Entrepreneurial Appetite

Reimagining Reading with Leslie Winston III: Fostering Community and Connection with Monocle

January 22, 2024 Leslie Winston III Season 5 Episode 4
Entrepreneurial Appetite
Reimagining Reading with Leslie Winston III: Fostering Community and Connection with Monocle
Show Notes Transcript Chapter Markers

Have you ever wondered what it would be like to transform a solitary activity like reading into a vibrant, intellectual community experience? Leslie Winston III, the mind behind the Monocle, joins us to unravel just that. From his roots in a family that valued social consciousness and black history, Leslie's remarkable journey through architecture and technology has created a platform redefining how we engage with literature and each other.

This episode is a tapestry of ambition and innovation, weaving together Leslie's architectural precision with his drive to foster a knowledge-sharing society. We journey through Leslie's formative years, the influence of his HBCU-educated parents, and the pivotal switch from crafting buildings to coding apps. Leslie's story is a beacon for aspiring entrepreneurs, emphasizing the impact of HBCU networks and the resilience required to navigate the world of innovation.

As Leslie shares, the future of reading and human connection lies in platforms like Monocle, which encourage thoughtful discourse and counteract the polarization plaguing our digital interactions. Our conversation ventures into Monocle's potential to enrich the reading experience by integrating social elements, allowing readers to connect and share insights. Leslie leaves us with a powerful message on authenticity and the collective potential for positive change. Tune in for a narrative bound to inspire readers, thinkers, and creators to see the possibilities at the intersection of technology, community, and literature.

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Langston Clark :

What's up everybody. Once again, this is Langston Clark, the founder and organizer of entrepreneurial appetite, series of events dedicated to building community, promoting intellectualism and supporting black businesses. Today, we have a very special guest, leslie Winston III, co-founder and CEO of Monocle.

Langston Clark :

Monocle is a social and e-reading app that transforms the reading experience through real-time, shared perspectives. Like one of our previous guests, colleen Martin, leslie is the perfect person to interview for this podcast because his business overlaps with books and building community, and so I'm really interested to see how he tells us about the ordinance of Monocle, what it is, and in a lot of ways, it relates to us and our audiences. So I think our audience might be the perfect people to learn about this product and what it can do for us as readers. Also, I can't forget to mention that Leslie is a graduate of North Carolina Agricultural and Technical State University, my alma mater, Aggie Pride and y'all know I'm biased there, so it's a bad weather in a hotel, so I appreciate y'all looking at my regular clothes, but we're gonna make it happen anyway. And so, leslie, tell us about your heroes during it, like how did you become who you are and what led you into founding Monocle?

Leslie Winston III:

For sure, first and foremost, agripride, appreciate the opportunity, very excited to be here and grateful to be able to share my story with others. Like everyone else, it began with my parents my father Leslie Winston and my mom Betty Winston. They're both graduates of HBCUs, they both went to Virginia State University and my dad was in law enforcement. He's a park ranger. So if you've ever been to a national park, you've seen like those park rangers with the big hats.

Langston Clark :

Yeah, that's your dad.

Leslie Winston III:

Yeah, yeah, yeah. Yeah, they're like the cool cops. I didn't do the park watching for squirrels and deer and stuff, not doing anything for real. And my mom, she worked in government for her entire career Visit, public administrator, grant writer. She had an appointed position under a governor in Virginia. So that is something I bring up as well to highlight how I've always been shown the true happenings in local, city, state and federal government and how it impacts our lives. So I say that to say my parents obviously raised me to be socially conscious and aware of our responsibility in the world and how there are people who ultimately govern the lives we live and sort of set rules that we oftentimes don't consciously pick up on and impact who we are. So, yeah, from a fairly early, early age that was something that was made aware to me and of course, what coincides with that is the importance of education, so taking advantage of opportunities in school, both in the classroom and outside the classroom, to be able to put myself in a position to be one of those rural writers like my mom. So, yeah, I mean through school.

Leslie Winston III:

Growing up I went to a first school. It was like a private Catholic school. It was an all-black school in Richmond called All Saint's Catholic School. There were about 20 students in each class. All of our teachers were black. Actually, when I think about it, I might have had one white teacher, Really, yeah, yeah, so from a very early age there was a heavy emphasis on black history and I mean, I think at that age you don't really start to understand the impact that it will eventually have on you. Which just felt normal, which is nice, because I saw a lot of what we call now black excellence, but just black professionals who had gone to HBCUs, had done well in their career, were given back to the community and I saw a lot of black professionals in different spaces. That always made me feel like I could pursue what it was I found most interesting about the world.

Leslie Winston III:

Ended up after fourth grade went to public school, and that was an interesting transition because I really got to see how much our communities are actually influenced by the media around us. I think at the private school, the public school is all black public school as well, and as I got older I started to realize how interesting it was how it seemed like especially black men who were fitting into these tropes that we saw online. There's the rise of the internet and you have certain tropes that it seemed like people we wanted to fit into and I was very blessed to be able to have not only a family but exposure to. Unfortunately, there's a class divide and multiple classes within black America haven't been exposed to that black upper class, if you will, and knowing there are a lot of opportunities that are out there that many people don't have access to and that's due to a lot of social and institutional barriers that have been put in place. But so, as I went through middle school, high school again, always focused on trying to do well, getting good grades, still having fun, but ultimately I decided on being.

Leslie Winston III:

I like to make art, so I decided on being an architect. This is maybe ninth grade. I was like, OK, I'm going to try to be an architect.

