10 Wins & 10 Lessons From Running My First Live, Cohort-Based Course

by | Dec 28, 2021 | General Information, How To's, Life | 2 comments

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I ran my first live, online, cohort-based course in August 2021.

The course was titled Mind Like Water (ft. Notion) (which is now renamed to More Time Everyday.) and it was aimed at helping students build a second brain using Notion, an all-in-one productivity tool, and more specifically build a robust planning workspace to lead their busy lives with more intention and balance.

I went 0 to 1 and launched the course within 8 weeks thanks to an incredible accelerator program that I went through with Maven, a startup that is building the platform to enable creators to launch cohort-based courses.



Having had time to reflect on my experience, this is an article to honestly share the 10 wins and 10 lessons I learned from running my first online course, in the hope that this helps another creator out there who is building theirs 🙂

By the way, you can now enroll for the second cohort of my course beginning in January 2022. 4 weeks. 40 students. 8 live classes. And a ton of fun! Come join 🙂


Things We Did Right a.k.a Wins

I worked with a small team of 3 others — Diya (Course Manager), Elan (Coach), and Kartik (Coach) — who were with me throughout the course, who went the extra mile in giving me their time and energy, and were really the biggest win for me. Thank you, the three of you. <3


Figure: Diya, Elan, Kartik, and I on a post-course celebration call <3


I am proud of what we were able to accomplish as a small team. We conducted many experiments throughout the course (and really, the course itself was an experiment of mine).

The following are the top 10 experiments that I would consider as a win.


1. Landing Page Copywriting



Your landing page can make or break your student enrollment.

Before writing the landing page for my course, I took a look at the other landing pages on Maven and noted down the elements I thought were unique in some of them. I also obtained feedback from Ryan Jennings, a coach from Maven who helped me throughout the process. In the end, I heard favorable feedback on the landing page and I attribute it to the following elements:

  • A catchy title and description: After many iterations, I finalized the title “Mindful planning for a mind like water 🌱” (which has since been changed as I changed my course’s name). It rolled off the tongue easily, evoked a sense of serenity in the minds of the viewer, and made them curious to learn more. In the description, I used the metaphor of a garden to explain the course’s goal, which gave the viewers a highly visual anchor point.
  • Clearly showing the ROI: With courses like mine which don’t have a direct monetary return but rather a huge time return, I still wanted to find a way to show the ROI. Hence, I added a Notion template (which has also been changed for the next cohort) that clearly displayed the investment versus return for a student.
  • Employer sponsorship template: Many employers have an education sponsorship program that let their employees enroll in courses for up to some $$. To enable potential students to make use of this program, I added an employer sponsorship template that will reduce the friction for them to request for sponsorship from their employer.
  • Adding emojis: If you’ve texted me a few times, you probably know my love for emojis. To me, emojis evoke a sense of playfulness and levity, so I sprinkled a few throughout the page! ⭐


2. One-on-One Calls With Potential Students

Diya and I experimented with many marketing techniques hoping that one (or more) of them will help us convert potential students.

We launched a promo video, set up office hours, engaged in email marketing, tried referral marketing with existing enrollees, and set up 15-minute Calendly calls for anyone who was interested to directly talk to me about the course.



Of all the marketing tactics, I observed that the 15-minute calls proved to be a worthy investment: Aside from converting ~20% of those I had calls with, I also got a chance to peer into the thought process of someone who was thinking of taking the course and understanding their hesitation.


3. Student Support via WhatsApp

This is an atypical idea that has worked very well in my case.

Before I launched my first book, Admitted, in August 2020, I had a few hundred people who wanted to preorder the book. To reach out to them on a personal level and let them preorder, I used WhatsApp since I knew everyone in my audience opened WhatsApp at least once a day. I didn’t want to rely on emails to share an important announcement. This turned out to be a brilliant medium for customer support. We were able to get very high open rates (70%+) and the buyers got a chance to chat directly with me (and my team), which increased their trust.

Hence, for my course, I purchased another virtual phone number through OpenPhone and used it to set up a WhatsApp instance on my work phone. Once set up, I gave access to my WhatsApp via web to my course manager and posted the number publicly everywhere I marketed the course. Instead of sending us an email, now interested students were able to directly reach out to me on WhatsApp and get quicker, personalized responses.

We continued using WhatsApp for student support even after the course began by checking in with those who enrolled once every week to ensure their requirements were satisfied.


4. Engagement During Live Classes

Wes Kao wrote an enlightening article on how to use the State Change Method while teaching to earn your students’ attention.

Wes says, “You are 50% instructor, 50% entertainer.”


