About this episode

Jason Y Lee is the founder of Jubilee Media, which launched in 2010 with a goal of creating a movement of empathy and connection. While most media brands play for entertainment and devisiveness, Jubilee is desiring to swim against the current for human good.

In this episode, Jason shares openly and honestly about the personal journey he went through to understand what it was that he knew he was supposed to be doing with his life. He had an incredible job working for Bain Capital at the time, and his original co-founder of his first venture, that preceded Jubilee Media, was his brother who was a staffer for President Obama. To make a career decision like leaving those positions, he had to be all-in on his pursuit and purpose. Yet like so many entrepreneurs you never really learn how all-in you are, until it all starts unraveling, and Jason shares all of it in this episode.

In this episode, you'll hear:

  • Jason was born and raised in America by his Korean parents who immigrated to America. His partners pushed his brother and himself into traditional careers to provide job security for when they were older.
  • Jason shares how he stumbled into entrepreneurship while he was working as a consultant at Bain Capital. They were being shown pictures of the disastrous earthquake in Haiti. Jason wanted to raise money as quickly as possible so went and busked. This sparked his idea of creating video content to raise awareness and the Jubilee Project was launched as a non-profit organization.
  • Jason explains how he convinced his brother to leave his job, as a staffer for President Obama, to cofound Jubilee Project with another friend who dropped out of Harvard to join as well. This path lasted for a few years before it all unravelled.
  • Jason shares his journey and process he went through to figure out a path forward after his cofounders left.
  • Jason's story is one of understanding your personal value proposition and clarity of mission.
  • Most founders truly do believe they are fully dedicated to their mission, until it all "hits the fan". It is in that moment you will see who is "in it to win it"

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Jubilee Media: https://www.jubileemedia.com/
Jubilee Youtube: https://www.youtube.com/channel/UCJjSDX-jUChzOEyok9XYRJQ
Jubilee's Tribeca Submission: https://tribecafilm.com/films/accepted-2021

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Episode transcript

Jason Y Lee: This is Jason Y Lee, founder of Jubilee Media, and this is MY startup story.

  • Every wildfire began with a spark. Every superhero has an origin story. And every single startup has a moment that they point to as their beginning. And every founder has a purpose that drove them in the midst of all obstacles. THAT is The Startup Story. *


James McKinney: Hello everyone and welcome to another episode of The Startup Story. Before we jump in I want to read a listener review from Arlie K who gave the show a five star rating and wrote: "Empowering. James nails it every time. Every single episode features inspiring conversations and actionable takeaways that leverage to level up. If you are currently an entrepreneur or want to be one in the future, this podcast must be part of your content diet." Oh man, thank you so much Arlie for this incredible review. The only thing I would have added to the review is your URL or some way for people to reach out and contact you. That way I can plug whatever it is you're working on as a way of saying thank you for taking time to write this review.

In fact, for everyone listening that is how you are able to advertise your business or brand on The Startup Story for absolutely free. All you have to do is leave a written review on Apple Podcast and when you do, make sure to plug your brand and include a call to action for my audience. That way when I read your review in an episode, and I read all reviews, your brand, URL, or social media account will be advertised to my entire audience. It's just my way of saying thank you for taking time to write your review.

And one last thing before we jump into this week's episode, next week we will be releasing The Startup Story of Clay Alexander, the founder of Ember. To hype up the release of his episode Ember is giving away three sets of their Ember Mug 2. For those who are not aware of Ember, Ember is the very first temperature regulating coffee mug so your coffee hits the perfect temp and holds the perfect temp until the very last sip. You can enter to receive one at thestartupstory.co/ember and of course, we will include a link in our show notes for easy access. You do need to enter before July 9th though so make sure to visit thestartupstory.co/ember as soon as possible. All right, now let's jump in to this week's episode.

My guest this week is Jason Y Lee, founder of Jubilee Media. Jubilee Media launched in 2010 with the goal of creating a movement of empathy and connection. While most media brands play for entertainment and divisiveness, Jubilee is desiring to swim against the current for human good. In this episode, Jason shares openly and honestly about the personal journey he went through to understand what it was that he knew he was supposed to be doing with his life. I mean he had an incredible job working for Bain Capital at the time, and his original cofounder of his first venture which kind of preceded Jubilee Media was his brother, who was a staffer for President Obama. To make a career decision like leaving those positions, well as he explained it to his mom, we're leaving to create videos for YouTube, he had to be all in with this pursuit and this purpose. Yet, like so many entrepreneurs you never really learn how all in you are until it all starts unraveling. And Jason shares all of it with us in this episode. But before we get to the unraveling, we need to step into the way back machine and understand how it all started.


Jason Y Lee: Honestly, if you had even asked me what an entrepreneur was in high school, or even in college, it wasn't something that I was super familiar with to be honest. It's because I grew up in Overland Park, Kansas and both my parents were professors, so very much in our household a lot of the focus was on academics. One day, you got to go to a great college, you have to get a good job, maybe go get your PhD. That was really what was focused upon. I didn't have really an understanding of what it meant to be an entrepreneur, nor did I think that was within my realm or within something that I could even consider as a career path.


James McKinney: Now you're Korean, correct?


Jason Y Lee: Yes, Korean American.


James McKinney: So were you parents born here?


Jason Y Lee: My parents, no. They immigrated to America in 1986, so my parents immigrated here as grad students.


James McKinney: As grad students, so you were born here.


Jason Y Lee: I was born here.


James McKinney: The reason I ask that question is I mean we've had almost 130 episodes, and I would probably say conservatively 10% of them have some level of immigrant tie into it, and the immigrant story is so fascinating to me because when one thinks of the immigrant story the way out, the way to success, the way to resources and opportunity comes through academia. It just seems to always follow that narrative. And so when we think to your story, even though you didn't have the vocabulary of entrepreneurship things were happening. We're talking late 90s, early 2000s, lots of things were happening within that world. Your parents knew what was taking place in we'll say technology and media and everything else, but being so grounded in the reality that academia is a way out for success was that part of your upbringing? Where it was you were going to go this route?


Jason Y Lee: Absolutely. I mean it's really interesting because in some ways my parents kind of I think blazed a really important trail for me to see what it meant to step out and encourage, and pursue your passion. They came with a dream, literally a suitcase and a dream, to America believing there would be a better future for themselves. And then they ended up, their plan wasn't necessarily to stay in America, but once we were born - my brother and I - they said you know what this is a better place for our kids to be raised. It's ironic though because coming as immigrants to America, once they saw kind of the space and how people ended up building lives, they really pushed me and my brother toward very stable careers. Oh, you should become a doctor or a lawyer or an engineer. That's kind of the stereotype from a lot of immigrant parents.

And the reason is because I think that they went through so much tumult and so much struggle honestly to come to America but also set their roots, and having a lot of uncertainty kind of growing up financially as well as with career planning that they wanted us to have as comfortable or as effortless a journey as possible. I think that's why they pushed us in that way, but I think in some ways when I look at my parents that's who gave me a lot of the courage to kind of recognize wait a second there's a whole other journey that even my parents are not wanting me to go on, but watching their life I am interested in more, if that makes sense.


James McKinney: Oh, I love it. I absolutely love it. There's so much about whether again you are born here in the states or you move here to the states, the idea of what security and resource looks like, and then how that changes from the generations. So coming to the end of high school for you, what was your plan? What did you think you wanted to be at that point?


