Sam Parr
Sam Parr is a serial entrepreneur, known best for founding The Hustle newsletter, which was acquired by Hubspot in 2021 and cohosting the My First Million podcast.
I was lucky enough to be early in two of Sam’s communities: Trends and Hampton.
Trends
Hampton
Trends is an offshoot of The Hustle, a daily email newsletter. It’s a paid community with over 13k members in a Facebook group who each pay $300/year. Sam says it grew to $5 million in sales before it was part of the acquisition deal with Hubspot.
Hampton was launched more recently in 2022 and is a private, more premium community of founders making a minimum of millions of dollars in annual revenue. This article focuses primarily on the strategy and tactics behind Hampton.
As a member of both, I was interested in learning how to build one of these communities myself—both as a researcher for Hopin and it’s upcoming community product but also for the readers and writers of my Medium publication Entrepreneur’s Handbook. Here’s what I learned.
Note: this playbook is shared with permission from Sam. No community member information is disclosed in accordance with confidentiality agreements.

“There’s 100% a playbook.”

I asked Sam and his business partner Joe Speiser if they had a playbook for building communities.
“There’s 100% a playbook,” says Sam. “I used it in other communities. But like I’ve never written it out. Just kinda do it. I don’t even know if we could write it out. But we should try.”
But he did share a few of his top keys:

1. Start from the top: the creators should make the content they wanna see and comment like they want others to
2. Be real: no corporate bullshit or jargon. Share vulnerabilities and be honest and stuff like that.
3. Liquidity: community is a marketplace. You need consumers and creators like buyers and sellers in a market. So remove all friction to make it happen.
4. Fomo: create it. It matters.

☝️ These tips are direct from Sam. Now let’s look at the strategies and tractics of how they work.

The genius invention of a fictional character “Howard Hampton” as community manager

“Howard Hampton”
One of the smartest tools in Hampton is the community manager personality “Howard Hampton.”
Howard Hampton is the anonymous concierge of the community. He welcomes new members, posts questions, hosts community events, writes newsletters and updates, and DMs members to keep them engaged.
Howard Hampton’s profile picture is a painted portrait of Benjamin Franklin wearing aviators.
Howard Hampton describes his role like this:

“The anonymity does make it easier to spread tasks if we ever had to. Also creates a through-line for the community. One character forever. But the account is managed by a single person and has been from the beginning.”

The takeaway of Howard Hampton for community builders is that by personifying the brand as an anonymous concierge character, it solves a key challenge in community building — scaling beyond the founder.
Founders often provide the initial magnetism and engagement to get the community off the ground, but community founders move on, get busy, or most commonly: burn out.
A mechanism like Howard Hampton is a smart way to anchor the community to the brand, share management responsibilities, and ensure growth longterm.

Six core elements of a successful community

1. Free vs. paid

• All of Sam’s communities are paid. Annual memberships in the 3–4 figure range.

2. Who to invite first

Sam interviews every single person before inviting them into the community. Everyone is asked the same questions.

• What challenges are you facing?
• What are your career goals?
• What three areas are you looking to learn more about?

At the end of the interview, Sam gives the pitch and pricing but makes sure to be clear that the price is flexible for people who he knew would provide value (e.g., friends) in the community.

3. Member curation

The most important part of building a community is the people you let in. If you get this part right, it makes everything easier.
Start by answering the question: By what criteria are you selecting people? For Hampton, it‘s’ founders making $2 millon a year in revenue. See screenshot below from joinhampton.com.
Hampton membership requirements from Hampton’s website

4. Add value with executive coaches and “Core” cohorts.

One of the main value propositions of Hampton is you join a Core cohort of similar professionals with an executive coach. The cohorts gather monthly for a 3 hour structured meeting to catch up, share openly, stay accountable, get motivated, and so on.

