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January 31, 2025 • 46min
I was offered $200M at 24 and I turned it down
My First Million
Matt Mullenweg, founder of WordPress and CEO of Automattic, joins Sam Parr and Shaan Puri to discuss building one of the internet's most widely-used platforms. The conversation covers WordPress's early days, key business decisions, company culture, recent industry drama, and thoughts on emerging technologies like AI.
I was offered $200M at 24 and I turned it down
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Key Takeaways
- WordPress Origin & Growth: Started in 2003 by Matt Mullenweg at age 19, WordPress now powers over 43% of websites on the internet
- Early Days: Had "1000 days of irrelevance" before gaining significant traction - success wasn't overnight
- Major Decision: Turned down $200M acquisition offer at age 24 to maintain independence and build something bigger
- Business Model: Automattic (parent company) generates $500M+ in revenue while capturing only ~5% of the total WordPress ecosystem value
- Company Culture: Innovative hiring practices including text-based interviews, paid trial projects, and requiring all employees to do customer support
- Philosophy: Strong commitment to open source software and increasing freedom/liberty in the world through technology
Introduction
Matt Mullenweg, founder of WordPress and CEO of Automattic, joins Sam Parr and Shaan Puri to discuss building one of the internet's most widely-used platforms. The conversation covers WordPress's early days, key business decisions, company culture, recent industry drama, and thoughts on emerging technologies like AI.
Topics Discussed
The $200M Decision Point (0:44)
In 2008, at age 24, Mullenweg faced a pivotal decision when offered $200M to acquire WordPress/Automattic:
- Company had only raised $1M at a $3M valuation previously
- Instead of selling, converted the offer into a funding round valuation
- Investors supported building something bigger vs. taking early exit
- Used some proceeds for personal liquidity to remove financial stress
WordPress's Early Days (5:38)
The platform's growth wasn't immediate despite appearing as an "overnight success":
- Humble Beginnings: Started by manually setting up blogs for high school friends
- Community Building: Hosted "upgrade parties" at apartment to help users update WordPress
- "What people see as overnight success is often a thousand days of irrelevance" - Matt Mullenweg
- Early focus on building community and improving the core product
Business Model & Monetization (6:46)
Discussion of WordPress's unique approach to capturing value:
- Ecosystem Value: Total WordPress ecosystem generates ~$10B annually
- Revenue Split: Automattic captures only about 5% ($500M+) of total ecosystem value
- Compared to proprietary platforms that capture much more value percentage-wise
- "WordPress is almost like the dark matter of the web" - Matt Mullenweg
WooCommerce Acquisition Success (9:24)
One of Automattic's most successful acquisitions:
- Originally a small South African company with 40 employees
- Combined Automattic's engineering expertise with WooCommerce's product-market fit
- Now processes over $30B in annual transactions
- Competes with Shopify while maintaining open-source philosophy
Open Source vs. Proprietary Software (13:40)
Discussion of business model trade-offs:
- Short-term vs. Long-term: Proprietary models easier to monetize initially
- Freedom & Liberty: Open source provides users more control and rights
- Open source creates "flywheel effect" of community adoption and innovation
- "I want all my creative output to increase the amount of freedom and liberty in the world" - Matt Mullenweg
Recent Industry Drama (18:37)
Addressing recent controversy with WP Engine:
- Concerns over trademark confusion and ecosystem contributions
- Private equity ownership changing company dynamics
- Need to protect open source principles and community
- Legal battle ongoing but expected to resolve in coming months
Innovative Hiring Practices (30:07)
Automattic's unique approach to hiring and evaluation:
- Trial Projects: Paid contract work instead of traditional interviews
- Text-based Communication: Many roles hired purely through written interaction
- Focus on finding overlooked talent that might not fit traditional tech hiring
- Equal pay globally regardless of employee location
Customer Support Philosophy (36:04)
Universal customer support requirement for all employees:
- First two weeks of any role spent doing customer support
- Annual rotation back to support for one week
- Helps maintain connection to customers and product understanding
- Provides insights for product improvement and company culture
Thoughts on AI & Deepseek (42:56)
Perspective on recent AI developments:
- Appreciates Deepseek's open source approach and transparency
- Encourages hands-on experimentation with different AI models
- Values ability to run models locally vs. relying on hosted services
- Sees potential in combining open source principles with AI advancement
Conclusion
The conversation with Matt Mullenweg reveals a leader deeply committed to open source principles while building a successful business. His approach to company building - from innovative hiring practices to universal customer support requirements - demonstrates how alternative models can work at scale. The discussion highlights how maintaining strong principles while adapting to market realities has allowed WordPress to become a dominant force in web publishing while staying true to its original mission of increasing freedom and liberty through technology.