Jason Y Lee: You know I wasn't really sure. I knew that I had an interest in business actually. That was something that I really enjoyed. Even though my parents really, again, wanted me to become a doctor I was always very squeamish with blood, so I think that was very quickly crossed off the list. And I ended up in high school applying to Wharton, to undergrad business school at University of Pennsylvania. When I was accepted it wasn't like oh this is my path, this is it, I just thought that this would be really interesting way to start my career. Or like hm, this seems like a very reputable school and a great… everyone seems to respect it and really think highly of it so why don't I go there. Then it's funny, when I got to Wharton at the time I graduated in 2009 but at the time everyone at Wharton, at least all my peers, wanted to become one of two things: they wanted to become either a consultant or an i-banker. I had no idea what either of those things were, but to be honest I just felt that pressure to say yeah I want to do that too. That's kind of what started me on my path that way.


James McKinney: Now again back to the idea that your parents wanted you to be a doctor or what have you, consulting is so very different. If I'm not mistaken, was consulting that leap, that first step out of college for you?


Jason Y Lee: It was, yeah. It's interesting. Again, I graduated in 2009 and I had gotten a job offer from Bain and Company, which is a great management consulting firm. But because we had graduated right at the height of the recession, a lot of my friends, a lot of my peers actually lost their offers not from Bain but from other kind of banks and consultancies. And even from Bain they kind of sent a message saying you know what we actually don't have that much work right now. If you want to take six months we'll kind of help support you or give you a stipend or travel or do non-profit work or do whatever is exciting to you. I actually spent the first six months out of college in Shanghai to do social enterprise work.

So that was actually a really, at the time I was pretty nervous that I would not have a job waiting for me, but on the other hand I think it really opened my eyes to how much flexibility and how much kind of privilege I had to explore different things. I spent six months in Shanghai and later I ended up spending some time in Africa as well with the Clinton Foundation, and that was all kind of supported by Bain.


James McKinney: What was taking place in your personal life that that was the decision in how you were going to use that period of time, versus anything else that could have been an opportunity?


Jason Y Lee: You know it's funny because I think my entire life there was always just these conflicting goals. On one hand, my parents had always raised me and my brother to believe that we had to make a difference in the world, and we had to do something that was positive, and at least create a change. On the other hand, I had this kind of very clear stepladder towards success. Go to an Ivy League school, go to a consultancy, maybe eventually become a private equity or a VC, and it was just so clearly laid out. I think that there were little packets where I started to find opportunities to do more of the former than the latter. For example, when I was in college I had an internship at the department of the treasury which was considered really prestigious and really cool. That experience was pretty interesting.

To be honest, actually it wasn't interesting. It was good on paper but I wasn't learning very much, but that summer actually my brother was working on the Obama campaign. This was the primary, so this was 2007 when he was senator Obama, when no one knew who he was, when he was 30 points down in the polls in New Hampshire, and he said "Come out to New Hampshire. This guy is going to win." We got to see what it meant to build a movement and to see crowds go from 200 to 2,000 people to 20,000 people. So all these little experiences I think for me planted the seed of wait a second, when you kind of are excited or passionate about a cause you can actually do quite a bit of difference. As I was coming out of college, just to answer your question, sorry apologies for the long answer-


James McKinney: Oh, I love storytelling so don't worry about that.


Jason Y Lee: … it was, it's great, I've got this kind of stable job that my parents are really proud of me for but I'm going to take every opportunity I can to see what else is out there, and see if I can make a difference, or see if I can learn something interesting.


James McKinney: Throughout your story you've mentioned your brother a few times. Now, again not to have a spoiler alert moment but you do end up cofounding Jubilee with your brother. So prior to that though, how tight were you with your brother throughout your entire journey? And really was that cofounding moment inevitable?


Jason Y Lee: Yeah, that's a really good question. My brother and I were almost inseparable growing up, and the reason was because as I mentioned my parents were both grad students when they first came to the US. So most of my childhood, I just remember my parents being students, meaning they would have to be going to class. They were like taking us to class or taking us to the office, things like that. And we actually had to move quite a bit around the states. So I was born in Seattle and moved to Jersey. We lived in Michigan, Texas, we lived in Kansas. But for me, my kind of constant friend right because I always had to make new friends, was my brother. I think we always kind of stuck together in that way. Having an older brother I think go and be, honestly the tip of the spear in a lot of ways helped me in my journey because I had a lot of comfort knowing hey, these are some of the lessons that I'm learning from him. Every time I got into a new school or a new grade, a lot of the teachers were already familiar with me because they had my brother in class. So I wouldn't say it was inevitable that we would work together, but I would say that we always had a really close relationship.


James McKinney: That's awesome. I love it. So you come back from Shanghai and I assume Africa following that, and you now are working at Bain. So are we saying late 2009, early 2010? Where are we at in the timeline?


Jason Y Lee: That's right. In about January of 2010 was when I started working as a first day CFA in New York City.


James McKinney: And how long were you at Bain for?


Jason Y Lee: I was there for about three years in total.


James McKinney: Three years. And when you think back to those years, again every season sets us up for what is to come next. It shapes us in some way. It gives us a perspective. Maybe it's a narrowing perspective and we don't like it anymore, we want to move on to something else that's a bit broader. What was the Bain season for you?


Jason Y Lee: Oh my gosh. I always would say I knew that when I got to Bain I didn't want to do consulting for the rest of my life. But I also felt like that time and that season was invaluable. I was surrounded by, and this was the case when I went from high school to college as well. When I went to college I was just surrounded by so many brilliant people. And not just intellectually smart, because I think that was maybe a given but there were just all these people with just passion and almost a belief that they could do whatever they want. Growing up in Kansas, that wasn't a belief that I honestly had. I just thought oh, you know, if I just try to work really hard I can maybe have a stable life, have a family, and be happy. I got to college and I had met friends who were like one day wanted to become a Supreme Court Justice or one day wanted to become a VC or one day wanted to become the President of the United States. I literally was sitting here thinking man, one day it would be really nice if I could make a six figure salary and own a home. I thought these people are brilliant, but also they're not that smart that this would be inconceivable.

As much as I felt that when I went to Penn, when I went to Bain it was even more so in that I think it was just such an eclectic group of people who thought so differently. I distinctly remember I had a good friend Zack who we were coming in as first AC, and every evening I would just be like, "Oh, let's go grab a drink or let's go grab a slice of pizza." And he'd be like, "Actually, I'm working on my startup that I founded. I've got five employees already," and I just thought wait a second, you can have a startup at 19 years old or 18, whatever age we were, now 21? And I think that kind of just blew my mind. So that's what I always remember, and that's what I've taken from that time is I've still got so many close friends and people I admire and mentors who have helped me along my journey.


James McKinney: You know that type of environment, it's life giving for so many because we're constantly challenged in a lot of cases encouraged, and I say encouraged from the actual meaning of the word of placing courage inside of one, not from this Hallmark moment, but like we're actually encouraged by being surrounded by those people that are "better" than us, they lift us up in some way. Why would you leave?


Jason Y Lee: You know, that's a good question. I think for me, and this is not a knock on consultants because I actually think that they're so vitally important, and so many of my friends are still working as consultants, but for me what I felt like was at Bain we had this experience of being able to parachute into companies, think about the most difficult problems, try to solve them, and kind of leave. But I always felt like we were not building ourselves, that we were trying to assist others. And I had this nagging question I think in my heart which was man, what would it be like if I had the courage to build my own thing, if I had the courage to even live and die by my own company? It wasn't something that was like a light bulb moment at the time, but it was something I think I knew in my heart that what if? And I would always wonder or be maybe afraid of that question later on in my career if I had never done something. So I think that's why I knew that I wouldn't be a consultant forever.


