Going From Teaching 15 People To 750 People - Part 1 (Humble Beginnings)

Imagine this, but digital

Intro & Context

For those of you who don’t know, my friend Rahul Pandey and I have been growing a completely free Tech Career Growth Community over the past ~5 months. Our goal is to take the vast learnings we have accumulated across our combined ~15 years in the Silicon Valley, polish them into an easily digestible format, and give it all away for free. The main way we do this is by hosting bi-weekly-ish live sessions where we break down a complex, important tech topic for anyone who wants to come. After going through some prepared content for ~1 hour, we then take as many questions as we can, often for ~2 hours, leading to a staggering ~3 hours of us talking per session. The experience is open, honest, and interactive; Rahul and I feel like we’re truly connecting with the community during these sessions, which is why we love doing them.

While the sessions are hugely successful now, the path was far from entirely smooth. Rahul and I have learned a lot along the way, and we have constantly been evolving the session format over time to make it more effective. Since we have been doing this for a while, I felt like it was a good time to look back and break down this evolution process. It’s always fun to capture a little piece of history, and it’s important to formally write down and share key learnings as well. There’s a lot to unpack here, so I am splitting this into a 4-part article series, each one covering a “phase” of our session growth:

1. Humble Beginnings (15–30 attendees)
2. Hitting Our Stride (30–75 attendees)
3. Breakthrough (100–200 attendees)
4. Present (400–750 attendees)

With all this context out of the way, let’s jump straight into Part 1, “Humble Beginnings”.

Guiding Philosophies

With the exception of our very first session, the first ~6 sessions we did were within this 15–30 people range. Our first session had around ~50 attendees, but we ended up learning that this was due to novelty effect (launches are fun!) and a lot of our friends joining us purely to show support. Anyways, this was our approach going into the sessions:

1. We wanted it to feel more like a conversation - The vast majority of content is unidirectional. The creator produces some content where they talk, and you consume it. In simpler terms, the relationship is purely creator -> consumer. We saw a gap here, and our strategy was to fill it by creating a bidirectional relationship (i.e. creator <-> consumer). Yes, we still talk to you, but we want you to talk with us as well.
2. We wanted it to be more informal - It is hard to have a smooth, natural conversation if one of the parties feels too rigid or polished. Even though we would mainly be talking with complete strangers over the internet, we wanted the experience to be as close to a “regular” conversation as possible, something akin to what would naturally happen when you’re mingling at a tech conference or hackathon.
3. We wanted to focus on the content - Of course, we didn’t want to just have some casual chit-chat that doesn’t produce results. We went into this wanting to help people, so we had to tread a fine line between having a more casual vibe while simultaneously delivering concrete insights and advice that attendees could apply to their careers, improving them in the short to mid-term (1–3 months).

Call Format

With all these guiding philosophies in mind, this is the format we ended up with initially:

1. The call would be held over Zoom.
2. The call would be audio only. We wouldn’t have our video on, and we explicitly prevented our attendees from turning on theirs.
3. Attendees are muted by default and can’t unmute unless we give them permission. Attendees should use the “Raise hand” feature when they want to chime in with something or ask a question.
4. We wouldn’t have anything close to a full script. For the first session, we wrote down some key points and even did a dry run, but for the most part after that session, we dropped the dry-run part and went into the sessions with just a content skeleton. When it came to what we actually said, 80%+ of it was free-styled.
5. We would go through our “prepared” content initially (just going through the skeleton and expanding on each point) and then open the floor for Q&A. However, we wanted to avoid just “talking into a void” for an entire hour, so we would regularly pause in between core points (so every 5–10 minutes) to take questions. The idea was to have this bidirectional communication I talked about before.
6. We would have a guest speaker in almost every session. The idea was to get as many perspectives as possible, and the format of inviting outside folks to your talk and having a casual conversation with them is a powerful one, with several podcasts seeing massive success with it.

Evolution

For the most part, this format worked and a lot of the guesses we made initially have carried over to this day. However, there were some things that we quickly learned and had to make changes accordingly for:

1. Needing permission to talk is awkward at this size - At that point, the group is quite small and intimate, especially when it’s just 15 people, so the vibe was very stilted when you had such a high barrier to contributing to the conversation. We addressed this by allowing people to unmute and chime in whenever, but still having everyone come in muted by default (you never know when someone will have background noise).
2. It’s hard to build a personal connection with guest speakers - Our goal is to do this at scale, but we still want as many folks in our community as possible (ideally, all of them) to feel connected with us. The problem with having guest speakers is that you obviously want to give them time to talk - Why else would you have them come on? However, if someone who isn’t you is the dominant speaker, it is hard for the audience to feel connected with you. Every second we weren’t talking was a second where we could have been telling a cool story, cracking a joke, or just hanging out with our community instead. Also, having a guest speaker made things harder logistically, both on the planning front and during the session as we would have to build up conversational chemistry on the fly. Rahul and I have built up great synergy doing so many of these sessions together, and it just makes sense to continue leveraging this as a powerful asset. Anyways, after the first few sessions, we stopped doing guest speakers and we haven’t looked back.

Retrospective

Looking back, I’m happy to say that we started off with a really strong core. We wanted the spirit of these sessions to be about connection: Rahul and I didn’t want to just be 2 guys rambling at you in some clickbait-ey, overly polished YouTube video. We wanted to be raw, open, and honest from Day 1, and we wanted to talk with people instead of at people. A lot has happened since we started giving these sessions in mid-January, but 1 thing that’s been consistent is the feedback reflecting this intended spirit: It has been incredible and often heart-warming; we can tell from the very kind words that many folks in our community feel a genuine connection with us. This has shown in the mechanics of the session as well: We have added a lot of bells and whistles, but the format is largely the same. The sessions are still primarily audio-only, we have a content portion and a Q&A portion, and the vast majority of the content is unscripted.

Anyways, that does it for Part 1. As always, I hope you learned something from this or at least found it interesting, and feedback is appreciated. If you want to know exactly when future parts of the series drop, follow me here on Medium. Until next time!