Siqi Chen, a seasoned entrepreneur and CEO/CFO of Runway, shares his journey from creating viral social games like Mafia Wars to revolutionizing financial modeling. He talks about the importance of crafting clear company values and building trust through authentic communication. Siqi also critiques Zynga's strategy and highlights the significance of compliance in startups. Expect fresh insights on balancing work-life and practical advice for technical founders aiming to thrive in today's competitive landscape.

Rodney Brooks, a pioneering robotics expert and founder of iRobot, shares his journey in revolutionizing home tech with the Roomba. He discusses the delicate balance between ambition and risk, emphasizing the role of luck in success. Brooks also delves into bootstrapping startups versus seeking funding and the importance of building robots that cooperate with humans. He offers insight into predicting technological trends and provides valuable advice to today’s innovators, underscoring the need for trust and user-friendly designs in robotics.

The story of the digital content-sharing platform Gumroad challenges every aspect of the received wisdom about building successful companies. After it almost went under, founder and CEO Sahil Lavingia decided to pare down to the essentials rather than walk away. Then he took his characteristic counter-intuitiveness further and left Silicon Valley for Provo, Utah. Through it all, he never lost sight of what he was trying to do and his joy in building products. Gumroad is now thriving, with $175 million in volume last year, all thanks to Lavingia’s willingness to take a different path to success. Among the many things he’s learned along the way are the value of getting a fresh perspective and the virtue of patience – even when it’s unexciting. Commitment is often overlooked in heady times, but as he told me, “A lot of people are so concerned about catching the next train because it's the last one. They think it's over. But there are many more trains – just make sure you're at the train station. That's the important thing.” He had a lot to say about this, as well as Gumroad’s unique equity and dividend model, which it’s now sharing with other companies.   Other topics we touched on include: His long history of taking unconventional paths How he broke into the startup ecosystem Why building more than one product at a time is better than building a single perfect product How to get into the wild world of AI startups Making difficult business decisions for survival Appreciating the opportunity to continue doing what you love The power of equity and incentivizing for the future And so much more — Brought to you by: Vanta – Automate compliance, manage risk, and prove trust—continuously. Get $1,000 off. Runway – The finance platform you don’t hate. ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Learn more⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. — Where to find Sahil Lavingia: • Sahil’s site: https://sahillavingia.com/  • LinkedIn: https://www.linkedin.com/in/sahillavingia  • Bluesky: https://bsky.app/profile/shl.bsky.social  • X: https://x.com/shl • Instagram: https://www.instagram.com/shlpaints/?hl=en Where to find Eric: • Newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ericries.carrd.co/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  • Podcast: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ericriesshow.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  • YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@theericriesshow⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  — In This Episode We Cover: (03:15) Singapore and America as the ultimate high-growth startups (04:50) How Sahil first encountered entrepreneurship as a teen graphic designer (07:15) The new meaning of “knowledge work”  (11:10) Sahil’s impressions of American possibility after growing up in Singapore and returning (16:33) Sahil’s history of deviating from the expected path (19:27) Gumroad’s path from a failed funding round in 2015 to profitability in 2023 (24:17) How Sahil broke into the startup ecosystem and his first iPhone app  (27:41) Sahil’s advice for people looking to break into the new rising tide of AI (30:38) On not putting all your eggs in one product basket (32:59) How and why he left Pinterest (34:48) Surfing and treading water as business cycles (41:36) Overnight successes that are really a long time in the making (45:59) How Sahil started Gumroad (49:19) Reconciling getting fired with successfully raising money for a new company (54:26) The failure to build a billion-dollar company (1:03:42) How to prioritize survival (1:06:33) The pivotal decision to leave San Francisco for Provo, Utah (1:08:11) The current state of Gumroad  (1:11:22) How Gumroad is structured to solve some of the classic business problems: equity, ownership, dividends (1:13:53) Incentivizing for the long-term (1:22:12) How Gumroad is helping other companies copy their model  (1:25:16) Lightning round You can find the transcript and references at ⁠⁠⁠https://www.ericriesshow.com/⁠⁠ — Production and marketing by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Eric may be an investor in the companies discussed.

In a dynamic conversation, Jonathan Ross, Founder and CEO of Groq—a semiconductor startup valued at $2.8 billion—shares his journey from Google engineer to entrepreneur. He discusses the risks and near-death experiences that shaped Groq, emphasizing its mission to democratize low-cost generative AI computation. Topics include the importance of corporate culture in driving innovation, the challenge of competing with giants like Nvidia, and the need for long-term vision and empathy in tech leadership. Ross’s insights illuminate the transformative potential of AI and the true nature of disruption.

