Conversations with members of the Harvard and Radcliffe Class of 1992.
Hosted by Will Bachman.

Episode: 65

Reggie Williams, Entertainment Entrepreneur

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Show notes

Reggie Williams had a great experience in his four-year period at Harvard College. After graduating, he went to Harvard Law School, which was a much more difficult and a lesser social experience. He was disillusioned with the law, finding that it was influenced by politics and was more subjective than objective. He decided law was not a profession he wanted to pursue.


Moving into the Entertainment Industry

While in law school, Reggie was inspired by the notion that he could pursue entertainment and started asking people around campus for advice. His goal was to eventually become a senior executive at a multimedia entertainment company or run his own company. He did not achieve his best grades in law school, but he did pass and he wrote a thesis about Tupac Shakur and the music industry needing to regulate itself with a voluntary rating system.

Reggie took a negotiation class with Bruce Patton and Roger Friedman, which was the greatest course he took in any stage of academics.  He applied to 27 law firms in New York and LA, and only one firm accepted him. He had a great interview with a man who became his mentor. He was invited to New York City to work for Paul Hastings, an entertainment litigation practice, which represented stars like Madonna and CBS Records.

However, when he got there, they didn’t have a place for him in the entertainment litigation department. Reggie learned that sometimes life doesn’t give you what you expect, but it’s what you need. He found himself doing business law, which was more aligned with his interests in entertainment, learning contracts and IP. As a business law associate interested in entertainment, he was the first person to give deals in the entertainment industry, which helped him navigate the challenges and opportunities in the entertainment industry.


Starting a Digital Lifestyle Entertainment Industry

He realized he didn’t want to stay in corporate law for too long, and Reggie shares how he gained experience and made connections that helped him move forward in his career and land his dream job. He talks about having three dream jobs on the table but how negotiations fell apart and he lost all three. However, he finally landed one of them and found he was moving full speed ahead negotiating and closing deals with artists he loved. After two years, the partner came to him and asked him to write business plans for a couple of clients, which he did, and then decided that  the next one he wanted to write was for his own business. So, in 1999 he launched his first business and built a digital lifestyle entertainment experience, based around hip hop which was to become the next 25 years of his career. 


Founding Ambrosia for Heads 

After a rollercoaster ride of financial and relationship difficulties, Reggie was navigating the economic downturn in 2008, and his second wife was pregnant. In 2009, Williams realized that hip hop was growing and needed a platform that targeted people 25 and older. He created Ambrosia, a curated service for hip hop fans, and branded it Ambrosia for Heads (AFH), which would eventually become a streaming platform. He aimed to be a concierge through hip hop culture for people, starting as an editorial platform and building an audience around it. When Reggie founded AFH and was initially unsure of the role technology would play in the entertainment industry. However, he realized that technology is sovereign and that content is king. He had a dream of creating a hip hop lifestyle that encompassed TV, film, music, and other forms of entertainment. He set out to build a sustainable platform, similar to Netflix or Rolling Stone, but with a focus on adults.

As social media exploded, Reggie used Facebook to build a community focused around hip hop culture. He aimed to make it like a Rolling Stone, with roughly 75% of the content being about music, 60% entertainment lifestyle, 15% politics, and 10% dark corners of the world. 


Merging Technology and Entertainment 

In 2017, Williams launched a subscription video service like Netflix on several different platforms, with over 300 hours of programming. Despite a successful launch, AFH was unable to raise capital, although having built an audience of 15 million a month. He listens to 20,000 hours of music last year and has a son and three sons who all have the same favorite artist, Kendrick Lamar.

Reggie shares stories of meeting and working with artists, revealing that they are often very different from their appearance on stage or in public interviews. Most artists are incredibly smart, but this is not always welcomed in certain genres. They can be both introverted and magnetic on stage, but when they work with them, they start to get to know them as real humans.


Influential Professors and Courses at Harvard

Reggie mentioned being impressed with Derek Parfit, a philosopher who taught at Oxford but later came to Harvard. Parfit’s book, Reasons in Persons, explores personal identity and the concept of the Star Trek transfer transformer analogy, which suggests that everything is created in the next place. 

He took a course called Moral Reasoning in his freshman year taught by Harvey Mansfield. He also took feminism courses, which he found fascinating, and he also mentions film courses, which he had taken in his freshman year. 



03:12 Going to law school as an entertainment lawyer

09:07 A job offer from an entertainment law firm

15:51 The turning point in his life

18:31 The opportunity to work for Bbt

24:22 What has surprised Reggie about the industry

30:54 Taking a stand on social media

39:10 The unwritten rules of meeting celebrities

42:44 Reggie reflects on fatherhood







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92-65. Reggie Williams


Will Bachman, Reggie Williams


Will Bachman  00:01

Hello, and welcome to the 90 T report conversations with members of the Harvard and Radcliffe class of 1992. I’m your host will Bachman. And I’m excited to be here today with Reggie Williams. Reggie, welcome to the show.


