Fundraising Fox

Jason Calacanis

Investor

Founder at LAUNCH · Board director at Formulate Labs · Board director at Fitbod · Board director at Gramercy Technologies

Austin, TX

Writes $100K – $500K checks

Photo: Preshdineshkumar, CC BY-SA 4.0, via Wikimedia Commons ↗

About

Jason Calacanis sold Weblogs Inc. to AOL, then became one of the best-known angel investors of his generation with early checks in Uber, Robinhood, and Calm. Through LAUNCH he runs accelerator programs, syndicates, and funds, and his podcast This Week in Startups has run since 2009. He wrote Angel, a how-to guide for new startup investors, and co-hosts the All-In podcast.

Contact· published on Jason's own website

Likely emails· guessed from name + firm domain, not firm-published

Invests in

AI & Machine LearningClimate TechCloud ComputingConsumerCrypto & Web3Data & InfrastructureDeep TechDeveloper ToolsE-commerceEdTechEnterprise SoftwareFintechFuture of WorkGamingGovTechHealthtechInsurTechIoTMedia & EntertainmentPropTechRoboticsSaaSSocial

Beyond investing

Founded
Calacanis co-founded the blog network Weblogs, Inc. with Brian Alvey in 2003, which was sold to AOL in 2005. In 2009 Calacanis founded the Open Angel Forum, an event connecting early-stage startups with angel investors.
Education
Studied at Fordham University (B.A., Psychology) Studied at Xaverian High School (1988)
Communities
Calacanis was an early supporter of and founder for the effort behind the 2022 recall of San Francisco District Attorney Chesa Boudin.
Awards
HarperCollins: Published Angel: How to Invest in Technology Startups.
Hobbies
Calacanis is an enthusiastic recreational poker player who has appeared as a guest on PokerStars The Big Game.
Family
Calacanis married Jade Li between 2006 and 2009 and has three children. Calacanis was born in Bay Ridge, Brooklyn, is of half-Greek and half-Irish descent, and has two brothers.
More
Calacanis co-hosts the All-In podcast with Chamath Palihapitiya, David Sacks, and David Friedberg. AOL: Acquired Weblogs, Inc. for a reported $25–30 million. This Week in Startups: Founder and host of one of the longest-running startup podcasts. Open Angel Forum: Founded a pitch event that refused to charge founders to present to investors. All-In Podcast: Co-host.

From Jason's own website — common ground for a warm intro.

Board director at Formulate Labs

Intro paths

In turn, Jason can intro founders to Formulate Labs's investors below.

Board director at Fitbod

Intro paths

In turn, Jason can intro founders to Fitbod's investors below.

Co-founders at Fitbod

JVJess Venticinque
Jess VenticinqueExecutive Officer, Director, Promoter
ACAllen Chen
Allen ChenExecutive Officer, Director, Promoter
JVJesse Venticinque
Jesse Venticinque

Board director at Gramercy Technologies

Intro paths

In turn, Jason can intro founders to Gramercy Technologies's investors below.

Experience

  1. All-In PodcastBestiecurrent2021 — presentSan Francisco Bay Area
  2. Founder UniversityTeachercurrent2021 — presentUnited States
  3. This Week in StartupsHostcurrent2009 — presentSan Francisco Bay Area
  4. ANGEL, the BookAuthorcurrent2017 — presentSan Francisco Bay Area
  5. UberAngel Investorcurrent2010 — present
  6. Inside.comCEO & Foundercurrent2007 — present
  7. LAUNCHFounder & CEOcurrent2011 — presentSan Francisco Bay Area
  8. Sequoia CapitalEntrepreneur in Action2006 — 2007
  9. Weblogs, Inc.CEO & Co-Founder2003 — 2006
  10. VentureReporter.netCEO1996 — 2003
  11. Silicon Alley ReporterFounder, CEO & Editor1996 — 2001

Skills & more

Public Speaking99Personal Development54Personal Branding84Leadership99Inspiration57Facebook43WordPress41Google Analytics41Web 2.042Marketing Strategy99Public Relations99Product Development99
+12 moreCapital RaisingCorporate BrandingLogo DesignUser Interface DesignOnline AdvertisingSocial Media MarketingSEOAngel InvestingMobile ApplicationsMobile DevicesE-commerceBlogging

From Jason's professional profile.

Deals · 9

Best in GrowBoard seat

via LAUNCH · filed Dec 2022 · $8M raise

Grin TechnologiesBoard seat

via LAUNCH · filed Oct 2021 · $113M raise

press ↗

ContiqBoard seat

via LAUNCH · filed Oct 2020 · $21K raise

Formulate LabsBoard seat

via LAUNCH · filed Oct 2020 · $2.5M raise

FitbodBoard seat

via LAUNCH · filed Mar 2020 · $4.7M raise

TakeoffsBoard seat

via LAUNCH · filed Jul 2019 · $3M raise

Gramercy TechnologiesBoard seat

via LAUNCH · filed Oct 2018 · $3.5M raise

Cafe X TechnologiesBoard seat

via LAUNCH · filed Aug 2018 · $12M raise

BlokableBoard seat

via LAUNCH · filed Nov 2017 · $6M raise

Attribution from SEC filings, press coverage, and firm rosters.

Other disclosed investments

Investor

8090CalmCalm.comDataStaxDensityDesktop MetalGrin.coRobinhoodSuperhumanThumbtackTrelloUberWealthfront

Sources: SEC Form D filings · curated public sources.

Public positions

He treats access as the problem worth solving — for founders who have no network, and for investors who are not institutions. Open Angel Forum, the book, the syndicate and Founder University are all versions of the same argument: the gate should be traction, not who you know. The counterweight is that his own influence is now large enough that his commentary moves the ecosystem, which is what made his SVB posts so contested.

  • 2023 · Banking / SVB

    During the collapse of Silicon Valley Bank he posted a series of escalating all-caps warnings, telling founders they should be terrified and predicting that a thousand-plus startups were about to implode.

    The most consequential and most criticised public intervention of his career.

  • 2023 · Banking / SVB

    After the federal backstop was announced he said he had rung the fire alarm and that his work was done.

    The victory lap became the focal point of the criticism.

  • 2017 · Angel investing

    In Angel he argues ordinary accredited investors can learn to do this, that early-stage returns follow a power law, and that being useful to founders is the actual edge.

    His most complete written statement of method.

  • 2009 · Ecosystem

    He argued publicly that charging founders to pitch investors was extractive, and founded Open Angel Forum as the alternative.

    An early, concrete stance on founder-side power.

  • 2011 · Platform risk

    After Google's Panda update destroyed Mahalo's traffic, he has consistently warned founders against building on demand they do not own.

    A lesson drawn from his own failure rather than someone else's.

  • 2026 · AI investing

    LAUNCH's stated AI screen prioritises founders with direct experience of the workflow they are automating over general technical prestige.

    Concrete guidance on how to open an AI pitch with him.

Prediction record

Uber was the call of a career, and his 2017 bet that angel investing would broaden beyond a professional class was right — helped along by his own syndicate. Mahalo was a clear miss. His March 2023 warnings about SVB contagion were pre-empted by the federal backstop, so the underlying claim was never tested; what is testable is the criticism that broadcasting panic during a bank run made it worse.

  • Uber's model would work at scale — backed with roughly a $25,000 angel cheque

    Correct

    2009 · Decade

    The position was reported to be worth on the order of $100 million by the time Uber went public.

    Valuations of the stake are press estimates, not disclosed figures.

    angelinvestboston.comen.wikipedia.org

  • Human-curated search could compete with algorithmic search

    Missed

    2007 · Years

    Mahalo reached profitability in 2011, was hit by Google's Panda update, and shut down in 2014.

    He has since used it as his standard cautionary example about platform dependence.

    en.wikipedia.orgen.wikipedia.org

  • Without intervention, contagion from SVB would take down a thousand or more startups

    Open

    2023 · Days

    Regulators backstopped all deposits within days, so the counterfactual was never run.

    Critics argue the warnings themselves helped accelerate the run.

    newsweek.comedition.cnn.com

  • Angel investing would broaden well beyond a small professional class

    Correct

    2017 · Decade

    Syndicates, rolling funds and platforms — including his own 10,000-plus backer syndicate — became a standard part of early-stage financing.

    He is a direct beneficiary of the trend he predicted.

    en.wikipedia.orgvcsheet.com

Controversies & responses

Where Jason has drawn public criticism — with what happened, their response, and the criticism itself, side by side.

His role in the Silicon Valley Bank run2023
What happened
Over the weekend of SVB's failure he posted escalating all-caps warnings on social media urging founders to be terrified and predicting mass startup failures, then declared victory once regulators backstopped deposits.
The response
He framed the posts as ringing a fire alarm on behalf of founders whose payroll was at risk, and said the outcome vindicated the warning.
The criticism
Commentators argued that a highly followed investor broadcasting panic during a bank run made the run worse, and that the subsequent victory lap sat badly with calls for a public backstop of private deposits.
Where it stands
Contested; the episode is now a standard case study in social-media-driven bank runs.
Mahalo and content-farm criticism2007
What happened
Mahalo raised roughly $20 million for a human-curated search directory. Critics grouped it with content farms optimising for search traffic, and Google's Panda update — aimed at exactly that category — removed most of its distribution.
The response
He has been openly retrospective about it, using the collapse as his standing argument against building on platform-dependent demand.
The criticism
The company was cited as an example of arbitraging search rankings rather than creating durable value.
Where it stands
Closed in 2014; he discusses it openly.
Investor as media figure2020
What happened
He runs a fund whose deal flow depends on shows he hosts, and appears on All-In alongside investors with overlapping positions.
The response
He is explicit that the media and the fund are one system rather than separate businesses.
The criticism
Critics note the difficulty of separating commentary from book-talking when the commentator is also an early-stage investor.
Where it stands
Ongoing and openly acknowledged by him.

Books by Jason Calacanis

Podcasts & interviews

featuring Jason Calacanis

Jason Calacanis has built a front-row seat to the future of technology

SiliconANGLE theCUBE

All In Podcast Host Jason Calacanis Overviews Liquidity Summit in Napa Valley

New York Stock Exchange

Inside All-In: Investing Lessons from Elon, Trump, Travis K | Jason Calacanis

The Peel with Turner Novak

What Does This Mean for America - Jason Calacanis

Triggernometry

Jason Calacanis Tells the Origin Story of The All-In Podcast | The Tim Ferriss Show

Tim Ferriss

Jason Calacanis: Startups, Angel Investing, Capitalism, and Friendship | Lex Fridman Podcast #161

Lex Fridman

4 more appearances

Frequently asked questions

Who is Jason Calacanis?
Jason Calacanis sold Weblogs Inc. to AOL, then became one of the best-known angel investors of his generation with early checks in Uber, Robinhood, and Calm. Through LAUNCH he runs accelerator programs, syndicates, and funds, and his podcast This Week in Startups has run since 2009. He wrote Angel, a how-to guide for new startup investors, and co-hosts the All-In podcast.
Where does Jason Calacanis work?
Jason Calacanis is Founder at LAUNCH and Board director at Formulate Labs and Board director at Fitbod and Board director at Gramercy Technologies.
What does Jason Calacanis invest in?
Jason Calacanis invests in AI & Machine Learning, Climate Tech, Cloud Computing, Consumer, Crypto & Web3, Data & Infrastructure, Deep Tech, Developer Tools, E-commerce, EdTech, Enterprise Software, Fintech, Future of Work, Gaming, GovTech, Healthtech, InsurTech, IoT, Media & Entertainment, PropTech, Robotics, SaaS, Social.
What check size does Jason Calacanis write?
Jason Calacanis typically writes checks of $100K – $500K.
What boards does Jason Calacanis sit on?
Jason Calacanis holds tracked board seats at Best in Grow, Blokable, Cafe X Technologies, Contiq, Fitbod, Formulate Labs, Gramercy Technologies, Grin Technologies, Takeoffs.
What companies has Jason Calacanis invested in?
Investments tracked here include 8090, Calm, Calm.com, DataStax, Density, Desktop Metal, Grin.co, Robinhood, Superhuman, Thumbtack, Trello, Uber, and 1 more.
What awards has Jason Calacanis received?
HarperCollins: Published Angel: How to Invest in Technology Startups.
What podcasts and interviews feature Jason Calacanis?
Tracked appearances include "Jason Calacanis has built a front-row seat to the future of technology", "All In Podcast Host Jason Calacanis Overviews Liquidity Summit in Napa Valley", "Inside All-In: Investing Lessons from Elon, Trump, Travis K | Jason Calacanis", and 7 more.

Paths to reach Jason

People who overlapped with Jason at the same organization — a shared school or employer with one of them is a warm way in.

Together at Sequoia CapitalJason: Entrepreneur in Action

Together at LAUNCHJason: Founder

Together at UberJason: Angel Investor

Together at Founder UniversityJason: Teacher

Shared employers