Hiring For Distributed Companies & Angel Investing: This Week in Startups with Jason Calacanis

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“Why would the best employees in the world choose so little autonomy in the third of their day or more that they spend working?” Matt Mullenweg asks Jason Calacanis in a recent appearance on the long-running This Week In Startups.

The angel investing-themed episode opens with both investors sharing their approaches to early-stage companies, supporting entrepreneurs, and making an ecosystem-building impact, on top of return-on-investment.

The conversation soon shifts toward the outlook for distributed work. “What do you think the world’s going to look like in six months when everybody’s got their shots and is back to work, in at least the United States and Europe?” Jason asks. Matt shares a hiring insight for distributed, global companies, from the changing perspective of a talented individual who can now work from many more places: “You can really build a robust social network with folks you choose to connect with…(anything) that gives you that sense of community, not just where you happen to work.”

Matt’s latest appearance on the show – he first appeared on Episode 26 in 2010, according to Jason, and again in 2013 – touches on Automattic’s business structure, using collaboration tools like P2 to onboard new employees, cryptocurrency, and the value of editors. “I haven’t met a single writer – or any of my own writing – that hasn’t been vastly improved by really great editing,” says Matt. “Engaging your ideas with another human just improves them every single time.”

You can listen to the full This Week in Startups episode here, or check out the YouTube channel.

Getting Legal Work Done in a Distributed Environment: Paul Sieminski with Chad Main on Technically Legal

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500-page bound merger agreements, office printers, and libraries lined with law books. Legal work looks a lot different now that most in-house counsel (and law firms for that matter) have adopted some form of distributed work. 

But that doesn’t mean the work itself has changed. Contracts still need to be written and signed, litigation still needs to happen, and employment law might be more important than ever. What’s become clear over a year into a global pandemic is that legal work can be even more effective without the office. To make it happen, however, lawyers need to adapt their communication mediums and technology in a way that fits company culture and mission. 

Automattic’s General Counsel, Paul Sieminski, recently joined the Technically Legal podcast to talk about how legal work can thrive in a fully distributed company. “It’s aimed at a legal audience, and I love to remind my fellow layers how much value we can add to a distributed organization,” said Paul of his appearance on the podcast. “We are trained to communicate clearly, and especially to write cogently and persuasively.  These are invaluable skills in any environment, but especially in an environment where writing is paramount…like a distributed company.”  Paul has written on the topic in other places, such as Modern Counsel

He talks about communication starting just after the 23:00 mark with host Chad Main. For that discussion, and legal topics spanning the advantages of creating a searchable document database, to what tools and protocols we use to communicate transparently while protecting confidentiality, you can learn more about legal work in the distributed model by listening to the full episode here.

Growing as a Leader: Matt Mullenweg on the Starting Greatness Podcast with Mike Maples Jr.

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“Was there a palpable time when you felt like…you had to have a new kind of thought as you got bigger?” asks Mike Maples Jr., host of the Starting Greatness podcast in an April conversation with Automattic founder and CEO Matt Mullenweg.

Matt shares several such pivotal moments in an episode full of stories and insight from the growth of Automattic, and of his own journey and leadership evolution.

“For better or worse, you become close personal friends with everyone because you’re kind of in the trenches,” Matt said, sharing a story about when the company almost accepted an acquisition offer at a time of friction among the small, but growing, Automattic team. “So when you fight, it kind of feels like you’re fighting with your partner, your significant other.”

Matt reflects on a journey from his Palm Pilot user group to first meeting Jeffrey Zeldman of A List Apart (and now a Principal Designer at Automattic), and later his first visit to San Francisco, all before committing full-time to WordPress and Automattic. Mike and Matt also touch on the difference between a learn-it-all and a know-it-all, and even some books that have been influential along the way.

Maples, partner in venture capital firm Floodgate, has also hosted Annie Duke, Mark Cuban, Tim Ferriss and David Sacks in the second season of Starting Greatness, a podcast dedicated to startup founders who want to go from “nothing to awesome, super fast.” You can listen to the full Starting Greatness episode, and all others, right here.

Another year of distributed work. A brand new set of questions.

In May of 2020, I wrote about the move to adopting a distributed model and how change happens slowly, and then all at once. Today most companies are approaching a year of distributed work and looking ahead at another. While the dust has started to settle for most companies, new questions are emerging — from who shoulders tax burdens for remote employees, to what ongoing support looks like for employees and their families. 

These questions go well beyond the productivity and collaboration topics that typically accompany any discussion around distributed work. And the answers are more important than ever as companies that want to return to the physical office look at another year away from it — and for others that plan to permanently embrace distributed work. A recent article by Chip Cutter and Emily Glazer in the Wall Street Journal examines what another year of remote working looks like along with some insights into how some companies are tackling some big, thorny issues.

Discussions about the future of work, such as whether to reduce the salaries of employees who have left high-cost cities, are priority items in board meetings and senior executive sessions across industries, according to chief executives, board members and corporate advisers. Listen to this article 6 minutes Among the questions companies are trying to resolve: Who should shoulder tax costs as employees move to new locations while working remotely? And what is the most effective way to support working parents? Companies say there is much at stake, from the happiness and productivity of employees to regulatory consequences, if they get these decisions wrong. 

Head to the Wall Street Journal to read the rest of the article.

