Blavity Co-Founder, Jonathan Jackson, Transitions From LinkedIn 9-5 Into Full-Time Entrepreneurship

EP 31: The Path Less Traveled Series ft. Blavity Co-Founder, Jonathan Jackson

The Path Less Traveled Series, is an inspiring web series spotlighting millennial entrepreneurs. Each episode is packed with actionable tips on how to successfully turn your passion into a lucrative career.



In The Path Less Traveled Series' first-ever live taping, Neffy Anderson interviews Blavity co-founder and head of corporate brand, Jonathan Jackson, following his decision to step down as manager of LinkedIn’s influencer program.  Blavity is a rapidly growing media startup for black millennials in which Jonathan exercises his gifts as a writer, editor, and digital strategist in order to amplify the voices of people of color. Following his transition into full-time entrepreneurship Jonathan sits down with Neffy to transparently detail what that process was like, expand on how Blavity is pushing the boundaries of media, and share his latest essay project.   

Watch the interview highlights here and listen to the full interview on SoundCloud and iTunes. Don't forget to LIKE, COMMENT, and SUBSCRIBE!


10 Things You'll Learn From Jonathan Jackson's Feature on The Path Less Traveled Series

  1. How to smoothly transition from your 9-5 into full-time entrepreneurship
  2. The benefits of NOT hiding your side hustle from your employer
  3. How to prepare for a stressful day
  4. What you have to give up in order to do the things love
  5. How to create space for yourself
  6. Actionable ways to lead with value
  7. How to nurture your business relationships
  8. The right way to prep for a meeting
  9. How to maintain relationships established at work after you've left the company
  10.  A trick for refreshing your perspective




Disclaimer: The opinions expressed in this interview are those of the guest and not those of The Path Less Traveled Series and/ or Neffy Anderson


[Video Introduction]


JONATHAN JACKSON: People told me that being a writer was too difficult and that I probably shouldn’t do it but I’m here because I decided to tell my story and I have other stories of other people that I want to make sure get out, so that’s what I’m focused on.


NEFFY ANDERSON: Hey everyone, it’s Neffy Anderson here with a brand new episode of The Path Less Traveled, a web series spotlighting millennial entrepreneurs who successfully turned their passions into lucrative careers. Today’s guest is writer, editor, and digital strategist Jonathan Jackson. Everybody give a round of applause for Jonathan Jackson. Show this man some love. Put some respect on his name.


Now let me give you the rundown on Jonathan, okay? Jonathan is most known for being the co-founder & head of corporate branding for Blavity, a digital destination for & by black millennials covering everything from pop culture to politics. Now what makes blavity so special is it’s commitment to covering stories that are important to the black community that may otherwise go untold by mainstream media. Jonathan & Blavity together have been featured by outlets such as Forbes, USA today, LinkedIn, the huffington post & now The Path Less Traveled Series. One time for Jonathan everybody.


[Audience clapping & cheering]


He’s pretty amazing. So Jonathan thank you so much for being here & for allowing me to interview you, & for being the first guest for the live taping.


JACKSON: That’s dope. Thank you for having me.


ANDERSON: I’m so blessed. Now just like in church when the pastor gives you a moment to take out your bibles, I’m gunna give you a moment to take out your phones, okay? When you tweet make sure you  tweet using the hashtag #tpltseries. What’s the hashtag?


AUDIENCE: #tpltseries


ANDERSON: I like y’all. Y’all smart, y’all loyal, all that good stuff. Alright, so it’s gunna get deep really quickly. I’m like, “Jonathan, I usually don’t have cue cards or anything but … there’s a lot to cover & so many questions I want to ask him. I’m truly a fan. So, I’m gunna try and breeze through this and then he has something special for us at the end so, here we go. You ready?


JACKSON: Let’s do it


ANDERSON: You scared?




ANDERSON: You should be


AUDIENCE: [Laughter]


ANDERSON: So let’s kind of take it from the beginning. Talk to me about how you guys came up with the name Blavity. What does it mean & where did the idea for the company come from.


