Friday

In 2013, Luke left a startup job partly because his manager never checked in with him about his concerns. Rather than have an uncomfortable conversation, he simply found a new opportunity elsewhere. Reflecting on that experience, he realized that technology could help break down communication barriers and enable regular feedback loops between employees and managers. The idea percolated for nearly three years before he decided to build it.

In late 2015, Luke started coding a side project in Ruby on Rails, hoping it would generate an extra $1,000 per month. He brought on a contractor from day one to handle development, recognizing that outsourcing code freed him to focus on go-to-market and validation. He shipped in January 2016 and waited three months for his first customer—earning $45 a month. "I was over the moon," he recalled. Rather than writing code himself, paying someone else to build meant he could focus on finding customers while maintaining his day job.

Luke's customer acquisition strategy was scrappy but creative. He started by emailing everyone he knew who might be interested. He published 30-40 blog posts of 1,500+ words on topics like "weekly check-ins" and "one-on-ones," which gradually ranked in search and drove organic traffic. More unconventionally, he spent months leaving comments on Harvard Business Review articles about leadership and management—a tactic he acknowledged was embarrassing, including using a VPN when he got banned. But it worked: many early signups came from HBR comments. He also experimented with Facebook ads and other paid channels but found they diluted his activation rate. His lesson: don't throw money at a leaky funnel. Focus on retention and conversion first.

Luke started with a freemium model but quickly switched to a free trial when he realized he was burning cash supporting unpaying users. The shift to trials brought 3-5 new paying customers almost immediately. One of his biggest mistakes came when he pivoted the product toward HR departments. The gravitational pull was strong—HR teams were reaching out, he was writing HR content—but the underlying problem was misalignment. HR buyers were skeptical about weekly check-ins rolled up to them, and adoption suffered. People worried it was an "employee oversight tool." "I just became disenfranchised," Luke said. He also had a near-catastrophic incident when he onboarded 150 people from a large customer, then shipped code without proper testing. A single line of code caused emails from one company to be sent to another—leaking PII. He got an email Friday morning and manually fixed it by ripping out API keys, but the lesson was clear: some features demand rigorous QA, not just move-fast-and-break-things. He refocused the product as a team communication tool for remote leaders, not an HR system, and that renewed his excitement.

By 2019, Luke had grown the side project to $10K MRR while working full-time and raising a family—a grueling pace he credits with high stress. A friend at a local Portland nonprofit got him a free booth at TechCrunch Disrupt in September 2019. A week before the event, he was introduced to a Boston-based venture firm, had what he felt was his best pitch yet, and received a term sheet. He raised approximately $100K and finally quit his day job in late 2019. The team rebuilt the product in October 2019 through January 2020, focusing on a simpler, more customizable interface for any routine team communication—not just employee-manager check-ins. They launched on Product Hunt in early February 2020, just days before COVID-19 forced the world to work remotely. "Our addressable market grew 100x overnight," Luke said. As of the interview (mid-2020), Friday has three full-time employees and several contractors, with a goal of 10 people by year end.