My Course Creator Journey

My Course Creator Journey
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“How can I be more like Andrew Barry? How can I turn the content that I’m teaching in real-time into evergreen content? How can I show up and be the master of facilitation instead of always being the sage on the stage?”

By most accounts, ODCC was a colossal success executed in only four months.

But I’m here to tell you that launching a successful online course takes years of work that you don’t see.

For me that was 15 years

My goal with this essay is to tell my story. To share the lessons I learned along the way, which compounded little by little. To point out the mistakes I made so you can avoid them and accelerate the compounding. Ultimately, I aim to provide a framework for you to apply to your specific knowledge; to your online course.

Just Getting Started

It all started, for me, when I joined KPMG.

Believe it or not, this was me.

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As a white guy in South Africa with dreadlocks, you could say there was something curious about me.

But I was accepted by the firm and qualified as a chartered accountant. I wanted to become the CEO of a prominent South African company until I realized what the work entailed. You see, auditing wasn’t for me. I understood how to do it, but I took no joy in doing it. What I really wanted to do was be in the group of five managers that would lead 1-week training workshops for us. That looked like a blast.

So I became a facilitator for audit training. It was the best job ever.

Putting In The Reps

For three weeks of the month, I would fly to a different city in South Africa and teach audit training. I met so many amazing people. I thrived in the independence of being a road warrior. And I experimented like crazy with how to teach. I used Sun Tzu’s Art of War as an allegory for risk assessment. I figured out a way to remember everyone’s name in a class of 50 (a feat that never ceased to amaze students who would test me at the end of the week).

I did this for about a year, eventually teaching managers and partners in the firm. I must’ve facilitated 40-50 workshops, easily over 200 days of training. I loved every single one of them.

Presenting on video-based training at DevLearn
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That’s putting in the reps.

My First Dose of Luck

A mentor of mine, Michael Ellis, was on a two-year secondment to the United States, and after a couple of months, he reached out to me to see if I wanted to join him. I jumped at it.

It meant giving up facilitating the training to sit in a cubicle and develop the training to ship worldwide for member firms to deliver.

I didn’t care. I was in a new country and developing quite a taste for learning how to teach.

Meanwhile, my mentors were becoming my unfair advantage.

Two years in the U.S. became three on the visa I had. The visa became a green card thanks to another great mentor of mine, Eileen Walsh. She was the partner-in-charge of the department, an absolute bad-ass who was one of the first female partners at KPMG in the male-dominated world of NYC consulting firms.

Adding to the 200 days of training in South Africa, I now had three years of training development under my belt.

Learning To Sell

It was time to learn how to sell.

Another great mentor, Tricia Maslov, hired me in a new department she had created: KPMG’s Executive Education service line. I became content lead (figuring out what executives needed to learn and finding people who could teach it) and head of business development (pitches, proposals, and presentations for custom training development for the firm’s clients).

I learned a lot in the role, managing a $1.4M workshop calendar, planning our flagship event in Las Vegas each year, setting up partnerships, and convincing busy people that learning events were worth their time.

After two years, it was time to move on. I always had the urge to run my own thing. You know when someone reflects for you a truth about you? That happened to me during a Dale Carnegie speaking course I took. I got friendly with the facilitator, and after two days of working together, he said to me, “you’re not cut out for this corporate life, are you?”

He didn’t even meet me when I had dreadlocks.

Learning To Teach Through Video

I joined a small company called Lobster Ink.

A hospitality training company, it was started by friends of mine in South Africa. When they made it big by signing Accor as a client and investor, they relocated to Geneva. I opened their NYC office. We were expanding rapidly, adding Marriott, Hilton, and InterContinental as clients.

During my time at Lobster, I learned about the world of high-quality video production from our staff of recent film school graduates. I combined what I knew about live facilitation with techniques I was learning about asynchronous video training to create the official learning methodology of the company.

I honed my sales skills and learned how to run a business unit.

After almost two years, it was time to move on again—this time on my own.

On My Own At Last

Suddenly, and with no more support, I had to do it all. Create my methodology for client service. Deliver client service. Branding. Marketing. Sales. Hiring. Systems for scaling.

It’s fair to say I learned pretty inefficiently. I went down numerous dead-ends, sometimes for months at a time, before narrowing my focus and honing in on product-market-fit. I remember referring to Curious Lion using the royal “we” for a long time, wanting to appear more established than I was. By 2020, four years in, I finally saw the power of building in public, open kimono style. But that’s jumping ahead in the story.

The Online Course Bug

I first discovered the world of online courses in 2016, not too long after starting Curious Lion and a scrappy startup called Fedora became Teachable.

Dynamic female creators dominated the online course world with beautiful websites and names beginning with M: Maria Forleo, Mariah Coz, Melyssa Griffin. My first course was a branding and social media course from Melyssa. I got hooked.

I became obsessed with launching a course of my own. Hilariously, I launched one right around this time on “how to start a business” – everything from forming an LLC to validating an idea. It was laughably broad and ill-conceived. Plus, I had no credibility; I had just done it once!