Leslie Winston III:

I really like art. I used to love Legos and I really saw architecture as the physical manifestation of art. So, yeah, high school, I spent a lot of my time extracurricular time building up a portfolio of art, building out a resume of, going to summer camps related to architecture to position myself to be able to go to a top architecture school, and I ended up applying to the top architecture schools in the nation and then North Carolina A&T actually my aunt and uncle are good friends with the chancellor. I remember in high school I think 11th or 12th grade we're on a college tour down at In Greensboro and two engineering students give me a tour and my family a tour, so we're going around the campus, getting a chance to go to McNair Hall, go to Dine Hall, and I enjoyed my experience down there and that was actually the only HBCU I applied to, I think.

Leslie Winston III:

For reflecting on it, I didn't really want to go to an HBCU that bad because I had felt like again growing up, having gone to Black, private and public schools. Up through school, I unfortunately experienced a lack of excitement around education and higher learning from my peers, even in middle school, getting called I was a cool nerd, so I had a lot of sports, but I was also getting A's on my test and I like nerdy, quintessential nerdy things. So I think it was interesting because when I reflect on it, I can see how I had been programmed for lack of a better word to associate a Black space with something that wasn't a space in which you could find people who were really excited about higher learning or nerdy things or art or technology and going to A&T. I did experience that and this is during my visit in high school. But I would say that that visit, given it was just a day, wasn't something that ultimately changed At that moment, changed my perception. So I ended up getting a full ride to Syracuse University to study architecture, which at the time was, I think, number three architecture school in the nation. So I was really excited about that Ended up going there and I also had I got a full ride to go to A&T out of high school as well, the Dowdy Scholarship. So my parents, my mom, was like, boy, if you don't go to A&T, I'm going to die. She was hot, she was hot, she's still hot, she's still talking stuff to this day. But I'm really grateful because my parents always gave me the freedom to express myself and choose what I wanted to do, whether it was how I spent my time growing up, who I'm surrounding myself with. Obviously they guide me and give me advice and insight in their perspective of having more wisdom than me, but I never had controlling parents and I really appreciate that moment because, as you know, I ended up coming back to A&T, spent a year at Syracuse and realized I didn't want to be an architect. I started to.

Leslie Winston III:

Around that time, I started to formulate what my real mission was and purpose. I was getting older. I realized at that moment, as I'm in college, I was starting to build a tangible skill set to do something in the world. I started to think about, now that I have skills like what do I want to do in the world? What's my responsibility in the world? And I again thought about the issues that my parents talked about, the issues that I saw and in our community.

Leslie Winston III:

And while I didn't have one specific thing I was interested in solving, I knew that I just wanted to do something big and that had a widespread impact, and I saw architecture as an avenue for that. But I also realized that our world is digitized now and the things that have been impacting me the most and also allowed people to amass wealth to then enact change. I know that wealth allows you to have political impact because you can donate to politicians, you can donate to schools. That ultimately further, whatever philosophy you have about the world, it requires money. So I think in architecture school I was thinking about this isn't really something that would allow me to foster my entrepreneurial interests. And also, having a widespread impact requires now you building something digital. So after a year I was like well, maybe I'm in the wrong field, maybe I should study computer science, computer engineering. I had some ideas for some sneaker apps at this time, which, again, were just hobbies and interests of mine.

Langston Clark :

That's that cool learn.

Leslie Winston III:

Yeah, I was designing out an app With some of the design skills I picked up in architecture school. I remember designing out this app and I didn't know how to build it.

Leslie Winston III:

But I had the front end or UI of it and I went to the. At that time I was like, ok, well, I want to stay at Syracuse. I had a girlfriend group already there's 12,000 students there but the black community was kind of close to it. So I had my friends. So I was like I'm going to just stay here, I'm going to figure out how to pay for it, blah blah.

Leslie Winston III:

The architecture school was like can't switch your major because we gave you this money. So if you want to switch your major, you can't keep your money. Talk to the advisor in the Honors College and she's like well, look into this, go talk to this so-and-so in engineering. So I'm going all around campus trying to talk to people, trying to hustle, just to tell my story and have my voice heard. And then that experience ultimately what happened is money didn't come and I really felt like a number at the end of the day, even though I'd been given a lot of money to go there.

Leslie Winston III:

I had big ideas and things I wanted to execute on, or at least a vision that I wanted to try to fulfill. So, yeah, it was real frustrating. And then I thought about my other options, which were to transfer somewhere else to go study that was more affordable and a place that was right for me. And ANT was the first school that I really thought about. I thought about the students that I met that study engineering there. They talked about how easily they got internships at top companies. So I ended up transferring and it was interesting because I think after a year at Syracuse and having built a strong friend group there and seeing that there is, if I enjoyed the space at Syracuse among the black community there, then I would.

Leslie Winston III:

I can only imagine how much more enjoyable it would be to be at an entire institution with the same sort of passion for, like higher learning technology, you know, social impact and just sort of like fulfillment through the skills that we each individually have. Yeah, that's when I decided to transfer to ANT and that really opened a lot of doors for me, not only professionally but just, I think, mentally as well. I ended up studying computer engineering there, but I built a lot of, you know, friendships with my co founders, who are two friends from undergrad who study computer science, and it allowed me to see the diversity of black Americans and the diaspora and how we're not a monolith at all. And you know it wasn't that I really thought that going into to ANT but I think it's something you can only understand if you go there and I think is as well I started to see like how everyone I wouldn't say everybody, but like a lot of people that I was interacting with had sort of like a collective motivation or vision towards something greater. So it felt energizing to be able to like bounce ideas off of people and connect with people who also believed in me or I believed in them and we could work together. So I ended up taking a lot of the skills that I learned in architecture school applying them to. You know, this new exposure to building software and designing apps, like with in different pitch competitions at ANT I think there was one business pitch competition and maybe my sophomore year where I like built out this sneaker app even more and pitched it and things like that kind of led to an internship here and internship there.

