Monthly Archives: October 2020

How Build a Highly-Engaged Community with Slack

Hey yenizens!

This breakdown / deep-dive is a long one, so, let’s just jump to it!

To infinity & community,

— john


Continuing in our breakdown series is a conversation and presentation by Jacob Peters, cofounder of Commsor, on how to build a “highly engaged” community via Slack, with Tom Osman of Makerpad!

As always, I extract the best tips, tactics, and practices from this hour+ long session in a bulleted, digestible format — enjoy!

Oh, and as Jacob mentions earlier in the program, many of these tips, tricks, and practices are equally applicable and usable for other platforms, not exclusively Slack!


Tip #1: That Profile Though

Members who fill out their profile within the first week are three times more likely to engage over the lifetime of their time in the community than those who do not. This “sets the tone” for the community and is something that should be encouraged.


Tip #2: Think Math (The Exponential Kind)

I love how Jacob attacks community building from a distinctly mathematical perspective, taking the example of twitter or a newsletter and how that fosters 1-to-1 connections (say for instance, 500 followers to your 1 account) while having a system like slack with 500 members which would allow many-to-many connections resulting in an exponential increase of opportunity.

This is not just simply clever thinking; it really does impact tool choice and how you build a community (and business using community).


Tip #3: It’s How You Use It

Jacob answers the question of whether Slack is the “right” tool for your community building needs by saying:

It’s not about the community tool; it’s how you use it.

Using a tool that is both familiar and that is currently part of a user’s existing workflow is a powerful driver for (ease) of adoption, use, and engagement — they don’t have to learn anything new.

Jacob posits another possibly-contentious perspective by stating that the natural limitations of Slack are offset by the “power of familiarity” of the tool itself and that’s why he still chooses Slack over purpose-built platforms.

By extension, this is also why we (still) have Facebook Groups and why FBGs are still very much a part of the community building landscape. And that landscape is fast-growing:

Yikes. But, it’s how you use it and Jacob continues to remind the audience how critical he believes it to be for community builders to “match the rhythm / cadence” of your audience so that they can engage without friction.

There’s just not a “one size fits all” solution out there; it’s vastly better to execute well with an existing tool than attempt to find the perfect one.

And you don’t need the “newest” and “coolest” technology either! As long as there’s solid connections, old forum (software) communities will continue to grow and thrive:

There’s a lot of wisdom there.


Tip #4: Take the Long View, Slack as a Foundation

Jacob lays it out concisely when he states that upon the decision to move forward with Slack, you should consider a 2-3 year view, using it as a great place to build a strong foundation, but not a “be all, end all” solution.

He shares the example of the Product Marketing Alliance community that started on Slack with just a handful of members and then 18-months later is sporting a “full stack community” with courses, education, podcasts, events, and much, much more:

What I love is how quickly a small implementation of Slack could become a fully-scaled business — with no obvious ceiling in sight! The raw potential of taking a small community to $million dollar revenue business is not fantasy nor fiction; it’s scary-real.

Tip #5: The Power of Content Curation (to Attract New Members for a New Community)

A question via the live audience asked what tactics Jacob has seen to be proven successful for attracting new community members to a community and he states one of his go-tos plainly:

Growth is certainly one of the most challenging things — it’s not enough to have a shared reason for people to gather, you have to be proactive about the ways in which you promote these things.

One of the best strategies that I’ve seen work well, especially when building a community around a niche topic or industry, is to start with your audience and become a content curator.

There is so much content and noise out there — you can create value by curating content and slicing through the noise.

Jacob did this for Commsor as well, his current startup, and built a newsletter that curated the content around the space and then invited subscribers to join a many-to-many experience, which ended up being Slack:

Note: I am a member of The Community Club and give it 👍🏻👍🏻.


Tip #6: Keeping a Well-Run Slack is a Good Slack

Jacob gives four tips:

  • Lock Slack app installs, @channel, @here, invitation and ability to create channels to admin only
  • Channel default #general to #announcements and lock posting permissions
  • Hide user email addresses on public Slack profiles
  • Name channels carefully, set clear topics/descriptions, and don’t create too many!

Tip #7: Onboarding Matters

Jacob shares a few useful tips using bots (Greetbot) as well as a custom Zapier integration that can help onboard new members quickly that can create custom “Welcome Notices” and more.

Now, community leaders can create a direct connection with new members auto-magically using Slack’s Workflow Builder.

Rounding out the advice is something as simple as a personalized “Welcome Video” using a tool like Loom:

As well as a quick-tip on making sure folks get connected to the community via their mobile device (mobile app) as well as desktop app (Windows / macOS), a far better way than just via the web.


