the cohort fuck ups

...and what every creator needs to know

In partnership with

DISCLAIMER: Before you read the first line with skepticism, let me clear this is not a promotion. I will not ask you to buy anything from me - This edition is only a case study and probably a playbook for those who want to run their cohort.

I launched the Dopeletters cohort five months ago.

In 10 seconds, the cohort’s overview:

  • Help creators start and scale their newsletters from 0 → 500 subscribers

  • Exclusive for not more than 15 members per batch

  • Stretched over six weeks

  • Forever free access to the Dopeletters community

I hosted two batches Between February and June, educating 14 members about the newsletter space and how they can produce the best results as creators.

I have learned many things running a cohort and managing a community in 2024 - and I believe it’s time to implement the learnings to upgrade the cohort.

I mentioned all the steps we have taken so far and how we plan to improve in three parts:

  1. How it all started?

  2. The Hurdles

  3. Plans for the future

We will get into the details in a second; let’s welcome our sponsors first - don’t forget to click on the link and check out Gamma!:

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Part 1: How it all started

1/ Structure

All I had were some important topics to discuss. The thoughts were scattered; so I began by bringing some order to the chaos.

Along with the topics, I focused on what kind of cohort I wanted to build - and I was crystal clear about three things:

  • It shouldn’t be a three-hour workshop or something similar. While the theory is important, I wanted to include myself in the real work of the creators and do all I could to support them.

  • Hyper-personalization is non-negotiable. Each creator, their content and audience is different. Instead of one strategy for all, I wanted to spend more one-on-one time. That’s why we’ve limited the cohort to 15 members per batch.

  • Independence. Once the cohort is done, the creators should be operating their newsletters independently without major changes to their routine.

Keeping these priorities in mind, I came up with a six-week structure that focuses on learning, execution, community, and one-on-one time.

We have even differently approached the members who start from scratch vs the ones who were already running their newsletters; so the latter ones don’t waste their time on tasks they’ve already finished (like landing page, set up, welcome email, etc.)

2/ Pricing

Once I had a skeleton of the structure, I spoke to multiple creators interested in building their newsletters. I explained to them the structure, my credibility, and my commitment (time and otherwise) to the cohort.

Having multiple conversations helped me understand how valuable they think the cohort’s promise is.

It made me realize I have been underestimating the value. I planned on pricing the cohort at ₹2000, but my interactions suggested otherwise.

I took an average and priced the cohort at ₹5000 - and was pleasantly surprised with how everyone was okay with it (a good sign for me to stop underestimating myself.)

3/ Tech Stack

I focussed on the basic things we need to get started. My goal was to keep it minimal, cost-effective, and avoid any unnecessary tech. The result:

  • Recordings and sessions: Gmeet

  • Communication: Email; used Beehiiv’s Segmentation

  • Community: Discord and WhatsApp

  • Notes: Notion

As simple as that.

4/ Selection Criteria

The cohort was not for everyone. I believe there are some basics one needs to master before they get onto newsletters.

Three of our major filters included:

  • Writing: Irrespective of what you do or what your newsletter is about, you have a long way to go if writing isn’t your strong suit.

  • Social Captial: If you don’t have social capital (followers, being active in communities, offline networks, etc.), gaining subscribers becomes difficult, and operating a newsletter only becomes a burden.

  • Leverage: “What do you specialize in?” is a big factor I look for. For example, I have seen many creators create newsletters for founders. The bigger question is, why would a founder read your newsletter? Are you a founder yourself? Have you worked closely with startups? Do you have insane research and curation skills? What makes you worthy of a founder’s time?

Some sound a little harsh. Some might make sense. But I decided to move forward with what I felt was right.

We had 41 applicants and selected only 14 because we didn’t want to ask for money from anyone we thought we wouldn’t be able to help.

5/ Promotions

I hardly promoted the cohort on social media. This is because the cohort’s pricing is high-end and one wouldn’t register as easily as they would for a ₹499 live, three-hour workshop.

I realized the conversions need authority and trust, so I only promoted the cohort to Cognition readers who more or less have spent a decent time reading my work.

Part 2: The Hurdles

1/ Structure had its downsides

The structure was designed for consistency and longevity. But two batches made me realize I should work more on immediate results. While long-term methods are not easily noticeable but crucial, short-term results are equally important for creators to see progress for themselves.

My focus points will also include short-term dopamine hits, so it encourages creators to do more and stay excited about their projects.

2/ Lectures vs Interactions

I taught for nine months at My Captain. All mentees were beginners, so the lecture model worked fine. I shared all the techniques in detail for hours - and mentees were happy to listen.

But with our screening process, we are now only picking people who have spent at least a year writing online or creating content. Their basics are strong, and all information need not be spoonfed.

I realized I have been more elaborative than I should have. When asked for feedback, Chelsi suggested me to send pre-reads before each session. This will cover all the basic points and I only need to elaborate on more crucial topics with specific case studies.

I have experimented with pre-reads, and it seems to be a good start towards more interactive sessions. Getting members involved in more ways than only listening will be a priority.

3/ Gamification of tasks

I give a long list of tasks each week and I still believe all of them are crucial. But the biggest hurdle with these tasks is they sound like a school assignment - and that always creates friction.

Honestly, I don’t know how, but I will figure out a way where ‘action’ is more fun than thinking about action.

4/ Not everyone works on their newsletter

Creators sign up with enthusiasm, but life happens, and they can’t make it a priority. Most of our creators work full-time, have gigs, are students, etc., and we don’t blame them for not making time for newsletters.

But personally, I don’t feel okay charging people money and then seeing them not utilize the value for money. One might argue it is not my fault but I am not okay with it, and I keep following up with them even if it sounds a little creepy.

Not all things are in our control, but I will be more conscious about making creators prioritize their enthusiasm.

Part 3: Plans for the future

1/ Work on results first

8-10 creators from Dopeletters are actively running their newsletters and I want to help them get significant results before I start a new batch. I gave myself two months; let’s see where this goes.

2/ Paid community

Dopeletters community will always be free for the cohort members, but I will also open doors for 50 paid community members. It will be a three-month membership, and we will have new openings only when folks from these 50 choose to discontinue.

Community Strength = 50 Paid Newsletter Creators + Dopeletters Members

3/ Fast shipping

I understand the importance of a 6-week cohort, but the two batches also made me realize the value of speed. As much as I’d love to focus on sustainability, we love shipping fast as creators.

Instead of six weeks, we are planning to compress the cohort to a month without losing any value and efficiency.

I don’t know how the idea of running a cohort sounds to you. It is exciting and comes with its own set of challenges, and I tried to mention all the major problems I faced in the best way possible. I hope this is of value.

Before we sign off, I want to introduce you to the newsletters we are helping grow. The creators are doing their best, and we are guiding them with our minor contributions.

Ready for awesomeness?

  1. Aditi writes micro-essays on how she wears multiple hats while still being a student

  2. Chelsi dives into fun rabbit holes and gives you answers to why things are the way they are

  3. Anirban runs an email copywriting newsletter, mostly focusing on making money with emails

  4. Gaurav talks about all things Cricket. If you love this sport, you might find Gaurav’s thoughts relatable as he writes from a fan’s POV

  5. Jerry curates his decade-old experience in marketing and ensures you crack the ABCs of personal branding

  6. Pranav shares his stories of working with startups and curates insightful and rare resources

PS: Some creators have just finished batch two, so you might find less than five issues in the archive. This doesn’t mean they are inactive.

That’s all I have on running cohorts.

See ya soon! 🫡