Behind the Build

How Dr. Des turned a side hustle into a $30K/month community business (in under two years)

Dr. Desiree Strickland started a community while on maternity leave in a field that told her money wasn't possible. In under two years, she has close to 950 paid members, $30,000 in monthly recurring revenue, and a room full of people telling her she changed their lives. In this episode, you'll learn: How she launched a course and community simultaneously to guarantee early momentum Why she held the line on pricing when members told her it was too high—and why she was right to The time-bound resource strategy that reliably spiked sign-ups on the last day of every month How a founding member became her community engagement manager—and then won her first consulting contract through connections she made inside the club This one is for anyone building on the side and wondering when it becomes the main thing. The conversation doesn't stop here—join the discussion and ask the guest your own question at community.circle.so/c/behind-the-build Behind the Build is a candid conversation series with the people behind thriving communities. Most communities look polished from the outside—this show goes inside. Each episode, we sit down with a community business founder and dig into a specific win: the real numbers, the honest decisions, and the messy middle that made it happen. No theory. No highlight reel. Just the actual story. Hosted by the Circle community—where community builders come to build, grow, and connect. New to Circle? Visit circle.so to learn more.

• Transcript

The honest truth about building a six-figure community business

Four years ago, Jessie Montague wrote one honest Instagram post to a couple hundred followers and half expected silence. Today, Honest Hounds has over 1,000 active members, 100 neutral walk locations across the UK, CPD-accredited courses running at near 100% completion, and six figures in recurring annual revenue. What makes this episode worth listening to isn't just what she built—it's how she built it, and what she had to unlearn along the way. Jessie got so focused on being a CEO that she lost the part of the work that made her good at it. This episode is about what happened when she found it again. In this episode: How Jessie achieved near 100% course completion in an industry where most people never finish what they buy Why her affiliate trainers refer their own clients to her, and what that says about building a referral system that works both ways The moment she tried to step back and be more of a CEO, and what it cost her before she course-corrected The conversation doesn't stop here—join the discussion and ask the guest your own question at community.circle.so/c/behind-the-build Behind the Build is a candid conversation series with the people behind thriving communities. Most communities look polished from the outside—this show goes inside. Each episode, we sit down with a community business founder and dig into a specific win: the real numbers, the honest decisions, and the messy middle that made it happen. No theory. No highlight reel. Just the actual story. Hosted by the Circle community—where community builders come to build, grow, and connect. New to Circle? Visit circle.so to learn more.

The freemium pivot that unlocked 6K members

Joana Rocha and her co-founder had 400,000 social followers and a paid community that wasn't getting traction. Nobody was joining. Nobody was engaging. The pivot to freemium changed everything—and the conversion system they built inside Circle to turn free members into paying subscribers is something most community builders haven't seen before. Today TechTalk UK has 6,500 members, a 20-minute founder welcome call for every new paid member, and a model built around connection first, content second. In this episode: Why giving away free content builds the trust that leads to paid conversion, not the other way around How Joana built an onboarding automation that converts free members to paid without feeling like a sales pitch What she learned from launching two community hubs at once, and why stripping it back was the right call The conversation doesn't stop here—join the discussion and ask the guest your own question at community.circle.so/c/behind-the-build Behind the Build is a candid conversation series with the people behind thriving communities. Most communities look polished from the outside—this show goes inside. Each episode, we sit down with a community business founder and dig into a specific win: the real numbers, the honest decisions, and the messy middle that made it happen. No theory. No highlight reel. Just the actual story. Hosted by the Circle community—where community builders come to build, grow, and connect. New to Circle? Visit circle.so to learn more.

