How GitLab scaled to 30M users with transparency, remote work, and the ultimate employee handbook | Sid Sijbrandij
In this episode of The Eric Ries Show, I’m joined by Sid Sijbrandij, co-founder and Executive Chair of GitLab—one of the world’s most radically transparent and values-driven software companies.Sid shares how GitLab evolved from an open-source side project into a publicly traded DevOps platform, all while remaining deeply aligned with its values. From turning down a $10 million offer to maintaining control through dual-class shares, Sid walks us through the principles and systems that have shaped GitLab from the start.We also delve into GitLab’s renowned, live, and public 2,000-page handbook—how it functions not only as documentation but also as a recruiting tool, cultural backbone, and governance mechanism.In our conversation today, we talk about the following topics:• Why Sid once cold-pitched a submarine inventor—and got hired• What led GitLab to turn down a $10M buyout and pursue an IPO• Why GitLab favors “boring solutions” by default—and avoids reinventing the wheel• The role of GitLab’s live, public handbook in building transparency and trust• Why every change at GitLab must be made in the handbook first• How the handbook supports hiring, alignment, and radical transparency• GitLab’s approach to decentralized decision-making• Why “customer results” sits at the top of GitLab’s values hierarchy• Sid’s case for open core as the future of software•How GitLab encourages informal connection in a remote-first culture—and the role of in-person meetups• And much more—Brought to you by:• Ahrefs – Get instant website traffic insights, without the noise. Learn more. —Where to find Sid Sijbrandij:• LinkedIn: https://www.linkedin.com/in/sijbrandij/• X: https://x.com/sytses—Where to find Eric:• Newsletter:https://ericries.carrd.co/ • Podcast:https://ericriesshow.com/ • YouTube:https://www.youtube.com/@theericriesshow —In This Episode We Cover:(00:00) Intro(02:52) The origins of GitLab(04:15) The MVP of GitLab and how it has evolved to a DevOps platform (05:09) Sid’s internships and why he chose to work with submarines after(08:57) How Sid became a submarine engineer (11:10) How Ruby sparked Sid’s interest in programming (12:28) Why GitLab said no to $10M and chose YC and decided to go IPO(17:45) How GitLab kept control including granting 10x voting shares before going public(22:25) GitLab’s extreme commitment to their values (28:29) GitLab’s Handbook and how changes are made (33:11) How GitLab handles pushback and how the handbook builds trust (37:38) An explanation of buyer-based open core at GitLab (38:35) The challenges implementing a lean startup approach (45:26) Keeping the organization aligned: How GitLab reinforces their values (53:51) Why GitLab updates values (55:57) Why senior engineers have an easier time securing budget(57:21) Putting customers first: GitLab’s value hierarchy explained(59:08) The case for decentralized decision-making—and how GitLab makes it work(1:03:24) The handbook’s role in recruiting and building alignment(1:06:25) Maintaining transparency after IPO(1:10:55) The three phases of GitLab’s all-remote operating policy (1:17:04) How GitLab developed its open core business model (1:20:19) The trust-building power of open source and Sid’s case for open core(1:25:20) Protective governance measures GitLab helps companies take (1:29:28) How Sid has been doing on his cancer journey, and his work to help others —You can find episode references at https://www.ericriesshow.com/—Production and marketing by Pen Name.Eric may be an investor in the companies discussed.
