MasterClass: Top 10 recommendations for EdTech’s most star-studded platform

Armchair Consulting is a series of articles where I make marketing suggestions for businesses I love. If you’re involved with MasterClass and you want to connect, contact me here.

MasterClass: Top 10 recommendations for EdTech’s most star-studded platform

Armchair Consulting is a series of articles where I make marketing suggestions for businesses I love. If you’re involved with MasterClass and you want to connect, contact me here.

When I was a kid I wanted to be a screenwriter.

I read every book and blog and forum on screenwriting and pumped out dozens of scripts that never saw the light of day (thank God, they were terrible).

Despite drifting away from Hollywood, I never quite shook my showbiz tendencies—so when I saw that Aaron Sorkin (A Few Good Men, The West Wing) was teaching an online class in 2016, I promptly signed up.

Aaron Sorkin's was the first MasterClass I took back when I still had delusions of becoming a Hollywood screenwriter

That was my introduction to MasterClass.

Since then, I’ve completed classes from Steve Martin, James Suckling, Bob Iger, Ron Finley, Anna Wintour, Lynnette Marrero & Ryan Chetiyawardana, and Margaret Atwood.

Beyond its instructors, I think there’s something magnetic about the MasterClass brand itself.

It’s as polished as Netflix.

As premium as Rolex.

As affordable as LinkedIn Learning.

I’ve followed its evolution from one-off courses to subscription-based memberships and kept an eye on its expanding list of classes for years now. So imagine my delight when I was scrolling through LinkedIn a few weeks ago and saw…

“MasterClass just raised $100M for celebrity-fueled content”

Being a marketing nerd, I whipped open Google Docs and started jotting down demand gen and product ideas because, y’know, this is apparently how I stay sane during a pandemic.

Like many rocket ships, MasterClass is a great company with loads of room for improvement. If I were in charge of marketing and strategy, here’s what I’d do with $100 million.

Top 10 recommendations for MasterClass

1. Focus on certifications

As soon as I heard MasterClass raised $100M, I called up my friend Dennis Yu for his reaction.

Dennis is THE guy in e-learning and digital courses. He’s been featured in the Wall Street Journal, New York Times, LA Times, NPR, and TechCrunch, and he also authored Facebook Nation—a textbook taught in over 700 colleges and universities.

I asked Dennis: “If you were CEO of MasterClass, how would you spend $100M?”

Here’s what he had to say…

Dennis’ response to “If you were CEO of MasterClass, how would you spend $100M?”

The gist? Certifications, certifications, certifications.

“MasterClass courses are shot well, but they’re really just high-production-quality webinars,” Dennis says. “To take it to the next level—to go from a one-time fee to a true recurring subscription—they have to offer certification. Real cooking, real athletics, real singing…which leads to jobs. Especially now when employment is at an all-time high.”

To expand on what Dennis is saying, what matters most is the same thing that colleges and universities obsess over: the success of their alumni.

To help people succeed, there needs to be an element of hands-on training and practice that goes beyond recorded videos.

It’s not just cooking taught by Gordan Ramsay; it’s also practice at a local culinary school.

It’s not just music production taught by Deadmau5; it’s also time spent in a recording studio.

It’s not just comedy tips from Steve Martin; it’s also hours of testing jokes at open mics.

By pairing courses with real certifications and training, MasterClass can improve the success of its learners

If MasterClass disagrees with this approach—i.e., supplementing their courses with training and certifications from a network of accessible institutions—they’ll continue to be seen as “edutainment” and risk extremely high churn.

As Dennis says: “People buy aspirationally but don’t actually take action. If I was running MasterClass, I would figure out ‘How do we go beyond a $99 buy-one-get-one-free [subscription] that is primarily during Christmastime…toward making that the first step of a lead gen funnel to then sell a real certification?’”

The answer? Provide job-related value on top of edutainment. Start with a learning management system (LMS) to form the foundation of an interactive platform with quizzes and badges and then expand through partnerships to supplement courses with full accreditation.

2. Sell products with courses

Another of Dennis’ ideas I agree with is selling products alongside courses.