We delivered engagement in our live classes through the following techniques (most of which were learned during the Maven accelerator program),

      • Breakout sessions: Putting students in smaller groups to facilitate deeper discussions on a topic. If you do this, ensure to give clear instructions before the breakout begins and have someone in your team join each breakout room and paste the instructions in the chatbox so the students are never unclear on what to do.
      • Guided brainstorms: Asking a question on screen and letting everyone think through the answer in silence. This was my favorite one as it introduced gaps of silence between classes and gave us all a chance to pause.
      • Hammering on the chatbox: Ask a lot of questions that end with, “Put your response in the chat box.” Even if the students don’t respond in the chatbox, they are still thinking about the question. And ensure to allocate enough time for their responses as you prepare for your live classes.
      • Picking student volunteers: I wish I’d done more of this: picking a student volunteer in every class to demonstrate a key concept being taught. I tried this for later lectures in my course and students appreciated it because the pace at which I would demonstrate something in Notion was too fast for them, compared to someone at their level.


5. Crash Course Within The Course

I organized a 3-hour “Crash Course” in the last week of my course targeted towards those who couldn’t attend many of the classes in the previous 3 weeks (more on this under the (1) under 10 lessons).

I distilled all the highlights from my 4-week course into these 3 hours to give them an opportunity to learn the important concepts without having to sit through 16+ hours’ worth of recordings. 12 students were invited to the crash course. 5 students made it to the class, and all walked away feeling great about catching up on the course despite missing many lectures.

Even if you find the perfect timing that works for everyone, some students will end up missing your lectures. You can delight them by organizing a crash course that delivers enough value for them to walk away happy



6. Post-Class Gatheround Sessions

Students join a cohort-based course to not just learn live from an instructor, but also from each other.

Create enough opportunities for them to interact with them each other. One of the ideas we tried involved Gatheround, an app that lets you easily create virtual “happy hours” with in-built prompts and a quirky interface.

We organized a gatheround session for 30-minutes after most classes to give students an opportunity to cool off with me and the others. This also gave me a chance to connect with them and learn about their lives.



7. Demo Day

Demo Day is an intentionally set aside period of time during the course when your students demo their hardwork over the past few weeks and learn from each other. We had two demo day sessions to cater to students in all of the 8 time zones.



At the end of each students’ demo, everyone else was asked to share (a) one aspect they really liked, (b) one idea/suggestion to improve on the demo, and (c) ask any questions they had. This was a win for all students since,

Everyone got to present their hard work and knowledge.

Everyone got to get feedback from at least 2 others on their work.

Everyone got introduced to a boatload of new ideas and frameworks from watching others’ demo (including me!).

I highly encourage all course creators to set aside at least a day or two for demos at the end of a course before graduation day.


8. Bringing In External Speakers

I had 6 external speakers in my course for in-class workshops, guest lectures, and Q&A sessions: David Allen (creator of GTD), Nir Eyal (author of Indistractable), Marian Knopp (founder of Workflow Wonder), Simo Elad (founder of Notion Automations), Rohini Duvvuri (Certified Coach), and Jafar Baig (Behavioral Scientist).

Think of running a course as running a Coachella for your topic: Bringing in speakers from such eclectic backgrounds and plugging them into the right part of the course will greatly enhance the overall learning experience for your students.


Video: The full one-hour interview with David Allen, the creator of GTD.


9. Uploading Recordings With Timestamps

You would be hard-pressed to find someone who enjoys watching recordings of a lecture in isolation.

One way you can help your students not lose motivation in watching class recordings is by adding timestamps for the various topics taught during the classes when you upload the recordings on YouTube or Vimeo (sadly, Zoom does not support timestamps today, which is a shame.)



You can reduce the effort on your end in adding timestamps by asking your course manager/coach to note down the times when you switched between topics during the class, to avoid having to watch the recording back to figure it out.


10. Building Feedback Channels

We were rigorous in taking in feedback during the course.

Following are the ways my team and I created space for ourselves to reflect and take in feedback from our students during the course:

Write down feedback after every class as a team: After every live class, guest lecture, and Q&A, we would keep aside at least 10 minutes to reflect on the past 2 hours and write down whatever came to mind on (a) what went well? (b) what can we do better next time? and (c) what are new ideas we can implement for next time? Your brain is not meant for remembering things. Given that my course centered around this theme, it was prudent that I practiced what I preached. And it paid off. By writing down feedback after every class and reflecting on ways to improve, we were able to, with time, make the classes more efficient, in terms of sticking to the time limit, allocating enough time for engagement, and having more hands-on exercises.



