The Fat Jew Returns! – How Josh Ostrovsky AKA “The Fat Jewish” Conquered The Internet & Sold A Massive Wine Business

By | October 31, 2024

#262: On this episode we sit down again with our friend Josh Ostrovsky AKA “The Fat Jewish”. This is Josh’s second appearance on this show. Outside of being a massive online personality, Josh is also an entrepreneur and branding expert responsible for creating Swish Beverages which created White Girl Rose and the Babe family of sparkling wines. In 2019 the company was acquired by Anheuser-Bush. Today we have a well rounded conversation that goes in many different directions. Sit down and enjoy this wild ride!

To listen to Josh’s first episode on TSC podcast click HERE

To connect with The Fat Jew click HERE

To learn more about Babe Rose click HERE

To connect with Lauryn Evarts click HERE

To connect with Michael Bosstick click HERE

Read More on The Skinny Confidential HERE

For Detailed Show Notes visit TSCPODCAST.COM

To Call the Him & Her Hotline call: 1-833-SKINNYS (754-6697)

This episode is brought to you by Nutrafol

THIRTY MILLION women experience hair loss. But it’s not openly talked about, so going through it yourself can feel lonely and frustrating. It’s time to change the conversation and join the thousands of women standing up for their strands. Nutrafol is formulated with potent botanicals to help you grow hair as strong as you are and it’s physician-formulated to be one hundred percent drug-free. Visit Nutrafol.com and use promo code SKINNY for 20% your order and free shipping. 

This episode is brought to you by BETABRAND and their Betabrand dress pant yoga pants. To try these pants go to betabrand.com/skinny and receive 20% off your order. Millions of women agree these are the most comfortable pants you’ll ever wear to work. 

This Episode is brought to you by Beet Elite   Do what we did. Take your game to the next level with Beet Elite by going to www.LiveHuman.com/skinny and get 20% off your first purchase. The team at Human is making this offer exclusive to our listeners ONLY! 

Produced by Dear Media

Editorial Stories
5 Ways to Set Boundaries with Your Toxic Family Members. Goodbye, Aunt Karen!
5 Ways to Set Boundaries with Your Toxic Family Members. Goodbye, Aunt Karen!
Digital Dopamine Is a Real Addiction—Here’s How to Handle It
Digital Dopamine Is a Real Addiction—Here’s How to Handle It
ChatGPT Remembers Everything About You—But Is This a Good Thing?
ChatGPT Remembers Everything About You—But Is This a Good Thing?
Trending Products
Feel Good Trucker – White Feel Good Trucker – White
NEW
Feel Good Trucker – White

$32.00
Feel Good Trucker – Navy Feel Good Trucker – Navy
NEW
Feel Good Trucker – Navy

$32.00
Related Articles
Our Shows
Over 50 & Flourishing
Welcome to Over 50 & Flourishing, the show for any woman who feels like she lost her compass in the sea of midlife. I’m here to tell you it’s never too late to change your course and awaken the healthy, wise, and wonderful woman within. My name is Dominique Sachse, and I love to ask questions, which was why I spent nearly three decades of my life in the TV news business. I also started a YouTube channel in 2014 to connect intimately with my community, and I took an even deeper dive in my book Life Makeover - Embrace The Bold, Beautiful and Blessed You. I’ll be the first to say, I’ve made mistakes, and I’m not afraid to be vulnerable and learn from them. I mean let’s face it, this stage of life can be complicated. Children are moving out, relationships are being examined, our parents are aging, and we’re having to manage all of this along with our menopause! It’s easy to lose sight of ourselves, but can I just say.. we matter. So, whether it’s finding ways to enhance and celebrate our own beauty, taking bold steps toward living our best life in the second half of life, finding ways to be healthier, happier, and more spiritually connected, I will bring you thinkers and innovators who share the same passion of flushing out these ideas. It’s my goal to leave us all feeling inspired, thought and intent-driven, and with a sense of purpose in whatever we pursue. Let’s celebrate growing older together and embrace our Prime. It’s our time!
Over 50 & Flourishing

Dominique Sachse
Give It To Me Straight
Follow along as this husband and wife duo give you unfiltered advice from two different perspectives. No topic goes unspoken, from sex, money, relationships, the good the bad, and the ugly. Alex and Jon will give it to you straight.
Give It To Me Straight

Alexandra Madison & Jon Bouffard
After Bedtime with Big Little Feelings
Real talk? Modern parenting is a doozy. There’s never been more pressure to be perfect with social media readily at our fingertips - mixed with total isolation and no help. Where the f*ck is that village everyone talks about? Consider After Bedtime your village. Led by Kristin and Deena - founders of the largest online parenting community, Big Little Feelings - After Bedtime is the place you can go at the end of a long hard day to find your “enough”-ness. We’ll laugh, we’ll cry, we’ll maybe pee our pants a little as we unpack things we’re ALL experiencing but too ashamed to talk about: imperfect marriages, miscarriages, managing toddler mania, apologizing to our kids and everything in between. You’ll leave with actionable, realistic tips to make this whole parenting thing smoother - small changes, big impact. In an age where parents need more *real* connection than ever, let’s talk honestly about the hard - and remind ourselves we are not alone, we are not failing. In fact, we’re f*cking crushing it.
After Bedtime with Big Little Feelings

Deena Margolin & Kristin Gallant
Everybody’s Crazy
If you’ve been outside recently, you know that Everybody’s Crazy. Whether you’ve got a story to share, or want guidance on how to navigate your crazy situation, hosts April McDaniel and Savannah James are here to answer your call-ins, lend their feedback, and share a little of their crazy too.
Everybody’s Crazy

Savannah James & April McDaniel
Better Half
From 9 to 5, one’s the boss; from 5 to 9, the other calls the shots. Together, Anastasia Karanikolaou – aka Stassiebaby – and Alexis Fisher create the perfect balance. Better Half is your backstage pass into the world of friendships, relationships, and the entertainment industry—where personal meets professional and chaos is part of the charm. They say opposites attract—these two are a beautifully unhinged recipe for something you won’t want to miss.
Better Half

Stassie Karanikolaou & Alexis Fisher
The Intersect
The Intersect is a new show about how technology, media, and culture are not just shaping our world—but more than ever, reconstructing our realities in real time. Join Cory Corrine, multiple Pulitzer Prize-winning journalist and media executive, in exploring the connections in the systems that are making us, in critical conversation with the people imagining what comes next.
The Intersect

Cory Corrine
No Guide For This
No Guide For This is a refreshing new podcast from Dear Media and The Bump that explores the uncharted territory between adulting and becoming a parent. Hosted by Jen Hayes Lee and Sasha Smith, this podcast taps into the heart of the transition from managing life as a grown-up to navigating the unpredictable world of parenting. Featuring insightful conversations with celebrity guests, the show blends humor, honesty, and relatable stories, giving listeners a sense of community during this pivotal life stage. Whether you're debating if you want kids at all or managing the juggle of multiple little ones, "No Guide For This" provides a candid look into how life, relationships, and identity shift when children enter the picture.
No Guide For This

Jen Hayes Lee and Sasha Smith
Live From Bed
Live From Bed is your official invitation to hide from the world with me — your permission slip to unravel out loud. Every Wednesday, I pull the covers over my head and drag my favorite people in with me — from internet sensations to experts — to celebrate our bad habits, worst traits, and the internal monologues that probably make both our therapists and the group chat nervous. We talk about the friendships that downgraded from ride-or-die to ‘hope you're well’, the plans we’re praying get canceled, the milestones we’re nowhere near — and the texts we wish we hadn’t sent. If your best friend’s ignoring your FaceTime… and you’ve already messed up one too many social interactions this week, this is your place. No unsolicited advice. No annoying success stories. Just the things we all think but wish someone else would say first — and a whole lot of commiserating.
Live From Bed

Jade Iovine
Come Together
Time to cut the cameras and turn ON the mic — Erin and Abe Lichy are pulling back the curtain on the wild ride of marriage, sex, business, and everything in between in Come Together. As a powerhouse couple who’ve built empires together—Erin as a serial entrepreneur, interior designer, and Real Housewives of New York star, and Abe as a sharp legal mind and founder of The Advisory—they’re the couple you want at your dinner party, the ones you want to grab a drink with, and the first ones you’ll turn to for advice. Each week, the duo will dive into the real, raw, and often unspoken realities of blending parenting, business, and love — all while keeping it real. With their signature honesty, wit, and easygoing vibe, they’re baring it all. Whether they’re talking business wins, how to keep the spark alive after nearly 15 years, or just the chaos of everyday life, no topic is off-limits. Tune in every Monday for the real secret behind what it really takes to Come Together.
Come Together

Erin and Abe Lichy
The Pre-Game with Kayla Nicole
Everyone knows the best part of any night out is the pre-game. You know the vibes – feels like a hype session in the bathroom mirror. From group chat debriefs to deep dives into the latest headlines (with a drink in hand, of course). The Pre-Game with Kayla Nicole is exactly that: the party before the party. Each week, we’re diving into all the things you and your homegirls actually talk about, from pop culture tea and beauty secrets to those ‘what would you do?’ scenarios that have you screaming at your phone. It’s unfiltered, hilarious, and has just the right amount of chaos, served with a splash of tequila and zero apologies. So grab your gloss, pour up, and let’s pre-game.
The Pre-Game with Kayla Nicole

Kayla Nicole
Audio thumbnail
How To Harness The Power Of Your Sexuality ft. GG Magree
00:00 / 49:29
Link copied to the clipboard!