$628B Boom Meets $555M Bet: The Insurance Plays Reshaping Capital

Good morning, ! This week we’re tracking shifts in cyber claims (ransomware down, breaches up), the $628B home insurance growth story, and Skyward Specialty’s $555M Lloyd’s play. Plus: insurtech funding trends, the Fed’s fiscal squeeze, and where M&A is heating up. 

Join 50+ advertisers who reach our 400,000 executives: Start Here.

Know someone who would love this? Pass it along—they’ll thank you later. Here’s the link.

DATA DIVE

The $628B Question

The global home insurance market is on track to nearly double in size, growing from $269.9B in 2024 to $628.5B by 2034 (CAGR: 8.8%). The usual suspects are at play: rising property values, climate-driven catastrophes, and a surge in digital-first platforms. North America still holds the crown (31% share), but Asia-Pacific is the real growth story—urbanization plus a 96% urban homeownership rate in China makes it a sleeping giant. In the U.S., State Farm (20%) and Allstate (15%) dominate a market expected to hit $149.5B by 2034. The catch? Affordability and reinsurance costs threaten to turn “growth story” into “coverage gap” if left unchecked.

Read the Full Report HERE

TREND OF THE WEEK

What’s Up (and Down) in Cyber Claims

MunichRE highlights that ransomware may finally be cooling—down from 38% in 2022 to 32% projected in 2024—but don’t pop champagne yet. Data breaches are up, hitting 47%, and fraud isn’t budging, stubbornly above 40%. The chart says what many underwriters already suspect: threats aren’t declining—they’re diversifying. This forces a rethink in pricing, coverage, and risk prevention, especially as AI-fueled scams blur the lines between software vulnerability and social engineering. With cyber insurance projected to hit $29B by 2027, the money’s still flowing—but so are the threats. Insurers that keep clinging to ransomware models risk fighting yesterday’s war. (More)

PRESENTED BY PACASO

How 433 Investors Unlocked 400X Return Potential

Institutional investors back startups to unlock outsized returns. Regular investors have to wait. But not anymore. Thanks to regulatory updates, some companies are doing things differently.

Take Revolut. In 2016, 433 regular people invested an average of $2,730. Today? They got a 400X buyout offer from the company, as Revolut’s valuation increased 89,900% in the same timeframe.

No wonder 10K+ everyday people are taking the chance on Pacaso.

Founded by a former Zillow exec, Pacaso’s co-ownership tech reshapes the $1.3T vacation home market. They’ve earned $110M+ in gross profit to date, including 41% YoY growth in 2024 alone. They even reserved the Nasdaq ticker PCSO.

The same institutional investors behind Uber, Venmo, and eBay backed Pacaso. And you can join them. But not for long. Pacaso’s investment opportunity ends September 18.

Invest While You Still Can

_{Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.}

INSURTECH CORNER

The Rise of the “Almost Big” Check

InsurTech’s funding diet is still lean on calories, but there’s a new snack on the menu: mid-sized deals. In 2024, 53% of financings sat below $10M, a repeat of 2023’s pattern. So far in 2025, that hasn’t changed much—54% of deals are still sub-$10M—but the share of $25–50M rounds crept up to 14% (vs. 11% in prior years). The $100M+ mega-rounds? Still stranded at just 5%. For founders, this means survival still requires efficient burn, but a handful are finding room to scale. For investors, the bar for growth checks is higher—only companies with profitable-looking distribution or sticky product-market fit will break through. For the sector, it’s clear: innovation is alive, but the era of category-defining capital waves is still on pause.

DEAL OF THE WEEK

Skyward Specialty’s $555M Play for Lloyd’s Access

Skyward Specialty is going transatlantic.

The U.S.-based specialty insurer just announced its $555M acquisition of Apollo Group Holdings, a Lloyd’s of London underwriting platform known for tech-forward syndicates like ibott. The deal breaks down to $184M in stock and $371M in cash, and is expected to close in Q1 2026.

The move gives Skyward a major foothold inside Lloyd’s, adding over $1.5B in managed premium and extending its niche underwriting model into global lines like political violence, product recall, and digital economy liabilities. Apollo’s 20% GWP CAGR since inception and capital-light structure made it an attractive target, but it’s the cultural fit that sealed it—CEO Andrew Robinson says the firms share a vision to “Rule Our Niche.”

For FIG strategists, this is a signal: specialty consolidation is going global, and U.S. players are no longer content with domestic dominance. Expect similar cross-border deals as carriers chase scale, tech-savvy syndicates, and diversified risk books in the face of rising volatility. (More)

TOGETHER WITH MAVEN AGI

AI Agents That Cut Support Costs By Up To 80%

AI Agents Designed For Complex Customer Support

Maven AGI delivers enterprise-grade AI agents that autonomously resolve up to 93% of support inquiries, integrate with 100+ systems, and go live in days. Faster support. Lower costs. Happier customers. All without adding headcount.

👉 Book your demo to see how.

MACROECONOMICS

The Fed’s Dilemma Has a Name: Fiscal Dominance

Fiscal dominance isn’t a forecast — it’s a working theory with a live test subject: the U.S. economy. With debt over $33T, multi-trillion-dollar deficits still rolling in, and 80% of debt now held by the public, the Fed’s “independence” is starting to look more ceremonial than practical. The 6.3% deficit-to-GDP ratio screams crisis, but unemployment is low. Translation: we’re borrowing like it’s 2009, minus the recession. Investors are responding: TIPS allocations are up, and sovereign hedging is in vogue. As monetary policy gets boxed in by fiscal needs, long-duration assets, LBO math, and fixed income arbitrage are all under new stress tests. (More)

INTERESTING ARTICLES

TWEET OF THE WEEK

"The purpose of our lives is to add value to the people of this generation and those that follow."

Buckminster Fuller