Gilad Shai
Weekly Investment & Strategic Deals: Dec ...

Week of Dec 22–28, 2025 (WW52)

Late December is typically a dead zone for announcements. This year was different.

While primary dealmaking slowed, several material funding rounds, strategic partnerships, and ecosystem moves were formalized or surfaced during the holiday window—particularly across embedded real-estate insurance, commercial auto MGAs, and insurance-specific financial automation.

The pattern is consistent with broader 2025 dynamics: fewer announcements, but higher signal per deal, and capital continuing to flow toward platforms that control workflow, data, or distribution.

Weekly Investment & Strategic Deals: Dec 22–28, 2025
Alex Devoto
Scream

The 1996 movie ‘Scream’ taught us one thing: Don’t answer the phone! And much like the characters of that movie, so to insurers should heed this advice when engaging with Millennials.

Scream
Entrepreneurship, Startup
Gilad Shai
Startup Life

A startup has a life but the people who breathe life into it…, well, they usually don't.

People like the idea of a startup. It is romantic. The excitement diminishes when they find out the extent of their responsibility and compensation. Basically, most people really want to work for Google. Google is a multibillion-dollar behemoth that has all the risk management tools and processes to support it. And yes! They still have all the perks and cool parties at the end of Google I/O.

Innovation, Overview, Startup, Trends
Gilad Shai
Innovation as a step function

Step Up

The entrance of startups to the insurance industry, nearly four years ago (2015), introduced a change, innovation, that made all the components, whether they are linear or passive, to react. The new teen spirit that the startup introduced acted as a step function that increased the value of the industry. The input may be a nice and clean function. It has a ripple effect that affects the entire pond until is converges on the new and higher level.

Innovation as a step function

Brokers

, , ,

Q4 2025 INSURANCE & INSURTECH M&A

, , ,
Q4 2025 INSURANCE & INSURTECH M&A

Q4 2025 marked a turning point in insurance and insurtech M&A, with fewer but significantly larger deals reshaping the market. Insurtech M&A surged to 21 transactions in Q3 2025—the highest level since Q3 2022—even as overall insurtech deal volume fell to just 76, the lowest count in years. At the same time, traditional insurance consolidation was dominated by megadeals such as Gallagher’s $13.45 billion acquisition of AssuredPartners, underscoring how scale, specialty capabilities, and technology are now central to competitive strategy across the sector.

, , , , ,

Bold Penguin, InsNerds at InsurTech LA

, , , , ,

The idea was to bring Ryan Hanley, CMO of Bold Penguin (at that time), to talk about Bold Penguin, Marketing and Commercial insurance. Ryan is a source of endless energy (check out his site https://ryanhanley.com/) that I wanted to introduce to the local scene.

Bold Penguin caters to agents and broker by providing them leads reselling their surplus leads. So, I asked Nick Lamparelli from InsNerds and Profile and Risk podcast to join the party.

Thank you for ORACLE for hosting InsurTechLA event at their Santa Monica offices.

InsurTechLA at Orcle.JPG
ORACLE InsurTech LA.JPG
, ,

Interview with Andrew Egenes - Layr

, ,
Interview with Andrew Egenes - Layr

Andrew Egenes is Co-Founder and Head of Product for Layr.

Layr is an AI-powered business insurance platform that automates the role of brokers and underwriters which enables small business owners to purchase insurance tailored to their company in minutes while performing the most common insurance-related tasks from a simple self-service portal.