Jonathan Jackson
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Email: jonathan@jonathandjackson.com

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How has New York shaped you in the time you’ve lived here?

I moved pretty abruptly in March 2014 from California because I found a new gig. I've always visited but living in New York City humbled me. It gave me a very real appreciation of adjustment and how personal it is to come to a place and have that place become your home. There are so many people that I love in this city. For me, New York represents the actual becoming of who I am. These are some of my most formative years.

Jumping into all things Blavity, what do you think makes your founding team work?

I have a level of deference and admiration for Morgan and Jeff. There is a certain resoluteness of character each of us emanate in very different and specific ways, but we know each other. The demand the business has placed on us professionally and personally, as well as the standard we hold ourselves to, require it. I like to think we can throw each other no look passes and we don't have to worry if someone is going to drop the ball. We haven't been immune to life. Even though we may not talk about it, all of us have encountered tragedy while building Blavity. Seeing each other in those moments and figuring out who we need to be for each other is probably the thing that has allowed us to move quickly. As that relates to the business, you get to know people’s areas of expertise and how to anticipate their movements in a way that allows you to fill in the gaps from a place of collaboration as opposed to infringing on territory.

What does your role entail as Head of Corporate Brand?

The role is focused on the external side of the business. That includes external affairs, larger scale partnerships, community relations and really the ethos of who we are. I've spent a lot of time explaining our mission and purpose practically so that people understand why and how they can get involved with what we do and who we are. I try to open doors as quickly as possible so when my team needs something, they don't have to knock, they can just walk in. For the moment, I do a lot of speaking in rooms I think it is necessary for us to be in. What made us unique and get early traction is that we tried to show up for people and I still do that with the level of influence I have. One thing about this lifestyle as an entrepreneur is you fight really hard to have control over your day. That's a privilege I exercise by being in spaces where I'm not the focal point. I'm not there to lecture or talk. I'm just there to sit, listen, learn and understand what it is people are talking about. That’s important.

What nuances are required in your role when approaching each of the brands that fall under the Blavity Inc. umbrella?

They're interconnected but they really stand alone. Travel Noire is a distinct brand - down to the colors, the picture quality, the way things are shot and the tone of the newsletter. It's complementary but it doesn't sound like the Shadow & Act newsletter. You have to be sensitive to what that means for a consumer. They might read both but expect different content, are reading in different frames of mind and at different times of day. There’s a science to it. The nuance for me personally is that I've had to learn a lot of emotional intelligence and a high level of intellectual humility. The thing I can speak to more than anything right now is how much I know what I don't know. The choice then becomes do you create an environment in which you can go learn those things and get high skill acquisition or do you pretend like you know them and deal with the consequences? I have done the latter a bunch of times and failed. More recently, I've tried to do the former and it transformed my life.

What are the major keys to maintaining consistency in a brand story?

You have to think about the distinction between your vision, which is the world how you see it and your mission, which is the thing that you are moving closer to every day. I think sometimes people get those things conflated. The problem is that the vision is the imaginative. It is the Westworld, if you will. As the mission is more tangible, I think the vision is what confounds us and can cause a great deal of anxiety because we know the vision is big enough that we might not live to see it realized. That doesn't mean you fail. It just means it’s a grand vision. The mission allows you to take tangible, measurable steps towards it. I think that's a really important thing to talk about and meditate on. If you're rooted in your why, then the how becomes the input and the what becomes the outcome.

How about when building a personal brand?

The groundwork takes as long as it takes. If you're trying to build a portfolio that comprises various aspects of who you are, some parts of that portfolio are going to require different things from you that you might not have yet. That's not to say you aren't capable. It just means that what got you here won't get you there. I think a lot of us are scared of that type of realization because it means you have to change and rebuild yourself repeatedly. I've had to do and am currently doing that in public and in front of my peers. You can feel a level of nakedness that’s disconcerting because if everybody knows you for the thing you used to do, what happens when they don't know you for the thing you're about to start doing. We are worthy of the adjustments in our life that we have to make. Whether people appreciate us or hold us down while in transition is irrelevant. If you believe you're enough, then what you need will be there for you. It might not look like what you thought, though. That, to me, it is the fundamental difference between someone who has longevity and someone who has an interesting brand. If you understand demand, then you can build a brand. The question is will the demand look the same in 2020 or 2040? People want the same stuff, but the vehicle through which they get it is beyond your control. If you have to constantly worry about remaining top of mind and being popular online, you might need to rethink your strategy because people still want to interact offline. Many can't make that transition. You can be really cool online and trash in the room. That's a dangerous line because then people don't know who you are and it takes a long time to build trust.

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Blavity's funding journey was historic for Morgan in terms of becoming one of the less 20 Black women who've achieved the milestone of raising $1 million in capital. Could you share how you supported the effort?

To execute my role, I had to hold myself to a standard that the only person who can be better at telling our story is Morgan, the person who came up with the idea. When Morgan raised capital, the requirement from the rest of us was to hold down the ship, so she could focus and get what she needed in those spaces that, in many respects, are unkind to people of color and especially Black women. The question for me was always am I telling the highest quality story about who we are and what we have the capability to do as a business and as a team? I've fallen short of that a bunch of times but I now try to say “no” to the wrong things so I can say “yes" to the right things. There's a point at which it’s no longer zero sum. There are a bunch of interesting things you could do, but you have to decide what is the highest value use of your resources.