Tip #8: How to Start Engagement

One of the best ways to lay the foundation for quality engagement is creating “starter threads” or conversations in Slack:

At a meta-level, making sure to never forget that you should use techniques that maximize many-to-many connections which also helps scale the community team:

Creating a system for moderators of certain channels / volunteer community leaders is also a worthwhile consideration. Building a separate channel, for instance, for them to communicate, share the issues that the community is facing, and provide a safe place for support is vital.


Tip #9: Keeping the Engagement Alive

One of the best ways to keep engagement high is by creating a content schedule, using a simple spreadsheet or a tool like AirTable. This has the added benefit of creating community “traditions” that can help strengthen a new and younger community.

And, as Jacob mentions, they can be as simple (like above) or as complex as you want and/or need them to be:


Tip #10: Weekly Summaries

Something as simple as a “Weekly Summary” of what happened and what the community might be looking forward to in the coming future is easy using Slack’s native “notes”:

There are a few bots that can help do this but Jacob suggests manually curating them in the beginning (with advanced workflows possible as well).


Tip #11: Customize the Look-and-Feel

You can easily change the look to be on-brand or as funky as you’d like through Slack’s built-in settings:

Spending a little time on this can make the community feel a bit more personal and homey.


Tips Galore: The Home Stretch

Jacob shares a few great tips as he rounds out his time on the Makerpad interview, fielding live member questions:

  1. How to get around Slack’s history (10k posts) limitation? Use a free Notion document to capture the best conversations every week to create a searchable database.
  2. Slack Apps that you love? Zapier is one of Jacob’s favorites.
  3. How to map the journey of a user? Start with a simple diagram of how you want the user to experience your product, service, and community. You don’t have to use expensive tools.
  4. Jacob highlights the importance of a convincing and nicely-designed landing page for the community that clearly states intent and value.

Oh, and don’t forget:

Have a good one folks.

Steph Smith on Building Community Through Content

Hey yenizens!

I’ve got a growing backlog of content that I’ve been meaning to get through and so let’s just jump right into today’s issue!

But, before I go… let me know if you’d like to connect with a fellow yenizen for some bespoke, hand-selected matching! Just reply to the email.

To infinity & community,

— john


As I’ve done in my previous deep-dives, I’m tackling a lot of the great content that the Makerpad team is developing and breaking them down into more bite-sized, usable pieces, especially with Q&A-type workshops like the one with Steph Smith of Hustle & Trends.

The goal is to capture the best and most useful pieces of insight as well as to pull-out the actual questions and answers in bulleted-format for easy review.

Let’s go!


So, who’s Steph Smith?

Steph leads operations for the Hustle, a newsletter read by over 1 million people a day, and Trends, the premium research arm and private community associated with the Hustle. The Trends community is a 7,000+ (and growing) Facebook group.

It’s worth reminding folks, as Steph does, that this now-big business started out as a simple email newsletter.

And, it’s also worth noting that Steph (and the Hustle Team) felt like there was a definite “ceiling” to the size and scale of a newsletter, especially regarding monetization and business modeling.

This is something worth thinking about as some of us venture farther into the depths that is newsletter communities. Consequently, they built out a “premium” newsletter (“Trends”) which Steph also runs and it now has “a few thousand” subscribers and is growing strong.

It makes you wonder if multiple newsletters is an inevitable consequence of successful growth or whether it’s more related to financial modeling or something else in that frame (if you know, lmk!).

Moving from Content to Community

It’s hard to jump-start a brand new community, so, they focused on creating something that was easily shareable: Content.

This is still a big part of their strategy as folks will come for a particular piece of content but they will stay for the community once they get involved.

It’s difficult to showcase the “value” of a community — much easier to describe something of obvious (and clear) value.

Come for the content, stay for the community is a well-worn strategy.

“Good” Engagement Requires Intention

Something that Steph repeats many times is the focus on modeling and providing examples of what a “good” community member does — everyone on the team does this, especially the senior leaders.

One easy tactic is to simply call out folks who are showcasing the community values and doing positive things.

How Steph Launches a New Product

As you’re beginning to “move” people from one community into a new one, you have to know what the “perceived value” is and how to properly represent that well.

Direct conversion landing pages do not do well, in general, so it’s important to foster the new community by identifying new members and/or finding a working distribution channel that solves the right problem for the users (e.g. content via email newsletter).

Consider what they’re getting (and not getting) from their existing community and what information or tool they need. This will increase the likelihood of conversion and gaining traction.

Is Facebook a Good Place to Build Community?

