His collaborations with Nike, on the wildly popular Nike Air Yeezy sneakers, did not stem the losses. West has said he was not given a percentage of the sales—a sticking point that eventually caused him to defect for what would appear to be a more lucrative deal and more creative license at Adidas, where he was able to expand into clothing and elaborate fashion shows at sold-out arenas three times in the span of one year. In his first “season,” West told BET he went $16 million in debt getting his line off the ground.

Those numbers, while significant, are not surprising to industry insiders tasked with coming up with business plans for people like West, who have grand visions without the slightest idea of what they might cost to execute. The expenses related to production, sales, buying, marketing and setting up the infrastructure to manage the logistics of a fashion line are one thing, according to Jonathan Reed, C.E.O. of brand consultancy CS Global. But scaling the product and setting up a show is what really drives up the capital requirement.

“For a large show, you’re thinking about venue expenses, set and stage expenses, audio and special effects, labor costs, which at a place like Madison Square Garden, which is union, is more expensive. This can run into seven figures very quickly,” he said. “That doesn’t include any of the talent—models, hair, makeup, stylists. That’s its own huge bucket, another easy seven figures.” The cost of recording the spectacle, which often requires multiple crews shooting front-of-house and backstage at the same time, plus back-end production, only adds to the cost. “As a general statement, it would be very easy to amass large amounts of debt in the costs of producing a collection, putting it together, showing a collection, and then selling a collection,” Reed said.

The fashion business is famously treacherous for novices. As Natalie Portman may have learned with her ill-fated 2008 footwear line, the sourcing is expensive, as is labor and marketing. It’s hard to get good counsel, especially for celebrities. “Musicians get terrible advice. They surround themselves with people who are fans or wannabe musicians who couldn’t make it on the stage so they became accountants or attorneys,” said Jane King, a money manager at Fairfield Financial Advisors, who works with clients in the entertainment industry. “It’s an ego tip, because artists have plenty of money to get into other businesses. But has anyone done a five-year projection of what the bottom line will be? I doubt it.”

But with West, however, one suspects this isn’t the case. On one level, his exorbitant debt does not appear cause for real financial concern. Instead of financing his creative side projects through his main money-making artery—each concert on his 2013-2014 Yeezus tour reportedly grossed $1 million, according to Forbes, which, along with a spate of successful albums, helped him bring in a total of $72 million pre-tax over the last three years—West is presumably seeking funding through bank loans or venture partners. Most of the world’s sophisticated investors separate their personal assets and savings from their venture funds. This, in some ways, explains how Donald Trump could file for bankruptcy multiple times and remain a billionaire. And it also suggests how Silicon Valley venture capitalists could elevate—and, in some cases, inflate—the value of various tech companies while carrying little of the personal risk themselves.

In some regard, West’s tweets may simply have been an elaborate and modern version of a pitch deck in search of that true marker of early-21st-century creative genius: Series A funding. Indeed, he publicly solicited the help of Mark Zuckerberg, whom he asked for $1 billion to keep making art. He also said he would be willing to accept money from Google’s Larry Page. Any other hedge funder or bigwig with pennies to spare would do, too. These guys, after all, know that $53 million is a small price tag for a moon shot.