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I was 30, had never taken a business or marketing class, and I had never used PowerPoint. I bought a Mac to use Persuasion and tried to create a company presentation for venture capitalists. My first official day of work was my thirtieth birthday, February 17, and we got the company funded. We met every day, the three of us, in one founder’s townhouse in Fremont. There was nothing to do at first—just talking about what we did yesterday, what we had for dinner, or where to go for lunch. For several months, the big daily decision was whether to have Philly cheesesteaks or Chinese food, and eventually whether to put donuts in the fridge in the morning. That period lasted a few months. I read books about starting companies and tried to figure out how to raise money and what a venture capitalist is. I then met a lawyer at Cooley Godward who helped us incorporate. He asked how much money we had in our pockets; I said $200. He took $200 and got 20% of Nvidia for it. I went back to the house, and my two partners each gave me $200, each getting 20%. And that’s how it worked, liberally. I never finished my business plan. I know it. We never finished a business plan, to tell you the truth. If I had finished that thick Gordon Bell book, How to Start a High-tech Company, I would have been dead now; we would have run out of money and time. I read the first three or four chapters, then had to go to work. We incorporated, and they introduced us to two venture capitalists. I went to their office and explained what I wanted to do. The key to getting funded, I learned, is not a business plan; VCs don’t invest in business plans because business plans are easy to write. They invest in great people, and your reputation and history matter. Because I had done significant work with Andy Bechtolsheim, another Stanford graduate and founder of Sun, and because we had connections with the founders of Synopsys and LSI Logic, we were in a strong position due to our track record and relationships, even if my business plan writing skills were inadequate. Another crucial factor is the vision. They want to know there is a market large enough to justify the investment. The market size matters: if the market is $20 billion, an investment of $10 million may not be justifiable; but if the market is $200 billion, the dynamics are different. The size of the market is important, and having a clever idea that the market has never done before is compelling. Yet, the last point, perhaps the least important, is the market itself—because you may need to reinvent yourself over time. If you’re going to reinvent yourself, you need great people, which is why great people are so important.

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The speaker discusses notable figures and firms in Silicon Valley, focusing on Peter Thiel and the venture capital world. They begin by mentioning two cyber companies, Lookout and Palantir, and note that Palantir is Peter Thiel’s company. The conversation clarifies the spelling of Palantir and Thiel, though there is some back-and-forth about the correct letters. The speaker indicates that Thiel would put you on the board of Palantir, expressing that Peter Thiel is one of the best they’ve never met, and mentions that Thiel is expected to come here next week. The dialogue shifts to Andreessen Horowitz, the venture capital firm co-founded by Marc Andreessen and Ben Horowitz. The speaker explains that Andreessen Horowitz pays Larry a million dollars a year to advise them. The firm is identified as Andreessen Horowitz, with the correct spelling of the names confirmed. The conversation then asks what the firm is, and the answer given is that they are lobbyists. The speaker notes that Andreessen Horowitz are the biggest venture capital people in Silicon Valley, asserting they are bigger than Sequoia or Kleiner Perkins, describing them as the “new” power players in the industry. A broader characterization is provided: these two entities—Palantir (Peter Thiel’s company) and Andreessen Horowitz (the prominent venture capital firm)—are highlighted as pivotal players in the tech ecosystem. The speaker emphasizes the influence and reach of Andreessen Horowitz by describing them as the biggest venture capital people in Silicon Valley and comparing them favorably against other legendary firms. In closing, the speaker remarks that these two companies are key players to consider, suggesting that involvement with them would be significant within the next three weeks if there is a potential departure or change in status.

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Peter Thiel co-founded PayPal in 1998, leading a team that later launched influential startups like YouTube, Yelp, Kiva, LinkedIn, and Tesla. There's a perspective that one can be both a libertarian and collaborate with the government.

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This transcript presents an exchange highlighting how Jeffrey Epstein allegedly acts as a “fixer” to help former government officials convert their public power into private wealth as they leave office. Context and people: - The discussion centers on a February 2013 meeting involving Jeffrey Epstein, Ehud Barak (then head of Israeli military intelligence, later prime minister and defense minister), and Larry Summers. The timing is notable as Barak was transitioning to the private sector and leaving government work in March 2013. - Tom Pritzker (chairman of the Pritzker Foundation and head of the Hyatt chain) is referenced; the conversation references Tom Pritzker asking someone named Douglas about mentoring and a list of IOUs. - The speakers describe Barak’s career trajectory and Epstein’s role as a facilitator in converting government influence into private sector opportunities. Key claims and dynamics: - Epstein’s role as “outside fixer” helping a previously high-ranking official navigate the private sector and monetize government power. - The explicit strategy discussed: compile a “people index”—a list of people who owe you favors, owe you their lives, or owe you jobs. This IOU list is presented as the crucial asset for post-government opportunities. - The stated consequence: after leaving government, the official can secure lucrative board seats, funding from foundations and philanthropies, startup capital, and high-level consulting or venture capital opportunities, all because people owe favors from their time in government. - Barak’s situation is framed as an example of converting cresting government power into personal business leverage, with Epstein mediating connections to private-sector roles. - The conversation suggests Epstein has facilitated similar arrangements in the United States with CIA director Bill Burns, in the United Kingdom, and possibly with Saudi actors, framing this as a general pattern. - Specific monetization ideas discussed for Barak include pursuing board roles; Lookout (a cybersecurity company) is mentioned as a potential board opportunity that could pay “a couple million dollars.” - There is a mention of Palantir (Peter Thiel’s firm) being discussed in the context of Barak’s potential involvement, though Barak had not heard of Palantir at the time, and Epstein notes the possibility of approaching Thiel or related circles. - The dialogue compares Epstein’s brokerage function to a talent agent in the music industry—handling the money side, negotiations, and access to platforms—so that the individual can focus on the expertise itself. - The two cyber companies mentioned include Lookout and Palantir, with a note that Thiel’s Palantir was not familiar to Barak or Epstein at that dinner in 2013, despite Palantir’s 2003 founding. Additional context: - The dialogue references an attempt to reach Peter Thiel and to surround him with “spooks,” suggesting ongoing efforts to connect Barak and Epstein with Thiel’s network. - The overall theme is a firsthand depiction of how high-level government experience can be leveraged into private-sector power through a carefully curated network of IOUs and official-to-private transitions.

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Speaker 0 Summary: Peter Thiel, a co-founder of PayPal and Palantir, and an early investor in Facebook, is described as now worth about $8,000,000,000. He has focused a large portion of his fortune on building JD Vance. Thiel and Vance met in 2011 at Yale Law School after Thiel gave a talk; Thiel became Vance’s mentor, employer, and financier, funding Vance’s venture firm and writing the blurb on Vance’s book. In 2022, Thiel donated $15,000,000 to Vance’s Senate campaign—the largest individual donation to a single Senate race in American history. He escorted Vance into Mar-a-Lago personally and introduced him to Donald Trump, despite Vance having previously called Trump “Hitler.” The transcript notes Thiel has stated publicly, and it is claimed here as a quote, that “I no longer believe that freedom and democracy are compatible.” Epstein files and connections: Thiel’s name allegedly appears over 2,200 times across Epstein’s email schedules and documents. The transcript says Thiel and Epstein lunch together in November 2017, nine years after Epstein’s conviction for soliciting prostitution from a minor. Epstein invested $40,000,000 into funds co-managed by Thiel, and Epstein reportedly brokered introductions between Thiel and Israeli officials, including arranging a 2014 dinner. Thiel denies wrongdoing, though the calendar entries cited do not express opinions. Palantir and government ties: Palantir, Thiel’s company, signed a strategic partnership with Israel’s Ministry of Defense in 2024. Palantir’s CEO publicly stated pride in supporting Israel “in every way we can,” and has acknowledged that their product is used, on occasion, to kill people. The transcript emphasizes Thiel as “the man who built your vice president,” asserting he is “the company in the bloodstream of your government.” It concludes with the line, “You didn’t vote for Peter Thiel, but Peter Thiel is governing you anyway. That’s not democracy. That’s a purchase.”

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- The speaker argues that college is not primarily for learning; everything can be learned for free, and the main value of college is demonstrating hard work through assignments and providing a social environment for a period of time. They also note a need for evidence of exceptional ability, suggesting that attending college is not itself evidence of exceptional ability and that some highly successful people (e.g., Gates, “Java,” Larry Ellison) dropped out. - Education should resemble a video game: make learning interactive and engaging, and disconnect grade levels from subjects so students can progress at their fastest pace or at their own interest level in each subject. - Much of current teaching resembles vaudeville: a lecturer delivering the same talk year after year, not necessarily engaging, which reduces effectiveness. - Peter Thiel’s view is referenced: a university education is often unnecessary, though not for all people. You typically learn as much in the first two years as you will later, much of it from classmates. For many companies, completion of a degree signals perseverance, which can matter depending on the goal. - If the goal is to start a company, finishing college may be pointless. The idea is that education should not treat people as assembly-line objects moving through standardized English, math, science sequences from grade to grade. - Ad Astra is a small school created by the speaker for their five boys (and growing to 14 now, 20 by September), named meaning “to the stars.” It departs from traditional grading: there are no grades, no grade-by-grade progression, and education is tailored to individual aptitudes and abilities. The school emphasizes teaching problem solving or problem-based learning rather than teaching tools first—e.g., for engines, students start with the engine and learn which tools are needed to disassemble it, rather than teaching about screwdrivers and wrenches in isolation. - Students respond positively: the kids enjoy going to school and even think vacations are too long, indicating high engagement. The speaker notes that education should be more gamified and engaging, rather than a chore. - The speaker critiques conventional education as downloading data and algorithms, implying it’s tremendously inefficient and often unnecessary to learn some topics for future use, reinforcing the need for a problem-centered, engaging approach.

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I had a lot of freedom growing up and dropped out of school at 12. I convinced my mom to let me stay home, and I was self-directed. By high school, I was in a program for troubled kids. I wasn't a good student and focused on my interests. I was philosophical and read existentialism. I don't see myself as just an entrepreneur. I had a successful company but it's not my identity. I had the biggest website and sold it for a lot of money.

The BigDeal

$250 Million Founder: What I Did Wrong & How To BUILD BIG | Ankur Nagpal

Guests: Ankur Nagpal

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Ankur Nagpal, CEO of Carrye and former founder of Teachable, describes rising from nothing to building two companies and selling one for 250 million dollars. He recalls earning money in college with side ventures, including Facebook apps and the Disney Princess quizzes, at times generating up to 50 Grand a day for millions of teenagers. He moved from India to the United States, grew up in Oman, and attended Berkeley after being rejected by every Ivy League school. His early career included fundraising by directly messaging investors; he raised about 70 million on Twitter, with backers including Tiger Global. He explains that real skin in the game helped close rounds: he took zero management fees and offered a quarter of the capital to himself, which investors saw as credibility. He notes that meeting with people and showing progress mattered more than pedigree, and that he valued hiring people who are hungry to win rather than just mission-driven. Teachable's sale occurred during the stock market crash of 2020; 'the single biggest drop in market history.' The deal was announced as COVID began to feel real; Teachable had about 25 million in ARR and then doubled to 50 million ARR within three months. Nagpal reflects on the irony of selling into a crash while revenue surged, grateful for gains but not lamenting what could have been if waited. He notes the sale was a half-cash, half-stock deal and that ownership at the time allowed him to view the exit as 'infinite money' yet pursue new challenges for the love of the game. Carrye operates in a regulated space and currently custodys over $100 million in customer assets, with a little over $2 million in annualized revenue. Nagpal explains a culture of intense office work with a one-month remote policy to counter winter doldrums. He notes that distribution and compliance are essential in a world where AI lowers build costs, but regulators remain real. Branding is costly too; he paid for carry.com and believes brand can evolve later.

20VC

George Sivulka, Co-Founder & CEO @Hebbia: The Future of Foundation Models | E1250

Guests: George Sivulka

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George explains that great founders tend to come from three backgrounds: a messed-up childhood, being publicly gay, or being adopted. He cites Elon Musk as an example of the first, Jeff Bezos and Steve Jobs as adoptees, and Peter Thiel and Sam Altman as publicly gay, arguing these early-life experiences fuel a deeper drive to prove themselves. He also shares his own background: born in Staten Island, raised around New York City, math-oriented, a quiet kid who hacked school tablets to run StarCraft, and driven by a desire to surpass expectations and build something meaningful. His path includes a near-mythic NASA-scouting audition: he wanted a NASA internship, got rejected five times, then cold-queried NASA Goddard and, after a snow day, pressed through until he worked for free, published research, and earned Stanford admission. He describes sleepless, frugal years in a closet-like setup while launching Hebbia with a pre-seed from Peter Thiel and Floodgate and a seed from Mike Volpi at Index. He explains Rag—retrieval augmented generation—and Hebbia’s breakthrough: producing a productionized semantic search that answers questions about data, not just finds it. Hebia’s growth shifted as customers demanded answering questions about data rather than merely finding items; they built Studio, the first productionization of retrieval-augmented generation, and the first semantic search engine in 2020. They raised a 30-million-dollar Series A; later, they expanded through matrix-inference scaling, optimizing for accuracy over speed and stressing that value comes from how AI helps people, not from glossy demos. George argues platforms, agents, and apps will coexist; Heia aims to be a universal orchestration layer, scaling at inference and driving real enterprise value.

My First Million

The Crazy Story of Google’s 7 Angel investors

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In this episode, hosts Saam Paar and Shaan Puri explore the early investors in Google, highlighting the unique stories of seven individuals who made significant contributions to the company. They begin with the "karma building" at 165 University Avenue in Palo Alto, where Google was founded, alongside other notable companies like PayPal. The first investor discussed is Andy Bechtolsheim, co-founder of Sun Microsystems, who, after a brief meeting with Google founders Larry Page and Sergey Brin, wrote a $100,000 check to "Google Inc." without even a formal valuation, ultimately owning 2% of the company. Following him is David Cheriton, a Stanford professor who also invested $150,000, later becoming a billionaire through his shares. Ron Conway, another key figure, is introduced as a legendary angel investor known for his generous approach to helping founders. He invested in Google after being introduced to it by Cheriton at a holiday party. Conway's philosophy centers on supporting entrepreneurs, which has built his reputation and network in Silicon Valley. The discussion also touches on other notable investors, including Shaquille O'Neal, who accidentally invested in Google after a chance encounter, and Susan Wojcicki, who rented her garage to the Google founders and later became the CEO of YouTube. The hosts emphasize the importance of proximity in Silicon Valley, where casual interactions can lead to significant opportunities. They conclude with reflections on the nature of investing, the unpredictability of valuations, and the importance of recognizing potential in founders and ideas quickly. The episode encapsulates the serendipitous nature of early-stage investing and the transformative impact of these initial investments on the tech landscape.

Relentless

Why Momentum Is So Important In Startups | Joshua Browder

Guests: Joshua Browder

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Joshua Browder’s conversation in Relentless centers on momentum as the lifeblood of startups and how his own journey with Do Not Pay (and Browder Capital) illustrates the power of framing, timing, and relentless experimentation. He recounts early experiments in software as a teen—jailbreaking themes, crafting a Pret A Manger app, and accidentally securing an official feature through Apple after signing consent forms as a teenager—events that seeded his belief that momentum comes from visible progress, user traction, and audacious, practical demonstrations of value. The discussion then pivots to fundraising struggles after the Facebook-era “house of momentum” phase, where a few reframe-and-demo refinements—adding logos, creating a live product demo, and shifting to a subscription model—transformed a cascade of rejections into a decisive investor rush, underscoring how small framing changes can catalyze big outcomes. The core of the episode emphasizes the way Browder measures and mentors momentum in others. He describes his approach to selecting founders who possess an irrational drive paired with a personal connection to the problem, citing Adam Guild and Jake Adler as examples of founders who embody that spark. He also reflects on his own evolution as an entrepreneur and investor: from a public-service impulse for Do Not Pay to a sustainable, growth-oriented business that pays dividends and operates with a for-profit mindset. He argues that experience running a company in a fast-changing environment—AI, platform politics, 30% app store economics—gives him practical intuition that purely theoretical frameworks cannot provide, a stance that informs his investment decisions at Browder Capital. The interview also probes Browder’s views on youth, technology, and the ethics of automation. He warns against outsourcing thinking to AI, emphasizing human judgment and a grounded, day-to-day operational mindset. The broader thread connects his advocacy for consumer rights with pragmatic business strategy, including how to adapt business models to evolving markets and maintain momentum through consistent proof points, intentional storytelling, and access to capital. Finally, Browder opens up about personal resilience, dyslexia/dyspraxia, and the value of mentorship and pay-it-forward culture in Silicon Valley, framing momentum as something cultivated through people, products, and persistent, disciplined action rather than pure luck. He also shares lighter, illustrative anecdotes—his interview with Warren Buffett, the inspiring yet risky Pret app detour, and the transformative breakfast with Mark Andreessen—that illuminate how pivotal moments and strategic framing can unlock opportunities and scale a mission-driven company into a durable business.

Relentless

#11 - Siqi Chen, CEO Runway

Guests: Siqi Chen

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Siqi Chen, co‑founder of Serious Business, Hey Inc, and Runway, walks through a career shaped by hands‑on building, intense iterative experimentation, and an enduring insecurity about being a “real” founder. He recalls his earliest coding when his father gave him Visual Basic 4.0 in sixth grade, creating simple games like a Minesweeper variant and Lights Off on an old 386, experiences that proved pivotal in seeing software as a craft you could build and sell. Chen describes his first paying work in college with NASA on machine vision for Mars rovers, but his first entrepreneurial product—Friends for Sale on Facebook in 2007—was where he truly learned about monetization, distribution, and the surprise of people paying for virtual goods long before microtransactions were mainstream. The discussion reveals the tension between technical prowess and business acumen, a theme that follows him from Zynga’s acquisition of his company to his own admissions of imposter syndrome and the paralysis that can accompany big strategic decisions. Chen explains how Zynga’s approach to execution and the concept of “free R&D” shaped his understanding of competition and scale, and how a pivotal conversation with Mark Pincus reframed his view on building durable, reachable businesses. He shares the dynamics of building and exiting Heyday and the ethics of product decisions—why he and his co‑founders steered away from acquisition offers because they believed in a longer‑term vision, only to confront the reality that the next “big thing” must be sustainable and not simply “cash‑grabby.” The interview delves into his transition to Runway, the choice to pause and reallocate during financial stress in 2020, and the emphasis he places on meaningful work, collaboration, and the human aspects of leadership. He reflects on the culture of Silicon Valley, the influence of peers, and the ongoing struggle with ego and insecurity, concluding that the best leadership emerges from choosing priorities that support the team and the product over personal acclaim, even in the face of massive, sometimes painful change. topics - Silicon Valley startup culture and fundraising rituals - Facebook games and early social networks - venture capital dynamics and exits - product leadership, design, and user psychology - resilience in tech entrepreneurship and pivots - hardware and VR implications in startup strategy - the psychology of insecurity and ego in founders - memory and time-based apps versus sustainable distribution

20VC

Markus Villig, Founder @Bolt: The Most Insane Story in Startups & The Future of Self-Driving| E1225

Guests: Markus Villig

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Marcus recounts a long startup journey that begins in Estonia, pivots toward building Bolt, a ride‑hailing and mobility platform, and culminates in a global expansion with a lean, data‑driven playbook. He grew up with parents who survived Soviet oppression and encouraged risk-taking, pursued software and commerce, coded for local firms, and sold collectibles. At 19, with no driver’s license, he identified transportation as a space of mass change driven by on‑demand assets, electric vehicles, micro‑mobility, and eventually self‑driving. Observing taxi industry failings—long phone queues, dirty cars, cash payments, rude drivers—he believed a better app could fix it. He validated consumer interest with surveys and then pitched drivers at taxi stands; many declined, but about 50 joined after persuasion, modest commissions, and a push to prove the concept. The early focus was driver onboarding and product development alongside a co‑founder search that yielded Oliver, who built the rider app and back end quickly. Marcus notes he was lucky to find Oliver, and that initial co‑founding success felt almost fateful. He could have accelerated growth with a small angel round, but bootstrapped with 5,000 from his parents, prioritizing frugality and equity over cash. The market was harsh: consumer demand grew, but drivers were scarce, requiring on‑the‑spot recruitment and relentless iteration in a hostile environment for a 19‑year‑old founder. There was a chicken‑and‑egg problem in marketplaces. Bolt launched in Estonia and tried to enter ten markets in parallel with just 1 million in seed funding, burning cash and nearly bankrupting the company. After trimming back, focusing on one market at a time, and learning from early wins, they later raised a modest seed at about a 9 million valuation and began international expansion. The team learned to sequence city launches, prioritize the supply side, then scale demand, and stay focused on unit economics and ROI across geographies. Johannesburg went from zero to more than half the business, powered by a local student who ran the operation from scratch. Bolt’s African push used rapid, low‑cost online ads to unlock demand and a surprisingly strong supply side. Cross bookings became the North Star metric, arguing that negative early unit economics are typical in marketplaces due to network effects, requiring subsidies on both sides to reach critical mass before profitability follows. Africa demonstrated the value of localized, cost‑efficient market entry and a pragmatic, data‑driven launch playbook. During the COVID, Bolt faced an 85% revenue drop but did not lay off staff, enacting a 20% salary reduction and cash conservation while expanding new markets as lockdowns eased. A global “war room” coordinated market openings, enabling hundreds of thousands of drivers to sign up and markets to rebound. The company then raised large rounds, including Daimler’s 100M+ investment, to accelerate expansion, while preserving the frugal ethos that powered early wins.

20VC

Alex Rampell: The Best Founders Materialise Capital, Customers & Labour | The Future of Venture

Guests: Alex Rampell

reSee.it Podcast Summary

Alex Rampell argues that the best founders are those who can materially deploy capital, labor, and customers, effectively turning people and resources into scalable leverage. He likens venture investing to buying out-of-the-money call options, where the goal is to secure a stake in companies that could become immense if their strategic advantages compound. Rampell emphasizes that the current venture landscape rewards large, specialized or very small, highly capable firms, while mid-sized, generalist funds struggle to compete. He notes the shift toward later-stage investing, with major growth funds expanding, and discusses how technology firms now permeate every sector, threatening incumbents that fail to modernize with software at their core. The central challenge for VCs, he says, is selecting entrepreneurs who can sustain momentum and who exhibit extraordinary agency, deep domain knowledge, and a track record of learning from history, while maintaining a clear path to meaningful ownership that aligns incentives across founders and investors. A recurring theme is the distinction between “hostages” and “customers.” Rampell explains that true hostages—data-rich, deeply integrated offerings that are hard to replace—become the durable moat for application-layer software in a world where AI lowers switching costs. He argues for greenfield opportunities where many new companies are created and can choose the best product, versus slower markets where incumbents dominate. This drives his three-pronged thesis: invest in systems that anchor new firms and their data; back software that substitutes labor, delivering outsized growth; and pursue “walled garden” strategies that rely on unique data assets or revenant platforms. Throughout, he stresses founder-capital fit and the risk of over-optimizing with excessive capital, warning that moral hazard and diluted incentives can erode a startup’s path to a meaningful public outcome. The conversation reflects on the practicality of fundraising, the timing of follow-on rounds, and the tension between ownership and velocity when chasing the next big breakthrough. Toward the end, Rampell reflects on lessons learned from past investments, the importance of humility, and the inevitability that software will eat more of the world. He remains bullish on AI-enabled platforms, while acknowledging the need for discipline to avoid misallocated capital and to preserve incentives for long-term value creation. The chat closes with a candid look at how to navigate liquidity, price discipline, and strategic exits in a hyper-competitive environment, reinforcing that the most enduring bets come from people who combine extraordinary ambition with a deep understanding of their space and a readiness to act decisively.

20VC

Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN

Guests: Jack Zhang

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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.

Sourcery

Inside the $750B+ Thiel Fellowship

Guests: Danielle Strachman

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The episode centers on the Teal Fellowship and its evolution into the 1517 venture framework, as recounted by Danielle Strachman. She describes the fellowship as a two-year program offering substantial resources to exceptionally young people pursuing a wide range of projects, from startups to research and nonprofits. A core concept is hyperfluency, the ability to speak across technical and non-technical audiences, which the organizers believed helped wire Fellows to become ambitious and capable founders. The discussion delves into how the program measured potential: early applicants under twenty, questions about contrarian beliefs, long-term goals, and a final in-person evaluation that compared energy levels after conversations. The conversation underscores the emphasis on individualized mentorship, peer community, and flexible use of funds over rigid reporting. The narrative moves from the initial, almost accidental formation of the fellowship to its long-term outcomes. Notable Fellows like Dylan Field of Figma, Ritesh Agarwal of Oyo, and Laura Deming are highlighted as evidence of the program’s ripple effects, including the emergence of companies, lasting networks, and new career pathways. The hosts discuss how the fellowship fostered a culture of bold experimentation, such as a 17-year-old envisioning a longevity-focused venture fund and a young Ethereum founder pre-sale post that later became a visible milestone. The emphasis on “going beyond two years” and supporting alumni with ongoing mentorship and informal networks helps explain why many Fellows continue to influence technology and entrepreneurship long after the program ends. A substantial portion of the conversation examines pedagogy, culture, and the evolving ecosystem around youth-led innovation. Strachman details how the fellowship’s structure resembled homeschooling in its personalized approach: mentors, Socratic dialogue, and a community-centric model that valued peer interaction and real-world practice over formal schooling. They describe retreats, group housing, and informal rituals like games that build trust and collaboration. The episode also touches on the challenges of media scrutiny and the shifting attitudes toward nontraditional education paths, concluding with a sense of optimism about younger generations driving deeper tech exploration and new models of patronage and support.

My First Million

4 A.I. Business Ideas To Start Using Dall-E, GPT3 & Deepfake Technology

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The hosts, Saam Paar and Shaan Puri, discuss emerging trends in technology, particularly the potential of AI to disrupt various industries. They emphasize the importance of starting now to capitalize on these trends, as the technology is becoming increasingly capable. Saam shares a personal experience of dining with comedian Hassan Minhaj, highlighting Minhaj's intelligence and storytelling ability, which inspires Saam to seek ways to improve his own humor and storytelling skills. They discuss resources like a YouTube video by Mark Normand on joke writing and the Charisma on Command channel, which offers tips on charisma and social skills. The conversation shifts to the advancements in AI, specifically mentioning programs like DALL-E, which generates images from text prompts, and deepfake technology that can create realistic audio and video. They explore the implications of these technologies, including the potential for creating fake speeches and essays, and the disruption of traditional marketplaces for stock images and patterns. Saam shares ideas for AI-driven businesses, such as automated voiceovers and AI-generated student essays, while also acknowledging the competition that will arise in these spaces. They touch on the Thiel Fellowship, which offers funding for young innovators to drop out of college and pursue entrepreneurial ventures. Saam highlights successful outcomes from the fellowship, including Ethereum and Figma, and reflects on the high potential of young, talented individuals. The discussion concludes with thoughts on the future of Twitter as a platform for building empires, suggesting that serious dedication to content creation could lead to significant success, similar to what has been seen on other social media platforms. They emphasize the need for authenticity, collaboration, and a long-term commitment to succeed in this evolving landscape.

My First Million

Reddit IPO: 8 Startup Lessons For Any Entrepreneur Starting Out

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The podcast unexpectedly discusses Reddit going public, sparked by Paul Graham's essay on the platform. Graham, founder of Y Combinator (YC), reveals that Reddit was the first company in YC's inaugural batch and the reason YC was created. He recounts how Reddit's founders, Steve Huffman and Alexis Ohanian, traveled from Virginia to attend his talk at Harvard, demonstrating the importance of showing up. Initially, Graham rejected their idea for a food delivery service, but later accepted them into YC after realizing he should bet on people, not ideas. Reddit's name was initially a placeholder, and they gained traction by creating fake accounts to submit content, addressing the "chicken and egg" problem of community engagement. Despite its success, Reddit has faced challenges, including leadership changes and profitability issues, yet remains a major social platform with millions of daily users.

The Pomp Podcast

Pomp Podcast #274: Alexis Ohanian on Building and Investing in the Modern Digital World

Guests: Alexis Ohanian

reSee.it Podcast Summary

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.

20VC

Duolingo Co-Founder, Severin Hacker: How AI Impacts the Future of Work and Education

Guests: Severin Hacker

reSee.it Podcast Summary

Dualingo's mission is to provide the best education and make it universally available. From day one, Dualingo was technology first; back then it was software, and now we call it AI. We were one of the launch partners of OpenAI when they first launched Chip D4 and we immediately saw the potential of this technology to help our mission. The first insight was that AI could accelerate content production. It took us what we recall as twelve years to build the first 100 courses, and within one year we built another 148 more. That acceleration changed what we could deliver and how quickly we could scale the platform. Two things became clear about AI inside Duolingo. First, content generation is transformative; 'there's a lot of the sentence content within these courses' now produced with AI, and the curriculum design remains human-made. Second, new AI features were possible—like Lily, the interactive video call with a purple-haired character who remembers you and speaks in a natural way. Third, AI also boosts productivity company-wide. They mention ‘content generation’ changing learning content, ‘video call with Lily’ as a feature, and general productivity tools. They see personalization as the future of education and expect it to be multimodal—voice, typing, video, and dynamic, on-the-fly course design that adapts to you. On strategy and markets, the founders discuss fundraising and resilience. ‘It's harder to raise 3 million than 100 million,’ and the Series A was 3 million at 15 with Union Square Ventures leading; there was ‘one offer,’ Union Square or back to university. They contrast the push to relocate to SF with their success staying in Pittsburgh; Europe at the time wouldn't have supported similar growth. They credit Union Square for legitimacy; while marketing had been lean with ‘the green owl’ and ‘unhinged things’ that built a strong brand, they underpriced their brand—‘dramatically underprice brands’—yet built a highly efficient marketing machine. They explain why they didn't monetize early and how monetization is now essential but done with a mission to keep learning accessible. Regarding education's future, they frame higher ed as three things: instruction, credentials, and social networks, and they discuss the chess course as proof of AI-enabled development: prototype in nine months, then integrated into the app. They emphasize the secret sauce as not a single feature but a process, with retention driven by the streak. They discuss the social dimension—potential social features and Duo social, or even 'Duo dates'—and the ongoing balance between founder-driven detail and delegation. They assert that AI will augment humans, not replace them, while stressing the enduring value of motivation, guidance, and credentials in education.

20VC

Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153

Guests: Dan Siroker

reSee.it Podcast Summary

I very much believe you should either be in fundraising mode or not. Always saying the highest price is almost certainly going to be a mistake. When an investor asks how much are you raising, more often than not, they're actually asking how much do you think you're worth. Let's start the negotiation on valuation right now because 20% is what they want. I owe my mom's boss, Professor Hector Garcia Molina, a Stanford professor, who helped me access the latest computers at home, which propelled me toward technology. The highs and lows shape you, and a big yes came eight years ago when my wife said yes to getting married, which I rate far higher than any VC yes. Dan reflects on pivots and founder journeys, stressing that the two common patterns he cherishes are early glimmers of hope and the sense that a pivot should feel like coming home. He recalls the view that “things that work tend to work really fast,” and Dalton Caldwell’s idea that “a good pivot feels like coming home.” He emphasizes that portfolio pivots should preserve core problem focus, and that you should test with glimmers of hope before abandoning a path. This mindset underpins his approach to experimentation, where he asks founders to forecast plausible experiments and to pivot when those experiments stop yielding even incremental evidence that the path is viable. He and the host discuss the value of serial entrepreneurship versus first-time founders. Focus is central: “Focus. Focus, that's a huge one.” He notes that the main skill is remembering “the main thing is the main thing” and that clock speed matters in zero-to-one progress. He explains that investors prefer founders who stay with a mission, and he argues that the best investors are those “on the rising Arc of their career.” He also reflects on hiring, accountability, and maintaining involvement to avoid abdication, insisting you must be relentlessly in the details where impact is highest while empowering others to execute. The fundraising process is examined in depth. He advocates casting a wide net and being strategic about timing and terms: “We cast a wide net,” and explains turning down high offers for the right partner. He shares concrete data: “we had offers actually 22 offers at a billion dollars. We turned them down and took 350,” with several bids in the 200–400 range and a few outliers at a billion. He highlights negotiating empathy with investors, the importance of clear board governance, and the value of liquidity options for employees, including allowing vesting sales up to 25% of vested stock to improve retention and alignment.

20VC

Adarsh Hiremath @ Mercor: The Fastest Growing Startup in Silicon Valley | E1261

Guests: Adarsh Hiremath

reSee.it Podcast Summary

The round is 100 million and the price was at 2 billion. We'll live in a world with many models with different use cases. The recruiter is the one who controls the talent inflows and outflows of every company, and you can gather all you need to know about a company from those inflows and outflows. The businesses that succeed when software costs approach zero will be built on network effects. At the time it wasn't obvious that we should drop out, and I sympathize with my parents for not approving because there was no teal Fellowship. The moment I knew I wanted to drop out was back when we had an office in Paula walto. We were 19. We raised over 3 million; General Catalyst led the round. The money was wired and we changed our salaries in Gusto. Net retention is over 100%. There's not a single person who works on sales at Meror. We leverage llms and all these models throughout our product, and data is the bottleneck.

Relentless

#32 - Jakob Diepenbrock, Discipulus

Guests: Jakob Diepenbrock

reSee.it Podcast Summary

Jakob Diepenbrock, founder and GP of Discipulus, recounts building the first hard residency in El Segundo and turning a scrappy, two-week accelerator into a growing venture network for hard-tech founders. The conversation traces his path from early fireside chats and sponsor-driven events to launching Cohort 1 in a garage and Cohort 2 in a shared office space, with a focus on hands-on culture, intense but short programs, and a tight-knit cohort where participants sleep in the office and share workspace. Jakob explains how the initial events attracted sponsors like 1517 Fund and Contrary, and how he saw El Segundo as a better cultural fit than San Francisco for hardware-focused, nation-critical ventures. He reflects on the lifespan and economics of the program, weighing traditional fund structures against operating companies, and ultimately deciding on a standard fund model to preserve clear incentives, tax handling, and governance. He describes the fundraising grind: at first, small nonprofit money and a few 5k–25k checks, followed by a more traditional, momentum-based push that took time to materialize, aided by advisers and high-net-worth introductions. A recurring theme is the power of the network: Discipulus’ differentiator is access to founders and investors who would not travel to SF, and Jakob emphasizes the value of being “in the room” with the right people to evaluate hardware and mission-critical ventures. The interview highlights how the batch structure—kept small (two weeks, potential for more batches if demand grows)—prioritizes connection, mentorship, and speed, rather than long-form programs. Jakob reflects on personal growth, the learning curve of fundraising, and the importance of credibility and consistency as the network expands and inbound interest surges for future cohorts. topics Discipulus, hard tech, venture capital, accelerator models, El Segundo, hardware startups, networking, fundraising, batch size, two-week program otherTopics Founder stories, early-stage funding challenges, advisor networks, strategic positioning vs. YC-style programs, regional ecosystems, logistics of running a small accelerator booksMentioned

The Rubin Report

Trump, Gawker, and Leaving Silicon Valley | Peter Thiel | TECH | Rubin Report

Guests: Peter Thiel

reSee.it Podcast Summary

Peter Thiel, co-founder of PayPal and early investor in Facebook, discusses his journey and insights on technology, politics, and societal changes with host Dave Rubin. Thiel reflects on his partnership with Elon Musk during the inception of PayPal, emphasizing the innovative approach they took to link money with email, which allowed for rapid growth and user adoption. He notes that the success of PayPal stemmed from understanding the need for a seamless payment system, particularly for small transactions on platforms like eBay. Thiel shares his perspective on the evolution of Silicon Valley, noting a shift from a libertarian ethos to a more conformist culture. He expresses concern over the groupthink that has emerged, suggesting that the political landscape has become increasingly polarized and that the tech industry has lost some of its innovative edge. He argues that the current political climate stifles diverse ideas and that many in Silicon Valley feel pressured to conform to prevailing ideologies. The conversation shifts to Thiel's involvement with Facebook, where he was the first outside investor. He describes his initial meeting with Mark Zuckerberg and the rapid growth of the platform, highlighting Zuckerberg's unique ability to understand and adapt to the needs of users. Thiel emphasizes the importance of diverse ideas in fostering innovation and critiques the current state of political correctness that he believes hampers open discourse. Thiel also discusses his views on the future of technology, particularly regarding AI and cryptocurrency. He posits that while AI could enhance authoritarian control, cryptocurrencies represent a push towards decentralization and individual empowerment. He expresses optimism about the potential for new governance models, such as seasteading, which could allow for experimentation with different political systems. The discussion touches on the media landscape, with Thiel reflecting on his legal battle with Gawker, which he views as a defense of privacy rights against media overreach. He critiques the current media environment for its sensationalism and lack of accountability, suggesting that the decline of traditional media monopolies has led to a chaotic information landscape. Thiel concludes by encouraging young people to seek their own paths rather than follow established tracks, advocating for a focus on individual interests and ideas rather than competition. He stresses the importance of looking beyond immediate surroundings to find inspiration and meaning, suggesting that true progress comes from transcending conventional wisdom and embracing diverse perspectives.

Relentless

#36 - Solving Health Using AI | Max Marchione, Superpower

Guests: Max Marchione

reSee.it Podcast Summary

In this Relentless episode, host Ti Morse chats with Max Marchione about the frontier of health optimization through AI, first principles thinking, and radical experimentation. Max argues that secure data, continuous wearables, and multiomics will enable an AI doctor to predict and tailor care far beyond today’s episodic approach. He envisions a future where individuals use a blend of research compounds, supplements, and carefully chosen lifestyle hacks, while always validating choices against personal experience and measurable outcomes. The conversation threads through practical routines, from his morning rituals and a nutrient-dense smoothie to Sleep stacks, L-theanine, and nicotine as cognitive aids, all framed as individualized experiments rather than blanket medical advice. The discussion then broadens to how to build a health-tech platform that can scale into a hundred- to a hundred-billion-dollar company. Max emphasizes a long-horizon, convex view of brand, product, and incentives, arguing that breakthroughs require focusing on the end state (a trillion-dollar health-ecosystem) and reverse-engineering the steps needed to get there. He explains his three-pronged data vision—omics, longitudinal clinical data, and continuous wearable data—and why combining these enables predictive, personalized interventions. He contrasts this with past attempts like Forward, noting how API-enabled infrastructure now makes a multi-component health stack feasible in a way it wasn’t years ago. The founder shares a compact philosophy on talent, incentives, and brand: hire the best or “spiky” young talent, give them extraordinary autonomy, and let brand beliefs drive customer and investor engagement. He frames entrepreneurship as a set of deliberate, high-ambition questions—from aiming for a hundred-billion-dollar company in a decade to imagining a billion-dollar enterprise in three years—and stresses that action creates information. The dialogue also touches on the role of happiness, PMA (positive mental attitude), and subjective well-being in health outcomes, as well as the ethical and strategic considerations around sleep optimization, preclinical biology, and the potential risks and rewards of ultra-high-speed biotech progress. Finally, Max reflects on his own journey—from a fearless kid trading on the playground to a founder navigating a storm of self-doubt before securing a foothold in Silicon Valley—and on the importance of staying authentic while relentlessly iterating toward a better future.