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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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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.
Looking for guidance during your own entrepreneurial transition?
Discover Starcycle. We support founders in closing chapters and opening new ones—with empathy and clarity.
2 episodes
