Chamath Palihapitiya, Jason Calacanis, David Sacks & David Friedberg – The All-In Journey

Four tech investors-turned-podcasters – Chamath Palihapitiya, Jason Calacanis, David Sacks, and David Friedberg – have become known collectively as the “All-In” crew for their popular podcast. Each has a unique origin story and a two-decade track record in Silicon Valley, yet they’ve converged as business partners, friends, and sometimes provocateurs. Below, we dive into their early lives, career milestones, political shifts, mutual business ties, philanthropy, controversies, and character-defining moments.

Chamath Palihapitiya: From Sri Lanka to Silicon Valley “SPAC King”

Chamath Palihapitiya (center), raised in a humble immigrant family, rose to become a billionaire tech investor . Born in Sri Lanka in 1976, Chamath moved to Canada at age 5 when his father, a civil servant, was posted in Ottawa . He grew up on welfare in a “dysfunctional” household and worked through financial hardships to earn a degree in electrical engineering from the University of Waterloo in 1999 . That tenacity shaped his outlook: “Be around high-functioning, high-quality people and just copy the s**t that they do,” he told students, crediting early role models for his drive .

Chamath’s career took off in the early 2000s. After a stint as the youngest VP at AOL, he landed a pivotal role at Facebook in 2007 . There, he led the social network’s user growth team – boosting users from under 50 million to 750 million by the time he left in 2011 . That success made him fabulously wealthy (a “centimillionaire” by his early 30s) and he struck out on his own, founding the venture firm Social Capital in 2011 . By age 32 he was “a billionaire” and even a part-owner of the Golden State Warriors . But despite the riches, Chamath later admitted he felt “an identity crisis” and wasn’t truly happy .

In 2018, Chamath dramatically transformed Social Capital, pivoting from a traditional VC fund to a family-office model investing only his own capital . The shift provoked an “ego-fuelled collapse” – two co-founders and several partners quit amid the changes . Chamath doubled down on a new direction: the burgeoning world of SPACs (special-purpose acquisition companies). His bold bet on blank-check companies earned him the nickname “SPAC King,” after he launched multiple high-profile SPAC mergers – taking Virgin Galactic, SoFi, Opendoor and others public . By 2021 he had raised at least six SPACs, riding the wave of retail investor enthusiasm . At SPAC-mania’s peak, he became a folk hero for amateur investors, championing Reddit traders on CNBC and Twitter and at one point driving Virgin Galactic’s stock up 173% .

Chamath’s political and social views have evolved in unconventional ways. Once a donor to Democratic campaigns (he contributed to Hillary Clinton in 2015) , he grew disillusioned with establishment politics. In early 2021, he even floated a run for California governor during the recall election, tapping into voter frustration with the status quo . Though he ultimately didn’t run, Chamath often voices “radically centrist” or contrarian views on All-In. Notably, he courted controversy in 2022 by declaring “nobody cares” about China’s Uyghur genocide – a blunt remark that ignited public outrage and forced Virgin Galactic (where he was chairman) to distance itself . Palihapitiya later walked back the comment amid the backlash.

Despite an often brash public persona, Chamath has shown a philanthropic streak. He joined Warren Buffett’s Giving Pledge, vowing to donate most of his wealth, and made a record $25 million gift to his alma mater Waterloo to fund a new engineering building . He’s also given to causes like climate change mitigation and pandemic relief – in 2021 he donated his entire $500,000 profit from a GameStop stock trade to COVID-19 small business relief . Those who know Chamath describe him as audacious, outspoken, and fiercely competitive. He peppers business advice with F-bombs and isn’t afraid to call BS – traits honed from a scrappy upbringing. “Without capital, you’re irrelevant,” he’s fond of saying . Love him or loathe him, Chamath’s confidence and candor have made him a magnetic figure in tech – one unafraid to reinvent himself, whether as a VC, a SPAC evangelist, or a podcaster speaking truth (as he sees it) to power.