Episode 26: Jack Dorsey and Matt Mullenweg on Remote Collaboration, Finding Serendipity, and the Art of Deliberate Work

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Join us for the latest episode of Distributed, as Matt Mullenweg interviews Jack Dorsey, co-founder and CEO of Twitter and Square. They discuss how both companies have embraced remote collaboration, the underrated value of deliberate work, and how questioning preconceived models from the get-go can change everything. 

This spring, Jack Dorsey told Twitter and Square employees they could work from home forever if they choose. But a year earlier –– before the global pandemic happened –– he had already started working from home two days a week. There wasn’t the noise or the distraction. It was a place and a time where he felt more freedom and creativity. 

Now, he reflects on how his way of working has evolved alongside Twitter and Square over the past year. From leading thousands of employees as a self-described introvert, to why he planned (and still does) to work from Africa for an extended period (spoiler: largely, to support entrepreneurs on the continent), Matt and Jack share ideas for combining the deliberate, thoughtful pace of asynchronous work with the serendipity that occurs in the office. 

“If we can run the company without missing a beat,” says Dorsey of planning to work in Africa, “it really opens the door for a lot, especially our ability to hire anywhere as well.”

Tune in to learn how meetings work at fully distributed Twitter and Square, what open source and the punk scene have in common, why bringing thoughtfulness into collaboration is more important than ever, and if Jack Dorsey ever wants to go back to the old board meetings. Plus a whole lot more. 

The full episode transcript is below. Thanks to Sriram Krishnan for help preparing for this episode.

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Episode 25: Davit Baghdasaryan on the Science of Sound in a Distributed Work World

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Trying to sound your best as you work away from an office more than ever before?  

As audio and video conferencing surge worldwide, Matt talks about the science of sound with Davit Baghdasaryan, the CEO of Krisp, a fast-growing company offering an AI-powered noise cancellation app for removing background noise on any conferencing platform. Krisp’s technology, including its proprietary deep neural network krispNet DNN, processes audio securely on the user’s computer. 

Find out how Krisp started, why Davit foresees his company returning to a hybrid work model, and what it means to Work from Forest

With employees in the United States and Armenia that shifted to working from home in 2020, Krisp surged this challenging year, announcing a $5M Series A round in August and growing to 600 Enterprise customers despite continuing to focus on consumer users. Check out this demo of how Krisp works in meeting room.)

A native of Armenia, Davit spends time in both countries leading Krisp. Prior to co-founding Krisp, Davit was a Security Product Lead at Twilio in San Francisco, among other security-focused technology leadership roles.

The full episode transcript is below.

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On the (Cool) Tools You Need for a Smooth Distributed Experience

The basic toolkit for distributed teams has stayed fairly stable in recent years — a real-time chat app, a robust video conferencing platform, and discipline-specific collaboration systems for engineers, designers, and support teams, to name a few. On his recent appearance on the Cool Tools podcast (hosted by Mark Frauenfelder and Kevin Kelly), Matt Mullenweg dives deeper into the world of distributed tools, talking about the ones that streamline and optimize his work as the CEO of a company that employs around 1,200 people across dozens of countries and multiple time zones.

Matt covers several fronts, from better webcam setups to messaging apps, and gives a special nod to P2, the WordPress theme that powers Automattic’s internal blogs:

We use actually a free theme called P2, which turns your internal blog or any blog, really, into kind of a real-time system. It sort of puts a posting box on the homepage, so anyone who’s a logged-in user can see a posting box right on the homepage. You don’t have to visit a separate admin. And then it has fully threaded comments and posts also on the homepage. And by real time, I mean if a new comment or post comes in, it’ll actually pop up on your screen without you having to reload. It’s great for asynchronous conversations. We use it instead of email actually, and it’s been definitely the thing that’s allowed us to scale to now 1,200 people.

Listen to the entire conversation on Cool Tools

Episode 23: Lara Hogan on the Secret to Being a Successful Manager

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Are companies setting up their managers for success? What are BICEPS? How do you assemble your colleagues like a management Voltron?

Lara Hogan is the founder of Wherewithall, a firm that specializes in management and leadership training — a company that Automattic has worked with in the past. She’s the author of Resilient Management, a must-read for anyone who is a manager, wants to become one, or generally just wants to learn how to be a better teammate.

Lara spent a decade growing emerging leaders as the VP of Engineering at Kickstarter and an Engineering Director at Etsy.

Related links:

Management Voltron Bingo Card

Core Needs: BICEPS (Paloma Medina)

@Lara_Hogan on Twitter

Full episode transcript is below.

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Distributed FAQ: Should Companies Use Software Tools to Monitor Remote Workers?

In Distributed FAQ, Matt Mullenweg addresses some of the most common issues companies, executives, and individuals face as they consider transitioning to a distributed model.


Q. At distributed companies, managers can’t always see when — or if — employees are working. Do you recommend using monitoring software to ensure people are productive?

A. No.

I don’t advocate for using this type of software at all. Instead of monitoring progress, you should focus on outcomes. Respect the outcome and trust that your employees will do their jobs.

Culture is what you do when no one is looking — it’s something I firmly believe in, and it’s especially true in the context of trust in a distributed setting.


Even in companies that thrive on mutual trust, different communication styles and social-interaction preferences can lead to friction. Listen to Matt’s conversation with Morra Aarons-Mele about introversion and anxiety in distributed companies.