James McKinney: Before we continue on with Jason's story, I went to check in and ask is hearing directly from founders like Jason bringing value to you? Do you believe founder direct content hits differently than from some self- proclaimed thought leader? Well let me ask you another question. When I say the phrase content marketing what comes to mind? Maybe you hunch your shoulders forward a little bit out of frustration because it feels like a constant chore that never delivers results. Or maybe your internal temperature rises because you've created so much content, but it has never driven the business success that you thought it would. Either way, I am fairly confident the thought of content marketing is viewed more with disdain than it is excitement. So with that in mind, wouldn't it be helpful to learn proven tactics directly from founders that have executed well in this area? Even more so, would having their tactics delivered to you every quarter be helpful to you as you build your business? That is the experience and knowledge sharing that is delivered to you each quarter when you become a Grindology member.

Grindology is an entrepreneurial subscription and it ships every quarter full of resources to help fuel your grind and your hustle. Now what's included in your Grindology shipment? First and foremost, every single Grindology shipment will include a copy of the Grindology tactical manual. Every single issue of Grindology will be chock full of real tactics from real business builders, not journalists. Within the pages of the Grindology manual we will be delivering to you tactics and strategies you can integrate into your business immediately. How great would it be to receive proven tactics on how to leverage existing content that you've created to drive new business and deliver new revenue? Or how about hearing operational tactics used by a founder that saw nearly 400% growth in one year and he directly attributes to his content marketing efforts? Or even better yet, how about hearing from a founder that actually stopped creating curated content and started documenting everything, and they single handedly believe that saved their business in 2020? Tell me those founder direct tactics wouldn't be helpful? Well those are the exact types of tactics that will be found in each issue of Grindology. Like I said, real tactics from real business builders.

Our Q2 issue is now available and we focus on content marketing. You can access it today at grindology.com. Everything about Grindology is about helping to fuel your grind and your entrepreneurial journey. So visit gridnology.com today to learn more. And of course we'll include a link to grindology.com within our show notes for easy access. Now let's jump back into our episode with Jason Y Lee, founder of Jubilee media.


James McKinney: You bring up a good point about consultants. I don't know if everyone has an understanding of what the life of a consultant is, and we're not going to cover that in this episode, but there is something to be said about having theories on how to fix problems within businesses, then actually executing and being able to do. As you were answering that question, the first thing that came to mind was that old adage "those who can't do teach." Right? Do consultants fall in that category? Are they consultants because they can't execute? What are your thoughts?


Jason Y Lee: The way I think of it is as a muscle. I think that actually consultants are building this muscle of problem solving and critical thinking that's invaluable to actually the entrepreneurship journey. And that's why I actually think some of the best founders and entrepreneur s are a form of consultants, because literally as a new consultant every three months, every six months you are put into another scenario where the company hasn't been able to figure out how to solve this problem and they're asking for help, and you as a young person are coming in saying, "Oh my God, okay I've got to help figure out this answer." But you start to recognize okay how do I think through it, even if there's a framework. How do I at least use my brain and my kind of creativity, or my training to figure these things out? I wouldn't necessarily, I kind of think of it as consulting is a great training ground, and some people have a separate part of them that is maybe having that desire or that creativity to say I've got an idea, now let me go pursue it. So I've seen so many of my friends from consulting go start companies. I've actually seen a lot of folks go start a company, go back to consulting, and actually go back to starting companies. I think it's a great training ground is the way I would think about it.


James McKinney: Interesting. I could see accelerated learning taking place for sure because you're seeing so many different problems. I guess technically all you are seeing are problems.


Jason Y Lee: Totally, and you're working with different teams. Every time you're solving a different problem, you're jumping into another team of four or five, six people and all of them are brilliant and smart, and have so much experience. So it definitely is your growth is on hyper drive I would say.


James McKinney: I love that. Absolutely love it. So how do we get to Jubilee then?


Jason Y Lee: Yeah. You know I find it ironic I'm even on this podcast because again, it wasn't one day I'm going to be an entrepreneur, what is my idea, what is my opportunity? It's something I really stumbled upon. It was actually my first week at Bain. Again I started late, so I started in January. My second day on the job was my 22nd birthday. I distinctly remember because it was my 22nd birthday, but that afternoon while we were sitting in training, we started seeing just horrific photos and videos of the Haiti earthquake. I remember being so struck and feeling like why is it that I'm so privileged and blessed honestly to have this job and make this money, and celebrate my birthday yet all these people are suffering? And what can I do about it? Because we didn't have very much work at the time because of the recession, I had all this time.

I said, okay I'm going to do something crazy. I believe that ordinary people can do extraordinary things, so I decided to go grab my guitar and go to a New York Subway stop to sing, put out my guitar case, and busk to raise money for Haiti which is an insane idea because I'm a terrible singer. But I just wanted to do something. I got a bunch of my friends out there with me and we had a good time. That day we raised about $80 which I was pretty proud of given the lack of talent on my end. But my goal was to raise $100. So what I decided to do is all along the way we had been just filming with a little camera. So I made my very first video and I put it online onto YouTube. I sent it to my friends and said, "Hey, we're trying to raise $100. Please watch. Please consider donating."

Within a week we had tens of thousands of views. Within a week we had thousands of dollars raised for Haiti. I think that was a bit of a light bulb moment for me, which was wait a second if I'm stepping on faith, doing something I'm incredibly passionate about and doing it for a good cause we can really mobilize a lot of people, do a lot of good. So that's what started Jubilee Project which was actually the nonprofit that I created. Over the next two or three years, actually the entire course of my time at Bain, nights and weekends were really committed to making more videos and content to raise money and awareness for other causes.


James McKinney: So real quick, just to make sure I understand this. So January of 2010 I believe that's when the Haiti earthquake was. That's when you learned clearly that you are not a main stage performer.


Jason Y Lee: That's right.


James McKinney: But you feel compelled to do something. And out of that launches a nonprofit called the Jubilee Project. What was your objective with that?


Jason Y Lee: You know it's funny, I never really thought that I'd be creating more content. When I first launched the website I think I said this is a space for people to take a leap of faith and to raise money and awareness for other causes. So my initial vision with the nonprofit was that I would make this first video, and then maybe James you were interested in another cause like clean water, that you would make a video or you would setup your own fundraiser, and then this would be a space for other folks to be doing it. This would be just like something that I helped start, but really that I wasn't really doing much of. What I didn't realize at the time was I'm like, "Everyone make your videos and I'll upload them." Weeks past, no one made a video, and I realized okay, seemed like the barrier of entry to make that first video is quite high. So I said why don't I make a second video? And I made a third video, and then that's when I got my brother involved, and one of my best friends Eric involved. And that's when we started Jubilee Project, the nonprofit.


James McKinney: So let's talk about the business side of that nonprofit. Was this a standalone platform that you were wanting people to upload videos to, like a Go Fund Me type thing?