Jason Calacanis: Brooklyn Hustler Turned Angel Investor

Jason Calacanis made his name in the dot-com era and later struck gold as an early-stage startup investor. Born in Bay Ridge, Brooklyn in 1970 to a Greek-Irish family, Jason grew up with two brothers in New York City . He attended Xaverian High School (’88) and talked his way into Fordham University, where he earned a B.A. in psychology in 1993 . That gift of gab – and a fearless hustle – defined his early career. In the mid-1990s, seeing the nascent New York tech scene, Jason launched Silicon Alley Reporter, a scrappy industry newsletter that he grew into a glossy magazine covering the city’s Internet boom . By his late 20s, Calacanis had become a voice of Silicon Alley, profiling startups and throwing parties for the new tech elite.

When the dot-com bubble burst in 2000, Silicon Alley Reporter folded, but Jason pivoted quickly. In 2003 he co-founded Weblogs, Inc., a network of niche blogs that presaged the rise of modern blogging . Just two years later, in 2005, he scored his first big payday by selling Weblogs, Inc. to AOL for a reported $25+ million . Calacanis joined AOL’s executive ranks (not without drama – he famously feuded with blog rival Nick Denton and later with TechCrunch’s Michael Arrington), then left to pursue new ventures. Ever the serial entrepreneur, he launched a conference series and an email newsletter, and in 2009 started This Week in Startups, a podcast where he interviews founders and tech luminaries.

Jason’s greatest success came as an angel investor. In 2009, his friend Travis Kalanick pitched him a scrappy ridesharing startup – Uber. Calacanis wrote a $25,000 check that would eventually be worth roughly $100 million when Uber went public . That single bet cemented Jason’s status among the top “super-angels.” He went on to early-invest in other unicorns like Robinhood, Wealthfront, and Calm, leveraging his network and media savvy to get into hot deals . By 2017, Forbes estimated his net worth at over $100 million largely from these startup stakes . In 2018 he authored the book Angel, sharing his strategy of spotting “founder mentality” and backing bold entrepreneurs – much like himself.

Politically, Calacanis has tended to lean centrist Democrat with a maverick streak. He supported Democratic candidates like Hillary Clinton and more recently moderate figures (for example, he donated to Rhode Island Democrat Helena Foulkes in 2022) . Yet he’s also a vocal critic of far-left policies and “woke” culture, aligning in spirit with his more conservative All-In co-hosts on issues of crime and business climate. During the 2020 election he castigated President Trump, but also urged Democrats to champion practical economics over ideology. “I’m too conservative for the liberals, and too liberal for the conservatives,” Jason jokes. His independent streak showed during the 2023 Silicon Valley Bank panic: as fears of a bank run spread, Calacanis loudly urged the government to backstop deposits. Some accused him of inciting alarm on Twitter, but he frames it as sounding the alert to save startups .

Within the All-In quartet, Jason is often the brash moderator and hype-man. He brings a Brooklyn bluntness and humor to discussions, readily ribbing his pals and dropping one-liners. Business-wise, he’s deeply intertwined with the others: Chamath and Jason have been poker buddies for years (Chamath was even best man at his wedding), and Jason frequently co-invests with Sacks and Friedberg’s funds. In 2020, the four began recording their candid weekly conversations on Zoom – which organically became the All-In Podcast, now a top business podcast. Calacanis serves as the de facto host, keeping the chats (somewhat) on track and the “Besties” banter flowing.

Despite his tough talk, those close to Jason note his big heart and loyalty. He mentors young founders in his LAUNCH incubator and has quietly donated to charities like Charity:Water . Any profile of Calacanis wouldn’t be complete without mentioning his firecracker personality: he’s competitive, unabashedly self-promotional, and not afraid to butt heads (journalist Kara Swisher once dubbed him “one of the loudest mouths in Silicon Valley”). Yet that same energy has made him a tireless champion of entrepreneurs. “I like winning. You’re here to win. We’re going to win together,” he tells his startup cohorts . Two decades after his first startup, Jason Calacanis still attacks business with the scrappy optimism of an underdog – and that’s exactly how he likes it.

David Sacks: PayPal Mafia Don to Political Firebrand

David Sacks boasts one of tech’s most impressive resumes – PayPal mafia COO, founder of Yammer, and now a leading voice in VC. Born in 1972 to a Jewish family in Cape Town, South Africa, Sacks emigrated with his parents to Tennessee at age five . He grew up in Memphis, then headed west to earn a B.A. in economics at Stanford University (1994) and a J.D. at **University of Chicago Law School (1998) . In a twist of fate, while at Stanford he befriended classmate Peter Thiel – together they penned The Diversity Myth in 1995, a controversial book critiquing political correctness on campus . That early contrarian streak in Sacks’ ideology (the book downplayed date-rape and affirmative action, a stance he later apologized for) hinted at the independent thinker he would become .

David’s career launched with PayPal, where he joined co-founders Thiel, Max Levchin, and Elon Musk in 1999 as one of the first product leaders . Rising to Chief Operating Officer, Sacks was instrumental in building PayPal’s payment product and orchestrating its $1.5 billion sale to eBay in 2002. This made him a multi-millionaire at just 30. Rather than jump into another startup immediately, Sacks took a detour to Hollywood – in 2005 he produced the satirical film Thank You for Smoking, indulging a passion for film (and perhaps for skewering hypocrisy). But the tech world lured him back. In 2007 he founded Geni.com, a genealogy social network, which in turn spawned an idea for enterprise collaboration.

By 2008, Sacks spun out Geni’s communications tool into Yammer, an enterprise social networking platform that became an enterprise hit. As Yammer’s CEO, he grew the business to 5+ million corporate users in four years . In 2012, Microsoft acquired Yammer for $1.2 billion cash, netting Sacks a fortune reported at $100+ million . This triumph cemented his reputation as a savvy founder-CEO. After Yammer, Sacks took on a fixer role in 2016 as interim CEO of Zenefits, steering the HR startup through a compliance scandal . He then co-founded Craft Ventures in 2017, a VC fund where he’s General Partner, backing startups like Airbnb, Facebook, Uber, and SpaceX early (Sacks had quietly been an angel in those companies) . Never one to sit idle, in 2021 he launched Callin, a social podcasting app, showcasing his continued appetite for innovation.

In recent years, Sacks has emerged as the most politically outspoken of the All-In crew. A lifelong libertarian-leaning Democrat, Sacks grew disenchanted with the Democratic party’s leftward shift. He became a vocal critic of COVID lockdowns and what he calls “woke orthodoxy.” By 2022, he was donating and networking in Republican circles – even serving as an advisor and donor to Florida Governor Ron DeSantis. In May 2023, David notably moderated DeSantis’ presidential campaign launch on Twitter Spaces (alongside Elon Musk), where he praised DeSantis’ leadership . Sacks donated $50,000 to DeSantis and also hosted a fundraiser for Democratic-turned-independent candidate RFK Jr., reflecting his heterodox politics . He’s declared himself politically “homeless,” blasting the far left while also arguing the GOP should abandon Trump-style election denial. Sacks has courted controversy for opposing U.S. military aid to Ukraine – arguing the U.S. “provoked” Russia’s invasion and should push for peace talks . Critics have labeled him a Putin apologist, though Sacks insists he’s simply anti-war. Unfazed, he uses All-In and his active Twitter account to champion free speech, crypto, and what he sees as common-sense centrism (critics might say right-libertarian views).

Among the four, Sacks is often seen as the strategist and ideologue. Colleagues describe him as extremely analytical – the one who will reference history or data to win an argument on the pod. His sharp intellect can come off as intensity. Indeed, Sacks isn’t afraid to ruffle feathers: in 2023, when Silicon Valley Bank collapsed, he and Calacanis loudly urged federal intervention, drawing some blame for fanning panic. (Later reports showed their warnings were well-founded, and Sacks quipped that “shooting the messenger” was unfair when thousands of startups were at risk.) Through it all, David Sacks has proven to be principled, if polarizing. After 20+ years in tech, he’s achieved the rare trifecta of successes – PayPal, Yammer, Craft – yet he seems to relish his new role as an independent thinker “calling out” the system. Whether campaigning for tech-friendly political candidates or grilling bureaucrats on All-In, Sacks has evolved from a PayPal mafia consigliere into a self-styled warrior for his vision of the American Dream.

David Friedberg: The Scientist Who Made Climate His Business

David Friedberg is the least flashy of the group – a science prodigy-turned-entrepreneur who made his fortune at the intersection of big data and agriculture. Born in 1980 in South Africa, Friedberg moved with his family to Los Angeles at age 6 . He was a precocious kid, competing in math tournaments and even working at a physics lab in his teens. He attended the elite Harvard-Westlake School (rubbing shoulders with classmates like Paris Hilton and Kim Kardashian) and went on to study astrophysics at UC Berkeley, graduating in 2003 . That scientific mindset has defined Friedberg’s career and worldview.

After college, Friedberg joined Google – still a young company – where he was a product manager on AdWords. But in 2006, while commuting past a bicycle rental shop rained out by bad weather, he had an epiphany: weather data could be used to build better insurance. At just 26, he quit Google to found WeatherBill (later The Climate Corporation). Friedberg spent years building a platform that ingests weather data to help farmers insure their crops against climate fluctuations. His bold idea was vindicated in 2013 when Monsanto acquired The Climate Corp for ~$930 million , one of the largest ag-tech exits ever. Friedberg – who reportedly owned a significant stake – became extraordinarily wealthy overnight, earning an estimated $100+ million from the sale. Rather than face criticism for “selling out” to Monsanto, Friedberg tackled it head-on: he publicly defended the move, arguing that “calling a company evil is easy” but that working from within could drive change . He even wrote an internal letter to employees explaining that partnering with Monsanto would accelerate their mission . (Monsanto integrated Climate Corp’s tech to help farmers globally, though skeptics remained wary of the agri-giant’s motives.)

Post-acquisition, Friedberg stayed on as CEO of Climate Corp and later led Monsanto’s digital agriculture strategy. By 2016, he left to return to startups, founding The Production Board (TPB) – a venture foundry focused on solving big problems in food, agriculture, and life sciences. Through TPB, he has launched and funded companies in areas like alternative protein, crop genomics, and sustainable coffee. Friedberg also co-founded Metromile, a pay-per-mile auto insurer, which went public in 2021. Unlike his All-In friends, Friedberg keeps a relatively low profile. He doesn’t court media or Tweet political hot takes. Instead, he is often “the adult in the room” on the podcast, bringing conversations back to data and first principles. His politics are rooted in pragmatism and science – he focuses on climate policy and technological solutions, and has said he’s less interested in partisan labels than in results. On All-In, Friedberg sometimes expresses frustration at the hyper-political tangents, preferring to dive into topics like CRISPR crops or nuclear energy with wonky enthusiasm.

Though not a household name, Friedberg has quietly engaged in philanthropy and public service. He’s donated to environmental nonprofits and advised Los Angeles on climate resilience. During the COVID-19 pandemic, he helped organize resources for developing lab-grown vaccine components. His character shines through as cerebral but passionate: friends jokingly call him “The Professor” for his tendency to launch into mini-lectures (often accompanied by a knowing grin from Chamath and eye-rolls from Jason). Yet, he’s also known for a sly sense of humor – on the pod he’s fond of geeky puns and even launched a viral meme by jokingly blaming things on “Friedberg’s Mom.” Those who’ve worked with Friedberg describe him as intensely mission-driven. “I only want to work on problems that matter,” he says, reflecting on how selling his company only fueled his desire to tackle existential issues like climate change .

Today, as CEO of The Production Board and the resident “science guy” on All-In, David Friedberg brings a unique perspective melding business and science. He often reminds his colleagues (and listeners) to consider the evidence, whether on climate policy or pandemic data. In a group of big egos, Friedberg is modest and measured – but make no mistake, his achievements speak loudly. He took a boring niche like crop insurance and turned it into a billion-dollar innovation, years before “climate tech” was cool. Now, with his besties by his side, Friedberg is leveraging his expertise and capital to invest in the next generation of world-changing companies. Quietly ambitious and eternally curious, he personifies the idea that entrepreneurship and science together can help save the planet.

Bestie Business: Relationships, Conflicts & Collaboration

It’s no coincidence these four ended up launching a podcast together – their paths have intertwined for years. Chamath and David Sacks knew each other as fellow PayPal Mafia alums and later through venture deals (Chamath’s Social Capital was an early investor in Sacks’ Yammer) . Jason Calacanis met Chamath over a decade ago in poker games and tech conferences; Chamath even invested in Jason’s LAUNCH Fund. Calacanis and Sacks crossed paths during the Weblogs and PayPal days, and later when Jason’s conference TechCrunch50 awarded Yammer top prize in 2008 . David Friedberg, a bit younger, was introduced to the circle via mutual friends in Silicon Valley – his reputation as a “quant” entrepreneur earned Chamath’s respect (Social Capital was a minority investor in Climate Corp before the Monsanto sale). By the late 2010s, they found themselves chatting regularly about tech, markets, and politics.

