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Jason Calacanis

Jason Calacanis77 posts

Jason Calacanis is an American blogger, publisher, and web entrepreneur, born in Brooklyn in 1970. He created the Silicon Alley Reporter industry newsletter and magazine. He set up the Digital Coast Reporter, a sister publication, and organized conferences in LA, New York, and San Francisco. He later created Weblogs, Inc., which was sold to AOL. He was managing editor of Netscape at AOL, and later joined the venture firm Sequoia Capital. He created Mahalo.com, a search engine, and the Open Angel Forum aimed at connecting startups and angel investors. He hosts the podcast This Week In Startups.


How To Make Millions interview


Calacanis tells HowStuffWorks about how Weblogs grew and developed:

We had all these passionate people blogging about these specific topics that advertisers could then advertise against, so you had this perfect marriage of bloggers who were passionate, an audience who was passionate about reading the bloggers, unfiltered, and advertisers, who could join that whole love-fest

17 Oct, 2014

TWiST – Tinder etiquette

Calacanis, Sarver, and Hoover talk on This Week In Startups about etiquette on the dating app. Calacanis:

Are you on the Tinder with all those other kids?


I had my first Tinder date, like, a month ago


You really went on a Tinder date. What’s that like?


It was normal. She was fine.

11 Oct, 2014

Starts LAUNCH incubator

Calacanis announces that he will be hosting a startup incubator that starts Dec 1. and ends at the LAUNCH Festival on March 2. The program will consist of six startups initially. Two slots have already been filled, by Weblogs, Inc. co-founder Brian Alvey and former LAUNCH CEO Jason Demant, leaving four spaces open:

The Incubator” is going to follow the basic Y Combinator model of 12 weeks and 12 dinners with speakers, but with a few twists.

11 Sep, 2014

Starts Launch Ticker

Calacanis starts the news service with $50,000 as he says he is tired of reading padded quotes and clickbait headlines. Initially he hires a college student to pull the most interesting stories from tech media and put them into a spreadsheet each day. To assistant:

Why the f-ck did you put something not important in my presidential daily brief? ‘Expedia Hires a New VP of Nothing’ — I don’t need to know this. Go find me something important.

Once the formula was perfected, he then started sharing the Google Doc with people in the tech industry, then created the app. Subscription costs $100 a year. He says TechCrunch is a joke since it lost Arrington and other senior people:

TechCrunch is the publication of record, but they’re so bad and uninformed. It’s insult after insult. When I play poker with other VC’s, we all laugh at TechCrunch.

Business Insider has one good story for every 10 stories, while other tech media are dominated by aggressive PR tactics. Launch Ticker isn’t profitable yet but he is already working on a Pro service that costs 10 times as much, and a generalized consumer-facing service, Inside. Calacanis on his media vs others:

You’re talking to LeBron James about guys playing in the rec league. These guys are amateurs, I’m the f-cking real deal.

15 Jul, 2014

TWiST retail at LAUNCH Beacon

Calacanis sits down with Ryan Craver of Lord & Taylor to talk about how consumers shop:

Are you brick or are you click?

Craver predicts how technology will enhance our purchasing power and rock the in-store experience.

3 Jul, 2014

This Week In Startups interview


Hoover and Calacanis talk about new products on Product Hunt like the Uber Wedding app and Soundcloud for iOS, how he got the idea for the site, and how viewers can interact with the people who create the products.

There’s some very interesting conversations that come out of Product Hunt.

He says that for an app called InstaNerd, site users contributed ideas and the founder incorporated them to improve the product.

Says Cutts killed Mahalo

Calacanis posts on the site about how he says Cutts killed Mahalo.com with the Panda formula:

[Cutts] just smiled and told me “you don’t have a penalty” with a shit-eating grin…. they targeted us for destruction and i had to layoff 80 americans working from home full-time. Salt of the earth people…. people making $500-700 a week… while the people at Google are spending $200 a week on gourmet food.

I’ve still got that Google kicking our ass fire in my belly. I want to come back from them jumping me in the parking lot and have my revenge.

9 May, 2014

Interview with Gavin Newsom

Calacanis sits down with the San Francisco Lt. Governor to talk about how startups can help with urban problems, and Newsom’s vision for the city, asking him tough questions:

How San Francisco is developing and growing int o a city of the future

Is it turning into Manhattan?

