The Eric Ries Show

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.

Matt Mullenweg, CEO of Automattic and co-founder of WordPress, shares insights from his two-decade journey in building open-source software. He discusses the pivotal moment of turning down a $200 million acquisition, emphasizing commitment to mission over money. Mullenweg delves into the evolution of trust in open source and its mainstream acceptance, even by giants like Microsoft. He also highlights Automattic's early embrace of remote work and innovative compensation strategies, alongside his excitement about AI's future potential.

Bob Sutton, an organizational psychologist at Stanford and a New York Times bestselling author, dives into workplace culture and leadership challenges. He reveals insights from his latest work, discussing the high cost of toxic leadership and the 'No Asshole Rule.' Sutton highlights the 'smart talk trap' that can stifle action and the need for psychological safety. He also examines real-life examples of companies navigating ethical dilemmas and resisting management fads while promoting innovation, emphasizing the delicate balance between confidence and humility in effective leadership.

Blake Scholl, Founder and CEO of Boom Supersonic and former Amazon engineer, dives into the ambitious goal of reviving supersonic air travel. He discusses how innovative thinking can disrupt a century-old industry and the importance of first principles in tackling challenges. With topics like the "bystander effect" in innovation and utilizing AI for efficiency, Blake shares insights on building exceptional teams and the importance of curiosity. He emphasizes the value of learning from past failures and the need for a compelling mission in entrepreneurship.

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.

Ev Williams, co-founder of Twitter, Medium, and Blogger, shares his journey in shaping the modern internet. He reflects on resisting short-term pressures to build with integrity and the lessons learned from social media's evolution. Ev discusses Google’s acquisition of Blogger, the importance of strong relationships in tech, and his latest venture, Mozi—an app encouraging intentional in-person connections. He emphasizes the need for radical honesty and the balance between creativity and governance in tech, all while navigating the shifting landscape of the digital world.

Jess Mah, an entrepreneur who kickstarted her first business in middle school and co-founded over 10 companies valued at more than $1 billion, shares her transformative journey. She discusses how the failure of inDinero without VC funding led her to prioritize long-term thinking, authenticity, and mental health. Jess highlights the hidden benefits of failure, AI's role in lowering business entry barriers, and her unique 90-day trial for evaluating executives. Her insights on supporting female founders and the psychological aspects of entrepreneurship make for a compelling conversation!

Marten Mickos, a serial tech CEO known for steering MySQL through its open-source era and enhancing cybersecurity at HackerOne, shares fascinating insights from his career. He discusses how MySQL transformed the database landscape and the strategic shift to open-source. Marten dives into the significance of transparency in building trust, his practical approach to leadership challenges, and the role of mentorship as he transitions to coaching new CEOs. Also, he highlights the disruptive potential of bug bounty programs in enhancing cybersecurity.

In this episode of The Eric Ries Show, I'm joined by Celine Halioua, founder and CEO of Loyal, a groundbreaking biotech startup developing drugs to extend dogs' healthspan and lifespan. Celine's journey combines her passion for animals with a bold scientific mission that looks beyond pets to potentially transform human longevity as well.Our conversation explores:• Why ambitious, moonshot visions can paradoxically make fundraising and team-building easier• The critical early pivot that positioned Loyal for its first drug approval• The undervalued power of listening deeply and asking the right questions• Loyal's philosophy of exceeding regulatory requirements to build trust and advance the field• Balancing the startup need for speed with scientific rigor and safety• How Celine's background led her to focus on the untapped potential of canine longevity• The competitive advantage of pursuing novel ideas before they become industry trends• Why founder conviction and scientific expertise were crucial to overcoming skepticism• Celine's approach to governance and maintaining mission control for the long-term• Navigating the challenges of Silicon Valley as a female founder in biotech• The realistic timeline and milestones for Loyal's drug development and approvals• Building for truly long-term impact beyond conventional startup timelines• And much more! —Brought to you by:• Vanta – Automate compliance, manage risk, and prove trust—continuously. ⁠⁠Save $1,000 today⁠⁠.• Explo – Explo helps teams deploy customer dashboard portals. ⁠Get Started⁠.—Where to find Celine Halioua: • LinkedIn: https://www.linkedin.com/in/celinehh/• X: https://x.com/celinehalioua• Website: https://www.celinehh.com/—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(03:29) Early challenges Celine faced promoting Loyal(08:20) The early pivot that led to Loyal’s first drug approval(14:50) The importance of listening and asking questions(15:58) Why you have to love the mission (18:02) Why a lofty mission makes it easier to gain support(22:30) Loyal’s commitment to regulatory frameworks—and doing more than required(29:10) How to balance speed with safety and quality (34:36) Eric’s startup lesson on speed and compromises (38:22) How Celine became interested in the biotech space and canine longevity (47:32) The power of new ideas, and why it’s too late once it’s a trend(50:28) How Celine’s conviction and scientific expertise drove Loyal’s success(56:00) Celine’s advice to new founders: go deep(1:00:15) How and why Celine maintains control of Loyal(1:07:23) Breaking through the glass ceiling of Silicon Valley (1:15:50) Challenges of building a long-term company, and Loyal’s real milestones(1:21:11) The timeline of Loyal’s drug approvals (1:24:02) 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.

