Circle

While working at Teachable, Andrew Guttormsen, Sid, and Rudy noticed a critical gap in the creator economy. Creators had plenty of tools to host content—blogs, courses, videos—but almost nothing to build and manage the communities around their audiences. "There weren't many tools to host the creator's audiences," Andrew recalls. This insight struck them as the real pain point: creators needed a way to bring their fans together, not just broadcast to them.

Sid and Rudy started building Circle as a side project while still at Teachable. They completed the first version in just one month, then spent two additional months iterating based on feedback from a carefully curated group of early users. Their distribution strategy was scrappy but smart: they invited creators they already knew from Teachable, plus others from Rudy's web development and design business. For several months, they added just one or two customers every few weeks, staying close to each user to understand their needs. By January 2020, they felt they had enough of a product to justify starting a company full-time.

From January through August 2020, Circle's marketing was almost entirely organic. They created a landing page with an email waitlist and grew it to thousands of interested creators. The signup process included a survey asking about use cases and willingness to pay—a qualification mechanism that helped them focus on the best fits. The real magic happened in sales: Andrew personally conducted hundreds of 1-on-1 demos, averaging 7-10 calls per day at 30-40 minutes each. This manual, high-touch approach was tedious but incredibly effective for learning what customers needed and building loyalty. They also created their own Circle community for customers, creating a feedback loop that deepened engagement and sparked word of mouth.

The August 2020 public launch was the inflection point. Circle launched on Product Hunt and hit #1 for the day—partly because they had pre-warmed their waitlist and asked them to support the launch. Press coverage from TechCrunch and elsewhere amplified the effect. The results were dramatic: "The launch particularly brought a huge growth and boosted revenue—we did as much revenue in that month as we had done in the six months before it." By December 2020, they had raised $5.5M, assembled a 12-person team, and were adding hundreds of customers monthly. Andrew's one regret was not being clearer earlier about customer fit. He wished he'd been more upfront about disqualifying bad-fit customers rather than demoing to everyone, given the responsibility creators felt when hosting their communities on the platform.

Circle had become a venture-backed darling in the community platform space, competing against Slack, Facebook Groups, and other incumbents. The company stayed focused on product engineering and customer success, hiring primarily engineers and support staff. Andrew's key lesson: "People are very open-minded and very patient if you're just upfront with them. Don't try and make everything perfect before getting it out there into the world."