Episode Summary
Executive Summary: In this episode of Angel, Jason Calacanis interviews Matt Mullenweg, co-founder of WordPress and CEO of Automattic. They discuss Mullenweg's journey from a young developer to a superangel investor, the evolution of Automattic (including its subsidiaries like WooCommerce and Tumblr), the challenges of remote work, the impact of the pandemic on work culture, and the future of San Francisco. Mullenweg shares insights on open source, investing philosophy, and the importance of documentation and transparency in distributed teams.
Main Topics: Matt Mullenweg's Journey and Investing Philosophy (Priority: 5/5): Mullenweg discusses his transition from a young developer to a superangel investor, emphasizing that early angel investing was more about paying it forward and supporting the ecosystem than making returns. He notes that he still views investing partly as a charitable act. Automattic's Structure and Future (Priority: 5/5): Mullenweg explains Automattic's structure as a holding company with subsidiaries like WordPress.com, WooCommerce, VIP, and Tumblr. He discusses the possibility of spinning off some subsidiaries as public companies, similar to IAC, and the company's growth trajectory. Remote Work and Distributed Teams (Priority: 4/5): Mullenweg shares his pioneering experience with remote work at Automattic, the challenges of hybrid models, and the importance of documentation and transparency. He advocates for distributed work and discusses the podcast 'The Distributed Podcast'. The Future of San Francisco and Tech Hubs (Priority: 3/5): The conversation covers the decline of San Francisco as a tech hub due to high costs and the pandemic, and the rise of other cities like Austin and Miami. Mullenweg predicts that market forces will lower prices and bring diversity back to the city. Content Moderation and Free Speech (Priority: 4/5): Mullenweg discusses the challenges of content moderation, the balance between free speech and preventing violence, and the role of platforms like WordPress in hosting controversial content. He emphasizes the importance of pseudonymous speech and the difficulty of combating abuse. Crypto and Open Source (Priority: 3/5): Mullenweg expresses bullishness on Bitcoin and Ethereum from a technical perspective, highlighting the open-source nature of these technologies. He discusses the potential of decentralized systems but notes the challenges of bad actors and the need for regulation.
Key Arguments: Angel investing should be viewed as a way to pay it forward and support the ecosystem, not just for financial returns. Hybrid remote work is harder than fully remote or fully in-person; documentation and transparency are key to making it work. Open source principles can disrupt industries like finance (Bitcoin) and e-commerce (WooCommerce), similar to how WordPress disrupted CMS. Content moderation is a complex problem; platforms should focus on calls to violence rather than hate speech, and defer to legal systems. The pandemic has accelerated the shift to remote work, and companies that invest in real estate may need to repurpose it for housing or collaborative spaces. Founders should prioritize building a sustainable business early, hiring and firing carefully, and setting a strong example of work ethic and integrity.
Data Points: Automattic employees: 1,400 - Current size of Automattic, the company Mullenweg leads. WooCommerce GMV: $20 billion - Gross merchandise value processed through WooCommerce in the past year, doubling year over year. Automattic secondary raises: $400-500 million - Amount raised in secondary offerings to allow early investors to exit. Automattic investment from Salesforce: $300 million - Investment from Salesforce about 18 months ago, focused on enterprise opportunities. Bitcoin price increase: 470x - Mullenweg's wife bought Bitcoin at under $100; current price around $47,000. American workforce working remotely: 42% - Percentage of the American workforce continuing to work remotely, according to Upwork. Estimated remote workforce in 2021: 27% - Projected percentage of workers still working from home through 2021. Automattic hiring in 2021: 400 people - Number of new hires planned for the year.
Pivotal Quotes: "I still think of it that way, largely. We do make some larger. So today, again, my primary gig is I'm the CEO of a company called Automatic, which is about 1400 people now. And that is, that takes really all of my time. My volunteer gig is running the WordPress.org open source project. So angel investing kind of fits in between the cracks there." — Matt Mullenweg: Mullenweg explaining his view of angel investing as partly charitable and how it fits into his busy schedule. "Hybrid's harder than either extreme. So, if you think of like all in person over here, hybrid in the middle, and all remote here, the hybrid is the hardest one to do, right?" — Matt Mullenweg: Mullenweg discussing the challenges of hybrid work models compared to fully remote or fully in-person. "I think it's a good place for, for as friends, to hold each other accountable. Like, if we're not changing our mind on certain things over time, then we're not learning." — Matt Mullenweg: Mullenweg reflecting on the importance of changing one's mind based on new evidence, in response to Calacanis's changed views on solitary confinement and the death penalty.
Implications: This episode underscores the enduring value of open source and remote work, the complexity of content moderation, and the need for founders to build sustainable businesses. It also highlights the shifting geography of tech hubs and the importance of adaptability in investing and company culture.
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.