Leslie Winston III:

So I did an internship at like a consulting firm, I think my sophomore year, and then junior year at IBM and then senior year I got an internship at this design firm called IDEO and they're like a global design firm. They're kind of like if you're in the design space you would have heard of them and if you have heard of them you know that like they're like the equivalent might be McKinsey in the consulting space, like Google in the tech space, but I'm, to my knowledge, I don't know if anyone from an HBC was ever even worked at IDEO. It's a small company, yeah, and the thing that I found was that Thurger Marshall College fund. You know they support HBC use unwaveringly and they had these pitch competitions that were these three day pitch competitions that they still do. So they won junior year.

Leslie Winston III:

So junior year went there. You form a little team while you're there you have like 48 hours or maybe 72 hours to go from concept to like prototype in a deck that conveys your business in pitch, and someone from IDEO who was like a friend of a friend was there and they facilitated a part of the competition. And so they did that two years in a row. And I think after the second year they asked one of the program coordinators like, hey, you know, we really want to have one of these students become a fellow at IDEO, and they asked me to have which is like their research and development arm. Like is there anyone in mind that you all have in mind? And again, like two years had gone by, I've done this for two years.

Leslie Winston III:

I remember like staying up all night, both times like drinking red. I don't even drink red bull, I don't drink coffee, but I drank red bull and I was like I was genuinely excited about what I was trying to build. The first app was one that allows you to round up your payments. So anytime you pay for something you could like rounded up to the dollar and then the difference will be added to a fund that goes to pay off your student debt. And then the other app was a health care app called healthy, so it's like an integrated, like health care app to measure, like your blood pressure, blood sugar, etc. Both of them I was passionate about. I didn't end up pursuing either them, but I think that passion, combined with, like me, having the skills to execute, was noticed.

Leslie Winston III:

And then I got an opportunity to go and be a fellow IDEO collab and that really transformed my understanding of how to execute on an idea and bring it to life as like a viable, marketable product, and that's something that you would have seen on my website as like a digital product designer, but that's something that I that I was exposed to. Then. I didn't know what a digital product designer was. It's kind of a new field, but it's like the idea that we all have visions about products, businesses, apps, etc. But being able to take that vision, create prototypes and create a brand for it and put it out into the world in a way that is helpful digital experience is kind of like what I found there. Yeah, that that kind of led me to like different opportunities.

Leslie Winston III:

After I graduated, I worked at like a startup called breaker box up in Cambridge Massachusetts that came from IDEO, and then I worked as a digital product designer with tech stars, which is like a global startup accelerator.

Leslie Winston III:

I think I have, I think, 30 or 40 programs, each program being in a different city, but I worked at the one in Baltimore last year and then also did one in Ireland, so went out to Ireland a couple times for a program out there and that's kind of a little bit about like my background and story. But I think when I think about like why this path has been carved out, I think it's because I've always kind of followed that gut intuition of of what is right for the broader than I have in mind, like that mission that my parents helped to cultivate in me, which is how do I shift society towards a more equitable future? That was a question that I had to ask myself each one of these moments when I decided like, okay, I need to not be an architect, I need to do something else to make an impact. I don't know which one of these options is going to allow me to do this most successfully.

Leslie Winston III:

So I think a lot of it was God as well, you know, like just creating that thought in me and then me being able to have the confidence to go do that, and a lot of the times, sometimes it wasn't even the confidence, it was like this might be the only option, which, in that case, like when I first transferred to anti, you know, I missed my friends from Syracuse.

Leslie Winston III:

I was, like you know, felt like my I was kind of derailed, but ultimately, where I am now I would never I don't regret anything, and I'm very, very thankful that I went to a and t, that I had those experiences, that I went to Syracuse for years, well, but it definitely has seemed like a plan that's been laid out by some higher, higher being.

Langston Clark :

So it's interesting some things you brought up in your story. So, as I mentioned to you before we started recording, and as I mentioned and as I mentioned on the podcast several times, my background is not in technology, so my background in education and it's interesting. I didn't learn a lot about what happens in, like, corporate and startup world until I met my wife, and my wife works for, like like you know, you talk about what's it called? Ido is called IDO, right, ideo, ideo, right. So they're like the Google of design, right. So my wife works for like the Google of health tech, and so she tells me these stories like yo.

Langston Clark :

So this person I worked with five years ago left and started this other company, or this person I worked with two or three years ago. They just they start up hot, right. And so I think oftentimes black folks don't get the memo on the benefit of going to like you don't just go work at Google because you want to work at Google To find your co founders. You learn what you need to learn in that rigorous it's like college part two, but you get paid a lot of money for it, right? So talk a little bit more about the benefit of you like working for IDEO, working for startup tech stars, and getting those experiences and how it led to you founding Monocle, or maybe enhancing your ability to be a leader, and what what Monocle is becoming and what is doing. But before you do that tells what Monocle is. Let's talk about that.

