The Skinny Confidential Him & Her Show

Episode: Jeffree Star: Unfiltered, Uncensored, Speaking His Truth, & Redefining Success on His Own Terms

Hosts: Lauryn Bosstick & Michael Bosstick
Guest: Jeffree Star
Date: November 17, 2025

Episode Overview

This episode features an unfiltered and vibrant conversation with Jeffree Star, beauty mogul, rancher, and cultural lightning rod. Lauryn and Michael dive into Jeffree's journey from MySpace fame to building a cosmetics empire, his pivot to yak rancher in Wyoming, navigating internet culture and cancel culture, redefining gender and identity, and his personal philosophy on business, confidence, and living authentically. The discussion ranges from entrepreneurship and internet trolling to sex, spirituality, and the politics of modern culture, all delivered in true Jeffree Star candor.

Key Discussion Points and Insights

1. Jeffree Star’s Business Evolution & Entrepreneurial Mindset

• Early Hustle & Business Instincts

  • Jeffree discusses his drive from a young age, growing up with adversity and channeling that into an entrepreneurial mindset.

    “I just had it. I feel like it was like instilled in me to just be a hustler. I come from a very rough background—no money. My mom was a single mom, we grew up poor. I just had to learn to hustle.” (07:21)

  • Started as a makeup artist for celebrities, then pivoted through MySpace fame to music, and ultimately founded Jeffree Star Cosmetics with three liquid lipsticks.
  • Took a major risk, invested his last dollars, and paid back his investor the day of his first launch.

    “The first one was just taking a risk on myself... I started this dream with three liquid lipsticks and a hope that it might work. And it sold out in five minutes.” (19:12, 20:42)

• Scaling the Beauty Brand

  • Jeffree gives a peek behind the scenes—his company went from his apartment to a cosmetics powerhouse with in-house fulfillment (Killer Merch).
  • Emphasizes investing the first profits back into the brand, expanding slowly and methodically:

    "My advice to anyone is invest in yourself. The first million, the first $2 million, we put right back into the business... A lot of people get newly rich, spend it all, don't invest correctly." (23:48)

• Authenticity as Strategy

  • “I’ve never created something for the customer. I create things for me and the customer." (24:30)
  • Discusses being hands on with every detail, manufacturing globally to ensure quality (“These are made in Czech Republic. I love traveling the world and making things in other places.” 04:34)

2. Social Media, Internet Culture, and Cancel Culture

• Rise through Platforms

  • Started with early YouTube and MySpace. Built mystique by never showing himself without makeup until 2014—then shocked viewers with vulnerability.

    “From MySpace until about 2014, I never let anyone see me without makeup... That was my mystique." (08:54)

• Navigating Cancel Culture

  • Strong opinions on cancel culture’s evolution; believes in growth, accountability, but also criticizes the lack of nuance:

    “Cancel culture has evolved and changed... I think people are allowed to grow and change. If you still think someone's a piece of sh*t, hold them accountable. But for a while, no one wanted anyone to grow. I never took that as an answer.” (59:50 – 61:15)

• On Internet Trolls & Haters

  • Jeffree shares how trolling has changed, people seek attention, and his methods for handling it:

    “On TikTok, if someone says something crazy, I invite them live, and they're like, ‘I just wanted your attention.’ That did not exist in the older social media days.” (16:29)

  • Claims he’s never been fazed by hate:

    “It feels like nothing... I like to clap back and be funny when I'm in the mood.” (17:33)

3. Personal Life—Wyoming, Yaks, and Redefining Success

• The Move to Wyoming

  • Burnt out by LA, materialism, and the pandemic, Jeffree fulfills his dream of rural life.
  • Embraced by locals after initial skepticism, invests in the community, and finds peace in nature:

    “I fell in love with the ranch... There’s instant peace, stress gone, vanished. I land here, I want to throw up. Not just from the pollution.” (42:43)

• Building a Ranching Business

  • Accidentally becomes one of the largest yak ranchers in America; discusses the ethical side of meat production and the wild world of “yak drama.”

    “There's not that many... maybe like 50, maybe less than a hundred serious yak breeders. I bought from all of them.” (49:01)

  • On responsible and ethical meat:

    “A lot of people think meat comes from the grocery store—it’s not real food... My animals are roaming free, grass-fed... and I realized that fast food wasn’t real.” (47:11 – 48:26)

  • Owns the Jeffree Star Store in Casper: makeup and meat under one roof.

