The 1099 Engineer's Finance Stack

Nobody warns you about the operational overhead of independent work. Invoicing, taxes, bookkeeping, contracts, insurance - the meta-work eats your week if you don't automate. This is what I run.

When I left the bank, the part I underestimated was running myself as a business. Here's the stack that keeps it lightweight.

Invoicing & contracts

• Stripe Atlas + Stripe Invoicing. Setup is one weekend. Recurring invoicing for retainer clients is automatic.
• HelloSign or Docusign for contracts. I have three contract templates: project, retainer, and advisory. Re-using them is 95% of contract work.

Bookkeeping

• QuickBooks Self-Employed in the early days. Switched to Xero when I crossed multiple-currencies + expense management.
• Wise for receiving international payments without bleeding 4% on FX.

Taxes

• A real accountant. Not negotiable. The cost is worth it. I use one specifically familiar with software contractors.
• I make quarterly tax payments. I keep 25-30% of every invoice in a separate "tax" account so the bill never surprises me.

Insurance

• Professional indemnity insurance. Required by most enterprise clients before they'll engage. Renewable annually.
• Equipment insurance if you'd be hosed by a stolen laptop.

Legal

• I have one lawyer on retainer for an annual flat fee, who reviews contract changes and answers IP questions. Worth every penny.

Productivity

• Cron or Notion for tasks. I tried fancy tools, ended up with a single Notion database called "Active Engagements."
• Cal.com for scheduling - link is cal.com/sree-vardhan-tsn0pn.
• Linear for personal tracking on each engagement.

Communications

• Front for shared inbox if I bring in collaborators
• Slack Connect for client channels (one channel per client)
• Loom for async demos and explanations - saves hours of meetings

What I deliberately don't have

• A CRM. I have <50 active relationships at any time. Spreadsheet works.
• A website builder. I built srivvs.com myself, because that's also marketing my work.
• Project management software bigger than Linear. I tried Asana, Jira, ClickUp. None justified the overhead vs. Linear or Notion.

The discipline that matters most

Time-track every billable hour. I use Toggl. Even on flat-fee projects. Two reasons: (1) you learn how long things actually take, which makes future quoting more accurate; (2) you have evidence if a client questions an invoice.

The stack matters less than the discipline. Pick what you'll actually use.

References

• Stripe Atlas
• Cal.com
• Linear