What will it look like in 10 years?

22 Apr, 2014

State Of The Media speech

Calacanis delivers his annual address about what he thinks of the state of new and old media:

I’m going to go very fast, and I’m going to talk about every single type of media

11 Mar, 2014

Launch Festival interview


Graham is interviewed by Calacanis at Launch Festival 2014, and talks about his decision to hand over the running of the accelerator to Sam Altman.

Y Combinator’s gonna have to grow. We grow as the number of startups grows and the number of startups has been growing. You saw how it started up – it was in my kitchen. Now it’s got 10 full-time partners…maybe 20 people. 632 startups we funded. It’s turned into this giant thing.  I’m no good at running this giant thing. Sam, however, is going to be good at running a giant thing.

4 Mar, 2014

Launch Festival interview


Calcanis and Kalanick have their first interview in four years, talking about Uber’s expansion plans, and a new feature of a push notification to let customers know when surge pricing periods are about to end. Kalanick says Uber now provides more than half the total rides in San Francisco, although he doesn’t give specific numbers. Kalanick talks about being an entrepreneur:

You’re afraid of failure, you do the best you can, but you really need to have the perseverance, the stamina, the hard core, to just make it through

5 Feb, 2014

Phat Startup interview

Calacanis talks about his come-up in the tech media world, diversification, and why you should always focus on your product, as well as loving your haters, why people in San Francisco are lying when they say it’s not about the money, how to market using free platforms, why you should always come out swinging, and how hip hop is all the inspiration he ever needed:


27 Jan, 2014


jason-calacanis-inside-com-logoCalacanis launches the mobile app, which highlights and summarizes news stories. The app is related to Mahalo.com. He hires Snyder, a former Atlantic editor, to run the service. It allows users to read a summarized version of the news or swipe through to read the full article. The news selection is curated by an editorial team. Snyder:

The idea behind it is that the world is heading to mobile, but there still isn’t a solution in the new space. I feel like the transition, in terms of news and mobile, is sort of where news and the web was in 2002. Everyone knew the web was going to be huge, but there still wasn’t a grammar to the form. [Inside.com aims to] marry what humans are good at and what technology is good at.

6 Jan, 2014

Intruders TV interview

Calacanis talks about how Peter Rojas pioneered live-blogging at Engadget, and says Mahalo is effectively applying the technique to the rest of the world:

22 Dec, 2013

Investment case for AngelList

Calacanis talks about the investment case for Naval Ravikant’s angel investment fund, and the future of investing in general:

Dec 2013

Interview with MBA student

Calacanis accepts an interview request from an MBA student, and talks about why he accepted the request:

Somebody emailed me out of the blue and said, Listen, I’m a fan of the show, I’m an entrepreneur, I’ve got an assignment, can I interview you? And I said of course…Because when I was a nobody coming up in the world, I sent those emails out, I hussled, and I got no responses…but then I got one or two responses…I’ve gotta make time for other people

5 Dec, 2013

15Five interview

Calacanis and 15Five CEO David Hassell talk about how company culture impacts hiring and retention:

26 Nov, 2013

PandoMonthly Fireside Chat

Calacanis talks with Sarah Lacy about how poker strategy is like entrepreneurship, various pieces of advice for entrepreneurs, and how family relationships like his strained relations with his father can affect people’s careers:

You show me a great entrepreneur and I’ll show you a f-cked-up relationship with one of their parents

22 Nov, 2013

Investment strategy

Sarah Lacy talks with Calacanis about how he managed to succeed as an acquired taste despite being fairly abrasive, and his investment strategy going forward:

Advice for Microsoft

Calacanis talks about how Yammer founder David Sacks could be Microsoft’s Marissa Mayer:

Dark career moments

Calacanis talks with Lacy about how his career has been driven by his father’s failed efforts at entrepreneurship as a bar and restaurant owner and how he has felt the need to prove something to his parents:

I think I was also proving it to myself

21 Nov, 2013

The meaning of being an entrepreneur

Calacanis talks about how tech companies should create real value for hackathons by offering genuine startup capital or, alternatively for established companies like Google, offering a stake in the companies themselves, to motivate founders. He also talks about why Larry Page keeps working despite having a net worth in the tens of billions, saying that he himself doesn’t need to work after ‘getting lucky’ with several projects, saying that people like Page and himself keep working because they want to build a legacy, or create something:

I love building teams, I love building products, I love building brands themselves…I love the act of creating a brand and doing something innovative

21 Oct, 2013

AccelerateOTT Fireside Chat

Calacanis and Social+Capital Partnerships founder Palihapitiya talk about Palihapitiya’s professional experiences, the lessons they have taught him and his views of the present startup environment.

