The youngest comedian to ever win 'Last Comic Standing' says she's making millions more than when she started her career - but getting there was a 'slow burn'

• Over the course of 10 years, comedian Iliza Shlesinger has gone from winning NBC's Last Comic Standing to premiering Netflix specials and an upcoming comedy series.
• Shlesinger spoke to Business Insider about all things money, from how she built her wealth to how she prefers to spend it.
• "I've realized things aren't as bad when you put your phone down," Schlesinger said of the way comedy works in today's news cycle.
• This is part of Business Insider's new series, "Let's Talk About Money."
• Visit Business Insider's homepage for more stories.

Comedian Iliza Shlesinger is thriving.

The 36-year-old won NBC's Last Comic Standing in 2008 when she was 25 and remains the only female and the youngest contestant to do so. Like many other millennials, Shlesinger has mastered the hustle of multiple jobs: When not performing stand-up comedy around the world, she has found time to host her own late-night talk show, author a book of essays, co-star in films, and helm her own podcast.

That's not to mention Shlesinger's five Netflix specials, including "Elder Millennial" and "Unveiled," the latter of which aired in November 2019. Up next: The Iliza Shlesinger Sketch Show, slated to premiere on Netflix this year.

As part of its new millennial series, "Let's Talk About Money," Business Insider spoke to Shlesinger about her journey to comedic stardom and the wealth that came with it. Here's Shlesinger on her first $1 million, the importance of honesty, and what it's like driving a Honda Civic Hybrid around an expensive neighborhood.

"Let's Talk About Money" is a series of conversations with millennials about wealth. Interview has been edited and condensed for clarity.

Hillary Hoffower: Your commentary often centers around relationships and the differences between men and women. To what extent does your generation inform your comedy, and in turn, how do you think your material speaks to your generation?

Iliza Shlesinger: Elder millennials, we're the oldest of the younger generation, we're just now getting into the mid-30s and taking on the roles our parents had.

Coming into this new era in the wake of the Black Lives Matter and Me Too movements, we're doing our best to lead the world and do it in a meaningful way. There's never been a better time to be a woman, a person of color, trans or gay ... While things are difficult, it's the most progressive time. I lead with honesty. It's a big part of being young today. It's about being open to having a conversation.

Hoffower: What was the biggest learning moment in your career?

Shlesinger: It's more the realization that saying you can't please everybody isn't just a clever aphorism you put in an Instagram post. I really am here to make people laugh and not hurt anyone.

And if someone's offended by it, it's about moving forward with grace and commitment to craft and comedy. We live in a 12-minute news cycle - I've realized things aren't as bad when you put your phone down.

Hoffower: You are the first and only female winner of Last Comic Standing. What's your advice for women trying to achieve success in a male-dominated industry?

Shlesinger: Your career path will not look like everyone else's. You can't compare yourself to other people. Keep your head down and keep creating opportunities for yourself, no one will do it for you. Be self-generating, self-creating, self-promoting, love what you do, and you will go far.

Hoffower: Do you find there to be a wage gap in comedy?

Shlesinger: There are wage gaps in random increments. It's very available for me to see how much a male comic at my level charges. I don't find venues price tickets differently, because they want the money. The audience grows with the demand, and the market dictates what your ticket price should be. There's more of a gender bias in terms of perception. These are things we work to disprove.

Hoffower: How much more are you making now than when you started and how did you make that leap so quickly?

Shlesinger: Millions. And it's not a leap, it's a slow burn.

Prior to the Netflix specials, it was about the commitment of going into cities over and over and hitting those comedy clubs. Those first two specials, we started to see growth within that, so the model sale for ticket pricing was different. A couple of specials in, we dipped our toes into theaters. It's been a build - it hasn't been a rocket ship, but it's been a fast build by the last couple of years. In the last two years, business has grown exponentially.

Hoffower: In a 2016 interview with Forbes, you referenced having made $1 million in 2015. What did you do with that money?

Shlesinger: I don't spend money on huge things; I spend on necessary things like travel, hotels, and necessary evils in my life. I still drive a 2009 Honda Civic Hybrid, and I continue to drive it because it's a hybrid. I'm not a dude, so chicks don't care what I drive. I love living in an expensive neighborhood and driving it around.

Hoffower: What's the best $50 you've ever spent?

Shlesinger: I'm on set for 10 to 12 hours a day and in various conditions. The other day, I spent $45 getting a Chinese chair massage. I asked her to rub my head, and I floated out of there. It helped me get into hair and makeup the next morning.

Hoffower: What's the worst money advice you've ever gotten that you've followed?

Shlesinger: Anything I've ever heard in a rap song. I don't need a $30,000 gold chain.

Hoffower: What does financial success mean to you?

Shlesinger: It's so different from creative success. It's the ability to live freely and not have to be anxious when you look at your bank account. It's knowing you can generate more opportunities for yourself and shape your life, within reason.

Hoffower: What's your last receipt from?

Shlesinger: Who keeps receipts?