Leslie Winston III:

Yeah, I'm sure Monocle, as you kind of summed it up initially, is a collaborative reader. So ultimately it's a tool that merges the joy of reading with the power of social media so that while you're reading, without having to put down the book, so as soon as you're at, you can engage directly with other readers about the things that you're reading. So that's kind of like what it is. Now my vision for it and our vision for it is really to transform reading into something that we now see is fun, engaging in a in a community, collective type way. So if you think about just the simple experience of if you, if you're reading and you're you're wondering what is someone else thinking about this, what has someone else thought about this, you can not only find that within Monocle, but you can leave your perspective and that is the found, that can be the foundation of, you know, infinite amount of interactions and engagement that could exist throughout time within that book. So, yeah, that's kind of like what it is and what we hope for it to become. So go ahead yeah, no, to address the other part of your question as well. Yeah, the idea. It was a really interesting, eclectic place, so it's up in came. I was at their office in Cambridge Massachusetts, so the first opportunity I had there was a winter fellowship that was two weeks long, and then they invite me back for a summer fellowship, which was 10 weeks long, and then, first and foremost, they were working on a lot of like macro opportunities. So what I mean by that is like what are these broad trends that are shaping the lives of millions or billions of people? What are the technologies or tools that need to be created to ensure an equitable solution for these problems? So one big problem that I worked on that we're trying to address is, like the next billion users of the internet. So as internet connectivity expands across the world, as smartphone access increases globally because it's more cheap, a lot of people will now have access to this really powerful technology. But you don't even know how to read, let alone you have low numeracy or you we have a notion of like swiping up from the bottom takes you back to your homepage, or swiping down from the top, and then you have these other tools in your app. If you've never used smartphone before, those things and rules that a new user would never really be able to understand. So, like we were trying to identify what is an optimal interface for low literate populations, and it's kind of messed up when you think about the fact that, like the people who are working on it were not, we weren't in a low literate population, extremely high literate populations.

Leslie Winston III:

Cambridge Massachusetts, you know, mit is up the street, harvard's up the street. Boston is just like an intellectual city. But had a cousin who worked at Facebook and she was working on like a connectivity team, so helping Facebook provide internet to like. Her specific region was Sub-Saharan Africa and she connected me with this organization who helps companies do tests with you know, communities that they were serving. So we essentially. There was one guy on my team who was an engineer from Harvard. He was Kenyan, so he went to school in Kenya, grew up in Kenya and then went to Harvard for college. And then an artist who also went to Harvard. She was like an incredible visual artist. So we have three us three and then one do Jacob, and Jacob is like my mentor now, but he's like an incredible artist engineer.

Leslie Winston III:

The thing I noticed about all the people that work at IDO is they One don't give a fuck about what anyone else thinks. I think a lot of the times, just me. We as people get caught up in things that are not at all in alignment with the greater mission that we might say we're serving or want to serve. But the people I met there dedicate hours on hours, on weekends, nights, mornings just exploring the things that bring them joy and creating things like literally just whether it's physical toys and like trinkets or like art. A lot of them were like very much creators and had a skill set that spanned across like three or four disciplines. So, like Jacob, for instance, he could create things in like a woodshop so physical products. He studied as an artist, but then he could also code so he could build apps. But he was also an incredible like illustrator, so he could make illustrations that you would think came from like a professional artist who only does that full time.

Leslie Winston III:

But the type of people I met there were inspirational because it made you realize one like time is the most valuable asset. Every second that passes you could either be spending it honing your craft and things like. Every time you put something out in the world, you learn something new as well. You get thoughts from someone else and that opens a new door or causes you to have a new revelation of oh wow, I should go explore this, I should go try that. So something that they pride themselves on is like our prototypes, which prototypes are just like small manifestations of this solution that someone can kind of interact with. So in this case, for the next billion users, we created some prototypes for, like, what interfaces should look like for low literacy populations, based off of all this research that we synthesized from PhDs that had worked at Microsoft and Google and done research in the past, and we put these prototypes in front of some people who lived in like a remote village in Kenya.

Leslie Winston III:

And this was facilitated through the organization that I got connected with. But that is aside from the point. I think the main point here is that it allowed me to understand one that whenever I have an idea for something don't just sit on that idea, like, even if I'm putting out something that is not what I envision it to be in 10 years or one year or six months, putting out the smallest iteration of that or just putting it out into the world gets me that feedback or gets me that reaction from someone else that not only makes me more motivated to do it and creates sort of that momentum, but it also lets me know is this something worth pursuing or not? So when I have the idea for Monocle and this may be a good segue into that story this is like right after George Floyd passed or was murdered, you remember, like the collective social effort on understanding race in America, policing in America all of them people were wanting to share, like the things that they were reading and things they were listening to. So I picked up this book called History of the Black Dollar. I had received this book like a few years earlier at this conference, but the book was written by Angel Rich. She's a Hampton alum and like kind of finance guru.

Leslie Winston III:

So I picked up the book around this time maybe this is like a week after was reading maybe got about halfway through and I came across this passage about the black codes, which were like a set of laws for freed black people in DC. That reminded me a lot of like what is happening right now and specifically the black codes were, I think if you were out past a certain time by yourself, you had to have like your free paper freeing papers on you. If you didn't, you could be captured and the only way you could be freed and kind of envoyed being enslaved again was that you had to like pay 25 cents and you had to have one white man come to like the county jail or office and testify on your behalf and like I think that's a good thing and like essentially vouched that you were a you know, upstanding citizen and that you were free. And it just kind of reminded me of everything that's going on now. So I shared it, I took a picture of the book, I highlighted the passage and I put it on my Instagram and I was just like yo y'all check this out. This is so crazy. Just really reminded me about what's going on now and it kind of led to some discussion, maybe for about an hour. It has a few comments and, you know, I maybe chatted with some friends for an hour about it, but after that it was gone kind of forever into the ether.