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1:33:29
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1:33:29
Turning down $200 million and the big bets that led to powering 40% of the internet
In this episode of The Eric Ries Show, I’m joined by Matt Mullenweg, CEO of Automattic and co-founder of WordPress, the open-source platform that now powers 43% of the internet.Recorded on the 20th anniversary of Automattic, our conversation is a deep dive into what it takes to build enduring companies on top of open infrastructure. We explore Matt’s open-source philosophy, why WordPress has stayed true to its roots, and how Automattic continues to innovate, from pioneering remote work to rethinking compensation models.In our conversation today, we talk about the following topics: • The early days of WordPress and its open-source fork from b2/cafelog• Why trust is a company’s greatest asset—and how open source fuels it• The overlooked power of open standards like RSS• How open source moved from fringe to mainstream, and is even embraced by Microsoft • Why Automattic started remote-first in 2005, long before it was common• How global salaries help Automattic attract and retain top talent• Automattic’s alignment offer that reinforced team commitment and focus• What Matt’s excited about in AI• And much more!—Brought to you by:• Ahrefs – Get instant website traffic insights, without the noise. Learn more. —Where to find Matt Mullenweg: • X: https://x.com/photomatt• LinkedIn: https://www.linkedin.com/in/mattm/• Instagram: https://www.instagram.com/photomatt/?hl=en• Website: https://ma.tt/—Where to find Eric:• Newsletter:https://ericries.carrd.co/ • Podcast:https://ericriesshow.com/ • YouTube:https://www.youtube.com/@theericriesshow —In This Episode We Cover:(00:00) Intro(02:05) Reflecting on 20 years of Automattic(03:14) Why Matt turned down an offer to buy WordPress for hundreds of millions of dollars(08:34) The story of WordPress and its open-source origins (15:15) How Matt’s love of jazz inspires his collaborative work style(16:12) The ethos of WordPress(18:38) Why WordPress followed web standards rather than create its own (23:30) The Four Freedoms of software and how open source builds trust(28:46) Why open source was once demonized—and what changed(33:35) Eric’s open source future prediction and Matt’s thoughts(38:03) Sol Price’s customer focus and why great businesses give more than they take(40:34) Why Matt started Automattic and chose to operate fully remote (49:34) More unique features of Automattic (54:40) Matt’s thoughts on when to go to court (58:15) Alignment offers, and other ways Automattic keeps employees aligned (1:01:52) The state of Automattic currently, and their new product, Beeper (1:04:26) Matt’s thoughts on AI (1:06:36) Advice for aspiring open source founders—and Matt’s dream projects—You can find episode references at https://www.ericriesshow.com/—Production and marketing by Pen Name.Eric may be an investor in the companies discussed.
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1:10:48
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1:10:48
The playbook for fixing toxic culture, pointless friction, and broken systems | Bob Sutton (Stanford, NYT bestselling author)
In this episode of The Eric Ries Show, I’m joined by Bob Sutton, organizational psychologist and New York Times bestselling author of several influential books on leadership, behavior, and workplace culture, including his latest: The Friction Project.We explore insights from across his body of work, including real-world examples of large organizations that have figured out how to operate more effectively and ethically—despite the inherent messiness of human systems.We discuss:• Ideas from The Knowing-Doing Gap, including the importance of psychological safety and a breakdown of “the smart talk trap”• Why even the best-run companies are still flawed• The surprising number of companies owned by private foundations, including Hershey Chocolate and Ikea• How well-run organizations resist management fads while staying open to real innovation• A story from Tim Cook about critical thinking in HR—and the cost of over-hiring• “Addition sickness”: what happens when too many people work on a problem• Strategies for removing friction• The “No Asshole Rule”: why toxic leaders damage performance and morale• The best founders strike the right balance between confidence and humility • And much more!—Brought to you by:• Ahrefs – Get instant website traffic insights, without the noise. Learn more. —Where to find Bob Sutton: • LinkedIn: https://www.linkedin.com/in/bobsutton1/• Bluesky: https://bsky.app/profile/bobsutton.net• Website: https://bobsutton.net/—Where to find Eric:• Newsletter:https://ericries.carrd.co/ • Podcast:https://ericriesshow.com/ • YouTube:https://www.youtube.com/@theericriesshow —In This Episode We Cover:(00:00) Intro(01:45) Insights from The Knowing Doing Gap(09:29) How Becky Margiotta rewarded the doers of her 100,000 homes project (12:24) An explanation of why every organization is flawed (21:32) A case for still trying to improve the way companies are run (26:03) How larger organizations always do things worse—some worse than others(27:58) A case of organizational improvement: The California Department of Motor Vehicles (29:58) Companies owned by private foundations and other unique models(33:52) Lessons from Tim Cook around thinking critically about hiring(36:26) Addition sickness(39:58) Strategies for removing friction and adding good friction (46:42) Simple practices that work(49:50) The ‘no asshole’ rule(52:32) The pitfalls of holacracy and an explanation of ‘stagegate’(57:18) Why founders sometimes need to step back after scaling(1:01:09) Advice for founders who want to stay CEOs and operate in founder mode(1:04:40) The importance of ‘torchbearers’ and resisting pressures for short-term gains(1:08:30) A case for doing things the right way, even if you don’t have to (1:11:05) How corruption eventually degrades an organization (1:18:03) Lightning round—You can find episode references at https://www.ericriesshow.com/—Production and marketing by Pen Name.Eric may be an investor in the companies discussed.