What began as a private WhatsApp group and weekly Zoom hangout for these “Besties” morphed into the All-In Podcast in early 2020. The timing was perfect: COVID lockdowns had everyone craving insight (and entertainment) about the chaotic world. Their candid, no-BS style – four successful guys cracking jokes one minute and debating policy the next – struck a chord. Despite their occasional conflicts (indeed, part of the appeal is listening to them argue), they share deep mutual respect. For example, when Chamath’s Uyghur comments sparked outrage, Jason and David Sacks gently pushed back on-air, and Chamath later acknowledged he worded it poorly. Sacks and Calacanis have butted heads over how hard to go on Trump or on teachers’ unions, but they navigate differences with humor (and sometimes spirited shouting). Friedberg, when fed up with the bickering, will pointedly threaten to “leave the show” – prompting the others to recalibrate. It’s a dynamic friendship, with a healthy mix of rivalry and brotherhood.

They’ve also become business partners in various capacities. All four are investors in each other’s funds or companies – for instance, Sacks and Chamath are LPs in Calacanis’s angel funds, and Chamath and Jason co-invest with Sacks’ Craft Ventures on deals. In 2022, they even launched the All-In Summit, a business conference that sold out in minutes, showing the brand power of their collaboration . Yet they are careful to (try to) disclose any financial interests when discussing companies on the pod, to avoid ethical issues. Still, critics have noted the potential for conflicts of interest – for example, when they hype crypto or stocks that they might own. In response, the Besties insist they’re “transparent and doing it for the love of the game,” not pump-and-dump. They’ve each made fortunes already, and All-In (which carries no ads) seems more passion project than profit center.

The philanthropic and ethical dimension of their relationship also bears mention. All four joined forces in 2020 to donate over $1 million combined to pandemic relief in California. They’ve used their platform to raise money for Ukrainian refugees and climate causes (Friedberg led an “All-In Challenge” for carbon removal projects). However, they’ve also faced scrutiny – notably, some accused Calacanis and Sacks of sparking the Silicon Valley Bank run in 2023 by urging founders to withdraw funds, which they vehemently deny as “shooting the messenger.” Each brings a different moral compass: Chamath, the effective altruist who believes in “doing well by doing good”; Jason, the open book who wears his heart on his sleeve (and sometimes foot-in-mouth on Twitter); Sacks, the ideologue guided by free speech and meritocracy; and Friedberg, the utilitarian focused on outcomes over rhetoric.

Inside Jokes and Character Insights

Spend a few hours listening to the All-In Podcast, and you’ll pick up on the inside jokes and personality quirks that define each Bestie. Chamath is often called the “SPAC King,” but the others tease him as the “Jabroni” (a wrestling term for loser) whenever one of his SPAC deals flops. He takes it in stride – his swagger and willingness to say “I don’t know” in equal measure make him a paradoxical leader. Jason is the “adult supervision” only until he isn’t – he’ll passionately rant about a startup he loves or a politician he hates, showcasing his infectious enthusiasm and occasional temper. Sacks is dubbed “The Rainman” for his rapid-fire recall of facts and figures during debates; his friends also affectionately call him “Cole” (a reference to a character in Yellowstone) when he goes on a pro-market, tough-love tirade. His intensity is balanced by dry wit – Sacks will drop a deadpan joke after a heated monologue, cracking everyone up. And Friedberg, often quiet for long stretches, will suddenly unleash a “Science Corner” monologue about food scarcity or battery technology, earning mock groans but genuine admiration for his brainpower and sincerity.

In private, the four are said to have a deep camaraderie. They vacation together with their families, exchange parenting advice (Calacanis has young children; Sacks and Friedberg are also dads), and even have a shared “Besties” group chat that’s as much memes as it is market analysis. “It’s like a band,” Jason says. “Sometimes we play different tunes, but when we’re in sync, it’s magic.” All-In’s runaway success – millions of downloads, a dedicated fanbase of “All-Inners”, and even notable guests like Elon Musk – underscores how their combined voices are more powerful than alone. Individually, each has led companies and made headlines; together, they’re shaping conversations in tech, finance, and politics in a way few traditional media figures can.

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