Jason Y Lee: It was more of think of it as a pretty basic website that just, all the videos sat on YouTube but that we would pull all the videos onto its own page, and we would have it tracked. But truthfully, because we all had our fulltime jobs I didn't think of this as a business venture. It wasn't how are we going to make money, how are we going to sustain ourselves. It was literally wow, this is really fun and we're getting to do a lot of good. Let's just do more of it. It slowly kind of grew. I think that's something I always tell a lot of young entrepreneurs or young folks who want to get into entrepreneurship is if you had told me from the very beginning, "Hey, this is the top of Everest. Now get there. That's where you want to go," I would be like oh no, I don't know how to climb. Whereas here it was oh wow, this is kind of interesting, I'm really enjoying these first 10 feet as I look around. Maybe I'll take another 10 steps, and slowly recognizing wait a second, I'm on this path of a mountain, not let me get there. That's why I always kind of say that I stumbled upon the building of Jubilee, what ended up becoming Jubilee Media.


James McKinney: So how did the Jubilee Project come to an end, and how did it morph into Jubilee Media?


Jason Y Lee: Yeah, that was a whole journey as well. We started Jubilee Project, the 501(c)(3) in 2010, and again myself, my older brother Eddie, and Eric. About two and a half or three years into it, we started to get a lot of traction. We were getting maybe a couple hundred thousand subscribers. We were raising hundreds of thousands of dollars for nonprofits, and we were asked-


James McKinney: Let me pause you there real quick then, just on that traction moment. Was there an event, was there a video? Where did that begin to take place? Because that's not a small number.


Jason Y Lee: Right. You know, it was a bit of a snowball effect. Small campaigns of thousands of dollars became tens of thousands of dollars, and then as we just kind of grew it wasn't every single fundraiser was popping off and going crazy. It was every once in a while there was a certain cause that really resonated, or a certain video that really resonated. We had a video called Love Language that ended up getting five or six million views. That was shocking to us because up until then, it had gotten 50,000 views which we were really excited about to be honest. It got to the point where we said wait a second, there's really something here. At the time, we were getting asked to speak a lot at events, kind of like this but in front of students. They would say, "You know, what gave you the courage to do Jubilee Project?" And we'd say you've got to follow your dreams. Meanwhile, every Monday morning I'd be back in my cubicle working as consultants, saying oh my God I'm such a fraud.

It just became this moment where I started to recognize wait a second, there's an opportunity here and I don't want to miss it. It was the light bulb moment really is there's a quote, I don't know if you're familiar with Bronnie Ware. She's a palliative care nurse and she was the woman who was interviewing a bunch of folks who were on their deathbed, as they're about to pass. She would ask every person, "Before you die, what is the biggest regret that you have in your life?" People would say things like I wish I spent more time with family, I wish I travelled more. But by and large the biggest regret that folks would have as they were about to die is people would say, "I wish I had the courage to live a life true to myself, and not the life others expected of me." When I heard that I was like wow, that's my life. Not that I hated consulting, not that I hated what I had done, but I realized wait a second, I was doing this largely because I thought that's what I was supposed to do. I thought that's what would make my parents the most happy. I thought that's what a lot of my mentors, my peers expected me to do out of Penn. That's when we decided that we were going to quit our jobs and leave to do this fulltime.

I left Bain and luckily that was a pretty easy transition. My brother was at the Obama White House at the time, but he left that job. And Eric, our third friend, was a med student at Harvard. He left Harvard midway through and we left to start doing this nonprofit fulltime. When people would ask us, we'd say we're going to make videos on YouTube as a nonprofit and people thought we were insane. They thought we were crazy and it made no sense.


James McKinney: There are so many questions that come from just this season of your life, and the first one obviously, your parents have been seeing your success with the Jubilee project throughout the years that you were developing and building it, and I would assume they were fine with it being a side hustle.


Jason Y Lee: they were.


James McKinney: How was that conversation when it came time to quitting?


Jason Y Lee: Yeah, it didn't go super well, I'll be honest James. Again, there's two sons of immigrant parents, and they're so proud mind you of the journey now. Because they're like you've gotten through the tough stuff, you've now got a job on Wall Street. I wasn't technically on Wall Street, but they would tell everyone I worked on Wall Street, Eddie is at the White House. The fact that we quit around essentially the same day just gave them a heart attack.

I call my mom, I say, "Eomma, I love you." "I love you too. What's going on?" "Oh, I just quit my job." She goes, "Eomeona," which in Korean is like oh my God. "What are you going to do?" "I'm going to make videos on YouTube." " Eomeona." My brother calls the same day, and it's like, "Hey eomma, I love you." "I love you too, my favorite son. What's going on?" "Oh, I just quit my job." "Eomeona, why? You too, what are you going to do?" "Oh, I'm going to make videos with Jason on YouTube." Like oh my God, because it didn't make any sense. Just rationally speaking, it didn't follow the trajectory of our careers, and no one at the time would have said, "Wow, this is a really good step for you guys. This makes so much sense and I see the dots connecting."

It was not only that we were making videos on YouTube, which now I think you can kind of see a pretty good path to success, and that's a dream a lot of young people have, but at the time it wasn't as lucrative or very few people were able to really sustain their lives on YouTube. Not only that, we intersected that with being a nonprofit so in my parents mind, they were like, "Oh, he is doubly committed to making no money." Right?


James McKinney: He's all in on being broke.


Jason Y Lee: Exactly, exactly. Maybe we emphasized the doing good parts too much, and not enough about the stability and how do you want to live, and eat.


James McKinney: That is so funny.


Jason Y Lee: But yeah, I think that was obviously, it was both a terrifying time but honestly it was such a life-giving time. It was really exhilarating. The reason why I had the courage to do it honestly was because for two reasons. One, for two and a half years, I was doing this already. I had built something that I was already really proud of. It wasn't just I have this idea, it was something that we had been working on from 6-12 am every day. Not only that, I also had my best friend and my brother to do this alongside. I think when you've got an amazing team that you love working with, that's just the extra kind of blessing in a lot of ways that really pushed me over the edge.


James McKinney: So everyone quits their job. What is… again, your brother was at the White House in DC, you were in New York, what was minute one? Now this is it. Do you guys come together? Do you stay in separate locations and continue remote? What is step one for you guys?


Jason Y Lee: My brother had a 2003 Honda Element, and we all met in DC. It's funny actually, this is a random story, but when you leave the White House every staffer who has worked for the administration gets to say goodbye to the president actually, so that's really cool.


James McKinney: That is cool.


Jason Y Lee: My brother said, "Hey, would it be okay if I brought my family?" So he invited me and then he invited Eric. We just said he's our cousin, and we all walked in.


James McKinney: Yeah, because the White House can't verify that at all, right?


Jason Y Lee: Right, right. Yeah, that is a really important question. I'm not sure how we got through that. But we made it in and I remember President Obama at the time asking Eddie, "What are you going to do?" And he said, "Oh, we're going to be making videos on YouTube for a good cause." And I remember the president saying, "Hm, that's interesting. But you know I've always believed that young people can do anything they set their mind to." And we just kind of saw that as oh my God, President Obama said this is a great idea, right? But we packed our bags all then right after that actually, into that Honda Element, and we drove across the country to LA. The reason was we just kind of always had thought that's where storytellers were, and that's where film is being made. Even though we had just convinced their son to quit Harvard, Eric's parents were really generous to say, "Hey, we've got a bedroom for you that you can stay the first six months or year." That's kind of what was our plan. We were going to move out and see what happened.


James McKinney: That's awesome. So a nonprofit was the objective. Again, let's put a year on this real quick, what year was this moment in LA?


Jason Y Lee: So this was 2012 or 2013 or so, yeah.


