Leslie Winston III of Monocle On The 5 Things You Need To Know To Create a Successful App, SaaS or Software Business

Test your idea(s) with prototypes — Prototypes are questions, not answers. When creating a prototype, I always ask myself “What do I want to know and how can I ask this visually?” This often leads me to create various options to explore a digital interaction with questions that serve to uncover the underlying motivations of users. Utilizing prototypes in this way can save money and time while resulting in more desirable experiences. Figma should be your best friend!!!

As a part of our series about the “5 Things You Need To Know To Create a Successful App or SaaS”, I had the pleasure of interviewing Leslie Winston III, Founder of Monocle.

Leslie Winston III is the co-founder and CEO of Monocle, a social e-reader. Leslie’s background includes a brief stint at Syracuse University’s School of Architecture, a B.S. in Computer Engineering from North Carolina A&T, and product design roles at IDEO, Techstars, and Deloitte. As a digital product designer and visionary thinker, Leslie seeks to create tools that shift society toward a more equitable and peaceful future.

Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Thank you for the opportunity to share my story! Like everyone else, my story begins with my parents. As a son of two public servants (a Park Ranger and a government policy writer), my upbringing consisted of many conversations and stories of how and why the inequities of our society continue to persist. This dynamic certainly shaped my worldview, but it wasn’t until high school and college that I was able to understand what role I could play in shaping the world around me.

Visual art, LEGOs, and electronics captured much of my attention during childhood, so when I was challenged by my family and teachers to envision careers to pursue, I set my mind on being an architect. I saw architecture as the physical manifestation of art. As I learned more about it, I heavily resonated with its philosophy: physical spaces dictate human interactions which influence social outcomes.

I’m very blessed to have a family that encouraged and supported this goal by sharing literature, enrolling me in architecture camps, and simply taking a mutual interest in the field. My high school career then became focused on crafting an art portfolio and a set of extracurricular experiences that would make me a competitive candidate for a top architecture school. I thought this career path had been solidified after receiving a full-tuition scholarship to study architecture at Syracuse University; however, after my freshman year I discovered a path that I thought to be even more impactful: designing apps.

I had been a teen during the emergence and proliferation of smartphones, and despite it being a nascent space, it had already started to shape how I interacted with the world, my community, and even myself. When I had an idea for an app during my freshman year at Syracuse, I used the design methods and technical skills I had been taught in architecture classes to design a prototype, furthering the idea that perhaps apps are the new buildings and product designers are the new architects. This revelation triggered a change in my field of study and university. 4 years later I walked across the stage at North Carolina A&T State University with a degree in computer engineering and multiple experiences that had allowed me to combine my passion for design with a deeper understanding of technology. More importantly, I had more clarity on how I could impact the world.

Fast forward a couple more years to 2020, and I came across an idea that I knew was the “one.” In the weeks following the murder of George Floyd, I was reading “History of the Black Dollar” by Angel Rich when I came across a passage about the Black Codes. These were discriminatory laws passed in Washington D.C. during the Reconstruction Era that were eerily reminiscent of what America is grappling with today. So, like seemingly all millennials during this time, I shared my thoughts about the passage on social media, only to engage in brief conversations before my followers moved on. But in this moment I had an idea: What if our thoughts could be shared directly IN the book, allowing them to be explored by any reader, anywhere, at any time?

Thus, Monocle was born! Years of designing apps enabled me to quickly mock up a prototype of the core experience, which I then shared with a few friends and family members who are avid readers. Based on their reaction, I knew I had come across the right idea, and based on the need for truly meaningful human connection, I knew the time was right.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

After crafting an initial prototype in the summer of 2020, I didn’t commit to pursuing the idea until the following Spring after being selected for NexCube’s HBCU Summer Accelerator program. The $10,000 in funding provided by NexCubed signaled that I had something worth giving my undivided attention, so I made the difficult decision of quitting my job at a start-up in Cambridge, MA to move back to Richmond, VA to live with my family.

Despite the unwavering support of my family, the decision to return home and focus on building Monocle led to difficult times financially, socially, and emotionally. Seeing friends less was an expected implication, but I hadn’t anticipated the feeling of separation that comes when your peers and community may not understand the continuous sacrifice that building a company requires. As I began to peel back the layers of the start-up onion, I became overwhelmed by the amount of tasks, roles, considerations, and functional areas that most companies can dedicate departments to. The $10,000 quickly reframed itself as a drop in the bucket, and I started to think that maybe I was in over my head.

Whenever I had doubts though, I reflected on the why and who. Monocle was created to solve a problem that I experienced, so as long as I was able to solve this problem for myself, I felt as though it would be a success. Any additional adoption and support was icing on the cake. Furthermore, having co-founders who believed in the idea and experienced the problem as well ensured that we always had someone else to lean on when motivation or drive was low.

So, how are things going today? How did your grit and resilience lead to your eventual success?