Let’s hear your exit from corporate story. You were working at LinkedIn while building Blavity at the same time. How did you balance the two? When did you decide to make the jump and how did you do it?

Balance is hard and wasn’t always achieved. I tried to always do well on my day job because that can kind of keep the pressure off. You can't be wack at your day job and good at your side hustle. That doesn't work. You've got to at least maintain equilibrium in your 9 to 5 so you can give yourself flexibility. I was good at my job. I liked my team. I enjoyed my environment. I want to be clear that I didn't hate what I was doing. But Morgan made a very specific ask of me in terms of needing more of my time to help Blavity and gave me the space to make a decision, which I believe was the right one. However, I wouldn't recommend the way I transitioned. I was pretty impulsive, which could impact your ability to maintain quality relationships at your last employer. I was very bullish on was making sure that the relational capital I had never faded. There was never a point where people could misconstrue why I left. That was top of mind for me because I had worked really hard to build a reputation for myself and media is not a big world. There are really influential and powerful people that know other people, so it's in my best interest to maintain a level of decorum with them because I'm going to see them again at some point in my career. Careers are long. Jobs are short.

What are your thoughts on today’s narratives around quitting your day job?

I think they are devoid of nuance and that's really bad. There are tactics and strategies you should employ if you’re going to take this type of risk and don’t have a safety net or wove your own. Don’t quit until it’s absolutely necessary. If people are shaming you for it, cut them off. They aren’t going to pay your rent. We know there are different things required of us so we should stop being naive about the different ways we need to navigate the systems we're in. Be practical about it and be honest. If you're getting your bag, keep getting your bag. Figure out the runway that you need to feel comfortable. If that's six months, 18 months or whatever, plan for that. Don't ever allow somebody to dissuade you.

What is a core principle that you've applied to your life and has had tremendous impact on your trajectory?

Second order thinking, which is based on the idea that people usually make decisions for immediacy. For example, leg day in the gym. First order thinking, this is going to suck. Second order thinking, a month out my stamina is going to increase and I will have more strength in my core because of it. Second order thinking applies that you are making decisions based on the actual outcome and you can withstand the first order negative thing. That fundamentally transformed my life because now I don't make decisions based off of the immediate pain or pleasure I might feel. It is doing the hard things early and repeatedly. That leads into the idea of exponential growth. We sometimes don't think about how powerful compounding interest is in our lives. It's why people suddenly blow up. It's the Cardi effect. “Two mixtapes in six months.” She was compounding. So, of course she’s having this year. She worked for it. And that is agnostic of career or industry. It’s a framework to apply to anything that’s hard but requires simple tactics.

Congratulations on your recent acceptance into the Nieman Foundation for Journalism. In your announcement post, you mentioned it was a process for you to pull the lever to apply. What are you most excited about after having taken that risk and ultimately being rewarded for it?

I'm really grateful. As somebody who is a student of rhetoric and writing, I'm humbled that I get a chance to experience an academic year with essentially unbridled access to some of the best resources and minds on the planet that are thinking about what the future of media, journalism and storytelling. I'm excited because my project is focused on the emergence of Black cultural influence and digital platforms in this current time. I'm interested not in the individual trees, but in the forest we built and what that forests needs to grow and become more rooted. We know how influential we are, but we don't have the data we need to tell the story of our influence. I've started to think about what that gap could be and if we can create new ways to measure our influence that don't rely on the things we typically go to. I want to understand how we can actually take ownership of what that really means, so we don't have to keep yelling about how influential we are after something happens.

What's on the horizon for you?

I am in a transition in my life and I'm going to do more writing about my last four years. So much has happened to me personally and professionally that I think I could do more good articulating what those things were and what I had to go through. I'm really interested in exploring myself as a speaker. I'm actually pretty introverted but I play an extrovert publicly. I'm trying to give myself more spaces to talk about other things than I've typically been known for. I will also spend a lot more time with my family. I've made excuses as to why I can't be a part of things and those are no longer adequate for me. I have to really think about how I want to show up and design my life around those things that matter instead of reacting to the things that are distractions from them. A personal goal of mine is to say “no” a lot more. Early and often.

How do you stay motivated as you strive to achieve all of your goals?

I think a lot less about motivation as an idea. I don't give into feelings. I can acknowledge them but they're not facts. I think about habits. We all have those things we do automatically without thinking, so why can't I align those with my goals? Why can't I put myself on auto-pilot towards stuff that actually matters to me? I've been trying to rebuild some systems for myself or structure daily habits that get me in the right frame of mind and environment where even if I don't feel like it, things are muscle memory. Every day I wake up and my laptop is open and when I log in, it's open to blank page, which cues my body to say "Oh, it's time for us to write." Sometimes it's not whether you want to work out. It's whether you actually put on the gear to go to the gym.

I think we do this thing where we peddle motivation as this magic pill when it’s asking yourself “Am I professional or an amateur?" The difference is that professionals show up. I need to show up for myself. There’s a personal level of accountability I try to build into the things I say I want. I’m not outsourcing my goals to someone else.

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