James McKinney: 2012 or 2013, so a lot has happened since then. But you were a nonprofit so from a business model perspective was there a fundraising element to it for you guys? Were you out there trying to get people to donate to the Jubilee Project or was it based off of proceeds?


Jason Y Lee: Yeah. It's funny because I had gone to business school and I worked at Bain, but I hadn't thought of a business plan for how we would operate as a nonprofit , and this was a fallacy that I kind of believed which was oh, we're doing nonprofit work and therefore we can't make any money. That's just simply not true. But it's interesting because we actually said you know what, we're not going to take any of the funds from Jubilee Project because we care so much about the cause. Luckily, we were in a place where we had saved enough from our careers that we had a nest egg that we could just kind of live off of for at least the time being.

So first couple of years, we actually took no salary. We covered our expenses, just gas and food through the nonprofit. Then everything else went back to the various causes we made. It was a really kind of safe time I would say to just learn and grow. Similar to Bain, it was just our kind of training ground for learning how to do storytelling, and how to make digital content, and how to make videos and films which was not something that I had been trained on ever. But just trial and error, a time of intense creativity working 20 hour days, not sleeping much, but just having a great time doing it.


James McKinney: Let's talk about the creativity side of this. Thus far in your journey, I haven't seen anything that would wave a flag like oh, this guy is a creative mastermind you know? And I'm not saying it in a disparaging way, but it has been very structured, which is the creative mind tends to not be. So how did you lean into this creative side, the storytelling side, based on what we've really heard a very academic upbringing?


Jason Y Lee: Yeah, it's funny because even though my parents were so focused on education, the one vice that my dad always had was films. So growing up, I just remember even as a third grader or fourth grader, my mom would always get mad at him but he would bring us to every film that was… There were always free screenings on campus, so any time there was a free screening he would just walk us in because we were kids, and we'd sit on his lap to watch the movie. So we were watching all sorts of films that we definitely should not have seen at that age. But I remember falling in love with stories. The idea of becoming a filmmaker was not in any where in my galaxy or my universe, but I think I could start to discern what made a good story. I always had thoughts about why a film was good and why a film wasn't good.

So I think in that way I had kind of this latent understanding of storytelling and filmmaking, and then when we started doing Jubilee Project it wasn't, "Oh, now we're filmmakers." It was kind of this is a really new, interesting medium for us to explore. What if we could learn from some of the best here in LA? So we would actually kind of work with other filmmakers, storytellers, and try to get as many lessons as we can and that ended up becoming kind of our film school so to speak. Even filmmaking, you know I always admire folks like there's a film school here at USC, like folks in high school who know their passion and are like, "That's what I'm going to do." It wasn't something that I had, it was just wait this is really interesting, let me continue to do it. Slowly but surely, I think that 2010 to 2017, that entire period was really me doing Jubilee Project, but it was also me learning how to make films and tell stories.


James McKinney: I love that, absolutely love it. At what point does the Jubilee Project become Jubilee Media? And what was taking place that prompted the shift?


Jason Y Lee: Yeah, that's a good question. It's interesting, around 2015 or 2016, we had been doing this for a couple of years now fulltime. Both Eddie and Eric, the guys that I started Jubilee Project with, started to kind of feel like they had other things they wanted to explore and do. Eric actually first went back to med school. And that's always the thing is like when people say, "You guys are so courageous about leaving," what I always tell people is the truth is there's always this safety net. If I had gone back to Bain or if I had gone back to my friends who were working in business, the truth is I could have gotten a job again. Sure, my tail would have been between my legs and I would have felt embarrassed perhaps, but I was incredibly fortunate or privileged in that way. Eric went back to finish med school mainly because his parents were saying, "Please, please, please just get your degree and then you can do whatever you want." So he went back to finish. Eddie actually met his now wife, they fell in love, and they wanted to do stories together, and they wanted to do kind of more faith based stories. So that's what he went off to do.

And actually that was a really… that ended up becoming really a tough time for me. Because suddenly I was out there with my best friends, they both left, and I was sitting here by myself running something that I loved but I felt like wait a second, I'm all alone here. I describe it as I felt like I was the last man standing on a ship that was sinking, and everyone else had left for greener pasture. So it kind of put me into a place for a couple of years actually, 2015 and 2016, I got I wouldn't say I was depressed but it really made me critically reevaluate my life, and who it was that I was, what is it that I wanted to do, and was I even happy in the first place. At the time, it was all the things that I thought were really important were stripped away. All the subscribership or the viewership numbers, even the money that we had raised. I was kind of like left with myself just looking in the mirror saying, "Okay, Jason. If you are not afraid, really this time not afraid, what is it you want to do?"

And during that time what I recognized was wait a second, I love storytelling, I love the idea of being able to inspire young people and a generation of people to do good, but I don't think that I want to spend my life raising money or awareness, or I don't want to spend the rest of my life in the nonprofit sector, because I just had some personal frustrations with how much change I could create and how slowly sometimes things moved. That's when I started to imagine what would Jubilee look like, or what would a company look like let alone Jubilee, that existed in the for profit space, that existed essentially to do that, and how would it be formed, and what would I do if I were to create a new company from the ground up. That's when I decided you know what, and very, very creative name, I said we're going to call it Jubilee Media. That's when I started to dream up and create Jubilee Media, which was a separate entity now.


James McKinney: When you think back to that decision, what was Jubilee Media to you and how is it different than what it is now?


Jason Y Lee: When I was first going out to talk to mentors and folks about even investing in Jubilee, the thing that folks would say, actually one of my leading investors would say is, "Oh Jason, this is the nice place." I was like, "Oh yeah, that's exactly…" Buzz Feed at the time was really, really killing it and I think Vice was really strong player, and I felt like these are such great media outlets but what if there was one that was dedicated towards empathy and humans, and more about understanding each other and less about just entertainment. That was always the vision that I had. But I also knew that if it was just too earnestly good it wouldn't be interesting to watch. So it's this kind of intersection between empathy and entertainment that was for young people. I felt like there was a huge white space for that that no one is really trying to capture.


James McKinney: That's an interesting statement you said, if it was too earnestly good it would be hard to capture attention. Maybe I misstated that whole thing.


Jason Y Lee: No, no, that is how I felt. The reason was with Jubilee Project that was my attempt that hey, this is so important. Every one of these causes was so important. Clean water, save the children, education, sex trafficking, so many important causes that I was very, very passionate about. But what I recognized was there was a fatigue in the response. In some ways, we had to start earlier to bring people along that journey. So the way I think about Jubilee Project was that we were just trying to force feed people broccoli. And some people loved it, but a lot of people said you know what I can only take so much broccoli. With Jubilee Media it was this idea of what is peanut butter covered broccoli look like? That it has some of that goodness but it also is something that people are excited to eat, and will have an appetite of their own for. That's the way I think of the content that we make with Jubilee media.


James McKinney: So now you had mentioned the idea of asking people to invest, so now you've changed the legal structure. Jubilee Media is a for profit entity. So was the vision from minute one investment capital? And the reason I ask this question, my second episode happened to be with Larry Namer, the founder of E! Entertainment Television. Hearing his startup story to founding E! is amazing, but one of the things that he said that I'll never forget is back then it took $60 million to startup a media network. Now, you can do it with your cellular phone. It's a different day and age. So when you think to the Jubilee Media side of it, how were you looking at it from a capital perspective? Were you wanting to go grass roots or were you like I want to try and come out the gate with a couple million dollars?


