StarZero All shows Try the podcast clipper →

Mar 24, 2022 · 59m · startup-ideas

How to Engineer Serendipity | Matt Mullenweg, Automattic

Sahil Bloom · 29m spoken Greg Isenberg · 11m spoken Matt Mullenweg · 10m spoken
0:00 / 0:00
▶ Watch on YouTube →

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Hosts Sahil Bloom and Greg Isenberg analyze strategic career frameworks, geopolitical developments, and Web3 trends before interviewing Automattic CEO Matt Mullenweg on distributed leadership, asynchronous work, and manufacturing career serendipity.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Greg holds 22.7% of the talking time here. How this is scored →

Greg as informed peer 3.3 Guest teaching 1.8 Guest disagreement 1.0 Greg pushing back 1.0
05100:0015:0030:0045:002:12–8:04 · Greg as informed peer 4/10 High Yield Careers and the Reality of Mailbox Money Greg and Sahil discuss treating traditional high-paying jobs as high-yield holding positions while building side ventures. Greg shares his personal experience setting up recurring affiliate income to fund future projects.8:08–15:03 · Greg as informed peer 4/10 Crypto Aid in Ukraine and Corporate Exits from Russia The hosts analyze crypto donations to Ukraine and how it reframes the public perception of web3 technology away from criminal stereotypes. They also discuss tech company departures from Russia.15:05–27:06 · Greg as informed peer 5/10 Critiquing Tai Lopez's Controversial NFT Project Greg critiques Tai Lopez's expensive NFT collection by comparing its over-inflated supply to successful boutique token models. Sahil notes the importance of the web3 community self-policing cash grabs.27:07–29:13 · Greg as informed peer 0/10 Sponsor Message: Lex Real Estate Investing (Reprise) Mid-roll commercial sponsor messaging for Lex real estate investing and Outer outdoor furniture.29:14–32:24 · Greg as informed peer 3/10 Setting the Stage: Matt Mullenweg and the Future of Work The co-hosts set the context for the interview with Matt Mullenweg by reviewing his Wall Street Journal feature and the ongoing debate surrounding return-to-office mandates.32:24–59:06 · Greg as informed peer 4/10 Matt Mullenweg on Asynchronous Work, Serendipity, and Leadership Matt Mullenweg explains how Automattic scales fully remote work, advocates for equal global compensation regardless of geography, and outlines why writing in public creates superior serendipity. Greg shares his history of meeting Matt at a jazz festival.2:12–8:04 · Guest teaching 2/10 High Yield Careers and the Reality of Mailbox Money Greg and Sahil discuss treating traditional high-paying jobs as high-yield holding positions while building side ventures. Greg shares his personal experience setting up recurring affiliate income to fund future projects.8:08–15:03 · Guest teaching 1/10 Crypto Aid in Ukraine and Corporate Exits from Russia The hosts analyze crypto donations to Ukraine and how it reframes the public perception of web3 technology away from criminal stereotypes. They also discuss tech company departures from Russia.15:05–27:06 · Guest teaching 2/10 Critiquing Tai Lopez's Controversial NFT Project Greg critiques Tai Lopez's expensive NFT collection by comparing its over-inflated supply to successful boutique token models. Sahil notes the importance of the web3 community self-policing cash grabs.27:07–29:13 · Guest teaching 0/10 Sponsor Message: Lex Real Estate Investing (Reprise) Mid-roll commercial sponsor messaging for Lex real estate investing and Outer outdoor furniture.29:14–32:24 · Guest teaching 0/10 Setting the Stage: Matt Mullenweg and the Future of Work The co-hosts set the context for the interview with Matt Mullenweg by reviewing his Wall Street Journal feature and the ongoing debate surrounding return-to-office mandates.32:24–59:06 · Guest teaching 6/10 Matt Mullenweg on Asynchronous Work, Serendipity, and Leadership Matt Mullenweg explains how Automattic scales fully remote work, advocates for equal global compensation regardless of geography, and outlines why writing in public creates superior serendipity. Greg shares his history of meeting Matt at a jazz festival.2:12–8:04 · Guest disagreement 1/10 High Yield Careers and the Reality of Mailbox Money Greg and Sahil discuss treating traditional high-paying jobs as high-yield holding positions while building side ventures. Greg shares his personal experience setting up recurring affiliate income to fund future projects.8:08–15:03 · Guest disagreement 1/10 Crypto Aid in Ukraine and Corporate Exits from Russia The hosts analyze crypto donations to Ukraine and how it reframes the public perception of web3 technology away from criminal stereotypes. They also discuss tech company departures from Russia.15:05–27:06 · Guest disagreement 2/10 Critiquing Tai Lopez's Controversial NFT Project Greg critiques Tai Lopez's expensive NFT collection by comparing its over-inflated supply to successful boutique token models. Sahil notes the importance of the web3 community self-policing cash grabs.27:07–29:13 · Guest disagreement 0/10 Sponsor Message: Lex Real Estate Investing (Reprise) Mid-roll commercial sponsor messaging for Lex real estate investing and Outer outdoor furniture.29:14–32:24 · Guest disagreement 0/10 Setting the Stage: Matt Mullenweg and the Future of Work The co-hosts set the context for the interview with Matt Mullenweg by reviewing his Wall Street Journal feature and the ongoing debate surrounding return-to-office mandates.32:24–59:06 · Guest disagreement 2/10 Matt Mullenweg on Asynchronous Work, Serendipity, and Leadership Matt Mullenweg explains how Automattic scales fully remote work, advocates for equal global compensation regardless of geography, and outlines why writing in public creates superior serendipity. Greg shares his history of meeting Matt at a jazz festival.2:12–8:04 · Greg pushing back 1/10 High Yield Careers and the Reality of Mailbox Money Greg and Sahil discuss treating traditional high-paying jobs as high-yield holding positions while building side ventures. Greg shares his personal experience setting up recurring affiliate income to fund future projects.8:08–15:03 · Greg pushing back 1/10 Crypto Aid in Ukraine and Corporate Exits from Russia The hosts analyze crypto donations to Ukraine and how it reframes the public perception of web3 technology away from criminal stereotypes. They also discuss tech company departures from Russia.15:05–27:06 · Greg pushing back 2/10 Critiquing Tai Lopez's Controversial NFT Project Greg critiques Tai Lopez's expensive NFT collection by comparing its over-inflated supply to successful boutique token models. Sahil notes the importance of the web3 community self-policing cash grabs.27:07–29:13 · Greg pushing back 0/10 Sponsor Message: Lex Real Estate Investing (Reprise) Mid-roll commercial sponsor messaging for Lex real estate investing and Outer outdoor furniture.29:14–32:24 · Greg pushing back 0/10 Setting the Stage: Matt Mullenweg and the Future of Work The co-hosts set the context for the interview with Matt Mullenweg by reviewing his Wall Street Journal feature and the ongoing debate surrounding return-to-office mandates.32:24–59:06 · Greg pushing back 2/10 Matt Mullenweg on Asynchronous Work, Serendipity, and Leadership Matt Mullenweg explains how Automattic scales fully remote work, advocates for equal global compensation regardless of geography, and outlines why writing in public creates superior serendipity. Greg shares his history of meeting Matt at a jazz festival.