  • “Take Serena’s course and purchase the same gear she uses on the court”
  • “Watch Ron Finley garden and get a list of links to the tools in his shed”
  • “Learn how to barbecue from Aaron Franklin and buy the same rubs, spices, sauces, brushes, and smokers he has in his kitchen”

Offering products with courses is so obvious I'm sure MasterClass has talked about it at length internally

I appreciate the difficulty of navigating celebrity endorsements—a minefield of brand managers, legal teams, and agents—but there’s no question everyone stands to gain a lot.

I’d be very surprised if MasterClass couldn’t make more off brand deals than actual courses.

3. Create a community of learners

Learners crave interaction and accountability with other learners.

It’s one thing to teach someone how to do something and another to change their behavior. By implementing online groups, accountability pods, badging systems, and content libraries, MasterClass could see learners self-organize, motivate each other, and build connections that advance their professional goals in ways far beyond what currently exists.

The other benefit of an online community is user-generated content.

Naturally, students have tons of questions. Even the best courses need support materials, and students can help create it themselves and find answers to each other’s problems.

What ends up happening is actually viral growth.

One student develops a checklist or guide or template that’s valuable for other students, and it spreads through the nature of its use.

By leveraging user-generated content, MasterClass can create growth loops at scale

I’ve seen it time and time again. My marketing team has a small-ish content group (10 people) who can’t possibly tackle all the topics we want to cover. Our learner community, however, has been a godsend. We now have people creating content that’s ranking in Google and helping with both acquisition and retention—all for free. How great is that?

Brian Balfour’s Reforge series talks extensively about user-generated loops. If you have 30 minutes, I recommend watching this video.

Balfour’s insights around growth loops. If the execs at MasterClass haven’t gone through Reforge yet, they should.

Whether MasterClass decides to roll out its own community or strategically pinpoint areas where they can get more user-generated content, it’s a smart move. Not only will more engagement help with retention, but it will also move their acquisition strategy in the direction of organic growth—and that’s *chef’s kiss* because paid advertising should never be the primary driver of acquisition (which I strongly suspect is the case right now).

P.S. If MasterClass doesn’t organize their own community, learners will organize themselves anyway. It’s better to own the conversations in your own ecosystem rather than having them float around externally for the benefits of search and brand.

4. Triple down on business content

According to TC, former FBI agent Chris Voss is MasterClass’s most popular instructor.

I’m not surprised. I’ve read Chris’ book Never Split the Difference and it’s excellent for anyone looking to improve their negotiating skills.

The fact that Voss is their top instructor tells me that business courses are key.

I would put considerable effort into recruiting other business leaders and selling courses at scale to companies instead of one-off consumers.

The list of sharks on Shark Tank seems like a good place to start.

  • Kevin O’Leary
  • Barbara Corcoran
  • Daymond John
  • Robert Herjavec
  • Kevin Harrington
  • Mark Cuban
  • Lori Greiner
  • Jeff Foxworthy
  • Steve Tisch
  • John Paul DeJoria
  • Nick Woodman
  • Ashton Kutcher
  • Troy Carter
  • Chris Sacca
  • Richard Branson
  • Rohan Oza
  • Alex Rodriguez
  • Sara Blakely
  • Bethenny Frankel
  • Charles Barkley
  • Matt Higgins
  • Jamie Siminoff
  • Alli Webb
  • Daniel Lubetzky
  • Anne Wojcicki
  • Katrina Lake
  • Maria Sharapova

After draining the shark tank, I’d reach out to speakers from major business conferences like Cardone’s 10X Growth Conference, HubSpot’s Inbound, and Salesforce’s Dreamforce. B2B conferences do a great job coming up with creative ideas for high-profile speakers whose messages have a business angle.

Last but not least, I would spin up a sub-brand to include courses from non-celebrities who are extremely accomplished in their fields.

Call it MasterClass+ or MasterClass Enterprise or something, similar to TedX.

This brand would include C-Suite members from Fortune 500 companies, serial entrepreneurs, and other professionals who are no strangers to conferences. They wouldn’t be celebrities, so to speak, but they’d have enough authority to teach others about running businesses.

The benefit of more business-focused content is that the audience is companies. Suddenly you can sell group memberships to organizations and justify it under professional development. It’s easier to scale when you can sell hundreds of licenses at once versus one by one.

5. Get into the conference game

It feels weird to talk about conferences when they’re all cancelled, but life will return to normal—and when it does, MasterClass should be ready

Marketdata estimates the speakers’ market in the US generated $1.9 billion in 2019. It’s projected to grow 4.1% average per year, reaching $2.3 billion by 2025.

