News + Insights

Roots Run Deep: Community at Penny Jar

Blog Posts
Feb 27, 2026

From Platform Monetization To Inbox Reality: Why Austin Chen Is Rebuilding The Deal Layer Of The Creator Economy

Portfolio News
Feb 12, 2026

Upwind raises $250M at $1.5B valuation to continue building ‘runtime’ cloud security

Portfolio News
Jan 29, 2026

Compa’s Series B: A Look Back and a Leap Forward in Compensation

Blog Posts
Jan 27, 2026

People First, Always: Celebrating Upwind’s Series B

Blog Posts
Jan 26, 2026

Upwind Raises $250 Million to Expand Cloud Security

Portfolio News
Jan 26, 2026

The Human Stack: Cashing In on Community at Our High-Stakes Holiday Evening

Blog Posts
Dec 3, 2025

Former cyber spy raises $60 million to fight AI threats

Portfolio News
Dec 2, 2025

Penny Jar Capital Welcomes Chief of Staff, Nia Pryce

Penny Jar News
Oct 29, 2025

If It’s Too Complicated, You’re Doing It Wrong

Founder Stories
Oct 2, 2025

The Courage to Show Up Anyway

Founder Stories
Oct 1, 2025

The Business She Refused to Inherit

Founder Stories
Oct 1, 2025