speaking balance: gold is Greg, purple is the guest (3 minute bins)

0:00 · Greg 3.3% · guest 96.7%0:00 · Greg 3.3% · guest 96.7%3:00 · Greg 26.5% · guest 73.5%3:00 · Greg 26.5% · guest 73.5%6:00 · Greg 22.2% · guest 77.8%6:00 · Greg 22.2% · guest 77.8%9:00 · Greg 34.5% · guest 65.5%9:00 · Greg 34.5% · guest 65.5%12:00 · Greg 21.9% · guest 78.1%12:00 · Greg 21.9% · guest 78.1%15:00 · Greg 57.4% · guest 42.6%15:00 · Greg 57.4% · guest 42.6%18:00 · Greg 50.4% · guest 49.6%18:00 · Greg 50.4% · guest 49.6%21:00 · Greg 40.7% · guest 59.3%21:00 · Greg 40.7% · guest 59.3%24:00 · Greg 28.2% · guest 71.8%24:00 · Greg 28.2% · guest 71.8%27:00 · Greg 1.2% · guest 98.8%27:00 · Greg 1.2% · guest 98.8%30:00 · Greg 28.5% · guest 71.5%30:00 · Greg 28.5% · guest 71.5%33:00 · Greg 9.4% · guest 90.6%33:00 · Greg 9.4% · guest 90.6%36:00 · Greg 0% · guest 100%36:00 · Greg 0% · guest 100%39:00 · Greg 62.7% · guest 37.3%39:00 · Greg 62.7% · guest 37.3%42:00 · Greg 0% · guest 100%42:00 · Greg 0% · guest 100%45:00 · Greg 6.7% · guest 93.3%45:00 · Greg 6.7% · guest 93.3%48:00 · Greg 26% · guest 74%48:00 · Greg 26% · guest 74%51:00 · Greg 3.8% · guest 96.2%51:00 · Greg 3.8% · guest 96.2%54:00 · Greg 27.4% · guest 72.6%54:00 · Greg 27.4% · guest 72.6%57:00 · Greg 0% · guest 100%57:00 · Greg 0% · guest 100%
Sharpest disagreement ▶ 38:17 Matt Mullenweg dismisses physical proximity as the source of serendipity

Matt politely reframes the assumption that physical cities like SF hold a monopoly on chance encounters, pointing out that intellectual debates migrated online years ago.

 Hardest push from Greg ▶ 48:02 Greg pushes back against US-centric anti-remote narratives

Greg rejects the assumption in Keith Rabois's anti-remote post, pointing out that demanding in-person presence excludes global talent in places like Nigeria, Kenya, and India.

 Biggest teaching moment ▶ 49:53 Matt explains equalizing global pay to capture top international talent

Matt educates the hosts on how paying top global compensation regardless of location lets Automattic outcompete US-bound companies for the best minds worldwide.

