Confidence and Getting Lucky  ## Metadata - Author: [[Marieke van de Rakt]] - Full Title: Confidence and Getting Lucky - Category: #articles - Document Note: --- tags: - #wordpress - #open_source - #plugin_business - #entrepreneurship - #timing - #confidence Author: Marieke van de Rakt Source: Post Status (Article) Reference: https://poststatus.com/confidence-and-getting-lucky/ date created: {{date:YYYY-MM-DD}} {{time:HH:mm}} --- # Title: Confidence and Getting Lucky — Reflections on Building a WordPress Plugin Business ## Table of Contents: - [📝 Summary](#-summary) - [📖 Main Content](#-main-content) - [🗒️ Notes](#-notes) - [📖 References](#-references) - [🗣️ Paraphrase](#-paraphrase) - [📰 Newsletter](#-newsletter) - [✅ Action Items](#-action-items) - [🧪 Hypotheses](#-hypotheses) - [📊 Methodology](#-methodology) - [❓ Questions](#-questions) - [🔮 Future Research](#-future-research) - [💡 Implications](#-implications) - [🧠 Learning Styles Assessment](#-learning-styles-assessment) - [📊 Accessibility Assessment](#-accessibility-assessment) - [🌍 DEIB (Diversity, Equity, Inclusion, and Belonging) Assessment](#-deib-diversity-equity-inclusion-and-belonging-assessment) - [✅ Logical validity](#-logical-validity) - [🔍 DARVO Analysis](#-darvo-analysis) - [🔍 SEO Evaluation](#-seo-evaluation) - [🎯 Conclusion](#-conclusion) ### References: - Marieke van de Rakt. “Confidence and getting lucky.” Post Status, 2023-10-06. - Research on startup success and timing (e.g., Bill Gross’s TED talk on startup timing as a key success factor). ## 📝 Summary: The author reflects on “confidence after the fact”: only after stepping back from Yoast did she fully appreciate how hard and rare it is to build a thriving WordPress plugin business. She outlines structural challenges—open source dynamics enabling rapid copying, competition against free plugins (including one’s own freemium tier), massive compatibility burdens at scale, and community norms that penalize overt sales tactics—concluding that success is both “madness” and “heroic.” She tempers this pride with humility, noting that timing accounts for a large portion of startup success, and advises readers to treat “expert” lessons (including hers) with a grain of salt because luck plays a meaningful role. Direct quotes for context: - “Building a WordPress plugin or product business is super hard... It is madness. And it is heroic if you succeed.” (0%) - “My conclusion: building a thriving plugin business is superhard... research clearly shows that about 40% of the success of startups... is based on timing.” (50%) ## 📖 Main Content: The article juxtaposes two truths: - Earning confidence: In hindsight, growing Yoast amid open source constraints required exceptional execution. Challenges included feature-copying by competitors, monetizing amidst a strong free ecosystem, and engineering/support demands for millions of installs. - Acknowledging luck: Even with skill and strategy, timing substantially shapes outcomes. Therefore, playbooks from “successful founders” are context-bound and should be applied with caution. Personal insight: - For WordPress ecosystem builders, this piece validates the hidden labor (QA matrices, edge-case support, compatibility stewardship) and the reputational constraints on growth tactics. It also models healthy founder humility, encouraging postmortems that separate controllable levers (quality, community trust, testing) from exogenous variables (market timing, macro shifts). ### 🗒️ Notes - “Confidence after the fact” (0%) - Retrospective recognition of achievement once operational pressures ease. - Cognitive shift: from “anyone can do it” to “this was uniquely hard.” - Structural difficulty of WordPress plugins (0%) - Open source + permissive licensing → easy feature copying. - Freemium pressure: paid extensions vs. free alternatives, sometimes one’s own. - Scale complexity: millions of installs → innumerable plugin/theme conflicts. - Operational demands: high-quality code, extensive testing, ongoing support. - Community norms on sales (50%) - “You can’t be too salesy” without criticism; reputational risk can invite forks/copies. - Tension: need revenue to fund quality and support vs. community expectations. - Humbled conclusion (50%) - Success requires heroics and resilience. - Timing may account for ~40% of startup success; luck is real. - Advice from “experts” should be applied carefully; survivorship bias exists. ## 📖 References: - Post Status article: Confidence and getting lucky — https://poststatus.com/confidence-and-getting-lucky/ - Bill Gross, “The single biggest reason why startups succeed” (timing as top factor). - Ecosystem context: WordPress plugin repository norms and GPL licensing. ## 🗣️ Paraphrase: 1) Original idea (0%): “At the time… it did not feel like an accomplishment… I thought everybody could do it.” Paraphrase: While running Yoast, the work felt ordinary, even replicable. Only after stepping away did she recognize how exceptional the achievement was. 2) Original idea (50%): “Building a thriving plugin business is superhard… research shows ~40% of success is timing… take experts’ wisdom with a grain of salt.” Paraphrase: Despite real skill involved, external factors—especially timing—carry substantial weight. Therefore, founder advice, including her own, should be treated as situational rather than universal. ## 📰 Newsletter: WordPress builders, ever feel like you’re juggling chainsaws while walking a tightrope? This week, Marieke van de Rakt nails that feeling with a candid reflection on building a plugin business. Open source’s superpower—forkability—also