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Why Mentoring Matters Monday Night & Every Night
Jabari Hearn, SVP of Marketing & Entertainment at Westbrook Media

As a kid growing up in Chicago, Jabari Hearn dreamed of creating Nike commercials — ones that could rival the icon spots the brand produced with Michael Jordan, his childhood idol. Years later, Hearn would get that chance when he started working for Nike in senior-level marketing roles. Hearn, now SVP of Marketing and Entertainment at Westbrook Media, says the guidance of a mentor, a fellow Black executive at the company, was a turning point in his career. The relationship helped him excel. Now, he’s giving back to other marketers of color through Monday Night Mentorship, a membership network and career accelerant for marketers of color co-founded by Hearn. In this episode, Hearn shares the key things mentors and mentees must do to get the most out of their relationship, and how organizations can use mentorship to transform DEI (Diversity, Equity and Inclusion) into DIME (Diversity, Inclusion, Mentorship, and Equity).

Jabari Hearn, SVP of Marketing & Entertainment at Westbrook Media

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Show Notes

Samir Bakhru:

Welcome to the Future Fountain, a podcast series dedicated to conversations about the tech ecosystem. Brought to you by Orrick and the NYU Future Labs. I’m Samir Bakhru and we are thrilled to have as our guest today Jabari Hearn, who is the senior vice president of marketing and entertainment of Westbrook Media and a revolutionary marketer. The topic of today’s conversation is mentorship, and Jabari has recently founded a new organization call Monday Night Mentorship, whose mission is to accelerate the advancement and impact of marketers of color. Jabari, welcome. Thank you for joining us. We’re super excited to have you, so let’s dive in. I think first and foremost, please tell us about your career path. Where did you start? How did you end up at Westbrook working with Will and Jada Pinkett-Smith?

Jabari Hearn:

Right on. I’ve been doing this for a little while – I think now 26 years, so a fairly long career path, and I’ll try to not bore everyone to tears with it. But I’m just an only child from Chicago who modeled himself after Michael Jordan like probably every young Black kid in Chicago, probably every kid in Chicago, during the Michael Jordan time.

Samir:

Every kid everywhere. {Laughter}

Jabari:

Exactly. I always envisioned myself doing Nike commercials. I loved seeing Michael Jordan float through the air. The energy, the emotion that they put into the storytelling just really swept me up as a kid. And as a young kid in Chicago, that came to life also through posters. You know, I had my every part of my bedroom filled with Nike posters and Michael Jordan posters, so I was surrounded by the world of advertising really, really early on and in love with it. And so when I got the chance to get a basketball scholarship to Southern Methodist, I knew that my degree was going to be in advertising. So I left SMU. Unfortunately, not a great basketball career, but did have a...

Samir:

Made it farther than most of us. {Laughter}

Jabari:

Very true, I can’t complain. I didn’t have to pay for school, but definitely left with some great memories and a degree in advertising, which propelled me right into the advertising industry. And, at that time, being the only African American around town was a benefit to me. One of my first calls was from Wieden+Kennedy in Portland, Oregon, and they were looking for somebody who understood youth culture, who understood basketball, and who understood advertising. And youth culture at that time was really transforming into – it was really Black culture that was really taking over, urban culture that was really taking over. So I was able to have a unique perspective in the all-white ad agencies, these all sort of middle-aged white male agencies, because brands were trying to talk to this newfound audience, and so…

Samir:

Right. They were changing, right? It was pretty...

Jabari:

Exactly. I was smack dab in the middle of that transition. I was able to take advantage of it and spent 10 years in the advertising world, and my super power was really understanding youth and urban culture and bringing that to the table and showing them how they can take advantage of that, in a sense, creatively. After doing that for 10 years, I’m like, alright, I want to get over into the brands side of things.