Jason Y Lee: Yeah. I think there was a huge paradigm shift to when I started Jubilee Media. I had thought to myself this won't be worth it unless this could be a billion dollar company one day. It sounds audacious but it was that's the level of impact that I would hope we'd be able to make one day. What if we could become the Disney for empathy? As such, I said I would rather go to the moon or I would rather die trying, rather than kind of plodding along. That's the way that I felt towards the end of the Jubilee Project years. So I said you know what, let me raise some capital.

We ended up raising just under $1 million I would say for our first round. It wasn't like a crazy amount, and I think to your point it was because with digital media the costs are lower. But to be honest when I first started raising it was a big struggle. A lot of people either one, didn't get the thesis, didn't understand what I meant when I said what if there was content that was both empathetic and value driven, but also incredibly entertaining. They said that doesn't make any sense to me, what do you mean. Other people who said media is just such a difficult thing to get traction, to grow, to develop IP, it's not a space I want to be in.


James McKinney: Interesting. I want to, your language changed very distinctly when you talk about your mindset going into Jubilee Media, and yet talking about the ending days if you will of Jubilee Project and where you were at because your friends had gone on, you're the last man standing on a sinking ship. You talk about those two years of just processing the things that are taking place. Can you think through that moment when you're processing what is it you want with your life? And the reason I ask this question is because hearing the language that you use talking about I'm going to go to the moon, I'm going to go all in on this, that is a very empowered language, a very empowered position. Obviously there's a lot of enthusiasm and adrenaline that goes into starting a business as well, but having come from a place where again, to use your words, last man on a sinking ship, sometimes our response is I just need to go lick my wounds, get a job, just kind of recover a bit, take it easy, I don't know if I want to do this again, I don't know if I can. There's so many different ways we can go, but you went the I'm going to call it the warrior way. You went the way like this is what I'm going to do now, and this is how different it's going to be. What took place with you?


Jason Y Lee: Yeah, it's a really good question. It's something that I haven't talked about very much or even unpacked that often. Even though, you know I talked about that quote about living a life true to myself and not one that others expect. I felt like when I was leaving Bain to do Jubilee Project that was that step. I thought I was all in. I thought I was going to the bottom loophole. When I was by myself with Jubilee Project and everyone else had departed, what I realized was maybe I was ten feet down, but actually the depths of that water was the ocean.

I hadn't done the full journey all the way down to the bottom as I needed to, to understand what it was inside my heart, what is it that I was being called to do. I'm a person of faith, so a lot of that is was even me thinking about my relationship with my faith, thinking about what am I here on this earth to do. Why do I have a lot of the privileges and opportunities that I've gotten, am I making the most use of these gifts or this talent or this time that God has given me? That's I think where I recognized one is that this kind of value of myself. I know this sounds kind of "woo-y"-


James McKinney: No, this is great.


Jason Y Lee: I think what I had to remember was inherently that no matter what I did, that my value wasn't going to be derived from my accomplishments. That whether Jubilee Project succeeded or failed, whether Jubilee media succeeded or failed, it didn't matter because who I am, I am valuable, I am loved. That's a full stop. I think knowing that gave me so much courage.


James McKinney: I'm so glad, one, thank you for being vulnerable enough to answer that question. I just sensed there was something that took place because of how bold you came out of those couple of years. I'm so thankful for the way you answered. And for all those listening, I want you to hear what Jason said there. We talk a lot about our value is not in our product or service, and we have to detach our personal value from what it is we're working on. But one of the things you hear so much in the media space or the self help space, or whatever you want to call it, is that our value is not founded in the failure or the challenge. But let's be very clear too, our value is not founded in the successes either. It is completely detached from who we are. Our value is autonomous and valuable. If we say that our value is not based on our failures, well then our mind says well great, it's based on our successes so therefore I've got to be massively successful. No, no, your value is autonomous. You cannot be attached to either. It is absolutely not.

So I'm so thankful for you to say it the way you said it, Jason. I'm appreciative of your authenticity and transparency because I want every single one of my entrepreneurs, whatever stage you're in. maybe you're the frustrated entrepreneur who has been at this for so many years and just continues to fight up hill, and cash flow and payroll are always things. Or maybe it's the wantrepreneur who has got a book full of dreams and ideas, but you've got some reservation as to why you aren't going to move forward on this because of again public perception or where you place your own personal value. I'm so thankful for the way you responded in answer to that.

So now let's talk about Jubilee Media. So for those, you've said a few different sound bites and a few different ways, but for those who have never heard of Jubilee Media and this is their first introduction to it, can you explain what Jubilee Media is for my listeners?


Jason Y Lee: Sure. Jubilee Media, we are a digital media company. We exist to create content, so largely video right now but eventually film and television, that forces us to evaluate our identity, to evaluate our humanity, evaluate our connections. And that aims to bridge us more together than to divide us. Our vision ultimately is that we want to create a new culture of empathy, particularly for young people.

We're really excited because we've been able to grow an audience of folks that believe what we do, and we're seeing an amazing response so far.


James McKinney: I love that. Can you, what would you consider the start date for Jubilee Media?


Jason Y Lee: It would be about mid 2017 is when we really started… actually October is when the legal… It's so funny because there's so many different stages of me saying okay, now I'm ready. I had to create all these new founding documents and all that. I actually believe that's October in 2017 is when that became official.


James McKinney: October 2017. So now we're talking about a media company, which is again we automatically think to Disney, we think of media and we think IP catalogs, and we think all the things. When you think to your launching point, better yet when you think to all the ways in which you pitch for investors to Jubilee Media, what is that IP catalog look like? Is it something that you maybe didn't even recognize that you had to build before investment capital? Or maybe you didn't? What does it take to build a media company these days?


Jason Y Lee: First off, I didn't realize how difficult it would be before I started, but I think that sometimes there is a gift of ignorance, of I just believe we can do it. And we can and we will, and we are. But at the time, it was a couple of different theses that I had. One was that there was a big space for this kind of content that was both empathetic and savvy. That was actually the space that a lot of media would be moving towards. As I understood my generation and Gen Z, I just recognized there was such a desire for authenticity. And now authenticity is a word that's used so frequently and I think often misused but that people care who is making the content now. People care who is behind the product. I wanted us to have a media company that from the founder through its values, through every hire that we make, was in alignment with that vision. That was one of the theses that I had.

The other was this idea that if we make quality content, that's what would actually draw a lot of viewership and kind of engagement, and loyalty in a lot of ways. At the time, Buzz Feed was making 65 videos a week. I remember thinking… and they were dominating the space. I remember thinking okay, I know the way we're not going to win is by making 66 videos. In fact, with the capital that I'm raising I think I can make one video a week. Do we believe that we can make a video that is I don't want to say it's 50X better, but that brings so much value that we can eventually compete with a Buzz Feed, at least for attention and for loyalty? But that was kind of the thesis that we had.


James McKinney: That is incredible. I mean let's talk about the logistics side of this. As you're talking about just the idea of making one video a week. There's the story, there's the characters. You're now talking about writing… again, I don't know the length of some of these videos but you're talking about basically writing a show and all the things that go into it, and yet we still haven't even talked about the idea of are there themes to your content. Again, and then distribution. We haven't talked about distribution yet. Are we talking just putting it all on YouTube and the various social media platforms out there, Facebook Watch? Where do you even begin when it comes to answering some of these media questions?


Jason Y Lee: If at the time you had asked me all those questions in this way I would have said, "James, I have no idea." So it wasn't, and I had what I would call a plan but I would say that it was a very, very loose plan. In fact the 20 year plan was much easier for me to map out than the two year plan or the two month plan, if that makes any sense.