Reggie Williams  00:15

Thanks. Well, it’s great to be here. This is a really, really awesome idea. I just learned about it maybe a few months ago, got this group chat with about 30 folks from 92 that were in every day, multiple times per day. And someone mentioned it and talked about what a great thing it is. So I’m honored to be part of


Will Bachman  00:33

that is awesome. And I love the idea that you have a group chat with classmates, and that those conversations still continue, I love that. Encourage your encourage your group chat mates to, to reach out, and we’ll have them on the show. So tell me about your journey since graduating from Harvard.


Reggie Williams  00:54

Yeah, that’s a really, really interesting question. You know, first I’ll start by saying that, you know, to date, I don’t think that I’ve ever had a better four year period in my life than my time at Harvard College. You know, they’ve definitely been great years, great occasions that happened. But in terms of a four year block, I don’t think anything tops, it was great people, as I mentioned, many of whom I’m still in touch with today. And so there was, it was going to be a hard thing to tap after that, you know, I actually went to Harvard Law School, right after, didn’t take any time off, thinking that I was going to be able to continue that time there. And it was a vastly different experience for me in a number of ways. First of all, it’s Law School, which is much, much harder, much less social, I found it to be it was very focused on learning a trade and being a bunch of studies and getting job done and kind of going back and doing your thing. And so the camaraderie that I found in a college just wasn’t there. And secondly, I was kind of disenchanted with the law, shall we say, from my first weekend, and so are disillusioned is probably a better work. And so it just was not nearly as rewarding of an experience. But


Will Bachman  02:11

wait a minute from the first week. Oh, my God, the first week that is brutal. What happened in that first week to you know, get you on that disillusionment, trajectory that is rough to keep going for? After that what happened?


Reggie Williams  02:28

You know, it was a it was a revelation. And I think we’ve seen it this year, in particular, I think, regardless of your politics, the notion that that courts adhere to, you know, the letter of the law, a precedent that is based on some sort of objective standard. I don’t know that many people believe I certainly don’t believe you know, for me, I saw it as much more influenced by politics, in some cases, a person’s moral compass and others, but I saw it as being much more subjective than objective. And so I left I was kind of do this illusion from the start there.


Will Bachman  03:06

Okay, well, but you sold your Don, it sounds like so. Okay, I interrupted, you keep going.


Reggie Williams  03:12

Yeah. So do and, you know, so I’m a person who, you know, think about this question. I’m a person who kind of always had a 10 year plan, you know, at least professionally. And my 10 year plan going into law school, you know, I was either going to be US Attorney, my judge and potentially politic politics route politician, or else go the entertainment route came from Evansville, Indiana. I never thought in a million years that the entertainment industry was something that I could be a part of. But at Harvard, I took some film courses, and I started to think, Hmm, you know, maybe. And so from week one at law school, I’ll say, you know, while I didn’t get I was disillusion in terms of the class, what I was kind of empowered by and galvanized by was the notion that I could do pursue entertainment. And I started asking folks around campus, you know, what I could do to get in and everyone’s directed me to this one person who actually was very kind, and gave me some great words of advice. And I started my path toward being an entertainment. I also knew that I probably didn’t want to be a lawyer long term. You know, my, my goal was eventually to either be a senior executive at a multimedia entertainment company, or run my own entertainment company. And fortunately, over the years, I’ve been been able to do both. But so I did law school, you know, gutted my way through it, I will say shamelessly helped my kids don’t hear this but you know, I made my worst grades in my first year, because I and I tried the hardest that year study, you know, dutifully went to every class, read every case, you know, etc. Third year, I believe I went to class one time But I learned the system and I won’t divulge the system, you know, so snot out other people who might be there and still using the same system. But suffice it to say that I got the best grades. For my third year even I’m putting the least effort, highlight though, was that I was able to write my, my thesis, and I didn’t write one in college because this was my first time writing a thesis. And it was about Tupac Shakur, and the music industry needing to regulate itself with a voluntary rating system. So that was a pretty cool eye opening experience and great way to kind of cap it off. I’ll say another positive to law school was that I took a negotiations class with Bruce Patton and Roger Friedman. And that was, by far the greatest course, I took in any stage of academics, because it was beyond just learning about how to negotiate in business, but also how to navigate live conversations. And to this day, I still use that. So, you know, again, I was focused, I really wanted to be an entertainment, so is either be in New York, or LA. And so I only applied to firms in those two cities. And I will, you know, say with without any shame that I’ve sent out, like 20, something 27, something like applications to different law firms, and only one decided to take a chance on me, I had a great interview with this guy, who was a mentor who became a mentor for a long time thereafter, both at the firm and after I left the firm. And he invited me and the firm Paul Hastings invited me to come to New York City. They had a great entertainment litigation practice at the time, which was phenomenal. And represented stars like Madonna, I think CBS Records and others. But unfortunately, when I got there, they didn’t have a place in the entertainment litigation department for me. And it was a huge blow for me at the time. But one of the first times that I learned that sometimes life doesn’t give you what you expect, but it’s actually what you need. And so I found myself doing business law, which was fantastic, because it was much more aligned with what I wanted to do learning contracts and IP. And that’s how the entertainment industry kind of rolls. And because I was the business law associate who was interested in entertainment, whenever the litigation department got a huge merger acquisition or something like that. And its contractual, it was spinning off to the business law department. And I was the first person that people thought of to give those deals and so got to work on deals with Interscope Records, and that Jimmy, I have been still one of the biggest executives today. Built Beats by Dre with Dr. Dre and just like an icon, so met him early in my career, walked by Suge Knight, I didn’t meet him, but he’s still like maybe the biggest person I’ve ever seen in my life. Even though I’ve seen Shaq and others, his presence was just so large, and a couple of other great entertainment transactions. And so that was awesome from our resume. But you know, kind of similar to my law school experience, I knew that I didn’t want to be in corporate law for too long. And I started applying for jobs probably six months in. And, you know, one of the great connections I made in law school was when I was on the committee on sports and entertainment law, a woman named Susan Jenko, who will shout out and continue to stay to call my entertainment Fairy Godmother because I had dinner with her one night, when she spoke at Harvard and as a bunch of us and asked if I could get her number of contacts when I got to New York, and asked if I could take her out to lunch sometime. So I did that. And I would take her out maybe every six months, but she would always pay. And then afterwards, she would get my resume and start suing people. So she helped me get job offers at a couple of different places. One was my dream job heiress to records. Two was an entertainment law firm. And so this is I think, worth telling, you know, I was going to leave two years in, and I had two job offers, but the entertainment law firm, the guy told me, he said, Hey, listen, do you have any other areas out there? And that’s yeah, interview with Eric. Okay, well, which one day would you choose? And, you know, I’m sitting in an interview with a guy and desperate to get entertainment. So I’m not going to say I won’t take the job. Give it to me. So I said, Well, this is the job that I would choose. Okay, well, I’m gonna tell you right now, if I give you this job offer an heiress to hears about it, the person who finds the department is going to give you an offer. And I said, okay, and I’ve been on hold for two months with errors that didn’t think it was going to happen. And so, he gave me the job offer accepted the offer, I let my friend who was working at Arizona says no, that I got a job offer. And sure enough, I got a call from Arizona the next day saying, hey, we want to give you an offer. And at that point, it’s my dream job. And I have to really think and you know, I’m a person who really tries to be loyal to my word, I really didn’t want to backtrack. But I called up the entertainment partners. Hey, listen, I got this offer. You were right, they did this. I do kind of want to think about it. And he got pretty, he was pretty upset. And you know, I got a call a few hours later from Eris is saying, Hey, listen, we didn’t realize that you had, like, you know, gotten this offer or accepted the offer. And so we’re going to rescind our offer. And this is after I’d already told my current job that I was leaving. So now I don’t have the arysta offer. I don’t have my current job anymore, because I’ve tendered my resignation. And you can guess what the entertainment lawyer said, Well, you know, you told me you’re going to take the shop, and then kind of remake so I don’t think that we can do it. So I went from having three jobs to zero jobs.