Jabari:

Advertising, you know, you think that’s your whole world until you go onto the brands side and you realize there’s so much more to marketing or storytelling, or even launching a product than just its advertising. And when I first got to Nike, which was a dream job, I got advice to say, you know, learn how this place, you know, works. Learn how it creates value for customers and for shareholders. And that took me a decade. I started in a global function on consumer insights, which was always going to be my foundation, really understanding the consumer, went into a global marketing role, then a North America role, and then literally down into the city role in Los Angeles, where I was the marketing director of Nike West only. And it took me a decade to really see the company from all those angles. At that point I knew I wanted to diversify.

Jabari:

I did some amazing work at Nike, from launching the NFL to the launching inequality campaign, which was a massive one, and working on basketball to working on the Nike Women’s Half Marathon in San Francisco, as an example.

Samir:

These are a lot of cool initiatives; I just have to pause for a second. What was one of your favorite products or initiatives to work on at Nike? That’s such a unique experience, right?

Jabari:

Yes. When I got to Nike, I worked on football, men’s training, I worked on tennis for a while. And the last job that I got—it was my last year at Nike after being there a decade—they offered me the Nike Basketball job. Of course, being a basketball guy from Chicago, that was a dream for me. The best part about it is that they leveraged basketball to make much bigger conversations. So, when I worked there, it was the time of killings happening in the Black neighborhood. Treyvon Martin was at the time. And so we were able to use the NBA All Star game in New Orleans to not just launch basketball products in conversations, but to talk at a much higher brand level. And that campaign we did was called the Nike Equality Campaign. Which basically talked about, why couldn’t the world behave very much like it does in sports, in between the sport confines and lines? We look at somebody like Lebron James a lot differently than we look at him if he’s walking down the alley at midnight. And so it was one of the most impactful campaigns I’ve ever worked on in my career, and it was a great way to end my time at Nike.

Samir:

That’s amazing. And then you went to helping Google sell software, right?

Jabari:

Yes. Then I had to diversify, right?

Samir:

Right.

Jabari:

I mean I’m a big 6’5” basketball player, Black male, bald head. When I walk onto a plane, people are like, “You play basketball, right?” And so, I had to get away from that. I wanted to diversify and make sure people could understand that I do more than just sports. I am more than just sports. And I wanted to take what I learned there and transfer it into the consumer electronics space, where you still are trying to build an irrational love towards, say, your phone.

Samir:

Right. Makes perfect sense. So how did you get from there and working at Lyft to now, back into a media executive role? What led you to that path?

Jabari:

I’ve always approached my career where I wanted to add tools to my toolbelt.

Samir:

Always learning.

Jabari:

But there comes a time when your belt is full of tools and you have to sort of understand what your superpower is. Felt like I gone and explored, you know, Silicon Valley. I’ve gone to really work on a consumer electrics area at Google. And then on, you know, software as a service in a sense from Lyft. And I wanted to get back into my wheelhouse. My strength. My passion. Which is storytelling, creativity, youthfulness, culture. I wanted to be in a place that was diverse and I felt at home, and that was entertainment, brand and talent marketing, which I’m doing now at Westbrook Media.

Samir:

Makes perfect sense. I mean, you’ve had such a diversity of experience, working from a sports company to working for a software company, ridesharing, back into global media. I’d be curious to hear who some of your mentors were along the way and how they made a difference in your career, especially at those pivotal transitional points, where you went from doing something completely different in a completely different industry.

Jabari:

Totally. You know, I had never – other than the usual suspects, like your parents – I had never had a mentor. I’ve had people that looked out for me. I’ve had people that give me direction and guidance and support. You couldn’t get anywhere without that. But I never understood what a mentor was until I got to Nike. And I remember seeing a gentleman on stage, who was the GM of the Olympics at the time, a Black male, bald head like me, tall, athletic, he played basketball. And he was on stage at Nike in this tailored suit, talking about how he was going to bring the Olympics to this new level. And I had never seen anything like that before. I’d never had a Black boss. I’d never seen a Black male more senior than me that captivated me the way this man did, and his name was Kris Aman. He was the VP GM of the Olympics at the time at Nike. And I reached out to him immediately. I said, I have to know this person, I have to talk to him. His energy, his vision. And immediately, he did not know me from Adam, but he responded to my email and said, “Come see me.” Opened up his door and literally said “How can I help you?” And from that day I would go into his office every month and be like, “Hey,” just to check in, share my experiences. He would give me the most amazing advice; help me through what I was doing that nobody else actually gave to me. Nobody else would spend that much time with me. Not even my boss at Nike gave me as much facetime as this person, Kris Aman, did. And that sent me on a path of really understanding how to use a mentor, what a mentor is, and how I can also be that to others.