JACKSON: My co-founders, Morgan, Jeff, Aaron, & myself all went to Washington University in St. Louis and the campus demographics are around 4-6% black (they say 6% because they just add in the grad school to make it seem more black but it’s not. Anyway -- there were only a few spaces on campus where black people could gather. & one of those was actually a lunch table when we were there & the term we used was Blavity, right? So it’s the word Black & gravity, so it is a noun in the sense where you see someone black there is a feeling attached to it -- but it’s also a verb. It’s that head nod you give when you’re in Home Depot with somebody & you’re like “Yeah, you’re buying supplies too. Dope.” It’s just that feeling. That sustained us while we were on campus but when we left -- & this was really led by Morgan, we really didn’t have a space that we felt like was sharing our voices & everything was disparate so we were all scattered but Morgan brought us together around this idea & we’re here around 2 and ½ years later.


ANDERSON: I love it. You mentioned that there are 4 co-founders (you being one of them), talk to me about each of your roles as it pertains to Blavity.


JACKSON: Morgan is the founder & CEO so she does everything, her hands are everywhere & she is responsible for company vision & setting that. Aaron our COO is involved in anything that is revenue generation -- so that’s big deals, partnerships, running the sales team, looking around new clients we should go after. Then you have Jeff, our CTO. We’ve always had a tech stack -- so we had engineers since the beginning & so he is the tech wiz & genius behind that. My role is kind of interspersed. Corporate brand is sort of a jargonny way to say that I look to make sure that we are in the spaces & places that we need to be so there’s industries that need to know about us, there’s foundations, there’s companies, how can we work with them & what does our story look like & how are we delivering on that promise for a community & also for anyone else that we work with.


ANDERSON: I love it. So you mentioned that you guys have recently celebrated your 2 year anniversary. Congratulations.


JACKSON: Thank you.


ANDERSON: But, you also quit your 9-5. You said peace out.




ANDERSON: You were at LinkedIn for about 3 years in a variety of roles. So talk to me about how you made the decision to leave the company & what did you do in order to transition out.


JACKSON: Yeah so, I think my decision was predicated on a few things. I loved my job. I think the prevailing notion is that people are like “Yo, I cannot wait for the day I leave. Like I wanna hit my boss with an inanimate object.” I didn’t have any of that, I really enjoyed what I did and who I worked with but the reality is that when you want to do something you love you have to give up a lot of things that you like. And I believe for me, I was on that path and it got accelerated because of Blavity’s growth -- it never slowed down & as much as I wanted to do both I wasn’t always giving what I should have given to the thing that I was around for the beginning of. I made sure everyone that I was working with knew the things I was involved with outside of that which made the transition a little easier.


ANDERSON: I just wanna know if you guys caught that quote though. Right? You got it? You Got it? “In order to do what you love you gotta give up what you like.” I like that. DJ Khaled voice. Talk to me a little bit about your writing. I know that in the very very beginning stages when Morgan first told you about this idea she’s like “I want you to come onboard” & you’re like “yo, how can I help?” & she was like “you can start by giving us some pieces.” Talk to me about your love of writing, like where did it come from, has it always been a passion of yours?  


JACKSON: Yeah, so it started really young, right? So now I’m really able to call myself a writer, I didn’t do that til like a year and a half ago. When I was really, really little my mom used to tell me this story about [how] she used to read Peter Rabbit and I used to have her read me the same story over and over again. And then … on the way to school I’d be in the backseat, & I’d have my Peter Rabbit book & I’d open the pages before I knew how to read and just re-tell the story. My brother’s friends would be in the car & be like “Yo, is your little brother like actually reading? He’s like 4.” I would be like I don’t know what I’m doing. But that was like part of my beginning. So the love of diction and storytelling and how you can actually take an idea & words & paint -- that’s how I like to create. From there I’ve always had this voice but there have been times where I’ve held it or I’ve shielded it, but more recently with Blavity it pushed me way out of my comfort zone because I had to start telling that story broadly so it’s been a progression. I’ve always had it I just recently decided to dedicate time and effort to it in a meaningful way.


ANDERSON: So what would you say were some of the opportunities that you created for yourself that led to a big break in your career & or Blavity.


