"Don't waste your chips on bad hands."

Dimitar Stanimiroff has been through multiple exits, some successful, some painful shutdowns. He co-founded WePal (acquired) and Heresy (shut down after 3.5 years). His biggest financial return came from joining Stack Overflow, not founding his own company.

In today's episode, I'm joined by Dimitar Stanimiroff, a seasoned SaaS founder, operator, and investor who's experienced both sides of the exit coin. After co-founding WePal and seeing it acquired, he started Heresy, raised $1M in venture funding, and ran it for 3.5 years before making the difficult decision to shut it down. He then joined Stack Overflow as an operator and helped scale it, resulting in his biggest financial return to date.

Together we unpack:

• Why "quitting on time feels like quitting too early" and the real cost of staying too long
• How to think of your entrepreneurial journey like poker chips; finite resources you can't waste
• The hard reality of shutting down a business after raising venture capital
• Why his mentor Joel Spolsky told him to quit just months after launching
• When plateauing milestones become warning signs it's time to fold

👆 If you're a founder struggling with the decision to persevere vs. pivot vs. shut down, this conversation provides a framework for making one of the hardest decisions in business.

About Dimitar Stanimiroff

Dimitar Stanimiroff is a seasoned SaaS founder, operator, and investor. He co-founded WePal (acquired) and Heresy, and helped scale Stack Overflow, Handshake, and CrossBeam to over $100M ARR. As an angel investor in B2B SaaS, he's backed PatchHQ, Lightdash, and others from pre-seed to Series A. His biggest insight: think of your time as poker chips and don't waste them on bad hands.

Connect with Dimitar Stanimiroff on LinkedIn.

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