I launched another course on how to grow a B2B business using LinkedIn a few years later. This time I had done the thing successfully a few times with a small agency I owned. The course did ok, lasting two cohorts and converting a few students into monthly clients. My lesson with this one was that I wasn’t passionate enough about the topic. I had no appetite for creating the volume of valuable content required to grow an audience.

My Online Course Transformation

My first taste of cohort-based courses (CBCs) was in June 2019, when I took Tiago Forte’s Building a Second Brain. It was my first encounter with transformation. Suddenly I had a method for capturing, organizing, and processing everything I was consuming. Once again, I got hooked.

I went to a workshop in Brooklyn that Tiago hosted with his friend and new collaborator, David Perell. I read David’s 10-year vision for his course, Write of Passage. I signed up immediately for cohort 3. It was so far out of my comfort zone. Here was this guy with thousands of followers teaching me how to build an audience by writing online. Everywhere I looked, it felt like everyone had it figured out. I withdrew from the community part of the course. I left with some great ideas but no transformation this time.

Fast forward six months, and I see an email about a mentor program for Write of Passage. Here was a chance to go behind the scenes of a course I admired. I applied immediately and somehow got accepted.

The imposter syndrome came flooding back again as I assumed the mantle of mentor for students of cohort 5. My mentor sessions became a space to chat about the challenges of writing online. As my mentees opened up, my confidence grew. I met some fantastic, supportive people at a similar stage of the journey as me. Most profoundly, I realized we were all on a journey together, some at different stages.

I left WoP 5 transformed once again.

Making friends in online group learning
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I immediately joined my new friend from WoP 5, Robbie Crabtree, in his first cohort of Performative Speaking. I rated myself a decent speaker going in, but I left transformed for the third time in 18 months. If there were a way to mainline online courses, I would do it.

Student Becomes Professor

Thanks to my friendship with Robbie, I began informally advising him on his course while taking it. I didn’t realize yet how valuable my 15 years of experience would be for course creators.

That all changed when I started decoding what top course creators were doing.

I started writing threads on Twitter sharing source material from the learning methodology I had crafted for Curious Lion over my career.

A tipping point came with an article I was writing on group learning. I posted this tweet:

Tiago responded!

Suddenly I had 12-15 generous souls in a Google Doc, carving up my rough clay into a compelling narrative that became my article on Destination and Journey groups.

you need both to make a transformation.
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Name It and Claim It

I followed that idea up with another one that quickly became the thing I was known for: Transformational Online Courses.

The power of naming something is profound. It gives people a lens through which to view the world. As Confucius said when referring to observation and awareness, “the beginning of wisdom is to call things by their proper name.” Giving my small band of merry followers a proper name to use for my teaching was pivotal.

Finding the Others

I was now taking publishing seriously. I created more than I consumed. Around this time our son was born. I would wake up at 5 am to write for an hour before he woke up. I would publish essays and threads every day. My ideas started to get taken seriously.

That message from Ali was a turning point. I began advising him, and in exchange, I learned directly from him about creating a YouTube channel.

I hopped on calls with Marie Poulin, Will Mannon, August Bradley, and Eric Jorgenson to nerd out about online courses.

I hopped on calls with people with small audiences too, and each time I learned something new about my audience.

Content Machine

With my essays and tweets fueling growth, I doubled down on creating content by starting my podcast on November 4, 2020. Encouraged by my friend from the online course world, Paul Le Crone, I dusted off the mic from my first failed online course (yes, I bought the gear and everything back then!) and asked Paul if he’d be my first guest. We had a wonderful first conversation.

Putting one baby step in front of the other, I invited another friend and another. The feedback coming in was positive. My confidence in the new medium grew, so I started reaching out to people with bigger audiences – Chris Sparks, Marie Poulin, and Alex & Books. I was off to the races.

How did you learn that podcast cover art
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One of the benefits of my podcast was that each conversation became an almost infinite well of quality content I could use for threads, essay ideas, short videos, and audio clips. I never knew this when I first started it.

Getting in Front of Bigger Audiences

The friendships I was making in the online course world started to gain exposure to new audiences for me.

Thanks to my help behind the scenes for Ali Abdaal, he invited me to present a workshop in Part-Time YouTuber Academy: 100+ attendees.

After working with Billy Broas and helping him with his design of Keystone Accelerator, I presented another workshop: 30+ course creators.

By being helpful in Ness Labs, and thanks to the generosity of Anne-Laure Le Cunff, I did a workshop for her community: 40+ course creators.

Podcast guests were sharing my content. I was getting invited to appear on other people’s podcasts. This all added up.

I realized that when building an audience it’s easy to worry about numbers: followers, subscribers, Clubhouse attendance. But all it takes is one person to change the course of your life or business. My motto became: default to yes.

Building in Public

Momentum was tangible. It finally felt like time to commit to what I wanted to do. Launch an online course of the most meta variety: a course about courses.

I made the public commitment on November 22, 2020 (I’m sharing exact dates, so you get a sense of how quickly things moved).

I spun up a straightforward landing page to test interest. I got 70 sign-ups in the first week. Idea validated (to an extent – I hadn’t asked people to pay yet).

