Dell’s Darlings
This week’s Dell-led take-private offers an occasion to revisit MSI—think insurance at the point of lease—and consider how Baldwin and Lemonade, each now reporting a reach of more than 3 million—clients for Baldwin, customers for Lemonade—took radically different routes to nearly identical revenue-growth multiples. Lemonade built a consumer insurer; Baldwin assembled a distribution platform.
The Baldwin Group was founded in 2011, but its roots trace to Baldwin & Sons, the Tampa insurance agency Lowry Baldwin joined in 1983, and BKS Partners, which he co-founded in 2006. His son Trevor joined in 2009, co-founded Baldwin Risk Partners, and took it public in 2019 as a founder-controlled acquisition roll-up: $79.9 million in 2018 revenue, more than 400,000 clients, and $169.8 million in debt.
MSI, acquired only months before the offering, was presented as Baldwin’s “MGA of the Future” — a national renters operation distributing coverage through subagents, property-management software providers, and other embedded channels.
MSI was to Baldwin what AP Intego failed to become for Next Insurance. Baldwin made it to the public markets; Next became ERGO’s Next instead of earning a ticker of its own.
Founded in 2015, MSI is Baldwin’s darling. Millennials have little to do with its success. Renters insurance is often required, and MSI sells it in the right place, at the right time, and at the right price.
The Baldwin/MSI deal closed in April 2019, months before Baldwin’s October 2019 IPO—which came about nine months before Lemonade completed its own IPO in July 2020 as a renters and homeowners insurer. Pet arrived that same month.
Baldwin paid $45.5 million in cash and initially valued total consideration at $103.2 million. Of that, $53.8 million was recorded as goodwill. The agreement also provided for up to $61.5 million in contingent earnout.
The more digestible figure: MSI’s policies in force grew 35% in 2018 to 271,908 and reached 352,054 as of September 22, 2019 — another 29.5% in less than nine months.
For comparison, Lemonade — a home and renters insurer at the time — reported 643,118 customers at year-end 2019, though it never disclosed how many were renters — just that “the large majority of our users are renters.”
MSI’s growth continued. Policies in force for the MSI Partnership rose by 168,015, or 32%, to 692,385 by the end of 2021, from 524,370 a year earlier. Lemonade reported 1,427,481 customers in 2021, up 43% from 1,000,802 in 2020 — but by then the comparison was breaking down. Lemonade counts customers, not policies, and by 2021 it spanned renters, homeowners, life, pet, and car.
Today, MSI ranks sixth by 2025 MGA premium, at $760.1 million, according to our analysis. Ahead of it: CRC Insurance Group ($1.72 billion), Hagerty ($1.03 billion), Arrowhead General Insurance Agency/Brown & Brown ($937 million), Bowhead Specialty ($819 million), and Windward Risk Managers ($771.4 million).
Baldwin serves more than 3 million clients across the US and internationally, and MSI is a substantial piece of the pie. MSI had roughly 300,000 policies around the time of its acquisition, against Baldwin’s more than 400,000 clients; today, it has a reported customer count equal to roughly half Baldwin’s companywide client count.
And if you remember Lemonade’s “Killer Prices,” here is the killer insight following this week’s Dell-led deal: Baldwin and Lemonade delivered virtually identical revenue-growth multiples, by opposite methods.
Baldwin commissions and fees: $137.8 million in 2019 → $1.5 billion in 2025, or 10.9×
Lemonade revenue: $67.3 million in 2019 → $737.9 million in 2025, or 11×
Only the multiples are comparable: Baldwin’s figure represents brokerage and MGA revenue, while Lemonade’s represents insurer revenue. Both grew at the same rate, but on fundamentally different economics.
Lemonade entered renters positioning itself against a dated insurance experience, not against any one incumbent. But the incumbent was always Assurant — embedded renters distribution through property managers and affinity partners, at scale. That is the channel MSI proved out, and it is the channel the field is now crowding into. Great American is rolling out a personal renters program built for property managers, property-management software platforms, and affinity partners. Chubb is developing digital renters and valuables coverage for HENRYs — high earners not rich yet — “the next wave of PRS high-net-worth clientele.” AmTrust distributes renters through embedded channels and plans to expand into participating apartment communities. Corgi has filed an admitted homeowners and renters product in Georgia.
Renters has never looked more strategically valuable—as an embedded product, an entry point to affluent customers, and a bridge to homeowners. The market Lemonade helped modernize is now changing around it.
And now, Obie is Baldwin’s new darling—the MSI playbook rerun in a new line, except this time Baldwin will build privately, with patient capital behind it. Founded in 2017, the landlord-insurance MGA raised roughly $39 million before joining Baldwin in January 2026. Baldwin recorded $287.4 million in total consideration, including $87 million in cash. If Obie hits every earnout target, the deal’s ultimate value could reach ~$480.6 million.
Two words:
Bold win.