• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
LeadershipElon Musk

Early Twitter investor and Musk pal warns the billionaire is surrounded by ‘yes men’ and is ‘stoking insanity’

Sophie Mellor
By
Sophie Mellor
Sophie Mellor
Down Arrow Button Icon
Sophie Mellor
By
Sophie Mellor
Sophie Mellor
Down Arrow Button Icon
November 8, 2022, 7:51 AM ET
Chris Sacca, founder of Lowercase Capital and an early investor in Twitter, Uber, and Instagram.
Chris Sacca, founder of Lowercase Capital and an early investor in Twitter, Uber, and Instagram.David Paul Morris—Bloomberg/Getty Images

One of the inevitable troubles of being a person with immense wealth and power is that you often find yourself surrounded by people who won’t call you out on a bad idea.

Venture capitalist and early Twitter investor Chris Sacca warned Elon Musk that he is completely alone and is surrounding himself with people who won’t challenge his nonconformist ideas to transform Twitter into his vision of a free-speech social media haven.

“One of the biggest risks of wealth/power is no longer having anyone around you who can push back, give candid feedback, suggest alternatives, or just simply let you know you’re wrong,” Sacca, founder of Lowercase Capital and a friend of Elon Musk, wrote in a Twitter thread on Monday evening.

https://twitter.com/sacca/status/1589732881232203776

Musk needs people around him who are willing to “speak some truth to power and complement his bold and ambitious instincts with desperately needed nuance,” Sacca argues, because many of Twitter’s problems are too complex to solve on his own.

Sacca concludes that Musk is “straight-up alone right now and winging this.”

A social media company is harder to manage than a car company

Musk has excelled in the areas of batteries, motors, rockets, tunnels, and solar panels, Sacca writes, because his “ability to note and question the assumptions implicit in the rest of our thinking is a rare type of genius I’ve only seen in the greatest minds.” But Sacca notes these industries have definitively right and wrong answers where success can be objectively measured, unlike a social media company, which has a lot more nuance.

“Humans aren’t math and physics problems. We are f**king messy,” Sacca says. He argues that Twitter won’t get better for users, advertisers won’t come back at scale, and Musk’s huge investment won’t pay off unless “there is genuine dialogue leading to thoughtful progress and stability.”

However, this is not what is happening at Twitter. Over time, Sacca has watched those around Musk become increasingly sycophantic and opportunistic: “Simply put, agreeing with him is easier, and there is more financial & social upside.

“I can’t sit by and watch a guy I’ve looked up to for over a decade fumble this opportunity, stoke more insanity, and likely hurt a bunch of folks in the process,” Sacca says.

Other founders in the same trap

This is a problem for many founder-led companies. Sacca points to Travis Kalanick, the founder of Uber, which Sacca also invested in at an early stage. Sacca says Travis is objectively brilliant “but as he became powerful only the suck-ups remained. He had no real friends left.”

Throughout his tenure as CEO, Kalanick had extremely tight control over the company’s board of directors, once telling Apple CEO Tim Cook that he had intentionally structured the board and handpicked its members to allow him to “do what I want,” Mike Isaac wrote in his book Super Pumped: The Battle for Uber.

In the end, “Travis had a board seat to fill, and there was almost no one he could put in it because he was alone,” Sacca says.

But one person who hasn’t fallen into this trap is Mark Zuckerberg, Sacca says. “Never been a fan, but at least that guy keeps some smart people around and sometimes listens. I hate most of their decisions, but they are free to suggest to Zuck that he’s full of sh*t.

“No one on Earth is good enough to get it all done on their own,” Sacca asserts.

Sign up for the Fortune Features email list so you don’t miss our biggest features, exclusive interviews, and investigations.

About the Author
Sophie Mellor
By Sophie Mellor
LinkedIn iconTwitter icon
See full bioRight Arrow Button Icon

Latest in Leadership

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Leadership

Keke Palmer
SuccessPersonal Finance
Keke Palmer became a millionaire at 12—but even with $1 million, she’d still only pay $1,500 in rent and drive a Lexus: ‘I live under my means’
By Emma BurleighFebruary 15, 2026
6 minutes ago
haque
CommentarySocial Media
I’m the CEO of the 1980s most viral restaurant, Tony Roma’s. We’re still thriving but viral brands keep turning into pumpkins
By Mina HaqueFebruary 15, 2026
23 minutes ago
C-SuiteMarketing
Adrien Brody’s multimillion‑dollar TurboTax Super Bowl ad: Intuit’s CMO explains why the software giant spends more on marketing than R&D
By Geoff ColvinFebruary 15, 2026
53 minutes ago
Denise Martin in front of her granny pod
SuccessHousing
Meet the grandmother living out of a 400-ft ‘granny pod’ to save money and help with child care—it’s become an American ‘economic necessity’
By Emma BurleighFebruary 15, 2026
2 hours ago
Dana Perino on the set at Fox News
SuccessCareers
Fox News’ Dana Perino’s advice for Gen Z graduates: Stop waiting for the perfect job and just start working
By Preston ForeFebruary 15, 2026
3 hours ago
simas
EconomyFlorida
Meet Florida Man 2.0: the executive working to replace retirees and Disney tourists with Fortune 500 HQs
By Nick LichtenbergFebruary 15, 2026
3 hours ago

Most Popular

placeholder alt text
AI
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
By Jake AngeloFebruary 13, 2026
2 days ago
placeholder alt text
Success
MacKenzie Scott says her college roommate loaned her $1,000 so she wouldn't have to drop out—and is now inspiring her to give away billions
By Sydney LakeFebruary 14, 2026
23 hours ago
placeholder alt text
Big Tech
Analog-obsessed Gen Zers are buying $40 app blockers to limit their social media use and take a break from the ‘slot machine in your pocket’
By Marco Quiroz-GutierrezFebruary 13, 2026
2 days ago
placeholder alt text
Economy
Some folks on Wall Street think yesterday’s U.S. jobs number is ‘implausible’ and thus due for a downward correction
By Jim EdwardsFebruary 12, 2026
3 days ago
placeholder alt text
AI
OpenAI's Codex and Anthropic's Claude spark coding revolution as developers say they've abandoned traditional programming
By Beatrice NolanFebruary 13, 2026
1 day ago
placeholder alt text
Personal Finance
Every U.S. Olympian was promised a $200,000 payout, but how much they actually keep depends on where they live
By Jacqueline MunisFebruary 11, 2026
4 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.