In this episode of The Eric Ries Show, I’m joined by Siqi Chen, a four-time founder and the CEO and CFO of his latest venture, Runway. Runway offers a modern, user-friendly platform for financial modeling, headcount planning, and departmental budgeting—proudly branding itself as “the finance platform your team doesn’t hate.” With its distinctive marketing and brand-building approach, Runway has garnered significant attention. (Full disclosure: I’m an investor in the company.)

Siqi and I discuss his journey from building some of the most viral social games in Silicon Valley to founding Runway. We also delve into the challenges faced by technical founders, the art of viewing a business as a product, and how Siqi has sharpened his strategic thinking. Other key topics include:

• Lessons from founding Serious Business

• Critiques of Zynga’s strategy and the story of selling to them

• Practical advice for building trust

• Insights into Leaders in Tech and Stanford’s GSB program

• The importance of crafting clear, universally understood company values

• An overview of Runway’s platform, mission, and values

• A fresh take on the fallacy of work-life balance

• And so much more!

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Where to find Siqi Chen:

• LinkedIn: https://www.linkedin.com/in/siqic/

• X: https://x.com/blader/

• Instagram: https://www.instagram.com/blader/

• Facebook:  https://www.facebook.com/founder/

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) Meet Siqi Chen

(02:30) How Siqi came up with the idea for Mafia and the early years of gaming on Facebook

(05:10) The early investors in Mafia

(05:36) Siqi’s meeting with Keith Rabois and Max Levchin

(08:15) How Siqi was influenced by the Lean Startup approach

(11:04) How quickly Siqi’s career took off after moving to San Francisco 

(11:48) Founding Serious Business and creating Friends for Sale

(14:20) How Serious Business raised $5 million

(16:20) Why Serious Business sold to Zynga 

(17:20) The importance of prioritizing the business as much as the product

(19:11) Siqi’s learnings and advice for new founders 

(23:25) What Siqi learned working at Zynga

(27:18) Siqi’s time running product 

(29:20) Criticisms of Zynga and how they lost Eric’s trust

(33:42) The importance of trust and maintaining vision and mission

(39:15) An overview of Runway 

(44:38) What inspired Siqi to create Runway

(50:43) What Siqi learned from user interviews

(52:07) An example of time wasting inside a company

(53:24) The values at Runway and why they changed 

(58:35) Why you should write reflective values after having a high-performance team

(1:00:40) How Leaders in Tech shaped Siqi’s thoughts on values and building trust

(1:03:13) How open feedback builds trust

(1:08:20) The purpose of Runway

(1:11:34) Siqi’s struggles with strategy planning 

(1:13:31) A top down approach to entrepreneurship and why it’s not common

(1:16:38) The importance of employees understanding their contributions and impact 

(1:18:55) How Runway leverages AI 

(1:22:12) Runway’s dramatic launch with a timed lock

(1:23:04) How Runway communicates value to customers 

(1:24:54) Runway’s process for brand building and high-quality design 

(1:28:40) Lightning round

You can find the transcript and references at ⁠⁠⁠⁠⁠https://www.ericriesshow.com/⁠⁠⁠⁠

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Production and marketing by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

Eric may be an investor in the companies discussed.

Rodney Brooks has spent his entire life at the intersection of robotics, computers, and AI. When the Roomba vacuum cleaner launched in 2002, his company, iRobot, brought all three into millions of people’s homes.

iRobot had already succeeded with robots for space exploration, mine detection, search missions, and military applications. However, after the Roomba came out, it went public with a valuation of $600 million. By then, Rodney had been working on AI and robots for decades alongside the original creators of AI at Stanford and MIT. On today’s episode, we discuss:

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Runway – The finance platform you don’t hate. ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Learn more⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

—

Where to find Rodney Brooks:

• Website: https://people.csail.mit.edu/brooks/ 

• LinkedIn: https://www.linkedin.com/in/rodney-brooks-1a137517 

• Bluesky: https://bsky.app/profile/rodneyabrooks.bsky.social 

• X: https://x.com/rodneyabrooks

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) Welcome to the Eric Ries Show

(03:00) Taking iRobot public

(04:33) The change in company culture from private to public

(06:14) Rodney’s upbringing in Australia and early experiments with computers, robots, and mathematics

