13 problems, 40 tools, free anchors first —
the free option leads each category and the paid tools follow as what you'd move up to.
Researched the way the whole site is: each entry is read from the company's own
pages and carries its check date — and we have not used these tools ourselves. 6
entries where the cost couldn't be read from their pages say so
plainly rather than borrowing a number from an article.
Three things most 1099 workers don't know exist.
Not recommendations — categories worth knowing about before you need them.
The S-corp lever. THE MECHANISM, plainly: a sole proprietor pays self-employment tax on all net earnings. An LLC that elects S-corp status pays its owner a reasonable W-2 salary and can take remaining profit as distributions not subject to self-employment tax. For someone clearing real income the difference is commonly four figures a year.
A threshold matters — below some income the admin outweighs the savings — and where that line
sits moves with tax law and your numbers, so ask a professional rather than trusting anyone's
round number, including ours. The category.
Thimble. By-the-job general liability with instant certificates of insurance. WHY THIS IS HERE: our directory has read hundreds of courier and contractor ads demanding things like "$300k general liability with us named as additional insured" before any work — this is the category of tool that answers that ad the same day. A customer's words on their page: after days of searching for "the perfect Certificate of Insurance ... in a couple of clicks I managed to obtain exactly what I needed." Its category.
Opolis. A member-owned employment cooperative that makes you a W-2 EMPLOYEE OF THE CO-OP while you keep working for yourself — "group rates, compliant payroll, W-2 status," their words. WHY THIS IS HERE: pay stubs and W-2s are what landlords and lenders ask for, and being 1099 is what stops gig workers from renting apartments and qualifying for car loans. Nothing else in this reference touches that problem. Group health, dental and retirement ride the same membership. Its category.
Pay your taxes without a payroll department
IRS Direct Payfree anchor Pay quarterly estimated taxes straight from a bank account, no account signup, no fee.
Cost: Free — government service · Needs: A bank account and your identity details. · checked 2026-08-28
Keeper Deduction-finding plus e-file; their words: the return "is reviewed & signed by a tax pro."
Cost: Standard $199/yr · Premium $399/yr — their plans page · Needs: Linking accounts for deduction scanning. · checked 2026-08-28
Solo (tax filing) Gig-specific tax filing from the same app that tracks earnings.
Cost: For subscribers: $75 DIY / $175 Expert Assist; non-subscribers $125 DIY — federal and state included, their pricing · Needs: Their app. · checked 2026-08-28
FlyFincost unresolved Their words: "AI finds every tax deduction" and "expert CPAs file your taxes from start to finish," with "full audit insurance."
Cost: UNRESOLVED — their pricing page 404s and the homepage states no figure (searched 2026-08-28: /pricing and the homepage) · Needs: Not stated on the pages read. · checked 2026-08-28
Track the miles and expenses that cut your tax bill
Stridefree anchor Free mileage and expense tracking, bundled with their health-coverage navigation.
Cost: Free · Needs: Their app. · checked 2026-08-28
MileIQ Automatic drive detection with swipe-to-classify and tax-compliant reports. Owned by Bending Spoons (their own footer).
Cost: 40 free drives every month at $0; unlimited at $11.66/mo billed annually or $13.99/mo monthly — their pricing page · Needs: Their app running in the background. · checked 2026-08-28
Everlancecost unresolved Mileage and expense tracking with a tax-filing add-on carrying, in their words, "$1 Million dollar tax protection."
Cost: PARTLY RESOLVED — a free tier exists and their pricing page carries $8.99–$19.99/mo and $69.99–$119.99/yr figures, but the tier labels did not render cleanly to our reader (searched 2026-08-28: their pricing page) · Needs: Their app. · checked 2026-08-28
Hurdlrcost unresolved Automatic mileage, expense and real-time tax estimates; their claim: freelancers "find over $5,600 in tax deductions" on average.
Cost: PARTLY RESOLVED — free tier plus Premium and Pro exist; exact tier prices did not render cleanly to our reader (searched 2026-08-28: their pricing page) · Needs: Their app. · checked 2026-08-28
Know what you actually earn across apps
Gridwise Automatic earnings and mileage tracking across gig apps — "know you're earning what you deserve," their words.
Cost: Free to download with a 14-day trial of paid plans; plan prices live in-app, not on the pages we read · Needs: Linking your gig accounts. · checked 2026-08-28
Solo Earnings tracking plus PAY PREDICTION WITH A GUARANTEE — their words: "$25m+ guaranteed using Solo's pay predictions." If a predicted shift underpays, they cover the gap per their guarantee terms.
Cost: Subscription (Solo Pro, 7-day free trial); tax filing priced separately — see the taxes category · Needs: Linking your gig accounts. · checked 2026-08-28
Moves Financial gone The gig-banking consolidator appears gone. Recorded so you don't go looking for it on an old article's word.
