That's just how the game goes, very few have the money they are perceived to, esp. in that life. And, yeah, the investments, you try to make a few moves, in the legit world, but the start up costs are higher and profits way lower, so you can lose, in a 6 month time period, what you just made in the last 9 months, and then have to double down to get it back.
Sounds like you kept it simple and neat, and that's the right way, but when you are moving work like he was (which isn't anywhere near the top, but mid level trafficker) it gets messy. You have factions of people working under you, internal feuds, shifting loyalties, and suppliers is another thing. You may start paying off one with another's money, when you take a loss, and then find another, and open up a line of credit there. It gets messy, by definition. You need methods to move the money back to sources of supply, you need to bring the work TO where you are, or the points don't work.
Seen my friends up close go through this, where you end up a few hundred thousand in debt, off a bad 60 day run.