Most leaders try to outrun their fear. Very few are willing to sit with it, understand it, and let it shape them in a healthier direction. In this week’s episode of Fearful Giants, I sat down with Liza Gurtin, a founder, former VC, and longtime product leader who has spent her career at the intersection of technology and human connection.

Liza was an early employee at Robinhood, helped build foundational product systems at Slack during its run to IPO, later became a VC at Matrix and Adverb, and angel-invested in over 25 early-stage companies. Today, she’s a venture-backed founder building software for modern family life, grounded in the belief that as agentic AI reshapes how work gets done, our homes deserve the same thoughtful, intelligent systems that transformed the workplace.

I met Liza at a personal development retreat a few years ago. Out of 40 people, she was the one who naturally stepped up, gathered the group, brought order to chaos. She leads with this steady intensity that feels both grounding and electric. And yet, underneath all that strength, she carries fear just like the rest of us. That’s why this conversation felt so important, because her honesty gives the rest of us permission.

Before founding her current company, Liza led core product teams at Slack, built Block Kit, scaled critical workflows millions rely on, and later invested in early-stage founders as a partner at Matrix. She studied Symbolic Systems at Stanford and has always approached technology through a deeply human lens.

“Everything is done with fear. You just gotta do it scared.”

— Liz Gurtin

In This Episode, We Talk About:

The fear of not being “enough”
Why our inner “judge” gets loud when we’re making big moves, like founding a startup
How sports shape our instincts as leaders
What good leadership feels like (and what it absolutely doesn’t)
Why vulnerability from the top sets culture more than any value statement

My Key Takeaways from this conversation with Liza Gurtin:

1. Fear doesn’t disappear with success.
If anything, Liza found that the higher she climbed, the louder her internal critic became. Success doesn’t silence fear.

2. Great leaders create clarity, not control.
The best leaders are the ones who align on outcomes and give space to create. That kind of leadership fosters a true team.

3. Naming your “judge” changes everything.
Once you stop over-identifying with your inner critic, you can actually work with it. Liza’s practice of using ‘Morning Pages’ to write from the judge’s perspective is a powerful reframing tool.

4. Leadership happens in small moments.
It’s not the big speeches. It’s the quick “yes, please share your ideas” when someone is hesitant - these are the moments that will change your company culture.

5. You don’t overcome fear - you walk with it.
This entire conversation is a reminder that no matter how high you climb, fear doesn’t disappear. Our power is in choosing creativity, meaning, and impact - even when fear doesn’t leave the room.

Whether you’re a founder, a leader, an operator, a parent, or just a human trying to lead your best life, I think you’ll find a piece of yourself in Liza’s story.

Listen to the full episode: