Third time’s a charm

Welcome to the second edition of Too Many Tabs — my weekly thoughts on building, breaking, and learning as a founder. I’m the co-founder of Poppylist, and this newsletter is where I unpack what we’re doing behind the scenes — the messy middle of startups. No playbook, just process.

Next week, I’ll be taking paternity leave — for the third (and final 😅 ) time.

When my second child was born two years ago, I was working in the literal delivery room.

We had no team.

No real systems.

And no leverage.

At the time, Poppylist was still getting off the ground and everything ran through me or Sarah (my co-founder). If we stopped working, the business stopped moving forward.

Bootstrapping a startup and having a baby at the same time basically meant zero separation between work and life.

This time feels different — because Poppylist is different.

In the last two years, Sarah and I have focused on building more than just a product. We’ve built:

• A small but mighty team to keep the business moving forward, even when Sarah and I are not working

• Robust internal tools so the team can do things I used to handle directly in the database

• Systems and leaders that remove us as bottlenecks

And I’m going to be better about setting boundaries this time around.

No Slack on my phone. No late-night inbox checking “just in case.”

The truth is: I couldn’t take this time off without the foundation Sarah and I have worked hard to build — or without the trust I have in our team.

This feels like a milestone I didn’t see coming, but one I’m proud of.

We’re still small. We’re still learning.

But we’ve built something that can keep going — even when one of us steps away for a bit.