Inspiration

About 2.7 million Canadians are self-employed (13.2% of everyone working), and almost 700,000 did digital gig work in 2024, up 44% in a single year. Without an employer, they lose paid vacation, sick days, half their CPP, and usually their benefits: about 75% of self-employed Canadians have no disability insurance, and only 36% have a dental plan. One bad week, a sickness, a new baby, or a broken oven, can mean zero income and a big bill at the same time.

Help does exist. Self-employed people can opt into EI for sickness and parental leave, but in the government's own evaluation only about a quarter of non-participants had even heard of it. The safety net is there; people just can't find it or don't know what it means for them. We built BYOB to change that.

What it does

BYOB is for anyone working without an employer's safety net: freelancers, gig workers, contractors, small business owners and new founders.

Understands any business: describe your work in plain words, in any language (it auto-detects), and BYOB builds your profile: income by season, equipment, insurance, life events.
Finds your gaps: compares you to an Ontario employee and lists what you're missing, most urgent first, each with why, concrete fixes, and a link to the official source it's based on (canada.ca, ontario.ca, WSIB) with the date it was checked.
Plans your savings: a 4% time-off fund (like employer vacation pay), a repair fund based on how risky your equipment is, lean-month warnings, and how many weeks off you're covered, before and after BYOB.
Reads your insurance policy: upload the policy you already have. BYOB works out what's covered step by step, quotes the exact clauses, lists the documents you need, gives the deadline, and drafts your claim letter. Then a recovery plan: insurance → your repair fund → your group → a backup plan. Works with no insurance too.
Support pool (optional): a small group of solo workers who pledge gifts to each other. BYOB never holds money. Gifts, not guarantees, with waiting periods, caps, and a "can we survive 3 claims at once?" check.
Burnout nudge: flags long stretches of 6-day weeks and shows how much time off your fund covers.

Example: Maya's 6-year-old bakery oven breaks ($6,000). BYOB reads her policy and works out that the insurer pays $3,500 (70% age rule → capped at $4,000 → minus a $500 deductible), quoting each clause. Her repair fund covers $500 and her group pledges $2,000.

What's new

Pieces exist: Livelii helped Canadian freelancers save toward Manulife benefits, insurers like Turvi use AI to read policies for their own claims teams, and the Netherlands has Broodfonds sickness pools. But those either sell insurance or work for the insurer. BYOB is on the worker's side: it finds the free programs you're missing, reads the policy you already have, plans your savings, and adds a community backstop, in your language, without ever selling you anything.

How we built it

Frontend: Next.js, React, TypeScript, Tailwind (Vercel)
AI server: Python + FastAPI (Render), using Google Gemini with structured outputs, so every user and every insurer's wording comes back in the same reliable format
Grounded AI: Gemini may only use a fact-checked rules file built from official government pages; every gap links to its source, and the link comes from our code, so the AI can't invent one
Maths in code, not AI: savings, equipment risk and the pool are plain, tested Python
Built for a live demo: automatic retries, backup AI models, reconnects on dropped Wi-Fi, saved answers for instant repeats, and offline fallback screens
Login (optional): Supabase with row-level security, so each user only ever sees their own data; guest mode works fully

Challenges we ran into

Gemini being overloaded and hitting free-tier limits mid-testing, which we solved with retries, backup models and caching
Keeping the AI from inventing facts: it was treating default values as truth, so we removed them and made it cite sources
Turning messy input like "busy May to October" into accurate monthly income
Making sure the app never shows a made-up insurance payout: if the AI can't read a policy, it says "try again" instead of guessing

Accomplishments that we're proud of

On our test policy, BYOB calculated the exact insurer payout ($3,500) through a 70% age rule, a $4,000 cap and a $500 deductible, quoting each clause and matching our hand-calculated answer. It works for any business, in any language, and every recommendation is traceable to an official source.

What we learned

Use AI for understanding messy language and documents, and plain code for anything that must be exact. Trust comes from showing your sources, not from sounding confident.

What's next

Real group invites for the support pool, weekly automated checks of government pages flagged for human review, more provinces beyond Ontario, forecasting from uploaded invoices, and a paid AI tier so real users' documents stay private.

Sources

Statistics Canada self-employment and gig work data (2023–2025)
Statistics Canada Labour Force Survey on benefits coverage (March 2025)
Government of Canada, Evaluation of EI Special Benefits for Self-employed Workers
canada.ca, ontario.ca and WSIB pages linked in our rules file