Skim time: 5 minutes · Listening time: 7 minutes. Prefer to listen? Flip reads this week's Brief here. In May 2022, a ransomware crew locked up the systems at CiCi Enterprises, the company behind the Cicis pizza chain, and threatened to publish what it had taken. The demand was $2 million. The negotiators got it to $400,000. By the time the systems were back, the bill was more than $1.2 million. CiCi had a $3 million cyber policy. The carrier paid $250,000. The claim was covered. The...
8 days ago • 9 min read
Skim time: 5 minutes · Listening time: 7 minutes. Prefer to listen? Flip reads this week's Brief here. Kaiser Permanente is one of the largest health systems in the country. In January it settled a False Claims Act case with the Justice Department for more than half a billion dollars. It had bought a $95 million directors and officers (D&O) tower for exactly this kind of claim. The carriers paid $1 million. Not because the claim wasn't covered. The primary carrier said it was. The reason was...
15 days ago • 10 min read
Skim time: 5 minutes · Listening time: 6.6 minutes. Prefer to listen? Flip reads this week's Brief here. Ninety pages of comment letters crossed my desk this week. On a Wednesday night. My wife asked what could possibly be in there. The price of your carrier's balance sheet. Fitch, KBRA, and S&P Global wrote to state regulators. So did the American Council of Life Insurers, two investor and analyst associations, and one policy institute. The same complaint runs through all of them in...
22 days ago • 7 min read
Skim time: 5 minutes · Listening time: 6.5 minutes. Prefer to listen? Flip reads this week's Brief here. The future of brokerage looks like a team of AI agents with job descriptions, working on platforms like Grok Bot and Buzz. On those platforms a digital worker gets its own login and its own queue, and everything it does leaves a trail. A licensed human still signs everything that matters. I believe that enough to be running a small agent pilot in my own shop right now. Twenty-five years in...
29 days ago • 10 min read
Reading time: 5 minutes · Listening time: 6 minutes. Prefer to listen? Flip reads this week's Brief here. Over the last week I have had the same conversation with three clients: an insurtech with an embedded auto product, a massive MGA putting half a billion dollars a year into the market, and a newer MGA writing monoline environmental for a major US carrier. Different books, same problem. A claim comes in against the errors and omissions policy. Months later the argument has moved to what...
about 1 month ago • 9 min read
Reading time: 9 minutes · Listening time: 6 minutes. Prefer to listen? Flip reads this week's Brief here. Nobody in your renewal meeting will say the word "hardening." They'll just stop offering decreases. I sat in two rooms this week with senior underwriters from two of the largest financial lines carriers in the market. Two different companies, nearly the same conversation. Both raised the NERA and Cornerstone midyear reports before I did. Both cited those reports as the thing justifying...
about 1 month ago • 11 min read
Reading time: 5 minutes · Listening time: 7 minutes. Prefer to listen? Flip reads this week's Brief here. For two years I've heard the same cyber story. AI is making hackers faster. AI is making attacks cheaper. AI is making your team fall behind. All true. But somewhere along the way we stopped asking the obvious follow-up. What about our side? A farm mutual in Indiana answered that question, and I'm spending the whole edition on it because the story touches cyber, D&O (directors and...
about 2 months ago • 7 min read
Reading time: 5 minutes · Listening time: 6 minutes. Prefer to listen? Flip reads this week's Brief here. For twenty-five years I have watched carriers buy each other for scale. The pitch is always the same: a bigger combined book with cost synergies in year two. A stronger negotiating position with reinsurers. I've nodded through that deck more times than I can count. Most of those deals didn't pay what they promised. I knew it. The CFOs across the table probably suspected it. Nobody had the...
about 2 months ago • 7 min read
Reading time: 5 minutes 🎧 Listening time: 6 minutes — prefer to listen? Flip reads this week's Brief here. Boards got impatient with their CEOs. Attackers are more organized than they've ever been. And FI regulators are moving faster than I've seen in 20 years. Your underwriters are stressing about all three. Lately I've felt like the cranky old insurance version of the get off my lawn guy. Saying to anyone that will listen: "Insurance programs simply weren't built for this era." This week...
2 months ago • 8 min read