• Transcript

From courses nobody finished to a six-figure community business

Ernie Svenson had courses lawyers were buying but not finishing. The problem wasn't the content—it was the isolation. When he built community around those courses, everything shifted. Members started showing up not just for lessons, but for each other. Today, The Inner Circle has 300 members generating six figures annually, with around 100 of them on a $239/month premium tier driven almost entirely by AI learning. The dirty little secret of course building is that at best 4% of people actually finish what they buy. Ernie knew that. He built something to fix it. In this episode: Why Ernie stopped giving his best asset away as a free lead magnet—and what happened when he put it behind a paywall How he got skeptical professionals (lawyers, specifically) to trust each other enough to actually post and participate The weekly poll tactic that drives engagement regardless of the topic, and how AI tools now let him run the whole community himself The conversation doesn't stop here—join the discussion and ask the guest your own question at community.circle.so/c/behind-the-build Behind the Build is a candid conversation series with the people behind thriving communities. Most communities look polished from the outside—this show goes inside. Each episode, we sit down with a community business founder and dig into a specific win: the real numbers, the honest decisions, and the messy middle that made it happen. No theory. No highlight reel. Just the actual story. Hosted by the Circle community—where community builders come to build, grow, and connect. New to Circle? Visit circle.so to learn more.

• Transcript

How to run a 2,000 person summit entirely on Circle

Rachel Starr didn't just host a virtual summit. She ran a three-day, 2,000-person event with 22 sessions, daily live panels, and a private podcast, all inside Circle, all without a single tech issue. Then she used it to launch her paid membership—converting over 200 attendees into members on the day they registered. In this episode, Rachel breaks down exactly how she pulled it off: the free-to-paid funnel, the separate onboarding experience that kept help requests to almost zero, and why the biggest returns from a summit come long after the event ends. She also shares what she'd do differently—and the one thing she'd tell any founder who's been sitting on the idea. In this episode: How to structure a summit-to-membership funnel that converts on day one Why separating your summit onboarding from your community onboarding changes everything What "long-term revenue thinking" actually looks like in practice The conversation doesn't stop here—join the discussion and ask the guest your own question at community.circle.so/c/behind-the-build Behind the Build is a candid conversation series with the people behind thriving communities. Most communities look polished from the outside—this show goes inside. Each episode, we sit down with a community business founder and dig into a specific win: the real numbers, the honest decisions, and the messy middle that made it happen. No theory. No highlight reel. Just the actual story. Hosted by the Circle community—where community builders come to build, grow, and connect. New to Circle? Visit circle.so to learn more.

• Transcript

From idea to six figures in one year—with zero churn

Twelve months ago, Tom O'Reilly had an idea. Today he has a six-figure membership business with 950 members, a 100% renewal rate, and 10 to 20 active conversations happening every week—driven by members, not just Tom. He grew it using three marketing channels. One of them converts at 10%. This episode is proof that you don't need a complicated strategy. You need clarity, the right platform, and the discipline to keep it simple. In this episode: How Tom achieved a 100% renewal rate in year one and the community experience that made it possible Why he shifted from course sales to team-based membership pricing—and why that one decision changed his revenue model Why choosing Circle over Slack wasn't just a preference—it was make or break The conversation doesn't stop here—join the discussion and ask the guest your own question at community.circle.so/c/behind-the-build Behind the Build is a candid conversation series with the people behind thriving communities. Most communities look polished from the outside—this show goes inside. Each episode, we sit down with a community business founder and dig into a specific win: the real numbers, the honest decisions, and the messy middle that made it happen. No theory. No highlight reel. Just the actual story. Hosted by the Circle community—where community builders come to build, grow, and connect. New to Circle? Visit circle.so to learn more.

• Transcript

How a free daily writing ritual became a $500K community business

London Writers' Salon started as monthly meetups across London. Today it's a global community of 1,800 paying members generating half a million dollars annually—built around a deceptively simple ritual that happens four times every single day. Up to a thousand writers join across four time zones. Every day. Without fail. Matt Trinetti and his co-founder Parul didn't build a course library or a content platform. They built a place where writers actually write—and then gave members the keys to run it. In this episode: How a two-week experiment in March 2020 became a daily ritual that hasn't stopped since Why flipping from free to paid actually increased commitment rather than losing members How giving members ownership of the community reduced founder dependency and grew the business at the same time The conversation doesn't stop here—join the discussion and ask the guest your own question at community.circle.so/c/behind-the-build Behind the Build is a candid conversation series with the people behind thriving communities. Most communities look polished from the outside—this show goes inside. Each episode, we sit down with a community business founder and dig into a specific win: the real numbers, the honest decisions, and the messy middle that made it happen. No theory. No highlight reel. Just the actual story. Hosted by the Circle community—where community builders come to build, grow, and connect. New to Circle? Visit circle.so to learn more.

• Transcript