Shy of starting their own management division for speaking circuits (which might not be a bad idea), MasterClass could work out deals with the agencies that rep their instructors to bring their brand to conferences in a BIG way.

Essentially, I’m picturing MasterClass providing A-list speakers to top tier conferences in exchange for heavy brand presence.

MasterClass could team up with top-tier conferences to offer talent in exchange for exposure, preferably around the launch of a business-focused sub-brand

This would be 10x more effective if combined with the idea in the previous section—i.e., launching a business-focused sub-brand. You could choose 3 or 4 of the biggest business conferences (Dreamforce, CES, Inbound, etc.) and provide them with speakers in order to get in front of hundreds of thousands of people. That’s a helluva launch.

Alternately, MasterClass could launch its own conference.

Close your eyes and picture this…

  • In-person keynotes from top instructors on the MasterClass platform
  • Breakout areas to get hands-on training from professionals in your field
  • Networking events for different streams (cooking, filmmaking, athletics, etc.)
  • Vendor floors full of sponsored booths for products and services
  • Talkback sessions and fireside chats where you can interact with instructors

And get this: you could even do it in a way that leverages the students themselves.

For example, those who come to learn about cooking could cook for everyone at the show. The bartending students could bartend. Those who come to learn about video could document it. The athletes and singers and comedians could provide entertainment.

How meta and cool is that?!

Putting on a conference is an order of magnitude more expensive than sponsoring other conferences…but I can’t help think “high risk, high reward”. Brand-wise, a premium event might be the type of thing that skyrockets the brand to new heights.

6. Expand with strategic partnerships

What would a MasterClass and Duolingo partnership look like?

Or MasterClass and LinkedIn Learning?

Or MasterClass and TED? Udemy? Udacity?

With EdTech’s explosion, there are strategic partnership opportunities everywhere. I would experiment with at least 1 or 2 co-branded initiatives per year to test the waters.

I would also look at companies like Cameo, Starsona, and Greetzly very closely.

These “celebrity marketplaces” could add an interesting element to the brand. People are already paying for access to influencers through these apps; perhaps there’s an opportunity to use the tech for those who want extra feedback or 1:1 time with their instructors?

Who knows. Could be a cool partnership, could be M&A. Could be nothing. I wouldn’t combine the MasterClass and Cameo brands but I’d find a way to make them work together.

7. Internationalize through data

Internationalization, or I18N for the lazy (so called because there are 18 letters between the “i” and “n”), makes a lot of sense for MasterClass. In fact, I’d bet my bottom dollar it was outlined as a key initiative during the raise.

Currently, only 7 of their courses have subtitles available in Spanish and German.

I’d prioritize more translations and add other languages to the list since that’s a relatively low cost-of-entry to new markets.

From there, I’d look at top courses and user segments to create “IPPs” (ideal professor profiles) and find celebrity instructors from other countries who fit the criteria.

This is where regression, cluster and cohort analysis, and other data modeling techniques are crucial. For example…

  • Are there pockets of MasterClass subscribers from Mexico with low churn characteristics who watch a lot of acting courses? If so, add some telenovela actors!
  • Are some of the most active users outside the US in India with an interest in sports? Get some legendary cricket players!
  • Are there a lot of cooking students with high LTV and low CAC from Japan? Add Japanese subtitles to more courses and find a celebrity chef in Tokyo!

Bottom line: internationalization decisions shouldn’t be based on educated guesses and executive opinions. They should be moneyballed. Data driven. Use all available metrics to make smarter and smarter moves.

8. Add nudges and email automation

Back to Dennis’ quote in section one: “People buy aspirationally but don’t actually take action.”

One thing that helps with this is the concept of nudges.

In its simplest form, I’m talking about email reminders. Nothing fancy.

Most MasterClass videos already end with summaries and workbooks to supplement the videos. Unfortunately, the workbooks are buried in the UI and inaccessible if you’re watching the videos through the app on your TV.

Ideally, workbooks should be cut into checklists that are automatically emailed to learners after every episode. Unless you get homework into a person’s hands and tell them “do this, then this, then this” they likely won’t do it.

James Suckling’s wine appreciation workbook. I took the whole course without knowing this existed until later. It should’ve been emailed to me and turned into checklists of things to do.