Collect end-of-week feedback from students: We created an Airtable form to get feedback at the end of each week. I wanted to measure if students in a flow state during the course, hence two of the questions I focused on asking were (a) how difficult did you find the concepts taught and projects given for the week and (b) how motivated are you to complete the course all the way. Over time, if we noticed that someone’s motivation dropped, we would check in with them individually and help out where we can. Or, if we found that most people find the concepts too difficult (or easy), we would make changes for the upcoming classes. The entire course was a series of recalibrations from one class to the next!



Observe student feedback across all channels: When you’re listening to someone talk, you’re not just hearing the words uttered. You’re also watching their faces traverse emotions, watching the movement of their hands and legs, and paying attention to the tone of their voice. Communication is equal parts verbal and non-verbal. Similarly, your students are not just giving feedback in a survey form. They are giving you feedback all the time. This comes in the form of engagement during classes, responses to posts in your community, and individual messages & emails.

The most overwhelming part of running a course for me was figuring out a way to listen to all this feedback and act on it.


Things We Will Do Better, a.k.a Lessons

I’ve been writing and publishing content for 8 years now. I’m very comfortable with putting out content and receiving static feedback in the form of comments and messages.

But running a live, cohort-based course was a whole other ball game.

Every day during the course, I would come to realizations on things I could have done better. Because we put in effort to listen to our students, we were getting more feedback than we could act on. But thanks to all that, now I get to act on it for the upcoming cohort of students.

Below are the top 10 lessons I learned from running my first course. I’m openly sharing this in the hopes that a creator out there reading this can turn these mistakes into lessons for themselves. 🙂

By the way, you can now apply for the second cohort of my course beginning in January 2022.


1. Setting The Day & Time For Classes

I conducted two live classes every week during the course: Tuesdays at 8 AM PST and Thursdays at 7 PM PST.

To come to this conclusion, however, was a big ordeal.



My students were spread across 10 countries and 8 time zones. While this was a wonderful thing to witness, it made it extremely hard to find a time that worked for all. We sent out a form asking everyone’s feedback on the days and times they prefer…. and it turned out to be an insanely complex optimization problem. We could not find any time that worked for even 80% of the students. So we ended up picking two different times since the western side of the world preferred 7 PM PST and the eastern side preferred 8 AM PST. This resulted in many students being able to attend only half of the classes.

Lesson learned: Set the days and times for the classes before launching the course, thus ensuring only those who can make it end up enrolling and those who cannot make it but still enroll don’t feel blindsided.


2. Building A Learning Management System (LMS)

I took a unique route in building my LMS: it was built entirely on Notion.

Learning Management System is a software application used for the administration, documentation, tracking, reporting, and delivery of educational content. Coursera is an LMS system specifically tailored towards MOOC courses. For the students watching videos on Coursera, it acts as the hub where they can find all the videos, assignments, and interact with the community of learners. For the teachers creating videos on Coursera, it acts as the hub where they can host the videos, assignments, and track the progress of the students, and engage with them.

For my course, my coach Elan and I built a type of LMS entirely on Notion.

Our rationale behind doing this was to reduce friction for our students in using Notion and give them a single platform to access all the resources and work on their projects (which essentially was to build an end-to-end robust planning workflow on Notion.)

We used the virtue of synced blocks (which is one of the Notion’s newest game-changing features), linked databases, views, sorts, and filters to create the LMS. Below are a few screenshots to show you what we built.



To this day, I marvel at what we were able to accomplish within Notion.

But, this turned out to be a lesson and not a win since we discovered that many students found this to be overwhelming, especially those using Notion for the first time. What caused more overwhelming is the fact that we didn’t have 1-on-1 onboarding before the course began to get them acquainted with the tool.

Reflecting on it, I feel that I asked my students too much too soon.

For my upcoming cohort, I am using the LMS provided by Maven.

Lesson learned: Build the LMS in such a way that it reduces cognitive load for the students and makes it incredibly simple to find the resources they need. Also, conduct 1-on-1 onboarding before the course begins to help them get used to the tool.


3. Streamlining Communication

If there is one area where there has been too much innovation, it’s communication. Today, over 3 billion people around the world use some form of communication app.

And chances are, you have more than one on your phone. Or even six.



For my course, we communicated with the students via email, Slack, WhatsApp, and other indirect mediums (calendar invites, Notion comments, etc.) for various purposes.

At least one student gave feedback that communication came from too many different streams. And another mentioned that the calendar invites could have been sent in advance. Although we used various mediums to ensure students stay on track and keep making progress, I feel this can be improved while reaching the goal.