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1:27:34
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1:27:34
The pitch that changed air travel forever: $3B in preorders, Richard Branson’s backing, and the return of supersonic flight | Blake Scholl (Boom Supersonic)
What does it take to challenge a century-old status quo in aviation? In this episode of The Eric Ries Show, I sit down with Blake Scholl, Founder and CEO of Boom Supersonic, a company on a mission to bring back supersonic air travel—sustainably and affordably.Blake doesn’t come from aerospace. He’s a computer scientist and former Amazon engineer who sold his startup, Kima Labs, to Groupon. What he does have is a clear mission, first principles thinking, and relentless execution. His story is a case study in how deep curiosity and iterative learning can outperform traditional credentials.In our conversation, we explore how to navigate high-uncertainty environments, challenge industry inertia, and build world-class teams to do the seemingly impossible.We cover: • The “bystander effect” in innovation—and how to avoid it• Why trying to disprove your idea is a founder's superpower• The edge of understanding when the context changes • The accidental pivot: How Boomless cruise came about • Blake’s “confusion list,” a practice to gain clarity • Why deep knowledge trumps credentials • How Blake leveraged Wikipedia and SeatGuru to understand how the Concorde failed• Boom's methodical approach to derisking each challenge• The "talent distillery"—Boom's framework for building exceptional teams• Tips for giving and asking for advice• How Boom uses AI to cut through the minutia and do more with less• Why accumulated learnings are a company's greatest asset• And more!—Brought to you by:• Gusto – Gusto is an easy payroll and benefits software built for small businesses. Get 3 months free.—Where to find Blake Scholl: • LinkedIn: https://www.linkedin.com/in/blakescholl/• X: https://x.com/bscholl—Where to find Eric:• Newsletter:https://ericries.carrd.co/ • Podcast:https://ericriesshow.com/ • YouTube:https://www.youtube.com/@theericriesshow —In This Episode We Cover:(00:00) Intro(02:43) How Boom is bringing back building commercial aircraft in the US(04:30) The bystander effect in innovation (07:30) The power of founder happiness and taking big bets (12:10) How Blake shifted from building an airline to building a supersonic company(14:07) Blake’s focus on first principles thinking(16:17) How boomless cruise came about, and other accidental discoveries (23:50) Blake’s practical exercise for gaining clarity (25:15) Boom’s origin story (31:10) How taking a bigger risk made Blake more comfortable with failure(32:24) A case for entrepreneurship as a truth-seeking discipline (33:47) How a founder’s deep understanding builds trust(38:20) Why Concorde failed, and how Boom solved for those problems(44:36) Boom’s plan for derisking each risk(47:33) How Boom was able to get Richard Branson on board with pre-ordering for Virgin(52:24) Boom’s relaunch after getting Virgin’s pre-order (56:00) How Blake focuses on the end state (59:22) The importance of aptitude and willingness to learn (1:01:34) Why building a team was the hardest part for Boom (1:06:32) Tips for getting better advice–and receiving it (1:09:40) How Boom maintains mission alignment working with outside vendors (1:14:04) Boom’s learnings from working with suppliers (1:19:35) The current status of Boom (1:20:57) How Boom uses AI to help with FAA certification and more(1:23:00) The size of teams at Boom, and how using AI enables them to have less engineers —You can find episode references at https://www.ericriesshow.com/—Production and marketing by https://penname.co/.Eric may be an investor in the companies discussed.