James McKinney: Makes complete sense.


Jason Y Lee: Boil it down. And what I think I knew at the time is I knew YouTube. I had spent five years doing YouTube, so that's where we were going to start. And I also knew digital. I also recognized at the time that we had to be able to move quickly and efficiently, and without much cost. That's why even with Jubilee Project we did a lot of narrative scripted stuff. We'd write content, we would shoot it out almost like a film. But with Jubilee Media, I early on made the decision we're not going to do anything scripted. We're actually going to create formats that we can put normal people into, and that the content would almost write itself. A lot of the IP would be in the format and how we brought people together. So that was something that I said let's make 10 videos. Let's not make them all the same format. Let's make 10 different formats and let's see how quickly we can put them out, and let's see if anything gets a response. That's kind of how we operated is this idea of let's quickly MVP almost these different show series, knowing that one day we wanted to have IP meaning like shows that were weekly or monthly or whatever they were going to be. But for now not having that burden, making just several videos believing that if one of them did well that we could make a second video.


James McKinney: When you think to those original 10 and your MVP where again you don't have investment capital yet, were these branded sponsorships that were partners of yours? Or just all on your dollar?


Jason Y Lee: All of it was on our dollar. Truthfully, it wasn't actually that expensive. We had basic equipment. All we really needed was space and people and creativity. A lot of our early videos if you watch them, thank God for these incredible people who were willing to say, "Hey, we believe in your mission. I'm willing to show up on your video." There was no subscribership, there was no viewership, so it was like for what? But very quickly some of the content and some of the shows that we imagined started to actually gain traction. One of the first shows that really worked for us is the show called Middle Ground. Middle Ground, when you first see it you kind of think it's a debate. We'll bring republicans or democrats together, you'll bring pro-gun and anti-gun, but the reason we call it Middle Ground is the way it is structured it's not who is going to win the debate. It's actually let's find what middle ground we have between these two groups, meaning step forward if you agree. It just ended up being such a powerful statement, I think something that we desperately wanted to see in the culture. The response was amazing. That was actually one of our first shows that really got popularity and we were starting to get hundreds of thousands of views, and eventually millions of views, and we were off to the races.


James McKinney: You're four years into the Jubilee Media journey. What has been… my mind thinks of probably 40 different challenges you had to encounter and work through. But when you think back to let's just say three of your most painful lessons, or even your most painful lesson, the one that gives you goose bumps thinking about it right now, what has been one of the greatest challenges and lessons for you in these last four years?


Jason Y Lee: Man, there have been so many. There was a time early on I remember and my now wife will tell you I was just like for a month I couldn't eat, I was like having nightmares, and the reason was we had it was around our people actually, personnel. The reason was I had always believed if we had a strong mission and values, we're going to attract strong people and we're going to create strong content, and then create a strong brand. That's actually been a huge driver of our success is we have incredible people. But I remember the very first time we had to let someone on our team go. That was really difficult, not because… surely because part of it was because just having to do that for the first time, I had never fired someone before or let someone go. I think that terrified me.

But I think what was a huge component of it was that I had felt like I had failed actually. In setting up that person for success and also in kind of the lead up to that transition for that individual. What I recognize now is how much my job is to set people up for success, and also when you're having difficultly creating a plan that really helps and assists them through figuring out if they can kind of improve their performance or not. At the time, as a first time entrepreneur, I think I just didn't have as many of those tools as I wish I had. It's something that I think I would always grapple with, like oh but I love this guy, I love this individual and he's so down for the mission, but why are we not able to make it work? I think that was always really tough.


James McKinney: Oh yeah. People are always some of our greatest challenges. Again, it's not even necessarily them, it's how we are going to lead them. It's our own… people push against some of our weaknesses sometimes, and it's like okay wait a second, I've got to figure out how to navigate this. There are so many questions that come to mind that I want to unpack. Even from a tactical level as an entrepreneur. I want to understand the capital process, I want to understand the staffing process, I want to understand the distribution side. Because again, as The Startup Story being a media company, there's things I want to be learning from you. But the one question that I feel like I would just, again because I want to honor your time too, we can't have a four hour episode, the question that I just keep going back to and I don't know if I can properly frame the question, but it's why do we need Jubilee Media now more than ever?


Jason Y Lee: Yeah, it's such a good question. The way I respond is I feel like now more than ever the world feels like it is getting more and more divided. That it's getting more partisan, it's getting more political, it's getting more difficult to see ourselves in one another. When we especially look at the media space, so many media outlets I think are benefitting and growing from this partisanship or from pitting us against one another. When you look at debates or discussions it's often not a discussion where people are actually listening or considering other people's point of views. We're actually often sitting in echo chambers and kind of just reinforcing a set of beliefs that we might have. That's why I believe Jubilee Media needs to exist now more than ever.

We exist because we want to show that we have far more in common than we might think, and that we want to expose especially young people to all different points of view, and not say that this is the right one and this is the wrong one but rather what would it look like for us to be treating each other with understanding and empathy. Acknowledging that doesn't mean we're always going to agree on every issue, but that we are all incredibly different but bring such a unique perspective to the table, and there's a lot of value in it. There's a lot of value in us learning together and growing together. I think that's why Jubilee media is so necessary, and I think that's why so many young people have starting to love what we're building with Jubilee.


James McKinney: Are there any, before give what you just said, are there areas of content or topics that you just won't touch? Or are there certain pillars that you are building around?


Jason Y Lee: You know we think of maybe the fence for Jubilee is what does it mean to be human our identity, our perspectives, our beliefs, our interactions, our connection. There are so many things that are just universally human, and that's where we want to reside. We're not really afraid of going to spaces that can be difficult and that can also ask uncomfortable questions to ourselves and to other people. The ones pace that we won't really touch is when someone is trying to advocate harm against another individual. Whether it's violence or hatred, I think that's just something we just won't platform. But by and large, we believe that everyone deserves a seat at the table, no matter how different their perspective might be. I get responses, I get 90% of our responses that we get are amazing. And people saying, "Hey I love your content. You've really changed the way I view this issue," or like, "You've really made me reevaluate how I think about this." I see that as such a huge, huge gift I guess, a huge privilege and opportunity that we have. And then we also get 10% of folks saying, "Hey, why did you feature this perspective?" or, "Why did you do this?" But I'm really proud of the fact we actually get that from usually both sides of any argument. If it's a political issue, a lot of conservatives will say, "Hey, why did you feature this point of view?" and a lot of democrats would say, "Why did you show this point of view?" As long as that's kind of balanced, I generally feel like we're in a good space because we're not for the left or the right, we're purely for info for all of them.


James McKinney: What would you tell Jason Y Lee in 2016 as you're contemplating what Jubilee Media looks like, knowing what you know today?


Jason Y Lee: What I would say to him is I would actually say probably like to take courage or have faith. So much of the entrepreneurship journey is alone. It can be such a lonely experience that even though you're surrounded by team members or even loved ones, it's hard to understand what it means to be a founder, and every day can field like each battle. But the reason I say take courage is not because Jason you've got the right idea and you're a genius, you're going to figure it out, but so much of the success of Jubilee will come from other folks who believe in a similar mission, and bringing their own gifts and their talents to what you're building. That the world needs it and the world will help grow this into something much larger. It would just be to have faith and remember that you're not that important, that you're just a part of this journey, and the success is largely due to this being necessary in the world, not necessarily because you're smart or that you're really gifted, but to enjoy the ride as well.


