Bonsai

Bonsai is the all-in-one business management platform Matt Nager and Matt Brown bootstrapped from San Francisco in 2016, building the tool every freelancer needs but almost no product delivers well: proposals, contracts, e-signatures, project management, time tracking, invoicing, expenses, and taxes — all connected, all in one place. The insight was that freelancers hate switching between 6 different tools (a contract tool, an invoicing tool, a time tracker, a project manager) and lose data in the handoffs between them. Bonsai grew to $10M+ ARR by making the entire workflow from "signed proposal" to "paid invoice" automatic: a client accepts a proposal → Bonsai auto-generates the contract → client signs electronically → project is created → time tracked against the project → invoice generated from timesheet → client pays online. Each step is one click from the previous. The platform also handles quarterly tax estimates (US-specific, calculating self-employment tax owed) — a feature that makes Bonsai feel like a business partner rather than just software.