About Bootstrapper Media

The Company

What we are.

Bootstrapper Media is an entrepreneurship media company and education network that creates and distributes podcasts, newsletters, videos, live events, and sponsored experiences for bootstrapped founders, small business owners, exited entrepreneurs, operators, investors, and brands serving the ownership economy.

What we believe.

Business ownership changes lives. But too many people are taught how to work, not how to own. Bootstrapper Media exists to make entrepreneurship, financial literacy, and ownership easier to understand, more entertaining to learn, and more accessible to people building real businesses.

The founder.

Chris Sacchinelli is founder & CEO of Simple Holdings; author of OWNABLE and Exit with Ownership; and host of Bootstrapping to Billions. He has built three bootstrapped exits across six, seven, and eight figures, and built one of Connecticut's first AI accelerators with IBM. His first business was at age 9 — a lemonade stand. The brand's "keep it simple" philosophy traces back to that stand.

Corporate architecture.

Bootstrapper Media is a media property of Bootstrapper Capital, which is a portfolio of Simple Holdings (Trumbull, CT). The entity chain is intentional — every Bootstrapper Media property compounds the same parent network.

The property network.

• • Bootstrapper — the daily newsletter.
• • Bootstrapping to Billions — podcast and video.
• • Exited. — media and community for exited founders.
• • Bootstrapper LIVE — live events and activations.
• • The Bootstrapper Creator Network — representation for aligned owner-led properties.

How we partner.

We partner with brands, creators, and sponsors who believe more people should understand entrepreneurship, financial literacy, and ownership. We don't sell empty impressions. We build useful media experiences that earn trust. See how we work with sponsors →

Save money today. Build wealth for life.