A ‘bulldog’ who ‘cuts through the bulls—‘: Here’s how insiders describe early Robinhood investor Jason Calacanis

Jason Calacanis
Jason Calacanis

Jason Calacanis has had several incarnations during his more than two decades in tech, making waves as a publisher, a blogger and an entrepreneur.

Today, he’s living his latest, and seemingly most successful, life as a startup investor. 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 startups founders make it to the big leagues.

And, almost every day, he’s preaching his philosophy and broadcasting his opinions through various podcasts and newsletters.

If there’s one thing the peers, portfolio company founders, friends and frenemies of Calacanis all agree on, it’s his default setting as a polarizing lightning rod. People close to Calacanis describe him as impulsive, brilliant, opinionated, and brash – sometimes all in the same conversation.

Calacanis doesn’t disagree. “Most folks think I’m lucky, some say I’m a complete fraud, and a handful think I’m a brilliant hype man, and I don’t agree with any of them – I agree with all of them,” he wrote in his 2017 book, “Angel: How to Invest in Technology Startups.”

To chart Calacanis’s rise up Silicon Valley’s clubby investor ranks, Insider spoke with more than 50 people close to him for the most in-depth profile of the investor to date.

Here are a few excerpts from those conversations that show just how polarizing of a figure Calacanis has become in Silicon Valley’s venture capital and startup scene.

  • “There is nobody out there that has not gone to war with Jason at some point. But the funny thing is, then, a year later, they are back on his podcast or back asking him for a job.” Brian Alvey, a former business partner and childhood friend.
  • “Would I want him on my side? Absolutely. He’s a bulldog.” – Launch alum Jeremy Redman
  • “He’s the type of person who will give you blunt feedback and advice. It’s going to hurt – a lot.” – Launch alum Sheri Atwood
  • “He cuts through the bull– and gets right to the point. It was not like he needed to see a business plan, projections, all the paperwork.”Christy Liu, cofounder of Wanderfly, a travel recommendation startup that was acquired by TripAdvisor.
  • “He’s kind of earned the right” to make bold claims on Twitter and “his track record speaks for itself.” – Launch alum George Charkviani

You can read the full story here if you’re an Insider subscriber.

Read the original article on Business Insider

Twitter dips its toes in the pay-to-play waters

Hello, and welcome to this week’s edition of the Insider Tech newsletter, where we break down the biggest news in tech, including:

Did someone forward this newsletter to you? Sign up here.

Soundtrack: This week’s newsletter has been specially designed to be consumed while listening to The Toasters’ “Weekend in LA”


This week: Twitter dips its toes in the pay-to-play waters

Jack Dorsey

Perhaps you’ve noticed the expanding number of charges for video streaming subscriptions on your credit card statement. What started with a Netflix subscription has become monthly payments for a half dozen or more video services, from Apple+ and Disney+ to HBOMax and Peacock Premium.

Could the same pay-to-play fate await our social media and communications apps?

Twitter will never get rid of the free version of its product – but there’s precedent for a premium Twitter. Back in 2010 there was a thriving market of third-party Twitter “client” apps that connected to Twitter’s API and offered power users extra options. Many of these client apps cost a few bucks to download, and charged additional a la carte fees for extra features.

But: Twitter kneecapped the third-party clients market starting in 2011 by restricting access ot its API – a controversial move that was necessary for Twitter to keep people on its own site so it could build an ad business. Now, ten years later, ads aren’t enough, and Twitter is turning to a business model it once squashed.

In other social media news:

Trump is banned from Twitter forever. But he could be back on Facebook in less than two years, if he behaves and “conditions permit.”


Profile: Angel investor Jason Calacanis

Jason Calacanis

He’s loud, brash, confident, and has a string of prescient startup investments under his belt, including early bets on Uber, Robinhood and Calm. Jason Calacanis is part venture capital investor and part podcasting shock jock – and he’s a polarizing presence in Silicon Valley.

As Matt Drange and Candy Cheng report in this fascinating profile:

For many, Calacanis is someone who “cuts through the bulls—” and is shaking up Silicon Valley’s stuffy venture-capital scene. But others said the swagger can quickly turn hostile, with some founders describing experiences with Calacanis that left them questioning whether he was more committed to their success or to his own image.

Read the full story here:

Jason Calacanis went from dotcom roadkill to early investor in Uber, Calm and Robinhood. Here’s how he’s reshaping venture capital with bluster, ego, and media-savvy.


Quote of the week:

Tim Cook

“Video conference calling has narrowed the distance between us, to be sure, but there are things it simply cannot replicate.”

– Apple CEO Tim Cook, in a letter to staff obtained by The Verge, breaking the news to employees that they’ll be expected in the office at least three days a week, come September.


Snapshot: Behold the clouds of Mars

Even Mars has cloudy days. And thanks to NASA’s Curiosity rover, we can now see what it’s like to gaze up at a Martian cloud.

mars clouds above cliff photo curiosity rover
NASA’s Curiosity Mars rover captured these clouds just after sunset on March 19, 2021. The image is made up of 21 individual images stitched together and color corrected so that the scene appears as it would to the human eye.

The photo above, captured at sunset on the red planet on March 19, is one of several rare photos of Martian clouds recently released by the space agency. Mars doesn’t get too many clouds because of its dry atmosphere and super thin air. But clouds do form around the Martian equator at a certain time of year, and Curiosity had its cameras ready for otherworldly weather this season.

Many of the clouds caught on camera by Curiosity had an iridescent, pearl-like color. That’s because clouds on mars are made of frozen carbon dioxide, or dry ice, rather than water ice. Let’s hope it doesn’t rain.


Recommended readings:

Insiders say Oracle’s best hope in the cloud wars with Amazon is a team led with a ‘culture of fear,’ and executives are leaving

Google is making a privacy change on Android that could mean more pain for advertisers

Americans are embracing paying for everything online in installments. That’s propelling one startup, Klarna, to a valuation above $40 billion.

After Amazon’s MGM deal, experts think these 5 Hollywood giants could be Big Tech acquisition targets

People are finding out that buzzy photo-sharing app Poparazzi automatically follows all of their phone contacts, and experts say it’s a data privacy nightmare

The way to stop companies from getting attacked by ransomware is simple: outlaw ransom payments


Not necessarily in tech:

How ‘Tiger Mom’ Amy Chua became the pariah of Yale Law. A complicated story of booze, misbehaving men, and the Supreme Court.


Thanks for reading, and if you like this newsletter, tell your friends and colleagues they can sign up here to receive it.

– Alexei

Read the original article on Business Insider