After the homework is emailed, it needs to be followed up with regularly.

This is where nudges come in.

With marketing automation systems, you can set up different tracks of emails to remind people to do their homework, motivate them with the reasons they signed up in the first place, and encourage them to share their struggles and wins with others.

I know nurturing logic can get overwhelming fast. To start with, make sure every workbook has a clear checklist and then launch simple campaigns to get them into the hands of students.

9. Return to deeper content

The #1 complaint I hear when I talk to MasterClass students is that the content is too surface level and not tactical enough.

Let’s talk about Chris Voss again. Voss’ course is successful because he teaches tactical empathy. I.e., exercises you can practice. Meanwhile, other business classes are fluffy and feel more like documentaries than learning opportunities.

Personally, I find a lot of the older courses like Aaron Sorkin’s more in-depth.

Maybe some of the newer ones are rushed due to tight schedules (understandable), but it’s worth being honest with the talent upfront and saying, “Look, we can shoot this in an afternoon or two but it might not reflect positively on your brand. If you want a great MasterClass, it’s going to take time and effort.”

If I were heading up production, I’d raise the bar on the depth of content expected from instructors and hire more instructional designers to craft it. If someone can’t make the commitment, I would politely decline. MasterClass is past the point of needing high-profile names for the sake of names. It will live or die based on the caliber of its content, nothing else.

10. Rethink org structure

More important than any strategy in this article is company culture.

As Peter Drucker said…

I don’t know if MasterClass has culture issues; however, 3.9 on Glassdoor isn’t necessarily best-in-class. It’s likely due to growing pains. Still, it made me think about my own SaaS journey from $5M ARR to +$30M ARR and the hurdles along the way.

Recently, my company has restructured around cross-functional “squads” rather than traditional silos. It’s similar to what Spotify and others do with tribes.

The difference is night and day.

Instead of product, sales, marketing, and customer success living on separate islands, they’re joined at the hip. They set goals together, they sit together, they celebrate together.

Why is this important for platforms like MasterClass?

It’s related to Conway’s Law: “organizations design systems that mirror their own communication structure.” By designing better structures, everything else improves dramatically. With squads (at least in my experience), you can design your org around the logical stages of a customer journey—e.g., pre-purchase exploration, post-purchase experience, and stability/growth—and in doing so, you guide customers through those stages faster.

At the end of the day, the goal is high autonomy and high alignment.

To get there, I’d consider forming cross-functional teams of marketers, developers, designers, operations, sales, and success around squads like these:

  • Acquisition – Focused on generating awareness and new subscribers
  • Activation – Focused on the success of new users, from initial signup to forming habits around “aha moments”
  • Retention & Growth – Focused on long-term retention and engagement with a mission of minimizing churn and maximizing lifetime value

This helps avoid the temptation of introducing “growth teams” with fuzzy KPIs. In essence, growth becomes everyone’s job.

Once you have the teams, make sure they’re rallied around use cases and metrics.

For example, the use cases at Airbnb look something like this…

Once you’ve figured these out and you’ve released cross-functional teams to tackle them, that’s when the magic happens.

Tinkering with org structure isn’t easy, but in my experience it’s the most important thing when there’s an injection of cash and people. Get it right and life is heaven. Get it wrong? Hell.

In Summary

As Warren Buffett said: “The monetization of hope is a way to make a huge amount of money.”

That’s the business MasterClass is in: monetizing hope. It’s a powerful business model that can go wrong if it doesn’t deliver on its promise, but with these 10 ideas I’m confident they can scale sustainably.

  1. Focus on certifications
  2. Sell products with courses
  3. Create a community of learners
  4. Triple down on business content
  5. Get into the conference game
  6. Expand with strategic partnerships
  7. Internationalize through data
  8. Add nudges and email automation
  9. Return to deeper content
  10. Rethink org structure

As both a marketer and MasterClass subscriber, I’m a huge fan of the platform and I’m rooting for it. Can’t wait to see what happens with this $100M and beyond.

Are you from MasterClass?

Leapin’ lizards! If you’re interested in digging deeper into any of these ideas, I’m happy to hop on a call and nerd out. Contact me directly at

About the Author

Devon Hennig is a MasterClass fanboy with 10+ years experience as an executive in digital marketing. Follow along as he makes recommendations for businesses he loves.