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...
12 days 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...
20 days 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...
27 days 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 1 month 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...
about 1 month ago • 8 min read
Reading time: 5 minutesListen time: 11 minutes Good morning. Two forces are reshaping litigation at once. Claims are getting more polished and more plentiful. The proof behind them is not keeping up. Generative AI can draft a flawless-looking brief in minutes. It cannot manufacture the evidence that brief needs. That gap is where this week's intelligence lives. Here's what's in front of you: Courts have now caught AI-invented citations in more than 1,700 filings (as of July 2026), and one...
about 2 months ago • 7 min read
Reading time: 5 minutesListening time: 6 minutes The Boardroom Brief — Quarter in Review America turns 250 this weekend. Nobody will mention insurance at the barbecue. But the industry you run is older than the country it's celebrating. Marine underwriters financed the Revolution when the colonies had no navy and no central bank. The receipts are real. So instead of a new Brief this week: ten editions from the past quarter that you told us mattered, measured in the ones you opened and the...
about 2 months ago • 5 min read
Negotiating D&O at Every Stage of the Build My first insurtech client was convinced he was going to be the Steve Jobs of insurance. Ten years ago he had everything investors wanted. A growth curve doubling every quarter. A proprietary pricing algorithm. And a claims and reserving operation so unglamorous it never made the deck. Guess which one kept him solvent. The growth curve drove the keynote. His algorithm set the valuation. The reserve discipline no one put in the deck is the only reason...
about 2 months ago • 4 min read
Reading time: 5 minutesListen time: 6 minutes Read the insurtech headlines this quarter and the story sounds simple: the money came back. It did, $1.6 billion of it. But it is not chasing insurance brands anymore; it is buying the rails underneath them. And nearly every dollar is going to a handful of AI-native plays writing the exact coverage your institution sells. The part the funding charts miss is the bigger shift: AI is now on both sides of your transaction, pricing the risk on one side...
2 months ago • 7 min read