Matt Mullenweg: Characteristics and Practices of Successful Entrepreneurs (#190)

Photo credit: Aminul Islam Sajib

“If someone has those four things — work ethic, taste, integrity, and curiosity — I believe that you can learn anything in the world.” – Matt Mullenweg

Matt Mullenweg (@photomatt) is most associated with a tool that powers more than 25% of the entire Web: WordPress. He’s also the CEO of Automattic, which is a multi-billion dollar, fully distributed startup. Matt loves tea, tequila, and Chicken McNuggets.

His first time on the show went over so well that you’ve all been asking for a round two. So in this episode, he answers your most popular questions.

If you only have 5 minutes, you’ll want to hear Matt’s thoughts on the factors (other than hard work) most likely to lead to a successful career.

Please enjoy!

#190: Matt Mullenweg on the Characteristics and Practices of Successful Entrepreneurs

Want to hear another interview with Matt Mullenweg? — Listen to his first appearance on the podcast. In this episode, we discuss polyphasic sleep, tequila, and building billion-dollar companies (stream below or right-click here to download):

Ep 61: The Benevolent Dictator of the Internet, Matt Mullenweg

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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

Selected Links from the Episode

  • Connect with Matt:

Twitter | Blog | Facebook | Spotify

Show Notes

  • Matt talks about what happened with WordPress and Automattic since his last tequila-fueled appearance on the show. [05:50]
  • What’s the hardest part about running a company with a distributed workforce? [06:43]
  • Matt’s seasoned tips for frequent travelers. [11:43]
  • Professional and personal advice Matt would give his younger self. [14:28]
  • What’s the most important skillset for an entrepreneur to develop? [18:12]
  • What non-technical characteristics does Matt look for when recruiting new employees? [20:24]
  • If WordPress is the platform of writing, and Shopify is the platform of commerce, what other platforms are worth developing? [22:39]
  • Matt talks about the toughest thing he deals with day-to-day. [26:36]
  • Once-important default settings (values or behaviors) Matt has since questioned and removed. [28:03]
  • What factors — aside from hard work — does Matt believe contribute significantly to success? [32:54]
  • Matt talks about failure and how even the big names don’t always get it right. [33:50]
  • What final food and drink is appropriate for greeting the apocalypse? [35:42]
  • Matt’s thoughts on so-called “artificial intelligence” web developer/designer tools — and if WordPress might utilize something like these in future. [39:40]
  • Matt on machine learning and deep learning. [45:25]
  • What would the next six months of Matt’s life look like if he’d been less successful thus far and had to start with nothing? [46:31]
  • How would Matt gauge hype cycles for what’s in demand if he were trying to start a new business today? [49:40]
  • Where does Matt see the future of the Internet in terms of user behavior? [52:05]
  • Is the demand for Web development still high, or is it stagnating? [56:18]
  • How does Matt motivate himself? [59:18]
  • How has Matt solved his biggest technical problems? [1:02:19]
  • What is Matt’s evening routine (if he has one)? [1:05:55]
  • Matt’s morning routine? [1:07:45]

People Mentioned

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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33 Replies to “Matt Mullenweg: Characteristics and Practices of Successful Entrepreneurs (#190)”

  1. Excellent points on hiring. It’s definitely not my superpower. I would love to know more about how Matt screens for “taste.”

    A side note to Tim: I’ve been scanning your podcasts and see dude after dude after dude. It makes me sad. There are countless extremely competent, clever, and accomplished women leaders out there. They might not promote themselves as aggressively, but I’ve found in my professional life (science) that there’s virtually no correlation between self-promotional skill and deeper talents, which are often directed to less egotistical ends.

    1. Perhaps a woman should podcast these competent and highly accomplished women. Tim is very good at talking with/interviewing world class male ‘performers’. I don’t know if he chose that male path instinctively or not. Perhaps it is his superpower to analyze and talk with men, and not to women, who knows? For me it is working, but why not ask it himself?

      Matt Mullenweg talked before about how he screens for taste, I believe it had to do something with jazz (or is my brain just making that up?) and he also said somewhere that it’s something you have or not, you can’ t teach that (or something along that line).

      With kind regards,

      Kyung Munneke

      1. All the dudes you interview are GREAT. I love your work. If you aren’t interviewing women it might be because you haven’t found women that inspire you enough. Or because you are mostly passionate about manly things. Whatever the reason is I think this female ‘black hole’ in your ‘Ferrissphere’ is great; if you frustrate enough women, maybe one of them will model you and become a ‘female version’ of Tim Ferriss (blog, books and podcasts…nothing look-related lol). Cheers to you and all the manly man out there – a successful woman, tsunami survivor, artist, former ss3 candidate on TF1

      2. Beyond the gender of the people you interview, what makes your podcasts attractive is the feminine softness, sweetness and calm that you sprinkle over your rather masculine subjects. There is always great humour, humility and lightness of heart (sometimes light-headedness lol). A female or a male interviewee ? I don’t really care. Caring would imply some sort of sexism. As long as the exchange is genuine, honest and sweet.

  2. I really enjoyed listening to this – thank you! These two points really resonated with me:

    “it is so easy to just be lost minute to minute, and be busy all day and not really bring yourself closer to the mountain that you want to climb.”

    That was fabulous. I’ve really been feeling like that lately. It felt like you were totally pulling the feeling from my mind.

    I also liked this sentiment:

    “there’s probably someone you admire who’s also having a bad day right this second”

    I totally gawked when you said you had 600 applications in the queue to review. Mine is buried in there somewhere! Hah.