Will Bachman  11:13

Wow. Okay.


Reggie Williams  11:15

As you can imagine, it was pretty stressful.


Will Bachman  11:18

Must be freaking out. Okay. So what happened, I was really freaking


Reggie Williams  11:21

out. And so you know, but the entertainment, I went back had enhanced the entertainment law partner, you know, just very transparent. That was my dream job. Force, fortunately, decided to give me the offer again. So you know, now my entertainment career starting kind of two years in. While I was there, though, I learned pretty quickly that again, like I said, I didn’t want to be avoided long term. And I had some really awesome work, you know, walked in the door. The first thing they did was give me a file of folders, deals that needed to get on the phone and close as they said, negotiate and close. And some were like DJ Premier, and rock him, all these names of artists that I loved. You know, I was suddenly working on projects for them. But about two years in, I started, the the partner came to me and said, Hey, listen. We think we have some clients who have some businesses that they want to start, and I think it’d be great to write business plans. I said, awesome. This is great. So I did that for a couple of them. And you know, actually, I did three. And eventually, I said, You know what, this is awesome. But the next business plan I want to write is for myself. And so I wrote a business plan for myself. And I was preparing to leave the firm in November, but partner kind of beat me to the punch. And then August, he came to me and said, Hey, listen, it seems like your heart’s not really in this. I said, Yeah, I’m not gonna lie said, you know, okay, cool. Well, why don’t we think about transitioning you out, and I’m gonna kick you out the door right now. But when you’re ready to go, you know, let’s figure out a game plan. So cool, I really appreciate that. And suddenly, I found myself starting my first business in 1999. And it was at a time where you could sit across the desk from a table from someone, and if you put, at the end of your business, you could credibly ask for a million dollars. And so I built a digital lifestyle entertainment experience, based around hip hop, which will become a recurring theme in my life. And it was great. A great opportunity for me, I transitioned myself from a business lawyer to a business person out of music into digital, and really kind of set myself up for the next 25 years of my career in an amazing way. The business didn’t work out in a traditional way. But you know, like I said, about my, my experience at Paul Hastings, I got what I needed from it, you know, and so, we didn’t sell or have a major exit, but I took myself my team as a unit to another company. And we all ended up making more money than we’ve ever made in our careers. And so I consider that to be a success when coupled with it. And it’s education that I got, and more importantly, the courage to do something like that, when I was young, without kids and you know, mortgage and all that other stuff, because it allowed me to know that my worst case scenario was that I could always get a job that paid me more than what I was making in my last shot. And so that’s when things got interesting, because it did have a kid, but I’ll move on on the professional side first, and then, you know, talk about personal side. So, you know, long story short, I I went to another company, and with my team, it was 2001. Now and you know, we all know 2001 was not a great year for a number of reasons. This is before 911 But you know, the economy was in turmoil because the digital boom that had happened to turned out to be a bubble. And so company I went to they, they started doing layoffs, unfortunately made friends with the CFO. And it’s always great to make friends with the CFO, when you’re at a company. And he told me, Listen, there’s another round coming, but you’re safe. And I say, great. I was having troubles in my marriage at the time. And that night, I went home and told my wife that I thought it was best to be separate. And I got a call shortly after I had that conversation from the CFO saying, Hey, listen, we made a list, and you were the last person on the list. But I wanted to give you a heads up that you’re going to be let go tomorrow. So now I am, I’ve told my wife that I think we should separate. And I don’t have a job. And I’m literally homeless, with a nine, nine month old, because I have to move out. Another really stressful time in life. You know, I had a great friend who said, hey, you know, come get my keys, you can stay at my place for the weekend, I’m going to be in Miami. And you could stay as long after that as you want when I get back, so you know, at a place. And, you know, three weeks later, I found myself sitting in the office, the General Counsel of MTV, interviewing for a job there. And then whose last hurdle before getting a job. I tried to get into MTV several times before that. And I was literally on the verge of tears in front of him because I wanted and needed the job so badly because I had no money and potentially, I held it together. He I don’t think he noticed I told him that story long after because we became good friends. And I ended up getting a job. And I spent seven years there doing some really amazing things. I’ll speed this up, I you know, I ended up going back to Viacom at BU T for six more years. But before I did that I had been in a startup. And when I was there, another kind of inflection point that my first wife and I did actually end up getting divorced. We had two great kids. And I was engaged to be married to my second wife. And we’d tried started trying to have a child of our own. And she got laid off. And so we stopped that or so we thought. Now she’s laid off. I’m at a startup, I’ve taken a 50% pay cut. But you know, I protected myself by you know, investing in having a nest egg, but it’s 2008. And people recall, 2008 was not a great