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Growing up on a farm in Finland near the Russian border, I had humble beginnings, doing manual labor like picking potatoes and feeding chickens. My parents were factory workers, so I had no professional role models. Getting a Commodore 64 before age 10 fueled my dream of creating something valuable for others. My move to America to build a company still feels unreal to my mom. After our IPO, instead of joy, I felt panic and disappointment. This was one of the lowest moments in my life. To address this, I attended a 10-day silent meditation retreat in Taiwan and have meditated ever since. Authenticity and vulnerability are key, striving to be the same person in all roles. During a Pacific row, I realized I had never truly observed my thoughts and emotions. This was a turning point, understanding that the mind needs reflection to stay on course. My mission is to help potentially billions restore their metabolic health by addressing obesity and diabetes, aiming to reverse diabetes globally. I prioritize sleep, averaging seven to eight hours a night, and treat myself like an Olympic athlete, focusing on the foundations of health and disciplined routines. Our goal is to make people healthy, not just sell drugs to treat symptoms of obesity and type 2 diabetes.

Tucker Carlson discusses Nancy Pelosi's stock trading with Chris Josephs, who created a stock tracker app focused on politicians' trades. Josephs, who previously worked in finance, started the app after observing the significant profits politicians made during the COVID-19 pandemic, particularly Pelosi, who has traded millions in stocks. Josephs highlights the corruption in Congress, citing Richard Burr's insider trading scandal during the pandemic as a pivotal moment that sparked public interest in political stock trading. Josephs explains how he and his co-founders built the app to allow users to follow and invest alongside politicians, emphasizing the hypocrisy of politicians profiting from insider knowledge. He notes that Pelosi's trades, especially in companies like Tesla and NVIDIA, have significantly outperformed the market, raising questions about the ethics of politicians trading stocks while in office. The conversation touches on the broader implications of political corruption, the lack of accountability for politicians, and the need for reforms such as banning stock trading for members of Congress and their families. Josephs argues that trust in institutions is eroding, and without transparency, society suffers. He also mentions the potential for a wealth transfer in the coming years as boomers pass down assets, stressing the importance of managing money in a way that aligns with personal values. Carlson and Josephs discuss the challenges of regulating political stock trading, the need for blind trusts, and the impact of social media in exposing corruption. They conclude that while the app profits from the current system, they advocate for reforms to restore trust in government and ensure that politicians cannot exploit their positions for personal gain.

Sahil Lavingia, born in New York to Indian immigrant parents, grew up in Singapore and studied computer science at USC. He began developing iPhone apps in high school, which led to his involvement with Pinterest after he created a popular app called Data. He joined Pinterest as employee number two in 2010, where he built the iPhone app and contributed to the early development of the platform. Despite initially planning to complete his degree, he left school to pursue this opportunity, believing it could serve as a valuable experience. Lavingia describes the early days at Pinterest as chaotic yet exciting, with a small team working in a living room to build a product that was gaining traction. He felt confident about Pinterest's potential for success, even as others cautioned him about the volatility of startups. Eventually, he started Gumroad as a weekend project, driven by the desire to empower creators to sell directly to their audiences without needing a complex setup. This idea resonated with him as he recognized a shift in how creators were connecting with their audiences. After building Gumroad, Lavingia faced the decision to leave Pinterest, motivated by the excitement of starting his own company. He raised initial funding from various investors, including Naval Ravikant and Max Levchin, and later secured a Series A round from Kleiner Perkins. However, growth was slower than expected, leading to challenges in raising further capital. Lavingia eventually bought out Kleiner Perkins for a dollar after the company struggled to meet growth expectations, which allowed him to regain control and pivot Gumroad towards profitability. Today, Gumroad processes around $150 million annually for creators and has achieved $10 million in ARR, doubling year-over-year. Lavingia emphasizes the importance of product-market fit, noting that the market's demand ultimately drives success more than the quality of the product or team. He believes in the creator economy's potential and the importance of community in building successful products. Lavingia also discusses his interest in crypto, expressing confidence that it will fundamentally change the economy and increase liquidity. He sees the potential for decentralized systems to disrupt traditional financial models, allowing for direct transactions between creators and consumers. He remains optimistic about the future of innovation, believing that as technology evolves, new solutions will emerge to address societal challenges. In his journey, Lavingia has also ventured into angel investing, focusing on supporting diverse founders and leveraging his experience to help others. He has set up a rolling fund to facilitate investments, reflecting a shift in how venture capital can be approached in the modern landscape. He advocates for transparency and community engagement in business, believing that sharing knowledge and experiences can lead to better outcomes for everyone involved.