JACKSON: There’s a couple. My fourth week at LinkedIn. I was in a room with a cohort. I was in a rotational program. We were asking questions of the SVP who’s this great dude and I looked around the room & per usual I was one of the only black persons in there, and they were talking about talent and how important that was and I raise my hand. He was like “Jonathan do you have a question?” I was like “Yeah, just curious -- like why we don’t recruit below the mason dixon line” and the whole room was like … [looking around confused]. Then I said, “To be more specific why we don’t go to colleges with higher demographics of black people if we believe talent is the future.” Obviously no one wanted to involve in that conversation. I felt like if I was to get fired I still had SouthWest miles so it wouldn’t be that bad. But for me asking questions like that allowed me to differentiate myself. Not because I wanted to be disruptive, I just felt like I had questions that no one else could answer. So my ability to separate has been more about my curiousity than me naturally being more talented, stronger, or faster. I’ve dug into the questions that no one else can answer & it’s allowed me to create space for myself.


ANDERSON: I love it. So, what did you do to deliberately brand yourself. Would you say that that was it or was it something else? Because you’re good at a lot of things. I’m not gunna embarrass you & go through your whole resume, but you did mad stuff … PR, ALL THAT.


JACKSON: Yeah. I think it’s that I’m really interested in people. So my thing is I try to lead with value first & from there then it can be whatever it needs to be.  So if I believe why shouldn’t I do that then my operating properties shift to figure out what the space can look like. The reality is with the internet you can do a lot of information gathering in a very short period of time so I do a lot of homework before I show up. That allows me to walk into a room knowing who I’m talking to & then further more knowing their priorities -- and then, if I’m really doing my work, knowing who they report to & their priorities, and so that makes the conversation a lot more streamlined.


ANDERSON: What do you think is one thing that most people don’t know about your journey to where you are today?


JACKSON: I was not always as personable as I appear to be. Umm, like a lot of things growing up that I think most people don’t know about but … I had a speech impediment for a while so like “t’s” & “h’s” were not a thing. So like I had a really bad lisp and I didn’t like speaking in front of people, I was really shy, like I would never have done anything like this.


ANDERSON: Well, you’ve come a long way. Congratulations


JACKSON: Yeah, thank you. That’s definitely part of it. But I also think that it’s not overnight. I have always been this type of person I just haven’t necessarily been doing it in front of a lot of people.


ANDERSON: So what do you say you know now about the startup industry that you wish you knew when you first started.


JACKSON: I think you just have to have a healthy respect for understanding what you don’t actually know. I know that I didn’t know that much. But when you actually like really quit your job & you’re like I’m actually gunna do this you realize how much you actually don’t know. So there’s like a gap. So accepting that & leaving your ego is probably the most important thing that I’ve done cuz it’s allowed me to make whatever mistakes I need to make and accelerate through them.


ANDERSON: So i wanna go back to you leaving your job. Talk to me about the steps that you took in order to make that happen successfully?


JACKSON: Yeah, yeah. It was pretty successful. I did a couple things. So the first one was when I got to LinkedIn I knew a couple things. I wanted to make sure that one -- regardless of my role if my name came up in conversation it was bullet proof. Like if they said someone had the same last name as me there should be a conversation around if we’re related and if so they should have the ability to get access to things they wouldn’t have. I was very serious about my legacy coming in cuz I didn’t know anyone.




JACKSON: So that allowed me … I basically started meeting senior leaders very early because I wanted to know what their priorities were. Because I knew I wasn’t gunna be there forever but if I’m here & you can give me access & there’s all these free snacks I’m absolutely gunna do my due diligence. So, I created advocates & I found sponsors -- people that would talk about me when I wasn’t in the room & show me opportunities that they felt I might not actually be ready for but I could take advantage of. So those people I carried with me when I left & those are relationships I nurtured because whatever they’re doing is directly related to what I might want to do in the future or what I’m doing right now. So I think that it’s about involving people in your story before you need anything from them.


ANDERSON: Right. So once you knew like okay, I’m gunna go ahead & take this step, like … do you start saving, when do you have that conversation with your boss ...