In this episode of The Eric Ries Show, I sit down with Daniel Dines, the Founder and CEO of UiPath, a company that started in robotic process automation (RPA) and is now making a bold shift into agentic AI. Dubbed “the boss of bots” by Forbes, Daniel has led UiPath from its humble beginnings to a $6.65 billion company that’s reshaping the future of automation.Daniel’s journey is anything but conventional. After working as an engineer on SQL at Microsoft, he felt a pull toward something more creative—building his own product. That decision led him back to Romania, where he founded the company that would eventually become UiPath.In our conversation today, we talk about the following topics: • Why stepping out of your comfort zone is key to growth• The Jack London book that changed Daniel’s life • The benefits of bootstrapping vs. raising big VC money• Why letting go is the hard part of a pivot• How failure can unlock unexpected opportunities• A case for mixing work and life to build a strong company culture • Why empowering employees is good for business • What Daniel learned from UiPath’s journey to IPO • Daniel’s plans for his second stint as CEO• Why Daniel is optimistic about the impact AI will have on the future of work• And more!—Brought to you by:• Wilson Sonsini – Wilson Sonsini is the innovation economy’s law firm. ⁠Learn more⁠.• Explo – Explo helps teams deploy customer dashboard portals. Get Started.• Gusto – Gusto is an easy payroll and benefits software built for small businesses. ⁠⁠⁠Get 3 months free⁠⁠⁠.—Where to find Daniel Dines:• LinkedIn: https://x.com/danieldines• X: https://www.linkedin.com/in/danieldines/—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(03:11) Growing up in communist Romania(10:00) The importance of breaking out of your comfort zone(13:41) Joy as a sign you’re on the right path (15:27) The Jack London book that made Daniel an entrepreneur (16:40) The beginnings of UiPath(18:50) Why writing code wasn’t enough for Daniel and why coding is creative (22:22) UiPath’s values (24:50) Why Daniel returned to Romania(28:00) Advantages of bootstrapping (30:50) Pivoting to become a product company from outsourcing(33:27) An early password management product that didn’t work out(34:55) The difficult pivot that led to the product that is UiPath now(39:10) How the early failures led to the big opportunity (41:37) Hitting product market fit (43:50) Why Daniel hired misfits, and the characteristics he looked for in hires(48:32) How Daniel protected UiPath's values and why he plans to renew the commitment(54:00) The importance of empowering employees at all levels to provide feedback(57:47) UiPath’s journey to IPO(1:01:30) Why Eric thinks he didn’t prepare Daniel psychologically for the difficulty of IPO(1:03:46) Synthetic volatility’s human cost (1:07:01) Why Daniel stepped down as CEO and why he’s resuming CEO duties(1:11:55) Daniel’s second stint as CEO: hiring people he likes and going all in on agentic AI(1:18:20) The promise of open source(1:19:24) Daniel’s thoughts on the future of work (1:24:36) Lightning round —You can find the transcript and references at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.ericriesshow.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠—Production and marketing by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.Eric may be an investor in the companies discussed.