4. Gender, Identity, and Social Commentary

• On Individuality and Gender Discourse

  • Jeffree rails against collective shaming and affirms the need for tolerance:

    “I miss the days when we could sit down... have healthy conversations, and be friends. Now it’s like, ‘Oh you don’t like what I like? I'm blocking you. I hate you.’” (11:36 – 12:14)

  • On the confusion in contemporary gender/identity conversation:

    "Your identity issues and who you think you are is so separate [from sexuality]. I don't agree that they should be together.” (84:49)

  • Stands by protecting women and children, questions messaging to kids, and applauds parents who let children simply ‘be’ themselves.

• On Fluidity & Authentic Attraction

  • States he doesn't identify as gay and is open to relationships with women or men:

    “That's another misconception: I am not gay. I am just open and very me." (84:19)

  • Engages in frank, humorous dialogue about sex, attraction, and the complexity of modern relationships.

5. Reflections on Money, Confidence, Giving Back & Legacy

• Materialism vs. Fulfillment

  • Admits to buying everything he never had as a form of self-validation until he realized it was hollow:

    "No matter how many designer clothes and diamonds and cars you buy, it's all just fucking materialistic shit." (27:01)

  • Finds real happiness in travel, experiences, and rural living.

• On Confidence and Handling Criticism

  • Encourages self-acceptance:

    “I wish people would be less harsh on themselves. I wish they would not care what a stranger thought ...” (96:19)

• Giving Back

  • Invests in his Wyoming community, donates millions, but keeps it quiet:

    “I don’t need the validation of, like, ‘Look, guys, I’m a good person.’ I know I’m a good person.” (71:08)

Notable Quotes & Memorable Moments

• “You want to stay married, you gotta be moisturized.” — Jeffree Star (00:54)
• “Did you Google Colorado campfire?… It is considered rude if the cracker is not consumed afterwards.” (02:25)
• “My advice to anyone that wants to be an entrepreneur is invest in yourself.” (23:48)
• “I think cancel culture is kind of over… people are allowed to grow and change.” (60:06)
• “If I showed up empty handed, I hope you would slap me.” (00:31)
• “I'm the face of just: do you. You're allowed to rebuild. You're allowed to evolve as a human.” (61:20)
• “Lightning in a bottle.” (multiple times re: business growth)
• “I landed in Wyoming and my instant stress was gone. I land here [LA]; I want to throw up—not just from the pollution.” (42:43)
• “I have never created something for the customer. I create things for me and the customer.” (24:30)
• “They want you depressed indoors. Dark. Blackout. No. I’m sungazing at the crack of dawn.” (91:52)
• “If a random dude on Instagram wants to go get tested or I’ll pay for it.” (83:27)
• “I'm a dick connoisseur.” (96:01)

Important Timestamps

• Opening banter/gifts, magic moisturizer, orgy palette — (00:24–03:53)
• Entrepreneurial origins, MySpace/YouTube roots — (05:39–10:43)
• Business growth, quick scaling, investment philosophy — (19:02–24:52)
• Cancel culture, public persona, authenticity — (59:28–62:10)
• Wyoming move, rural life, community reception — (29:29–41:34)
• Yak business: ethical meat, scaling, industry drama — (45:17–52:10)
• Gender/identity and internet debate — (63:36–88:23)
• TikTok Live and new media strategies — (88:47–89:55)
• Personal life: relationships, sex, monogamy — (93:26–94:56)
• Philosophy on confidence, kindness, legacy — (96:19–96:57)

Tone and Highlights

• Raw, irreverent, and frequently hilarious. Jeffree holds nothing back, freely using explicit language, sharing intimate anecdotes, and providing sharp social commentary—often with a sardonic edge but underlying warmth.
• Showcases remarkable business acumen, self-awareness, and a singular focus on authenticity.
• Demystifies both the glitzy world of beauty entrepreneurship and the grounded reality of rural self-reinvention.
• Pushes listeners to invest in themselves, embrace growth, and “not care what a stranger thought about them.”

Quick Takeaways

• Jeffree Star is the ultimate self-invented entrepreneur—blending business, spectacle, and personal truth.
• Success required risk, continual reinvestment, and relentless authenticity (“never white label!”).
• Jeffree’s migration from LA to Wyoming represents not just a lifestyle shift but a critique of materialism, and a commitment to sustainable, real living—both for himself and the planet.
• Emphasizes tolerance, respectful debate, and living by your own authentic standards, challenging societal and internet extremes.
• Encourages entrepreneurs, creators, and anyone feeling out of place to “be themselves,” invest in their vision, and stay resilient in the face of online hate and shifting trends.

Where to Find More

• Shop Jeffree Star Cosmetics & Yak Meat: jeffreestarcosmetics.com
• Connect on TikTok and social: @JeffreeStar

Special Offer: Use code SKINNY for 20% off on Jeffree Star Cosmetics.

This episode is a wild, insightful ride—equal parts masterclass in business, irreverent comedy, and raw, unfiltered life advice.