Wendy Gonzalez is the CEO of Sama, an ethical AI company that provides training and jobs with equitable pay and benefits to those who face the greatest barriers to stable employment. Among the companies it provides AI development data to are Microsoft, Ford, Walmart, Google, and many others. But before its current incarnation, Sama was a very different organization. It began as a non-profit, the brainchild and lifelong passion of its founder, Leila Janah, who sadly passed away in 2020. Her vision was to provide under-served communities in sub-Saharan Africa with opportunities for what she called “dignified work.” She believed this was the fastest and most sustainable way for people to not only gain their financial independence but to spread prosperity in their communities. Wendy and I discussed the advantages of being a company that puts human potential and intelligence first in everything it does from numerous angles. Sama’s example shows beyond a doubt that everything we’ve been taught about how to succeed in business is far from the only way – or even the best way – to thrive. In addition, we touched on: • Why it’s difficult to think long-term as a non-profit • The relationship between human judgment and AI • Why Sama became a B-Corp • The power of putting clear ethical boundaries on the work you accept • Why choosing investors that align with your mission is make-or-break • The future of AI and multi-modal models • And more — Brought to you by: Mercury – The art of simplified finances. ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Learn more⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. DigitalOcean – The cloud loved by developers and founders alike. ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sign up⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Neo4j – The graph database and analytics leader. ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Learn more⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. — Where to find Wendy Gonzalez • LinkedIn: https://www.linkedin.com/in/wendy-gonzalez-a319788/ Where to find Eric: • Newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ericries.carrd.co/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  • Podcast: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ericriesshow.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  • YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@theericriesshow⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  — In This Episode We Cover: (05:17) The importance of our relationship to the people who make the products we use (06:42) The human care that goes into AI development (07:57) Sama’s mission (09:12) How Sama got to its leadership position in the creation of ethical AI (10:31) The focus on valuing human judgment in work (13:50) The Sama origin story (17:13) The informal economy vs. the formal economy (18:36) How Sama’s model helps break the poverty cycle (20:01) Giving human capital a chance to shine (21:30) Why Sama doesn’t pay people for training and the success of that approach (23:44) Leila Janah and her vision for Sama (27:38) How and why Sama converted to a for-profit company with a foundation attached (29:42) Identifying AI as the pivot (31:02) The difficulties of having a long-term plan in the non-profit world (32:49) Why Sama needed to build its own technology and raise the money to do so (36:10) How a non-profit becomes a for-profit (37:29) How Sama split into two entities: a company and a foundation (39:41) Sama’s governance structure including how the foundation is represented in the (43:56) Choosing mission-aligned investors (45:46) How Sama’s success disproves conventional business theory (52:00) Turning a liability into strategy (53:47) How Sama’s mission led it to create real value and be in position for the emergence of AI (58:06) The need for standards and ethical guidelines for the data supply chain (1:01:46) Combating bias and danger through visibility (1:03:57) The case for ethical data as a competitive strategy (1:07:21) Wendy’s thoughts on what the future of AI will bring (1:10:30) Lighting round, including the creation of Sama’s Ethics Guild  (1:23:46) What Wendy wishes she’d known ten years ago You can find the transcript and references at https://www.ericriesshow.com/ — Production and marketing by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Eric may be an investor in the companies discussed.

Sal Khan, founder of Khan Academy and author of 'Brave New Words,' shares his journey from tutoring a cousin to creating a global educational platform. He discusses the power of nonprofit education, emphasizing mission over profit and the ethical implications of AI in learning. Sal advocates for incorporating AI to enhance student engagement while pushing back against fears of technology. He also stresses the importance of balancing work and values, promoting a culture of curiosity and lifelong learning among students and educators.