JACKSON: Yeah. I saved from jump. Like, that’s not really an option for me. Right? I was always like, well if I’m making this what would I need for this if everything went left. So that’s not being a failist I think that’s being a realist. Like, things happen in life where you’re required to be more liquid & so I always knew that so that’s like been a historical pattern, so I needed that cushion anyway. But then when you’re leaving it’s like okay, ummm what can I gather outside of the actual paycheck. So I had that open conversation with my manager, right? He’s very transparent. I was like “Hey, this is what I think I’m gunna do, what do you think?” & he was like “ go for it” & I was like “Can we stay in touch?” and he was like I’d be upset if we didn’t. & so what I’ve found is that people who are more senior in their careers, they’ve usually sold everything they needed to sell, they’ve done everything that they want. What they actually want is to see people that they can help with their actual influence cuz that can sometimes give more purpose to their work, than what they’re just doing. So for me, I was like “Hey, I’m doing this thing, it;s in media, I think it’s interesting, can I email you every 4 weeks with an update?” and they’re like “yes.”


ANDERSON: To your manager?


JACKSON: To my manager or anyone senior I engaged with. And I was like these relationships matter, how can I communicate that they matter regardless if I work in this organization or not.


ANDERSON: So how did he take the news? Okay so, let’s go back a little bit cuz I wanna marinate here a little bit. Cuz I feel as though we have a lot of people in the audience and that are watching that are entrepreneurs & you know, they have 9 to 5’s -- & they may love them as you do, or they may not & they’re tryna figure out next steps, like “How do I you know, transition smoothly, without burning bridges, you know, into this next thing, this thing that I love?”




ANDERSON: So, you had a conversation with him how far out from you leaving?


JACKSON: I had a conversation around what I was saying about as far as my career was concerned probably like 3 months earlier. Right? So I also made sure that I had time with my manager. Like, that’s my job. It’s not my manager’s job to schedule time with me. If I need resources from a person I need to be on their calendar because it’s about me. My career is my own. I own that fully. So I was setting up time. One of those conversations was “Hey, I’m thinking about this.” And I had never really hid the fact that I was involved with Blavity, people knew it, people knew what was going on, & I was like “Hey, I’m thinking about this. I think it’s time. I think I’m in a space where if I don’t do this now I’m gunna regret it” and I think that resonated, and as someone working in media I think he understood that. He wanted to support what I was doing because of the caliber of work I’ve been doing previously. I think the other thing is, you can’t be wack at your job (your 9-5) and expect someone to support your your 6-10 because they’re not seeing your criteria, especially if you know you’ll need something from them immediately or you’d want something in the future. So i made sure to that point that I was executing on everything I needed to & that allowed me the space for people to be like “Oh, absolutely, do your thing, you’ve been great here but I bet you’ll be better doing whatever it is in the future.”


ANDERSON: So what would you say was the last low point in your career & how did you bounce back from that because the message that we want to get out is that you are gunna have low points, not everyday is gunna be a bright day so you know, we fall down but we get back up.


JACKSON: I think I wouldn’t call it a low point. It’s a battle, right? Doing what I do now, I can have a string of good calls and then I have something happen that throws my day left. I can tell you that last week there were like 4 or 5 times where I was like ahhh, this is like, not that great. But then there was like, there was just as many times where I was like “it’s lit.” But if we’re talking about a consistent low point, there was a period last year where I had gotten into a new role managing the influencer program & I was wayyy out of my depth. Like I did not think I could do it. Period. I was like this is too much pressure, why am I here, so it was a deeper level of imposter syndrome than I have ever experienced.

ANDERSON: You’re referencing LinkedIn’s Influencer Program?

JACKSON: Yeah. So, that’s a program for 500 of the world’s top thought leaders and I was managing that & making sure that we were reaching the people that we needed to & finding new voices to add to that. That was just really, really, weighty for me & I felt like I didn’t deserve it. A lot of the game was mental for me. The low point was that I was cognitively struggling to understand if I was good enough to execute on these specific things, and  if I wasn’t what would happen to me. I think I was just blessed with a manager who refused to let me wallow in that and they were like “You’re great, otherwise I wouldn’t have hired you. So do your job cuz you’re the only one that can do it.” Someone talking to me like that who didn’t have to allowed me to continue to grow

ANDERSON: So, what would you say currently is or has been the most challenging part about being a part of Blavity?

