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Jim Kaskade

Serial Entrepreneur, Global Enterprise Executive

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A CEO’s journey through culture, strategy, and execution

  • Jim Kaskade
  • January 28, 2026
  • Leadership

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
Eyespot Launches Plug-and-Play Video Production Studio for Online Content and Website Owners
  • Advertising
  • Broadband Video
  • SaaS

Eyespot Launches Plug-and-Play Video Production Studio for Online Content and Website Owners

  • Jim Kaskade
  • September 16, 2008
Eyespot Expands Online Video Network; Selects Limelight Networks to Serve Middle Market
  • Advertising
  • Broadband Video
  • SaaS

Eyespot Expands Online Video Network; Selects Limelight Networks to Serve Middle Market

  • Jim Kaskade
  • August 14, 2008
Eyespot Selected by AlwaysOn as an OnHollywood 100 Top Private Company Award Winner
  • Advertising
  • Broadband Video
  • Digital Media
  • SaaS

Eyespot Selected by AlwaysOn as an OnHollywood 100 Top Private Company Award Winner

  • Jim Kaskade
  • May 29, 2008
Investors strike gold in hallways
  • Broadband Video
  • SaaS

Investors strike gold in hallways

  • Jim Kaskade
  • May 2, 2008
Demand Media Taps Eyespot Video Platform to Power ExpertVillage.com, Cracked.com and eHow.com
  • Advertising
  • Broadband Video
  • SaaS

Demand Media Taps Eyespot Video Platform to Power ExpertVillage.com, Cracked.com and eHow.com

  • Jim Kaskade
  • May 1, 2008
Eyespot Shifts Focus to Mid-Tail Video Providers with Network Model
  • Advertising
  • Broadband Video
  • SaaS

Eyespot Shifts Focus to Mid-Tail Video Providers with Network Model

  • Jim Kaskade
  • April 28, 2008
Digital Action Sports Network to Launch Specialty Websites on Eyespot Video Platform
  • Advertising
  • Broadband Video
  • SaaS

Digital Action Sports Network to Launch Specialty Websites on Eyespot Video Platform

  • Jim Kaskade
  • April 25, 2008
Does Premium Viral Content Exist?
  • Advertising
  • Broadband Video
  • Digital Media
  • SaaS

Does Premium Viral Content Exist?

  • Jim Kaskade
  • April 10, 2008
WestSideLax.com Adds Video to Lacrosse Website With Eyespot Video Platform
  • Advertising
  • Broadband Video
  • SaaS

WestSideLax.com Adds Video to Lacrosse Website With Eyespot Video Platform

  • Jim Kaskade
  • April 9, 2008
Eyespot in RED HERRING 100
  • Broadband Video
  • Digital Media
  • SaaS

Eyespot in RED HERRING 100

  • Jim Kaskade
  • April 5, 2008

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Jim Kaskade (he/him) Follow 135,541 2,472

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 ·
23h 2078087466121056629

Investors do not fund businesses. They fund stories backed by entrepreneurs. Explain "why your business", but also explain "why you".

Playing it fwd (get my CEO Playbooks): https://operatoros.jameskaskade.com/

#OperatorOS

Image for the Tweet beginning: Investors do not fund businesses. Twitter feed video.
Reply on Twitter 2078087466121056629 Retweet on Twitter 2078087466121056629 0 Like on Twitter 2078087466121056629 0 X 2078087466121056629
jimkaskade avatar Jim Kaskade (he/him) @jimkaskade ·
16 Jul 2077725109725409407

Every CEO needs at least one session per year (if not per quarter) where the agenda is not about the roadmap. Have you sponsored company-wide Hackathons that can last up to a week?

Playing it fwd (get my CEO Playbooks): https://operatoros.jameskaskade.com/

#OperatorOS

Image for the Tweet beginning: Every CEO needs at least Twitter feed video.
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jimkaskade avatar Jim Kaskade (he/him) @jimkaskade ·
15 Jul 2077362706567323832

Know your competitive position before you update your strategy. SWOT is not a slide. It is a forcing function.

Playing it fwd (get my CEO Playbooks): https://operatoros.jameskaskade.com/

#OperatorOS

Image for the Tweet beginning: Know your competitive position before Twitter feed video.
Reply on Twitter 2077362706567323832 Retweet on Twitter 2077362706567323832 0 Like on Twitter 2077362706567323832 0 X 2077362706567323832
jimkaskade avatar Jim Kaskade (he/him) @jimkaskade ·
14 Jul 2077047820150837443

Peer accountability is the most powerful performance tool a CEO has. Use it every QTR. I have an approach that starts with declarations of performance vs. potential, but ends with complete transparency.

Playing it fwd (get my CEO Playbooks): https://operatoros.jameskaskade.com/

#OperatorOS

Image for the Tweet beginning: Peer accountability is the most Twitter feed video.
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