year for the stock market. So like overnight, that nest egg was cut in half. And so now I have half the money that I was getting before half my nest egg. And I get a call from my wife saying, Hey, I’m pregnant. surprise to us both. And then, but then also know my company is not going in a great direction. So she’s laid off. We don’t have a big nest egg. My company’s likely going out of business relatively soon. And we have a baby on the way, another one of those really kind of stressful inflection points. But you know, about two months later, or actually, you know, maybe six weeks later, she got a job at a great record company. And I got a call from a friend from MTV saying, Hey, listen, we’ve got this. We’ve got there’s, I don’t know where you are in your job right now. But there’s an opportunity to go and work for BT, and help them rethink what music means to them, you know, and it was such a core part of their brand in a world where music videos are watched online. So I was able to go there. But I’d started another company and hip hop company lifestyle company Digital, just before I left and continued doing that the entire time I was a BT that company was called ambrosia for heads. Because I did that I was in touch with hip hop music in a way that most people were not in the building. And so I was privy to people like Kendrick Lamar and Drake and Jay Cole and lots of artists who ended up becoming really big over time before anyway, be TF btw. And so I was able to kind of see how they performed on my platform first, and then was able to put a lot of those people that I mentioned logic and a bunch of other people on TV for the first time. And so BT was phenomenal, phenomenal experience, you know, there’s arguably no one who came to fame like from 2001 on that I didn’t meet in that time period and I mean the biggest from Oprah to Jay Z to Beyonce to Will Smith to Puff Daddy to whoever you can think of it Music and oftentimes and film, narrow, Eminem, stuff like that I got to either meet and or work with him. So it was fantastic. But I ended up leaving after six years because my company was growing at a pretty nice clip and I knew that I wasn’t going to be able to really grow it to its full potential unless I jumped off and did it full time. 2015 I did that and grew the company to reach you know, a ton of people were at our peak were like 15 million people a month across the site socials and made it into one of the premier destinations. For people who are fans of hip hop who happen to be 25 years and older. So don’t oriented hip hop. And that has been a labor of love and blasphemy and the materialization of the dreams that I have for 20 something years. And it’s what I’m doing currently, you know, I’ve gone in and out of other companies since then, you know, it was a Conde Nast, leading digital video programming for them globally. For other brands, like Vogue, GQ, Vanity Fair, wired, when appetit and so forth for a couple of years. And man, oh, man, did I go through some hell there. But you know, and we could talk about that at some point if you’d like and then ended up at Netflix, which was a dream job, too. But AFH was always there and is now my full time gig. On the personal side, I’ll say that while I did always kind of have a plan for the professional, I never really had a vision for what my personal life would look like. And I think I knew vaguely that I’d want a couple of kids. But I never thought that I have three boys who are amazing, and probably indefinitely, the most important thing in my life have made some major sacrifices for them. You know, I grew up with my mom. She was a single mother. She and my dad split when I was six. I did see my dad like weekly, for like five hours a week. And we had a great relationship, but he just wasn’t a very prominent part of my life in my early years. And so for me, I wanted to pattern fatherhood after my mom who was supremely dedicated to me, there’s nothing that she wouldn’t do. And so, you know, I mentioned I was married a second time, I was actually divorced a second time too. Unfortunately, that’s not something that I ever foresaw. You know, if I thought about what my life would look like, personally, and I think the the naysayer of that came when my second wife got a job offer in LA that she ended up taking, and ended up splitting up my kids between New York and LA. One was already in college, but the other one was in high school and the other one was in grade school, and they were very close. And that tore me apart. It was literally a Sophie’s choice as to where I would live in racked me, you know, with extreme guilt and stress for several months. And it wasn’t until I had an epiphany about how I did envision my life that I actually was able to make peace with it. When I was younger. I always thought it would be awesome to be bicoastal live in both New York and LA since that’s where the entertainment hotspots were. And I ended up becoming bicoastal. I was in New York and LA part of every week. Both cities, you know spending at least every other weekend with each kid in the different cities. And nearly 50% of my time with each in both cities for like eight grueling months. bicoastal is not what it’s cracked up to be. But in 2020, which is around when this happens, the world stopped. And one of the benefits of that time is that, you know, it was very hard to say that a person had to work in any particular location for any job. And so I was able to get my son’s mom to come back to New York, the kids were reunited. And, you know, I ended up spending more time with my two sons who were still at home than I ever would have had things been normal quote, unquote, for those two years cooking meals and all that stuff. And so ended up being a tremendous gift for us. You know that the ex is we are amicable. I’ve had them both over for Christmas dinner last few years and cook for them and stuff like that. So definition of a modern family.


