That awkward moment when your business venture is an interstate drug smuggling organization.

An investment plan hatched among a group of high-achieving Madison high school and college friends has begun to pay new dividends: federal prison sentences.

That’s because the plan, administered by UW-Madison business students or graduates, involved driving to California at least 19 times with bundles of cash to buy hundreds of pounds of marijuana for sale to customers and “investors” in Madison, according to federal prosecutors.

Seven men were charged in U.S. District Court last spring with conspiring to buy, transport and deliver marijuana in loads varying from 5 to 50 pounds, according to Assistant U.S. Attorney Robert A. Anderson. All pleaded guilty.

“Most of them were business students, smart kids who saw a business they wanted to profit from,” he said.

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“They would get drivers to drive to California and take large sums of money, $75,000 to $80,000 in cash,” he said.

The recruited drivers sometimes stuffed the cash into cereal boxes, Anderson said.

Once, two drivers in the car were stopped by police in California, had 26 pounds of marijuana confiscated and were convicted of possession.

[…]

“The guys … collected the money by asking their friends and associates if they wanted to invest, and they then had to give that money upfront. Those who invested got the good price, and when it got here they would break it up, take their 5 pounds and break it up,” he said.