I know about the two blokes in Florida who were caught trying to sell $30k worth of bitcoin for cash and were charged with money laundering (among other things). But have there been any cases of people getting caught laundering through their business?
Say a business online is selling services for bitcoin, putting the bitcoin directly into coinbase or wherever, selling it for cash and treating it all as profit and paying taxes on it.
If a business's sole revenue was via bitcoin -> USD, would that raise any red flags? Would there be any risk or worry about getting audited for laundering? If so, what steps would you take to mitigate it?
Laundering is different than you describe. Laundering is legitimizing income. It is different than tax evasion. Tax evasion is not paying taxes. Laundered money might have taxes completely paid but you obfuscate the source of your income.
Small businesses are more likely to be audited
Cash based businesses are more likely to be audited
I'm sure coin based businesses are more likely to be audited.
So if by red flag you mean are you at increased risk of an audit, then yes you are. If you are legitimate keep very good records. If you aren't engaging in money laundering or hiding the true nature of your business keeping good records should be sufficient. Paying your taxes timely is important. If you are engaged in something illegal then know what you are doing. While the chances of an audit overall is small, the business you describe would be considered one that the IRS would be interested in.
What in trying to say is that fully paying your taxes isn't a sure fire way to avoid an audit. But paying your taxes certainly helps. Also don't overpay your taxes. That's a red flag as well. Do proper accounting procedure. Bc the only people who overpay their taxes and pay more than they owe by a substantial amount are those money laundering