Today, things are going well! I like to think about our company’s journey as having a similar growth curve as an economy. When I reflect on a monthly basis, there have been periods of high motivation and growth, and there have been periods of low drive and stagnation, much like a country’s economy. Thinking about our company in this way has allowed our team to know that despite momentary lapses, we’re on a continuous upward trajectory as long as we refuse to quit.

These periods of slow growth were often a result of personal financial strain, in which I had to take on freelance work to keep the bills paid. Fortunately, I was able to do work with start-ups which turned out to be a win-win as it solves the financial problems while providing insight and meaningful relationships. I worked with companies that were a stage beyond where Monocle was, so I was able to see what worked and what to avoid.

It has been said that our mistakes are our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

One of the biggest hurdles any founder will experience is how to demonstrate “traction,” especially when you’re pre-product. The typical metric at this stage is the size of a waitlist, which we were in desperate need of growing. So of course, I decided to spend some of the $10,000 from NexCubed on Instagram ads. After spending $500, which was a fortune for Monocle at the time, we gained 27 sign-ups and 1 interview lead.

In hindsight, the money was worth it because it showed me what NOT to do. Monocle promises meaningful human connection, which seems inauthentic when communicated in a clearly defined advertisement. Since then, I’ve learned the impact of appealing to emotion and how important it is to do this genuinely.

What do you think makes your company stand out? Can you share a story?

Reading has been slowly undergoing a shift from physical to digital reading experiences, however, digital reading has been focused on portability and has yet to adopt the one thing we’ve become accustomed to the most in the 21st century: human connection. Many readers view reading as an isolating activity, and those who don’t, have to rely on analog tools or distracting technology to connect with others.

Monocle stands out because it transforms reading into an experience that appeals to our seemingly innate desire to connect with others. Because we have become so familiar with instant social interaction via social media, Monocle is typically a very intuitive idea for people to connect with and even share ideas.

Whenever I see someone reading a book, I politely engage them to learn more about how they like to read. Then tell them about Monocle, and 90% of the time people’s eyes light up in excitement and inspiration! These conversations have led to beta users, product ideas, and even friendships. What most surprised me was that I typically don’t even have to share visuals for readers to describe what Monocle does. Moments like these serve as powerful reminders that we’re building something that people have been waiting for.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

1. Identify which types of rest you need and take the right steps — While participating in Visible Hand’s accelerator program, I learned that there are seven types of rest: physical, mental, emotional, sensory, creative, social, and spiritual. Each of these types requires unique attention to recharge, so it’s important to identify which parts of ourselves have been strained and to tend to ourselves intentionally and appropriately. I recommend checking out this TED Talk on the topic!
2. Surround yourself with other founders — As I previously mentioned, one of the unexpected hardships of starting a company was sharing my experience with my peers in a way that they could relate to. This feeling of isolation was fixed as I developed relationships with other founders who are similar to me in company stage, background, and industry. Beyond the productive conversation and relatability, it allowed me to regain social connection without compromising on the business.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

In 2019 I had the opportunity to be a design fellow at IDEO CoLab, a global design consultancy responsible for the idea of “design thinking.” While there, I worked alongside extremely talented and driven designers who explored how to utilize emerging technologies to solve globally prevalent issues. Jacob Waites was one of the designers I worked alongside who is an expert visual, interaction, and experience designer. Simply watching the speed at which Jacob was able to understand a problem, conceptualize a solution, and translate it all into a visually appeal and usable product was mind-blowing. Jacob was someone I was inspired to become, and working alongside him motivated me to spend countless hours honing my skills. Since then, Jacob has become a friend and a mentor.

When I had the idea for Monocle, I thought about Jacob’s ability to rapidly execute and digitally manifest an idea into the world. Instead of taking days to refine the idea, create a name or logo, or even consider the business’s viability, I focused on the one “magic” moment for the digital prototype which led to the validation needed to pursue the idea. All of this was from what I had learned from working with Jacob.

Ok, thank you for all that. Now let’s shift to the main focus of this interview. Approximately how many users or subscribers does your app or software currently have? Can you share with our readers three of the main steps you’ve taken to build such a large community?

Monocle is currently in a private beta with 500 readers. We previously tested an invite-only beta but switched to a private beta after 2,000 readers signed up within 24 hours. Our primary goal at the moment is to fine-tune the reading experience and identify the most desirable paradigms for real-time social connection which we found to be more difficult as the amount of readers increased.

Our community building began with brute force: DMs. After discovering the Instagram and TikTok communities of readers, known as Bookstagram and BookTok respectively, I sent messages to readers in search of 15 minutes to share prototypes and learn about the reader’s experience. At one point I sent so many messages that our account was temporarily deactivated as we were flagged as spam. This approach was successful, however, as it helped us validate ideas and grow a following of a few hundred readers in advance of our beta launch.