James McKinney: I love that. I love it. Do you think as we get to the end of our time, I want to honor your time, but do you think anybody can be an entrepreneur? Or is there a certain makeup?


Jason Y Lee: I do actually, I do think anyone can be an entrepreneur. I think some folks naturally have more kind of let me go at it, I don't care about falling down attitude which allows them to kind of deal with the bumps and bruises better at times. But I think innately that we are all creators actually. I think that's part of the DNA of all of us. It's mainly that I find mostly for folks who are hesitant or who think… You know the way I describe it is this way. Sometimes we have like what we think is a root in our heart that we've got to pluck out and throw out, but often that's like an idea or a business, or a vision that you have. It's really like an oak tree that's starting to take root. Some of those things can't be plucked out. You owe it to yourself to water it and to grow it. But the truth is I think that everyone has really fertile soil, and everyone has these kind of seeds that have been planted in their heart and in their life. I absolutely believe it. I think something that I'm really passionate about is giving people more opportunities to pursue their dreams because the truth is that it's not always equal. The playing field is not always equal as far as access to capital, access to opportunities. I feel like a lot of folks are marginalized in that way. But I do hope and I guess I want to speak kind of encouragement to folks that if you've got a dream I really do believe that anyone can be an entrepreneur.


James McKinney: I love that. I love it. One of the narratives that is common among entrepreneurship like you said is that it's Lone Ranger journey. There's this idea, because of how many, and I'm using air quotes here, "overnight successes" there have been that the media darlings love. It's all about sitting on a couch pounding code, just you by yourself eating Pop Tarts or whatever the case may be. So the reason I ask this question is to give my listeners an understanding that it's just not true. So when you look back to your entrepreneurial journey who are all the people you point to with such immense gratitude for their contribution?


Jason Y Lee: Yeah, it's funny because we started this podcast talking about my parents and how they were initially so dismayed by my decision, but I think that a lot of my courage comes from them. That I wouldn't be here in America, I wouldn't be given this opportunity had they not first taken a step to say hey I want to believe in a better future for my kids, and for myself. And a lot of my work ethic and a lot of those things came from them.

And then I think throughout my journey I saw so many folks who spoke I guess kindness and generosity in my life, and really pushed me. I've got mentors at Bain. I've got folks from college. I've got all these people that every time I asked for a hand honestly people would say yes. That is I think such an important skill as an entrepreneur is to be able to have the courage to ask for a hand. Not everyone will say yes, but I think the people who do will come through for you. So my initial investors, the first yes was actually a professor. She was a professor at Wharton at the time, but now a professor at Harvard Business School, Dr. Laura Huang. I asked her if I could audit her class on entrepreneurship because I had this inkling of I want to learn how to do it. And at the end of the class I said, "Hey would you be interested in angel investing in this new media company I'm going to start?" I don't know if she actually fully believed in the vision, and hopefully she did, but I think she saw within me the trait of just persistence. It's the thing I always look for when I try to look for other entrepreneurs is one is this grit of persistence that you can knock me down seven times, I'm going to get up eight. The other is actually a humility and understanding that we're not going to have all the answers but that we've got to be humble enough to dust yourself off, pick ourselves up, continue to learn and grow otherwise the company won't. Yeah, I'm just really fortunate to just have so many amazing people around me who have been part of this journey, and a lot of our success comes from them and form our team.


James McKinney: I love that. And I would love to give my listeners a chance to sit with you one on one, to answer all the questions that I didn't get to because of the sake of time. But it'd be an unreasonable ask because of just how many listeners there are at this point in the game. But one of the things that I do want to afford them is this virtual mentoring minute if you will, where it's just you and one of my listeners. Maybe it is the listener who constantly is challenged with cash flow issues and payroll. Maybe it's the entrepreneur who has an ecommerce business but can never seem to truly get traction, get off the ground. Or maybe there's a young person out there who is creating content media and just isn't getting the subscribers or the distribution. Maybe it's the wantrepreneur who has got a book full of dreams and ideas and still has a nine to five, and there's some level of fear as to why they won't go full tilt into their vision. Whatever the case may be, whoever it is that resonates with you, whatever one of those personas. Who is it that stands out for you and what would you like to say to that person?


Jason Y Lee: My favorite part of the entrepreneurship journey is towards the beginning where it is a white paper of ideas, and you're terrified because you don't know how to take that first step. I think when I listened at that stage to podcasts like this, and heard other amazing… you watch Steve Jobs or Bill Gates or Elon Musk or whoever it might be talking about their journey, it feels so inconceivable. What I would say is if when you're at this stage, which is I think I have an idea or I know I've got a couple of ideas, I just don't know what it is but I'm terrified to take that first step, what I always encourage people to do is just to fail several times. Meaning you've just got to get in the habit of trying. That's your first task. Your first task is not even to ask a question or find the right answer to the question. Your first task isn't to get that first investor. The first task is to build the muscle of trying to do this new thing, and what I would say is at first it may feel foreign and at first it'll feel honestly really shitty because you're doing what Renee Brown calls an FFT, a "fck first time. We feel so insecure because it's like wait, I'm not good at this. And of course you're not going to be good at it, but that's okay. But the more that you try the different things, the little steps, the better you'll get at it and the better you'll build that muscle of entrepreneurship.

That's just the encouragement I would give is I think about swimming a lot. I swam in high school. Imagine that you're swimming in the middle of the ocean and you don't know which way land is. You don't know which way the dream or the mission is. Rather than treading water and looking and looking and looking, sometimes it's actually more effective to swim one direction for a mile or even 10 miles, realize you've been swimming in the wrong direction, turn around, and swim completely the other direction. Sometimes it actually can be more effective and less energy draining than to be standing in the same spot treading water that entire time. At least this way you've learned that this was not the direction you're supposed to go.


James McKinney: Once you've had a few moments to process all the value that Jason Y Lee brought us in this week's episode, please hit me up on LinkedIn, Facebook, or Instagram and share with me your thoughts on this episode. And if you've been around The Startup Story for any length of time then you know how much emphasis I put on the idea that entrepreneurs support other entrepreneurs. For that reason, I hope every single one of you will visit jubileemedia.com and watch their content. In fact, when you visit jubileemedia.com, you will see "Watch" in their navigation. Smash that link and then subscribe to their YouTube channel. Also, aside from their weekly video creation they have their first documentary being featured at the Tribeca Film Festival. You can view it online. The documentary is called Accepted and it's an intriguing look at the high stakes quest for college admissions. We're going to include a link in our show notes for easy access, but please let's show up for Jason Y Lee for all the value he delivered and let's visit his website jubileemedia.com and let's hit up that link in the show notes to see the documentary at the Tribeca Film Festival. And now for my personal ask.

The Startup Story community has been so incredible about sharing our podcast with others, but we have more stories to tell and more people to reach. We too are a startup and word of mouth is everything, so please follow us on Facebook and Instagram @TheStartupStory or on Twitter @StartupStory_. If you're on LinkedIn, please search for The Startup Story and follow our company page. LinkedIn is a really powerful way to raise awareness of the show. But the most impactful way you can help us grow our audience is to leave a review on Apple Podcast. Or if you listen to the show via Spotify, then please simply share the podcast directly from your Spotify app or wherever you listen to the show.

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June 15 2021
Jason Y Lee, founder of Jubilee Media

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