The verdict
biBERK takes it, 3–2 on rounds.
There's no universal winner — biBERK and Thimble are built for opposite rhythms of work, so match the policy structure to the shape of your actual calendar.
Choose biBERK if…
- • You work continuously all year and want one flat, predictable annual premium
- • You want a single Berkshire-backed carrier accountable for the whole policy
Choose Thimble if…
- • You work in bursts — events, gigs, or seasonal jobs with real gaps between them
- • You regularly need to prove coverage fast with an on-demand certificate
Round by round
- Round 1Policy Duration & FlexibilityThimble winsbiBERK5/10
12-month terms
Conventional annual policy structure, no short-duration option
- Right structure for continuous, year-round operation
- No way to buy coverage for a single job or day
Source: biBERK dossier
Thimble10/101 hour minimum
Buy by the hour, day, week or month — pay only for the time you're exposed
- Zero wasted premium between gigs
- Ideal for one-off gigs like weddings or weekend jobs
Source: Thimble dossier
So this round goes to Thimble on flexibility.
- Round 2Who Actually Underwrites the PolicybiBERK winsbiBERK9/10
A++ (Superior)
Berkshire Hathaway subsidiaries — the highest AM Best rating that exists
- Berkshire's insurance arm paid ~$62B in claims in 2025
- One company sells the policy and pays the claim — no partner to route to
Source: AM Best ratings (biBERK dossier)
Thimble5/10MGA, not a carrier
Partner carriers like Markel and Employers underwrite, rated A- or higher
- Backed by Arch Capital since the 2023 acquisition
- No AM Best rating of its own
Source: Thimble dossier
So this round goes to biBERK, thanks to clear backing and one-stop claims handling.
- Round 3Certificates of Insurance On DemandThimble winsbiBERK5/10
Standing annual coverage
Online policy management, but not built for ad-hoc per-job certificates
- Self-serve portal lets you pull your own documentation online
- Not built for spinning up a fresh certificate per job
Source: biBERK dossier
Thimble9/10~4.6/5
Trustpilot rating across 1,200+ reviews — strong on the buying/certificate experience
- Certificates generated and shared on demand, mid-job
- Generate certificates directly from the app, no waiting on an agent
Source: Thimble dossier (Trustpilot)
Round to Thimble on that. Faster, on-demand certificates just make life easier out there.
- Round 4Claims & Customer ServicebiBERK winsbiBERK6/10
One carrier handles the whole claim
- Single accountable carrier for every claim
- Higher-than-expected regulator complaint volume
Thimble5/10Claims routed to the underwriting partner
- Backed by underwriting partners rated A- or higher by AM Best
- Claims handled by whichever partner carrier wrote the policy
Round goes to biBERK on accountability.
- Round 5The Real Year-Round MathbiBERK winsbiBERK8/10
~$105/mo avg
Flat annual pricing; GL from ~$30/mo for low-hazard businesses
- Predictable cost regardless of how many weeks you work
- One premium, twelve months, done
Source: biBERK dossier (MoneyGeek 2026)
Thimble6/10from $17/mo
Cheapest per gig, but can exceed annual pricing if stacked all year
- Unbeatable for occasional, short-duration work
- Can cost more per unit of time than an annual policy
Source: Thimble dossier
Round to Thimble — for the freelancer who works in fits and starts.
- Round 6Who Each One Was Built ForTiebiBERK8/10
Year-round fit
Continuous annual coverage for a business that operates every week
- Built for consultants, contractors and office-based firms with no off-season
- No need to re-shop coverage every few months
Source: biBERK dossier
Thimble8/10170,000+ policies
Delivered to gig and short-duration businesses across ~130 professions since 2018
- Purpose-built for burst, on-and-off schedules
- Serves ~130 different professions in the gig/short-duration space
Source: Thimble dossier
So this round goes to Thimble.
Which one is for you?
Wedding photographer who shoots a dozen weekends a year
→ Thimble · Paying only for event days plus on-demand certificates beats a full annual premium for occasional work.
Pop-up vendor or one-off event operator
→ Thimble · Thimble can cover a single day or event, exactly matching a short, defined exposure.
Consultant or freelancer working full-time all year
→ biBERK · Year-round work makes biBERK's flat annual GL and E&O cheaper than stacking short policies.
Owner who wants a single accountable carrier if a claim goes wrong
→ biBERK · biBERK is one carrier end-to-end; Thimble routes claims to an underwriting partner.
Side by side
- Instant online quote-and-bind, no agent required
- Backed by Berkshire, which paid ~$62B in claims in 2025
- AM Best's single highest financial-strength grade available
- All essentials from one A++-backed carrier
- 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
- No local agent relationship if you want one
- Higher-than-expected state regulator complaint volume relative to market share (NerdWallet)
- Long hold times and AI phone systems reported
- No cyber, management liability or group benefits
- 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