Settle

Software that automates contractor onboarding and 1099 payouts for home-services marketplaces. Handles everything from W-9 collection and identity verification to same-day ACH disbursements and year-end 1099 filing. The payout problem is actually a compliance and data problem disguised as a payments problem. Most fintech tools focus on the money movement layer, but the real friction is upstream — getting a valid W-9, verifying contractor identity, and ensuring accurate 1099 filing at year-end. If the data is dirty, payouts fail or the marketplace faces IRS penalties. Settle built the onboarding and compliance layer first, not just the payment rail. Five years running payments ops at a gig marketplace where Diego rebuilt the entire contractor payout infrastructure from scratch, scaling it to 40k+ contractors weekly. He owned the vendor relationships, compliance workflows, and reconciliation systems end to end. He saw the same onboarding-and-payout pain across every home-services marketplace he talked to, which is what made him start Settle. Three things converged: the IRS tightened 1099-K reporting thresholds starting 2024, forcing every marketplace to get contractor data clean or face penalties; the home-services category exploded post-COVID with hundreds of mid-size marketplaces that lack payments infrastructure; and modern banking APIs finally make same-day ACH disbursements possible without being a licensed money transmitter. A year ago regulatory pressure wasn't there, the market wasn't this big, and the infrastructure wasn't this accessible.