Hilarious and enterprising millennials have managed to transform their social media fame into a substantial living.

There’s no denying that millennials have something to say when it comes to conquering social media, and a select few have cracked the marketing code. As cool as it may look, it’s not all fun and games—there’s a lot of hard work, dedication, and finding just the right voice that works. We spoke with some of the hottest ‘grammars today—Steffy’s Pros and Cons, Girl With No Job, and The Fat Jewish—to get the inside scoop on their journeys from anonymity to social media celebrity.

The Fat Jewish

Josh Ostrovsky, a.k.a. thefatjewish never had a lifelong dream to be a comedian, nor did he ever think he’d become a social media mogul and socialite. “My first job was at a pet store in Manhattan called Pet Land where I also sold pot,” Ostrovsky said. “And I had this genius idea that if people wanted to buy pot from me, they’d also have to buy something from Pet Land. So people who didn’t have pets had to walk out with a dog bone or a parakeet swing. Needless to say, my sales were incredible.”

Instagram User Josh Ostrovsky

Josh Ostrovsky

Ostrovsky is equal parts humorist and entrepreneur.

Fast forward to 2016 and Ostrovsky has an Instagram account with 8.9 million followers and counting. Not one to just sit back and chill, in the last few years he’s gone on to start businesses, pen articles, become a plus-sized model, and much more. Despite his fame and fans like Katy Perry and Snoop Dogg, he manages to stay surprisingly humble.

“I think I’m willing to say things that other people aren’t and that’s because I paved my own way professionally. I’m not beholden to anybody,” Ostrovsky said. “I just drove across the country reviewing the food at strip clubs, and that’s going to be in a traditionally very conservative food magazine. The point is, I don’t work for anybody and people can either like it or not.”

Love him or hate him, there’s no denying that Ostrovsky is a shrewd businessman. The idea to start his company, White Girl Rosé in 2015, came about after he realized that while many people loved the drink, nobody could name a brand. “I love the high end of wine, but nobody ever explored the other side, which is that wine can be really fun,” said Ostrovsky. “You can drink it right out of the bottle and there can be a lower-brow version.”

But it’s not all about fun, easy-breezy booze parties for Ostrovsky. In 2015, he came out with a collection of humorous essays and pictures, Money Pizza Respect. Originally, he wanted to write an erotica book but his publishers didn’t think the timing was right. “I still want to write a whole novel of erotica,” said Ostrovsky. “The cover would be a woman standing on a cliff and then a man desperately tearing at her shirt and I want it to be called something like Passion Cove.”

Instagram Josh Ostrovsky

Josh Ostrovsky Book

Another interest for Ostrovsky is the fashion world, and in 2015 he made waves by curating “Dad Season” for New York Fashion Week.

“Dads have the absolute best style and everyone wants to look like they’re putting in minimal effort, right?” asked Ostrovsky. “Also fashion week is super non-inclusive, so I used actual dads that I found on Craigslist, and a lot of these guys had never been to fashion week or didn’t even know what it was, so it was cool to bring some new blood into that.”

With so much accomplished in so little time, it’s hard to predict what’s next for a man who bases his celebrity on being unpredictable. But without much prompting, he’s willing to offer insight into his ultimate goal in life:

“The dream for me is to get to the pinnacle of fame and then right when things are really at their loudest point, I want to just disappear,” said Ostrovsky. “Basically I want two or three years where nobody knows where I am and then somebody goes to a girls junior basketball game in Baltimore, and I’ve cut my hair and look totally different. And I just gave it all up for no reason, because none of it matters.”

How To Get More Followers On the Gram

Want to become an IG celebrity or simply gain some more fans? We asked for tips from the pros to help you achieve the ultimate level of fame.

Thefatjewish: “Once social media started being a platform and I could show my life to people, I was basically doing the same shit I was doing before, but now with a much larger audience. I’m not a comedian, I just want people to be completely confused and I want them to be talking. It’s all about conversation.”

GirlWithNoJob: “Know your followers. Who are they? What do they like? What don’t they like? Put content out and see what works. Then do more of that. Cater to your audience, because at the end of the day, you’re a caterer.”

SteffyspandCS: “The first and most important tip is to invest in a good camera and a good photographer. Quality images win people over. Also make sure not to post too frequently and be strategic about when you post—figure out what times work best, what hashtags work best, and what photos are the most liked by followers. It’s also important to develop a look and feel for your feed so there is consistency in all of your posts.”

Girl With No Job

On the opposite end of the spectrum, Girl With No Job a.k.a. Claudia Oshry prides herself on not having a job and not wanting one, even though that’s kind of her job. The idea for GWNJ started when she was in college as a Tumblr page originally called Girl With A Job, which she treated as a diary to pour out her frustrations and complaints about her first internship in PR.

Claudia Oshry Merchandise“It was horrendous, everyone was mean to me and I was treated like, well, a typical intern,” said Oshry. “I was eventually fired and changed the name of the blog to Girl With No Job—for accuracy purposes. I was drawn to Instagram as a platform to grow my brand and draw people to the blog. Little did I know that the Instagram would become my brand.”

The sass and personality that GWNJ brings to Instagram has made her extremely popular with over two million followers. From Instagram she’s also branched out and now has her own app, which is available for free on iTunes. For those who want to know what she’s up to, or her thoughts on the latest episode of Real Housewives, it’s all in one place. With social media, apps, and blogs covered, what could a woman without a job want to do next?

“The fun (and scary) thing about the digital space is that it’s so unpredictable,” she said. “Instagram just released stories and kind of rerouted my entire career plan. I really can’t plan for the future so I prefer to just fly by the seat of my pants.”

Steffy’s Pros and Cons

It started in 2011 as a way to sell vintage pieces on a blog to pay the rent while she was in fashion school in Miami. But in a few short years Steffy Degreff has managed to amass over 100,000 followers and expand her blog into so much more than fashion.

“When IG was released most bloggers began to use it, so I jumped on the bandwagon,” said Degreff. “I always loved how visual the platform was, and the emphasis on good photography really forced every blogger (myself included) to learn photography and improve their photos.”

Steffy Degreff

Steffys Starter Home

Steffy’s starter home became the center of her digital presence.

While she still has a soft spot for fashion blogging, after a few years she felt like the market had become oversaturated and looked for a way to diversify and incorporate other interests in her life and blog.

“I wanted a new way to differentiate myself,” Degreff said. “Also, my husband and I bought our first home, a fixer-upper, so including home renovation and design projects made a lot of sense. My blog has grown as I have grown, and as I get older and my interests shift, the things I blog about have also shifted.”

Part of the allure of Steffy’s Pros and Cons is the fact that she maintains a woman-next-door vibe—that she seems like someone who’s living life, growing, and exploring the world around her without the pomp and showiness of some bloggers.

“I’ve tried to keep myself grounded, and like many of my followers, I work a full-time job and lead a pretty normal life,” Degreff said. “I keep them in the loop about what is going on in my life and I try to remain pretty honest and transparent.”

[©Image 1 & 2 courtesy of Josh Ostrovsky, Image 3 courtesy of Brandon Andre, Image 4 courtesy of Claudia Oshry, Image 5 & 6 courtesy of Steffy Degreff]

Download Port Shopping Guide App
To Start Planning Your Port Shopping Experience

Get the Mobile App Now!

Royal Caribbean International's Port & Shopping Guide

Make the most of every moment of your cruise vacation with the official iPad edition. Exciting features and video extras to infuse your vacation with even more WOWs.

Download for Free