The saying goes that you are the company you keep, but this doesn’t seem to be the case with Kayne. While he’s tweeting around for financial support, his celebrity friends are quietly raking in millions from clever investments.

By now, you’d be aware that Kanye has said he’s $53 million in debt after launching his clothing line, which is quite a sum to spend bringing Derelicte to life. No seriously, this is his label:

I guess he was just really excited about Zoolander 2.

To compound his financial woes, Ye is said to have lost a further $10 million by fluffing his Life of Pablo album launch and damning it to a life of purgatory on streaming service, Tidal. Since then, he’s been busy begging Mark Zuckerberg for a billion dollar investment into ‘Kanye West Ideas’.

Mark Zuckerberg I know it’s your bday but can you please call me by 2mrw… — KANYE WEST (@kanyewest) February 15, 2016

Imma let you finish… your birthday?

On Kanye collaboration Diamonds from Sierra Leone, Jay-Z quipped “I’m not at a businessman, I’m a business, man” and it’s easy to see where Yeezy got the dream of rapping his way to the top of a business empire. Considering rappers give some pretty great financial advice, we’re surprised he hasn’t considered investing, like all his business-savvy celebrity friends.

Next time Kanye has cash burning a hole in his pocket, he should use some of the following investment inspiration as a guide:

#1 Jay-Z

Jay literally started out selling CDs in the back of his car before forming Roc-A-Fella records in 1996. Since then the label has expanded to a multi-headed empire encompassing entertainment, fashion, nightclubs and even a sports agency. Jay-Z’s fortune traces back to the sale of the Rocawear label for $204 million in 2007.

#2 Ashton Kutcher

Ashton earned $750,000 for each episode of Two and a Half Men he suffered through, and certainly put it to good use. The actor turned business angel invested in dozens of startups including Uber, Skype, and Airbnb. He even has some sound investing advice for dear Kanye: “The companies that will ultimately do well are the companies that chase happiness. If you find a way to help people find love, or health or friendship, the dollar will chase that.”

#3 Shaquille O’Neil

The retired NBA-player has a net worth pipped at $350 million including a stake in the Sacramento Kings and 10% of burger chain Five Guys. However, his policy of only putting money into things he personally enjoys has cost him in the past. Shaq famously passed on early investment in Starbucks with the rather silly claim “Black people don’t drink coffee”.

#4 Magic Johnson

Thankfully, fellow basketball legend Magic Johnson doesn’t judge his cafés on racial lines. He owned 105 early Starbucks franchises and eventually sold them back to the parent company for $27 million in 2010.

#5 Bono

When Bono isn’t screwing his beloved Ireland out of tax revenue or automatically installing his album onto every iPhone in the world, the megalomaniac is actually a pretty sound investor. In 2009 his fund, Elevation Partners, paid $86 million for a 2.3% stake in Facebook, then flipped it for a whopping $1.4 billion in 2013.

#6 50 Cent

Rapper 50 Cent had a stake in Vitamin Water when it sold to Coca-Cola, reportedly earning him as much as $100 million in 2007. Sadly he squandered most of it buying everything from a fleet of cars to Mike Tyson’s mansion and was left with little when he entered Chapter 11 bankruptcy last year.

#7 Madonna

Madonna made a wise $1.5 million investment into her favourite Vita coconut water in 2010, reportedly drinking it daily to stay hydrated on tour. Last year Red Bull China purchased a 25% stake in the company at a $665 million valuation.

#8 MC Hammer

MC Hammer has been an investor in streaming music service Pandora since the days when it was called Savage Beast. Since then, he’s invested early in eight different tech companies including point-of-sale payment app Square and magazine app Flipboard. Hammertiming all the way to the bank.

#9 Dr Dre

The medically unqualified/musically overqualified Dr Dre famously met with label boss Jimmy Lovine to ask for advice on selling shoes. “F[orget] sneakers,” said Jimmy, “let’s make speakers!” When the pair sold their Beats headphones company to Apple last year, Dre made $620 million, noted by Forbes as the largest annual earnings of any musician in history.

#10 William Shatner

Known for his role as Captain Kirk in Star Trek, Shatner became spokesman for price comparison service Priceline in the heady days of the first tech boom, and was smart enough to take payment in shares instead of cash. By 2010, the move earned him $600 million.

Live long, invest and prosper!

Matthias McGregor writes from Delillo’s fictional Pop Culture Dept, here to “decipher the natural language of culture, to make a formal method of shiny pleasures—an Aristotelianism of bubble gum wrappers and detergent jingles.”