5. Choose a platform where everyone is already.

Joe said they tried Circle but got frustrated with it and ended up just using Slack.
“The issue is where people are naturally — getting them to go to a different platform is really difficult and tends to not work. Slack works well, or discord, or FB groups etc, because everyone is already in those apps and checking them daily,” Joe said.
“Circle was better than slack groups but it didnt matter no one wanted to open a separate app or page to check it daily but if they are in slack anyways, then they toggle over easily.”

6. Keep Your Slack Setup Simple

Hampton organizes itself in 16 channels:

• #general
• #intros
• #geo channels (5) — tagged #geo-city e.g., #geo-nyc
• #talk channels (4) — tagged #talk-topic e.g., #talk-ai
• #member-approval — this one’s interesting. Anyone can vote on new applicants submitted from the website that pings into the channel
• One-off channels that focus on niche industties like #media-companies — for members who run media companies

Takeaway: Limit the number of channels to a handful. Don’t separate conversations out where they’ll get buried or missed. Keep them concentrated for maximum engagement.

Community engagement 101: Forget the programs — just be real and share cool sh*t

If one thing is clear from Sam’s community building, it’s that it’s not about the clever programs you set up, but the way in which you engage the people.
The eponymous Howard Hampton shared a PDF entitled “Cool Sh*t Sam Did to Build Community” — 17 pages of screenshots and examples of how Sam engages to get communities rolling.
Confidential (sorry!)
While the deck is confidential, here are the takeaways for community engagement:

1. Do AMA’s with cool members. AMAs are informal virtual events where individuals can be asked anything by the community. Shameless plug for Session — Hopin’s new video platform built specifically for community events.
2. Call out cool members. Cool people tend to be modest, so prompting members in front of others can get discussions going.
3. Break down stories. Give another POV or dive into the data on a trending story in the news.
4. Get readers to give input on features and content. Before adding anything to the community, get input on how to shape it first.
5. Share and call out cool stuff. Highlight member activity and wins in the community.
6. Share and call out cool stuff you do. Don’t just highlight members, but actually share from your own life what you find interesting. Vulnerability is key, per Sam’s keys above.
7. Ask insightful questions. If it gets quiet, you can always ask an interesting question to get engagement going again. Shameless plug for my conversation starter app Party Qs.
8. Get community input on events. Organize experiences in real life that people want to attend. More on events below.

Key Feature 1: A Weekly Newsletter

Obviously, Hampton’s email newsletter is fire. Email writing is Sam’s wheelhouse.
Hampton sends a weekly newsletter every Monday.
The newsletter follows this outline:

1. Summary of insights, news, roundups, and great discussions happening in the community (i.e., slack links) and often a photo of members who met in person.
2. Highlight new members
3. Upcoming speakers and events
4. “Last But Not Least…” (a deeper dive on something cool from a member)

Takeaway: A weekly newsletter is one of the best retention tools for your community. It’s a great way to keep people informed and coming back.

Key Feature 2: Community Events

Hampton hosts a number of in-person and online events. In addition to the monthly Core groups with coaches, there are a few other programs:

1. Fireside Chats — interviews and presentations from some of the heavy hitters in the group.
2. Biweekly Mixers — video calls to meet members using breakouts and discussion prompts.
3. Dinners and retreats — in-person meetups and overnight stays for better bonding between members.

Takeaway: Events deepen connections by lettting members get away from the noise of the office, home, email, slack, etc. and be present face-to-face with people to learn and do cool stuff.

Your turn

I took all of the above and organized it into a step-by-step guide to launch your own community. You can find the Gdoc checklist here for free:

• How to Launch A Cool-A** Community [Checklist]

How to Launch a Cool-A** Community [Checklist]

In the end, whether you’re a creator or a brand, there’s a lot of discussion happening right now about the increasingly important role online communities play in building businesses today. From retention to acquisition to product feedback, a community can provide incredible value when it’s done right. This is something I’m hoping to explore more of this year. For now, I’m grateful to know Sam Parr and the exemplary work he’s already done in this space.
More to come, but I’ll leave you with this. I’m curious:
What communities are you in? What makes a community valuable? I’d love to hear thoughts in a response below 👇