It’s not every day you meet the man who defined the title – Chief of Stuff. At 30, Grant Gittlin has been in more rooms, worked with more high profile individuals, and fostered more deals than anyone his age. Five years ago, he embodied a role that had no description. Now he has forged a legacy that has helped many in the process.

Think of the Chief of Stuff as the ultimate apprentice. And for a company like MediaLink, the strategic advisory firm that helps facilitate partnerships between Silicon Valley, Madison Avenue, Hollywood, and Wall Street, the opportunity is game changing.

When encountering Grant, you’d never know he was the connected and influential man his current position – Chief Execution Officer suggests. With an infectious smile and radiant personality, Grant is a uniquely tenacious executive that honors friendship and community above all else.

MiLLENNiAL met up with Grant at his loft in Manhattan where we were welcomed into a bright, open, creative space eloquently reflective of the worldly experiences that fuel his vivacious spirit.

Life Before MediaLink

Raised in the Sunshine State of Florida, it’s naturally fitting that Grant would become a beacon of light. He attended Princeton University, where he majored in political science focusing on East Asian politics and Chinese. And while you’d think he’d be an all-star when it came to speaking Mandarin, Grant humorously informs us, “I’m the singular worst Chinese speaker you will ever meet.”

But as life would have it, Grant didn’t get into politics or even foreign affairs like his area of study would imply, he was recruited to work for a Connecticut based hedge fund straight out of college in 2007. Almost a foreshadowing of his life to come, the firm placed him in a program to analyze “how people thought about stuff.” The job certainly had its initial allure, but Grant quickly realized something wasn’t right. “I had seven bosses in 18 months,” he says.

The high executive turnover rate made him question his loyalty to the company. “To see them get fired one after another was very demoralizing. So it was time to leave.” With a newfound mission, he set out to find someone who made a living doing what they loved.

“I said I have one year to do this, and in one year I didn’t find anyone,” he laughs. Feeling slightly defeated as his 26^th birthday approached, Grant decided he would return to finance. It was during an interview with friend and investment banker, Alex Kassan, that Grant revealed his yearlong failed journey of finding someone who loved his or her profession.

Picking up on qualities that sounded familiar, Alex suggested Grant meet his father Michael Kassan, the CEO of MediaLink, to see if he could provide further direction.

Photo: Gareth Pon

The Meeting that Changed Grant Gittlin’s Life

Grant was being interviewed by Mr. Kassan to become an associate for MediaLink when, during a series of quick-witted banter, the idea to bring on an apprentice suddenly became an interesting thought.

Up to that point in his career, Kassan had fleetingly entertained the idea and he saw a quality in Grant that suggested it was time. He tells us, “It wasn’t something that was premeditated. It just happened.”

Kassan offered Grant the rare chance to become his “shadow” to which Grant agreed but not without first insisting on substantial responsibility. Grant explains, “The rule was: let me be empowered…let me speak with your authority so I can get stuff done and if it doesn’t work out you can fire me.” He stresses the importance and value of negotiation by using Carl Icahn’s famous words, “Don’t say no. Just ask for more.”

Kassan proudly states, “I gave him the stage to play on and he played the role brilliantly.”

Mastering the Art of Chief of Stuff

While attending the Network Upfronts – television’s biggest week to secure advertising for the upcoming season, Grant dove head first into his new role. Smiling, he reflects on an encounter with Ari Emmanuel, the agent made famous by Jeremy Pivens on HBO’s, Entourage. “I remember looking at Michael in the back of the car and I said ‘I know it’s only day one, but this is the most fun I have ever had.’” Little did he know, he would soon build a vital component to the MediaLink operation.

The Chief of Stuff is responsible for being the CEO’s right hand, in addition to acting as their eyes, ears and voice. Grant explains what exactly his job entailed. “Every person has things they need to do in their day. My job was to take as much of that stuff that was noncore to what Michael was good at and do it. And that can be everything.”

His daily tasks ranged from traveling to all events and business meetings and providing background information to better prepare for deal strategies to drafting prospective client follow up emails and offering insight into the next generation of innovators and successors.