 Greg holds their own ▶ 25:15 Greg breaks down web3 community token mechanics

Greg demonstrates operational expertise in community building by contrasting Tai Lopez's oversized mint with the tighter, high-touch 300-member model of Crypto Packaged Goods.
the scores for every segment, with the reasoning behind each
ChapterTopicGreg as informed peerGuest teachingGuest disagreementGreg pushing backWhy
High Yield Careers and the Reality of Mailbox Money 4211 Greg and Sahil discuss treating traditional high-paying jobs as high-yield holding positions while building side ventures. Greg shares his personal experience setting up recurring affiliate income to fund future projects.
Crypto Aid in Ukraine and Corporate Exits from Russia 4111 The hosts analyze crypto donations to Ukraine and how it reframes the public perception of web3 technology away from criminal stereotypes. They also discuss tech company departures from Russia.
Critiquing Tai Lopez's Controversial NFT Project 5222 Greg critiques Tai Lopez's expensive NFT collection by comparing its over-inflated supply to successful boutique token models. Sahil notes the importance of the web3 community self-policing cash grabs.
Sponsor Message: Lex Real Estate Investing (Reprise) 0000 Mid-roll commercial sponsor messaging for Lex real estate investing and Outer outdoor furniture.
Setting the Stage: Matt Mullenweg and the Future of Work 3000 The co-hosts set the context for the interview with Matt Mullenweg by reviewing his Wall Street Journal feature and the ongoing debate surrounding return-to-office mandates.
Matt Mullenweg on Asynchronous Work, Serendipity, and Leadership 4622 Matt Mullenweg explains how Automattic scales fully remote work, advocates for equal global compensation regardless of geography, and outlines why writing in public creates superior serendipity. Greg shares his history of meeting Matt at a jazz festival.

Statements from this episode (10)

Insight
Bloom: Treat Steady Corporate Jobs as High-Yield Accounts for Asymmetric Opportunities
“It's like you as a human being, imagine yourself as like a pile of cash, like a million dollars of cash. You're just a pile of cash. And it's not always that you find the like perfect thing to invest that cash in, like to invest your resources in. And so somet…”
Sahil Bloom Mar 24, 2022 ▶ 3:35
What-if
Isenberg: Tai Lopez NFT would succeed better with 300 mints
“If I was Tai Lopez, I wouldn't have created such a big collection. I think it's like 8600 or something like that. And I would have just focused on like 300. People like his odds of success would have been way higher higher if he just would have taken the club …”
Greg Isenberg Mar 24, 2022 ▶ 25:15
Assertion Supported
Mullenweg: WordPress co-founders had never met in person when starting project
“Myself and the co-founder had never met in person. He was in the UK. I was in Houston, Texas, where I am today.”
Matt Mullenweg Mar 24, 2022 ▶ 34:17
Insight
Mullenweg: Competing for SF Talent Was Fishing in a Small Pond
“Like I'm a big believer in in-person and physical space. A big part of automatic culture is actually meetups where we would bring either the whole company or teams together a few times a year. But it just felt like the best, most talent in the world was not in…”
Matt Mullenweg Mar 24, 2022 ▶ 36:45
Opinion
Mullenweg: Marc and Ben's public writing disrupted the VC model for a16z
“What would Andreessen Horowitz be without Mark's seminal essays and Ben's amazing books and essays, you know, like Their writing is part of how they disrupted the VC model and became Andres and Horowitz, which now we take for granted.”
Matt Mullenweg Mar 24, 2022 ▶ 45:46
Disclosure
Mullenweg: Automattic pays identical salaries regardless of employee geography
“So something we didn't do when we started, but we switched in like, was paying the same salaries regardless of geography, right? It's the same work. It's the same job. You're creating the same value for the company and the and the customers. So you should make…”
Matt Mullenweg Mar 24, 2022 ▶ 49:57
Assertion Not checkable as stated
Mullenweg: Automattic is at 2,000 employees and hired 700 last year
“You know, we're 2000 people now. We hired 700 last year, by the way, so you can scale this quite a bit.”
Matt Mullenweg Mar 24, 2022 ▶ 53:24
Insight
Mullenweg: Team time zone differences should not exceed seven to eight hours
“I think for teams, it's good to be in a range. I'm actually okay with a range of up to seven or eight hours, so like Europe and US is okay, because you can still overlap for an hour to a day, and that's usually plenty. If you need a lot more, you're probably h…”
Matt Mullenweg Mar 24, 2022 ▶ 54:23
Assertion Not checkable as stated
Mullenweg: 55% of Tumblr users are under 24 and 85% on mobile
“It is majority. So 55% under 24 and under. So it's a young blogging network, which is neat. It's different than WordPress's demographics. It's primarily mobile. 85% of mobile. It's still doing tens of thousands of signups per day.”
Matt Mullenweg Mar 24, 2022 ▶ 56:16
Disclosure
Mullenweg: I Personally Took Over as Tumblr CEO in February 2022
“And actually, you know, some news as of February first, I'm running it personally. So I'm day to day running Tumblr as CEO working on the product, working on the design, working on the tech, working on everything.”
Matt Mullenweg Mar 24, 2022 ▶ 56:45
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 300 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more