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1:26:59
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1:26:59
The Hidden Costs of Pay Inequality, And How Leading Companies are Solving It | Maria Colacurcio (Syndio)
In this episode of The Eric Ries Show, I’m joined by Maria Colacurcio, Co-Founder and CEO of Syndio, a workplace equity analytics platform. Syndio helps companies close pay gaps and build high-trust organizations. Maria has had a long career in leadership, previously co-founding Smartsheet and serving as a senior leader at Starbucks, where she focused on global communications and social impact.In our conversation, we discuss how to scale with integrity, navigate the complexities of equity, and lead with both data and principle. We cover: • The surprising insight that 1 in 5 pay remediations at Syndio benefit white men• The distinction between expanding opportunity and enforcing quotas• Why taking bias out of promotions makes companies stronger• The role curiosity and passion played in opening doors for Maria• Why “the reservoir of trust” is both the right thing to do and a smart business strategy• Syndio’s commitment to transparency through annual pay gap and equity disclosures• Why strategy and culture need to change as you scale• And much more!—Brought to you by:• Vanta – Automate compliance, manage risk, and prove trust—continuously. Save $1,000 today.• Wilson Sonsini – Wilson Sonsini is the innovation economy’s law firm. Learn more.• Gusto – Gusto is an easy payroll and benefits software built for small businesses. Get 3 months free.—Where to find Maria Colacurcio: • LinkedIn: https://www.linkedin.com/in/mcolacurcio/• X: https://x.com/mcolacurcio—Where to find Eric:• Newsletter:https://ericries.carrd.co/ • Podcast:https://ericriesshow.com/ • YouTube:https://www.youtube.com/@theericriesshow —In This Episode We Cover:(00:00) Intro(02:19) The executive order against DEI: what's changed, what hasn’t, what remains uncertain(07:20) The benefits and limitations of DEI programs(08:37) What is opportunity equity (10:20) How biases in performance reviews advance incompetent people(11:22) Syndio’s comp consistency analytics solution for pay consistency and pay equity (13:18) The importance of pay being tied to the company’s stated values(18:47) Why some CEOs are eager to abandon DEI (21:46) How to tell if a company is serious about fair treatment(25:00) Maria’s path to becoming the CEO of Syndio(32:09) Tech for solving a problem vs. for the sake of tech(35:12) Maria’s experience becoming a founder at Smartsheet and Syndio(38:22) The reservoir of trust and other learnings from Maria’s time at Starbucks(40:10) How Maria’s curiosity led to meeting Zev and founding Syndio (49:25) Syndio’s pivot and why Maria hired a lawyer to lead sales(52:15) An explanation of how Syndio’s software works (54:46) Syndio’s AI chatbot, Syndi(55:22) The current state of Syndio (57:02) How Syndio maintains alignment with its core values(1:02:14) Lightning round—You can find the transcript and references at https://www.ericriesshow.com/—Production and marketing byhttps://penname.co/.Eric may be an investor in the companies discussed.
Founder, entrepreneur, and best-selling author of The Lean Startup Eric Ries discusses how to build profitable companies for the long-term benefit of society. Ries talks with world-class technologists, thought leaders, executives, and others working to create a new ecosystem of trustworthy organizations with limitless potential for growth and a deep commitment to purpose. Together, they uncover the tools and methods to ensure the next generation of companies are designed to maximize human flourishing for generations.
Ireland