Samir:

One of the things that you said is so critical that gets missed is that first step that you took of just having that initiative and not being afraid to ping him and say “Hey, I’d like to get to know you. I think we might be able to have an interesting conversation and I can learn from you.” As a person of color myself, that’s something that just goes missed, and young professionals don’t do that and they end up missing out on a lifetime of opportunity because they just didn’t send that one email.

Jabari:

Exactly. Funny thing is, Kris, at that moment when I reached out to him, told me very specifically, he said “You know what? In every big forum, I ask people to reach out to me, that my door is open.” And he said 99[%] of the people that do are people that are not of color.

Samir:

Right.

Jabari:

He said, “I don’t know what it is, but the Black people will not reach out to me.” And I’ve also found the same thing.

Samir:

Some of us, like in these organizations, we don’t want to get noticed sometimes because we’re afraid of what the repercussions might be, right? But I think in today’s world it’s about stepping outside that box and saying, “Okay, I have to take that initiative.”

Jabari:

Absolutely. If I didn’t take that initiative to reach out, I don’t know where I’d be today.

Samir:

I know we want to talk about Monday Night Mentorship because I know you are excited to talk about that. But first, I think we do want to start with one question. You talked a little bit about brands. Because you’re a marketing executive, and have been for a long time, we want to get your insight on brands. And in the age of stakeholder capitalism, it’s a term that gets thrown around a lot today. Whether its BlackRock or others that are talking about it and the shift in thinking of the stakeholder capitalism. From a marketer’s perspective, how is DEI showing up differently as a branding consideration?

Jabari:

I think DEI is like maturity. People are at different stages of development there, in where they are, how they understand it and how they are implementing it into their organization. But I think it’s really difficult for organizations because a lot of them are starting from ground zero. It’s kind of like a chicken or egg thing, in many cases, where they want to attract more diverse audiences, but in order to do that you have to have some diverse people inside to make it attractive to new audiences. And that can be really difficult. And so the advice I try to give organizations is to stop thinking about the end game. Stop thinking about the wall that you need to build. Just start thinking about brick by brick, thinking about how I can go piece by piece. You look up all of a sudden and now you’ve built a more diverse organization. But you have got to really get your head down and get into the weeds and start to not be overwhelmed by the daunting task, but just start putting one foot in front of the other.

Samir:

Makes sense. And when you talk about one of those bricks that you just mentioned, one of them is mentorship.

Jabari:

Absolutely.

Samir:

In your view, do you think that’s getting enough emphasis and focus in the DEI conversation that’s happening today?

Jabari:

No. You need at least two people for mentorship. You don’t have that, right? You don’t have that. In my case, I was one of the more senior people in an organization that wasn’t that diverse. In those instances, you are asking that person to help mentor a large group of younger people in the organization, which can be really hard. There is a lot of pressure on the few people that you have at the senior level to support everything you have currently and will have moving forward. I believe there are other ways we can support our diverse team members. But I do think it starts with making sure you take care of the people that you have currently in-house. Especially the more senior people who are going to be the unlock, I think, to continue to build the diverse organization. And I say unlock because, let’s use Lyft as an example. Lyft is going to go do a bunch of diversity and inclusion events. They are going to go to a bunch of diverse conferences to try to bring on more diverse talent. And they are going to do a great job attracting them. Once those people get into the interview process, they are going to look and say, “Oh what other diverse people are at Lyft?” Then they are going to find me, and they are going to call me and say “Hey, I heard about Lyft, and the diversity of them, and I’m so excited about the brand. What is it like there?”

