In this podcast episode, three-time founder and startup advocate Jaclyn Siu discusses resilience, reinvention, and redefining failure with Daniel Ahmadizadeh, founder and CEO of Time.

About Our Guest:

Daniel Ahmadizadeh is an entrepreneur, educator, and seven-time Y Combinator applicant turned founder. Daniel’s journey spans teaching at Stanford and Columbia, consulting for early-stage founders, and navigating the emotional terrain of shutting down his YC-backed company.

In this episode, we cover:

• Why Daniel applied to Y Combinator seven times — and what happened when he finally got in
• How shutting down a company impacted his identity and mental health
• Reframing entrepreneurship as problem-solving rather than personal validation
• “Start With One” — a powerful framework for founders feeling lost or stuck
• Teaching the next generation of builders how to grow confidence and take meaningful first steps
• What Daniel is doing differently this time around

Listen now to explore the realities of entrepreneurship—where setbacks become stepping stones, and honest stories lead to powerful comebacks.

About Round Two:

Round Two, hosted by Jaclyn Siu, is dedicated to rewriting the narrative around startup setbacks, resilience, and reinvention. Subscribe wherever you get your podcasts and join the conversation online.

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When one of my startups shut down, I couldn’t talk about it.

I shrugged. I changed the subject. I avoided the story, even though that chapter shaped me more than any success ever did.

I’ve learned that people WANT to hear that story. So I gathered up some of the most inspiring founders who have walked the same path I have and invited them to share THEIR stories with you.

Round Two is the podcast I wish I had back then. A place where founders talk about the moments that broke them — and how they found the courage, clarity, and grit to build again.

Each episode spotlights a different founder who’s faced failure and still chose to come back stronger.

Because the real magic happens in Round Two!