Fact-checked by Grok 2 weeks ago

Jason Calacanis

Jason McCabe Calacanis (born November 28, 1970) is an American internet entrepreneur, angel investor, podcaster, and author recognized for his early-stage technology investments and promotion of startup ecosystems.^[1]^[2] Calacanis co-founded Weblogs, Inc. in 2003 with Brian Alvey, building a network of specialized blogs that was acquired by AOL in 2005 for between $20 million and $35 million, marking one of the early successes in digital media aggregation during the Web 2.0 era.^[3] Following this, he transitioned to angel investing, committing early capital to Uber—reportedly as one of its first outside investors with a $25,000 stake that yielded over $100 million upon liquidity events—along with Robinhood, Calm, and Thumbtack, contributing to his reputation as a high-return seed investor in over 300 startups.^[2]^[4]^[5] In 2009, Calacanis launched the "This Week in Startups" podcast, which has grown into a leading platform interviewing founders and analyzing tech trends, while also founding the LAUNCH accelerator and annual festival to connect emerging entrepreneurs with investors, particularly fostering the Los Angeles venture scene.^[6]^[7] His candid, often contrarian public commentary—evident in co-hosting the All-In Podcast and advisory roles like during Twitter's 2022 transition under Elon Musk—has amplified his influence but also sparked disputes with figures in tech and media.^[8]^[9]

Early Life and Education

Childhood and Family Background

Jason Calacanis was born in the Bay Ridge neighborhood of Brooklyn, New York, to parents of Greek and Irish descent, with his father being Greek.^[10] ^[11] ^[12] He has two brothers and grew up in a blue-collar household during the 1970s and 1980s.^[11] ^[12] ^[13] His father worked as a bartender and managed a bar-restaurant, while his mother served as a nurse and held multiple jobs to support the family.^[14] ^[15] ^[13] Calacanis has described his parents as hardworking, with the family's circumstances shaping his early experiences, including time spent around his father's establishment.^[15] ^[13] By age 17, the family faced severe financial hardship when his father lost his business and risked imprisonment for tax evasion, an event Calacanis later cited as formative to his drive for financial independence.^[16]

Formal Education and Early Influences

Calacanis attended Fordham College at Lincoln Center, part of Fordham University, where he earned a Bachelor of Arts in psychology in 1993.^[17]^[18] Despite graduating high school with an average around 70, he gained admission through persistent outreach to an admissions officer, supplemented by reference letters and improved senior-year grades.^[17]^[14] His college experience spanned five years, marked by academic struggles and financial necessity, as he enrolled full-time in evening classes while holding multiple low-wage jobs, including barback, waiter, computer lab technician, and laser printer repair.^[17]^[19]^[14] Family financial setbacks exacerbated these challenges; his father's bar business failure around age 16 led to asset seizures, including tuition funds, forcing Calacanis to self-fund through relentless work.^[14] Early influences stemmed from his Brooklyn working-class upbringing, with a bartender father and nurse mother instilling a strong work ethic amid economic instability.^[17]^[19] The paternal business collapse motivated a personal vow against failure, reinforced by encounters like an elevator meeting with Sony executive Tommy Mottola, which highlighted the allure of influence and power.^[14] Additionally, a taekwondo instructor—a Fordham alumnus—exemplified persistence, aiding his admissions pursuit and shaping his approach to overcoming barriers.^[17] These experiences fostered an early gravitation toward media and journalism, viewing editorial control as a pathway to impact.^[19]

Early Entrepreneurial Career

Founding Silicon Alley Reporter

In 1996, Jason Calacanis founded the Silicon Alley Reporter (SAR), a print newsletter focused on New York's burgeoning internet and technology ecosystem, dubbed "Silicon Alley" for its concentration of startups in Manhattan.^[17]^[20] The publication emerged amid the dot-com boom, providing coverage of local entrepreneurs, funding rounds, and industry events to an initial audience of tech insiders and investors.^[21] SAR began as a modest 16-page newsletter, initially produced through low-cost methods like photocopying, and quickly gained traction by filling a gap in media attention for East Coast tech developments, which were overshadowed by Silicon Valley narratives.^[17] By 1996–1997, circulation reached approximately 10,000 subscribers, reflecting early demand for its directory-style listings of startups, personnel moves, and venture activity.^[20] Calacanis, then in his mid-20s, self-funded and edited the venture under his newly established Rising Tide Studios, leveraging his network from prior sales roles to distribute issues at events and via mail.^[21]^[17] The newsletter's format emphasized practical utility, including company profiles, job listings, and deal trackers, which positioned it as an essential resource for the Silicon Alley community before online directories proliferated.^[20] Its growth from a niche periodical to a fuller magazine by the late 1990s—expanding to hundreds of pages—underscored Calacanis's hands-on approach to content aggregation and event tie-ins, such as co-organizing the Silicon Alley Reporter Awards to boost visibility.^[17] This foundational effort established Calacanis as a key chronicler of New York's tech ascent, predating his expansions into digital media.^[21]

Rising Tide Studios and Weblogs, Inc.

In the mid-1990s, Calacanis founded Rising Tide Studios, a media company focused on publishing print and online magazines covering the technology and internet sectors in New York City's "Silicon Alley."^[22] The company produced titles such as the Silicon Alley Reporter, which chronicled the local tech startup ecosystem during the dot-com boom, and the Digital Coast Reporter.^[22] Rising Tide also organized conferences and events, gaining a reputation for hosting extravagant parties that attracted tech industry figures.^[23] However, the company faced financial difficulties amid the dot-com bust and filed for bankruptcy, after which its assets were acquired by a private equity firm.^[24] Following the sale of Rising Tide Studios, Calacanis co-founded Weblogs, Inc. with Brian Alvey on September 24, 2003, securing initial angel investment from Mark Cuban.^[24] The venture operated as an early blog network, producing advertising-supported content across specialized sites on topics including technology, automotive, and entertainment, with a focus on timely, expert-driven posts rather than traditional journalism.^[25] Under Calacanis's leadership as CEO, Weblogs, Inc. grew rapidly by recruiting prominent bloggers and emphasizing niche verticals, achieving profitability through targeted ads and sponsorships.^[25] In November 2005, AOL acquired the company for approximately $25 million in cash, marking a significant exit for Calacanis and enabling him to retain some editorial oversight post-acquisition.^[26]^[27] This sale provided capital that Calacanis later directed toward angel investing, though reports vary slightly on the exact figure, with some estimating up to $30 million.^[28]

Sale to AOL and Aftermath

In October 2005, AOL acquired Weblogs, Inc., the blog network founded by Jason Calacanis and Brian Alvey in 2003, for a reported $25 million in cash.^[29] ^[30] The transaction, announced on October 6, included popular sites like Engadget, which had grown to generate significant traffic and ad revenue under Calacanis's leadership, with the network employing around 500 bloggers by the time of the sale.^[3] ^[14] Some reports estimated the total value, including potential earnouts, at $20–35 million, reflecting AOL's strategy to integrate independent digital content creators amid declining traditional media dominance.^[3] ^[31] Post-acquisition, Calacanis joined AOL as general manager of Weblogs, Inc., overseeing operations and contributing to content strategy for roughly one year.^[32] During this period, the blogs maintained editorial independence but benefited from AOL's distribution resources, though integration challenges arose due to corporate bureaucracy and differing priorities between the agile startup culture of Weblogs and AOL's established structure.^[32] Calacanis later described the experience as a learning opportunity in scaling media operations, but cited frustrations with large-company dynamics as a factor in his decision to depart in 2006.^[14] Following his exit from AOL, Calacanis redirected proceeds from the sale toward new ventures, founding Mahalo in 2007 as a human-curated search engine aimed at delivering high-quality results through paid expert editors rather than algorithmic aggregation.^[32] Mahalo raised initial funding from investors including Sequoia Capital but struggled to compete with Google, eventually pivoting toward local search before winding down operations around 2014.^[32] This phase marked Calacanis's shift from media entrepreneurship to exploring technology product development and early-stage investing, leveraging insights from Weblogs' rapid growth and exit to inform risk assessment in nascent internet models.^[28]

Angel Investing and Venture Activities

Development of Investment Approach

Calacanis initiated his angel investing activities following the 2005 sale of Weblogs, Inc. to AOL for approximately $25 million, utilizing a portion of the proceeds to make early personal investments in technology startups.^[26] Initially cautious, he adhered to a principle of self-investment, which led to missed opportunities in companies like Twitter and Zynga, prompting a shift toward broader participation in seed-stage deals around 2006–2009.^[33] This period marked the foundational trial-and-error phase, where he deployed modest sums—starting with about $700,000 across initial investments—emphasizing small, diversified bets akin to poker stakes to mitigate risk while seeking asymmetric returns.^[34] By 2009, frustrations with opaque and fee-charging angel networks drove Calacanis to co-found the Open Angel Forum, an event series designed to democratize access to deal flow by connecting founders directly with investors without upfront costs, thereby refining his sourcing process through structured, high-volume pitch evaluations.^[35] Early successes, such as a $25,000 investment in Uber in 2010, validated a founder-centric thesis: prioritizing exceptional teams pursuing audacious, market-disrupting ideas over polished business plans, informed by his observations that outlandish visions often correlate with outsized outcomes.^[36] This empirical feedback loop—tracking hits like Thumbtack and Robinhood among his first 50 investments, which yielded three unicorns—shaped a philosophy of high deal throughput (eventually 100+ annually) coupled with intensive post-investment support, as he posited that returns scale with time allocated to founders.^[37] The approach further evolved through advisory roles, including scouting for Sequoia Capital, which honed his due diligence on traction metrics and competitive moats, and the 2011 launch of LAUNCH, an accelerator emphasizing rapid iteration and founder coaching to accelerate portfolio company growth.^[38] By 2013, integration with AngelList's syndicate model allowed him to lead group investments, amplifying capital efficiency while maintaining control over selection criteria like founder grit and product-market fit signals.^[39] These mechanisms codified lessons from power-law distributions, where a few winners (e.g., Uber's return exceeding 1,000x) offset numerous failures, prioritizing probabilistic edge over deterministic predictions.^[40] Calacanis later distilled this framework in his 2017 book Angel: How to Invest in Technology Startups, attributing its timeless elements to iterative refinement from direct market exposure rather than theoretical models.^[41]

Notable Investments and Returns

Calacanis invested $25,000 in Uber during its seed stage in 2010, when the company was valued at approximately $5 million. This stake reportedly generated returns of over $100 million by 2017, equating to a more than 4,000-fold multiple on his initial outlay, driven by Uber's subsequent growth, IPO in 2019, and market performance.^[42] ^[34] Among his other notable early-stage investments are Robinhood, where he participated as an angel prior to its 2021 IPO, and Thumbtack, a services marketplace that reached unicorn status.^[7] Calacanis also backed Calm, a meditation app that attained unicorn valuation in 2019, and Wealthfront, a robo-advisor platform.^[7] Additional successes include DataStax, a database software firm; Desktop Metal, a 3D printing company that went public via SPAC in 2021; and Density, a workplace analytics provider.^[7] These eight portfolio companies have collectively achieved valuations exceeding $1 billion each.^[7] Through his personal angel activities and the LAUNCH syndicate, Calacanis has deployed capital into over 300 startups, typically in check sizes of $25,000 to $50,000 per deal.^[34] His initial $700,000 in aggregate angel investments across early deals expanded to a portfolio valued at approximately $100 million, underscoring the power-law dynamics where outlier returns like Uber dominate overall gains.^[34]

