17 years ago, at the age of 22, I uploaded my first YouTube video.
My high school friend Derick and I had set up a digital camcorder, faced the camera with our backs to his bedroom wall, hit record, and just started talking about 3D printing, which was to be the first episode in a recurring show about emerging future trends.
Needless to say, our show never had an episode two, but something was sparked in me that day. I saw that I could share a message with the entire world from my bedroom, without permission from anyone. All I needed was a message worth sharing. It would take me 14 years to find one.
I distinctly remember feeling back then, in 2007, that I was too late. I thought I had already missed the golden era of online video. Little did I know, those were prehistoric times, revealing only the faintest glimmer of what the YouTube empire would eventually become.
This piece is a comprehensive retrospective of my 17 years of experience on YouTube, including my path to 275,000 subscribers and 12 million views. It is a deep dive into the different “eras” I’ve moved through, the team and production process I’ve built, and the detailed finances throughout.
I’ll summarize for you what I’ve learned so far, analyze my successes and failures alike, and distill practical insights that you can use in your own YouTube efforts. Whether you aspire to create YouTube videos in the future, or are already doing so now, my hope is that these lessons will shorten your learning curve and save you from making the same mistakes I made.
Even after all these years and some notable successes, we still haven’t figured out a business model for YouTube that is sustainable for the long term, so this piece will also serve as a springboard for the next era of our channel.
The 4 Eras of My YouTube Journey
I’ve gone through four distinct “eras” in my time on YouTube, each one with a central theme:
- The Experiment Era (2007-2012): Performing random experiments and trying things out
- The Portfolio Era (2013-2020): Using YouTube as a professional portfolio
- The Startup Era (2021-2023): Starting to take YouTube seriously
- The Factory Era (2023–2024): Building a full production process
Each era lasted between 1 and 7 years, and they seem to be getting shorter over time as we iterate more quickly. These years encompass my entire adulthood, and reflect the stages of my growth both professionally, creatively, and as a human being.
Let’s dive into each era one at a time.
The Experiment Era (2007-2012)
The first era I think of as a series of crackpot experiments, dating from that first grainy video uploaded from my friend’s bedroom to the start of my professional career.
In that time I uploaded anything and everything I could think of, from photo slideshows showcasing my volunteering work in Rio de Janeiro, to profiles of microentrepreneurs in support of my microfinance work in Colombia, to short clips of my adventures across South America, to highlight reels from my Peace Corps service in Ukraine.
I had no particular goal, vision, or mission for what I wanted to do on YouTube. I thought of it as a social media site, like Myspace or Facebook – a place for me to share updates about my life and travels and to document my experiences for future record.
And yet some of the most basic lessons I learned during this period were essential, forming a foundation for everything that would come later: how to point a camera, frame an interesting shot, make sure the audio was working, and import it all to a computer to make simple edits and add appropriate music.
In this first experimental era I made 19 videos, which drew 7,411 views and 20.8 hours of watch time from a grand total of 3 subscribers, one of whom was my mom!
The Portfolio Era (2013-2020)
In early 2012 I returned from my Peace Corps service in Ukraine, excited to finally begin my professional career in the big city.
After working in consulting for a couple years, I struck out on my own as a freelancer in June 2013. To mark the occasion, I uploaded my first “professional” video, a 102-minute long recording of a workshop I had delivered at a coworking space in downtown San Francisco.
That video frankly left a lot to be desired. The video and audio quality were quite poor, there was no lead-in or introduction, no titles or animations, and no link to the slides. I had not yet heard of concepts like virality or retention.
And yet, this early video already contained within it some promising signs of YouTube’s potential. It demonstrated that I could expand the reach of my ideas via digital video. It showed me that there was a place for educational content amidst the deluge of endless clickbait. And by including a link in the description to my first product, an online course teaching the Getting Things Done methodology in more detail, it proved that I could find customers by sharing content freely on the web.
All these seemed like earthshaking realizations at the time. With a single video, I could already see the outlines of a holistic online education business, from testing and validating ideas, to gathering feedback, to building community, to finding customers, to serving them with valuable products.
Despite all the limitations and flaws in what I had created, the essential quality of the material I was teaching managed to shine through, and it soon gathered thousands of views, which at the time felt like a big deal.
I forged ahead, uploading the first lesson of my course as a preview, and then a short promotional trailer filmed by a friend in an afternoon. I later leveled up the production values, hiring a videographer to film a Design Thinking workshop I was beginning to offer companies.
As sales of my first course dwindled over time, and a subsequent one I launched fizzled, I decided to set aside online courses to focus on where I knew I could make money: talks and workshops for companies. My YouTube channel accompanied me on this pivot, becoming essentially my “speaker’s reel.”
I spoke on emerging trends such as the Quantified Self movement, new theories of innovation, and shared my personal experiments in using network science to analyze my habits. My attitude was that I would speak for free if needed, as long as I could come away with a recording I could add to my YouTube channel – a tangible, publicly visible “proof of work” that I could point to for future gigs.
After a couple years, I was fed up with corporate work and wanted to return to where I began – teaching people directly online. I had started a blog in 2014 and found that writing was a crucial medium to fully work through the details and implications of my ideas. After writing dozens of in-depth essays, I decided to take my most successful piece, on how I used Evernote as a “second brain,” and turn it into a full-fledged course.
YouTube again played a crucial role in this new chapter. I published testimonial videos from my earliest cohort students, recordings of Q&As, interviews with experts, quick demos and case studies of PKM tools and techniques, recordings of talks on the subject I delivered, and a promotional trailer for my course, which I called Building a Second Brain. I also continued experimenting with personal interests and developing my videography skills during this period, such as with the documentary I created on my father’s life and artistic career once I realized that smartphone cameras were up to the task.