Leslie Winston III:

But it made me think like dang, what if I could just leave this thought in the book permanently? And what else are for the other people who've read this book? What do they think about it? Yeah, I thought of this, about the idea of like well, it could be cool if, like, you have an e-reader and then that e-reader has, like, shareable notes and then those notes can be like, applied to or liked. So then you know again, as a product designer, as someone who's like, taken ideas and thought about what's the core of this experience, which to me was like the whole idea of leaving a shareable note. Let me go design this out.

Leslie Winston III:

So I literally took like three hours after having the idea.

Leslie Winston III:

I was like opening my laptop up, drew a couple sketches in my sketchbook and then went into Figma, which is like the design tool I used, and created a prototype and then I think I took it upstairs and showed it to my sister, who's like an avid reader.

Leslie Winston III:

I'm not a huge reader but, like my brother and my sister read a lot more than I do. So I showed it to them and they were like yo, this is crazy, like this is so dope. Showed it to my aunt, who's a journalist and she was like, oh wow, this would be so amazing, like for articles or reports and research papers. So that's when I knew I was like okay, like there's something here. It's more than just me seeing the opportunity. But me doing that was, I think, a direct result of not only having the skills and having developed the skills, but having that philosophy of like put it out in the world, do something and just put it out in front of people. And like that motivation I got from showing and seeing the light in other people's eyes that I saw when I had the idea was like, yeah, this is something that needs to be done.

Langston Clark :

How were you managing or how did you manage developing multiple skills? So you know you talked about. It's interesting. You talk about your friend who can draw and code and all that. It's like my sister, my sister with A&T. She was an engineer, but if I took a screenshot of us talking right now, my sister could draw it by pencil, but then she can also like code for whatever robots or whatever, like all that. Like I'm not gifted in that way, but talk about you and your gifts and how you honed your skills to be able to do these multiple things and how it shapes who you are as a founder.

Leslie Winston III:

Yeah, yeah, I appreciate that question. I would say it's been much less of like an intentional effort and more so like the intention has been I wanna create things or do things, and opportunities that I've had or ideas that I've had in the opportunity space I was in has allowed me to like, go and try to create that thing. So, like again, previously as an architect, I had to create designs for, like, large buildings that would actually fit within a site in the real world, so that gave me skills and software that I could use to design apps. But then, like coding, I had ideas for shoe, like trader, like a bot, you know which those are pretty common now. But like, if that taught me about, okay, how to create a program that can do that, can web scrape and do like some sort of backend processing or comparison between data points to identify opportunities, I think my response to that would really just be like I, whatever idea I had, I found people who knew how to do that thing and then went straight to them and I was like yo, how do I do this? And then, oh, you do it like this. Okay, sweet, I had no idea, but you gave me a start and I can use Google now. Things have gotten so much better with chat GPT. I use it every day multiple times. Any time I want to know how to do something, I go straight to it and that has been like a powerful tool for me recently.

Leslie Winston III:

But before I have more so especially in college, like I have developed a lot of relationships or friendships with people that have literally come from me, not knowing them and other people being like, oh, you should talk to someone, so like they are really good at you know this or that and I'll go up to them as a stranger. But hey, I heard your Angelica or heard your Lucini real people and you know they sat me down. They were years older than me but they sat me down. But hey, you should approach this problem like this go research those things. So I think you know, and when you're in college, you have that network there.

Leslie Winston III:

Now, if you're not in college, it's like you have the internet. But, like I've also brought people onto the team for Monocle that I found online that were like contributors to the e-reading space, like they were software engineers that like built stuff in the e-reading space, found them on Twitter and been like, hey, like this is what my friends and I are working on. I really think it's crazy what you've built. That's so cool, like we love to chat, and that actually resulted in one of the team members we have on the team like joining the team, so kind of like not being afraid to put yourself out there, have like those awkward social interactions at first before you get to know someone.

Langston Clark :

So I think it's also a good segue into you talking about cultivating your relationship with your co-founders, right, and you know, in the interviews I've done in the past and stories I've heard, they talk about not. It's important not to found what somebody who has the same skills as you do I don't know if that's your story but talk about the relationship, finding bonding and growing with your co-founders. Yeah so when I had the idea.

Leslie Winston III:

I knew that you know gonna want to have some more software engineers on the team, like although I studied computer engineering and code somewhat I don't really do it on a frequent basis now, so I knew that I needed, like some software engineers on the team I also had. Core to this idea was the notion that we could create something that could foster positivity, that could shift our collective attention, not only as Americans but especially black Americans, towards things of substance, those things of substance being books, and for me that was like a big motivator. So I knew that I needed to find co-founders that also believed in the underlying vision and saw the problem that we were looking to address, beyond the problem of like readers not being able to connect with each other easily, but saw the problem of, you know, miseducation, lack of education in our community, and with what's going on now books are being banned. Who sees sort of this collective effort by the government and by the elite to continue to brainwash our community, continue to disenfranchise us? And to me, like access to books and knowledge and having that book, those books and knowledge, be the foundation of like 21st century connection, meaning like instant human connection or social media, is really powerful. And that's one of the reasons why I was like, okay, this idea needs to exist because it's a potentially a political weapon and it's built and grown like as we wanted to. Like we could actually make a very powerful impact in the US globally.

Leslie Winston III:

But I felt that whoever I came to really needed to empathize with that as well, because I'm not in a position to pay anybody. We all have student loans, so I wasn't expecting anyone to quit their job and take this on to help build it. Now, I knew it was going to be like a long term effort, so I knew I had to like lean on my friendships, like people that I knew were good engineers, but also people that like trusted me, that value the same things that I value. So, yeah, I kind of like looked inward.