  • Lesson learned: Moving forward, I am making this more streamlined such that each medium is used for specific purposes, and the student does not feel overwhelmed.
  • Email: Only for the beginning of week announcements specifying what they can expect in the week ahead.
  • Community: Last time, we built our community on Slack. This time, I’m moving ahead with Circle, which seems more effective in sparking engagement given its Newsfeed-like interface and modern UI. The community is where all interaction outside classes will happen, including during-the-week announcements.
  • WhatsApp: Only use if a student is unresponsive in attending classes and on the community for more than 7 days to check-in and ensure they get back on track.
  • Calendar invites: Send invites before the course begins for all classes, mastermind sessions, and guest lectures. As a side note: send silent invites such that the students don’t receive an individual email for each of the invites.


4. Building Effective Onboarding

The curse of knowledge is very real when it comes to onboarding.

Having used Notion for ~2.5 years now, the tool is second nature to me. As it was for my coaches. So when it came to onboarding our students into the tool, some of whom were using it for the first time, and into the LMS we built on top of it (refer to (2) above), we were blinded by the curse of knowledge.

The same applies to any tool you expose your students to: Slack, Circle, Maven, or any LMS/community platform. While you might have been using them for weeks and months, they’re probably seeing it for the first time.

Without an effective onboarding process, your students will not stick to using your tools, leading to waning motivation and other downstream effects in the course. For example,

Pooja doesn’t know how to use Circle –> Pooja stops using Circle as she thinks it’s not important to the course –> Pooja loses out on all the serendipitous interactions and mini-announcements

Lesson learned: Ensure every student gets a 1-on-1 or small group onboarding session by a coach where they’re (a) taught the purpose of the tool, and (b) asked to open the tool and use it for something specific.


5. Weekly Mastermind Sessions

The whole is greater than the sum of its parts. — Aristotle

mastermind group is a peer-to-peer mentorship group used to help members solve their problems with input and advice from the other group members. The concept was coined in 1925 by the author Napoleon Hill in his book The Law of Success.

Everyone who joins your course comes with a bundle of knowledge waiting to be unlocked.

How you unlock it makes all the difference.


Figure: A screenshot from a silent brainstorm session during one of the classes


In my first cohort, it wasn’t until the second week that we created “pods” amongst the students with each pod containing 6-7 students from similar time zones and backgrounds.

Although we set up weekly mastermind sessions for all pods, it did not take off the way we wanted; probably because it was introduced too late and students felt it was not a necessary part of the course. Only ~20% of the students participated. Now, reflecting back, I realize this should have been a key part of the course from the beginning to give students a chance to learn from each other.

Another idea I wish I had implemented was to create “accountability partners” by pairing students one-on-one to keep each other accountable.

Lesson Learned: Divide students into “pods”, set up weekly mastermind sessions from the beginning with a well-thought-out playbook, and create accountability partners.



6. Purchase Power Parity For Pricing

Purchase Power Parity: PPP is a metric used by macroeconomic analysts that compare different countries’ currencies through a “basket of goods” approach. For e.g., a common item used to compare the standard of living across various countries is the amount it costs to buy a McDonald’s Big Mac. It costs $5 in the U.S. and $2.4 in India.

So if you’re catering to people from more than one country and more than one standard of living, it’s important that you take the PPP into account.

Parity Bar is a website that lets you create coupon codes based on the country from which someone purchases your course. You can set the discounts you want for the various countries, thus giving everyone on the internet a fair chance to take your course.



My course price for the first cohort was $500, irrespective of where people joined from. In the end though, I did end up giving discounts for many students in the end: early supporters, those who were financially constrained, and those from India who didn’t have the same purchase power parity.

However, this process could have been made more streamlined with a tool like Parity Bar.

Lesson Learned: Give everyone a fair chance to join the course and make your job simpler by using a tool like Parity Bar to give discounts.


7. Ordering Welcome & Graduation Gifts

After ideating for a while, we decided to send the following as welcome gifts to each of our students: a copy of the book Getting Things Done, scented candles, and a laptop stand (because ergonomics is important!)


Photo by Ekaterina Shevchenko on Unsplash


Since our students were in 8 countries across 4 continents, ensuring these gifts actually reach the students took us a monumental logistical effort.

We ran into so many nuances issues while ordering, such as: being unable to order more than 1 quantity of certain items on Amazon; being unable to send a Kindle book as a gift specifically in certain EU countries; and being unable to order physical gifts in non-U.S. and non-Indian countries. We looked at many international shipping options, but none were under our budget. In the end, we ended up spending a great amount of time customizing gifts and ensuring everyone got it before the course ended.