JACKSON: There’s two things. The first one is the landscape, right? So if you look at media itself, umm it’s volatile in general, it’s busy, things are always changing as you obviously know, & for us we came in the game if you will with a clear declarative statement. We said we’re focused on Black millennials between the ages of 18-30 period -- & we believe that their stories matter & that they have 28 billion dollars worth of buying power and they’re being critically underserved, and we’re tired of it. And we came making things that people keep taking & we’re not gunna let that persist. When you make statements & people don’t necessarily know who you are yet, it can obviously create friction. But it also creates ripples in the market place. I think what’s been most challenging for me is how to distill our vision into tactical things, cuz I spend a lot of time thinking about where we need to go, where I need to speak, what i need to say -- but the challenge is not everyone is at that space where they can digest the vision. Some people need like, what are you doing right now? Some people need “what does it look like?” & other people really wanna be involved. But in this case it has actually pushed me to be a better communicator.

The second thing is, we’ve grown really fast. So if you’re doing anything & you’re growing you have to think about 1) the people on your team 2) the type of leader you want to be for them  & what that looks like, & giving them what they need to be most successful.

ANDERSON: Love it. So you guys have done a great job of bringing us fresh content. There was like this thing that went viral … what was it? The Black Twitter Date?

JACKSON: Yeah. Yeah. Yeah. That was a smash.

ANDERSON: That was pretty funny. Talk to me about your business model & your monetization channels

JACKSON: So like any good media company we have advertisement, but we also do a lot of work directly with clients, we’ve done sponsored content campaigns, we’ve done live event activations, we did EssenceFest for the second time this year. We did some cool stuff down there. And then when you think about larger campaigns, so for us the revenue has always been about how we can deliver something of value to our audience and who we can work with to do that in a meaningful way that accomplishes their objectives. I think for us we’ve seen a lot of growth for a lot of different brands who are looking to reach our demographic but are obviously fearful of  1) not appropriating 2) not just being flat out wack and having it be something that’s not what people want to engage with -- & what the future is cuz it’s not as much data on our actual user base as they should be.


JACKSON: And so that’s something that I think about regularly. We deserve, not only to be reached but to be measured, and indexed, and have the same rich and robust data sets that you’d see for any other demographic of people out there.

ANDERSON: Right. I love it so, it’s time for us to actually take some questions from the demographic. So we posted a question on Instagram, if you’re following him then you already saw it. Let me just get my phone and see what they got here. Okay, so Caleb Reaves want’s to know how do you prepare for a stressful day.

JACKSON: That’s a great question. I think it starts at night. So I did this thing two or three months ago where I started this gratitude journal. So the entire point of the journal is I just write bullet points of things I’m grateful for that day. And that sounds kind of meta but I mean like literally -- if the D-train is on time I write it down. Like the D train was on time today, Google Docs didn’t crash, the bodega made my sandwich with pepperjack, right? Anything that I feel like can refresh my perspective. Cuz I think your next day begins the way your night actually ends so I try to be really intentional about like … I don’t want to go to sleep other than thinking about the best things that actually took place, & so I think that starts it. In the morning I have quiet time. I try to meditate, I try to pray, I try to think, & also, if there are things that are really difficult I try to get it done in front of the day. Seth Godin calls it eat the frog, so do the hardest thing in the morning first & everything else can go from there.  

ANDERSON: I can dig it. I can dig it. So, we have a question from Marquelle Turner. I wonder who that is.

JACKSON: My man.

ANDERSON: He would like to know what song represents the current state of your life

JACKSON: Man, this is tough. There’s a couple. Current state … I think I’m on a gradient here. So I am in between Young M.A. “ooouuu”

AUDIENCE [laughter]

JACKSON: I’m there. But on the right end of the side I think that I’m also between Marvin Sapp “Never Would Have Made It.” I think that’s the vacillation point. I think on that end I’m doing things now that I couldn’t have imagined. That’s like really, really, really, incredible for me. And  on the left side I think that there’s never not a good time to shmoney dance.

ANDERSON: So what we’re gunna do now is we’re gunna transition into talking a little bit more about your upcoming project that you’re going to release.


ANDERSON: Called 25 to Life.


ANDERSON: You been to jail?


ANDERSON: Okay. So talk to us about 25 to life. Where it came from, what it is, all that good stuff.