(7:19) The era of the computer operator

(9:37) Rodney’s arrival at Stanford in 1977 and move to MIT, at the dawn of AI

(11:05) His relationships with the creators of AI

(12:15) What innovators of AI and general intelligence thought they were creating at the time

(13:17) Rodney’s first AI startup, Lucid

(14:52) What Rodney learned about building startups from the experience

(18:31) Starting Light Robot, the space exploration company that eventually became iRobot

(21:29) The fourteen business models on the road to success, including toys

(26:03) The pivot to vacuums

(29:04) Learning about the minutiae of mass production

(34:43) Rodney’s thoughts on the relationship between consumers and the people who make goods

(38:08) Making robots that don’t take away human agency

(40:57) Building a trustworthy robotics company

(43:56) Balancing low-cost and reliable products

(47:00) RobustAI, Rodney’s new company

(51:54) The demand and need for warehouse robots

(53:39) Building robots that work with people rather than against them

(58:20) Talking to warehouse workers for insight into building robots

(59:20) Building startups with a high degree of difficulty

(1:05:29) The advantages of ambition

(1:08:03) Predicting the patterns of technology

(1:11:23) The role of luck in entrepreneurship

(1:12:30) Rodney’s thoughts on the current hype around AI and machine learning

(1:15:34) Rodney’s advice for today’s builders

(1:16:28) Lightning round

You can find the transcript and references at ⁠⁠⁠⁠https://www.ericriesshow.com/⁠⁠⁠

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Production and marketing by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

Eric may be an investor in the companies discussed.

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:

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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.

The story of Groq, a semiconductor startup that makes chips for AI inference and was recently valued at $2.8 billion, is a classic “overnight success that was years in the making” tale. On this episode, I talk with founder and CEO Jonathan Ross.

He began the work that eventually led to Groq as an engineer at Google, where he was a member of the rapid eval team – “the team that comes up with all the crazy ideas at Google X.” For him, the risk involved in leaving to launch Groq in 2016 was far less than the risk of staying in-house and watching the project die.

Groq has had many “near-death” experiences in its eight years of existence, all of which Jonathan believes have ultimately put it in a much stronger position to achieve its mission: preserving human agency in the age of AI.

Groq is committed to giving everyone access to relatively low-cost generative AI compute, driving the price down even as they continue to increase speed. We talked about how the company culture supports that mission, what it feels like to now be on the same playing field as companies like Nvidia, and Jonathan’s belief that true disruption isn’t just doing things other people can’t do or don’t want to do, but doing things other people don’t believe can be done – even when you show them evidence to the contrary. 

Other topics we touched on include:

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Runway – The finance platform you don’t hate. ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Learn more⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

—

Where to find Jonathan Ross:

• X: ⁠https://x.com/JonathanRoss321⁠ 

• LinkedIn: ⁠https://www.linkedin.com/in/ross-jonathan/⁠

Where to find Eric:

• Newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ericries.carrd.co/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

• Podcast: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ericriesshow.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

• YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@theericriesshow⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

—

In This Episode We Cover:

(04:24) Jonathan’s involvement with the DeepMind Challenge Match between AlphaGo and Lee Sedol

(06:06) How Jonathan’s work Google and how it led him to that moment

(08:46) Why generative AI isn’t just the next internet or mobile

(10:12) The divine move in the DeepMind Challenge Match

(11:56) How Jonathan ended up designing chips without the usual background

(13:11) GPUs vs. TPUs

(14:33) What risk really is

(15:11) Groq’s mind-blowing AI demo 

(16:23) How Jonathan decided to leave Google and start Groq

(17:30) The differences between doing an innovation project at a company and starting a new company

(19:03) Nassim Taleb’s Black Swan theory

(21:02) Groq’s founding story

(24:12) The difference in attitude towards AI now compared to 2016 and how it affected Groq

(25:46) The moment the tide turned with LLMs

(28:28) The week-over-week jump from 8,000 users to 400,000 users

(30:32) How Groq used HBM and what is it (the memory used by GPUs)

(32:33) Jonathan’s approach to disruption

(35:38) Groq’s initial raise and focus on software

(36:13) How struggling to survive made Groq stronger

(37:13) Hiring for return on luck

(40:07) How Jonathan and Groq think about the long-term

(42:25) Founder control issues

(45:31) How Groq thinks about maintaining its mission and trustworthiness

(49:51) Jonathan’s vision for a capital market that would support companies like Groq

(52:58) How Groq manages internal cultural alignment

(55:59) Groq’s mission and to preserve human agency in the age of AI how it approaches achieving it

(59:48) 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.

