“Can a construction estimating tool become the financial operating system for residential contractors?”
Founded 2016 as CostCertified, an estimating tool for residential contractors. Following Y Combinator in 2021, the company rebranded to Bolster and expanded from estimating into an end-to-end construction OS covering CRM, project management, presentations, and — critically for embedded finance — payments, business accounts, and (in roadmap) capital and corporate cards. The strategy is a classic vertical SaaS 'own the money layer' play: use estimating as the wedge, then monetize contractor cash flow via payments (Adyen) and lending.