For the upcoming cohort, I plan to alleviate this problem by (a) restricting students to only a few countries, and (b) prioritizing digital over physical gifts (still TBD).

Lesson Learned: Delighting your students with physical gifts makes sense if your cohort is from a single country where it’s possible to order multiple quantities of the item. Otherwise, it will become a big, logistical time sink. You can spend this time elsewhere in the course.


8. Having A Targeted Audience

The ages for students in my course ranged all the way from 17 to 55, with most falling in the 25-35 range.

The background ranged from undergrad students to full-time employees to entrepreneurs to consultants.

And, as mentioned earlier, they came from 8 countries and 10 timezones.



The beauty of learning in the 21st century is that your peer group clearly does not have to be constrained by space, time, age, or background.

However, upon reflection, I realized that too much heterogeneity, especially in terms of timezone, will lead to students who cannot fully engage with each other. Also, the problems faced by someone who is a student were very different from someone who was an entrepreneur.

Moving ahead, I’m keeping a more targeted audience for my upcoming cohort: full-time knowledge workers in the U.S. who want to work on passion projects, and have not been successful so far in finding a tool and system that will give them control of their time and live a balanced life. If that sounds like you, consider applying for the upcoming cohort. 🙂

Lesson Learned: Too much heterogeneity in the audience can lead to students who cannot resonate and engage with each other on the problems they face. In the earlier cohorts, focus on reaching out to a targeted audience group.


9. Keeping Theory Out of Classes

The education system I grew up with failed me in many ways. My classes were mostly filled with insipid professors presenting PowerPoint filled with jargon and solving problems on a blackboard as if they were teaching theory, with no involvement from the students. There were no brainstorming sessions or exciting discussions among the students.

The flipped classroom model is one form of panacea to this systemic problem: it’s an instructional strategy that aims to increase student engagement by having them complete necessary readings outside the class and focus on problem-solving inside the class.

Although I tried to use 50%+ of live class time to have breakout sessions and hands-on activities, I could have tipped the scale even more.

Moving ahead, I plan to implement the following in my upcoming cohort,

  • Pre-record videos on key topics: Instead of squeezing everything into the live classes, I plan to pre-record videos on key topics such that students come to class after watching these, prepared to engage in productive discussions!
  • Only share reading materials that are relevant: While Elan and I carefully curated the articles & videos we recommended, it was a lot and not fully necessary in reaching the primary aim of the course: building a second brain planning workflow in Notion. Upon reflection, I also realize I could have published a few articles on the topics taught in the course myself, rather than find articles that kind of come close.
  • Use live class purely for discussions & demos: I plan to begin every live class with a demo from a student volunteer, doing a brief review of the pre-class reading and the workflow they’ve built so far. Followed by this, I hope to divide the class time to cover 2-3 major topics and have discussions and hands-on activity sessions around each of them.
  • Mastermind sessions: As mentioned under (5), every class will be followed by a mastermind session the next day for students to work on projects and help each other solve problems.
  • Lesson Learned: Follow the flipped classroom model and keep theory mostly out of classes (in the form of short video tutorials and reading materials) while using the live class time for brainstorming, discussions, and hands-on activities.


10. Giving Time For Yourself

We come to the hardest lesson of all: taking care of yourself while taking care of your students.


          Figure: A picture from one of the brainstorming/whiteboarding sessions I had in building the course.


If you’re a first-time course creator, it’s extremely hard to draw a boundary and tell yourself, Okay, I’ve done enough for now. I need to pause and start again tomorrow. I deserve to go rest.

You’re constantly thinking about your students, team, and honestly, your reputation.

What if I mess up in a live class? What if a student feels they’re not getting the value? Will my team stick with me throughout?

Asking these questions makes you a good course creator who cares. So never feel that this is wrong or unnecessary.

At the same time, taking care of yourself is important. I’ll say that again: taking care of yourself is important. You deserve the care you’re giving to everyone else. And you deserve to not feel burnt out or exhausted.

This is a lesson I am still learning, and hope to continue learning along with you.

Excited to be a part of my upcoming cohort with all of these changes? Come join it before January 10th, 2022 when applications close.


Closing Thoughts

This article was a way for me to openly celebrate my wins and honestly share the mistakes (turned lessons) so that you can stand atop my experience as you build your course. It is also a way for me to make a promise to the students of my future cohorts that I will learn from my experience to make theirs better.

Mistakes are bound to happen when you’re a first-time anything. What you do after with those mistakes makes all the difference.

Do you turn them into lessons or let them disappear in the couch cushions of yesterday?

I’m choosing the former. What about you? 🙂


Figure: Some gratitude sharing at the end of the course. <3