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Jim Kaskade

Serial Entrepreneur, Global Enterprise Executive

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  • I’m an ENTJ
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Portfolio Companies On The Naughty and Nice List

  • Jim Kaskade
  • December 23, 2025
  • Artificial Intelligence
  • Leadership

Board of Directors at an AI Company

  • Jim Kaskade
  • July 5, 2025
  • Artificial Intelligence
  • Leadership

Corp Dev at an AI Company

  • Jim Kaskade
  • July 4, 2025
  • Artificial Intelligence
  • Leadership

R&D at an AI Company

  • Jim Kaskade
  • July 4, 2025
  • Artificial Intelligence
  • Leadership

International Operations at an AI Company

  • Jim Kaskade
  • July 4, 2025
  • Artificial Intelligence
  • Leadership

Finance at an AI Company

  • Jim Kaskade
  • July 4, 2025
  • Artificial Intelligence
  • Leadership

HR/People at an AI Company

  • Jim Kaskade
  • July 1, 2025
  • Artificial Intelligence
  • Leadership

Legal at an AI Company

  • Jim Kaskade
  • July 1, 2025
  • Artificial Intelligence
  • Leadership

DevSecOps at an AI Company

  • Jim Kaskade
  • June 30, 2025
The Dawn of a Transformative AI Journey
  • Artificial Intelligence

The Dawn of a Transformative AI Journey

  • Jim Kaskade
  • October 24, 2019
Culture = Competitive Advantage
  • Leadership

Culture = Competitive Advantage

  • Jim Kaskade
  • October 10, 2019
10Xers – Leadership that thrives in Chaos
  • Leadership

10Xers – Leadership that thrives in Chaos

  • Jim Kaskade
  • September 7, 2019
Humility + Will = Level 5
  • Leadership

Humility + Will = Level 5

  • Jim Kaskade
  • August 31, 2019
iNSYNQ’s FAQ: “How did this happen?”
  • Security

iNSYNQ’s FAQ: “How did this happen?”

  • Jim Kaskade
  • July 20, 2019
The Executive Chairman Starter Kit
  • Leadership

The Executive Chairman Starter Kit

  • Jim Kaskade
  • June 5, 2019
Creating CEO Playbooks
  • Leadership

Creating CEO Playbooks

  • Jim Kaskade
  • May 6, 2019
When do you achieve breakeven?
  • Leadership

When do you achieve breakeven?

  • Jim Kaskade
  • May 2, 2019
When should you scale sales?
  • Leadership

When should you scale sales?

  • Jim Kaskade
  • May 1, 2019
Extension Teams
  • Leadership

Extension Teams

  • Jim Kaskade
  • May 1, 2019

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Jim Kaskade (he/him) Follow 126,787 2,429

CEO for 25 years. Focused on AI, Security, Identity, IoT, Big Data, Social, Mobile, & Cloud. Decade in data warehousing, business intelligence, data mining.

jimkaskade
jimkaskade avatar Jim Kaskade (he/him) @jimkaskade ·
22 Dec 2002993355605614688

That Time I Tried to Buy OpenAI - https://bloom.bg/4j93360

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That Time I Tried to Buy OpenAI

Could a retail investor buy a single share of the privately held company? The assignment was alluring. It also revealed a few important lessons.

Bloomberg.com
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jimkaskade avatar Jim Kaskade (he/him) @jimkaskade ·
22 Dec 2002993351595864327

AI: Google jumps to Gemini 3 Flash vs OpenAI. RTZ #943 - Michael Parekh https://bit.ly/4j9y0Hf

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jimkaskade avatar Jim Kaskade (he/him) @jimkaskade ·
22 Dec 2002993353672052908

OpenAI 'Compute Margin' Doubles Over Nearly Two Years | https://bit.ly/4q0K7sM

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OpenAI 'Compute Margin' Doubles Over Nearly Two Years | PYMNTS.com

OpenAI has reportedly seen better margins from its paid offerings this year. A report Sunday (Dec. 21) from The ...

PYMNTS.com
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