Josh Ostrovsky: How Has He Built His Empire?

Josh Ostrovsky aka The Fat Jewish on social media, is one of the first people to learn how to monetize social media and turn it into a business platform to promote and create new products. From gaining millions of fans worldwide, to writing, acting, hosting and creating and selling his own wine company, @thefatjewish has created an empire for himself and team, and shown the world that being a successful entrepreneur can happen if you stand by your gut and follow your own path forward!


How did you start in the social media industry? What was your career plan at the beginning?
My original plan was to become an endodontic surgeon, which focuses on tooth roots, and I attended University of Michigan dental school for 2 years… Joking! OMG that would be so weird. No, but seriously, before social media I was a writer and television personality, and got my start on the E! Channel on a show called “The Daily 10” where I interviewed C-list celebrities and covered red carpets wearing an adult diaper or some equally shocking outfit. Me and my current business partner were also writing partners at that time, we sold shows to Amazon, FX, and a couple others, but they never went anywhere. I was also in a rap group called “Team Facelift,” we had a record deal and went on tour. I tried to stage dive once in Europe but was too fat and got dropped.

You were one of the first Instagram megastars and you have now more than 10 millions followers. Did you have any particular strategy when you decided to open an account on Instagram?
Initially my Instagram account was just for the entertainment of my idiotic friends. I’m one of those people that has the same friends from high school. We still have sleepovers in our 30’s and eat ice cream for dinner. NO PARENTS! There was never a business plan, when I joined Instagram nobody had figured out how to monetize the platform (besides our digital overlord Mark Zuckerberg obviously), so it was just people posting dumb stuff for their friends and stalking their exes. It was a world without influencers. I built my platform by being willing to “take it there,” I’ll say exactly what you’re thinking but are too afraid to say out loud.

Where did you get your sense of humor?
I was always the type of guy who would do anything for a laugh, partially to mask my deep seated massive insecurities and partially because making people laugh is really fun. I would draw a penis on the face of a sleeping baby if I thought people would laugh, nothing is sacred. Also, my mom once slept with Tim Allen in the late 1970’s, so maybe he’s actually my dad and funny is in my genes? In terms of what I post on social media, there’s no science. A lot of “funny” Instagram accounts have teams of people in offices quietly working on computers looking for / creating content, it’s a business. My account is always me, probably tipsy off rosé at lunch with my mom and one of her friends with expensive plastic surgery, posting something that a teenager in Wisconsin DM’ed to me. I’m still having fun with it.

We still have sleepovers in our 30’s & eat ice cream for dinner. No parents!

What are the factors that make you say ‘yes’ to work with a brand and the factors that make you say ‘no’?
A lot of brands love to pretend that they are super down and tell me that they want to partner because I say and do wild stuff. They’re like “We’re disruptive! We’re authentic! DO WHATEVER YOU WANT!” and then I send them three ideas of what I might post and they’re like “The legal department is freaking out, you absolutely cannot do that.” They all want to make noise and do edgy stuff that will cut through all the noise on the internet and actually resonate with people, but they are scared to actually do anything edgy or different. That’s why I started my own brand and stopped working them. Byeeeeee.

You are also a serial entrepreneur. One of your biggest business is Babe (@drinkbabe). Tell us a little bit about your brand. What’s the story and how did you start?
As my audience grew and I developed an intimate relationship with them (I answer every single DM), I started talking to them about what they would want if I were to produce a consumer product. At that time (2015), everyone was talking about rosé, and how they wanted it to be portable, inclusive and actually fun. Wine was mostly catering to the high-end (or aspiring to be) crowd, who is swirling their wine around and talking about it’s notes of leather and apricot. My audience was drinking a ton of wine, but they didn’t know the same of a single brand. Wine felt dusty, it felt old. So we put it in a can with a bold and iconic label, with bubbles, and made juice that tastes good and will get you drunk so you wake up in some shrubs near your house. Safely and responsibly of course. It was a reverse engineer, by building an audience and actually asking what they wanted, then giving it to them, it eliminated all the guesswork. When it hit the shelves, people went wild for it, because they had told us to make it. I’m not a wine guy, I’m more of a trashy domestic beer guy, but I made wine because it’s what my followers wanted.

My mom once slept with Tim Allen in the late 1970’s, so maybe he’s actually my dad and funny is in my genes?

What has been your favorite part of creating Babe Drink?
Building a brand from the ground up has certainly been a learning experience. And by “learning experience” I mean a garbage fire nightmare that in the end was super fulfilling. A lot of people only see the end result on Instagram (me pouring rosé on myself in a kiddie pool) which is the product of a ton of hard work distilled down to a single image. They don’t see the horrendous meetings at 7AM in Phoenix where I’m trying to teach middle aged men who work at alcohol distribution companies that you can sell wine by promoting it on Instagram. Like they actually didn’t know that was a thing before I told them. But one of my favorite parts of the entire experience has been talking to people about how to actually start a brand and be your own boss. The Internet has created a generation of young entrepreneurs and thinkers that are superior to any of their predecessors. Unfortunately, many of them have bought into the false narrative that the Internet creates (I can be the CEO of a startup that makes edible socks! Just start an Instagram account for it and get rich!), and while I support them in following their dreams and passions, there is some confusion these days about how things actually get done. The instant gratification of social media and e-commerce has created the illusion that everything they see on the Internet just happens. So I’m trying to help them understand how to harness it properly, how to lay foundation in order to build something real and something lasting.

How do you organize yourself to manage your businesses and stay productive on Instagram?

While I may be wearing assless leather chaps and saying outrageous things, it’s all highly organized and focused, and requires a ton of planning. I have an incredible team around me who keeps me focused and inspired, and I make sure to get a lot of sleep. It’s so lame and not metal to say that, but you’re just not going to do good things if you’re tired. If you want to party hard, just start doing drugs at dusk and be passed out by 11PM, you’ll wake up (sort of) refreshed.

How does a day in your life look like?
Work, work, work, message J-Lo on Instagram and tell her I would take a shot of her butt sweat (she never responds), have a heterosexual sleepover with adult men and watch weird videos on the Internet, go to sleep, wake up and start working again.

Do you feel your journey has been influenced, positively or negatively, by choosing “The Fat Jewish” as your nickname?
It’s been extremely positive. Obviously I get insane messages on the internet where people tell me that Hitler had some “good ideas,” but mostly it’s been amazing. I have kids tell me stories all the time about living in Iowa where there are no Jews and how I made being Jewish cool at their school. I like that a lot.

Do you have any thoughts about what might happen in the next phase of your career?
We sold BABE to Anheuser Busch, it was their largest non-beer acquisition ever, and I’m so excited to make it available absolutely everywhere. When people are in Japan drinking the wine and making questionable sexual decisions, my job will finally be done. After that? No idea, I’m making it up as I go. Whoever is reading this interview should message me on Instagram and pitch me an idea. I’m down for WHATEVER… Read More



Entrepreneur Mindset magazine Fall 2019 featuring Josh Ostrovsky, Tanoa Tales, Lauren Shirreffs, Kelli Gautreau, Kail Walker, Ryan Laverty & Sal Campisi for Vide etc…

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