to make money with a an illegal scheme than a legal one. Nobody would break the law if it weren't so.

I can't reply to all comments, so since you posted first I'm replying here...

It's a minor thing to learn a criminal skill that lets you con your way into a couple thousand dollars. The combination of knowledge, connections, moxie, and motivation to raise an ill gotten 37 million dollars are another thing entirely. Not anyone can just say "oh sure I'll lie my way to 37 million". Given the skills, time, and dedication it must have taken to get this far by a person with these talents, could have been used to be reasonably successful in a whole host of careers or ventures. Perhaps not 37 million effective, but enough to live comfortably and happy for sure, without the constant fear of the long arm of the law creeping up behind you at any moment.

I don't know why you assume those tasks are dissimilar in difficulty. Have you tried both?

If you have gold worth a thousand dollars you can walk into a jewelry shop and pawn it for some large fraction of that.

If you don't any gold, and walk into a jewelry shop and ask for a thousand dollar loan, they're laugh.

If your uncle jack owns the jewelry store, they might lend you money on no credit.

If you have some amazing way to fake having a thousand dollars in gold, you can fake jewelry store into loaning you the thousand dollars. But they'll be gunning for you if it becomes clear you've scammed them.

If you have a business that's making money and has valuable assets, your chances of getting loans and investment is fairly high.

If you have a track record of founding businesses, if you have a good idea and if you have connections, your chances of getting investment, even with no business or a minimal business, can also be pretty good.

But this is the skill of faking a real business is somewhat different from the skills of those with a track record of creating multiple real business from scratch. There's similarity, even overlap but they aren't identical.

> The alleged Haddow is intelligent and capable enough to raise 37 million

For one thing generally a portion of any 'success' is linked to either lies or illegal activities. It's quite easy to make money if you fabricate things.

If he tells the truth, then he's pitching a different less-enticing business, and there's no reason to assume he would succeed at that.