Syndicate Model and LAUNCH Accelerator

Jason Calacanis established The Syndicate, an angel investing platform at TheSyndicate.com, which operates as a lead investor model pooling capital from over 10,000 accredited investors to back early-stage startups.^[43]^[44] In this syndicate structure, Calacanis identifies promising founders, conducts due diligence, negotiates terms, and structures deals via special purpose vehicles (SPVs), enabling limited partners to co-invest with reduced individual effort.^[45]^[46] The model incorporates platform fees and carried interest—typically 20% on profits after returning capital—allowing Calacanis to amplify his investment volume beyond personal funds, with the syndicate having participated in numerous deals since its inception.^[45]^[47] Complementing the syndicate, Calacanis founded LAUNCH, a startup support initiative that includes an accelerator program designed to accelerate company growth through structured mentorship and capital.^[7] The LAUNCH Accelerator runs as a 14-week bootcamp emphasizing product development, customer acquisition, fundraising strategies, and pitch refinement, with Calacanis providing direct feedback to participants.^[48]^[49] Selected startups receive $100,000 in funding for 6% equity, and the program has accepted multiple cohorts, including Cohort 35 in 2025.^[48]^[50] Through LAUNCH, Calacanis commits to investing in approximately 100 new startups annually, often integrating syndicate opportunities for broader investor participation post-acceleration.^[51]^[52] Additionally, LAUNCH offers Founder University, a 10-week pre-accelerator providing up to $125,000 to top performers, further expanding its talent pipeline.^[53] This dual approach via syndicate and accelerator has facilitated Calacanis's involvement in over 300 startup investments, leveraging network effects for deal flow and value-add services.^[43]^[54]

Risk, Failures, and Empirical Lessons

Calacanis's angel investing strategy embraces high-risk, early-stage opportunities, where the majority of investments result in total loss or minimal returns, reflecting the empirical reality of startup failure rates estimated at 70-90%.^[33]^[55] He has stated that approximately seven out of ten deals fail outright, necessitating a portfolio approach with small individual bets—typically 1-2% of capital per startup—to preserve liquidity and enable high-volume investing, often 100 deals annually via his syndicate.^[56]^[57] This mitigates the asymmetric risk profile, where outliers like his $25,000 Uber investment yielding over $100 million by 2017 compensate for widespread losses, but demands tolerance for illiquidity, dilution, and zero exits.^[58] Notable failures in his portfolio underscore these risks; for instance, his backing of Circa News, a mobile-first outlet aimed at non-sensationalized reporting, collapsed by 2019 amid challenges in monetizing quality journalism without clickbait.^[59] Similarly, ventures like Inside.com, which Calacanis championed as a curated news app launched in 2015, failed to achieve user scale and pivoted to email newsletters by February 2016 due to inadequate product-market fit.^[60] These outcomes align with broader patterns where even experienced investors face execution pitfalls, as Calacanis has noted in critiquing corporate VC overreach and founder missteps in resource allocation.^[61] Key empirical lessons from Calacanis's experience emphasize causal factors beyond funding shortages: founder judgment errors, such as poor hiring or pivots, drive most failures, not capital exhaustion.^[62] He advocates selecting resilient founders who treat setbacks as iterative learning, akin to poker players folding weak hands while stacking deep for rare strong ones, and stresses post-investment involvement to influence outcomes without micromanaging.^[37] Syndication further distributes risk, enabling collective due diligence and follow-on capital, while tax strategies like loss harvesting offset failures against gains.^[63] Ultimately, success hinges on volume and patience, as power-law returns from survivors eclipse aggregated losses only for those enduring the psychological toll of repeated zeros.^[64]

Podcasting and Media Ventures

This Week in Startups

This Week in Startups (TWiST) is a podcast hosted by Jason Calacanis, launched on May 2, 2009, that examines developments in startups, technology, markets, media, and business. The show originated amid Calacanis's transition from web entrepreneurship to media and investing, initially airing as part of broader podcasting efforts following his involvement with the TWiT.tv network, from which he departed amid disputes over content control and syndication. Early episodes featured Calacanis solo or with co-hosts like Molly Wood, emphasizing unfiltered commentary on tech news and founder interviews, with a format centered on weekly recaps and listener questions. By 2025, it had surpassed 2,000 episodes, reflecting sustained production over 16 years.^[65]^[66] The podcast's format has evolved from informal, live-streamed discussions to a structured mix of news breakdowns via the "TWiST Ticker" segment, deep-dive interviews with founders, and analysis of investment trends, often incorporating Calacanis's angel investing experiences. Current co-hosts include Alex Wilhelm for market insights and Lon Harris for media perspectives, enabling multifaceted coverage; episodes typically run 45-90 minutes and are distributed across platforms like YouTube, Apple Podcasts, and Spotify. Key themes encompass startup scaling challenges, venture capital dynamics, AI advancements, regulatory impacts on tech, and economic policy effects on innovation, with recurring emphasis on empirical success factors like founder grit and market timing over hype-driven narratives. Notable guests have included executives from Uber, Robinhood, and emerging AI firms, providing firsthand accounts of pivots, funding rounds, and competitive landscapes—such as early discussions on ride-sharing disruptions and crypto volatility.^[67]^[66]^[68] Reception among tech enthusiasts and entrepreneurs has been favorable, evidenced by a 4.2 out of 5 rating on Apple Podcasts from 1,266 reviews as of October 2025, with listeners citing its practical advice on deal sourcing and failure avoidance as influential for launching ventures. The podcast's impact extends to Calacanis's LAUNCH accelerator, where episodes often preview events or scout talent, fostering a network that has backed over 250 startups; it has shaped discourse on contrarian investing, such as skepticism toward overvalued unicorns during market corrections. Criticisms, primarily directed at Calacanis's host style, include accusations of self-promotion and provocative takes on topics like angel group inefficiencies or H-1B visa debates, which some view as alienating but others praise for challenging consensus views in investor circles—though no major scandals have derailed its run, unlike contemporaneous shows facing advertiser pullouts. Sources close to early podcasting note tensions with figures like Leo Laporte over independence, underscoring Calacanis's preference for owner-operated media to avoid editorial biases.^[68]^[69]

Origins and Format Evolution

This Week in Startups originated from Jason Calacanis's earlier podcasting efforts with Calacanis Cast, which produced around 30 episodes over two years before being rebranded and relaunched as This Week in Startups (TWiSt) on May 2, 2009.^[13]^[65]^[70] The show initially served as the weekly flagship within Calacanis's ThisWeekIn network, a video-based platform offering daily tech news recaps, distinguishing TWiSt through its targeted focus on startup funding rounds, founder stories, and venture capital trends rather than broad tech updates.^[6] After the ThisWeekIn network ceased operations in 2012 amid financial difficulties, TWiSt evolved into a standalone audio podcast, retaining its interview-driven structure while emphasizing Calacanis's solo commentary on market news and guest discussions with entrepreneurs.^[13] Over subsequent years, the format incorporated recurring co-hosts, including Alex Wilhelm for market analysis and Lon Harris for media insights, alongside segments like the TWiST Ticker for concise breakdowns of weekly startup announcements and investment data.^[67]^[6] These adaptations supported longer episodes averaging 60-90 minutes, blending structured interviews with unscripted debates to align with growing listener demand for actionable business intelligence.^[66]

Key Content Themes and Guests

The podcast emphasizes practical aspects of building and scaling startups, including fundraising techniques, such as the "five levels of founder fundability" framework for attracting venture capital.^[71] Discussions frequently cover market analysis, with episodes dissecting venture capital trends, AI investment opportunities, and startup momentum amid economic shifts.^[72] Other recurring themes include technological disruptions like cryptocurrency ICOs, Bitcoin's role in competition with established firms, and operational strategies such as balancing product vision with customer feedback.^[73] Calacanis often integrates real-time advice on topics like job opportunities in tech, privacy in financial systems, and frameworks for identifying market winners in emerging sectors.^[74]^[75] Episodes blend solo commentary, live Q&A sessions, and news roundtables to address current events, such as regulatory challenges for innovations like Starlink or debates over AI's geopolitical implications.^[76] Notable guests span founders, investors, and tech veterans, providing insights into high-profile ventures. Tech co-founders Shervin Pishevar and Brogan BamBrogan discussed Hyperloop development, highlighting engineering and funding hurdles in transportation startups.^[77] Apple co-founder Steve Wozniak and former Apple CEO John Sculley appeared to share perspectives on innovation and early computing history.^[78] Investor Anthony Pompliano joined for analyses of crypto fundraising and Bitcoin's competitive edge against incumbents.^[73] Venture capitalist Jeff Richards of GGV Capital offered views on global investment landscapes, while actor-turned-entrepreneur Adrian Grenier covered launching impact-focused funds and founder education platforms.^[79] Roundtable participants like Dave Mathews of NewAer and Austin Smith of Inside.com tackled gadget innovations and platform dynamics, including reactions to Elon Musk's investor communications.^[80] These appearances underscore the podcast's focus on actionable lessons from established figures in tech and business.

Reception, Impact, and Criticisms

The podcast has received generally positive reception within the startup and technology communities, praised for its timely coverage of industry news, founder interviews, and practical insights into entrepreneurship. On Apple Podcasts, it holds a 4.2 out of 5 rating based on over 1,266 reviews, with listeners appreciating its role in staying informed on market trends and success stories.^[68] Similarly, Podchaser rates it 4.8 out of 5 from a smaller set of reviews, highlighting its value in dissecting tech and business topics.^[81] Rephonic aggregates a 4.3 rating from nearly 3,000 reviews, reflecting broad appeal among tech enthusiasts.^[82] Its impact extends to shaping discussions in the venture capital and startup ecosystems, with over 1,300 episodes since its 2009 launch fostering education on funding, scaling, and market dynamics through high-profile guests like founders and investors.^[81] The show has been featured in lists of top business podcasts for 2025, underscoring its role in democratizing access to insider perspectives and influencing emerging entrepreneurs.^[83] By integrating Calacanis's angel investing expertise, it has amplified awareness of syndicate models and early-stage opportunities, contributing to broader participation in startup investing.^[84] Criticisms primarily center on production elements and host dynamics, including complaints about excessive embedded advertisements that disrupt flow, as noted in user reviews describing it as turning occasional listens into avoidable ones despite strong content.^[85] The departure of co-host Molly Wood in 2023 drew backlash from some listeners who perceived shifts in tone and cohesion, with forums reporting negative feedback on the podcast's evolving format.^[86] Additionally, Calacanis's promotional style and occasional public disputes, such as his 2019 criticism of marketing figures on social media, have led subsets of the audience to disengage, viewing episodes as overly self-serving.^[87] No major ethical or legal controversies directly tied to the podcast's operations have surfaced in public records.

All-In Podcast

Launch and Co-Host Dynamics

The All-In Podcast premiered on March 19, 2020, amid the early stages of the COVID-19 pandemic, with its inaugural episode focusing on market disruptions and remote work trends. Hosted by four Silicon Valley figures—Chamath Palihapitiya (venture capitalist and former Facebook executive), Jason Calacanis (angel investor and podcaster), David Sacks (PayPal and Yammer co-founder), and David Friedberg (former Google executive and climate tech investor)—the show positions itself as a platform for unvarnished discussions among "besties" with complementary expertise in tech, finance, and policy. Calacanis, who also executive produces, has recounted the podcast's origins in informal group chats that evolved into a structured format to counter perceived media biases during economic uncertainty. The co-hosts' dynamics emphasize camaraderie and debate, with Palihapitiya often taking contrarian economic stances, Sacks focusing on policy and free speech, Friedberg on science and data, and Calacanis injecting entrepreneurial anecdotes; however, tensions have surfaced, such as public disagreements over episode moderation where one co-host criticized another's approach as unbalanced.^[88]^[89]^[90]^[91]^[92]

Discussion Topics and Influence

Episodes typically dissect current events in economics (e.g., federal debt trajectories and GDP forecasts), technology (e.g., AI infrastructure investments and data center expansions), politics (e.g., regulatory overreach and election impacts), social issues, and occasionally poker strategy, blending data-driven analysis with personal insights from the hosts' professional histories. The format encourages long-form, Econts (besties) to challenge mainstream narratives, fostering a contrarian lens on topics like venture funding cycles and innovation policy. This approach has elevated the podcast's reach, amassing millions of downloads and positioning it as a key venue for Silicon Valley discourse, with Calacanis leveraging it to broaden his profile beyond investing into cultural and political commentary, influencing investor sentiment and startup strategies through candid breakdowns of market signals.^[93]^[90]^[94]^[95]

Controversies and Audience Backlash

The podcast has encountered criticism for its perceived shift toward politically conservative viewpoints, particularly after episodes engaging with figures like Donald Trump in June 2024, which drew accusations from some listeners of devolving into partisan advocacy rather than balanced debate. Interpersonal frictions among hosts, including a 2023 Twitter exchange between Calacanis and Sacks over content moderation, highlighted internal divisions on handling sensitive topics. Outlets like Slate have portrayed it as an "infuriating safe space" for Silicon Valley's elite to voice unfiltered opinions often at odds with mainstream media consensus, amplifying backlash from progressive audiences who view the discussions as insufficiently critical of right-leaning policies. Despite this, the show's influence persists, with defenders arguing it fills a gap for empirical, insider critiques amid institutional biases in traditional reporting; Calacanis's aggressive interviewing style has separately fueled detractors claiming it prioritizes spectacle over substance.^[96]^[97]^[92]^[98]

Launch and Co-Host Dynamics

The All-In Podcast launched its first episode on March 19, 2020, amid the early stages of the COVID-19 pandemic, with Jason Calacanis serving as co-host alongside Chamath Palihapitiya, David Sacks, and David Friedberg.^[88] The initiative stemmed from the co-hosts' established routine of playing poker together, which was disrupted by pandemic-related lockdowns and social distancing measures, leading them to adapt their informal gatherings into structured online conversations on business, technology, and current events.^[89] This origin as a "poker game replacement" fostered a casual yet incisive dynamic, characterized by the hosts' self-description as "degenerate gamblers & besties," emphasizing their pre-existing personal rapport and shared risk-taking mindset in investing.^[90] The co-hosts' interactions reflect complementary professional backgrounds and temperaments that enable robust, often contentious discourse without descending into unproductive conflict. Calacanis, an experienced podcaster and angel investor with early stakes in companies like Uber, frequently drives startup-focused segments and moderates with his media savvy.^[99] Palihapitiya, founder of Social Capital and a proponent of SPACs and mission-driven investing, injects macroeconomic analysis and contrarian takes on policy. Sacks, a PayPal Mafia member who founded Yammer and Craft Ventures, contributes geopolitical and regulatory insights shaped by his enterprise software experience. Friedberg, through The Production Board and prior roles at Google X, anchors discussions in empirical science, biotechnology, and climate innovation. Their dynamics feature playful ribbing—such as Calacanis's energetic interruptions balanced by Sacks's measured rebuttals—and a consensus-driven approach to disagreements, rooted in mutual respect from years of overlapping Silicon Valley networks, though occasionally strained by diverging political leanings.^[92] ^[100] This setup has sustained listener engagement by blending insider expertise with authentic interpersonal friction, as evidenced by the podcast's rapid growth to millions of downloads per episode within its first year.^[101]

Discussion Topics and Influence

The All-In Podcast episodes typically explore intersections of macroeconomics, technological innovation, and geopolitical shifts, with recurring emphasis on U.S. fiscal policy, including federal debt trajectories, inflation dynamics, and Federal Reserve interventions.^[102] Calacanis contributes perspectives grounded in venture capital trends, such as AI-driven disruptions in education and data center investments, often highlighting opportunities for startups amid broader economic pressures like GDP stagnation and dollar devaluation.^[102] Discussions on tech policy frequently critique regulatory overreach, covering topics like antitrust actions against Google and the competitive implications of AI copyright frameworks.^[102] Political commentary forms a core thread, addressing issues such as tariffs' legal challenges, White House engagements with tech leaders, and U.S. energy infrastructure's role in sustaining AI growth.^[103] Calacanis has weighed in on cultural phenomena, including gambling scandals and Ivy League institutional responses to antisemitism, drawing analogies from high-stakes poker to expose systemic vulnerabilities.^[104] Social topics extend to consumer economy indicators and global competitiveness, where hosts, including Calacanis, advocate for market-oriented reforms over interventionist approaches.^[105] The podcast's influence manifests in its amplification of contrarian viewpoints within Silicon Valley and investor circles, fostering debates that challenge mainstream narratives on regulation and innovation.^[92] With millions of downloads and high-profile episodes garnering hundreds of thousands of views, it has elevated Calacanis's profile, enabling direct dialogues with policymakers like Senator Joe Manchin on economic strategy.^[106] ^[103] This reach has shaped venture capital discourse, promoting empirical scrutiny of policy impacts on entrepreneurship, though critics argue it risks entrenching elite biases favoring deregulation.^[107]

Controversies and Audience Backlash

The All-In Podcast has encountered criticism for its handling of politically charged episodes, particularly the June 20, 2024, interview with Donald Trump, where hosts including Jason Calacanis were faulted by some observers for insufficiently challenging the former president's statements on topics like artificial intelligence and economic policy.^[108]^[109] This episode drew accusations of softball questioning, contributing to broader claims that the podcast had shifted from balanced tech analysis to a platform sympathetic to conservative viewpoints, though such critiques often emanate from outlets with documented left-leaning editorial slants.^[109] Calacanis, in particular, has faced intra-group and listener pushback for his conversational style, including frequent interruptions that co-host David Sacks highlighted during episodes discussing political campaigns, prompting debates over decorum and airtime equity.^[92] Listener feedback on platforms like podcast review aggregators reflects growing discontent among a subset of the audience, with complaints centering on perceived declines in substantive discourse amid rising political commentary, leading some long-time followers to disengage.^[110] This backlash intensified post-2024 election cycle discussions, where the hosts' explorations of topics like election integrity and policy critiques alienated portions of the original Silicon Valley-centric listenership accustomed to apolitical venture insights, though the podcast retained strong overall engagement metrics.^[111] Critics from tech commentary circles have labeled the evolution as hypocritical given the hosts' prior emphases on contrarianism, yet empirical listenership data suggests the controversy has not materially eroded the show's core appeal among investors and entrepreneurs seeking unfiltered takes.^[94]

Political Views and Public Commentary

Positions on Economic Policy

Calacanis has consistently advocated for fiscal restraint, emphasizing that excessive government spending beyond tax revenues creates unsustainable debt cycles, as evidenced by his commentary on the United Kingdom's economic challenges where policies discourage investment and employment.^[112] He argues for a significant reduction in the rate of government spending growth, aligning with discussions on his All-In Podcast calling for deep cuts, such as trimming personnel costs across departments to address ballooning budgets.^[113]^[114] On taxation, Calacanis supports lower tax rates to stimulate economic activity, viewing policies like border security paired with tax reductions as broadly popular among Americans.^[115] He has critiqued proposals to increase taxes on high earners, such as adding levies on asset sales, as counterproductive and dismissive of wealth creators' contributions.^[116] In debates on capitalism, he highlights how the U.S. federal government's taxation at around 17% of GDP limits efficient service provision, favoring market-driven solutions over expanded public sector roles.^[117] Regarding inflation and monetary policy, Calacanis has expressed support for the Federal Reserve's efforts to combat persistent inflation through rate adjustments, noting its commitment despite economic headwinds.^[118] He has questioned the timing of rate cuts, suggesting potential political influences over data-driven decisions, and participated in discussions questioning the Fed's independence amid pressures from political figures.^[119]^[120] Calacanis warns of broader economic risks from unchecked debt accumulation, predicting crises if governments continue over-leveraging without reforms.^[121] Calacanis prioritizes real wage growth as essential to restoring the American Dream, attributing stagnation to high debt burdens, unaffordable housing, and insufficient productivity gains amid regulatory hurdles.^[122] While generally skeptical of subsidies and grants, he has endorsed targeted interventions like the Intel CHIPS Act deal under certain administrations, arguing they yield taxpayer value through strategic investments in critical industries rather than blanket spending.^[123]^[124] His positions reflect a preference for policies fostering private-sector innovation over expansive government roles, often critiquing large-scale bills as leadership failures that exacerbate fiscal imbalances.^[125]

Stances on Technology and Regulation

Calacanis has consistently advocated for regulatory frameworks that balance innovation with risk mitigation, particularly in emerging technologies like artificial intelligence. In discussions on the All-In Podcast, he has argued that the rapid advancement of AI necessitates proactive regulation to address potential harms, such as misuse in influencing elections, citing the Cambridge Analytica scandal as a cautionary example of unchecked data practices.^[126] He contends that while outright bans or overly prescriptive rules could stifle progress, guardrails on safety and ethical deployment are essential, especially as AI integrates into critical sectors like autonomous driving and content moderation.^[127] This stance reflects a pragmatic view that regulation, if implemented thoughtfully, can prevent catastrophic failures without impeding the productivity gains AI promises, such as doubling worker output every two years in industries like logistics.^[128] On broader technology regulation, Calacanis has criticized heavy-handed approaches that disadvantage competitive regions. In July 2024, he highlighted the European Union's AI regulatory efforts as potentially self-marginalizing, warning that stringent rules could exclude EU firms from global AI development conversations dominated by less-regulated markets like the United States.^[129] He promotes "regulation-proofing" strategies for startups, advising entrepreneurs to design business models—such as empowering independent contractors via LLCs in the gig economy—that anticipate and adapt to evolving compliance demands, thereby minimizing disruption from policy shifts.^[130] Regarding Big Tech oversight, Calacanis has acknowledged the rationale for antitrust measures against dominant platforms, appearing on CNBC in July 2021 to discuss lawmakers' concerns over their market power and influence on information flow.^[131] ^[132] He supports user-empowering reforms, such as mandating transparency in social media algorithms to allow individuals to select preferred feeds, arguing this would counteract opaque curation that amplifies biases or misinformation.^[133] Yet, he cautions against regulatory capture, where incumbents exploit rules to entrench advantages, as explored in All-In Podcast episodes critiquing barriers in industries from pharmaceuticals to services.^[134] Calacanis's views extend to selective government intervention in crises affecting tech ecosystems. During the March 2023 Silicon Valley Bank collapse, he urged federal authorities to guarantee all depositors—predominantly tech startups and venture firms—beyond the standard FDIC limit, emphasizing the sector's economic centrality and the risk of cascading failures without swift action.^[135] This position, which aligned with the eventual FDIC decision to protect uninsured deposits, underscores his belief in targeted state support to preserve innovation hubs, even as he critiques broader overreach that could hinder entrepreneurial agility.^[136] In AI infrastructure contexts, he has welcomed U.S. executive orders facilitating data centers while stressing the need to harmonize regulations with energy and security imperatives to sustain competitive edges.^[137]

Engagements with Political Figures

Calacanis has primarily engaged political figures through interviews on the All-In Podcast and associated summits, often probing policy implications for technology and business. On June 20, 2024, he participated in a group interview with former President Donald Trump alongside co-hosts Chamath Palihapitiya, David Sacks, and David Friedberg, covering topics including potential National Guard deployment in San Francisco, U.S.-China trade tensions over rare earths, and artificial intelligence's public relations challenges.^[138] This marked a notable interaction despite Calacanis' prior public statements of personal antipathy toward Trump; in July 2020, he described himself as hating Trump but credited the administration's Paycheck Protection Program with saving millions of jobs amid the COVID-19 economic shutdown.^[139] To demonstrate balance, Calacanis and the All-In hosts interviewed Democratic presidential candidate Dean Phillips on November 17, 2023, discussing Phillips' business background in distilling, his congressional tenure, and critiques of party leadership on issues like inflation and foreign policy.^[140] Phillips, a moderate challenging incumbent Joe Biden, used the platform to highlight economic concerns affecting small businesses, aligning with Calacanis' investor perspective. Calacanis directly questioned Vice President JD Vance during the All-In Summit on September 9, 2024, pressing on Vance's hypothetical refusal to certify the 2020 election results, deportation logistics for undocumented immigrants, and U.S. innovation challenges.^[141] Vance responded by advocating state-submitted alternative elector slates and emphasizing enforcement priorities, revealing tensions with Calacanis over immigration's labor market impacts. Following Vance's ascension to the vice presidency after the 2024 election, Calacanis met him in Washington, D.C., around early August 2025 to debate H-1B visa program integrity, including allegations of fake job postings to exploit the system for lower-wage foreign talent over domestic workers.^[142] Calacanis advocated educating policymakers on misuse patterns, reflecting his ongoing focus on talent competition in tech.

Controversies and Criticisms

Legal and Business Disputes

In November 2010, Jason Calacanis filed a lawsuit in San Francisco Superior Court against Interserve Inc., doing business as TechCrunch, alleging fraud related to their prior partnership on the TechCrunch50 conference series.^[143] The suit stemmed from a breakdown in their collaboration, where Calacanis claimed TechCrunch had misrepresented aspects of the event's ownership and operations after he had contributed significantly to its development and execution starting in 2007.^[144] Prior to filing, Calacanis had sent a demand letter threatening legal action, asserting rights to aspects of the conference format and branding that he believed were co-developed.^[145] The dispute highlighted tensions between Calacanis and TechCrunch founder Michael Arrington, with Calacanis accusing the company of exploiting his involvement without fair compensation or credit following their 2009 separation from the partnership.^[144] TechCrunch countered publicly, portraying the claims as an attempt to challenge a prior settlement agreement and denying any fraud, while noting Calacanis had benefited from the events' success.^[144] No monetary damages were publicly specified in initial filings, but the case centered on intellectual property and contractual rights tied to the conference's structure, which Calacanis later adapted for his competing Launch event.^[145] On March 2, 2011, shortly after hosting the inaugural Launch Conference, Calacanis voluntarily dismissed the lawsuit without prejudice, effectively ending the legal proceedings without a trial or settlement disclosure.^[146] Court records indicate the dismissal was requested by Calacanis' side, suggesting a strategic withdrawal possibly to focus on his independent ventures amid the competitive startup event landscape.^[146] No further litigation arose from this partnership fallout, though it underscored Calacanis' pattern of aggressive business positioning in the tech media and events space.^[146] Beyond this case, Calacanis has not been involved in other publicly reported lawsuits as plaintiff or defendant in business matters, though he has publicly criticized practices like fee-charging angel investor groups in 2009, prompting defensive responses but no legal escalation.^[147]

Public Feuds and Interpersonal Conflicts

In 2010, Calacanis engaged in a public dispute with TechCrunch founder Michael Arrington over the dissolution of their partnership in the TechCrunch50 conference series, which had begun in 2007.^[144] Tensions escalated after TechCrunch's acquisition by AOL, with Calacanis demanding a share of the proceeds and accusing the company of intellectual property theft, while Arrington attributed the partnership's end to Calacanis's unprofessional conduct, including vetoing decisions, drunken behavior at events, and spreading unsubstantiated rumors about Arrington's personal life.^[144] Calacanis issued a demand letter and draft complaint threatening litigation, but no lawsuit materialized, and TechCrunch proceeded with its Disrupt conference independently.^[144] Calacanis has maintained a longstanding public antagonism toward New York University professor and podcaster Scott Galloway, stemming from Galloway's criticisms of startups like Uber and Robinhood in which Calacanis held early investments.^[148] Between 2018 and 2022, Calacanis directed over 150 targeted tweets at Galloway, often deriding his business commentary and stock-picking abilities, which Galloway described as a "creepy obsession."^[149]^[150] A notable interpersonal conflict arose with entrepreneur Palmer Luckey, originating in 2016 when Calacanis publicly condemned Luckey's funding of Nimble America, a group producing anti-Hillary Clinton memes during the U.S. presidential election, arguing it damaged the technology industry's reputation.^[151] Luckey, who faced professional repercussions including his departure from Oculus VR (then under Meta), accused Calacanis of hypocrisy and bullying for prioritizing industry image over free speech.^[152] The feud resurfaced at the 2023 All-In Summit, where Luckey directly challenged Calacanis during a fireside chat, though the two exchanged a handshake afterward; underlying tensions persisted into 2024 via exchanges on X (formerly Twitter).^[151]^[152] In October 2022, Calacanis and All-In Podcast co-host David Sacks aired a brief Twitter disagreement over podcast moderation policies, which they publicly resolved through direct discussion on the platform and subsequent episodes.^[153] Calacanis has also publicly criticized figures like marketing consultant Neil Patel and investor Robert Herjavec in 2019 for promoting what he deemed fraudulent entrepreneurial schemes, though these exchanges did not escalate into sustained personal conflicts.^[154]

Accusations of Bias and Hypocrisy

In 2016, Jason Calacanis criticized Palmer Luckey, the founder of Oculus VR, for anonymously funding Nimble America, a political action group that produced pro-Donald Trump and anti-Hillary Clinton memes, contending that such partisan activities risked reputational harm to the broader technology sector and could provoke consumer boycotts.^[152] This stance contributed to heightened scrutiny of Luckey, who was dismissed from Facebook (now Meta) in 2017 without an official reason, though the timing aligned with the political backlash.^[151] Calacanis, described as a progressive-leaning investor and vocal critic of Trump, framed Luckey's actions as incompatible with Silicon Valley's prevailing norms, prompting accusations from Luckey that Calacanis exhibited bias against conservative viewpoints under the guise of industry protection.^[151] The dispute resurfaced publicly in October 2024 at the All-In Summit, where Luckey directly accused Calacanis of hypocrisy, labeling his conduct as representative of "hypocrisy and toxicity" within Silicon Valley elites who demand tolerance but demonstrate intolerance toward political nonconformity.^[152] Luckey specifically cited Calacanis's alleged bullying of critics and persistent tracking of adversaries following professional disputes, such as post-firing vendettas, as evidence of inconsistent principles—contrasting Calacanis's advocacy for open discourse in tech with personal adversarial tactics.^[151] Even All-In Podcast co-host David Friedberg, a collaborator with Calacanis, acknowledged that Calacanis's confrontational style "leaves emotional debris," underscoring perceptions of selective application of interpersonal standards.^[151] These claims, originating from Luckey—a self-made billionaire via Oculus's $2 billion acquisition by Facebook in 2014—highlight tensions over ideological conformity in venture capital circles, where Calacanis's earlier support for Democrats like Clinton has fueled narratives of partisan double standards.^[155] Critics have extended hypocrisy allegations to Calacanis's role in the All-In Podcast, arguing it shifted from balanced analysis to accommodating Republican-leaning rhetoric despite hosts like Calacanis maintaining prior Democratic affiliations, though Calacanis has defended his positions as pragmatic investor realism rather than ideological flip-flopping.^[156] Such accusations, often aired on platforms like Reddit and X, reflect broader Silicon Valley divides but lack formal adjudication, relying on public exchanges where Calacanis's outspokenness invites scrutiny of perceived inconsistencies between his free-market advocacy and selective political tolerances.^[157]

Publications and Thought Leadership

Major Books and Writings

Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 is Jason Calacanis's principal book on angel investing, published by HarperBusiness on July 18, 2017.^[158] The 288-page volume synthesizes Calacanis's approach to early-stage investments, asserting that he transformed an initial $100,000 into $100 million through stakes in high-growth companies like Uber.^[41] It targets novice investors, advocating a systematic process for sourcing, evaluating, and syndicating deals while stressing founder resilience over polished presentations.^[159] Calacanis structures the book around practical frameworks, including due diligence checklists and portfolio management tactics to limit losses in a high-failure-rate domain where over 90% of startups fail.^[160] He promotes investing in familiar markets and leveraging networks for co-investments, drawing from his track record of over 100 early bets by the time of publication.^[161] The text critiques common pitfalls like chasing hype without conviction, positioning disciplined volume—reviewing hundreds of opportunities annually—as essential for outsized returns.^[162] Beyond the book, Calacanis has produced notable essays on investing principles, including "Calacanis' Two Laws of Angel Investing," a 2015 Medium article distilling success to generating consistent deal flow and applying rigorous, unbiased screening to avoid emotional biases. These writings prefigure themes in Angel and reflect his broader output via platforms like Inside.com, which he founded in 2019 to curate expert newsletters on technology and startups.^[163] His Substack, "Jason Calacanis on Startups," continues this tradition with periodic analyses of market dynamics, funding rounds, and founder strategies, often informed by his ongoing syndicate investments.^[164]

Influence on Startup Ecosystem

Calacanis has exerted influence on the startup ecosystem primarily through angel investing, educational events, and media platforms that democratize access to venture knowledge. As an early-stage investor, he has backed over 150 technology startups, with notable successes including Uber, where he participated in one of the initial seed rounds in 2010, contributing to the company's rapid scaling and eventual $82 billion valuation at IPO in 2019.^[165] His personal investment portfolio, starting with approximately $700,000, has grown to over $100 million in value, demonstrating a high return profile that has encouraged other individual investors to enter the angel space.^[34] Calacanis invests in roughly 100 new startups annually via his LAUNCH Syndicate, a platform that aggregates deal flow from his network and enables co-investments, thereby amplifying capital availability for seed-stage founders.^[51] Through the LAUNCH conference series, initiated in 2011, Calacanis has facilitated connections between entrepreneurs and investors, hosting pitch events that distributed $1 million in prizes during early iterations and evolving into a selective accelerator program.^[166] The associated LAUNCH Fund, launched in 2013, exclusively targeted startups emerging from these events, providing structured funding and mentorship that supported dozens of companies in achieving product-market fit.^[167] This model has influenced accelerator practices by emphasizing rapid iteration and investor-founder alignment, with participants gaining exposure to high-profile venture capitalists.^[168] The "This Week in Startups" podcast, hosted by Calacanis since 2009, has interviewed hundreds of founders and investors, offering tactical advice on fundraising, scaling, and market timing that reaches over a million listeners annually.^[68] Episodes dissecting bull markets, AI disruptions, and regulatory challenges have shaped founder strategies, as evidenced by recurring themes of disciplined capital allocation cited in subsequent startup pitches.^[6] His book "Angel: How to Invest in Technology Startups—Timeless Ventures from an Angel Investor," published in 2017, codifies these insights, advocating for diversified portfolios and due diligence processes that have lowered barriers for non-institutional investors entering the ecosystem.^[62] Collectively, these efforts have promoted a merit-based, high-velocity approach to innovation, countering overly speculative trends by prioritizing verifiable traction metrics.^[55]

Personal Life

Family and Relationships

Calacanis is married to Jade Li Calacanis, whom he met while building his career in Los Angeles.^[20] The couple wed in 2006 and have maintained a low public profile regarding their relationship.^[169] ^[170] They have three daughters, with whom Calacanis co-hosts the "Daddy Daughter Podcast," a program featuring discussions on family, business, and personal growth.^[171] Calacanis has two brothers and was raised in a family of Greek and Irish descent in Brooklyn's Bay Ridge neighborhood.^[11]

Lifestyle and Net Worth Estimates

Jason Calacanis's net worth is estimated to range from $60 million to $200 million as of 2025, with analyses from venture-focused sources converging around $100-170 million based on his angel investment returns and business exits.^[47]^[172] Lower estimates, such as $60 million from aggregated celebrity wealth trackers, appear outdated and undervalue his portfolio gains from private equity stakes.^[173] These figures derive primarily from the 2005 sale of his blog network Weblogs, Inc. to AOL for approximately $30 million (with Calacanis's share estimated at $10-15 million) and subsequent angel investments exceeding 800 startups, including early bets on Uber that reportedly multiplied initial outlays of tens of thousands into nine-figure returns.^[174]^[175] Calacanis maintains a relatively low-profile lifestyle centered in Los Angeles, where he has long resided and operates his podcast and investment activities. In 2023, he sold a Brentwood property for $2.92 million, indicative of upscale but not extravagant real estate holdings in the region.^[170] Public details on personal expenditures, such as vehicles or luxury purchases, remain scarce, aligning with his public emphasis on disciplined capital allocation in startups over conspicuous consumption; he has described his approach in interviews as prioritizing asymmetric investment upside over lifestyle inflation.^[176] His routine involves hosting "This Week in Startups" and moderating the "All-In" podcast, activities that sustain his influence without evident reliance on high-visibility opulence. Estimates of his wealth's liquidity are complicated by illiquid private holdings, contributing to the wide variance in reported figures.^[177]

References

[1]
Jason Calacanis Speaking Fee & Booking Agent Contact
Jason Calacanis Biography. Jason McCabe Calacanis born November 28, 1970, from Brooklyn New York is an American Internet business person, ...
[2]
Jason Calacanis - Founder & CEO @ LAUNCH - Crunchbase
Jason Calacanis is the Founder and CEO of Inside.com and Launch. He previously worked at Weblogs as a Co-Founder and CEO. Jason Calacanis attended Fordham ...
[3]
AOL Acquires Weblogs, Inc. - TechCrunch
Oct 5, 2005 · The acquisition price, including earnouts, is reported to be $20-35 million. Weblogs, Inc., founded by Jason Calacanis and Brian Alvey was ...
[4]
How Insiders Describe Early Robinhood Investor Jason Calacanis
Jun 7, 2021 · He was among the first VC investors in Uber, Calm and Robinhood, among others, and he runs the boot-camp-like Launch "accelerator" to help ...
[5]
Jason Calacanis Net Worth and His Investment Thesis for U.S. ...
Mar 16, 2025 · Best known for his early bet on Uber, he has invested in over 300 startups, including Robinhood, Calm, and Thumbtack. But beyond his wealth ...
[6]
This Week in Startups
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world's greatest founders.Jason Calacanis · All episodes · TWiST Ticker · Our audience
[7]
LAUNCH
This Week In Startups with Jason Calacanis. ‍ All-In with Chamath Palihapitiya, Jason Calacanis, David Sacks, and David Friedberg. Accelerator · LAUNCH ...
[8]
Jason Calacanis On the Expensive Lesson Coming to Silicon Valley
Jul 21, 2022 · On this episode we speak with long-time angel investor and co-host of the 'All-In' podcast Jason Calacanis, who was early into companies like ...
[9]
Musk's Twitter Fix-It Team Fades Out as Billionaire Says Transition Is ...
Nov 19, 2022 · Calacanis, Krishnan and Sacks were added to Twitter's internal Slack messaging account, according to a person familiar with the situation, along ...
[10]
Jason Calacanis: The No1 Greek Internet Brain - GreekReporter.com
Dec 11, 2008 · What is your Greek Background? My father is Greek. Have you ever been in Greece? Yes, twice. What do you think of the ...
[11]
Jason Calacanis: Age, Net Worth, Family, Career Highlights & More
Jan 28, 2025 · Full Name, Jason McCabe Calacanis ; Date of Birth, November 28, 1970 ; Place of Birth, Bay Ridge, Brooklyn, New York, U.S. ; Nationality, American.
[12]
Jason Calacanis' Net Worth and Investor Story
Jul 6, 2023 · With early angel investments in companies like Uber and Robinhood, Jason Calacanis turned $100,000 into $100 million. Calacanis co-founded ...
[13]
Jason Calacanis: Behind the Scenes of This Week in Startups
Sep 25, 2019 · Jason's Crazy Childhood · Jason grew up in Brooklyn, NY in the 1970s/80s · One particular set of memories: hanging around his dad's bar/restaurant ...
[14]
The Rise and Fall and Rise of Jason Calacanis: In His Own Words
All of which was at Calacanis whim and discretion, but then, he was not one to shrink from controversy: in fact, he openly courted it. Having seen his ...Missing: controversies | Show results with:controversies
[15]
Special Episode: Jason Calacanis | Acquired Podcast
Apr 28, 2020 · I had this amazing, hardworking mother doing three or four jobs and this amazingly hard working dad. It was a blue collar lifestyle, we ...
[16]
Full transcript: Podcaster, entrepreneur and angel investor Jason ...
Apr 12, 2017 · I was basically, at the age of 17, my dad lost everything and was on the brink of going to jail for tax evasion. I think it just became my ...
[17]
Jason Calacanis: Startup Impresario - Fordham Now
Jul 20, 2016 · Brooklyn-born entrepreneur and angel investor Jason Calacanis aims to bring the real Silicon Valley to TV.
[18]
Jason Calacanis To Keynote Pubcon Las Vegas 2014
Jun 30, 2014 · Calacanis, who attended Fordham University majoring in psychology, is known for his insights into the media and technology industries, and he is ...
[19]
Renowned “Angel” Jason Calacanis Shares Advice On ...
Jul 26, 2017 · “Doing hard work and trying to be successful is a good thing,” he said. Calacanis went to Fordham University at night, while working as a waiter ...
[20]
From The Vault Jason Calacanis | Startup Grind
Jason is now the CEO of Mahalo.com based in Santa Monica; he is an avid angel investor with companies like Uber, Gawala, Reportive, Uber Media, Chart Beat, and ...
[21]
The Connector | The New Yorker
Oct 11, 1999 · In his current incarnation, Calacanis is the founder of a miniature media empire that began, three years ago, with the Silicon Alley Reporter, a ...
[22]
Jason Calacanis - TWiT Network
Prior to forming Weblogs Inc., Calacanis was the founder of Rising Tide Studios, a media company that published the magazines Silicon Alley Reporter and Digital ...
[23]
Jason Calacanis | What's new, new media? - Fandom
During the dot-com boom, he was active in New York's Silicon Alley community and in 1996 began producing a publication known as the Silicon Alley Reporter.
[24]
Serial entrepreneur of the Internet - ellines.com
He graduated from the Xaverian High School, in 1988, and then received a BA in Psychology from Fordham University. Initially, he was founder and CEO of ...
[25]
6 Lessons Learned from Weblogs Inc and Jason Calacanis - Smash.vc
So, Calacanis planted false rumors about the business, and Denton published them. He only learned later that the rumors actually came from Calacanis himself.6 Lessons Learned · 1. Get Lucky, Early And... · 6. Own The Narrative...
[26]
Episode 37: Uber's first investor - Jason Calacanis the GREATEST ...
Mar 12, 2025 · Episode 37: Uber's first investor - Jason Calacanis the GREATEST ... Robin Hood; as well as selling shares in Facebook (whilst telling ...
[27]
Jason Calacanis, Launch Festival - CXOTalk
Since 2009, Calacanis has been the host of popular podcast "This Week in Startups,” the largest talk show about technology and startups in the world. Past ...
[28]
How a founder went from being worth millions to - Yahoo Finance
Aug 3, 2017 · Calacanis went on to start Weblogs and sold it 18 months later to AOL for about $30 million. But he's made the most money as an angel investor.<|control11|><|separator|>
[29]
AOL buys blog network Weblogs Inc. - NBC News
Oct 6, 2005 · Jason McCabe Calacanis, co-founder and chief executive of Weblogs, has said that Weblogs gets more than $1 million a year by participating ...
[30]
Time Warner's AOL Acquires Blog Network 10/07/2005 - MediaPost
... Weblogs, a network of blogs founded by Jason Calacanis and Brian Alvey, for $25 million. The deal marks the second major media company to move into the so ...
[31]
Report: AOL buying Weblogs Inc. - CNET
Oct 6, 2005 · PaidContent estimated the purchase price at anywhere from $20 million to $35 million.
[32]
Mahalo.com: Pivot or Die - Fast Company
Jun 4, 2012 · After selling his blog syndicate Weblogs, Inc. for around $20 million and spending a year as an executive at AOL, Jason Calacanis departed ...
[33]
Jason Calacanis on how to attract angel investors - The Intercom Blog
Jul 13, 2017 · World renowned angel investor Jason Calacanis shares what he looks for in founders, when founders should begin pitching angel investors, ...
[34]
Jason Calacanis - Angel Invest Boston
Nov 13, 2019 · Silicon Valley angel investing phenomenon Jason Calacanis is our guest. Hear how he turned $700K into a portfolio worth $100 million.
[35]
Inaugural Open Angel Forum Was a Success | by Mark Suster
Jan 15, 2010 · Jason started the Open Angel Forum in response to his frustration that entrepreneurs were being charged by some angel organizations to present ...Get Mark Suster's Stories In... · Is It Time For You To Earn... · I'm About To Offer You Some...<|separator|>
[36]
Angel: Timeless Advice from an Angel Investor Who Turned ...
Billion-dollar unicorns are rare, with only 12-24 created annually -- but Jason hit three in his first 50 investments, including juggernauts Uber and Thumbtack ...
[37]
A Dozen Lessons about Angel Investing from Jason Calacanis ...
Aug 4, 2017 · Calacanis says: “I have a theory about angel investing, which is basically you're investing in the person and that the more outlandish the idea ...
[38]
Entrepreneur Jason Calacanis on the Evolution of the Internet ...
Oct 6, 2019 · Calacanis was hired to scout for Sequoia Capital, helping land deals with companies like Uber, and then set off down his own path in angel and ...
[39]
Jason Calacanis Net Worth and Angel Investing Playbook ... - Capitaly
Sep 22, 2025 · From his $25K check into Uber to hundreds of angel deals through LAUNCH and the Syndicate, Calacanis has built a repeatable angel investing ...
[40]
How This Angel Investor Turned $100K Into $100 Million
Sep 18, 2018 · Jason Calacanis is one of Silicon Valley's leading angel investors. Over the past seven years, Calacanis has invested in more unicorn companies ...<|separator|>
[41]
Amazon.com: Angel: How to Invest in Technology Startups-Timeless ...
The trick is learning how angel investors think. Calacanis takes you inside the minds of these successful moneymen, helping you understand how they prioritize ...
[42]
E14: Jason Calacanis on How He Returned 4000X ($25K into $100 ...
E14: Jason Calacanis on How He Returned 4,000X ($25K into $100MM) on a Single Investment. E14 • Oct 22, 2023 • 40 mins. Jason Calacanis, founder of LAUNCH and ...
[43]
The Syndicate
TheSyndicate.com is an angel investing club led by Jason Calacanis. Jason Calacanis has invested in over 300 startups in the past decade.
[44]
Jason's Syndicate
A group of 10000+ accredited investors led by Jason Calacanis that invests in world-class founders.
[45]
Inside a Jason Calacanis Syndicate: SPVs, Fees, Carry, and ...
Oct 11, 2025 · A practical guide to Jason Calacanis syndicate economics: SPVs, carry, platform fees, term sheets, and negotiation tips for founders raising ...
[46]
Direct Startup Investing vs. Syndicate Investing: Which Path Is Right ...
Syndicate investing lets investors pool funds under a lead investor who sources deals, performs diligence, and negotiates terms. You commit capital to the ...
[47]
Jason Calacanis Net Worth in 2025: The Complete Breakdown of ...
Jun 12, 2025 · Calacanis built his wealth through selling Weblogs, Inc. to AOL for $30 million, then investing the proceeds in startups like Uber, which ...
[48]
Meet Jason Calacanis: Launch Accelerator's Leader - XRaise blog
Apr 22, 2025 · Discover Jason Calacanis 's journey, investment strategy, and founder-first philosophy—essential insights for early-stage startup founders.
[49]
LAUNCH Accelerator with Aisha Chottani - Boring Business Nerd
Jason Calacanis plays an active role in each startup accepted into the LAUNCH accelerator. He gives direct feedback regarding the startup's pitch, product ...<|separator|>
[50]
LAUNCH Accelerator Cohort 35 is accepting applications!
Aug 6, 2025 · A 14-week program to help entrepreneurs start, build, and scale a food business. Jul 19, 2023 • jason@calacanis.com.
[51]
Jason Calacanis - I invest in 100 new startups a year... get ... - LinkedIn
I invest in 100 new startups a year... get a meeting with my team at launch.co/apply, or learn how to start a company by joining founder.university (our 12-week ...
[52]
LAUNCH - Crunchbase Company Profile & Funding
Photo of Jason Calacanis. Jason Calacanis: Founder & CEO. Past Role: This Week ... Funding Round: Name of the funding round where the Investment is made.<|separator|>
[53]
Founder University | Transform Your Startup Now
Founder University is a 10-week pre-accelerator helping tech startups build, launch, and delight customers. · We invest $25k or $125k into the top graduates.
[54]
Jason Calacanis | Wellfound
Investor in over 300 startups, including Uber, Robinhood & Calm. Founder and CEO of LAUNCH: www.launchaccelerator.co www.thesyndicate.com www.angel.universityMissing: details | Show results with:details<|control11|><|separator|>
[55]
Trailblazer: Jason Calacanis on the state of the Venture Industry
Nov 9, 2023 · Calacanis and Ressi explore the impact of new investors entering the field, the shift in investment strategies, and the changing role of ...
[56]
Interview with Jason Calacanis: Investor in Uber - Medium
Mar 16, 2016 · Jason was the first scout at Sequoia Capital and is an investor in Uber, Thumbtack and over 100 other startups. Here are a few of my favorite ...
[57]
Startups are feeling the squeeze as funding dries up. With 254 ...
Aug 20, 2024 · Jason Calacanis Jason Calacanis is an Influencer. I invest in 100 ... And so here we have annual failure rate according to Carter again ...
[58]
How Jason Calacanis turned $100K into $100M - Medium
Oct 19, 2021 · With early angel investments in companies like Uber and Robinhood, Jason Calacanis managed to turn 100 thousand dollars into 100 million.
[59]
The failure of Circa from Jason Calacanis, one of their investors ...
Jul 2, 2015 · The failure of Circa from Jason Calacanis, one of their investors. Points at the failure of non-sensationalised news and listicles.Missing: investments | Show results with:investments
[60]
https://venturebeat.com/media/jason-calacanis-admits-inside-com-news-app-failed-pivots-to-an-email-service
[61]
FOUNDERS, BEWARE OF CORPORATE VC! WHOOP CEO Will ...
Aug 2, 2023 · Jason Calacanis Jason Calacanis is an Influencer. I invest in 100 new ... No offense, Calacanis, you've made impressive investments.
[62]
Angel by Jason Calacanis Book Review - Technology Blog
Dec 12, 2023 · In conclusion, “Angel: How to Invest in Technology Startups” is a refreshingly honest and insightful guide to the world of angel investing.
[63]
Angel by Jason Calacanis - Book Review and Key Lessons
Feb 11, 2019 · ... failure, more potential dilution, and many other risks to maximizing your returns. ... investment exits and failures. Learn to navigate startup ...
[64]
Angel | Book by Jason Calacanis - Curious Compass
Jun 26, 2023 · Angel investing is a financial endeavor where individuals target businesses that are typically less than three years into their operation. Often ...
[65]
This Week in Startups (Podcast Series 2009– ) - IMDb
Rating 7.6/10 (10) This Week in Startups: With Jason Calacanis, Molly Wood. Entrepreneur Jason ... Release date · May 2, 2009 (United States). Country of origin. United ...
[66]
Episodes - This Week in Startups
This Week in Startups. Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology.
[67]
This Week in Startups | LinkedIn
This Week in Startups (TWiST) is a weekly show hosted by technology investor Jason Calacanis, along with co-hosts Alex Wilhelm and Lon Harris.
[68]
This Week in Startups - Apple Podcasts
Rating 4.2 (1,266) Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world's greatest founders.
[69]
Did Jason Calacanis screw over Leo Laporte when he started his ...
Jun 29, 2010 · What ever happened to Jason Calacanis's "This Week In Startups" podcast? Back and going strong! Here is a link to the last one - http://www ...
[70]
Steve Jobs' podcasting vision and Apple's secrecy - LinkedIn
Feb 24, 2025 · Calacanis cast which eventually became this program this week in startups and we did a podcast for Autoblog which were two of the 1st 5 to ...
[71]
How to raise venture capital: Master the 5 levels of Founder ...
Oct 3, 2025 · Want to know the secret to raising venture capital? Learn, nay MASTER, the five levels of Founder Fundability… On a brand new TWiST, ...
[72]
This Week in Startups - Podcast Analytics & Insights - Podscan.fm
Get detailed analytics, audience insights, and performance metrics for This Week in Startups. Access listener demographics, contact information, ...<|separator|>
[73]
This Week in Startups with Jason Calacanis - Podcast Notes
Anthony Pompliano and Jason Calacanis discuss Crypto ICOs, fundraising for startups, investing, Bitcoin, and competition with big
[74]
Ask Jason LIVE!: Navigating startup growth with Real-Time Q&A
Apr 24, 2024 · 5 live guests ask questions on key topics, including finding job opportunities, the “likely winner” and “definitive winner” framework, how a non ...
[75]
preparing this weeks All In and Today's This Week in Startups dockets
Feb 24, 2025 · 23 votes, 79 comments. do you have any topics, videos, charts or news stories you want me to put on the docket for the two shows?
[76]
#startups #internet #starlink #regulation #elonmusk | Jason Calacanis
... Elon Musk, spurred on by the current administration. Carr actually broke down the cost comparison on a recent episode of This Week in Startups. The cost to ...
[77]
This Week in Startups | Podcast directory - Poor Stuart's Guide
Sep 3, 2021, Adrian Grenier: launching a new fund + FounderU: balancing product vision & customer feedback - E127 (00:57), Details/Play ; Sep 2, 2021, Next ...
[78]
Bookmarks | Episode List on Podchaser
... This Week in Startups and Angel. Before this interview was recorded, Jason ... Guests. Steve Wozniak,John Sculley. Add to List. Reed Duchscher - On ...
[79]
Episodes of This Week in Startups | Podchaser
Guests. Peter Chen. Add to List. E40: “Angel” Podcast: Jeff Richards, Managing Partner at GGV Capital shares · This Week in Startups · Active.Missing: notable | Show results with:notable
[80]
The 8 Best This Week in Startups Podcast Episodes - Podyssey
5) E817: News Roundtable! Gadget Guy Dave Mathews (NewAer ) & Austin Smith (Inside.com): Elon rants at investors, Facebook steals again w/Dating, Telegram ...
[81]
This Week in Startups (Podcast) - Podchaser
Rating 4.8 (5) With Molly Wood and Jason Calacanis, 1326 episodes, 5 ratings & reviews. Jason Calacanis covers startups, tech, markets, media, and all the hottest topics ...
[82]
Listener Numbers, Contacts, Similar Podcasts - This Week in Startups
Rating 4.3 (2,968) See the number of listeners, audience demographics, contact info, reviews and recent guests to decide if it's worth pitching This Week in Startups.
[83]
What are the best business podcasts in 2025?
May 29, 2025 · Jason Calacanis ("The Moderator"): Early Uber/Robinhood investor and "This Week in Startups" host who facilitates the podcast's discussions.Foundr: A Decade Of... · Girls That Invest: Breaking... · The Diary Of A Ceo: A Fresh...Missing: origins | Show results with:origins
[84]
[PDF] The Project To Popularize Startup Investing - UC San Diego
https://ccst.us/wp-content/uploads/CREST5.pdf. Page 229. 218. Calacanis, Jason [This Week in Startups] (2013). Hacking AngelList syndicates with cofounder.
[85]
Reviews For This Week in Startups - PodParadise
Good content but too many ads. 2/5 ... The content and insights are good but the ridiculous number of imbedded ads make this only an occasional listen now. Jason ...
[86]
JCal's sidekick Molly Wood has left This Week in Startups Podcast
Mar 21, 2023 · Check Apple Podcasts, not talking about number of viewers just star ratings. It's been dropping since Molly came on and the format changed.
[87]
Jason Calacanis (the most successful Angel Investor of all time) just ...
Aug 28, 2019 · Jason Calcanis just publicly called out Neil Patel, Timothy, and Robert Herjavec for trying to swindle people with their newly announced project together.Jason Calacanis is a moron. - TheAllinPodcasts - RedditThe Fallout Between Palmer Luckey and Jason Calacanis ... - RedditMore results from www.reddit.com
[88]
All-In with Chamath, Jason, Sacks & Friedberg (Podcast Series 2020
Rating 7.2/10 (23) Details ; Release date · March 19, 2020 (United States) ; Official sites · Official Site ; Also known as. All-In Podcast.
[89]
About - All-In Podcast
Jason Calacanis is a technology entrepreneur, fund manager, host of This Week in Startups podcast and co-host and executive producer of the All-In Podcast.
[90]
All-In with Chamath, Jason, Sacks & Friedberg - Apple Podcasts
Rating 4.0 (9,017) Industry veterans, degenerate gamblers & besties Chamath Palihapitiya, Jason Calacanis, David Sacks & David Friedberg cover all things economic, tech, political ...
[91]
Jason Calacanis Tells the Origin Story of The All-In Podcast - YouTube
Nov 22, 2022 · ... influence of his podcast, The Tim Ferriss Show, which has exceeded 800 million downloads and been selected for “Best of Apple Podcasts ...
[92]
The All-In podcast is a fascinating, infuriating safe space for Silicon ...
Jan 12, 2023 · Calacanis already had a popular show of his own (This Week in Startups, on which Palihapitiya had previous appeared), but he agreed to the new ...<|separator|>
[93]
https://allin.com/
[94]
The Besties' Revenge: How the 'All-In' Podcast Captured Silicon Valley
Dec 15, 2023 · Jason Calacanis, David Friedberg, David Sacks and Chamath Palihapitiya have set their sights well beyond their Silicon Valley sphere of influence.
[95]
How Jason Calacanis Grew His Influence and Net Worth - Capitaly
Aug 13, 2025 · Jason Calacanis is an early-stage investor, entrepreneur, and media personality. He made his mark with early investments in Uber, Robinhood, and ...Missing: mentors | Show results with:mentors
[96]
The "All-In" podcast has hit a new low by hosting Donald Trump, and ...
Jun 21, 2024 · The "All-In" podcast has become a real-time case study in self-destruction, grifting, and public embarrassment. Enjoy the spectacle if you can stomach it.Missing: topics | Show results with:topics
[97]
What sparked the Twitter feud? | Ask Dexa
The Twitter feud between Jason Calacanis and David Sacks on the All-In Podcast started over podcast moderation issues.<|separator|>
[98]
Jason Calacanis: From Angel Investor to All-In Podcast Mogul
Aug 13, 2025 · His early career was in media and publishing, running the Silicon Alley Reporter, a magazine that chronicled the rise of New York's internet ...
[99]
About - Jason Calacanis - All-In Podcast
Jason Calacanis is a technology entrepreneur, fund manager, host of This Week in Startups podcast and co-host and executive producer of the All-In Podcast.<|separator|>
[100]
https://www.vanityfair.com/news/story/all-in-is-coming-for-everyone-else
[101]
The 'All-In' Hosts Make the Leap from Investors to Influencers
Dec 18, 2023 · The hosts, entrepreneurs and tech investors Jason Calacanis, David Friedberg, Chamath Palihapitiya and David Sacks, have successfully used the show to snatch ...
[102]
https://www.allin.com/
[103]
Inside the White House Tech Dinner, Weak Jobs Report, Tariffs ...
Sep 7, 2025 · Inside the White House Tech Dinner, Weak Jobs Report, Tariffs Court Challenge, Google Wins Antitrust. 344K views · 1 month ago All-In ...Missing: episodes themes
[104]
The All-In Podcast (@theallinpod) / Posts / X
The All-In Podcast✓ ... @chamath, @jason, @davidsacks, and @friedberg cover all things economic, tech, political, social, and poker.
[105]
All-In with Chamath, Jason, Sacks & Friedberg (Podcast Series 2020
The four hosts engage in deep discussions on diverse topics including Ivy League antisemitism hearings, the state of the consumer economy, and trends in the ...
[106]
https://www.facebook.com/JoeManchinIII/posts/had-a-great-discussion-with-chamath-palihapitiya-and-jason-calacanis-this-week-o/1386844699473977/?locale=be_BY
[107]
All-In with Chamath, Jason, Sacks & Friedberg - Podcast Ranking
Their influence, particularly on impressionable listeners, could promote a worldview that prioritizes profit over people and planet. I urge listeners to ...
[108]
VCs Sacks, Palihapitiya Land Trump as All-In Podcast Guest
Jun 20, 2024 · Sacks in particular has criticized President Joe Biden's policies, including what he sees excessive spending on Covid relief and too much ...
[109]
What Side Are the 'All-In Pod' Bros On? - Gizmodo
Jun 9, 2025 · The Silicon Valley podcasters are torn between their two favorite fascists. ... Jason Calacanis, Chamath Palihapitiya, David Friedberg, and ...
[110]
Listener Numbers, Contacts, Similar Podcasts - All-In - Rephonic
Rating 4.3 (34,880) This show is now disappointing for all the reasons it used to be great. They have sold out - and with it the takes have become expected and uninteresting.
[111]
Learning not to trust the All-In podcast - Hacker News
Nov 10, 2024 · In recent years we've seen where the loyalties lie for the likes of Sacks and Calacanis. You see this as various SV movers have fallen in line ...
[112]
Jason Calacanis' Post - LinkedIn
Jan 7, 2025 · The UK needs to rethink its economic policies to encourage economic activity, thereby producing more employment, investment, and tax revenue.
[113]
Time for a pledge to control government spending
Aug 8, 2025 · Calacanis and his All-In co-hosts are spot on about the need for a massive downshift in the rate of growth in government spending. The numbers ...
[114]
Government Spending Cuts | Ask This Week in Startups - Dexa.ai
Government Spending Cuts. The discussion centers around the potential for significant budget cuts within government departments by reducing personnel costs.
[115]
All-In Podcast host Jason Calacanis says Americans “don't like ...
Oct 14, 2025 · JASON CALACANIS (HOST): I think this is because he's drifted from the 2.0 policies. Closing the border, very popular. Lower taxes, no taxes ...
[116]
Meet Gen-Xi - by jason@calacanis.com - JCal from All In - Substack
actually, both. And you learn ...
[117]
Extreme Capitalism with Jason Calacanis — REWORK - 37signals
Basecamp co-founder and CTO David Heinemeier Hansson sits down with entrepreneur and angel investor Jason Calacanis to debate the gig economy, democratic ...
[118]
Jobs Report & the Fed's Inflation Battle In the latest TWiST episode ...
The Fed's Ongoing Battle: Inflation remains stubborn, and the Federal Reserve is committed to keeping it under control, even as challenges persist. Jason's ...
[119]
The Real Reason Behind the Fed's Rate Cut Decision: Politics Over ...
Jun 17, 2025 · ... inflation, you're actually growing yourself out of this whole ... Jason Calacanis: The bottom half of H-1Bs are “a giant scam” and in ...
[120]
Trump Takes On the Fed, US-Intel Deal, Why Bankruptcies Are Up ...
Aug 29, 2025 · Chamath Palihapitiya, David Sacks, and Jason Calacanis debate the independence of the Federal Reserve, suggesting Fed governors are ...
[121]
Government Debt Crisis | Ask Dexa
Government Debt Crisis. David, Chamath, and Jason discuss the alarming levels of government debt and the potential consequences of over leveraging.<|separator|>
[122]
The American Dream is Broken: Real Wage Growth is the Key
Aug 17, 2025 · The American Dream is unattainable for many young people due to high debt, low wages, and unaffordable housing. J-Cal argues that real wage ...
[123]
Why Intel deal is a good deal for taxpayers | Jason Calacanis posted ...
Aug 25, 2025 · Here's why I say the Intel agreement is a good deal for taxpayers. A lot of Americans have raised their eyebrows at President Trump's plan ...
[124]
How His Startup Philosophy Shapes Southeast Asia's Ecosystem
Jun 1, 2025 · His contrarian views on government grants and regulatory approaches have sparked important conversations about sustainable startup development ...
[125]
It's not just Elon Musk. Other Trump tech allies are turning on his 'big ...
May 28, 2025 · In the episode, three of the four co-hosts leveled critiques against the bill. Co-host Jason Calacanis called the bill a failure of leadership ...
[126]
AI Regulation Debate | Ask This Week in Startups - Dexa.ai
Jason and Alexandr discuss the need for regulation in AI, particularly in light of the Cambridge Analytica scandal and its potential impact on elections.<|separator|>
[127]
https://substack.com/home/post/p-114783602
[128]
Jason Calacanis Says Amazon Will Replace All Factory Workers ...
Sep 15, 2025 · Calacanis said AI will soon double worker productivity every two years, leading to leaner teams. "You just need less lawyers at your company.
[129]
It's no shock that VCs are critiquing regulators, but when it comes to ...
Jul 5, 2024 · It's no shock that VCs are critiquing regulators, but when it comes to AI is the EU at risk of removing itself from the conversation?
[130]
Regulation-proofing your startup | Jason Calacanis posted on the ...
Spot on, Jason. Regulation is a moving target, especially in the gig economy. By reframing the model to empower LLCs and independent contractors, GoShare is ...
[131]
Inside.com's Jason Calacanis on the need for Big Tech regulation
Jul 9, 2021 · Jason Calacanis, Inside.com founder and CEO, joins "TechCheck" to discuss why lawmakers are looking to regulate Big Tech.Missing: views | Show results with:views
[132]
Politicians are worried Big Tech has too much power - YouTube
Jul 9, 2021 · Angel investor Jason Calacanis joins "TechCheck" to discuss why lawmakers are looking to regulate Big Tech.
[133]
Algorithm Transparency: Jason Calacanis Speaks Out - Instagram
Sep 24, 2025 · Jason Calacanis argues that social media companies should be transparent about their algorithms and allow users to choose their preferred ...
[134]
Regulatory Capture and Education | Ask All-In Podcast - Dexa.ai
David, Chamath, and Jason discuss the issue of regulatory capture in various industries, including drug development and hairdressing.
[135]
OK, WTF Is Up With the Government Bailing Out the Tech Industry?
Mar 13, 2023 · Calacanis then called for the U.S. government to bail out depositors in failed banks, mainly in the technology sector, a sentiment that was ...
[136]
Silicon Valley Bank Teaches Tech It Needs the Government After All
Mar 13, 2023 · The Silicon Valley Bank meltdown is teaching the tech industry that regulators are sometimes needed. The elites of the tech world, especially ...
[137]
U.S. executive order on AI data centers: What it means for the tech ...
Jul 29, 2025 · Jason Calacanis, accelerating ai infrastructure is crucial. balancing regulations and support could foster innovation without compromising ...
[138]
In conversation with President Trump - Apple Podcasts
Jun 20, 2024 · 06/20/2024 · 1HR 21MIN ...
[139]
Calacanis: 'I hate Trump' but small business loan program worked
Jul 7, 2020 · Angel investor Jason Calacanis told CNBC on Tuesday he hates President Trump, but praised the administration's small business loan program for saving many jobs.Missing: engagements | Show results with:engagements
[140]
E154: Presidential Candidate Dean Phillips in conversation with the ...
Nov 17, 2023 · (0:00) Bestie intros! (1:25) Democratic Presidential Candidate Dean Phillips shares his business background (13:11) Dean's time in Congress: ...Missing: engagements | Show results with:engagements
[141]
JD Vance | All-In Summit 2024 - YouTube
Sep 9, 2024 · (0:00) Besties intro JD Vance! (3:15) America's innovation problem (4:46) Thoughts on Trump (8:35) Would JD Vance have certified the ...
[142]
TWiST: Fake job postings and H-1B visa loophole | Jason Calacanis ...
Aug 27, 2025 · And I talked to JD Vice President JD Vance about this two or three weeks ago when I was in Washington, DC about hey. Are we actually using ...
[143]
JASON CALACANIS, AN INDIVIDUAL, ON BEHALF OF 20, L VS ...
On 11/12/2010 JASON CALACANIS, AN INDIVIDUAL, ON BEHALF OF 20, L filed a Property - Other Property Fraud lawsuit against INTERSERVE, INC DBA TECHCRUNCH, ...
[144]
At My Wit's End: Jason Calacanis Threatens To Sue Us | TechCrunch
Nov 3, 2010 · Jason Calacanis, our former partner on our TechCrunch50 events, is threatening to sue us. His demand letter and draft complaint are embedded below.
[145]
Jason Calacanis sues Mike Arrington over TechCrunch50 conference
Nov 15, 2010 · Arrington hinted in a post on his blog two weeks ago that Calacanis threatened to sue over ownership of TechCrunch 50, which was at one point a ...
[146]
In With A Bang, Out With A Whimper: Calacanis Walks ... - TechCrunch
Mar 2, 2011 · Just one business day after the conclusion of Jason Calacanis' Launch Conference he's filed a court document asking for the dismissal of the ...Missing: disputes | Show results with:disputes
[147]
Calacanis Waits To Be Sued -- But Angels Say They Won't Oblige
Oct 13, 2009 · Jason Calacanis stepped up his attack on angel groups that ... This Week In Startups.” “We're here to work together. Why can't we ...
[148]
Is Scott Galloway the Howard Stern of the Business World?
Aug 2, 2022 · The entrepreneur and investor Jason Calacanis, an early backer of Uber and Robinhood, has made Mr. Galloway a regular target of derision on ...
[149]
Why Does Jason Calacanis Hate Scott Galloway? - Maria Petrova ✏️
Mar 5, 2022 · Calacanis has tweeted attacking, bullying, and hateful tweets at Galloway hundreds of times. I counted 156 tweets, and those are just the ones ...
[150]
Scott Galloway on X: "The VC who has tweeted about me 300+ ...
Mar 6, 2022 · It's getting creepier, so I had to write this explainer about @jason's obsession with @profgalloway ...Missing: feud | Show results with:feud
[151]
Palmer Luckey and Jason Calacanis in X: War of Words
Nov 23, 2024 · Luckey has publicly accused Calacanis of being a bully, even admitting to keeping tabs on critics who played a role in shaping the narrative ...
[152]
The Fallout Between Palmer Luckey and Jason Calacanis - Palo Alto
Oct 8, 2024 · Calacanis was one of the most vocal critics, condemning Luckey's involvement and suggesting that it could harm the tech sector's image. Luckey ...
[153]
Jason Calacanis & David Sacks hash out their Twitter beef - YouTube
Oct 26, 2022 · Jason Calacanis & David Sacks hash out their Twitter beef. 15K views ... Jason Calacanis: Startups, Angel Investing, Capitalism, and ...
[154]
Jason Calacanis (the most successful Angel Investor of all time) just ...
Aug 28, 2019 · Jason Calacanis just publicly called out Neil Patel, Timothy, and Robert Herjavec for trying to swindle people with their newly announced ...
[155]
What you need to know about Elon's inner circle at Twitter - Vox
Nov 12, 2022 · Twitter's new CEO has sparked layoffs, trolled employees, and freaked out advertisers. Who is Musk getting his advice from?Missing: arguments | Show results with:arguments
[156]
The All-In Podcast's Hypocritical Shift: From "Besties" to GOP Echo ...
May 3, 2025 · The All-In Podcast sold itself as a forum for nuanced debate among “besties” with differing views. Now, it's a GOP echo chamber where dissent is drowned out.
[157]
What exactly is the source of friction between Jason Calacanis and ...
May 22, 2023 · The whole fiasco was over the anonymous propaganda 'revolution' Palmer was involved in. He posted to Reddit anonymously and funded anti-Hillary political ...Jason and Elon's texts about taking Twitter private : r/TheAllinPodcastsJCal went on the Bulwark podcast with Tim Miller : r/TheAllinPodcastsMore results from www.reddit.com
[158]
Angel - HarperCollins Publishers
In stock Free delivery over $35How to Invest in Technology Startups--Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000. By Jason Calacanis,. On Sale: July 18, 2017.
[159]
Angel by Jason Calacanis – Porchlight Book Company
In this enlightening guide that is sure to become the bible for twenty-first century investors, Calacanis takes potential angels step-by-step through his ...
[160]
Angel: How to Invest in Technology Startups-Timeless Advice from ...
In stock $6.99 next-day deliveryPublication date: 07/18/2017. Pages: 288. Product dimensions: 5.90(w) x 9.10(h) x 1.20(d). About the Author. Jason Calacanis is a technology entrepreneur, angel ...
[161]
https://www.audible.com/pd/Angel-Audiobook/B06ZXZ3B3W
[162]
'Angel: How to Invest in Technology Startups' (book review)
Jul 18, 2017 · Title: “Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000″
[163]
INSIDE - Curated Conversations
Curated conversations worth your time. Join curated groups where thoughtful contributors share insights on topics that matter.
[164]
Jason Calacanis on Startups | jason@calacanis.com | Substack
Jason, Lon, and Alex cover the latest in tech and startup news: Circle's IPO and Stablecoin Yield. Salesforce buys Informatica for $8B.Missing: articles | Show results with:articles
[165]
Jason Calacanis Net Worth & Popular Startup Investments - Capitaly
Another of Jason's notable investments is Robinhood, the commission-free stock trading app. ... Jason's bet on Thumbtack highlighted his belief in the ...
[166]
Jason Calacanis Talks About LAUNCH Conference
Mar 7, 2012 · Kara Swisher interviews longtime entrepreneur Jason Calacanis about his latest LAUNCH conference, in which he will give away $1 million to ...
[167]
Jason Calacanis is Raising a VC Fund to Back Startups from His ...
Jun 3, 2013 · The fund will focus “exclusively on folks who come out of LAUNCH Festival, LAUNCH Hackathon, LAUNCH Education & Kids and LAUNCH Mobile (our four ...
[168]
How Jason Calacanis turned a conference into a VC fund: Angel S6 ...
Jason shares his experiences with his first LAUNCH fund, the changes in his role as the fund scaled, and his journey as an angel investor. G.
[169]
Jason Calacanis - Age, Family, Bio | Famous Birthdays
In 2015, he moved from Los Angeles to San Francisco to focus on a start-up he founded called Launch. He married Jade Li in 2006. They have three children.
[170]
Weblogs Co-founder Jason Calacanis Has Invested in Over 200 ...
Oct 18, 2023 · His love story with Jade Li Calacanis began in the entrepreneurial world, and the couple married sometime between 2006 and 2009. Their family ...
[171]
The Daddy Daughter Podcast - Spotify
The Daddy Daughter Podcast is a show hosted by Jason Calacanis and his three daughters. 5 (6).
[172]
All In Podcast Hosts' Net Worth: Chamath, Jason, David & Sacks
Apr 10, 2025 · The All-In Podcast features four prominent figures in the tech and investment world: Chamath Palihapitiya, Jason Calacanis, David Sacks, and David Friedberg.
[173]
Jason Calacanis Net Worth
Jason Calacanis Net Worth: Jason Calacanis is an American entrepreneur, angel investor and author who has a net worth of $60 million dollars.
[174]
How a founder went from being worth millions to - Business Insider
Aug 3, 2017 · Jason Calacanis is worth more than $100 million, thanks largely to being a keen angel investor in startups like Uber.Missing: residence | Show results with:residence
[175]
All In Podcast Hosts' Net Worth: Chamath, Jason, David & Sacks
Apr 10, 2025 · The All-In Podcast features four prominent figures in the tech and investment world: Chamath Palihapitiya, Jason Calacanis, David Sacks, and ...
[176]
PODCAST: Jason Calacanis Speaks Plainly About How To Get Rich
Jul 4, 2017 · Calacanis shares what he has learned investing in over 150 companies at the angel phase and how he sees wealth creation is changing in his new ...
[177]
How Jason Calacanis Built His Fortune (And Why the All-In Podcast ...
Aug 13, 2025 · 1. Early Life and Humble Beginnings. Jason Calacanis was born in Brooklyn in 1970. He grew up in a working-class family where hustle was a ...