Will Bachman  24:27

Reggie, for someone who’s been in the entertainment industry, you certainly have a lot of cliffhangers and a lot of beats in your career. The all is lost moment several times. My goodness. What a career what an amazing what amazing path. So many, so many questions I want to ask. I mean one is you had this idea of being in the entertainment industry. Back in law school perhaps even earlier. What Do you understand about the entertainment industry now that you did not? Then what? What are things that have surprised you about how the entertainment industry works?


Reggie Williams  25:13

You know, it’s really interesting, because I did kind of foresee, I believed when I started the company in 1989, that, that the internet was going to be the primary pipeline of all forms of entertainment to all devices. And that is kind of materialized. You know, I’d say, What I didn’t anticipate was just how heavy a role Tech was going to play in that journey. You know, I think that now, you know, across categories, the companies that are dominating entertainment are actually tech companies. So you look at Netflix and the film entertainment space, we look at Spotify and Apple music and music space. And soon AI is going to know is going to change that even more so. So I didn’t, I didn’t expect the technology to drive the business as much as it has, you know, some of the restaurants said, the former and the founder of Viacom said that content is king. And I think that’s still true, but like, you know, technology is CO sovereign, I’d say and I think that’s been most surprising to me.


Will Bachman  26:29

Talk to me a bit about the company that you built, just tell us a little bit about the, you know, the kind of the product itself, and about what you’ve learned building the company.