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.

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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 arrived at the idea for Khan Academy truly organically. While working at a hedge fund, he took time in the evenings to tutor a younger cousin in math over the phone. Soon, a family tutoring network was in place, and from there, it was only a few years before Sal realized that the kind of help he was giving his family could – and should – be made available to everyone for free, across disciplines and geographic locations. Today, Khan Academy has over 170 million users and is available in 50 languages in 190 countries.

To fully commit to his vision, he founded Khan Academy as a non-profit, providing advantages that companies focused on making money by any means necessary will never have. As you’ll hear, avoiding what he calls the “very strange” market forces around education has been one of the keys to Khan Academy’s ability to build deep trust and loyalty. 

It has also ensured a rare level of adaptability that has been especially important for Khan Academy’s role as a major early adopter of AI. Sal’s experiences with AI and education are widely applicable, as is his belief that we all have a duty to take a hand in shaping AI’s place in our world. Being open to new technology instead of fearing it can help us avoid the dystopian nightmares so many people have predicted are imminent. Equally important is his commitment to balance in all things, including salary and work-life choices not just for himself, but all Khan Academy employees. As he puts it, “Having a life can make you a better leader, thinker, and decision-maker.” His story, which has many chapters yet to come, shows that being a mission-controlled organization is no barrier to success in every sense. 

Other topics we touched on include:

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Brought to you by:

Mercury – The art of simplified finances. ⁠⁠⁠⁠⁠⁠⁠⁠⁠Learn more⁠⁠⁠⁠⁠⁠⁠⁠⁠.

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Neo4j – The graph database and analytics leader. ⁠⁠⁠⁠⁠⁠⁠⁠⁠Learn more⁠⁠⁠⁠⁠⁠⁠⁠⁠.

—

Where to find Sal Khan:

• X: @salkhanacademy

• LinkedIn: https://www.linkedin.com/in/khanacademy/

Where to find Eric:

• Newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ericries.carrd.co/⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

• Podcast: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ericriesshow.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

• YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@theericriesshow⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

—

In This Episode We Cover:

(04:24) Why Sal founded Khan Academy as a non-profit

(06:10) How his day job as a hedge fund analyst made him think longer-term

(09:26) How turning down venture capital has put Khan Academy in a better position for growth 

(11:24) Creating value as a non-profit

(12:54) How nonprofits can fill in for government in education and healthcare

(13:30) Sal’s skepticism about non-profits

(16:01) The social return on investment framework 

(18:22) Khan Academy by the numbers

(21:19) On making enough money and taking a risk to pursue a dream

(22:17) The counter-intuitive hiring benefits of being a non-profit

(27:46) Khan Academy as a leader in AI and education

(30:05) Khan Academy’s top fears around adopting AI 

(32:36) How being trustworthy led to early GPT-4 access

(34:04) Khan Academy’s AI experiments and results so far with Khanmigo

(36:55) Sal’s hopes for AI and special needs education

(38:52) Sal’s new book, Brave New Words

(41:51) AI as an amplifier of human intent

(43:38) The necessity of using technologies and tools we’re afraid of

(44:45) Balancing material needs and self-fulfillment

(48:20) Why Khan Academy has gone to fully remote work

(53:18) Lightning round!

You can find the transcript and references at https://www.ericriesshow.com/sal-khan/

—

Production and marketing by ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co/⁠⁠⁠⁠⁠⁠⁠⁠⁠.

Eric may be an investor in the companies discussed.

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:

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Brought to you by:

Mercury – The art of simplified finances. ⁠⁠⁠⁠⁠⁠⁠⁠Learn more⁠⁠⁠⁠⁠⁠⁠⁠.

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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! 

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Eric may be an investor in the companies discussed.

What is the relationship between technology and society? What happens to idealism over time? I’m fortunate to have discussed these questions and many more with Tim O’Reilly for this episode of The Eric Ries Show.

Tim is the founder of O’Reilly Media, which has provided countless programmers and technologists with foundational information for doing their work well. He’s also been a long-time witness to the changes and growth of tech, and has consistently looked far ahead of other people, perhaps most famously in his book What’s the Future and Why It’s Up to Us. 

