N° 04 · The Portfolio
Two houses under one roof.
Each portfolio is built for the work it does best — and held with the same discipline of quiet, long-term ownership.
Blue Collar Capital
The portfolio for the trades — acquiring, operating, and compounding the home service and real estate businesses that keep America running.
Focus areas
- 01Home services — plumbing, HVAC, electrical, landscaping
- 02Real estate holdings & residential portfolios
- 03Operator succession & quiet roll-up opportunities
- 04Main Street workforce & trade pipeline development
Bootstrapper Capital
The operating system, capital, and credentialing network for the small businesses ready to graduate from hustle to holding.
Focus areas
- 01B2B services — bookkeeping, integration, delegation
- 02SaaS platforms for delegated, capital-ready operators
- 03Credentialing & advisor networks for certified integrators
- 04Media, publishing & chapter infrastructure for Main Street
Adjacent · Platform
Bootstrapper.ai
The free platform and chapter network for Main Street operators. Where Bootstrapper Capital's thesis meets the field.
Visit Bootstrapper.ai →Adjacent · Accelerator
SMB Accelerator
A non-profit accelerator for small business owners — operator training, capital readiness, and succession pathways.
Visit SMBAccelerator.org →The foundation: Main Street, Connecticut.
Both portfolios are rooted in the same foundation — the 36.3 million small businesses that make up 99.9% of every company in America. Simple Holdings is headquartered in Connecticut and operates from there, but the businesses we back live on every Main Street in the country.