Brett Calhoun

Mar 12, 2026

3 min

Why We Invested in Bolster

Brett Calhoun

Mar 12, 2026

3 min

Why We Invested in Bolster

Residential contractors build and renovate the homes people live in, yet the software they rely on often looks nothing like the tools used in modern businesses. Many contractors still manage projects with spreadsheets, static PDF estimates, scattered text messages, and generic payment tools that were never designed for construction workflows. Even great builders lose time and margin simply because the back office is fragmented.

Mike Bignold experienced this firsthand while running a contracting company with his brother in Calgary. Estimates were slow to prepare, customers struggled to understand options, and payments were difficult to manage across multiple systems. Mike began building software to solve the quoting problem first, creating interactive estimates that allowed homeowners to see pricing changes instantly when selecting upgrades. Over time that tool evolved into Bolster, a platform that connects the entire lifecycle of a construction project.

Today Bolster helps contractors generate proposals, manage projects, and collect payments in a single system. The company went through Y Combinator (S21) and has grown to thousands of contractors on the platform. Recently, Bolster made a major shift toward a freemium, product-led model with embedded payments. That pivot is already showing strong results. 

Customer acquisition costs have dropped significantly and retention is strongest among contractors who process payments through the platform. Bolster is now approaching the moment where software adoption and financial services reinforce each other.

The Opportunity

  • Residential remodeling is a $400B+ market in the United States alone.

  • Millions of contractors still rely on spreadsheets, PDFs, and manual workflows.

  • Construction remains one of the least digitized major industries, with legacy tools that are expensive and difficult to adopt.

  • Bolster’s freemium model removes friction.

  • Embedded payments create a new revenue layer as project dollars flow through the platform.

  • The platform has already processed over $200M in construction project volume.

What Bolster Actually Builds

  • Interactive construction estimates that homeowners can explore and customize.

  • A single workflow connecting estimates, scheduling, budgets, and change orders.

  • A proprietary cost engine powered by 100M+ construction cost data points.

  • Built-in payments designed for construction milestones and faster cash flow.

  • Business accounts and contractor cards that connect spending to project budgets.

  • A system of record for contractors from first quote to final payment.



Contractors need software that simplifies how projects are sold, managed, and paid for. Bolster is building that operating layer for residential construction. By combining workflow software with embedded financial services, the company turns everyday contractor activity into a scalable platform. We are excited to back Mike and the Bolster team as they build the infrastructure for modern construction businesses.

Build with us in any climate.

Start your building journey with a team that appreciates the struggle

Build with us in any climate.

Start your building journey with a team that appreciates the struggle

Build with us in any climate.

Start your building journey with a team that appreciates the struggle