When things aren’t working…when you’re forced to [work around difficulties] then you’re actually forced to try to be good at something

9 Aug, 2013

NextShark interview


Calacanis talks about building Weblogs Inc., how a blog network isn’t as easily scaleable now as it was before, and the problems he sees with YouTube. He says for artists, YouTube is possibly the best way to spread their work except for Pinterest which may be better for fashion designers, and Twitter may be better for comedians, but starting a standalone business on YouTube is problematic:

[..] there are certain things that make it really untenable to production companies and make it really impossible for it to be anything more than the third of the mix; anything more than a marketing tool with a little bit of revenue.
8 Aug, 2013

Making Youtube sustainable

Calacanis proposes a new deal for content creators to make it more sustainable, and owning your own audience, based on his companies’ experience publishing on YouTube and getting paid for it, and turning down funding from YouTube.

We’re going to hear about some of the good things about YouTube…The awesomeness, YouTube at its absolute best, people starting from nowhere, creating huge movements getting huge audiences and then doing interesting things with them

5 Jun, 2013

Talks about Tumblr acquisition

Calacanis explains the numbers behind Yahoo’s acquisition:

It turns out, there’s a lot of money in the world. The money is bored. Money wants to be spent! Money is intended to be gambled. These are big numbers, but these are big companies.

3 Jun, 2013

Raises $10 million fund


Investors in the fund include Yammer co-founder David Sacks, and another limited partner who isn’t identified at the time of the announcement. Calacanis in an email describes the fund’s focus:

[..] exclusively on folks who come out of LAUNCH Festival, LAUNCH Hackathon, LAUNCH Education & Kids and LAUNCH Mobile (our four events).

It plans to invest $25,000 to $100,000 in five to 10 startups a year.

1 May, 2013

Wants to run Twitter, YouTube, and more

For the Pando Daily CEO Supper Club, Calacanis talks to Sarah Lacy about the tech companies he wants to run:

Twitter I think is going to be more valuable than Facebook… I think [Facebook] is a very faddy trend.

He says the filling out the social graph offers no rewards, and is useless.

12 Mar, 2013

LaunchConference interview

Calacanis is interviewed at the start of the conference and talks about his new venture:

I only know about 30% of what I’m doing, but it will be somewhere in the news and information space

8 Feb, 2013

Dyn interview

Calacanis and Dyn CEO Hitchcock talk about the Launch Conference, and a contest Dyn is throwing to send a New England startup to the event.

14 May, 2012

Talks about reinventing Mahalo.com

Calacanis talks about how his human-powered search engine had to change its focus, after Google introduced the Panda software that prevented content-building sites from becoming influential. The company had to close down, try to wait out the changes, or reinvent its business. He chose to shift the company from a search-powered company into a content-powered one, and build in a process to review the quality of the content before publishing, via internal debate:

Most teams fail not because of fighting, but because of a desire to keep the peace

18 Jan, 2012

Talks about Amazon’s dominance

Calacanis talks with O’Reilly Media about his thoughts on Amazon’s dominance of the online retailing space and the tactics Bezos and co. use at the company, and how he thinks this is a good thing:

28 Feb, 2011

Silicon Valley Uncovered video

Calacanis talks to TheNextWeb about why Silicon Valley companies need a launchpad in the form of an accelerator:

We’re bringing together critical mass

Feb 2011

Starts Launch

Calacanis creates the startup editorial venture partly as a rival to TechCrunch and increase depth, knowledge and thoroughness in startup reporting. Initially it will be an email subscription service:

If you get people to commit to an email relationship, it’s the deepest most intimate relationship you can have online. Much deeper than Facebook and certainly more intimate than a blog. I want high-quality insider information, a celebration of entrepreneurship and taking risk. I want it serious and insightful rather than salacious and link-baity.

