Why Most Communities Fail (And What I Do Differently at The HoLT)
A blueprint for community leaders who want members that stay, contribute, and genuinely care about each other.
You can build a community in a weekend. A landing page, a Slack group, a pricing tier, a welcome email. Done. The hard part (that nobody warns you about) is keeping it alive.
The average community loses up to 10% of its members every single month. That means if you’re not constantly replacing the people walking out the back door, you’re shrinking. And most founders are so focused on acquisition they never stop to ask why people are leaving in the first place.
I’ve spent nearly four years figuring out the answer to that question. The HoLT is a membership community for freelancers, solopreneurs and small business owners. Over 500 members, predominantly UK-based, paying £65 a month or £650 a year for access to masterclasses, a thriving community platform, networking events, wellbeing sessions, a book club, and a founder who is genuinely, obsessively, in there every single day. That founder is me.
Recently I went live with three long-standing HoLT members; Sarra Richmond (ghostwriter and voice expert), Robyn MacMillan (founder of the Everburn Agency), and Hedi Shah (mindfulness teacher and body worker). All three of them had paid for and left other communities before finding The HoLT. And what came out of that conversation was the clearest articulation I’ve ever heard of what we actually do here, and why it works.
Here’s what they said. And here’s what you can take from it.
1. The gap between the landing page and the reality
“The reality versus the rhetoric that you’re fed. That’s the biggest difference. I’ve joined so many places, paid a lot of money, not got what I expected. Whereas the HoLT has always just consistently delivered more than I thought was possible.” — Robyn MacMillan
Every community makes promises. More clients. Better connections. Faster growth. The problem isn’t the promise, it’s the canyon between what people imagine when they sign up and what they actually experience on day one.
Robyn describes herself as a sceptical human. She’s joined communities, clocked that they weren’t going to deliver, and left. She stayed in The HoLT because it was the only place where the reality matched - and then exceeded - the expectation.
That gap is entirely within your control as a founder. If you’re promising transformation, you need a community that can actually deliver it. And if you’re not sure whether you can deliver it, you need to audit your promises before you audit your membership numbers.
The takeaway: Walk through your own onboarding as if you’re a new member. What did you promise on the sales page? What does someone actually experience in their first 30 days? If there’s a gap, close it before you spend another penny on marketing.
2. Business first, relationship second, and why it kills communities
“A lot of those places I joined were business first, relationship second. Everything felt fake and surface level and shallow. Like those networking events where you can tell someone glazes over when you’re not of use to them.” - Hedi Shah
Hedi paid £1,200 a year for a community she left before her membership expired. She still had credit. She left anyway.
The reason? It was transactional. The implicit message was: be here to close sales or don’t bother being here. And if you’ve ever been in a room - virtual or physical - where someone is looking over your shoulder for someone more useful, you know exactly what that feels like. I’ve been in those rooms. They’re grim.
The HoLT is not built on that model. People get clients from within The HoLT all the time. Robyn has a long list of clients from the community, Sarra has had significant collaborations and clients come through it, as has Hedi, but that’s a byproduct of genuine relationship-building, not the goal.
The point is not to join to get clients. The point is to learn skills that will help you to get clients. To make friends who become referrals because you’ve built actual trust with them. That’s a very different thing, and people can feel the difference immediately.
I’ve had members come to me frustrated that they haven’t signed clients from The HoLT. And I say: where in my marketing did I promise you clients? That’s not what this is. If you’re here just to sell, it’s not the right place for you. And I’ve had that conversation with members and encouraged them to leave, because it’s not fair on everyone else. They’re not here to be sold to, but plenty of them do buy from one another.
The takeaway: Examine the implicit culture inside your community. What behaviours are being modelled and rewarded? If someone joins and the first thing they see is promotional posts and sales pitches, you’ve already told them what kind of place this is.
3. The founder has to actually show up
“No matter what you do, you don’t remove yourself from the community. You’re always present. And the culture that you want us to have, you live and breathe it.” — Robyn MacMillan
This one sounds obvious. It isn’t.
Plenty of community founders are present at launch, present for the first few months, and then gradually they hand things off. They hire a community manager. They show up for the big events but not the quiet days. The members notice. Of course they do - most of them joined at least in part, for proximity to the founder.