JACKSON: Yeah, so 25 to Life is a 5 essay project that I worked on between November of 2015 & like right now. So the backstory is: 6 months after I turned 25 I found myself in this weird space where I was just like is this like what quarter life crisis feels like? I was just like I don’t really know what’s good like … life doesn’t make sense. Like, I had a new job but I was like man I think I’m gunna have to quit. But then I’m like I’ve never quit anything, what would that make me look like? And, I also was writing through that and I also was in  a place where like I feel mentally I wasn’t that healthy and I didn’t really tell anyone about it. Like in retrospect I probably was in fact depressed but I was aldo functioning at a high level so I assumed those 2 things were mutually exclusive when they’re not. They’re very interdependent. So, suffice to say I would come home from work everyday & I was just writing. What came out of that was a couple series of essays. I didn’t think any of them were good enough so I hid them, but what I did do was one that I felt was ehhh I sent to our lead editor at Blavity, it’s called 16 Painful Things I Learned While Adulting. That was part of a larger essay question. That went out, people resonated with it, it did pretty well socially, but I kept the rest of the essays to myself. So, in the past month or so, I realized that it’s disingenuous to tell people to be expressive & creative if I haven’t made anything. I linked with my homie Andrew who’s a photographer and we did a series of actual pictures attached to each of these essays to capture the emotion that I had about a year ago. It’s everything from death, love, … there’s very very disparate things involved there but I think it’s accurate for where I was in my life and I think it’s probably the best body of work I think I’ve written because it’s the most truthful which makes it the scariest. So, looking forward to that.  

ANDERSON: I just wanna double back to talk about that space you were in where you were depressed. How did you even realize that you were depressed. How did you get to that place where you were like this is like not okay.

JACKSON: I’ve had my own wrestle with that. So like in high school I lost my short term memory for 14 months so I went through a period of anxiety. That was very palpable because there’s actually things I noticed about myself and my behavior that fundamentally shifted. So because I had that base work I was able to see what I was doing & take a moment to go okay, what are your habits & why are they changing drastically? This is not the reflection of a bad day, this is not a bad feeling this is an actual thing. Because I have that rubric to work from there are specific things & tactics that I can use & implement to allow myself the space to just be like this is where I’m at, but here’s how I want to actually get out of that. That was really helpful. I have a lot of people praying for me so that’s also an addendum, but I think it was a mixture of that and that I just decided to get to the root of what it was & be okay that that might be an uncomfortable process. And that it’s not a process that other people necessarily need to be involved in but they are there to help me which is what a village is for and I have probably one of the best ones I know of. And so I leaned on them where I needed to.

ANDERSON: So, how did you get to this space where you could be so transparent, so in touch with your feelings, so you can not only communicate that with your love ones & the people that know you but, elsewhere?

JACKSON: I’ve always been that person. The difference now is that I’m actually sharing it but the people that have been around me when I’m home & I’m just with the people that know me I am this. Like, this work I did sounds like me because it is. I think from a transparent point I just felt like no one else was doing it. Like, that’s the gap I see in the market. I see I have a lot of conversations with people who for some reason want to talk like I do but are like I could never do that so I need you to keep doing what you’re doing because it allows me to see myself. So I take that really seriously when someone tells you that you’re giving them space. I think the other side of it is I’ve never had trouble expressing myself I just never knew the right vehicle in which to do it. I found more recently that words are a thing that I’m not randomly good at. It’s something that I’m gunna do for the rest of my life and  because of that I’ve just committed to actually tryna tell the stories that I think exist. But also, there are a lot of people that I grew up around or that I’ve seen that never got a chance to tell their story & so I would be doing them a tragic disservice if I didn’t tell the best stories I could in the most honest way possible, using the mediums I’m tryna learn how to master. I don’t know what that looks like but I do know that it is a part of why I’m able to do the things that I do. If it can help people I think that matters. And I think that it keeps my relationships with my close friends honest. Cuz they know me and they know that we can have that level of conversation.

ANDERSON: I love it. Jonathan, I speak for the audience, the people behind this camera, your entire family, mom, dad, we’re so proud of you. We are so proud of you.

AUDIENCE: [applause]

ANDERSON: Thank you so much for having the courage to turn your passion into your career & for walking in your purpose.

JACKSON: I appreciate that. Thank you for having me.

ANDERSON: You the man! Now if you guys enjoyed this interview as much as I did I need you to let me know it, don’t be stingy don’t be cheap. You ready? Let’s get close, let’s get close. I need you to like, comment, subscribe, and share it on your social platforms: Twitter, Facebook, you know the deal. Alright? Until next time, bye.