Reggie Williams  26:40

Yeah, so, you know, I’ve had this dream since probably 1998, that hip hop lifestyle, you know, so all aspects of the culture, you know, conforming, TV, film, music, all of it was something that was big enough to sustain its own, like ecosystem in entertainment. So think about like a hip hop, focus, Netflix, or, you know, Rolling Stone, or, you know, every thing you can think of in terms of entertainment all in one. And so, I set out to try and build that in 99, it was ambitious, and I think, you know, something that was sustainable, but this is when we were only like 10% of the population hadn’t broadband penetration. And so take really 30 minutes to download a song, you know, so it’s a little bit ahead of his time, then, when I, when I started again, in 2009, I realized that hip hop at grow, to be something much bigger than could be captured authentically by one voice. And so I kind of took notes from what MTV did as it got older, you know, and so interview what always wanted to stay and be the youthful brand. And so that created pH one, speak more to adults. And I saw an opportunity to do something like that for hip hop, because there wasn’t anything that was specifically targeting people 25 and older. But you know, as I’ve reached that milestone, age wise, I realized that, that we still had interest, you know, folks our age in music and staying current. But none of us had the time that we did to, you know, fight through all the bad stuff, all the junk to get to the good stuff. The Ambrosia, ambrosia being Greek for food of the gods, I thought there needed to be, you know, something that curated just the ambrosia for hip hop hands ambrosia for heads, I literally had that conversation verbatim with a friend and co worker. And I said, Ambrose you for has a bet that name isn’t taken, you know, kind of jokingly, and sure enough, it wasn’t. The name had meaning. But, you know, I also learned from MTV that you brands, the call letters, because I was thought of AFH approach for heads as a ultimately going to be a streaming platform. And so I branded it AFH, as much as I did ambrosia for heads, knowing that at some point, it would be, you know, a TV platform. And so I set about doing that, for people 25 and older to be a service for them. You know, when we were in college, you had that person when you went to the record store. And that’s one of the great experiences for me, I had, I had people that I made friends with a tower and he you know, all the record stores in the square. And because of that not only did they know what I liked, and would direct me to stuff whenever release, they happen, but they also gave me the store discount, which was pretty awesome too. So I want it to be that kind of service, that kind of concierge through hip hop culture for people. So the plan was to start it as editorial and build an audience around that because it’s the cheapest way to do so. And social media is now Learn to explode. And so Facebook was a great friend until I became a foe for a while, and I use that to build a real audience and community focused around it. For me, hip hop culture touches on everything, you know, it informs news, politics, world events, and so I aspire to make it like a Rolling Stone. And if you read Rolling Stone, I’d say maybe 75% of it was about music, maybe 60% 10 to 15% was entertainment lifestyle, and other 15% was politics. And then another 10%, whatever the remaining percentages was devoted to some sort of, like, dark corner of the world that you’d never like, you know, knew about, like hackers or like, you know, some sort of like, kind of underworld type thing. And so, I really kind of patented it. After that. We had, obviously covered music and videos and interviews and things like that. But also, you know, really tried to put the medicine and the food. And so there’s a there’s like, a few years where I mandated the team that we do something on climate change every week, just to keep it kind of fresh in people’s minds. We were the first to my knife, and we were one of the strongest outlets when gay marriage was passed, we said, and we ran this headline on Facebook, which was like potential suicide. We said, Now that gay marriage is legal, when will Hip Hop stop being so homophobic? You know, we we covered like the the controversy around bathrooms in North Carolina and things like that we really tried to take a stand and present hip hop in a more elevated way and more intelligent way, in order to showcase like, just how powerful is culture that’s now coming up on his 50 year anniversary was. But again, the goal for me was always to get to a place where it became a TV service. You know, my email address was always wretched, AFH, you know. And so in 2017, I launched a subscription video service like Netflix on seven different platforms, with like, over 300 hours of programming, fought long and hard to get that up. And it was like, probably still my most amazing professional accomplishment. And then I went out to raise capital, and wasn’t able to raise capital. And that was, I think, one of the most Crushing Blows up experience professionally. Yeah. I believe that I have the pedigree, the education, entertainment experience, and proof of concept having built the audience up to 15 million a month, yet, we’re still not able to raise money. And that was a real head scratcher for me, and made me feel like I might be facing forces that were greater than a meritocracy. You know, there’s lots of stats out there for, you know, the success rate of blacks and raising venture capital. And it made me kind of question that a little bit, you know, and so also, when I was going through the breakup of my second marriage, and I was watching my business, not performed, the way I needed to, I didn’t have any money at the time, I was losing my family, I was being split between New York and LA. And it was a really, really, really rough, like, couple years, but, you know, came out of it. And, you know, like I said, like, taking those risks, has always paid off and kept making more money than before, and so forth, and still have the company going. And now we’re pivoting and starting to create content for other platforms. You know, we’re doing podcasts and documentaries and things like that. And so, you know, still going strong.


Will Bachman  33:55

Talk to me a bit about your own listening or attendance, to, you know, hip hop concerts, music, I can imagine, some people they get into a field because they love it. And then the business stinks so much of their time, they don’t actually get to, you know, maybe enjoy the actual thing that the business is about, do you? Like how often do you have a chance to actually go see music live? Or are you often like discovering and listening to new music? yourself? Tell me a bit about that a bit.


Reggie Williams  34:29

It’s funny enough, I’m going to see Drake tonight with one of my college roommates. Classmates, Don Cornwell. You know, I see live music at least a couple times a month. You know, I’ve had you know, in summertime, it’s probably once a week. Woman I’ve been dating for the last three years in the music business too. And, you know, hugely passionate about seeing my shows. And so, you know, we saw Erykah Badu Third World Center last week, we’ve seen a bunch of shows and that has been great as To listen to a ton of music, you know, I think, I think I think I listen to something like 20,000 hours, 25,000 hours with music last year. And in a really major pride point, my sons and I are three sons and myself all have the same favorite artist, which was Kendrick Lamar, which is great, you know, so I’ve never lost the joy, you know, in the business. And if anything’s only augmented it because I’ve had access to music earlier than it’s been released and been able to be in the studio, at times with some stars while they’re making music, like so seeing it being created in real time is like, incredible. And so, you know, but my passion is not just been for music, it’s been for film and TV too. And, you know, a probably watch a couple hours of TV a day, one of them was while doing cardio. And, you know, so yeah, I’m just a pop media junkie. And I have been really since I was a kid. And so the ability to make money and have a career and something that I love so much, it’s been a true gift.


Will Bachman  36:08

Now, you said earlier how you’ve met a lot of these artists in person, in some cases worked with them. Tell us any stories about what it’s been like to get to know the person behind the, you know, the, the name brand on the stage, and, you know, any, any experiences you’ve had there of you getting to know them as real humans.