Speaking just from the perspective of a tool, it’s just one of the best, despite views on the company itself. Questions that Steph considers:

  1. How big is this community going to get? If it’s small, Whatsapp or Telegram work. But, more than 100, that’ll break down.
  2. How likely are the community members going to engage? Sometimes, proximity (being logged into Facebook) is the reason that they engage, but, they wouldn’t have otherwise done so independently.
  3. What percentage of your audience has those applications already?

Focus on your audience, always.

How Does Email Build a Community?

When they started, they leveraged content via the email much more because no one else was creating posts. Now, moderation is a broader problem now that we’ve reached scale.

But, to start, posting content will be required from the early team and you’ll have to do it for a while to really jump-start the community around content.

Bottom-line: Create content worthy of attention. Create a space for it and then invite folks to use it and check it out.

Thoughts on Monetizing Email Newsletters

It’s really neat to hear Steph talk through email business models. Unlike Morning Brew, who decided to verticalize their newsletter, Steph and the team decided to do a more “classic” marketing funnel where there’s a big funnel at the top, monetized through advertising, and then below, Trends, a backend product for more in-depth guides and video on specific topics.

They built this because they listened to their readers and audience and what was missing is how to execute against the many ideas that Trends was giving them (i.e. valuable content) and now they are building “guides” that will help folks take those ideas all the way into production.

A really fantastic look at how they not only think through product development and design but also how they deploy them publicly.

Tactically, What Tools Does Steph Use?

Facebook makes it crazy-difficult to automate anything so that’s one of the major downsides to using Facebook for community. So, that’s a big part of Steph’s workflow and daily exercises.

Unlike many large communities, they don’t have structured days like other communities (e.g. Monday activities, Tuesday activities, etc.). They try to listen to the behaviors of their community and try to be like them.

Also, as a company and business, they are at the point where they are starting to build out more specific roles and responsibilities — in the beginning, everyone was posting all the time but now they are looking to hire for more specific roles enabling folks to not just be part of the community but also having to moderate and lead.

This is a critical juncture for Steph and the team — I wish them the best!

What is the Tech Stack for Trends?

They first started with Mailchimp because it was very easy to use (basic HTML templating and themes) but as they scaled they moved to Active Campaign that had more customizations available to them.

Now, they are moving to SailThru — but it’s worth noting that this is for a newsletter that has 1,000,000+ subscribers! So, it’s not something for newer or smaller newsletters.

Bonus: Steph uses Mailchimp for her own personal newsletter as well and she’s actively thinking about where she’s going to take her community next. Using something like a MightyNetworks or a Circle is possible, but, until she thinks through how big she wants this to get, she’s sticking with Telegram.

How Steph Manages Ideas and Execution

Steph first thinks about her goals and how she works, aligning the projects around her existing skills. She tries to tackle projects that she knows she can complete, end-to-end, in a very specific amount of time.

The level of self-awareness here needs to be appreciated as well because to be able to accurately estimate a project’s time-to-completion means that you’re only tackling things that you know you have the current skills to do.

Word up.

She uses her recent ebook launch as an example, she knew that she could finish that in two months and so that’s what she did.

Also, she has some amazing advice on developing projects and one’s career: She suggest to focus on something that you’re already doing naturally that no one has asked you to do — these are things that wouldn’t be as much of an “uphill battle” because you wouldn’t be fighting yourself on a consistent basis.

This might be a good place to start with what you enjoy naturally. Focus on your habits, your own behavior.

How Do You Get Other Folks To Talk About Your Project?

You have to first make sure that your users are getting extreme value. People only talk about the absolute best stuff.

And in terms of community, you have to be honest with yourself: Are you building the absolute best community? Or, are you just average.

Understand what your real edge is and what that is in a real concrete way. If you can build that, people will talk about it.


Finally, a few links mentioned throughout the entire show and workshop:

Have a great one folks!

📻 — 3 Proven Tactics to Grow Your Email Newsletter

Hi yenizens!

I thought I’d spend a few moments sharing a few lessons that I’ve learned after having been writing email newsletters for a good bit of time now — one of which is still active even after 9+ years!

But, before I share any insights, I was reminded the other day via my daily reading in The Daily Stoic that teachers and educators, especially, should be cautious and conservative with what they share:

Crimes often return to their teacher.

Seneca, Thyestes, 311.

In other words, we often reap what we sow. And Seneca, as we know, paid the ultimate price for mentoring the young emperor Nero.

Consequently, it’s important that you all know that I take great care in curating these daily issues that have gained precious access to your sacred inboxes and I endeavor to only include what I believe is the very best use of your time and consideration.

And, when I share any personal insights, I’ll only share the ones that I know to be empirically true, positively beneficial, and repeatable — there’s an ever-increasing amount of community building “fluff” and it’s starting to clog inboxes everywhere, if you know what I’m saying.