Samir:

Right.

Jabari:

And what am I going to say?

Jabari:

Either way I can say, “Man, this place is great. They really support me. They have these programs. I’m being mentored by senior leadership. They listen to me. I have a seat at the table.” I am going to then be the best marketer to bring on the rest of those diverse audiences. On the flip side, if I say, “Man, it is tough. I feel alone. I don’t feel like I have the support. There is nobody else like me. I don’t have any mentorship and I don’t know where I am going to go.” All that time and energy that company spent on diversity and inclusion recruiting is down the window in just two sentences out of my mouth.

Samir:

Yeah, it’s unbelievable, right? What an impact that could have. If you focus on your leadership and the people in your system right now, it can completely revolutionize your marketing and recruiting efforts.

Jabari:

Exactly. To me, mentorship is like—here is one thing I’ve learned, especially during the pandemic. During the pandemic, many companies dropped a lot of their additional services. I had executive coaching as part of my leadership training. But during the pandemic, they cut all of that. Right? So I had no executive coaching resources. However, I did learn that my white counterparts had friends and family that could help supplement that loss inside the company. They had an aunt that was a management consultant, they had an uncle who owned his own business, they had a grandparent who worked in Congress—whatever it is.

Jabari:

It’s very likely that people of color don’t have that additional support system outside of the company. When those resources are cut, people of color actually lose out exponentially more than those who already have support systems outside of that company. And so, I think there is an opportunity for companies to think about mentorship very much like they think about tuition reimbursement in college, right? They should allow diverse leaders to find mentorship and coaching outside of what the company can provide to make sure they can get the diversity and the perspective they need in order to thrive. You don’t have that above you in many of these companies.

Samir:

That’s an excellent point. I couldn’t agree with you more. In my own career trajectory, I can tell you how important mentors were. I agree that companies should really take that view with it. And I think that’s an excellent transition into understanding about Monday Night and why you started it, what sparked it, and how that is a catalyst for change in mentorship.

Jabari:

Absolutely. Monday Night Mentorship started a long time ago in my head in that I’ve always been an advocate for mentorship. Again, I’ve always been an only child and I didn’t want anybody else to grow up that way. My problem was with trying to qualify the right people to mentor because there are a lot of people who just want to take your time and energy. And also finding the time to respond to people and actually do it. I get so many emails on LinkedIn; trying to respond to them and set up time to meet somebody to interview blows my mind. I’ve talked to one of my buddies, Julian Dunkin, who is my co-founder in this effort. I said to him, “What are we going to do to help people? How can I support people?” We brainstormed a bunch of ideas, and some of them were going to take a long time. One of the things I actually learned and took from Lyft was the ability to be action-oriented. To really move with action. So that afternoon, I went on LinkedIn and said “You know what? I am just going to say I’m available.” Every Monday I put a note out, and said, “Every Monday night from here on forth, if you need help, support or mentorship, I am going to put a Zoom together and I will answer your questions, mentor you or support you in any way I can.” I got over 800 responses and emails.

Samir:

Oh my God.

Jabari:

One LinkedIn post and 800 emails, DMs, and I was overwhelmed, I’m like, “Oh my goodness.” Part of that people was were saying, “Hey, this is genius. I want to help,” as well. Here’s how you can do it. Here is how you can move. So I took a little bit of people who wanted to help, who I now call my Board of Mentors. They are CMOs and presidents at various companies, including Pure Leaf, Instagram and Warner Media, so on and so forth, who also wanted to be able to support and mentor people. What Monday Night Mentorship did is gave them basically an opportunity to plug into something without having to overthink who and how to mentor. So my mentors know that every Monday at 5:30 p.m., I can jump into a Zoom and mentor qualified people. The marketing community knows every Monday at 5:30 p.m., I can jump on a Zoom and talk to five or six CMOs of color and get my questions answered or talk about specific things relating to their careers or to getting a job. It really just became turnkey and super easy, and now we have about 3,000 people in our private LinkedIn group. The first of every month we do a big, open to anyone, come one come all Monday Night Mentorship, and that is about 300 people. Then the following two Mondays we decided to do a much smaller group to make sure there is two-way dialogue, and we can really work through people’s career problems.