Many call Tim the Oracle of Silicon Valley. He thinks of himself more as “a voice in the wilderness” and someone who brings together people with great ideas to build new things. In our conversation, we covered how to build a business with a real ethos, how to gain competitive advantage by doing the right thing, and why thinking beyond the quarter, or even the year, is crucial for survival.

As he said, “Companies need to think about the long term, which is: who is going to provide what you are the gatekeeper for if you basically have a relentless acquisition of all the value for yourself?” Ultimately, he believes – and I couldn’t agree more – that “we need to build an economy in which the important things are paid for in self-sustaining ways rather than as charities to be funded out of the goodness of our hearts.”

Other topics we touched on include:

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Where to find Tim O'Reilly:

• O’Reilly Media: https://www.oreilly.com/ 

• X: https://x.com/timoreilly 

• Facebook: https://www.facebook.com/timoreilly

• LinkedIn: https://www.linkedin.com/in/timo3/

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 

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In This Episode We Cover:

(00:43) Meet Tim O’Reilly

(06:25) How Eric and Tim met

(08:38) On not getting caught up in trends of the moment

(10:44) Tim’s early career and how his thinking evolved

(13:10) From open source to Web 2.0

(14:06) Working to make the world a better place

(16:11) How idealism is subsumed by the system we work in

(18:25) Resisting the lure of profit

(19:53) Thinking about companies as members of an ecosystem

(21:20) Creating versus capturing value

(23:38) Internet aggregators

(26:45) Choosing value creation over-extraction as a means of sustainability

(30:00) Ads and the lesson of screen placement

(32:49) AI and Google

(37:13) Values are a map of the world

(39:56) How to build a company ethos

(42:24) How adpoting values publicly makes them more powerful

(47:46) Dune

(49:31) Literature’s evolution

(50:21) Anthony Trollope’s proto-feminist novel, Can You Forgive Her? 

(49:30) George Elliot’s The Mill on the Floss

(51:22) The Dune movies

(52:39) Turning books into movies

(54:23) Tim’s favorite childhood books

(58:29) Why doing good is the best path to success

(1:02:22) Generative AI, value, and trust

(1:12:25) How idealists talk themselves out of it

(1:15:53) Lightning Round

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Production and marketing by ⁠⁠⁠⁠⁠⁠https://penname.co/⁠⁠⁠⁠⁠⁠.

Eric may be an investor in the companies discussed.

Stacy Brown-Philpot is a unique voice in Silicon Valley. She began her career as a public accountant and worked at Goldman Sachs before landing at Google.

She was the COO and then the CEO of TaskRabbit, which she saw through its sale to Ikea. Today, she’s on a number of corporate boards including HP, Nordstrom, StockX, Noom, and Black Girls CODE. She’s also a founding member of the SoftBank Opportunity Fund, which invests in Black, Latinx, and Native American founders.

Throughout, she’s been a consistent advocate for building cultures where people can bring all aspects of their rich and varied lives to work. The importance of setting out what you want to be and fully committing to it is the wisdom she’s held her entire life: “My grandmother's always telling me, if you don't stand for something, you fall for anything.”

In our conversation, we touched on Google’s rise and its eventual tumble from its “don’t be evil” ethos, what it was like to pioneer the sharing economy at Task Rabbit and the pivots the company went through along the way, and why selling the company to Ikea was dependent on its mission because “they weren't going to buy anything just to buy it. They needed to buy something that they believed in because they're only a part of something that they believe in.” 

Stacy’s model of compassionate leadership is inspiring, as is the fun she’s had executing it for the last few decades, even when things were bumpy. She had a lot to say about both, as well as:

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Mercury – The art of simplified finances. ⁠⁠⁠⁠⁠Learn more⁠⁠⁠⁠⁠.

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Where to find Stacy Brown-Philpot

• X: https://x.com/sbp04 

• LinkedIn: https://www.linkedin.com/in/stacyphilpot/

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 

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In This Episode We Cover:

(00:44) Meet Stacy Brown-Philpot

(05:11) The heyday of Google’s “don’t be evil” culture 

(08:01) Google’s IPO

(11:20) Stories from Google’s hyper-growth era

(13:44) The shift to backing away from idealism

(15:46) How the 2008 downturn changed Google’s DNA

(24:13) The difference between cultures at Goldman Sachs and Google

(29:43) Mistakes, apologies, and creativity

(31:18) Stacy’s transition from Google to TaskRabbit

(33:52) “the serendipity of what it means to be building something together”