I’m in The HoLT for a minimum of two hours on a quiet day. I see every single message posted in the community. I make it my job to. I respond to DMs, I tag people in relevant conversations, I notice when someone’s gone quiet. I am not a figurehead. I’m a participant. And since I stepped away from my LinkedIn training business at the end of 2024 and made The HoLT my full-time job, that’s only intensified.
Despite being an introvert, I genuinely love spending time with my members. Because I know that anyone who’s been attracted to my brand and decided to join is almost certainly someone I’m going to like. I trust my own brand filter.
And what you see from me online is what you get in person. Members come to events and say it every time: everyone is exactly who they are online. There’s no facade to crack because there was never one to begin with.
The takeaway: Your presence isn’t a bonus feature. It is (at least partly) the product. If you’re building a community where you’re not genuinely, personally showing up, you’re building a content library with a chat function. That’s a different thing.
4. Don’t dictate what members need. Listen and build.
“You don’t make assumptions about what the member needs. You ask people questions and you’re in the community, which results in you developing things that the community actually wants.” - Hedi Shah
Hedi mentioned early on that she wished there were networking events as part of The HoLT. She’d joined for the community, not the masterclasses, and she wanted to meet people. I listened. Eventually I had the capacity to introduce speed networking sessions and weekly community calls, and Hedi told me that was the moment The HoLT felt complete for her.
BarryBot, our custom GPT that helps members find the right masterclass from a library of over 200 sessions - came from the same place. We’re launching him very soon. I noticed members were overwhelmed by the sheer volume of masterclasses in our library. I didn’t assume I knew the solution. I sat with the problem, then spent five hours creating summaries of every historic masterclass so we could feed it into the GPT properly. I only knew the problem existed because I was in there, watching, listening, and paying attention.
That’s what active listening looks like inside a community. Not surveys that go unanswered. Not assumptions. Observation, conversation, iteration. You have to be present enough to spot the problems people aren’t directly telling you about.
The takeaway: What are your members not saying directly, but showing you through their behaviour? Where are they getting stuck, going quiet, or not engaging? That’s where your next community feature lives.
5. Culture is contagious but only if the founder is the carrier
“By proximity, your generosity encourages members to become more of that kind of person.” - Hedi Shah
This is probably the thing I’m most proud of, even though I can’t take full credit for it.
At our last Christmas party, one of our members, Steph, messaged the WhatsApp group to say her blood pressure had dropped badly on the train. Members who had never met each other in person organised immediately. One offered to bring electrolytes. Another went and met Steph from the train and took her to get something to eat. The electrolytes were waiting for her when she arrived at the party.
None of them had met before. They just did it. Because that’s the culture here.
I do think it filters down from me. I’ll get off a train early to help a member on crutches navigate the tube. I notice when someone goes quiet and I check in privately. I send personal messages when I know someone’s going through a hard time. I don’t do it as a strategy. I do it because it’s just what you do when you actually care about people. But the community has picked it up and made it their own, and now it happens whether I’m involved or not.
“You create this culture so we can all be us. And that is powerful, because then I’ve got to know the real version of people.” - Robyn MacMillan
The takeaway: You cannot engineer culture through rules and content pillars. You model it. Every response you give in public, every DM you send, every time you show up when you don’t have to, you’re teaching your members what this community is. They’re watching. And they’re learning.
6. The pick-and-mix model. Freedom without pressure
“The HoLT is like a pick and mix of joy. I can dabble in and out without getting: why weren’t you at this call? Which I’ve experienced in other communities. The community needs to support me, not me paying to support the community with my time and energy.” - Robyn MacMillan
One of the quiet killers of community engagement is obligation. When members feel they have to show up - that their absence will be noticed and commented on - they start to dread logging in. The community stops feeling like a resource and starts feeling like another job they’re failing at.
I designed The HoLT to be the opposite. You come when it serves you. You skip what doesn’t fit your season. Nobody is chasing you for missing a call. The masterclass library means you can catch up on your terms. The wellbeing circle is there if you need it. The networking events are there if you want them. The rant channel is there for the days when you just need to say something out loud.
