After Raymond Hou (Raymond) left traditional employment in 2020 and co-founded the “Raymond Thirty” brand with his wife Yuzu (Song Zhiyou), he did not first use free content to build a large audience and then turn to monetization. While the brand was still in its early stage and had only a few dozen people, he launched paid content and a membership subscription service. In 2021, this decision took shape as the “Lifehacker Journey / Lifehacker Premium” paid subscription, which ran for more than six years. Raymond later described it as his “most correct and also worst” decision: it established paid readers and trust relationships early, but also brought long-term costs in influence and effort from “locking the content I worked hardest on behind a paywall.”
Decision Background
In early 2020, the pandemic interrupted the overseas career plan Raymond and Yuzu had made. They retreated from Beijing to Taiwan and decided to commit themselves fully to their own business. For Raymond, starting a business required more than “doing the familiar things from before,” such as writing Facebook posts or long blog articles for a broad audience. He judged that he needed a medium that was “more private, more substantial, and better able to build trust.” This judgment connected to an earlier shift: when the brand had “no large resources behind it” and its business model did not target the mass market, its operating mindset had to shift from “traffic thinking” to “membership thinking.” He viewed a newsletter as the entry point. A person willing to give an email address and receive regular messages was already demonstrating trust, and the relationship was not governed by social-platform algorithms.1
Why Choose Paid Subscriptions Instead of Scaling First and Monetizing Later?
Raymond described the original position of the subscription service simply: use himself as a test subject, organize good methods he had used—digital tools, personal productivity, and new-era ideas about work—and share them with people who wanted to work smarter. He chose to build a “private domain” and paid membership community first, rather than growing the brand and products before returning to build relationships. Years later, he treated fellow content creators Waki and Zhang Xiuxiu, who also left employment to start businesses around 2020, as peers for comparison. All of them tried to build businesses through their own content, but each accumulated brand scale, in-person connection, and membership relationships in a different order.2 Raymond initially chose a niche, in-depth approach. The cost was lower brand visibility and influence, but he says he was satisfied with his situation and believes different paths involve different trade-offs. This peer context is key to understanding the decision: it was not a passive monetization tactic, but an active choice about “what to accumulate first.”
The Subscription Service’s Evolution
Starting with a paid newsletter, this line of work gradually grew into an ecosystem. In 2021, Raymond turned methods accumulated through self-study and remote work into paid in-depth articles, launched the first review bootcamp and courses related to Notion, and moved the community from a Facebook group to the Discord server “Lifehacker Islands.” In the following years, it expanded into annual gatherings, smart-home meetups, study groups, in-person trips, and other offline and online events. The number of people participating in the member community once exceeded one thousand. This line of work also intersected with Raymond’s other businesses: needs that emerged in the subscription community indirectly gave rise to later Notion bootcamps and The Super Individual’s Way of Working. Multiple public retrospectives—the six-year reflection, five-year record, and upgrade announcement—describe the journey as “an island we never expected, but raised together.”3
The Paywall Dilemma: Why It Was Also the “Worst” Decision
Raymond’s reservations centered on the structural contradiction of “membership becoming a wall in the relationship.” It reached a low point during a trip to Australia in 2023, when he spent several nights wondering whether to shut down the service.4 The contradiction came from two directions. First, the rational concern: in-depth articles he spent nearly ten hours writing each week were locked behind a paywall, limiting their reach. A mentor had once advised that “content creators should spend thirty percent of their effort creating and seventy percent promoting.” The paywall approach was almost the opposite: it “hid the best content, the content I cared about most,” and would in the long run hinder the growth of a niche brand. Second—and more sharply—the emotional concern: Raymond firmly believed that subscriptions were fundamentally a relationship of trust, yet he found a counterintuitive cycle. The more carefully he helped members grow, the lower their renewal rate could become, because after growing they might no longer need the community. The question “What exactly are people subscribing to?” troubled him for two years.
The Answer and the Shift
Raymond ultimately did not close the service; instead, he redefined what it “sold.” The turning point came from the community itself. During what he described as the lowest period of his life, members’ involvement—volunteering at the annual gathering, leading study-group teams, and having sincere late-night conversations on Discord—gave him the energy to continue. He concluded that the greatest value of the paid service was not the content he wrote, but the community “space” itself. Accordingly, starting in 2026 Lifehacker Premium was comprehensively upgraded. Its position shifted from a content subscription that “gives you methods” to a buffer and experimental space in life that “accompanies you as you turn a corner.” Pricing would no longer be based on the amount of content. Instead, qualifications, depth, and participation would be used to select partners who shared the philosophy. The community would be deliberately smaller, with a membership cap and an application form, to keep its culture and trust from being diluted. The specific annual fee and benefits in this upgrade are operational information and are not expanded here.
Significance
This decision reflects Raymond’s consistent trade-off in Business Thinking: put the accumulation of trust and relationships ahead of traffic and scale, accepting lower visibility in exchange for deeper connections. It is intertwined with his Writing and content strategy—the paywall both protects and limits content—and is a representative case of the “small, beautiful, and deeply cultivated” side of his Super Individual path. The dual assessment “most correct and also worst” makes the subscription line both a long-term asset and a source of tension that remained unresolved until it was provisionally brought together in 2026 (see The Subscription-Service Low Point: Payment Became a Barrier to Getting to Know Each Other and Lifehacker Premium).
Representative Quotes
“What really makes people stay has never been the amount of content; it is ‘what kind of people are here.’”
“I’m not subscribing to a magazine. I’m participating in an experiment of our era.”
Sources
Footnotes
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Raymond Hou, “Among the Creators Who Left Their Jobs and Started Businesses the Same Year as Me, Waki Is a Special Case,” public Facebook post, 2026-06-16. View original''') put(‘課程從Hahow拉回自架’,‘bring-courses-from-hahow-in-house’,‘Bringing Courses Back from Hahow to a Self-Hosted Platform’,‘2026-06-20T16:00:00+08:00’,'''Raymond Hou (Raymond) made a decision spanning several years about online-course distribution: move the center of revenue and effort away from the third-party course platform Hahow and back to his own website, lifehacker.tw. This was not a one-time “unlist and move” operation, but a phased process of bringing learner relationships, pricing power, and learner data back under his own control. Understanding the decision requires looking at what Raymond was evaluating: not which platform brought the most people, but which model would let him maintain long-term control over his relationships with learners. ↩
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Raymond Hou, “Building a Paid Membership Community for Five Years? The Full Record of Lifehacker Islands and the Subscription Service,” WordPress article, 2026-03-01. View original ↩
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Raymond Hou, “Why Did I Decide to Upgrade the Lifehacker Premium Paid Membership Community in Full?” WordPress article, 2026-01-08. View original ↩