Five years after I wrote my first essay on the subject of Personal Knowledge Management, and two years into teaching the Building a Second Brain course as my sole focus, I uploaded a video that encapsulated for the first time my Second Brain methodology. In many ways, it was the culmination of the first six years of my career, incorporating ideas and insights from a dozen subjects I had researched, taught, and coached on in search of my niche.
It was my first “viral” video, reaching hundreds of thousands of views and serving as the default place to send people for an introduction to me and my work.
I had just begun exploring the possibility of publishing a book in early 2019 when this video came out, and it became the first true test of my holistic methodology. Nothing about the video is optimized or particularly strategic. It’s just a bunch of slides with voiceover, a decidedly low-tech style that didn’t even require a camera – just a computer and a mic.
And yet, it’s difficult to overstate the impact this single video had on my career. It served as an incredibly effective delivery vehicle for introducing a complex topic to a wide variety of new people, including my future book agent and publisher, who in turn would help me spread my message to even more audiences far from my home base.
During this second YouTube era, which lasted seven years, I released 113 videos drawing 885,000 views, 101,000 hours of watch time, and gaining 20,454 subscribers. This small but promising start laid the foundation for the next era, when I would begin to invest in YouTube seriously and make it the focus of my content creation.
The Startup Era (2021-2023)
In July of 2021 I realized that we had only one year left until the release of my book, and I wanted to invest the book advances I’d received from various countries to make the biggest splash possible. This was also a few months after our largest-ever cohort (fueled by the pandemic), meaning I had substantial resources on hand to do so.
After looking at a variety of avenues, I decided making YouTube our primary focus was the most promising path we could take, for several reasons that remain just as or even more valid today:
- YouTube is the world’s most widely used and most influential platform for educational content, reaching millions of people with a highly accessible form of media that anyone can consume and benefit from.
- The algorithmic reach of YouTube is a powerful mechanism for continuously reaching new audiences beyond our original niche.
- Video production is expensive and time-consuming, but my business was finally at a place where we could afford to make those investments.
- Videos can be produced as a collaboration between a team, rather than relying solely on my personal time and energy as with writing.
By this point, I’d been experimenting on my own and uploading all kinds of videos for years, and knew I needed a different approach if I was going to change the trajectory of the channel and make it a long-term driver of book and course sales.
I’d reached 20,000 subscribers through my own personal efforts, but it had taken many years to do so, and I knew I now had less time and energy to dedicate to video creation with a toddler running around the house and a second baby on the way in a few months. I needed to find a way to massively level up both the quantity and quality of our videos, while also delegating most of the necessary work to my team so it didn’t fall on my shoulders.
I started at the most fundamental level of the videos I wanted to create – with a dedicated place where they could be made. My wife and I decided to extensively remodel our two-car garage, including new tile, an attractive brick facade along one wall, new electrical wiring and lighting, high-end cabinets along another wall, and stylishly modern furniture and interior design throughout, tastefully chosen by my wife Lauren according to a “Mexico City cafe” aesthetic.
Between the $50,000 remodel, $30,000 in cameras and other equipment, and $20,000 in consultants, we would eventually spend about $100,000 making the ultimate home studio, as I’ll detail further below. You can see a video recapping the project here.
The next step was to hire someone to lead our YouTube efforts, since I knew I wouldn’t be able to remain hands-on all the time. After a wide-ranging search, I hired Marc Koenig as our first Creative Director to lead our overall YouTube strategy as well as provide creative direction for our videos from beginning to end.
It took more than 4 months from when Marc joined to the release of our first video in January 2022. This included everything from buying cameras and microphones and lighting, to brainstorming the kinds of videos we wanted to create, to establishing the initial team and the workflow they would use, to experimenting with test shots in the studio.
We bought specialized furniture, cameras, microphones, lighting, rigging, computers, editing software, hard drives, and various other tools. We recruited a video editor, a production assistant, and several thumbnail designers. Marc flew out from Wisconsin a number of times to help set up our gear, brainstorm ideas, and iterate on everything from the framing of shots to how we would write scripts to my live performance on camera. We mapped out the first year of videos we wanted to create, scheduled a trip to the East coast and Europe to record a series of interviews with leading experts in our field, and built the beginnings of a production workflow to coordinate everyone who would be contributing.
We also hired a studio design consultant, Kevin Shen, who spent a couple weeks helping us improve our production setup and teaching me the basics of how images, sound, and light interact to produce a holistic effect for the viewer. I gave Kevin the mandate to help us make a “classroom that can teach the entire world,” encompassing not only filming videos but also teaching cohorts on Zoom, working and writing day to day, joining meetings with the remote team, recording interviews with guests, and more. It was a small 320-square-foot space that needed to elegantly straddle the physical and digital worlds while projecting a compelling message to the world.
All this was an incredible amount of work, and took much longer than I expected. There were so many twists and turns, for example:
- We had to buy a commercial-grade AC unit to make sure we weren’t sweating on camera, and to minimize the risk of cameras overheating.
- We needed a backup battery to keep everything online even during a power outage, and a second Internet connection in case the primary one went down.
- We found we needed full blackout curtains across every window to be able to keep the lighting constant, and a door with an access code so various people could come in and out at all hours of the day.
- Lights had to be mounted on walls or ceilings and folded away so we could use the space as an office whenever we weren’t filming.
We faced a constant tradeoff between aesthetics and functionality – we didn’t want an ugly space that we wouldn’t want to spend time in, nor a beautiful one that didn’t support our needs. This creative constraint led to a number of innovative solutions, such as using sound blankets that could be put away instead of wall-mounted pads.
Here’s the “before and after” comparison: