Jason McCabe Calacanis is an entrepreneur, angel investor, author and podcast host. A Fordham graduate, he built media businesses before becoming an early-stage technology investor. He co-founded Weblogs, Inc. with Brian Alvey; AOL acquired the company in 2005. He later developed the Mahalo search and education business.
His subsequent work includes the LAUNCH investment ecosystem, This Week in Startups and the All-In podcast. He wrote Angel, a book about early-stage technology investing, published in 2017. Autopilot’s Calacanis Tracker draws from published trading information and should be distinguished from his private startup investments.
One octagon for each phase of the life of Jason Calacanis. Each of the eight axes is scored 0 to 5 against a written rubric from documented evidence, with its source; an axis without evidence is a gap, not a zero. There is no total and no ideal shape: it is a profile, not a ranking. Appearance and personality are not axes, because they cannot be scored from evidence.
OverviewGenerated from documented data: the office held, income against IRS percentiles, the highest recorded degree and the reviewed legal record. Axes with no documented evidence are left out; researched phases are added through the wiki.Only 1 of the 8 axes have documented evidence, so no shape is drawn yet.
No total and no ideal shape: a longer spoke means more of that axis, so a long Misconduct spoke is more documented misconduct.
Scores, rubric and sources
01Education3 of 5
Medium confidenceHighest recorded degree: BA, Fordham University..[1]Highest attainment by then: 1 secondary school, 2 some college, 3 bachelor's degree, 4 master's or professional degree, 5 doctorate.
02WealthNo evidence
Net worth or income against the national thresholds of the time: 1 below the median household, 3 top 5%, 5 top 0.1%.
03PositionNo evidence
Scope of the role held: 1 entry level, 3 senior manager or legislator, 5 head of state or government, or the top role of a major institution.
04Public standingNo evidence
Public approval or favourability where it was measured: 1 under 20%, 3 35 to 50%, 5 over 65%.
05HealthNo evidence
Documented health where an examination or disclosure exists: 5 no documented concern, 1 a serious documented condition.
06MisconductNo evidence
The documented legal and ethics record within the phase, as in the misconduct meter: 0 none documented, 1 only matters resolved in their favour, 2 an open matter, 3 one finding, 4 two or three, 5 four or more. More is more documented misconduct.
07Social goodNo evidence
Assessed effects of what they did in the phase on health, safety, education, rights and the environment, from official statistics or peer-reviewed evidence: 0 clearly harmful, 2.5 mixed, 5 clearly beneficial.
08Economic goodNo evidence
Assessed effects of what they did in the phase on efficiency, growth and fiscal sustainability, from CBO and peer-reviewed evidence, as in the good-for-society reading: 0 clearly harmful, 2.5 mixed, 5 clearly beneficial.
Personal holdings & P&L
Latest published holdings, with their source dates. Positions may have changed. Transaction disclosures alone do not establish remaining shares or cost basis.
No verified personal portfolio snapshot is available. Personal holdings and unrealized P&L are unknown; associated fund or strategy holdings appear separately.
Personal trades & P&L
Publicly disclosed personal trading activity. Publication dates and trade dates are distinct; a commentary post is not a complete execution record.
Realized P&L requires matched acquisition costs and sale proceeds for the same security and quantity. Transaction value ranges, inferred quarterly changes and commentary do not establish profit. Missing cost or execution data remains undisclosed.
No verified personal trade ledger is available. Trading activity and realized P&L are unknown, not zero.
Fund holdings & tracked strategies
Latest published holdings, with their source dates. Positions may have changed. Transaction disclosures alone do not establish remaining shares or cost basis.
These are the tracked strategy’s holdings and client-strategy returns. They do not establish this person’s own positions or profit.
Calacanis Tracker · as of Oct 25, 2026
Security
Allocation
Unrealized P&L
AAPLApple Inc.
16.2%
Not disclosed
AMZNAmazon.Com Inc
14.6%
Not disclosed
HOODRobinhood Markets, Inc. Class A Common Stock
10.8%
Not disclosed
Only part of the portfolio is public · 15 additional holdings not published (58.4%)
Stock P&L requires a disclosed position cost basis and a dated valuation in the same currency. It is unrealized price P&L and excludes dividends and realized gains. Missing inputs stay undisclosed.
Work and contributions8
Work6
2017 — Angel[1]profile-research-2017-angelPublished Angel: How to Invest in Technology Startups, a book explaining early-stage investing through his experience.
All-In podcast[1]profile-research-all-in-podcastCo-hosts the business and technology podcast alongside David Sacks, Chamath Palihapitiya and David Friedberg.
Calacanis Tracker[2]autopilot-52938Autopilot lists this strategy as following public disclosures, public commentary or the associated investment firm. The named person does not thereby operate or endorse the tracker.
Career and background
Sources2
Biographical facts about Jason Calacanis are backed by the wiki and its numbered references. Holdings and trade disclosures cite their sources within their own sections. Read the wiki
Health, weight and religion appear only where the person, their physician or a reputable outlet has published them; each links to its source.
Published portfolio return
as of Oct 23, 2026 · Started Feb 16, 2023
Last month
-6.49%
Year to date
-0.58%
1 year
-1.97%
Since inception
+150.12%
Performance methodology
The performance data presented reflects the aggregated results of actual client portfolios managed by the Registered Investment Adviser (RIA), based on the trading activity in the securities contained in the relevant portfolio over the specified period. If fewer than 10 clients are invested in the portfolio, the data represents the aggregate performance of all clients following this strategy. Performance figures are shown net of advisory fees, calculated using the applicable subscription fee and an assumed $50,000 account size. Because subscription fees are flat rather than asset-based, accounts smaller than $50,000 would experience a higher effective fee percentage and lower net performance, while larger accounts would experience a lower effective fee percentage. Actual investor outcomes can vary due to factors like brokerage support for fractional shares, account size, trade timing, fees, and taxes, and past performance should not be interpreted as a guarantee of future results or typical of all portfolios.
Entrepreneur, angel investor, author and podcaster. He co-founded Weblogs, Inc. and hosts This Week in Startups and co-hosts the All-In podcast.
Professional profile and background[1]profile-research-biographyJason McCabe Calacanis is an entrepreneur, angel investor, author and podcast host. A Fordham graduate, he built media businesses before becoming an early-stage technology investor. He co-founded Weblogs, Inc. with Brian Alvey; AOL acquired the company in 2005. He later developed the Mahalo search and education business.
His subsequent work includes the LAUNCH investment ecosystem, This Week in Startups and the All-In podcast. He wrote Angel, a book about early-stage technology investing, published in 2017. Autopilot’s Calacanis Tracker draws from published trading information and should be distinguished from his private startup investments.
This Week in Startups and LAUNCH[1]profile-research-this-week-in-startups-and-launchDeveloped startup-focused media and investment programs linking founders with investors and entrepreneurial education.
Companies founded2
2007–2014 — Mahalo[1]profile-research-2007-2014-mahaloBuilt Mahalo as a human-assisted search business, later expanding into education-oriented content before its closure in 2014.
Weblogs, Inc. and AOL acquisition[1]profile-research-weblogs-inc-and-aol-acquisitionCo-founded the blog publisher with Brian Alvey and sold it to AOL in October 2005.