(35:00) Navigating culture change at TaskRabbit

(42:31) Pivots at TaskRabbit

(46:08) Cutting categories and losing revenue for a longer-term goal

(47:35) Inside the TaskRabbit pivot war room

(48:59) Stacy’s stories of taking client and customer calls from her couch

(57:20) The Ikea acquisition and cultural alignment

(1:00:15) Ikea’s foundation ownership model and its “vertically integrated” mission

(1:01:27) Stacy’s reflections on her startup experience

(1:04:05) Stacy’s view of the board’s role in a company

(1:06:07) How she came to be on the board of HP and the companies that followed

(1:07:26) The pandemic at TaskRabbit and on the Nordstrom board 

(1:08:21) George Floyd 

(1:11:20) Stacy’s views on DEI, where we are now, and its cyclical nature

(1:14:45) Lighting round

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Eric may be an investor in the companies discussed.

The latest episode of The Eric Ries Show features my conversation with Reid Hoffman. Executive Vice President of PayPal, co-founder of LinkedIn, and legendary investor at Greylock Partners are just a few of his official roles that have changed our world. He’s also been a mentor to countless founders of iconic companies like Airbnb, Facebook, and OpenAI. He’s an author, a podcast host – both Masters of Scale and his new show, Possible, with Aria Finger – and perhaps most importantly a crucial steward of AI, including co-founding Inflection AI, a Public Benefit Corporation, in 2022.

Reid has also long been a voice of moral clarity and a stabilizing influence on the tech ecosystem, supporting people who are working to make the world a better place at every level. He’s a firm believer that “the way that we express ourselves over time is by being citizens of the polis – tribal members.” That includes not just supporting the legal system and democratic process but also building organizations “from the founding and through scaling and ongoing iteration to have a functional and healthy society.”

We talked about all of this, as well as AI, from multiple angles – including the story of how he came to broker the first meeting between Sam Altman and Satya Nadella that led to the OpenAI-Microsoft partnership. He also had a lot to say about how AI will work as a meta-tool for all the other tools we use. We are, as he said,” homo techne,” – meaning we evolve through the technology we make.

We also broke down his famous saying that “entrepreneurship is like jumping off a cliff and assembling the plane on the way down” and:

• The human tendency to form groups

• The relationship between doing good for people and profits

• AI as a meta-tool

• What he looks for in a leader

• The necessity of evolving culture

• Being willing to take public positions

• His thoughts on the economy and the upcoming election

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Mercury – The art of simplified finances. ⁠⁠⁠⁠Learn more⁠⁠⁠⁠.

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Neo4j – The graph database and analytics leader. ⁠⁠⁠⁠Learn more⁠⁠⁠⁠.

—

Where to find Reid Hoffman:

• Reid’s Website: https://www.reidhoffman.org/

• LinkedIn: https://www.linkedin.com/in/reidhoffman/

• Instagram: https://www.instagram.com/reidhoffman/

• X: https://x.com/reidhoffman

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 

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In This Episode We Cover:

(01:15) Meet Reid Hoffman

(06:01) The three eras of LinkedIn

(08:21) The alignment of LinkedIn and Microsoft’s missions

(10:39) The power of being mission-driven

(18:42) Embedding culture in every function

(21:08) The purpose of organizations

(23:45) Organizations as tribes for human expression

(29:08) Reid’s advice for navigating profit vs. purpose

(38:33) The moment Reid realized the AI future is actually now

(41:57) Home techne

(44:52) AI as meta-tool

(47:05) Why Reid co-founded Inflection AI

(49:53) The early days of OpenAI

(55:41) How Reid introduced Sam Altman and Satya Nadella

(58:26) The unusual structure of the Microsoft-OpenAI deal

(1:04:42) The importance of aligning governance structure with mission

(1:09:56) Making a company trustworthy through accountability 

(1:15:59) Inflection’s pivot a unique model

(1:19:53) Companies that are doing lean AI right

(1:22:52) Reid’s advice for deploying AI effectively 

(1:26:21) Being a voice of moral clarity in complicated times 

(1:31:26) The economy and what’s at stake in the 2024 election

(1:37:24) The qualities Reid looks for in a leader

(1:39:43) Lightning round, including board games, the PayPal mafia, regulation, and more

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Eric may be an investor in the companies discussed.