Leslie Winston III:

Well, again, one of my co-founders, uthman, who you're talking to soon, is my line brother, so I already knew like he would be on board. My other co-founders, austin he went to ANT as well as study computer science. I've been friends with him since like freshman year, but I already knew he's an incredible engineer. And my other friend, brandon Long, who if you went to ANT or even at HVCU sort of those years that he was there you would know him because he was like I think they had like the HVCU All Stars program, which was like I think five or six students selected that like went to the White House and represented HVCU as a collective and you know, he was traveling to like MIT for software engineering conferences and stuff like that, and people that are black engineers have gone to like PWIs. They're like how do you know, brandon?

Langston Clark :

I'm like how do you know? Oh, yeah, yeah, yeah.

Leslie Winston III:

So I think I kind of looked inward and found people that I thought were smarter than me and more driven than me as well, like people that I really looked up to and I think you know having heard how they have spoken about me, say like an interview for an accelerator in the past, like I think they saw that same mutual drive and had a mutual respect for me as well. So from there was kind of just like outlining a plan, this, how we're going to execute, and then, like since then I think we've given each other a lot of grace as well. Like it's been hard trying to build a company with student debt, with the price of rent, the price of living. So, to answer some of the other things you brought up earlier, like I have a full time job right now, which is something that started in September.

Leslie Winston III:

I was freelancing before for like a year. So you know I work on Monocle after work and on the weekends, and they also have full time jobs as well. But with the new funding from Black Ambition and hopefully a precede round soon, we're going to, you know, quit focus full time on this. But it's been hard, but I think a lot of it just again been giving each other like grace to say like we're in it for the long haul and we know that like there's these natural ups and downs but there's an upward trajectory over time when we are consistent about putting in work week after week, even though some weeks are slower and some weeks are faster.

Langston Clark :

Let's talk about Black Ambition, right, because you know you talked about the money is hard student loans, all of that. What is Black Ambition and what was your journey to getting there? Like to getting on stage, getting to pitch. But then what's the anatomy of the pitch? Yeah, for sure.

Leslie Winston III:

Well, for those who don't know, black Ambition is a nonprofit that Pharrell started, I think, three years ago, to empower Black entrepreneurs, not only from like, a business development perspective and access to human capital, but also access to financial capital, and he started it and created an entire team. So, felicia, I believe it's Felicia Brown I'm sorry for blanking on her last name. You want Google?

Langston Clark :

it, I do want to Google, I do Google it and I'll edit and I'll just fix it. Okay, okay, okay, felicia Hatcher.

Leslie Winston III:

Felicia Hatcher is the CEO of Black Ambition, so it's a medium, small, medium-sized organization now, but they release an application sort of in the spring and this year they, I think, received like two to 3,000 applicants, so submit initial application from there and then from the next little down to semifinalists I believe this year was about 200 semifinalists and then from 200 semifinalists you go through a three-month accelerator program. So you're broken into pods with companies that are relatively similar to yours, whether in company stage or company industry, and you have a mentor. So in these pod sessions you're sharing learnings that you all may have developed over time. You're sharing updates about your company, your setting goals and hopefully keep each other accountable, but you're also being evaluated during this period and then from there you're selected as a finalist if you make it that far, and all finalists receive some funding. But among the finalists they had eight top finalists and those eight top finalists got the opportunity to pitch for the grand prizes at demo day.

Leslie Winston III:

So this was actually my third time applying for Black Ambition. The first time I applied didn't make it as a semifinalist. Second time also didn't make it as a semifinalist this year and, Mind you, Pharrell is one of my all-time favorite artists.

Leslie Winston III:

Like NERD his group is top five groups or artists for me. So when he launched the program, I was following him on Instagram. Like three years ago I applied ASAP. We were really early at the time, but I still kind of believe like the idea was strong enough but kind of got passed up at that moment. I think maybe they were looking for companies that were a little bit more developed. Last year when I applied again, this would have been 2022. I think we still hadn't put out the beta yet, so we still were probably still underdeveloped. This year when I applied again, I applied like at the last minute.

Leslie Winston III:

I've been kind of discouraged because I applied twice, didn't get in, also feeling like seeing some of the other companies. There are actually some of the companies that I worked with at Techstars and another accelerator I was in with Monocle had become were finalists in 2022. And I knew how much traction they had. I mean, one of them had like done over a million dollars in sales. The other person had raised like over a million dollars without having black ambition. So I knew kind of the caliber and level of some of the companies that were being selected and I felt a little discouraged just because, again, I'd applied twice.

Leslie Winston III:

But something was just telling. Like you know, just go ahead and submit an application. We've grown since the previous year, we have put out a beta, we have new learnings, so, yeah, we applied, made as a semi finalists. I was really excited about that. And then when I received notice that we made it as a finalist, I was like, oh my God, like we're actually going to get funding from them.

Leslie Winston III:

And then, like a couple of days later, got an email that said we were top finalists, which meant that we were pitching, and so there were two prizes for the competition. There was a grand, a general grand prize, which you had to select which prize you were applying for, and then there was an HBCU grant. I applied for the HBCU prize, you know, assuming that the applicant pool is going to be smaller, so thinking that like, okay, I will out, statistically will have a greater chance of success. But when I received that email about being a top finalists, it said that all eight top finalists will be pitching on stage at demo day in New York for the potential to win the grand prize of a million dollars Mine when I applied the grand prize for HBCU.

