Before Season Two of Round Two begins, we’re revisiting an unfiltered conversation with host Jaclyn Siu and fellow founder Jason about the parts of entrepreneurship that don’t make the highlight reel.

We kept the mics hot while they unpacked the emotional side of leadership—how it feels to shut down a company, the quiet grief behind layoffs, and the shame founders carry when things don’t go as planned. Together, they reflect on what failure can teach us, how to build healthier definitions of success, and why we need more honest spaces to talk about the “in between.”

This bonus episode from Season One of Round Two is warming us up for Season Two with reflective dialogue between two founders who’ve lived it.

In this episode:

• Why founders struggle to separate self-worth from startup success
• What happens when your leadership identity starts to crumble
• How to lead and let go with empathy
• The power of community, honesty, and healing after failure

About Round Two

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

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