Thimble vs Simply Business: Which Is Better?
An on-demand insurtech that sells coverage by the hour versus a marketplace that shops 20-plus carriers for the best annual rate. Six rounds. Real numbers. One honest scorecard.
The verdict
Simply Business takes it, 4–2 on rounds.
These two are priced almost identically, so ignore the headline number and choose on structure — Thimble for burst, per-job work, Simply Business for steady, year-round operations and niche trades.
Choose Thimble if…
- • Your work comes in bursts — single events, seasonal gigs, occasional jobs
- • You want zero risk of a surprise annual renewal charge
Choose Simply Business if…
- • You operate steadily all year and want the cheapest shopped annual rate
- • You run an unusual trade that standard carriers won't quote directly
Round by round
- Round 1On-Demand Flexibility & SpeedThimble winsThimble9/10
From 1 hour
Shortest policy duration Thimble sells — hour, day, week or month
- Pay only for the exact window you work
- No standard annual policy option
Source: Thimble product model
Simply Business4/10Annual only
No hourly, daily or weekly option — standard year-long policies
- Better structure for steady, year-round work
- Nothing for a single job, event or short season
Source: Simply Business product model
So this round goes to Thimble.
- Round 2Carrier Choice & Price CompetitionSimply Business winsThimble4/10
1 on-demand product
Sold directly by Thimble, underwritten by partner carriers — no comparison shopping
- Fastest possible path to a certificate
- No competing quotes to compare
Source: Thimble product model
Simply Business8/1020+
Carriers Simply Business shops in a single application
- Real price competition on every quote
- One application returns competing quotes from every partner
Source: Simply Business marketplace model
Round to Simply Business on that.
- Round 3Coverage Breadth for Different TradesSimply Business winsThimble5/10
~130 professions
Tuned to freelance, event and short-job risks
- Deep, tuned fit for the mainstream gig and short-job crowd
- Narrower fit for unusual or niche trades
Source: Thimble footprint data
Simply Business8/10400+
Small-business types Simply Business will quote
- Places niche trades other carriers decline
- Backed by a stable of 20+ partner carriers
Source: Simply Business footprint data
This round goes to Simply Business.
- Round 4Billing & Renewal TrustThimble winsThimble8/10
0 auto-renewals
Coverage windows simply end — nothing to renew or auto-charge
- Zero surprise annual charges
- Structurally cannot auto-renew or auto-charge you
Source: Thimble product model
Simply Business4/10Documented auto-renewal complaints
- Recurring complaints about surprise renewal charges
- Cards charged before the policy was even due
So this round goes to Thimble.
- Round 5Underwriting Strength & Parent BackingSimply Business winsThimble6/10
Arch Capital
Parent since 2023; underwriting partners rated AM Best A- or higher
- Trustpilot ~4.6/5 buying experience
- No AM Best rating of its own
Source: Thimble notable facts
Simply Business8/10~$490M acquisition
Bought by Travelers in 2017; places you with A-rated insurers like CNA, Travelers, Hiscox
- Backed by one of the largest US carriers
- No AM Best rating of its own
Source: Simply Business notable facts
This one's Simply Business's, on the strength of the parent.
- Round 6Price for How You Actually WorkSimply Business winsThimble6/10
Cheapest per active hour worked
- No premium wasted on idle months
- Costlier than an annual policy for continuous work
Simply Business7/10~$97/mo
MoneyGeek 2026: third-most-affordable provider studied
- Best value for steady, year-round work
- A single shopped annual policy beats stacking twelve short-term Thimble policies
Source: MoneyGeek 2026
So this round goes to Simply Business. Better for steady work and overall value.
Which one is for you?
Wedding photographer or event vendor working a handful of gigs a year
→ Thimble · By-the-day coverage with an instant certificate beats paying for a full year
Freelancer who wants zero surprise renewal charges
→ Thimble · Coverage windows simply end — no auto-renewal to worry about
Year-round micro-business wanting the cheapest annual rate
→ Simply Business · Marketplace shops 20+ carriers for the best full-year price
Owner of an unusual or hard-to-place trade
→ Simply Business · 400+ business types quoted, including niches other carriers decline
Side by side
- No premium wasted between jobs
- Instant certificate for a single hour, day, or event
- Deep enough for straightforward freelance risk across ~130 professions
- No agent required at any point
- One application compares many insurers' prices at once
- Partners with A-rated carriers like Travelers and CNA
- Cheap, easy initial purchase
- Multi-carrier shopping can surface a lower quote for niche risks
- No cyber, EPLI, workers' comp or agribusiness lines
- Zero coverage for these specialized risks
- Not built for larger or more complex risk profiles
- Claims handled by the underwriting partner, not Thimble
- Final carrier and premium vary by which partner you're matched with
- Claims experience depends entirely on which partner you're matched with
- Recurring reports of auto-renewal at higher prices with little notice
- Final premium depends on which partner carrier is matched