Different members use completely different parts of the community, and that’s entirely by design. Some people barely touch the masterclasses and live in the community chat. Others binge through the library every week and barely post. Both are valid. Both are welcome. And that flexibility is exactly what keeps people in for years rather than months.
The takeaway: Are you creating pressure that’s quietly driving people away? Look at how your onboarding and community messaging talks about attendance. Is it invitation or expectation? The language matters more than you think.
7. Vulnerability needs a container and you have to build it deliberately
“I’ve never been that vulnerable with a group of people. Maybe in person. But it’s very special to have something like that hosted online.” - Robyn MacMillan
Hedi Shah runs a monthly wellbeing circle inside The HoLT; a space for members to set intentions, share what’s on their hearts, and be witnessed. When she first pitched it to me, there had been a few previous attempts at wellbeing-type content in the community that hadn’t quite landed. I said yes anyway. Let’s test it and see.
It became one of the most valued things we do. Members share grief in those sessions. Men who would never open up in other spaces share things they say they’ve never said elsewhere. Robyn has a permanent block in her calendar for it that no client can move.
“You see the truth of humans. You see the humans behind all the ways we have to show up, all the responsibilities we carry. Every time I leave that space, I feel blessed to be in this community.” - Hedi Shah
We also have a mental health channel, a rant channel, and a gratitude channel. These aren’t gimmicks. They exist because being a solopreneur is genuinely hard on your mental health, and pretending it isn’t doesn’t make it less true. It just makes it lonelier. We have therapists, psychotherapists and mental health professionals within the membership who will step in if something serious comes up. We’re not offering free therapy, but we are offering a space where you can say “I’m not okay today” and know you’ll be met with warmth rather than silence.
The takeaway: Does your community have a container for the hard stuff? You don’t need to be a therapist (please don’t position yourself as one), but giving people a safe (well, as safe as is possible in an online forum) channel to be honest is one of the most powerful retention tools available. People don’t leave places where they feel safe.
8. Equality is a business model
In most community models, the more you pay, the more you matter. The free tier gets you in. The mid tier gets you more. The top tier gets you access to the founder. Your worth as a member is determined by your price point.
I built The HoLT on the opposite principle. There is only one tier inside the community. However, we also offer The Vault (totally separate) which just contains the masterclass recordings. Within the full community (The HoLT), everyone is equal. £65 a month or £650 a year, and that’s it. No upsells. No premium access tiers. No trying to sell you into my other services and products. A member who joined last week has exactly the same access as someone who’s been here three years. Including access to me.
This isn’t charity. It’s a deliberate choice that shapes everything about the culture. Nobody feels like a lesser member. Nobody is sitting in the cheap seats wondering what they’re missing. And when I give someone my time and attention - which I do, regularly, genuinely - it means something, because it was never for sale in the first place.
The takeaway: Look at what your tiered model is actually communicating. If your lower tiers feel like holding pens for people who can’t yet afford the real thing, that’s the experience your members are having.
What it actually comes down to
After nearly four years, 500+ members, and a churn rate well below industry average, I can tell you that the formula isn’t complicated. It just requires something harder than a good marketing strategy.
It requires a founder who genuinely wants to be there and makes the time to do so.
Who likes the people they’ve built the community for. Who shows up on the hard days and the boring days and the days when nothing interesting is happening. Who listens more than they broadcast. Who models the culture they want to see and then trusts the community to carry it forward. Who builds from abundance rather than scarcity - sharing everything, gatekeeping nothing, trusting that the more people win inside this space, the better it is for everyone in it.
I built The HoLT because it was the community I needed when I was starting out and it didn’t exist. I couldn’t afford to hire experts in sales and marketing and copywriting and automation and mindset. I couldn’t find a place that felt human rather than transactional. So I built it myself, for the person I used to be, and I tried to fill it with the things I wish I’d had.
Communities don’t fail because the niche was wrong or the platform was bad or the timing was off. They fail because the founder wasn’t actually in there. Because the promises didn’t match the reality. Because members felt like leads rather than people.
That’s it. That’s the blueprint.
The HoLT is a membership community for freelancers, solopreneurs and small business owners. Membership starts at £65/month or £650/year.
And if you’re a solopreneur, freelancer, small business owner, or a lonely employed person looking for a fun, friendly cult crew, why not come and join us?