Harry and Holly discuss Holly’s path to entrepreneurship and Shopify’s origins. Holly describes starting at 13 with a DJ dream, then selling t-shirts in Canada to support her family, moving to Ottawa in 2005 where she met Toby and helped build Shopify. She became one of Shopify’s first merchants, pursued law and an MBA to sharpen entrepreneurship, and in 2009 joined Toby’s team to launch Shopify to the world, noting that 'the software behind the snowboard business was more valuable than the snowboard business itself'. She frames COVID-19 as a catalyst for digitalization and resilience, contrasting resistance with resilience. She notes Shopify has served two million entrepreneurs and emphasizes entrepreneurship as a tool for survival when setbacks strike. She describes her grandparents’ immigrant story and how entrepreneurship helped her family, and she explains this mindset informs her approach to leadership and opportunity in tough times. On leadership and culture, she discusses listening and empathy: recording meetings, inviting later summaries, Slack notes, and changing practices to ensure clarity. She introduces the 'trust battery' for safe debate, and the 'disagree, commit' principle with Toby. She argues storytelling is a mission, not just a style, using Shopify signage and merchant stories to recruit and align people toward entrepreneurship. She cites High Output Management by Andy Grove and Ishigoi Ishii as helpful references. She shares personal life details: couple’s therapy with Lindsey, how listening versus solving changed their dynamic, and calendar-blocking date nights and family activities to stay present. She notes hiring a trainer to safeguard time with family, and prioritizing weekends with her kids to balance ambition with presence.

The discussion centers around Christina's journey from working at USV to founding Vanta, a successful security company valued at $2.45 billion. Christina reflects on her initial hesitations about leaving a stable job, feeling imposter syndrome, and the pressure of societal expectations. She emphasizes the importance of not counting oneself out and taking risks, as she did by quitting her job to learn coding and explore various projects, many of which failed. Christina shares insights on the creative process, likening it to making "bad art" to eventually produce something valuable. She highlights the significance of understanding customer needs and the necessity of validating ideas through direct engagement rather than assumptions. The conversation touches on the challenges of startup life, including managing self-doubt and the importance of maintaining personal well-being through activities like running and reading. Christina also discusses her approach to fundraising, noting that she preferred to build a solid foundation before seeking investment, which led to a successful Series A round. The discussion concludes with her thoughts on negotiation, emphasizing confidence and the importance of believing in one's value during discussions. Vanta aims to simplify security for startups, and Christina encourages others to pursue their passions and learn from failures.

Jack Zhang’s story begins with relentless hustle. He moved to Australia around age 15 after his family lost most of their money, surviving by working in a restaurant, a lemon factory in 40-degree heat, and overnight shifts at a petrol station while funding tuition of about 24,000 AUD a year. He built an early taste of entrepreneurship in high school with Urban Exploration, a magazine that attracted thousands of advertisers and generated real revenue. He later notes that decades of hard work formed the discipline and resilience that would drive his career. At university in Melbourne, he connected with three co-founders and juggled multiple jobs while studying computer science. They chased ideas from coffee shops to retail, but the core breakthrough grew from frustration with cross-border payments now dominated by clunky networks like SWIFT. They tested a peer-to-peer concept before pivoting when scale proved beyond reach. The first big break came when Lucy invested 2 million for 40% after a rapid dinner-law discussion; within days, the funds wired to a personal account. They committed to Airwallex, moved into a 10-square-meter office, and slept in a sleeping bag while building the business. Funding cycles proved turbulent. Australian venture firms initially rejected the pivot and the team, even as a banker investor wired money and later backed them. They moved from a fragile product toward a broader FX engine, connecting to interbank liquidity via McCory and negotiating sub-two-basis-point pricing for real-time trading. After a year of pivots, they secured a Series A led by Sequoia, Tencent, and Mastercard; a later Stripe acquisition offer of about 1.2 billion loomed but was declined. Hedosophia provided a convertible note during market downturns around 2020–2021, helping them survive while COVID intensified demand for cross-border flows. From 2021 onward, Airwallex evolved into a global banking platform. They expanded offices, built issuing and merchant-acquiring rails, and pursued product-market fit across regions. By late 2023, volume growth was rapid and annual recurring revenue crossed the hundreds of millions, reaching 500, then 600, then 700 million in early 2024. A roughly 6.2 billion valuation followed a string of rounds led by Sequoia, Mastercard, Tencent, and Hedosophia, while the company emphasized disciplined hiring, culture, and leveraging brand strength. The founder citesStripe’s Patrick Collison as a model and envisions Airwallex rivaling Citi or HSBC by 2035, powering millions of businesses worldwide.