Samir:

Just curious, how do you pair up the mentors and mentees? What’s that process like? To your point earlier, as an executive, you must get tons of pings; you kind of have to go through that filtering process of where it makes sense for you to spend the time and mentor versus putting someone in touch with someone else. How do you facilitate that process?

Jabari:

Well we found that our secret sauce is not in one-on-one mentorship, but group mentorship. What the Board of Mentors is consists of half seasoned marketers and business people, and half coaches, executive coaches. So you combine experience with the real tactics in coaching pieces and you get something really, really special. I remember I had my executive coach at Lyft, and this person was great and gave me some great tools, but was not a marketer.

Jabari:

Couldn’t help me with the marketing things I’m dealing with. This person was an Indian woman. She wasn’t Black, she couldn’t tell me how to do the things I’m specifically dealing with as a Black male. Which is very different than what I could be dealing with as an Indian woman. So, again, you have that experience. You have the diversity that sits on top and then you surround it with coaching, you get something really, really strong. Because it’s not one-on-one, you get the perspective of Jabari, who comes from sports and advertising, and you get the perspective of Menaka, who comes from research and analytics, and you really get a great, well-rounded point of view on whatever problem you are dealing with.

Samir:

Yeah. You’ve problem-solved mentorship, right? You are taking the experience and you are adding a piece of it so people can actually get some action items to take away and help them achieve something out of that.

Jabari:

Exactly.

Samir:

Which is amazing. As you talk to many of the mentors out there and for all the mentors that are listening, what are some of the most powerful questions that a mentor can ask?

Jabari:

A mentor is really there to pull out—some of the more powerful questions, right? We are not there to tell them what to do. We are there to really pull out where are they are trying to go, what are they trying to achieve? Help them see themselves in a new light. Give them new tactics in order to approach a specific problem that they may not have. I remember my mentor early on in my career said, “You have the right instincts, you just don’t have the right tactical tools to actually execute on what you want to get done.” That really stuck with me. It’s not just about knowing what to do, it’s about having the tools and being able to execute on that. So we try to bring both of those to there.

Samir:

And on the flip side of that, going back to the early part of our conversation and how you approached your first mentor when you were at Nike, what are the most powerful questions that a mentee can ask?

Jabari:

I think from a mentee standpoint, it’s less about questions and it’s really about wanting to do that work to really explore. We think about allowing mentees to create their own marketing plan and we want to make sure to really be specific to where each person is in their journey. So there isn’t lie one sort of killer question that you land. We try to understand as much as possible about where this person is in their journey and where they want to go and that we give them the right guidance from there. But largely, we want to give them the tools to market themselves, right? You want to be on the offense. Either you are telling your story or someone else is telling it for you. And so, you have to be able to understand who you are. You’ve got to understand where you want to go in life. You’ve got to understand what are your strengths and weaknesses. You’ve got to understand who is your team, your stakeholders, and the people that are going to support you along that journey. You have got to write it all down and start driving against that. If you think about a marketing plan, you can lay yourself against that same marketing plan and really figure out how to get to the next level.

Samir:

How can folks get involved? This sounds amazing.

Jabari:

We haven’t done a ton of marketing because we want to make sure that this doesn’t blow up too big that we can’t handle it.