Reggie Williams  36:33

Yeah, you know, the fascinating thing about artists is, they’re often very different than they present on stage or even in public interviews. You know, a lot of them, I’d say most of them are incredibly, incredibly smart, way smarter than then, like, like, almost genius level smart. And, and unfortunately, especially in certain genres, that that’s not welcomed. And so they kind of dumb that down a little bit, you know, and so you’d be surprised at how certain people carry themselves what they talk about how they speak. They also a lot of them tend to be very introverted. You know, they’re so magnetic on stage, but, you know, they’re you, you put them in a room, and they’re, they’re very quiet, you know. And so, it’s, but at the end of the day, I think that the biggest takeaway you learn from working with so many people is that they are just that they’re people. You know, I think we tend to deify artists and celebrities, and they’re human beings just like us. And the more comfortable you become with that, and after a while, you do become comfortable in rooms with famous people. And then they can kind of sense it themselves. And they’re more comfortable with you, you know, when when fans approach them, they know it’s a fan. The guard is up, they they’re expecting the photo request, and you know, got to kind of like put on the face and stuff like that. But when they work with you, you start to really get to know like who they are as people. There’s a two year period in life where I was around Kendrick Lamar, probably every two weeks for two years, you know, worked extremely closely with him and his record label, Top Dawg Entertainment. And, you know, Don Glover and I tell the story of our 25th reunion. So when we were cabin here, but I accidentally crashed the party ushers house, thinking I was going to Jamie Foxx party literally just walked in and was hanging out in his backyard at the pool with like six or seven other people wondering where the party was, before I realized it was Asher’s house. So yeah, that’s some pretty insane experiences, you know, that Oprah and you know, I’m told, you know, listen, I don’t shake hands. I’m a hugger. And got like, one of the best hugs I’ve ever gotten from Oprah, you know, and similar experience with Michelle Obama, like I’ve been able to meet like, just countless countless people who’ve had true impact and sort of surreal, you know, you kind of detach yourself, you know, you find yourself just thinking about them as the person in front of you having a conversation like you and I and although this is more of a monologue, you know, but a dialogue, and you have to like, go back and think, Wait a minute, this is this person has done this, this and this, and this, you know, I think I try not to do that because I’m getting nervous otherwise.


Will Bachman  39:51

So you’ve hinted at it. And you gave a couple examples, but what would be some unwritten rule is when you’re interacting and actually working with celebrities. So it sounds like one of them would be, don’t ask for selfie. Number two, don’t ask for an autograph. What are some of the other things on the list? So you can be cool and not, you know, not come across as a fan and just a, you know, okay, we’re working together, we’re partners on this, where are colleagues? Right? What are some unwritten rules? Not to embarrass yourself?


Reggie Williams  40:25

Yeah, you know, you actually can’t get photos, you got to kind of judge the pacing of it, you know, and, you know, because we live in this world where photos are currency and social media is what it is, people understand it, so just can’t be thirsty about it. And it’s got to be at the right time. So you can’t do that. And I’ve got like, a ton of like, amazing photos of myself celebrities that it’s going to be completely obsolete in a couple of years when AI takes over and everything’s, like suspect, but for now, it’s still pretty cool. I’d say unwritten rules are and are not to disclose things, right? Like, you definitely don’t want to disclose, you know, Project dates, you know, collaborations like anything before, you get to go ahead there that it would be a huge, huge faux PA, you’re in a circle of trust. We don’t want to discuss, you know, private situations that you might be privy to, and Burton definitely been privy to some really crazy circumstances, you know, where people have friends die, and things like that, like, you know, in times where together like, you just don’t, you don’t discuss anything. So it’s really about I think discretion, discretion is really key. And that goes in terms of like, you know, your postings and like, but even like, you know, whispering to folks who just just don’t do it. So I think that’s, that’s the main thing.


Will Bachman  42:05

Talk to me a bit more about your boys. And it sounds like you’re a really devoted dad. And what are the things that have been most important for you, you’re hanging out with them?


