My Biggest Lesson: Michael Jacobson

As senior vice president, Michael leads the US team of ITB Worldwide to build impactful celebrity and influencer driven programs on behalf of brands, agencies and non-profits. With nearly 20 years of expertise in the Octagon Sports and Entertainment Network - partnering with all types of talent for all types of programs - he is a first mover in the space and has deep relationships across entertainment, sports, lifestyle and music sectors which enable him to deliver culturally defining campaigns. 

Is it cheating if I say two? There are two lessons I learned pretty early on in my career as an intern at Octagon, which feels like forever ago now: ‘Family first’ and ‘Be curious’. 

The first was a reminder to balance priorities in life; it wasn’t just about family but about having balance. The second was to ask questions and a reminder that there’s no fear in asking questions – even if it means that people are going to think you don’t know what you’re talking about. 

I was 22, I had just come from working as an intern at the US Embassy in the Bahamas and going through a transition from completely unrelated experience and background in school to a sports marketing internship at Octagon. It was in the Washington DC office where I got my bones and training in sports and entertainment marketing for my first few years. For the first three years everything was being learned and that was both exciting and challenging (in a good way). 

Both of these lessons were learned during this period at Octagon. There I was, 22 years old coming in bright eyed and bushy tailed and really not knowing the space of sports and entertainment marketing.

To this day, this person probably doesn’t even know that he ever gave me this advice, but I remember walking into his office to talk to him one day and he had this hit list of top five or 10 things to talk about which was printed out and attached to a corkboard next to his chair. At the top of this list was ‘Family first’ – but it wasn’t just about family, it was to know your priorities in life and how to balance them. 

The lesson on curiosity came through another VP in the network at the time. Very specifically, it was to ask questions. He was always questioning everything – to the point where you would sometimes question why he can’t just accept how life is rather than having to know how everything works. I don’t think I’ve ever met anyone who was quite as naturally curious at deconstructing the world. 

‘Family first’ came from Bill Hart (now Vice President, Sales at Worldwide Speakers Group). He’d been in the sports marketing business maybe 20-30 years at that point when I was just starting out.

‘Be curious’ came from Patrick McGee (now President at ProVentures) – the first person who hired me entry level. He was the most curious businessperson I’d ever met. The way he interrogated and thought about problems, opportunities and solutions was really different, and it was very simple. He just wanted to break it down into the smallest possible pieces; because solutions and opportunities usually are pretty simple, when you finally figured out the basic truth to whatever was going on. 

Having Patrick’s honest, childlike curiosity was really refreshing. In an industry like sports marketing, there was much more of a locker room feel and coach mentality, where you are instructing players about how you do things and, whatever it was, it was this refreshing honesty of someone very senior and very successful saying, I really don’t know and wanting to go and figure it out. The advice was really instructive and has been with me throughout my whole career.

From both of them, there was a lot of empathy and compassion. And I think what they both represented was different than the industry at large and quite honestly why Octagon have been so sticky for me in the long term. I’ve long said it’s the least Hollywood agency in Hollywood. And the kind of DNA of the people that have populated it are smart, creative, incredibly bright solution-oriented folks who, for whatever reason, aren’t falling into the traps of the sexiness, flash and glamour that’s associated with sports entertainment in a negative way – but using that smartly to their advantage. 

I think everybody has these parts of curiosity and interest or ways in which they prioritise what they want in life. It’s important to them and how they go about getting it. It’s easier to follow paths that are evident to you than those that are a mystery and being able to see lots of different examples of people of success that were around me allowed these different ways. It wasn’t just about family, but it was not just sticking to the normal of coming into the shop and doing this one thing but being able to evolve out of it. That’s actually something David Schwab (Vice President at Octagon) was and still is tremendous at: see a different opportunity and go seek it, go try something. That mentality has given me the opportunity in 2007 to go create this, to grow our business from talent to influencer; and that has been super impactful. 

I’ve actually been lucky enough to have a lot of fantastic mentors who provided value so I would really be remiss if I didn’t mention two other folks who early in my career had a big impact and, unsurprisingly, both of them and I had a lot of depth of conversation with early on – Phil de Picciotto (Founder and President of Octagon) and Drew Johnson (Director, Strategic Communications at Octagon). Again, the overarching semantic that I really benefited from was teaching, which was reflected in the umbrella environment which was always about helping others as much as yourself.  

The ‘family first’ mantra wasn’t something I was in the right place for at the time. I was burning the candle at all hours, extending myself to all end, really having no personal life of consequence. A couple of years later, and at the family place I’m at now, knowing that this could be a direction I’d want to take, it was about having someone there to prove it could be attainable to find the right balance. 

It wasn’t something where I was like, oh yeah, I’ve always wanted to start a family. But now look at me – married with three kids – and I think my commitment to that lesson is evidenced by the fact that I’m answering these questions while in the middle of the school carpool run at this very moment.   

At its most basic, we talk a lot about being curious as the DNA of what ITB Worldwide is. Everybody and everything changes, and we don’t have the same individuals from a year ago, five or 10 years ago, but I think we’ve found some commonalities of this being an ethos; one that I very much relate to from a personal experience and have helped champion. I do share that indirectly and directly with the team and then on a one-to-one level, the idea of understanding what you want as an individual – before you even get to putting your professional hat on. One of the toughest things in the world is figuring out who you are and what you want. But exposing yourself more and more to others can give you good things to emulate and make a big difference in helping you moved forward.