Jabari:

The awesomeness about Monday Night Mentorship is that it is a two-way dialogue. It’s not a conference that you go to with 2,000 people and you just sit there and take notes. We pride ourselves on the conversation and the community. We want to be able to model something to companies to say, if you actually create a community, you don’t need to pay a ton of money to do candidate searches, right? If you think about the sporting world, do you think that the Lakers are going to have to go on this big search if Lebron gets hurt? They probably know exactly what players they are going to pull up from the D-league, or from high school or peewee, today they’re already talking to them. So imagine if we did that in business, where I actually knew a big diverse pool of candidates, I was building relationships with them early on so when that new role opened, I didn’t have to pay an exorbitant amount of money to go on this massive search.

Samir:

Yeah, you know who’s in the network. You know who the mentees are who are out there. I agree. It’s a completely different, new and innovative way of thinking about attracting and retaining diverse talent. So, transitioning a little bit, and when I ask this next question, I think about Shirley Chisholm’s old quote about services, the rent that you pay for room on this earth. You are clearly a big believer in the concept of servant leaders. We’d love to hear a little bit more of your philosophy of service and leadership.

Jabari:

One of my mentors told me early on, he’s like, “I work for you. I can’t be successful if you’re not successful. So my job is to get out in front, take bullets for you, be the shield, be the wedge, but you need to tell me what you need in order to be successful, and my job is to deliver it for you.” So that is just the way I think about things. It’s like – wow, my time is over.

Jabari:

I’m old. I’ve done some of my greatest work. Now I think about how I can support other people, how I can build your career, how I can make you rich, how I can support you – I have a tattoo on my arm that says, “Be the change.” Because I believe that if you want something in life then you have to do something about it. You’ve got to figure out a way to make it that. So instead of hoping the world becomes a better place, I’m trying to work with people and put what I have learned positively and try to put that into peoples’ minds so that we can—I think about life like scales, you know? You’ve got good and evil. Part of my job is to fill the side of good as much a possible so that good always wins over evil.

Samir:

Makes sense. When we are thinking about being the change, as you said, in many of the tech companies that you and I love, what should they be doing to be the change to be better allies to people of color when it comes to mentorship?

Jabari:

One, I think it’s about being honest about where you are today. Many times just getting over the hump like, “We’ve got work to do.” Right? A lot of times people will be defensive, “Well, we have this…” and, “Well we have that…” I think that people need to think about their values and are they doing it for themselves or are they doing it for show, or to show other people what they are doing. I’ve heard of a company, for example, say, “Hey, we are doubling our leadership of people of color.” But then you look at their board and they have one person. So, you are hiring one more person?

Jabari:

They make statements like, “We are doubling our leadership,” and that’s for show. And then there are people out there that want to use it as marketing, as an advertising tool. None of those are quite right in my opinion. You have to do the work, and that takes time and energy and you have to get some bumps and bruises. You’ve got to be out there in the community, and then you should be talking about what you are doing after you have made some progress. Action first.

Samir:

Are you optimistic?

Jabari:

I’m so optimistic. I’m like the most optimistic person you’ve ever had. If I wasn’t optimistic, I wouldn’t have had kids. But I have 12- and 13-year-old brown boys. My boys are mixed, but they come off as Black when you see them. I have to be optimistic for them. I know how things were when I started. I’m 45, and when I started there were no DEI conversations. I was the only Black person other than the mailroom in these advertising agencies. There was no Black employee network at Google at the time. So when I think about where I was and where I am today, you can’t help but to be optimistic because I also see some of my brothers and sisters around me that are doing some of the same work that I am doing, and that makes me really, really excited and keeps me optimistic. I know there are people that are serious about it and are putting in the work.

Samir:

We are optimistic, too. There has been a lot of progress, but I think we have a ways to go. Can’t wait. Thank you, Jabari.

Jabari:

Thank you so much. This was a fun conversation. The one thing I forgot to mention is let’s change the DEI conversation. Let’s flip those words around, add mentorship in it and let’s call it DIME: Diversity, Inclusion, Mentorship and Equity.

Samir:

DIME.

Jabari:

It kind of sounds cool since I’m a basketball player.

Samir:

It does.

Jabari:

I do things on a dime anyway.

Samir:

DIME it is. Alright, thank you.