19 Feb, 2011

Startup Grind interview

Calacanis is interviewed at the startup event and talks about starting Silicon Alley Reporter, Weblogs, and his other ventures. His job summary online says he has gone from ‘nobody’ to media titan and back several times, with a question mark over the future:

Never take yourself too seriously

3 Nov, 2010

FOWA London interview

Calacanis talks at the Future Of Web Apps event about his experience with Silicon Alley Reporter, Netscape, Sequoia, and others, saying that he had many great experiences but also difficulties along the way:

That’s how I became a great CEO, thanks to all the hardships

Responds to threat of legal action

Arrington responds to an alleged threat of legal action by Calacanis over the proceeds of the TechCrunch Disrupt sale to AOL. He says that the event – when it was known as TechCrunch 50 – had productive years in 2007 and 2008 when it was first competing with the paid events like Demo but that it became apparent Calacanis wasn’t putting in as much as TechCrunch despite the 50-50 profit split. He also wasn’t approving some expenses, forcing TechCrunch to either sue him or take the hit – it chose the second option. Reportedly Calacanis became abusive on a phone call and made a TechCrunch employee cry. Arrington:

And his most shining moment – he got so drunk the night before the last day of the 2008 conference that he couldn’t show up to be on stage until hours after the event started.

Arrington says he still considers Calacanis a friend but that all efforts to work with him – including offering 10% of TechCrunch and a board seat – have failed.

15 Oct, 2010

Talks about European and Nordic startups

Calacanis says European and Nordic startups are currently held back by legislation and lack support from their governments, and that they need to become more hardworking and take more risks:

27 Aug, 2010

Warns startups about Facebook

Calacanis issues a warning for Y Combinator companies:

If you tell Facebook about your startup before you reach critical mass, if you become involved with Facebook in any way, you are an idiot. They will steal your company’s ideas, and try to get you to take a small price for your company, and take a job at Facebook, which by they way, is going to be a job that sucks.

13 Jul, 2010

Old Spice guy response

The Old Spice guy responds to Calacanis’s question, How can I get over my aces being cracked at World Series of Poker?

12 May, 2010

Carpool interview

Llewellyn, formerly of Red Dwarf, Scrapheap Challenge, and Fully Charged, interviews Calacanis while giving him a lift to work. Calacanis about why he lives in San Francisco:

I fell in love with the city, and fell in love with the women. That’s about the only reason anyone would leave New York, the greatest city in the world – for a woman.

12 Apr, 2010

Jihad against pay-to-demonstrate

Calacanis talks with Mary Kathleen Flynn of The Deal about how Open Angel solves the problem of paying to demonstrate:

Pretty simply we’re destroying the other events…those people I’m on a jihad against, I’m destroying them

He says charging $5,000 to demonstrate is a scam and that people who charge are preying on the desperateness of entrepreneurs.

3 Feb, 2010

Offers Tesla Model S

Calacanis talks about his offer to give one of the first Model S’s to someone who can get his handle, @Auto, to the top user spot on Twitter, in a stunt to raise publicity about Mahalo:

I am a huge fan of electric cars, I am a huge opponent of our Middle East policy…Tesla are the only company with an electric car on the road in production

2 Jan, 2010

Launches ThisWeekIn

Calacanis and Pollak create the streaming video network, closing a $300,000 angel funding round from Calacanis, Sky Dayton, founder of Earthlink and Boingo, and Matt Coffin, founder of LowerMyBills.com, and tapping former Mahalo.com CTO Mark Jeffrey to run the network as co-founder and CEO. Calacanis:

The production of high-quality, live-streaming, video content has finally arrived. In the same way blogs grew from passion projects in 2005 to thriving businesses in 2009, streaming shows are poised to breakout


Starts angel investing

Calacanis says in an email announcing the Open Angel Forum – designed to connect startups with investors like Elon Musk and Mark Cuban – that he has also started angel investing himself:

My first two investments are www.gdgt.com and www.challengepost.com. I’ll be announcing two more angel investments in December. My goal is to do 5-10 a year.

What's this? This is an unbiased just-the-facts news timeline ('newsline') about Jason Calacanis, created by Newslines contributors. Make it grow it by finding and summarising news. Learn more