From a journey that began with a machine learning PhD detour to a viral, AI‑driven video tool, Gaurav Misra built Captions into an AI powered creative studio. Born in Boston and raised in New Delhi, he grew up with a passion for programming and pursued engineering at Boston University. After interning at Microsoft and declining the software engineer in test path, he joined a Boston startup, Lattice Engines, where he worked on scalable ML for lead scoring. A brief PhD followed, then a pivot to industry: Microsoft on an ML platform, Localytics, and finally Snapchat in New York, drawn by rapid experimentation and prototyping. At Snapchat in New York, he joined a small engineering team that built an internal culture of experimentation. The New York team, led by Andrew Lin, functioned as a design‑engineering hybrid and used a skunkworks approach called Spooky to ship fast, isolated experiments. They prototyped features like Spotlight, a vertical video feed, and shipped a redesigned five‑tab navigation in production. The team also developed tools to measure and influence user behavior, such as eye‑tracking ideas and teleprompter concepts, and collaborated closely with Evan Spiegel’s design‑led product direction. After leaving Snapchat, Misra reconnected with Dwight—co‑founder of Captions—and their conversations in New York evolved into a shared opportunity around video creation. In 2021, they saw the rise of talking videos on TikTok and began with a social‑network concept, while Captions itself emerged as a practical tool. They built a transcription‑first editor in days; the app went to the top of the App Store overnight, powered only by Google API calls with no backend. Revenue appeared through a weekend paywall experiment, and personal ARR climbed to $500,000 with no employees, prompting a strategic pivot back to Captions. With Captions, the focus shifted to making video creation fast and approachable, starting with text‑based editing that lets users scrub by words, insert images, and trim precisely on screen. The team follows two roadmaps: a public list of must‑have improvements and a secret agenda aimed at changing behavior through innovative leaps. Eye contact emerged from teleprompter refinements, a feature later complemented by LipDub, which translates and lip‑synchronizes video across languages. GPT‑4 powers core translations, and hardware advances shorten training cycles, enabling faster iteration. The company is hiring in New York across disciplines as it scales the AI powered studio.

Alexis Ohanian, co-founder of Reddit, shares his journey from a history major at the University of Virginia to becoming a tech entrepreneur. After abandoning his LSAT exam for waffles, he decided against law school and pursued entrepreneurship. He and his roommate pitched an idea to Paul Graham, who later encouraged them to apply to Y Combinator. Although initially rejected, they pivoted their concept and received funding, leading to the creation of Reddit in 2005. They sold Reddit to Conde Nast in 2006 for $10 million, which felt surreal given their early struggles. Ohanian reflects on the challenges of running Reddit, including a lack of resources and the pressure to grow. He emphasizes the importance of community and user engagement, which helped Reddit thrive despite not evolving quickly. After stepping away from Reddit, he became a partner at Y Combinator and co-founded Initialized Capital with Gary Tan, focusing on early-stage investments. Ohanian discusses the significance of complementary skill sets and shared values in partnerships, highlighting the need for open communication and collaboration. He also addresses the evolving landscape of venture capital, emphasizing the importance of adapting to new technologies and trends, particularly in the crypto space. Ohanian notes that Initialized has invested in various crypto projects, including Coinbase, and believes in the potential of decentralized finance. Towards the end, he offers advice to young people entering the workforce, urging them to focus on skills that won't be automated and to consider trade schools as viable alternatives to traditional college. He concludes by expressing optimism about the future, particularly in how technology can foster community and innovation.

We always complain that we don't have a Google, Facebook, Amazon, or Tencent, or the most profitable companies in their clusters, and they're the biggest tech drivers next to VCs. But what we have in Europe is 90% of our companies are family businesses. They are highly profitable, they are run by entrepreneurs that can make fast decisions, take more risks, think long term, that have an incredible alpha knowledge in their domain, and that own global supply chains. If I have to put it into one sentence, I guess it's always being honest to myself to do what I love doing and really not compromising on it. I started my own small company in the mobile space, which I sold to Zalando, and then ended up doing Angel Investments. From those Angel Investments, we said, why don't we pull our money in a small seed fund? So that's how I started La Familia with a group of friends, which was a small 40 million Angel fund back then that we invested into 30 B2B companies. I thought maybe when I'm 50, 60, and in case I succeed, I could become a VC, but I never thought that I would kind of become an entrepreneur in VC in the middle of my 20s without any experience. The one thing you shouldn't do is compromise on the partnership setup because it's a very, very long term game. Visionaries within three years a great fun 600 million under management. The best mechanism that we put in place is that we hire people that we give 50 a job description of why we need someone and 50 we give them the degrees of freedom to use their time to really unlock what they love doing. Signaling risk is the biggest load of BS. We lead rounds at pre-seed and seed. We try to avoid investing into momentum companies.

