Founder Of StyleCaster, Ari Goldberg, Says 'Trust Your Gut'

by Peter Ryan

For entrepreneurs, the road to success is not all sunshine and rainbows. It’s a difficult journey, where only a few will reach their destination. In the end, those few will have struggled more than they have succeeded. Their success stems from four essential entrepreneurial ingredients: personality, environment, connections, and perseverance. It takes a special type of person to walk the road to success and Ari Goldberg is one of those people. He is the founder of a once emerging startup and now thriving company, StyleCaster.

Entrepreneurs aren’t made; they are born. As Goldberg explains, “It really is a personality type.” Being an entrepreneur seems to be not so much a choice as it is an expression of a person’s contempt for listening to someone else. “I have a real problem with authority and never wanted to work for anyone…it’s just not for me,” said Goldberg. The key part of an entrepreneur’s success is that they refuse to listen to anyone else, and thus, are more likely to continue their start-up while everyone is telling them to quit.

Confidence is key in turning a half-baked idea into profitable company. Some people who attempt the entrepreneurial lifestyle fail because they don’t have the confidence in their ideas to stick it out in the long-term. There just seems to be a fire in the belly of entrepreneurs, which allows them to burn through the challenges that come along with the title.

While being an entrepreneur is an innate personality type, there are lessons that must be learned. The environment is so important to shaping and teaching the entrepreneur. Goldberg educated himself at, and outside of, New York University. He recalls that what makes NYU special is that “the caliber of students and what you’re exposed to is just so good. I could never imagine going to school anywhere else. In retrospect, there’s no where else I would have applied.” NYU provides a stellar education and location, which seems to attract ambitious people. It seems to be that it is the culture of the city that contributes to an NYU student’s success.

Goldberg explains just what is so special about the city: ”We did an interview with CNBC, and I said ‘every American city has its own M.O. People go to Boston to be smart, people got to DC to be powerful, people go to LA to be famous…and people go to New York to compete.’ That’s the impetus for why people come here, and when you have 8 million people that are all here to be the best, that naturally is going to create a certain environment…The reason they are smack in the middle of Greenwich Village is because they know there is so much more to be exposed to.

Whether they’re interning, working, starting a business, or working at a non-profit, or doing research. They get to experience life while going to school.” This explanation of what makes the city tick is exactly why entrepreneurs come here. There is opportunity to compete against fellow ambitious people that provides lessons, as Goldberg says,

“They couldn’t teach me out of a textbook."

Some of those lessons are not found on the college campus, and students have to take on some unconventional roles. As Goldberg puts it,

“I was a scumbag club promoter, but I called it strategic marketing and branding.”

One might think that club promoting would be a distraction on the path to success, but Goldberg contends that his time spent promoting was fundamental to him later in life. One of those fundamentals was “how to sit down in a negotiation with a guy you’re really afraid of and not sweat.”

Goldberg says, “There’s little things you have to learn from experience…But I think one of the most valuable lessons that I learned that served me very well in my career…in the club especially when somebody influential walks in you have five minutes max to build a relationship, to build a rapport, and build trust with them. It’s funny, a lot of times in business you get one shot and it’s fast. You’re with the CEO of XYZ agency, and you get two minutes. How do you build a rapport where you trust them and they trust you, they like you or whatever it might be? That was definitely one of many things I learned at a nightclub."

The nightclub is not just a place where a ‘scumbag’ goes to party, but also where he goes to learn about the business world. Actively dealing with people in a professional fashion allows for young entrepreneurs to figure out what works and what doesn’t. The main point isn’t that he was a club promoter, it’s that he was in an environment that allowed him to learn key lessons.

“The ability to make those mistakes at 19, rather than 30, is a huge benefit. When you’re younger, problems and consequences are smaller, but as you grow, so does the size of those problems and consequences. At a certain point, however, it’s time to leave the club promoting behind and move on to better and bigger things.”

Goldberg says, “When I was 22, I just graduated and my dad was like ‘this whole club promoting thing is cool, but you need to leverage it for something else’.” He was still in need of experience and settling for just any job wasn’t going to do. This is when Goldberg learned the value of the right connections. He said,

“I thought that, if I’m going to go to work for someone, I want to work for the guy that understands entertainment, understands sports, understands music, understands branding, and brings all those things together.” That guy was Steve Stout.

Stout was the founder and CEO of Translation, an advertising agency that has had much success in all those industries. Goldberg was able gain insights into the marketing and business world with the guidance of “Steve, who is obviously a genius. But even with that, [he] left after six months because [again, he doesn’t] like working for anybody.”

At this phase in Goldberg’s life, he began honing in on creating his startup. He began working with a couple of co-founders incubating the idea of StyleCaster. Goldberg, brother David, and their friend, Brandon, were all out to dinner one night, about to head to a nightclub, when Brandon suggested, “I’ve had this idea for a while.

