Episode Summary
Executive Summary: Jason Calacanis interviews Matt Mullenweg about angel investing, the evolution of Automattic, open source as a business model, and the future of distributed work. Mullenweg frames investing as pay-it-forward, describes Automattic’s diversified businesses and secondary-friendly private structure, and argues that remote-first, transparent organizations outperform hybrid ones. The conversation also covers moderation, censorship, crypto, and the post-pandemic reshaping of cities and office culture.
Main Topics: Angel investing as pay-it-forward: Mullenweg explains that his early angel and advisory support came from generosity he received as a young founder, so investing became a way to help entrepreneurs and improve sectors he cared about, not just a financial strategy. Automattic’s structure and growth: He outlines Automattic as a holding-company-like platform with consumer subscriptions, enterprise VIP, WooCommerce e-commerce, and Tumblr ads, noting the business can support larger private rounds, secondaries, and potential subsidiary spinouts. Open source as a durable technology advantage: Mullenweg argues that open source consistently disrupts and improves industries, citing WordPress, WooCommerce, Wikipedia, and Bitcoin as examples of open models outperforming closed or centralized systems. Distributed work and the end of the office monoculture: He says remote-first work unlocks flexibility, reduces commuting, exposes underperformance, and can make organizations more efficient; hybrid is hardest, while fully distributed systems with documentation and transparency work best. Moderation, speech, and platform governance: The discussion examines hate speech vs. calls to violence, the difficulty of moderating bots and abuse, the limits of private platform governance, and why government-led frameworks would be preferable if they worked well. Media, objectivity, and editorial rigor: Mullenweg laments the shift from objective reporting to opinion-led content, arguing that blogging helped erode editorial standards, and that writing improves when humans edit and challenge ideas. Personal investing, exits, and crypto: He reflects on winners like Twilio, MakerBot, and Daily Burn, says he now prefers to let winners run, and is bullish on crypto mainly as an open-source technical movement rather than purely speculation.
Key Arguments: Angel investing started as a way to repay the mentors who helped him early in his career and to support founders building ethically and sustainably. Automattic has enough scale and diversification that some subsidiaries could eventually go public independently, without requiring the parent company itself to IPO or do a SPAC. Open source is the common denominator behind the most transformative products in publishing, commerce, knowledge, and finance because it expands control, flexibility, and innovation. Remote-first work is superior to hybrid because it creates equal access to information, forces clearer documentation, and reveals who actually contributes versus who merely appears productive. The biggest moderation challenge online is not speech itself but abuse, bots, coordinated manipulation, and the line between terrible opinions and incitement to violence. Public/private market incentives can distort behavior, especially when platforms are rewarded for inflated user counts, even if those numbers include spam or fake accounts. The pandemic accelerated a workplace shift that was already underway, and the best long-term model may be distributed work with periodic in-person collaboration. Investors should often hold winners longer, as selling too early usually becomes a regret; patience matters more once a company reaches strong network-effect or escape-velocity dynamics.
Data Points: Years working on WordPress: 18 years - Mullenweg describes his long-term commitment to the open-source project. Last interview on the show: 2013 - Calacanis notes prior Angel appearances by Mullenweg. Episode history: Episode 26 in December 2010; episodes 361 and 362 in 2013 - References to earlier appearances on This Week in Startups/Angel. Automattic headcount: about 1,400 people - Used to illustrate company scale and management complexity. Secondary financing raised: $400M–$500M - Mullenweg says Automattic has used large secondaries to reset the clock for early investors. Salesforce investment: $300 million - Strategic investment into Automattic tied largely to enterprise WordPress opportunity. Automattic subsidiary GMV through WooCommerce: $20 billion last year, doubling year over year - Shows the e-commerce business’ scale and growth. Automattic investment sizes: up to $30 million - He notes the company can make larger investments through Automattic rather than personally. Twitter spam estimate: 20%–30% - Mullenweg estimates a significant share of Twitter followers are spam/bots. Pandemic remote-work estimate: 42% remote; 27% still working from home through 2021 - Calacanis cites Upwork data on continuing remote work. Travel volume before lockdown: 500,000 miles per year - Mullenweg describes his pre-pandemic travel intensity. Part-time work options: 80% pay for 80% time; 60% pay for 60% time - Automattic’s flexible employment model introduced during COVID. Current internal documentation system: over 1,000 P2s - Automattic’s internal private blogging system used for transparency and decision history.
Pivotal Quotes: "For me, angel investing was very much a way to get back." — Matt Mullenweg: Explaining why he began investing in startups after being helped by early mentors. "Think of WooCommerce to Shopify, like WordPress is to like Typepad." — Matt Mullenweg: A shorthand comparison for open-source, customizable commerce vs. SaaS commerce. "Hybrid's harder than either extreme." — Matt Mullenweg: Summarizing his view that fully remote or fully in-person systems are easier to manage than mixed models.
Implications: The episode reinforces open source, transparency, and distributed work as durable competitive advantages. It also suggests the next phase of tech may favor flexible, modular companies, stronger moderation frameworks, and post-office-era talent markets.
About This Week in Startups
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.