803: MASTERMIND | Laugh Your Way Through It: A Comedic Masterclass on Life, Love, and Being Ridiculous

from The Rachel Hollis Podcast · host Rachel Hollis

In today's Mastermind, we’re serving up a comedic masterclass featuring some of the funniest minds to ever hit a mic—Bert Kreischer, Nikki Glaser, Tiffany Haddish, and Gabriel Iglesias. From brutally honest relationship takes to embarrassing moments that turned into life lessons.Get your copy of Rachel's New Book Here: Audible, Amazon, Barnes & Noble, Books-A-Millon, Bookshop.org, or wherever books are sold!Featured Episodes | 377: Nikki Glaser | 600: Tiffany Haddish | 417: Bert Kreischer | 370: Gabriel Iglesias01:34 Mastermind Episode: Comedic Masterclass02:22 Nikki Glaser on Self-Acceptance and Body Image05:30 Struggles with Pot Use14:37 Tiffany Haddish's Comedy Journey20:45 Early Career Hustles and Lessons22:23 Nostalgia for Early Podcast Days22:51 Early Career and Challenges23:37 Standup Beginnings and Will Smith Discovery24:30 Hosting and TV Pilots26:40 Travel Channel and Rogan's Advice28:37 Showtime Special and Career Low Point33:18 Comedy Club Performances and Early Struggles34:42 Financial Lessons and Business Growth40:01 Reflecting on Success and MistakesSign up for Rachel’s weekly email: https://msrachelhollis.com/insider/Call the podcast hotline and leave a voicemail! Call (737) 400-4626Watch the podcast on YouTube: https://www.youtube.com/c/RachelHollisMotivation/videosFollow along on Instagram: https://www.instagram.com/MsRachelHollis To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

What this episode covers

In today's Mastermind, we’re serving up a comedic masterclass featuring some of the funniest minds to ever hit a mic—Bert Kreischer, Nikki Glaser, Tiffany Haddish, and Gabriel Iglesias. From brutally honest relationship takes to embarrassing moments that turned into life lessons. Get your copy of Rachel's New Book Here: Audible, Amazon, Barnes & Noble, Books-A-Millon, Bookshop.org, or wherever books are sold! Featured Episodes | 377: Nikki Glaser | 600: Tiffany Haddish | 417: Bert Kreischer | 370: Gabriel Iglesias 01:34 Mastermind Episode: Comedic Masterclass 02:22 Nikki Glaser on Self-Acceptance and Body Image 05:30 Struggles with Pot Use 14:37 Tiffany Haddish's Comedy Journey 20:45 Early Career Hustles and Lessons 22:23 Nostalgia for Early Podcast Days 22:51 Early Career and Challenges 23:37 Standup Beginnings and Will Smith Discovery 24:30 Hosting and TV Pilots 26:40 Travel Channel and Rogan's Advice 28:37 Showtime Special and Career Low Point 33:18 Comedy Club Performances and Early Struggles 34:42 Financial Lessons and Business Growth 40:01 Reflecting on Success and Mistakes Sign up for Rachel’s weekly email: https://msrachelhollis.com/insider/ Call the podcast hotline and leave a voicemail! Call (737) 400-4626 Watch the podcast on YouTube: https://www.youtube.com/c/RachelHollisMotivation/videos Follow along on Instagram: https://www.instagram.com/MsRachelHollis To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices.

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803: MASTERMIND | Laugh Your Way Through It: A Comedic Masterclass on Life, Love, and Being Ridiculous

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This episode is 41 minutes long.

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This episode was published on April 17, 2025.

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