Okay, enough of that. Onto the lesson!

To infinity & community,

— john


Building a growing and engaging newsletter isn’t rocket science but it does take a few raw ingredients that, if done modestly-well, should prove to result in a newsletter that continues to grow in readers and subscribers.

After having launched a dozen or so email newsletters over the last 10+ years, I know what it’s like to see them work and what it’s like to see them “fall on deaf ears” so to speak.

As a consequence I’ve now recognized emergent patterns from the ones that have found success and they aren’t crazy-difficult to execute against; in fact, their outward appearance of simplicity masks the true challenge behind it all: Consistency, consistency, consistency.

But, more specifically, in these 3 areas:

  1. Experimentation, All The Things — Newsletters are powered by humans and humans change. Consequently, a newsletter should be just as dynamic, not static. In fact, a static newsletter is a dead one and one should be open to trying new ways of engaging the audience, test-driving different content types, experimenting with various workflows, and even changing the colors and design based on community feedback. Treat your newsletter like an evolving product and you’ll never fail to experiment.
  2. Be a Pro From Day One — The newsletters that ultimately stand-out and never stop growing are typically ones that operate with a high degree of sophistication that is palpable and obvious; it’s clear that the writer(s) takes their art seriously and they are professional through and through. This is especially important in the beginning where the only thing you may have going for you is the trustworthiness of your delivery schedule and the mountain of value that awaits them when they open it.
  3. Don’t Forget Their Human — Something that I’ve seen happen quite a bit, especially as a newsletter gets “to scale” is that they lose touch with their audience and they all become a growing number and statistic. Sadly, they give up on the one thing that made the newsletter really work! I know this because I’ve fucked this up myself. Now, for the two newsletters that I publish, I send a small, personalized email to each and every new subscriber, the moment they commit their email to me. Imagine that.

These aren’t difficult behaviors but they are hard to do over a long period of time. This is why most folks have newsletters that ultimately end up failing to grow, mostly because they give up on them before they really get going!

These simple behaviors, when repeated over a long period of time, can result in a meaningful and valuable newsletter for everyone involved.

Good luck and have fun.

📻 — Record, Transcribe, Gather… and BTS

Hey yenizens!

I hope you’ve had a great start to your week! I’ve got a quick-fire round of 10+ links that might be worth a click… I’d choose one or two and then forget the rest. 😉

To infinity & community,

— john


Record, transcribe, and capture the best parts of a zoom call? That’s what Grain is all about.


Unstack gives folks a peek into how they’re put together their Slack-powered community — besides a load of how-tos, there’s a some real nuggets of hard-earned truth:

There’s no one tool that makes an online community perfect. I’ve stopped spending valuable time searching for one, and I’ve come to the conclusion that community management and community building is a lot of manual work.

It is… it truly is.


Descript‘s product looks fantastic and their marketing video above was entertaining and clever — I plan on trying it a bit later this week, especially for the amount of video that I do.


Spatial video-chat worlds for work and play? That’s Gather and they’ve recently launched on Product Hunt. I test-drove it and it’s an interesting concept on what is effectively “virtual meetings”:


Should the professional be political? Are we allowed to be? A company that’s at the center of these questions recently is Coinbase:

[The Coinbase] drama revolves around two issues: the narrow one of whether a company should issue a Black Lives Matter statement, and the general one of whether a company should permit or even encourage political activism.

via Atlantic

As community builders and leaders, these topics aren’t “fringe” — they are in our faces every single day. How we handle these things matter.


Just like Jack has said about “software businesses” I believe is true for online communities, especially with the growing number of available platforms for folks to use: You don’t need to write code to build a community.

We live in some really amazing times as community builders!


BTS is still destroying records (and breaking hearts) globally but beyond the record-smashing financials is the way they’ve grown and used technology to build a worldwide audience, especially during the pandemic.

I believe that virtual, live events are going to become an even bigger part of how we build community online — and boy and girl bands may be some of the most obvious pioneers.


Here.fm just raised a round of cash to reimagine what chat rooms could be like by allowing you to customize the “room” as like a… virtual… desktop…? I think that’s the best description that I can muster at this point in time.

Give it a quick whirl and let me know your thoughts.


I’m not always sure of what someone is talking about when they say “employee advocacy platform” but that’s what EveryoneSocial is.

Another internal social network / knowledge base / intranet? What.


And finally, three career-related links:

  1. Breaking Into & Thriving in Venture Capital
  2. A tweetstorm about cofounder relationships
  3. See Your Career as a Product

Have a good one folks.