Reggie Williams  42:21

Yeah, I’ve got three boys. One is 22, almost 23. One is 19. One is 13. It is fascinating. You know, I always leaned a little bit more nature than nurture. But like, after having three kids, like, I think I’m like 90% nature. Because, you know, kids that have the same DNA and you know, had very similar upbringings that are very, very different, you know, and, and their personalities seem to kind of be consistent with how they were when they came out of the womb. So that part is pretty incredible to see. That journey, you know, we you know, I had a great relationship with my mom, but it was a very parent child relationship, you know, you know, we didn’t discuss stuff about personal life and things like that. So I really wanted to position myself and kinda like, you know, this is the example I use like furious styles in a movie boys and other Laurence Fishburne character. He, to me represented, like the ideal model for what I wanted to be as a father and that he was he was definitely a parent, you know, he was strict and made sure that like, things were done properly, and like, you know, respect and things like that. But he also like, cut loose and will talk to his son about girls and, like, be a friend to him as well, you know, and so wanted, I was fired to be the kind of parent where my kids could and would talk to me about anything. And I think that that’s been that’s been really successful. Like to have my kids talk to me about everything, like my middle and just like, there’s no filter, sometimes I might do really bad thinking that my head but I don’t say it because I don’t want to reel it back what I’m really thinking, you know, and then the oldest, you know, we went to his summer camp, and like, you know, it comes running up to me and like, Dad, dad, I got my first kiss, and like, you know, just that kind of stuff in his very free about talking to me about, like, you know, everything in life. And my third my third one is much more buttoned up much more close to the vest. But that’s just his nature, you know, and like, I accept that from him to but to tell them specifically, you know, whatever you want to talk about stuff. I’m here you know, the stuff you can encounter and like, I want you to have a different perspective than the perspective you’re getting from other 13 year Roads, you know. And so, but yeah, it’s been a really magical thing. And some of my best times are us just, you know, we’ll go on boys trips every year and just, you know, shoot the breeze or, you know, sit in dinner and talk and you know, or play basketball, whatever we just hang, you know, the thing that makes those Christmas dinners with the moms bearable. And I mean, all the moms because there’s a lot of moms in the room with two wives and mother in law’s and mothers and all that stuff, is the four of us can just kind of sit hang. And you know, I was just speaking and so it’s pretty cool.


Will Bachman  45:41

I’d like to ask you turning the dial back to Harvard? Are there any courses or professors that you had at Harvard that continue to resonate with you?


Reggie Williams  45:53

Yeah, you know, so, wow, this is wild. So when I started writing for Ambrosian, for heads, my company, I took on a pseudonym, because I wanted to keep my company and BT very separate, I never wanted it to seem like I was leveraging BT for the benefit of my company. And also just, you know, from a competitive and prideful standpoint, I also wanted to believe that I built my company on its own merit. And so I wrote using a pseudonym, so that no one would know who I was, I also wanted to protect now BT from anything that might rise, it might be controversial, or whatever to, and that pseudonym was perfect. Which is, you know, the last name of Derek Parfit, who was a philosopher. He taught at Oxford, but then came to Harvard, and taught for a couple of years when I was there, and he wrote this book called reasons in persons, which is about personal identity, and what really makes us us and it just blew my mind now that one of the core hypotheticals that he introduces in the book is kind of like, the Star Trek transfer transformer analogy is like, you know, so what if you were, we made that teller, transportation, technology was real. And what happened was that you were destroyed in one place in an exact replica, like, there’s nothing missing. Whatever you believe, so mental, whatever is, is, is created in the next place. That’s just how the technology works. And so, you know, you kind of like go along with the premise. Okay, cool. Like, you know, that’s me. Okay, now, what if that happened, and there’s a malfunction on the original place, and the old you lives for a second or two, which one is you and, you know, keeps extending that out further and further, until it’s like, there’s two years which one is you. And so just that notion of what makes us us is like, you know, mind exploding. So when I was able to have him and be in classes, like, I was in the presence of a rock star, I was just in awe, you know, my jaw dropped when I first met him. And he was a real character, you know, unfortunately passed away a few years ago, but they were the same thing every day, he would have a pair of black pants, a white button down and a red tie. And he always had a two litre bottle of Fanta with water in it that he’s doing. And my friends who know me know that super hydrated is going to try and drink five liters a day. So he was well ahead of the curve on that. But just a really fascinating personality. I’d say that was probably by far my favorite course of college. My second was, was probably I took a course called moral reasoning in my first semester, freshman year, taught by Harvey Mansfield, and we read Machiavelli, the prince and Aristotle, and Nietzsche and all that, like, kind of classic philosophers. And that’s the thing that actually made me want to be a philosophy major, it just like had such a huge impression on me. I think beyond that, you know, a couple of things. So one, I took a few feminism courses, and I found that to be just like, incredibly fascinating, especially as it relates to, you know, how women have been treated over the years. And like, you know, women always get rights after men, even men of color did, you know, voting and, you know, still not equal pay and stuff like that. So that was just that was resonated very deeply with me. But the other thing was, I started taking film courses, as I mentioned, my junior year and had done that in the freshman year, but it was it wouldn’t have even crossed my mind. It could have completely changed the trajectory of my my career, because I probably would have wanted to go into film. And I’ve done that. And so yeah, I had a bunch of The Great Courses, but those are the ones that kind of stuck out to me.


Will Bachman  50:05

Amazing what an incredible journey you’ve had, and through the entertainment industry and building your own company about something you’re passionate about something I think so many people would aspire to do. Reg, it has been a great conversation, where can people find you and your company online sharing the links with us here?


Reggie Williams  50:27

Well, first of all, thank you again, thank you for those words. And thank you for having me. You can find me at reg R eg at a F h, like F. ambrosia for heads So reg are eg at AFH That is the email address. It will always reach me. We are ambrosia for heads that calm for the site and socials where ambrosia for heads with the number four instead of fo r. And yeah, so that’s that’s me.


Will Bachman  50:59

Amazing. Thank you so much for joining today. This is incredible discussion and really enjoyed hearing about your journey.


Reggie Williams  51:07

Thank you again. And yeah, I’m looking forward to hearing more of these. That’s a great, great product. So thank you