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Which Insurance Tech Solutions Are The Most Insulated From AI?

Posted On March 4, 2026March 4, 2026 By Ian1 Comment

As I noted in recent posts, I had been working on a big piece about how AI could impact insurers including threats to data providers, brokers, D&O, the foolish carriers writing data center risk, and so on. That piece is now in the trash bin as current events moved too Continue Reading

Category: Entries

The AI Risk For Insurance Brokers…Part I

Posted On February 17, 2026February 17, 2026 By Ian6 Comments

This is going to be another shorter piece. Why? First, the response to last week was pretty good. Second, events in the AI space are moving too fast. For example, when the insurance technology provider (distinct from “insurtech”) stocks began their recent freefall, I pointed out to a few friends Continue Reading

Category: Entries

What Investors Are Getting Wrong About The Tech Selloff

Posted On February 9, 2026February 9, 2026 By Ian9 Comments

For those of you who pay attention to more than just insurance, you are likely aware it was a bad week for tech stocks. Software stocks have been crushed due to fears that AI will make them irrelevant while large tech also sold off over fears they are investing too Continue Reading

Category: Entries

Debunking Super Bowl Quarterback Myths

Posted On February 5, 2026February 5, 2026 By Iancomment

Since it’s Super Bowl week, I decided to update some data analysis around how Super Bowl teams acquire their starting quarterback. There is a widely held view that you have to have a “franchise” quarterback like a Tom Brady or Patrick Mahomes. Don’t get me wrong – that helps a Continue Reading

Category: Entries

Refilling the Cookie Jar

Posted On January 22, 2026January 22, 2026 By Iancomment

Election Results: Before getting into today’s topic, I wanted to release the results of the Best CEO vote! Your winner is actually not quite a CEO. His official title is Vice Chairman of Insurance at Berkshire Hathaway. That’s right your winner is Ajit Jain! Ajit has successfully managed the largest Continue Reading

Category: Entries

The Ten Biggest Events of the Insurance Quarter Century

Posted On January 15, 2026January 15, 2026 By Ian3 Comments

Reminder: You can still vote until next Tuesday on the Best CEO of the last 25 years. Click the link here and scroll to the poll at the bottom. There is a pretty tight three way race so any additional votes may swing the outcome. For this week, I am Continue Reading

Category: Entries

Vote For The Insurance CEO of the Quarter Century

Posted On January 6, 2026January 6, 2026 By Ian12 Comments

Happy New Year to everyone reading. This New Year holds a bit of extra significance as it means we are a quarter of the way through the 21st century. And that means it’s a great occasion for top 10 lists and voting for awards. In that spirit, I have decided Continue Reading

Category: Entries

The Signal From Progressive’s Monster Dividend Announcement

Posted On December 22, 2025December 22, 2025 By Iancomment

Editor’s Note: This will be the last post for the year. I’ll be back in early January with something fun for everyone to debate. Progressive recently announced a special dividend of $13.50/sh, equal to over $8B. To put in context how large that is, it amounted to nearly 25% of Continue Reading

Category: Entries

Why Chubb Shouldn’t Buy AIG

Posted On December 18, 2025December 18, 2025 By Iancomment

Today’s note is a little different. It’s essentially a direct letter to Evan Greenberg that I am sharing with the rest of you. You may have seen reporting that Chubb approached AIG about a takeover. As I’m sure you all know, Evan has deep personal ties to AIG as it’s Continue Reading

Category: Entries

Would It Be So Bad If AI Took Our Jobs?

Posted On December 9, 2025December 9, 2025 By Ian3 Comments

Last time I wrote a fairly negative view of the impact of AI. Today, I’m going to explore some of the ramifications of an optimistic view of AI’s potential. AI has the potential to be the next Industrial Revolution. There are obvious benefits to this from the increase in productivity Continue Reading

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Recent Posts

  • Which Insurance Tech Solutions Are The Most Insulated From AI?
  • The AI Risk For Insurance Brokers…Part I
  • What Investors Are Getting Wrong About The Tech Selloff
  • Debunking Super Bowl Quarterback Myths
  • Refilling the Cookie Jar

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