When we decided to launch the beta, we did an invite-only program where readers simply had to share a TikTok video about Monocle and tag two friends who they wanted to read with. This video describes our one-and-a-half-year-long journey of building Monocle and expresses our excitement to share it with the reading community. To our surprise, within 48 hours our video had gained over 100k views. Since then, we’ve been able to deeply connect with “power users” in the reading community who we believe will enable organic adoption from readers and communities that they have already connected with and cultivated.

What is your monetization model? How do you monetize your community of users? Have you considered other monetization options? Why did you not use those?

Monocle generated revenue through a 7% commission on all book sales. Readers can search for and purchase books on our app, after which they can begin reading alone or with others. We are also developing a premium version of Monocle that provides unlimited notes, live audio chat, and more for $4 per month.

We have considered monetization strategies that either charge for use or restrict more of the social features; however, we believe that Monocle’s value shouldn’t be compromised by charging for the core experience. Our passion lies in fostering connections, sparking discussions, and weaving a tapestry of ideas, so it is imperative that this can be experienced by all, for free.

Based on your experience and success, what are the five most important things one should know in order to create a very successful app or a SaaS?

1. Test your idea(s) with prototypes — Prototypes are questions, not answers. When creating a prototype, I always ask myself “What do I want to know and how can I ask this visually?” This often leads me to create various options to explore a digital interaction with questions that serve to uncover the underlying motivations of users. Utilizing prototypes in this way can save money and time while resulting in more desirable experiences. Figma should be your best friend!!!
2. Talk to the subject-matter experts — Industries are complex, with various individuals responsible for ensuring the function of any given part of the system. While Google, ChatGPT, and online reports can be a great starting point for insights, talking to experts and asking pointed questions can lead to discoveries that have yet to be documented digitally. For example, I attended an authors and publishing convention at William & Mary to learn more about the inefficiencies of the publishing space, and what I left with was a new perspective on publishing. Long story short, authors are stuck between a rock and a hard place when it comes to their publishing options. Either they relinquish future royalties for instant cash, or they retain up to 70% and exclusively distribute on Amazon, which does not provide marketing and sales support anywhere near what an author expects of a publishing company. Through this, we created a vision for the publishing space that has ultimately impacted Monocle’s current road map.
3. Make yourself uncomfortable — Talking to users can be a challenging experience, especially considering social, cultural, and human differences. However, I have found that when people notice your discomfort, they often reply with sincerity, as it shows your human vulnerability. When I went to Spain last summer I came across a bookstore that I really wanted to share Monocle with. The only issue was that my Spanish is elementary at best. I swallowed my pride, went inside, and began to ask the manager about how they engage with their community of readers. To my relief, her English was better than my Spanish, but one of the first things she replied with was how glad she was that I came inside to share Monocle, despite my low Spanish proficiency. We have since stayed in contact and I plan to collaborate with them in the future, as our goal is to become a globally adopted platform.
4. Emotion over economics — Since Monocle’s inception, I’ve applied for over one hundred programs and have done dozens of pitches to directors, mentors, and investors. Each pitch is a new chance to refine our story or completely reframe how we communicate the opportunity at hand. I’ve found that the most successful pitches and most meaningful conversations have been a result of sharing the emotional connection that I have to Monocle. I’ve been told that this is because we can all connect to stories that trigger our emotional response, whereas narratives that focus on economic opportunity may only be compelling to people who understand that niche, and even then the basis of the connection is financial.
5. Do things that don’t scale — Scalability is often preached as a requirement for success, but it’s most applicable for companies that have an audience and traction to scale with. After reading The Cold Start Problem, I learned how companies like Airbnb, Tinder, Slack, and others acquired their first few customers, and it wasn’t through an algorithm approach that was repeatable for all of their audience. Instead, the founders went out into the world to make relationships with their target audience and spend hours doing things that don’t neatly fit under the job description of a corporate CEO. For us, sending thousands of DMs, driving to conventions to make connections with authors, and stopping strangers on the train while they’re reading have been the most effective strategies for learning about our target audiences. While this may not persist, it has allowed us to develop a following that we can now engage with in a systematized way

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I would start a movement to spur participation in our democratic process through collective engagement with our elected leaders. Every day, in each of our respective states and localities, our public representatives attend meetings, review proposals, and make decisions that have a tangible impact on our lives; however, most of society does not have the time or mental capacity to think about, let alone engage with these individuals to advocate for their interests. I imagine a future in which the aspects of life that we care most about can be quantified and communicated to our leaders with ease, allowing our voices to be collectively organized and heard. Ideally, this entire process would happen on a decentralized digital platform that also allows citizens to see and understand the behaviors of their representatives, creating a means of accountability.

How can our readers further follow your work online?

For any readers interested in Monocle, you can sign up at readonmonocle.com to be notified when the app is publicly available! You can also find us on all social media platforms at @readonmonocle.

This was very inspiring. Thank you so much for joining us!

Thank you again for the opportunity and we look forward to bringing the future of reading to everyone!