Leslie Winston III:

The HBCU prize was 200,000. So when I got that email I was like, okay, well, maybe they like bumped us up or like something must have happened and they thought that we should be in consideration for this million. So, like me and my co-founders are freaking out. We're like, bro, like we have a chance to go against seven other companies to potentially win a million dollars. You know I'm rehearsing leading up to it. I'm trying to get in the right mindset, meditating all that, fully locked in thinking that I'm, you know, about to win this mill. Go up on stage pitch, don't? I don't stutter, nothing at all flows perfectly. The judges asked three questions after I felt like I have very strong answers to the questions. So you know, I sit back down. I think I might have been second to go. I sit back down and my co-founders were like texting me. My parents and family were watching. You know like, oh my God, bro, like we know you won, like you were the best by far, like that was amazing. So I'm like, oh my God, yo, this is this is crazy, this is it.

Leslie Winston III:

So then they're announcing, you know, the winners at the end of the program. You know they start with all the finalists, because again, all the finalists, all 30 finalists, got some sort of funding. It started 25,000. So they started at 25 and then 50 and then 75. And then they're like all right, now we're going to start announcing the top eight. I'm like dang, we already got a hundred thousand locked in, so we're again freaking out. And then they announced, like the top places eight to four. We're still not in it. So again, like stakes are getting higher. And then they're like then they're like now we're going to announce the HBCU grand prize, which at this point they were this was the third place, but they were still four companies that hadn't been named, including myself. So I was like hold up, there's only three places left. But what's going on? And then they say the HBCU grand prize. So that's when it clicks like, oh well, I guess you know, I guess I won that.

Leslie Winston III:

But it was interesting because I think had I who's to say, but like I went in there with the mentality that I was going to win a million and I think that really made the big difference in terms of how I prepare for you know, like shoe for them.

Langston Clark :

Yeah, okay, okay, okay, okay. So Okay, that makes sense. Do you think, though, if the HBCU was third place, if you hadn't applied for that one, would you have gotten the middle because they had to put somebody in that one, or they would have chosen somebody else from the HBCU when it put you there? You see what I'm saying.

Leslie Winston III:

Yeah, no, I think if I had, if I applied for the general prize, I assume I would have still been able to pitch, like I still would have been in top finalists and who's to say where I would have placed, but like I think I would have placed like one behind the winner. The winner gave a great pitch as well and she had a very heart wrenching story. You all should go check her out. Expert IEP is the name of her business. It's expert individualized educational plan.

Langston Clark :

Yeah.

Leslie Winston III:

You know her daughter had severe autism and you know, as a parent of an autistic child, she realized like the breadth of professionals that are supposed to serve children on the spectrum in different ways, and so she realized like she had to kind of step up as a caretaker in all these different capacities. So then she went to school to like not only learn more about the brain, how autism works, but also to study data science, to come up with a technology that can come up with an individualized learning plan for any person who is on the spectrum. So yeah, she had a really compelling story and you know, I think there were a lot of similarities between like what she and I want to accomplish to hopefully we partner with each other in some capacity.

Leslie Winston III:

But yeah, I mean again, I was just grateful to be there and I got a little signed vinyl from Pharrell. This is one of the-.

Langston Clark :

Take the blur off. Take the blur off, all right.

Leslie Winston III:

So I got a little signed vinyl from Pharrell to how to bring the vinyl there, cause, like I said, it's one of my favorite artists. So it was just, all in all, a really amazing opportunity. So I think it also just inspired me too, cause, like Pharrell has so much success in so many other ways and I think, like you know, he's looking for how he can give back and create opportunity for others, and it definitely inspired me to one day be able to do the same and know that, like he's kind of compounding the impact he's already had by a lot like exponentially, especially if, you know, say, for instance, we turn out to be as successful as we wanted to be, that would have been he's our first large check. And to know that, like again, him and his success kind of directly allow for our success to happen, is something that I hope to like also, you know, do in the future. So it was crazy.

Langston Clark :

That's good. So one of the things I want to ask is what is the future of Monocle and how can we support it? You're sure?

Leslie Winston III:

Yeah, the future of Monocle to me looks like a replacement of social media. I think, in a lot of ways, we have started to realize and internalize how damaging social media is. I think it caused us to compare ourselves with others, and everyone knows like comparison is the thief of joy. It distracts us from things that are really happening in the world. It also causes polarization. It has an invested interest in using negativity to make you fearful, but also more interested in those things that are making you fearful.

Leslie Winston III:

And I think books and, more importantly, conversation, are important methods to understanding on a human level.

Leslie Winston III:

And my focus is really what is a new digital experience that still allows for us to be fulfilled in our desire for human connection, because that's something that isn't gonna change.

Leslie Winston III:

You know, we've grown up in the 21st century with internet, with the ability to connect with anyone in the world at any time, so we need to still satisfy that craving. But how can we do it in a way that isn't destructive for us personally and for us collectively? And I think that reading and books. Given the variety of content that exists in the world, the variety of perspectives, books represent that endless set of content that we already see online, but in this case it's something that people who wrote the books put time and effort into what they're saying and that ultimately causes us to take more time to be introspective and also considerate of those words and how we understand those words, both individually and as a collective. So I say, the future of Monocle is very much a new way of reading and a new way of connecting with the world and, hopefully, a tool that allows for there to be more like kindness and open-mindedness and happiness in the world.

Langston Clark :

Yeah, it's interesting you bring that up, because I think reading books takes patience and, as you know, as a country and even in formerly black community, we become polarized. So if you take the time to read, inherent in that it's patience, and then the patience to have dialogue through your app while you're reading a book is something that I think would be beneficial to community. So real quick, last two questions how can we support Monocle? And then, what books are you reading or have you read that have inspired your journey? For sure.

