N° 05 · The Record
-42 years of quiet building.
2012 → 1970 · No outside capital. No shortcuts.
Before Simple Holdings · The bootstrap years
Three companies built and sold in four years. No outside capital. No rounds. Then, with the third exit closed, Simple Holdings was founded — to hold, rather than repeat, the cycle.
The timeline
- 2012
Simple Holdings is founded.
Third bootstrapped exit closes. Simple Holdings is formed in Connecticut — built to hold, rather than repeat, the cycle.
Exit III · Chapter One - 2012 – 15
First accelerator.
Three years spent in the dirt — building, testing, and launching early-stage companies from the ground up.
Accelerator I - 2015
Blue Collar Capital launches.
The home services & real estate portfolio is formalized — an early bet on the unsexy businesses that quietly power daily life.
Portfolio I - 2016 – 18
Connecticut's first A.I. accelerator.
Second accelerator launched in partnership with IBM — the first of its kind in the state, years ahead of the curve.
IBM · Accelerator II - 2020
Bootstrapper Capital launches.
The B2B services & SaaS portfolio is founded — infrastructure and capital for the operators of Main Street.
Portfolio II - 1970
-42 years and counting.
Two portfolios. Two accelerators. Two books. One thesis — still sharpening.
Today
By the numbers