Cost: DATED NON-ANSWER — both domains unreachable on 2026-08-28 · checked 2026-08-28
Keep books and send invoices
Wavefree anchor Real double-entry bookkeeping, unlimited invoicing, tax-ready reports — the free anchor of the whole category.
Cost: Starter plan $0 — "create unlimited estimates, invoices" in their words; they charge per-transaction for card payments and sell a Pro tier ($16/mo-region on their page) · Needs: An account. · checked 2026-08-28
FreshBooks Invoice-first accounting for freelancers who bill clients for time and projects.
Cost: Lite $23/mo list, Plus $43/mo list (steep intro discounts shown); payroll add-on $40/mo + $6/user — their pricing page · Needs: An account. · checked 2026-08-28
Bonsai Contracts, proposals, CRM, time tracking and invoicing in one; now "Bonsai, a Zoom company" (their footer). Drifting toward team software — strongest fit for client-work freelancers, thin for drivers.
Cost: Basic $9 / Essentials $19 / Premium $29 per user/month billed annually — their pricing page · Needs: An account. · checked 2026-08-28
Save for retirement without an employer plan
Fidelity (SEP-IRA / Solo 401k)free anchor Self-employed retirement accounts (SEP-IRA, Solo 401(k)) at a mainstream brokerage.
Cost: "No account fees or minimums to open" — their words; fund expenses still apply · Needs: Self-employment income; contribution limits on their pages. · checked 2026-08-28
Schwab (Individual 401k)free anchor Individual 401(k), traditional and Roth.
Cost: "$0 account open or maintenance fees," $0 minimum deposit — their words · Needs: Self-employment income. · checked 2026-08-28
Carry A paid Solo-401k platform (crypto and alternative assets in Pro). Their own banner, 2026-08-28: "Carry is joining Lettuce Financial Labs" — the category is consolidating.
Cost: Core $299/yr · Pro $499/yr — their pricing page · Needs: Self-employment income. · checked 2026-08-28
Health coverage without an employer
Healthcare.gov (self-employed)free anchor The ACA marketplace's self-employed door: enroll without an employer, income-based subsidies.
Cost: Free to use — government marketplace; plan premiums are the real cost and depend on income · Needs: Income estimate; open-enrollment windows apply. · checked 2026-08-28
Stride (health navigation)free anchor A free navigation layer over the marketplace, built for gig workers.
Cost: Free · Needs: Nothing to browse plans. · checked 2026-08-28
Catch Their words today: "Find health, dental, and vision insurance that fits your life." NOTE: Catch has PIVOTED — its old auto-savings-benefits identity is gone from its own pages.
Cost: Plan premiums are the cost; their navigation is presented free on the pages read · Needs: An account to enroll. · checked 2026-08-28
Insure the work itself — liability, and the certificate gigs demand
Thimble By-the-job general liability with instant certificates of insurance. WHY THIS IS HERE: our directory has read hundreds of courier and contractor ads demanding things like "$300k general liability with us named as additional insured" before any work — this is the category of tool that answers that ad the same day. A customer's words on their page: after days of searching for "the perfect Certificate of Insurance ... in a couple of clicks I managed to obtain exactly what I needed."
Cost: Priced per quote; the model is the point: "coverage by the job, month, or year" — their words · Needs: Your trade and ZIP for a quote. · checked 2026-08-28
Next Insurance Small-business insurance (general liability and kin) sold online, the subscription sibling to by-the-job coverage.
Cost: Subscription policies; "$19/mo"-from figures on their pages · Needs: Your trade for a quote. · checked 2026-08-28
Allstate Ride for Hire Rideshare gap coverage — fills the space between your personal policy and the app's coverage periods.
Cost: An endorsement priced with your auto policy · Needs: An Allstate auto policy. · checked 2026-08-28
Progressive rideshare coverage cost unresolved Rideshare endorsement from a major insurer.
Cost: UNRESOLVED — their rideshare page answered 404 at two paths on 2026-08-28; the product is described across their site but we could not read its page · checked 2026-08-28
Buckle (gig auto insurer) cost unresolved Formerly a direct rideshare-driver insurer; its consumer door could not be found this round.
Cost: UNRESOLVED — buckle.com is a clothing retailer and buckleup.com now reads "Insurance Fronting Experts — Gig Insurance," a business-to-business identity (searched 2026-08-28: both domains). The consumer rideshare product could not be located on its own pages · checked 2026-08-28
Bank an income that arrives unevenly
Foundfree anchor Business banking with bookkeeping and tax tools built in, aimed at the self-employed.
Cost: Core plan $0/mo — "no required hidden fees," their words; Found Plus $315/yr and Found Pro $720/yr sit above it, 30-day trials, "keep your free Found plan" on cancel · Needs: An account; it is a financial-technology company with partner banks (their disclosures). · checked 2026-08-28
Lili Small-business banking with tax buckets and invoicing at the paid tiers.