Twenty-three years ago I started with a couple friends designing websites, and we built Basecamp to manage projects. Clients asked what it was; we turned it into a product, pricing it in February 2004, and about a year later it earned more revenue than our design work, so we stopped designing and focused on Basecamp and related products. I don’t like structure or being told what to do; I want independence and to run my own show. I’m planning a six‑week sabbatical to test distance from the work. On economics, it’s simple: if you don’t make more than you spend, you have to cut costs. We’ve been profitable for 23 years and run Basecamp without a board; we measure success by profitability and by whether we enjoy the work and would want to do it again. We’ve passed on aggressive scaling in favor of sustainable margins. Don’t worry about what others do; make your own business work and keep operating profitably, even if growth is flat. We discussed politics at work; Basecamp decided not to talk politics there, though private discussion was allowed. The public decision drew backlash, and about a third of the company left, with severance offered. Ultimately it was the right call. Our framework centers on disagree and commit, long‑term impact, and avoiding needless problems; focus on core fundamentals. We also debated Hey, launching a personal version first, and the compromise prevailed after deliberation.

What do entrepreneurs chase today that they shouldn't be chasing? It’s the wrong focus. If you chase everything else, it will work out, he says. He notes how hard fundraising is—“you will get rejected a lot,” and he pitched 100 investors to land his first backer. His first venture, a bootstrapped pool-table business, grew to about six million dollars a year selling online, a foundation for later choices. Childhood and early moves shaped his sense of purpose. He moved across Latin America as a child, which fostered empathy for outsiders and the willingness to think differently. He never drank alcohol, and he credits a two-year Mormon mission in Bolivia with grounding his mission to help others. The pool-table success funded college and marriage at twenty-two, adding responsibility and a lasting clarity about work and life. While in business school, he studied the Brazil opportunity and watched a path like diapers.com. They raised about $4.5 million on a PowerPoint, moved to Brazil, and scaled to 300 employees in 18 months, becoming the startup of the year in 2012. The cousin co-CEO relationship fractured; the business eventually failed after several years. He learned: identify your idea, then hire the best person to solve it, not a family member. That experience seeded Cotopaxi. A 36-hour reflection produced the Cotopaxi concept: a movement-driven outdoor brand fighting poverty, not just gear. Brand meaning comes from values and the why behind actions. He cites Warby Parker's advice: product comes first, mission differentiates later. They built a product foundation with designers, then partnered with factories; growth was fueled by investors, especially women-led rounds. The LDS faith shaped leadership, including giving and transparent impact reporting. During the pandemic, Cotopaxi stayed true to impact and cut salaries to preserve jobs; they donated 3% of revenue and later rewarded staff. He notes tension between mission and liquidity, and describes a failed push for permanent capital. He later transitioned from CEO to lead a church mission in Brazil, bringing in Damen Wong as CEO; he envisions impact and hopes to rally brands. He values balance as a father of four and finds guidance in Parables of Jesus Christ, and a tombstone word: Service.

These models right now are very focused on existing knowledge, right? So they learned all available public knowledge on the internet, and they were able to produce a result for you that is trying to predict what you're trying to answer. But then there's a question of what about new knowledge? What happens when those models start to hypothesize? They can come up with new ideas, new scientific discoveries. You know, imagine AI coming up with answers to some of the biggest scientific mysteries in the world, like what is dark matter, what's dark energy, what causes Alzheimer's disease, what is quantum mechanics, what is oneself? And that, for me, is you're moving from a place of those models are amazing in rebuilding and restructuring existing knowledge to coming up with new knowledge. When you start to come up with new knowledge, you're really talking about a whole new frontier. The idea that a professional community becomes a powerful growth engine for the economy deeply resonated with me. I became a LinkedIn fan long before I joined the company. I came to the valley in 2008 and heard Reid Hoffman talk about "the power of online professional communities and how it can create economic opportunities." The first time I heard it, and it deeply resonated with me. "The idea that a professional community becomes a powerful growth engine for the economy" just inspired me on a whole new level. And over time, Reid himself became a personal mentor of mine. I joined the company in 2012, and in 2020, I became the CPO myself. So it kind of felt, it kind of came full circle. "What are members truly looking for, not just functionally, but also emotionally," is a question I and the team use to shape innovation. The conversation about joining LinkedIn in 2012 and later taking on product leadership is framed by the belief that creating professional opportunity through community is central. The feed is positioned as a place where professional conversations matter, and the journey from a startup to a leading platform centers on that shift in focus—from generic discovery to meaningful, work-related engagement. The work of product at LinkedIn revolves around jobs to be done and human needs, not just features. The job to be done for creating on LinkedIn is really driving opportunity for you. There are many audiences, but Reid’s insight was that if I help people build their community in a professional way, there’s so much value they can drive from it. "The feed is first and foremost about people that matter to you talking about things you care about," and the emphasis on emotional and social needs informs how teams prioritize experiences and how success is measured across the ecosystem.