I ran free workshops for course-curious creators. I wanted to provide value and advice while at the same time understand what their challenges were. Here are actual notes from one of those workshops:

Notes from workshop
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The workshops provided new ideas for content. My content machine was growing with the podcast, and my content production kept churning out value.

Developing Strategic Partnerships

On December 13, 2020, I received a Twitter DM from Erik Torenberg, the founder of On Deck.

He had seen that I was writing about online courses. With my son Leo strapped to my chest walking along the waterfront of Long Island City, NYC, we jumped on a call on a brisk Saturday morning.

Joining On Deck with Leo
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We talked for over an hour. You can read more about my story of joining On Deck here.

In Superstar Teachers, I wrote about the power of developing strategic partnerships. Joining On Deck was an accelerator for my Transformational Online Course idea. My goal for the course in two years was now achievable in four months.

My course idea was still very much in beta, so there was quite a bit of risk in scaling this quickly. I was building the plane while flying it. Only I was piloting the inaugural trans-Atlantic version of the program with a lot of people watching.

Thanks to the support of a small but mighty crew, we pulled off the landing.

In four months, we had announced, developed, launched, and ran a wildly successful first cohort by many accounts.

150 students. $350K+ in revenue. $40K+ in scholarships. Dozens of transformations.

After the first cohort, On Deck and I agreed to part ways to focus on our core businesses respectively. You can read more about my story of leaving On Deck here.

The Future is a Collective Effort

I’m grateful for the opportunity and momentum that On Deck provided.

Now it’s time to flesh this idea out and realize its full potential.

What is that potential, you ask?

I believe that everyone has an online course in them. If you’ve helped a handful of people improve their life or business with your specific knowledge, you can leverage the power of teaching on the internet to scale that impact.

Teaching on the internet, like any skill, can be learned.

But for those who want to take their online course seriously, there are many moving parts and a never-ending series of experiments to run as a business. To be uncommonly successful, you need a community.

Community, after all, is leverage. Think of country clubs. You pay to join and relax or play sport with other similarly affluent members. The network you buy provides access to opportunities, ideas, advice, deals, and ultimately, success.

There is no such community for course creators.

Until now.

The future of Transformational Online Courses and Superstar Teachers is collective.

The Course Creators Collective Guides
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Together with Robbie Crabtree and Marie Poulin, we’re building a community that feels like home, inclusive of all, and way more accessible than your local country club. Entrepreneur Course Creators will have a place to learn from, support, and encourage each other while receiving personalized coaching advice from me and two of the best course creators I know.

Imagine for a moment what the impact of this will be on students across the globe.

If we can meaningfully increase the supply of Superstar Teachers, might we finally make a meaningful impact on democratizing education?

That’s the vision.

The mission will be brick-by-brick. Creator-by-creator. It will take years of work that you don’t see.


Lessons Learned

In writing this post, I found myself documenting lessons learned along the way as reminders to myself. Here they are for your benefit too.

  1. Credibility comes from putting in the reps, producing results, and doing this for years to develop mental representations you understand well enough to decode for others.
  2. You have to have a passion for what you teach. If you love what you do, two things will happen. Students will experience the same joy you feel, and you’ll have the energy needed to produce the mountains of quality content required to attract more students.
  3. Your job as a course creator is to explain, illustrate, describe what you and top performers in your field are doing so that others can do it too. Create frameworks for others to follow. Make the complex clear and easy to copy.
  4. Give your tribe a proper name to use for what you teach. Give your frameworks memorable names too.
  5. Record conversations with interesting people for an almost infinite well of quality content for repurposing.
  6. If you’re “building an audience”, don’t worry about numbers – followers, subscribers, Clubhouse attendance. All it takes is one person to change things for you. Default to yes.
  7. Never stop providing value. If you want to build an audience, be relentless in delivering insane value consistently.
  8. When launching a course, start small. Trust me; it’s a trial by fire if you do your first cohort for 150 people.
  9. If you start with 150 people, brace yourself for 150 opinions that will make your course 150,000 times better. It takes some getting used to, but it’s worth it if you’re ready for it.
  10. Adopt an attitude of “how can I help you” in everything you do.
  11. Build a team.
  12. Do not take criticism personally. It will only make you feel ugly (h/t Baz Luhrman).
  13. Make everything you do in your course about your student and their transformation.
  14. Make everything you do before your course about understanding consumer psychology.
  15. Running a live cohort is one of the most exhausting things you can do. If you’re not exhausted, your heart’s not in it. If your heart’s not in it, it won’t be a long-term success.
  16. Live cohorts are not the be-all and end-all. Think of them as a block with which to build your course. Other types of blocks include curated content, recorded videos, audio content, activities, and community.
  17. Be intentional about building community – it’s a full-time job (see the one about building a team).
  18. Take the time to listen to students, or run the risk of becoming the Course Creator with No Clothes.
  19. Your students will learn as much, if not more, from what you do as from what you say. Lead by example.
  20. Find joy in what you do and share that with students. This feeling is contagious and is what they’ll remember the most when it’s over. 
My Course Creator Journey
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