Cost: Tiered (Basic/Pro/Smart/Premium); cashback and the tax/invoicing tools are gated to paid tiers per their own footnotes; savings APY figures stated on-page · Needs: An account. · checked 2026-08-28
Prove your income — rent an apartment, get a loan
Opolis A member-owned employment cooperative that makes you a W-2 EMPLOYEE OF THE CO-OP while you keep working for yourself — "group rates, compliant payroll, W-2 status," their words. WHY THIS IS HERE: pay stubs and W-2s are what landlords and lenders ask for, and being 1099 is what stops gig workers from renting apartments and qualifying for car loans. Nothing else in this reference touches that problem. Group health, dental and retirement ride the same membership.
Cost: Membership dues (their pages carry $97/$210-region figures); payroll runs through the co-op · Needs: Membership; your income routes through the cooperative's payroll. · checked 2026-08-28
The S-corp lever — the tax structure nobody tells 1099 workers about
THE MECHANISM, plainly: a sole proprietor pays self-employment tax on all net earnings. An LLC that elects S-corp status pays its owner a reasonable W-2 salary and can take remaining profit as distributions not subject to self-employment tax. For someone clearing real income the difference is commonly four figures a year. A THRESHOLD MATTERS — below some level of net income the payroll costs and admin outweigh the savings — and the break-even moves with tax law and your numbers, so we name that it exists rather than invent one. We are not tax advisors; this is a category to know about and ask a professional about.
Your state's Secretary of State free anchor Every formation service below files the same documents you can file yourself.
Cost: State filing fees only — forming an LLC directly with your state is the no-markup path · Needs: Your state's filing fee and forms. · checked 2026-08-28
Lettuce S-corp-in-a-box for solopreneurs: formation, payroll, quarterly taxes and books run for you. The category's consolidator — Carry (retirement platform) is joining Lettuce per Carry's own banner.
Cost: Tiers by income band (a $99/mo tier appears on their pricing page); LLC formation included at $0 + state fees on their page; "your tax savings are guaranteed" is their framing · Needs: Enough net income for the S-corp math to work — ask a professional where that line is for you. · checked 2026-08-28
ZenBusiness LLC formation service with upsell tiers.
Cost: Formation "starts at $0 + state fees" — their words; paid tiers and add-ons above · Needs: State fees regardless. · checked 2026-08-28
Northwest Registered Agent The registered-agent half of keeping an entity compliant, priced flat.
Cost: Registered agent service $125 per year flat — their page, with address/mail-scanning bundled · Needs: An entity to represent. · checked 2026-08-28
Cut what the car costs you
Upsidefree anchor Cash back on gas, groceries and dining — "earn an average 8% cash back on grocery and dining," their words, with gas offers by station.
Cost: Free app; funded by merchant offers · Needs: Their app; claim offers before you buy. · checked 2026-08-28
CarAdvisefree anchor Compare maintenance prices, book, and approve repairs at 32,000+ shops at negotiated rates.
Cost: Free to join — "Sign Up For Free," their words · Needs: An account. · checked 2026-08-28
Jerryfree anchor Compares real quotes from "100+ insurers" and "contacts repair shops on your behalf at no cost" — their words. Car insurance is most drivers' second-biggest expense.
Cost: Free — they are paid as an insurance broker · Needs: Your current policy details for comparison. · checked 2026-08-28
Mudflap cost unresolved Diesel discounts for truckers, by reputation — unread by us, so unclaimed by us.
Cost: UNRESOLVED — the site did not answer our reader on 2026-08-28 (searched: mudflapapp.com) · checked 2026-08-28
Get paid before payday — read the cost first
THE COST STORY LEADS HERE. These apps advance money against earnings, and the expedite fees and optional "tips" ARE the product — small flat fees on small advances are large costs in percentage terms, and weekly use compounds them. They are on this page because workers find them anyway; know the price of the convenience before it becomes a habit.
EarnIn "You worked today. Get paid today" — earned-wage access against hours already worked.
Cost: Advances against earned pay (figures like $150/day and up to $1,500/pay period on their pages); standard transfers slower, expedited transfers carry fees ($2.99–$3.99-class figures sighted) and optional tips · Needs: Linking your bank and earnings. · checked 2026-08-28
Beem Cash advances aimed at freelancers and gig workers.
Cost: "Up to $1,000, no credit check" — their words; access rides a subscription and instant-transfer fees per their terms · Needs: An account and income history. · checked 2026-08-28
Branch Faster payouts embedded by the companies you drive for.
Cost: Reaches workers through employers/platforms (business-to-business); worker-side costs depend on what your platform enabled · Needs: Your platform must use it. · checked 2026-08-28
You're not alone — a union for the self-employed
Freelancers Unionfree anchor "A support system for independent workers through advocacy, education, and benefits" — their words. A benefits marketplace, a tax center, a LEGAL CLINIC, and advocacy (their World's Longest Invoice tracks $13.7M+ in unpaid freelancer bills).
Cost: "Join for Free" — their words; a non-profit · Needs: Nothing. · checked 2026-08-28