Lessons in longevity: How Matt Mullenweg scaled Automattic to $500M+ (and what's next)

This week, we're running it back to one of our most popular episodes. Recorded live at SaaStock USA 2023, host Alex Theuma is joined by Jason Cohen, Founder of WP Engine. In the episode, Jason reflects on his multi-decade journey as a serial entrepreneur, and shares his lessons from building and scaling WP Engine into a SaaS giant, including: - His journey as a serial entrepreneur. - The science behind why your startup really is like your baby. - Founding WP Engine, the world’s largest managed Wordpress platform - From bootstrapped to venture backed, the decision to raise money. - Why most founders shouldn’t raise money—and how to know if you’re one of them. - How to build a practical strategy that involves the whole team. - How to know your own strengths and why he replaced himself as CEO. Guest links: LinkedIn: https://www.linkedin.com/in/jasoncohen/ WP Engine: https://wpengine.com/Check out the other ways SaaStock is helping SaaS founders move their business forward: 🇺🇸 SaaStock USA 2025: 13-15 May 2025 | Austin, Texas. Connect, learn and thrive at the leading conference for B2B SaaS Founders, Operators and Investors from Pre-Seed to Series C. https://saastock-usa.com/tickets/ 🇮🇪 SaaStock Europe 2025: 12-14 October 2025 | Dublin, Ireland. "The best SaaS conference for founders, execs & investors in Europe, period." - Christoph Janz, Partner, Point Nine. https://saastock-europe.com/tickets/ 🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/) 🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)