means your best features can be cloned before your coffee cools. Add freemium pressure, compatibility across millions of installs, and a community that side-eyes heavy-handed sales pitches, and you’ve got a masterclass in resilience. Marieke’s take: it’s “madness,” it’s “heroic,” and yes—timing (luck!) matters more than we admit. If you’re learning web dev or shipping your first plugin, this is your reality check and pep talk in one. Pair it with our community highlights, new plugin roundups, and practical tips on sustainable monetization without burning trust. Read: Confidence and Getting Lucky (Post Status). Bonus read: the data on why timing often outruns strategy in startup outcomes. Keep building—thoughtfully, transparently, and with safeguards for support and QA at scale. ## ✅ Action Items: - Map article to your role (Developer Advocate, GoDaddy; OSPO aspirations): - Open-source advocacy: Use this narrative to educate stakeholders on why sustainable funding and contributor support are essential in GPL ecosystems where copying is easy and support burdens are high. - Contributor engagement: Design onboarding that highlights compatibility testing and support triage as core, valued contributions—not just code. - Education: Develop curricula on freemium ethics, community-aligned marketing, and release timing strategies; include case studies from WordPress. - Transparency and inclusivity: Create guidelines for “ethical promotion” that balances revenue with community norms; publish a public playbook for incident response and compatibility stewardship. - OSPO trajectory: Propose an internal framework for plugin lifecycle risk (copy risk, support debt, compatibility matrix) and show how timing analysis informs roadmap bets. - Prompt to evaluate future articles against your goals: - “Analyze how this article addresses open-source sustainability, contributor pathways, and community norms in WordPress. Identify where timing, market dynamics, and licensing shape outcomes. Propose educator-friendly modules, contributor onboarding steps, and OSPO policies that operationalize these insights. Recommend transparent metrics for inclusivity, funding, and governance, aligned with my role as a Developer Advocate and OSPO-director-in-training.” ## 🧪 Hypotheses: - H1: In WordPress, perceived constraints on overt sales messaging reduce short-term conversion but increase long-term brand trust and fork-resistance. - H2: Plugins with structured compatibility testing programs experience lower churn and higher lifetime value despite higher operating costs. - H3: Launch timing relative to core changes (e.g., major WordPress releases) signifi - Summary: Building a successful WordPress plugin business is incredibly challenging due to factors such as open-source competition, conflicts with other plugins, and the delicate balance between making money and maintaining community support. The author reflects on their experience with Yoast and acknowledges that their confidence in their accomplishments came after gaining some distance and perspective. They emphasize the importance of timing in startup success and caution readers to take advice from successful business owners with a grain of salt, as luck also plays a significant role. - URL: https://poststatus.com/confidence-and-getting-lucky/ [Skip to content](https://poststatus.com/confidence-and-getting-lucky/#content) As I have stepped back from Yoast, something happened to me. I’ve given it a name: “confidence after the fact”. At the time when we were running Yoast, coming up with new product ideas, growing that company like crazy, it did not feel like we were doing anything special. It did not feel like an accomplishment. At all. I really thought that everybody could do it. I don’t think that anymore. A little distance has given me a clearer view of the matter. Building a WordPress plugin or product business is super hard. It is the whole open source aspect of it. Everybody can copy every new feature you come up with (and they do!). It is the fact that your paid plugin competes with free plugins. Perhaps with your own free version! It is the reality that if your plugin powers say 2 million sites, it also means that there could be a million conflicts with other plugins. It is madness. And it is heroic if you succeed. You can’t be too salesy as a plugin owner, because you’ll be criticized by our community. And criticism will lead to the risk of your open source plugin being copied by someone else. You’re very vulnerable. At the same time, you *have* to make money, because you’ll need a team in order to secure high-quality code, extensive testing (which you have to do with millions of installs) and support. It is madness. It is heroic. I’m repeating myself. My conclusion: building a thriving plugin business is superhard. So, the fact that we’ve done it with Yoast means that I have earned my confidence afterwards. At the same time: research clearly shows [that about 40% of the success of startups](https://www.ted.com/talks/bill_gross_the_single_biggest_reason_why_start_ups_succeed) (and the biggest predictor with that) is based on timing. I see a lot of successful business owners in and outside of WordPress share their wisdom (on X, on WordCamps, on the web). Same as I am doing in this column. But take everything we so-called experts say with a big grain of salt. We might be very good at what we’ve done (because growing that plugin business IS heroic), but we also just had a lot of luck with our timing!, Confidence and Getting Lucky, Marieke van de Rakt, 01hc52rw7c1et2snvjbdm66jny.