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
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Startup Life

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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.

Dig|In 2019

Dig|In 2019

Dig | In

The Digital Future of Insurance

May 29-31, 2019 | Austin, TX

 

Digital insurance is changing quickly, with every insurer in the market investing in digital strategies and deploying solutions – portals, mobile apps, home or personal devices and more—as they make digital strategy the heart of how they serve markets and customers. Along with this, the number of insurtech startups grows by the week as entrepreneurs and investors seek to capitalize on this rapidly changing market.

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Interview with Andrew Egenes - Layr

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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.

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Innovation as a step function

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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.