Carefully distinguishing the difference between a Chief of Stuff and an assistant, Grant says the position is not to be placed in the urgent, but rather in the epicenter of the strategic development. He elaborates, “The problem with being an assistant is that you have to be so focused on managing the day to day that it’s really hard to elevate yourself and test how much of the person’s life you can accelerate.” He compares the exposure of being a Chief of Stuff to leasing someone’s life who is often decades ahead in terms of career, maturity, ability, network and sophistication.

The goal is to provide as much hands-on training as necessary to become an executive. Kassan describes the learning experience as the best MBA anyone could ever receive. “This was practical education in the field of play. And there is no substitute for that,” he adds.

Longtime friend of Kassan’s, Irwin Gotlieb, CEO of Group M, tells us, “We operate in a business where the schools don’t do a great job preparing someone for the kind of work we do. The only way a young person can come into the business and really learn is to work for the right boss.”

For Grant, being Kassan’s Chief of Stuff was like winning the professional lottery. Gotlieb further adds, “Mentorship isn’t a matter of learning from someone, it’s that they take a personal interest in your career and guide you.”

From Chief of Stuff to Chief Execution Officer

Grant’s role shifted into one that wasn’t directly connected to Kassan’s priorities. As the Chief Execution Officer, his day now consists of “business development” and identifying “the coolest companies and people in the world” to help “accelerate their business.”

He says, “I got really good at being the Chief of Stuff. And one of the things I’ve done since is codify it.” Grant has been asked countless times to help other executives find their own version. His one rule: “If the role touches scheduling, go find someone else.” Explaining his theory, he says, “Don’t take someone who can actually change your life from the aspect of what’s important, and put them in the urgent.”

One of Grant’s superpowers that helps his clients find what they are looking for is his innate ability to hear things others don’t. Spencer Lazar, Partner of General Catalyst, explains this unique quality. “What happens when you are able to listen very carefully is you start to get connections between unexpected things.” A professional web weaver, Grant often aligns businesses with people that can vastly benefit from working together.

Private equity investor, Leon Black, says he’s known Grant for years and “he’s always connecting people and driving growth.” His ability to leverage such abundant relationships is largely based on MediaLink’s core value: empowering others. Grant insists, “Friendship is the only variable that you can guarantee.”

With endearing and genuine excitement, Grant continues, “I only want to work with people I like. So I get to find them in the market and I get to hire people I love and respect at every level.” He credits Kassan for always surrounding himself with people he loves and says, “You don’t want to average down on your friends. You always want to be averaging up.”

Championing the NY Artist Community

Although he was empowered by his colleagues, Grant found he wasn’t nourishing his personal life. He was enthusiastic about art but didn’t know any artists. One night he met Evan Robarts, an artist working as a superintendent on the outskirts of East New York that painted in the basement because he couldn’t afford studio space.

What started as a heart to heart conversation launched into a network to discover and develop talent. Grant thought to gather a supportive community of art lovers to help pay for a studio where Robarts and his friends could freely create art. In exchange, the donors would receive select pieces. From that moment, ARTHA (pronounced “art-ah), an artist incubator, was born.

The program has since helped more than 14 artists accomplish their careers in the last four years. Grant explains the concept, “We find four to five artists a year and we give them space and we give them community and support and advice.”

Nicole Grammatico, ARTHA’s Director, adds, “Some artists are offered space within our residency program. Other artists are offered funding for special projects. These opportunities are tailor-made to the artist. One thing is for sure: once we decide to offer support, it is flexible and rapid!” The model of ARTHA is a cascading effect of how Grant handles all his interactions.

A man on the go with a heart that yearns to connect good people, Grant is constantly looking for ways to be of assistance. As Ross Levinsohn, former CEO of Yahoo and friend of the MediaLink family, says, “Grant has in many ways redefined what an apprenticeship can lead to…and has become one of the most dynamic guys in this space that I know.”

From working with disruptive and innovative entrepreneurs to transforming the lives of New York artists, Grant proves the door of opportunity can be unhinged if your willing to accept the challenges and share the rewards.