On CW's "Crazy Ex-Girlfriend," co-creator Rachel Bloom plays a successful attorney who moves across the country to pursue a long-dead relationship with her high school ex-boyfriend. In real life, Bloom is a professional inspiration for millions. Her show has garnered awards and critical acclaim and was picked up for a third season by CW at the beginning of the year. But Bloom hasn't followed a linear path to success. After graduating from New York University with a theater degree, she moved back to her home state of California, where she worked with an agent in Los Angeles, auditioning for TV spots. The auditions proved fruitless, so she decided to pivot and put her energy toward another project. "While I was there, I was like, I might as well do something with my time," she tells Wealthsimple. "That's when I finished making the video for this song I wrote, 'F--- Me Ray Bradbury.' I spent $3,000 — the bulk of my savings — to make the video."

Although the profane, hilarious video racked up more than four million views on YouTube, Bloom created it as a creative outlet, not for financial gain. "This was 2010, so it may have been before YouTube ad monetization," she says. And she's never regretted draining her savings account to make it happen. "I made it because I wanted to be my own one-person sketch group. And that song has paid for itself back thirtyfold," she tells Wealthsimple. "It got me my first TV staff writing job on a very short-lived Fox animated show called 'Allen Gregory.'" From there, Bloom landed gigs writing for a variety of shows, including "Robot Chicken," before shooting the pilot for "Crazy Ex-Girlfriend" with Showtime. After that network passed on the show, Bloom and her team were forced to shop it elsewhere. At first, nothing took hold, and Bloom went back to writing for "Robot Chicken." "We got nine passes in one day," she says. "It was rough."