  3. Hi Tim, I very much enjoy your podcasts. This one was “fucking interesting” as well. I heard near the last 40 minutes, both your and Matt’s comments about running. He has interest, but struggles with pain when running. For you, you can take it, or leave it, but generally choose a cruiser bike around town, or exercise according to your objectives. I love to run and also teach individuals on how to run with great form, while learning to love it. If you are ever in St. George, Utah for some crazy reason, or have interest in meeting somewhere for a tutorial, I would be honored to take you, and/or Matt on a run. I am also a yoga and a cyclist. I incorporate lessons from yoga into how I run and ride my bike. You just might be intrigued by my way of it. Regardless, I enjoy the way you reach out to the world. Thank you for your fearless (or at least outward so) ability to share yourself in the raw.

  4. Unsexy…forms aren’t sexy? Maybe not but we made it look pretty cool in our humble opinion with this philanthropy 😉

  5. Hi Tim, Love your podcasts. Very inspiring and has really been a benefit to me. I’m hoping that you include more women. It seems like you are very male-centric in your guest choices. Is this intentional? Much love.

    p.s. I was about to post this and just saw a previous post on the same topic.

    1. I have quite a few incredible women in the pipeline, so fingers crossed that they happen.

      In general, I interview the people my fans most request, or people I come across in person. Plenty of incredible women interest me, but most have proven harder to reach than their male counterparts. Not sure why that is. In any case, my audience is 87% male, last I polled, so it makes sense that most requests would be for males.

      Suffice to say, I think people should focus on lessons they can learn from any given person, not that person’s gender. That’s an expensive mistake.



  6. Tim, as always, amazing content!

    Keeping up with the podcast is a way of reminding myself of topics I wish to think about, but if not for the podcast, might not. It guides my thoughts into productive areas, good questions, for my business and personal life. To have some routines where I am constantly being reminded of good topics, like the ones brought through your interviews, has made my life way better.

    I can´t thank you enough.

  7. Thank you for putting up this podcast with Matt! I do have to say, I *really* miss your participation in the conversational format.

  8. Tim , I have followed you closely since 2007 . Please interview Andy Puddcombe . Please if you are struggling with depression aviod all alcohal . Please get back to the core of your original message . Interruptions . Get back to your core message of truly only letting what matters most enter our lives .

    Don’t contiue to feed your insecurities by making sure your audence is growing . Get back to the core message of giving us the tools to create . 1) income )2) time ) 3 mobility . And for the love of God stop being a pussy and ask Amelia Boone out , your fan

  9. Hey guys

    Really enjoyed the podcast, as usual, and my one question was: What one thing would you change about the way you work now? You know, what is hindering you that you wish didn’t!

    Thanks guys

    Antony Hammond

  10. Tim,

    I’m going to keep this quick. You have been an inspiration for the past 2 years.

    I am in a predicament. I need help in bettering workplace happiness at my company. My company, who services 5,000 hospitals, specializes in health care supplies and we’ve had high employee turnover. I am an owner, at age 24, and I know you could point me in the right direction.



  11. Great talk Matt! Any more details on the Blicki, curated wiki you mentioned that you were working on? It would be great for knowledge sharing on the web.

  12. I just listened to the first podcast recently and then out comes this new one – awesome! Matt is a very inspiring guy who makes you recognise the possibilities and think differently. That and I’ve been a WordPress developer for quite a long time now and its definitely not going anywhere! WordPress is hugely capable for many applications not just blogs. Matt’s focus on nurturing his networks and being respectful comes across strongly. One of my favourite podcasts. Please interview more tech BDFLs. How about the founder of Drupal Dries Buytaert (just to be controversial) 😛

  13. Matt,

    My blood pressure drops when I listen to you. This podcast felt like a guided meditation. You’re calm, humble and thoughtful. I agree, character is about growing one’s soul, integrity, curiosity, and empathy.

    Thank you for sharing.

  14. So good to have Matt back, and kudos to the community on some great Qs. The “four attributes” in hiring, you sharing your morning routine and frank thoughts on evening routine. And to just get the sense of the techniques you have made routine and where serendipity rules (evening wind-down!), the provocation to reflect on greater questions. I only missed hearing a bit more about your musician days, and the influence of jazz on your life…being a tenor player!

    Ps. Great radio voice and tempo, Matt…

    1. P.S. Also – “Luck” as your first instinctual answer to what has been behind your success. For me, this is always such an immense signal of true character, it sent shivers down my spine!

  15. I wanted to see how Neil Postman’s book Amusing Ourselves to Death came up. It is a great book. A must-read. He also talked about some good books in his first podcast here. Mr. Mullenweg has so much class. This episode must be in top ten here (among the guest episodes) in terms of practical advise and quality.

    Best x

  16. Matt – I think your WordPress dashboard could need a designer/PM to improve UX. It is a feature-rich dashboard, but not one that is necessarily intuitive to a new user – particularly bloggers who are not tech-savvy. Also – the choice is overwhelming for someone who’s only looking for best practices.

  17. Safe, predictable track vs. Risk-taking, experiential path…..

    I have always subscribed to the former, to maintain a tight leash on my plans and goals. Keep things in a box, instead of having a whole world of opportunity, seemingly without direction. But I have always had a creative and exciting mind. So, now I am experimenting with the wander and exploring potential opportunities, leading to a feeling of overwhelming, lack of control, lack of purpose, and lack of prospect.

    How are these “fly by the seat of your pants” feelings handled, in someone who functions best within a very solid plan and path?

    Thank you.