November 14, 2017


This week, Cory speaks to entrepreneur, founder and CEO Matt Mullenweg, who is best known for have founded Automattic, which is behind brands, WooCommerce, Jetpack, Simplenote and more; reaching more than a billion people a month. In this weeks episode, Matt talks about how he got into technology, what his high school and college days were like, being young and in a position within a big company to leaving and risking it all to become a founder, what’s his trick to meet great people to work with or invest in and the great story of how he misplaced a half million check!

At the age of 20, Matt Mullenweg(@photomatt), launched Automattic–the company behind, WooCommerce, Jetpack, and others. Now 33-years-old, Matt is still working at the company he built, helping it change the landscape of websites and blogs throughout the world and give nearly anyone the ability to create and manage their web presence.

In the interview with Cory Levy on OFF RCRD, Matt discusses founding the company and some of its growing pains before he hired now former Automattic CEO Toni Schneider, including losing a $500,000 check from an investor. “Toni had been part of startups for 20 years. He had a ton of experience,” Matt says. “I think something I still learn from him…he can approach things and really connect with people in a way that makes everyone feel really included, and I think it’s one of his superpowers.”

Asked what his superpower is, Matt says “Probably hiring and the non-hiring parts of hiring, which are finding great people to work with. I’ve been very lucky or good at finding great partners within the investment side and other folks I worked work with like Toni.”

Outside of the business, Matt is a musician, and is currently learning a new language (French). For more from Matt Mullenweg, listen to the full OFF RCRD episode here!

 Show Notes
  • 1:07

    How Matt got his start in technology.

  • 2:09

    Why Matt Mullenweg dropped out of college after two years.

  • 4:57

    What he wishes he would’ve done differently in the first year of business at Automattic.

  • 5:42

    What Matt has learned from former Automattic CEO Toni Schneider.

  • 6:33

    Cory asks Matt “What would you say your superpower is?”

  • 7:11

    Matt’s advice to someone moving to San Francisco who doesn’t already have an established network.

  • 8:40

    Matt’s strategy for meeting great people

  • 9:40

    Matt talks about his interests outside of tech

  • 10:00

    MUST LISTEN: Matt shares his most embarrassing moment as an entrepreneur.

  • 12:44

    How Matt overcomes setbacks. “So, knowing that it’s not just you that’s going through a tough time is really helpful”

  • 14:39

    Why Matt talks to friends when making hard decisions.

  • 16:18

    Matt talks about Gutenberg, a new WordPress project that is controversial.

  • 17:31

    How Matt deals with controversy and negative feedback. “ What we try to do is read every single criticism, every single bad review, everything, and extract out what’s really useful from that”

  • 18:38

    “You don’t necessarily need to develop or to make a website.” Hear what Matt’s talking about at and how WordPress websites, and the industry, are changing.

  • 19:25

    Distributed workforce discussion.

  • 21:05

    “One thing I see first-time founders doing wrong is being a little too precious about the idea”.

  • 22:51

    Times when Matt’s family thought he was going crazy.

  • 24:31

    Matt’s routine.

  • 25:12

    Books and blogs Matt recommends.

  • 26:39

    Why Matt is working to figure out marketing for the first time in his company’s history.

  • 29:23

    What Matt is excited about in the world

  • 30:45

    Automattic conducts interviews in a very unique and interesting way. Listen to Matt explain it and why at

  • 33:55

    Cory asks Matt what lessons he’s learned from some of the most influential people in his life, including Tony Hsieh and Tony Conrad.


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