The pitch that changed air travel forever: $3B in preorders, Richard Branson’s backing, and the return of supersonic flight | Blake Scholl (Boom Supersonic)

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.

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.

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.

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.

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.

In this episode of The Eric Ries Show, I sit down with Ev Williams—someone whose work has profoundly shaped the modern internet. Ev co-founded Twitter, created Medium, and before all that, built Blogger, the original blogging platform (and the one where my own blog, Startup Lessons Learned, still lives today).We cover a wide range of topics, but at the heart of our conversation is this: what does it mean to resist short-term pressures and build with long-term integrity?Ev reflects on the early days of the internet, the cultural shifts inside big tech, and what happens when the systems we design begin to shape us in return. He also shares the thinking behind his latest venture, Mozi—an app designed to make it easier for people to meet up in person, with less friction and more intention.In our conversation today, we talk about the following topics: • The value of building strong relationships (and how they compound over time)• The inside story of Google’s acquisition of Blogger• Google’s “don’t be evil” policy, and a case for radical honesty • Why Ev believes social media’s downsides were inevitable• How data obsession can kill creativity• Ev’s “feel it” principle and what it means for entrepreneurs• The backlash against Medium’s login wall, and what it taught him about friction and trust• How strong governance and intentional culture can safeguard a company’s mission• Ev’s latest project, Mozi—an app that takes the hassle out of meeting up in person• And much more!—Brought to you by:• 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 Ev Williams:• LinkedIn: https://www.linkedin.com/in/evanwilliams/• X: https://x.com/ev—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(02:29) How Ev feels knowing his company, Blogger, acquired by Google, is still going (06:01) Why many of Ev’s businesses have endured (13:26) Ev’s early years growing up on a farm and how he ended up at O’Reilly (20:46) The internet’s shift from idealism to reality—and why we still can’t see its full impact(28:00) Motivations driving founders, and how Ev realized it’s about creativity (30:55) Google’s ‘don’t be evil’ policy, and the importance of creating high bar values(37:45) Ev’s thoughts on what went wrong with social media and if AI companies can do better(45:00) The protective role of good governance(54:10) Insights gleaned from the book Why Greatness Cannot Be Planned (1:00:14) Why MBA-thinking and metric obsession are culture killers(1:05:23) A story about trusting in a hypothesis before data is there (1:06:35) Medium’s failure with the login pop-up (1:09:58) How good governance and strong culture empower torchbearers (1:12:34) An overview of Mozi, an app that helps make in-person meetups easier(1:16:10) 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'm joined by Jess Mah, an extraordinary entrepreneur who launched her first six-figure business in middle school and went on to co-found more than 10 companies collectively valued at over $1 billion.Jess rose to public acclaim and earned a spot on Forbes' 30 Under 30 while privately facing the reality that her startup, inDinero, was far from profitable. That moment of failure became her turning point. Without VC funding, Jess had to rethink everything: her approach to building companies, her work methods, and her true priorities. What emerged was a more sustainable approach to entrepreneurship that prioritizes long-term thinking, authenticity, and mental health.In our conversation, we explore:• The hidden upside of failure and how it transformed Jess's career• Why inDinero's failure to attract VC money was ultimately a blessing in disguise• How AI is lowering barriers to starting a business with less capital and fewer workers• Why authenticity beats performative positivity• How Jess manages her mental health and her iterative learning approach inspired by 'kodawari'• The “independent director problem” and how investor-beholden directors can undermine long-term strategy • Why funding private companies is a frequently overlooked way to create global impact• Jess’s 90-day trial method for evaluating executive talent • Jess’s work supporting other female founders• 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 Jess Mah:• LinkedIn: https://www.linkedin.com/in/jessicamah/• X: https://x.com/jessicamah• Website: https://jessicamah.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(02:30) Why happiness eludes so many high achievers(10:15) Why Jess considers herself lucky that inDinero was not a rapid growth company(14:20) How Jess discovered that habits like meditation and exercise drive success(17:10) Silicon Valley Bank: why short-term thinking and exploitation are bad business strategies(24:00) Why it’s so hard to break out of the default culture of rapid growth (28:30) Why Jess walked away from the Silicon Valley playbook(33:11) Where Jess’s strength comes from (40:25) Why true accountability doesn’t require a combative board(44:43) What good governance looks like—and why it’s different for every company(50:10) Jess’s long-term approach to goal planning, both in life and work (51:34) Jess’s barbell approach: balancing cool businesses with world-changing tech(58:15) Jess’s approach to hiring and spotting well-matched talent(1:04:20) Strategies Jess uses to manage her emotions and learn from failure(1:10:54) 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 Marten Mickos, a serial tech CEO who has been at the forefront of some of the most transformative moments in open-source technology. From leading MySQL through its groundbreaking journey to guiding HackerOne as a pioneering bug bounty platform, Marten's career is a masterclass in building innovative, trust-driven organizations.Our wide-ranging conversation explores Marten's remarkable journey through tech leadership, touching on his experiences building game-changing companies and, more recently, his work coaching emerging CEOs. We dive deep into the world of open source, company culture, and the nuanced art of leadership.In our conversation today, we talk about the following topics: • How MySQL revolutionized open-source databases and became Facebook’s database• The strategic decision to make MySQL open source and leverage Linux distributions• The art of building a beloved open-source project while creating a profitable business model• How a lawsuit solidified MySQL's position in the open-source database market• The role of transparency and direct feedback in building organizational trust• Why Marten was drawn to HackerOne's disruptive approach to cybersecurity• Marten’s transition to coaching new CEOs • Marten’s unique "contrast framework" for making complex decisions• And much more!—Brought to you by:• 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 Marten Mickos: • LinkedIn: https://www.linkedin.com/in/martenmickos/• Bluesky: https://bsky.app/profile/martenmickos.bsky.social—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(03:15) The first time Eric used MySQL(07:10) The origins of MySQL and how Marten got involved (13:22) Why MySQL pivoted to open source to leverage the power of Linux distros(17:03) Open source vs. closed (18:56) Building profitable open-source companies (24:52) The fearless company culture at MySQL and the Progress lawsuit(29:30) The value of not cutting any corners (33:35) How a dolphin became part of the MySQL logo (35:55) What it was like to build a company of true believers(38:47) Marten’s management approach emphasizes kindness and direct feedback (42:12) Marten’s hiring philosophy(45:14) Why MySQL sold to Sun Microsystems and tried to avoid Oracle (50:24) How Oracle has made MySQL even better(52:22) Why Marten decided to lead at HackerOne(55:41) An overview of HackerOne(59:31) How HackerOne got started and landed the Department of Defense contract(1:03:19) The trust-building power of transparency(1:08:30) Marten’s successor and the state of HackerOne now(1:09:23) Marten’s work coaching CEOs(1:14:20) Common issues CEOs struggle with (1:16:45) Marten’s contrast framework (1:26:12) The book of Finnish poetry that inspired Marten’s love of polarities—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'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.