Everybody, when they wake up in the morning, [asks the same two questions]. What’s the temperature? What do I wear? Everybody uses AccuWeather,, and WeatherBug. Everybody gives you the weather, and no one gives you outfit recommendations.” This simple dinner conversation with a few peers led to the budding creation of StyleCaster.

During the same period, Lebron James approached Goldberg, asking him to work for him. He reminisces,

“Ever since I could walk, all I wanted to do was represent the greatest athlete in the world, and everybody told me ‘there’s 10 million Jewish kids that want to do that, nobody gets to do that, you’ll never do that.’ Then at 25, I had that job, and it was…awesome. Through Lebron, I was introduced to Dan Gilbert.”

At the time, Gilbert was the founder of Quicken Loans and owner of the Cleveland Cavaliers. While working for Lebron was his dream job, Goldberg knew it wouldn’t last because what he “loved was startups.”

The connection to Gilbert through Lebron, however, was an instrumental part in launching StyleCaster, since Gilbert was one of the first initial investors. Gilbert was a mentor that, as Goldberg says, “Put up a lot of the capital and taught us a lot about being executives, being an entrepreneur, being a founder and running a business.”

Gaining success is not an instant process; it takes time to acquire all the necessary skills, capital and connections. The fact that Goldberg placed himself in environment, which held the potential to connect with influential people like James and Gilbert, is a key part of why StyleCaster has done so well. An entrepreneur doesn’t always have to come flying out of the gate to launch their idea because most times, they end up failing. While aggressiveness is important, the ability to reserve oneself to strike at the right moment is also critical.

Goldberg was now fully committed to his startup. Initially, financing was strenuous, since the co-founders “didn’t have two nickels to rub together,” so the financial support from Gilbert was essential for helping StyleCaster to get off the ground. Once Goldberg got the money, he had to figure out how to break into the fashion industry. This seemed like a daunting feat, but what Goldberg contends is that “we’re not ‘in’ the fashion business…we run a digital media company…it just so happens that the context is fashion.”

StyleCaster is about bringing “style to the people” through content that assists “people [who] need information, need products, or need technologies that make their style life better.” StyleCaster offers a few sections of its site to their other properties to target multiple markets. “StyleCaster Media Group is the flagship property. StyleCaster, Beauty High, The Vivant, and Daily Makeover are all these properties that we drop out. That’s why a lot of times we will refer to ourselves as the Condé Nast of the 21st century.”

Adversity is an obstacle that all entrepreneurs will face, and it is perseverance that allows them to be successful. The big names in fashion publishing, like Condé Nast, represent that obstacle for a small startup like StyleCaster, however, Goldberg has always “believed in the David and Goliath theory.” He thinks that, even though “they’ve been putting content out for years, [they’re] making a better, faster, cheaper mousetrap and that’s hopefully what will drive the business.”

The importance of learning how to enter the industry is incredible for any entrepreneur. Although a company seems to have a monopoly, it is possible for an entrepreneur to find their weakness and exploit it. The fashion publication industry’s big weakness, Goldberg says, is that “people are sick of Anna Wintour dictating what fashion is to them. Social and digital has leveled the playing field.”

StyleCaster’s humble goal for the future is “media domination."

Goldberg says, “Our plan is to continue to grow revenues, continue to scale the business, continue to increase our audience reach. Really, the primary focus right now is on our makeover solutions technology platform. Really distributing that into 20,000 sites across the world. So everybody is using that technology, and then just keep staying true to Style to the People.” There is a lot of potential for StyleCaster that involves some challenges ahead, but as Goldberg says, “As long as you know what your mission is and what your vision is, there’s going to be ups and downs and bumps along the way, but you just got to keep at it.”

The lesson of just keeping at it is valuable for young entrepreneurs trying to find the path to success at NYU. In order to have that sort of commitment to a startup or idea, Goldberg suggests, “You’ve got to find something that you are so passionate about, that on the worst days, you’ll still go do it.” That passion will be the driving force behind the agonizing pursuit of success for your startup.

Goldberg advises, “If you don’t think about quitting everyday, you’re not going hard enough. There were times when I just looked at the guys and was like, ‘I’m done, I don’t want to; I can’t. I physically, mentally, psychologically can’t take this anymore.’ You know you have to have a partner.” The value of having a partner, who’s experiencing the same difficulties as you, is essential to such a high-risk endeavor. At the end of the day, however, the only person that can tell if the idea is worthy of all your time and energy is you.

That person has to have an unrelenting personality, which allows them to persevere through the hard times, as well as the ability to take advantage of their environment and the network of people that comes with it. Although it seems to be nerve-racking, Goldberg’s primary advice for a young college student thinking about jumping into the startup world is to “trust your gut.”

Photos via StyleCaster