Leslie Winston III:

Yeah, how you can support our website is pretty simple. Read on monocle. com. Or you can find us on social media at readonmonocle, that's on like, tiktok, twitter, instagram. We're in the process of building out our public app, so we released a private beta in 2023. We've since closed the beta to work on a major update based on some of the feedback. So, again, right now we're just working to then put out a public beta that everyone can use and enjoy and in order for you to stay up to date on that again.

Leslie Winston III:

Just check us out online and you can sign up to be notified. Also, when it does come out for those listening, feel free to make a club with your friends, or we have a feature that allows you to. If you've left a note, you can share that note externally on existing social media apps. So I don't know if you use TikTok Langston.

Langston Clark :

My wife does. But I want to see you. I want to listen to background, I want to see you writing.

Leslie Winston III:

I want you to get on TikTok Even if you don't have the app. If she sends you a link to a TikTok, you can still watch the video without having the app. So similarly, if I leave a note in a book, you don't have monocle, I can still send you the link and you can open up that page and note. So similar effect. Like we just want it to be easy for people to share their perspectives and invite other people into this new way of reading and conversing, even if they've never used monocle or don't have it. So keep that in mind and be on the lookout for that and be excited to use it. The other question was about the books. Yeah, right now I'm reading this book called Homo Deus. It's kind of long. It does take a lot of patience because I think I'm on like page 350 out of like 800. But it's been talking about. It's a sequel on this book called Sapiens.

Leslie Winston III:

Sapiens is kind of like the history of Homo Sapiens, from us becoming like Homo erectus to Homo sapiens, and like how we've evolved to present day. And then Homo Deus is sort of our evolution from present day and forward, speculating on what the next 1000, 10,000, 100,000 years have in store for humanity if we make it that far, and sort of what makes humans. Why have humans become the strongest and most demanding living being on the planet, in the sense that we are able to exert our force on the environment in a way that affects other living beings much more than they have done to us? And I think, with the rise of AI now is something that's really interesting to me, because we're starting to play the role of God if we're creating things that have human capabilities and superhuman capabilities and are still impacting humans and the broader environment. And it kind of talks a lot about where our instances in the past, in which there's a reference for how a very small group of humans have come together to make powerful impacts in the world, and also like what are the natural motivators for humans in these ecosystems?

Leslie Winston III:

So it talks about the Sumerian Empire and the Egyptian Empire and how these God-like beings and pharaohs that were mythical entities but still outlined algorithms that dictated how people live. So higher glyphs were sort of instructions for how to carry out society, how to carry out government, how to build rivers and our canals, to transfer water and then build cities around these new areas. Those are the same sort of algorithms that Microsoft has outlined, in that Microsoft is not. It's a mythological entity that ultimately, is governing the way that we live and creating the rules and instructions for how life should be carried out by us, even though it's not one singular person. We have buildings that memorialize these entities and our reflection of things that we serve, but they don't actually exist, nor are they human.

Leslie Winston III:

But it's interesting because, you know, 5,000 years ago, we're still behaving the same as we were today, but the impact is far, much more global. So, as the impact and severity of our actions increase, given the rise of AI as an influence as to how these algorithms will impact the future, like what's gonna happen. So I think it's been something that I found interest in and as the CEO of Monocle, because I think that algorithms influence what you see on your timeline, which influence how you view the world, which influence how much anxiety you have as you move through the world or what you think about when you see someone. So, similarly, if Monocle is to be as successful as we wanted to, we have to think about what are the algorithms that are gonna govern how people interact, how people engage, the books and content that you'll see, and is it in alignment with what values we help to promote in the world?

Leslie Winston III:

So, yeah that's kind of been what I'm reading now, kind of philosophical but hopefully preparing me to make the right decisions if and when we're in position to make decisions that could impact, you know, millions of people and impactful books that I've read. Obviously, history of the Black Dollar was super impactful because it caused me to have the idea for Monocle. When you asked that question earlier I was thinking about it a lot because, like I mentioned, I'm not a huge reader. You know one book I really liked. This is a fiction book. It's called Friday Black.

Leslie Winston III:

It's a series of short stories written by let me look at the author, kwame Adegi Brynja it's like four names, but he's an African-American, but African ethnicity, I think, specifically West African African where wrote a series of short stories that kind of touch on the black experience in America and there's this one interesting short story about where he compares blackness to like this 10 point scale and every day you wake up as a black man and you're like getting dressed and you're talking on Zoom and you're intentionally making decisions that point to a particular number on the scale, knowing that other people are implicitly interpreting it on that scale as well and ask how they view you, how you view yourself, how you think, how you feel.

Leslie Winston III:

So I think that was a really interesting book that just continues to keep me introspective about, like, the things that I've been programmed to believe and think and how I interact with others, in a way that tries to remove societal pressures and programming so that I can connect with someone as themselves and not the facade that we wear every day, which is our skin, our face. I try to connect with the true energy of a person. So I think that was an interesting book. With other short stories, but that one in particular keeps me grounded in the fact that we are just orbs of energy with human skin on top of them.

Langston Clark :

So, yeah, All right, Leslie Winston III. Thank you for joining us, Aggie Pride, and look forward to seeing your success in the future.

Leslie Winston III:

I really appreciate it, langston. Again, thank you for the opportunity, thank you for any of those who are listening and, yeah, hopefully we can change the world, make it better. All right, peace.

Founding Monaco and Building Community
Path to Impact and Innovation
Transforming Reading With Monocle
Building Startup, Finding Shared Vision
Winning HBCU Grand Prize in Pitch Competition
Future Reading and Human Connection
Book Exploration and Personal Connections