Founded in 2011 in the distinctly non-Silicon Valley location of Columbia, Missouri, software integration company Zapier hit profitability in 2014. Today, the company is valued in the billions, and is poised to keep thriving as AI becomes a normal part of everything we do online. My guest on this episode of The Eric Ries Show is co-founder and CEO Wade Foster, whose ethos from the earliest days on has been: “If you're going to try and build a company, don’t do anything that doesn’t matter.” For Zapier, that has meant staying as close as possible to customers from the start in order to build a product they really want. It’s no wonder their journey to product-market fit was easier than most founders can ever dream of – a story Wade tells in the episode that involves the magic of an early adopter and a lot of hard work.  From that customer delight, the company was able to build a flywheel and growth engine that have kept it steadily growing with minimal outside investment ever since, a path it fully intends to stay on. As Wade told me, they’re “willing to sacrifice a little bit of revenue for the durability of these customers over the long haul.” We also talked about how the company maintains its culture now that it’s expanded to 750 people, all of whom work remotely, and why product and marketing aren’t actually separate functions, especially at the beginning of a company’s life. Other topics we touched on include: Not taking Silicon Valley wisdom at face value How he knew he was meant to be an entrepreneur The fear of being overtaken by a competitor and how to live with it Zapier’s “second founding” Building products with AI in mind Wade’s favorite Zap And much, much more — Brought to you by: Mercury – The art of simplified finances. ⁠⁠⁠⁠⁠⁠⁠⁠Learn more⁠⁠⁠⁠⁠⁠⁠⁠. DigitalOcean – The cloud loved by developers and founders alike. ⁠⁠⁠⁠⁠⁠⁠⁠Sign up⁠⁠⁠⁠⁠⁠⁠⁠. Neo4j – The graph database and analytics leader. ⁠⁠⁠⁠⁠⁠⁠⁠Learn more⁠⁠⁠⁠⁠⁠⁠⁠. — Where to find Wade Foster: • Wade’s Zapier blog: ⁠https://zapier.com/blog/author/wade-foster/⁠ • X: ⁠https://x.com/wadefoster⁠ • LinkedIn: ⁠https://www.linkedin.com/in/wadefoster/⁠ Where to find Eric: • Newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠https://ericries.carrd.co/⁠⁠⁠⁠⁠⁠⁠⁠  • Podcast: ⁠⁠⁠⁠⁠⁠⁠⁠https://ericriesshow.com/⁠⁠⁠⁠⁠⁠⁠⁠  • X: ⁠⁠⁠⁠⁠⁠⁠⁠https://twitter.com/ericries⁠⁠⁠⁠⁠⁠⁠⁠  • LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/eries/⁠⁠⁠⁠⁠⁠⁠⁠  • YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@theericriesshow⁠⁠⁠⁠⁠⁠⁠⁠  — In This Episode We Cover: (00:40) Introducing Wade Foster (06:33) The transition to Silicon Valley and defying received wisdom (09:18) Where the courage to do things differently comes from (14:08) The internship that made him realize he was an entrepreneur (17:07) The value of staying close to customers during product development (18:07) The genesis of Zapier (21:24) How Andrew Warner became Zapier’s first customer (24:43) The company’s ease in finding product-market fit (30:03) The early days of company-building (31:55) How they stayed small and worked with a single million dollar Series A raise.  (32:48) Reaching profitability in two and a half years (34:50) On not buying into the need to burn cash and hire quickly (36:44) The unique power of the company’s distribution engine (39:25) Zapier is a classic Lean Startup story (41:14) How the company discovered its growth engine and validated its growth hypothesis (43:30) How Zapier’s flywheel works (47:46) The problems of over-funding and monetization (49:25) Building and maintaining trust  (1:12:25) Zaper’s “build principles” (1:00:39) The power of story-telling for sharing values (1:04:57) Wade’s thoughts on and excitement about how AI will affect Zapier and work (1:10:34) How AI has spurred Zapier’s second founding (1:13:30) The vertigo of evolving beyond the founder-entrepreneur role (1:15:24) Lightning round – including Wade’s favorite Zap!  — Production and marketing by ⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co/⁠⁠⁠⁠⁠⁠⁠⁠. Eric may be an investor in the companies discussed.

Tim O'Reilly, founder of O'Reilly Media and a guiding light in tech for decades, discusses the interplay between technology and society. He emphasizes the importance of long-term thinking, ethical practices, and creating value for all stakeholders instead of merely maximizing profits. O'Reilly explores AI's multiple facets, critiques the current focus on shareholder value, and calls for an economy that sustains vital services. His insights challenge tech leaders to prioritize ethics amidst profit pressures and redefine the true purpose of the metaverse.

Stacy Brown-Philpot, former CEO of TaskRabbit and a notable board member at companies like HP and Nordstrom, dives deep into the gig economy and compassionate leadership. She shares insights on Google’s cultural evolution and the shift from 'Don't be Evil' to reality. Stacy discusses TaskRabbit’s strategic pivots, including its transition to home services and the acquisition by Ikea, emphasizing mission-driven decisions. Her stories reveal the importance of diversity and integrity in leadership, encouraging others to stand for what they believe in.

In this engaging discussion, Reid Hoffman, influential executive and investor known for co-founding LinkedIn, shares his insights on AI's role in shaping our future. He recounts how he facilitated the meeting that sparked the OpenAI-Microsoft partnership. Hoffman emphasizes the need for ethical governance in technology, advocating for a human-centered approach. He explores the transformation AI brings as a 'meta tool' and the importance of leadership in tech during politically charged times, highlighting the balance between optimism and caution in innovation.