Why Does Jason Calacanis Hate Scott Galloway?
You’re not the first person to ask — this obsession is truly bizarre. Calacanis has tweeted attacking, bullying, and hateful tweets at Galloway hundreds of times. I counted 156 tweets, and those are just the ones where @profgalloway is tagged, which in my estimation is less than half. Just a few examples:
(Btw why am I writing this? I was a contractor for one of Professor Galloway’s companies from 2017–2020. It has been utterly bizarre to watch this obsession unfold, month after month, year after year.)
Why does a wealthy VC need to attack, unprovoked, a professor and entrepreneur? How many other grown men do you know who exhibit such immature behavior, and in public?
Here’s why: Galloway writes a weekly blog, No Mercy / No Malice. He is also a guest on TV networks, especially MSNBC & CNN. In his blog and appearances, Galloway often criticizes companies that Calacanis has a financial interest in — including Uber, Robinhood, and Calm. Galloway said the Uber board should fire Kalanick, that Uber’s valuation is insane, that ride-hailing companies exploit the unremarkable (same piece), and that Uber exhibits some of the disturbing aspects of big tech (also that piece). Calacanis said Galloway “destroyed Uber.”
Galloway wrote, “Calm is one of those companies that when the funding and cheap capital runs out, it’s not going to be so calm.” But he reserves his harshest criticism for Robinhood, whom he calls “mendacious fucks” on Pivot and in this post. The piece is a scorcher: “The company’s mission to ‘democratize finance for all,’ is similar to Pablo Escobar saying his mission was to ‘democratize cocaine.’” Galloway wrote that post in the aftermath of Alex Kearns, the young Robinhood user, committing suicide after the app misled him into thinking he had lost hundreds of thousands. Robinhood didn’t offer phone support at the time, unlike most other brokerages. It gamified trading and was pushing users into trading options, which most brokerages reserve for more experienced traders.
This is how the love-hate was born … In case you missed it, it includes a childish video that Calacanis created in an attempt to mock Galloway. Yes, a 51-year-old man did that. A venture capitalist with a huge audience. Calacanis also drew a cartoon giving Galloway a gut and himself freakishly large genitalia. How did Galloway respond? By challenging Calacanis to a charity match. Calacanis declined.
Everyone knows a bully is insecure. In college I wasn’t taught to make a funny video of my opponent to win an argument. If this were just teasing, it would be 10 tweets over 2 years, not 400. It’s troubling to see a barrage of mocking tweets over the years to an audience of half a million people, many of them young men eager to replicate that behavior. What kind of role model are you, to your children and the hundreds of thousands of men who follow you?
I’m an immigrant from Eastern Europe. As I have said several times to Calacanis, I’m aghast to come to the US and discover that some of the men who run Silicon Valley, the bedrock of American ingenuity, are tragically petty and embarrassingly small — in the face of wild privilege. This is America: a VC obsessively, childishly attacks the character of an academic who dares question the value of his portfolio companies. It’s completely bizarre to see this from a venture capitalist who is otherwise respected and widely influential.
Men in power behaving erratically is deeply destabilizing to the broader public. Trump made that clear. We need men in power to have their shit together. This week, it’s concerning to see a tweet like this from Calacanis. It’s troubling to know that powerful structures are run by people who are petty. To see schoolyard-bully behavior by men with tremendous influence. To know that decisions that impact hundreds of millions (Uber, Robinhood) are made by people with so little self-control. Dude, it’s embarrassing.