How Stella Garber Raised $5 Million

And why you might never have to write a todo list again

Author

Michael Houck
March 15, 2025

Hey y’all — what would you do different with your second startup?

Stella Garber shut down her first company to lead the marketing team at Trello as one of their first 15 employees. After scaling the company to a $425M exit, powered by a pioneering product-led growth strategy (before PLG was even a term), she’s back as a founder for a second time.

Her new product, Hoop, is an AI task manager that keeps you from ever having to write a todo list again. I’ve been using it for the last few weeks and it’s the first productivity tool that might get me out of Apple Notes and Slack Reminders for good.

We caught up this week to chat about why she decided to join Trello, what she learned from hypergrowth that she’s applying now, where the opportunities with AI really are right now, and why she firmly stands behind remote work even as many big companies are calling employees back into the office.

Here’s our full convo:

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Trello Journey & Early Growth

  • (00:00) — Intro

  • (01:48) — How Stella became an early Trello team member

  • (03:27) — Marketing changes during Trello’s growth

  • (07:28) — Trello’s marketing success & applications to Hoop

Marketing & Product Growth

  • (11:07) — Marketing from a user-centric lens

  • (12:45) — Unique approach to organic growth

  • (14:06) — AI’s impact on product growth

  • (15:55) — Product taste

Pivoting

  • (17:27) — The future of productivity & Hoop

  • (21:32) — Pivoting after ChatGPT’s launch

  • (24:51) — The conflicting pivot advice

  • (26:15) — When to know you need to pivot

Startups & Launch Tips

  • (29:14) — Transitioning from founder to an early team member

  • (32:38) — Successful Product Hunt launch tips

Remote Work & Team Dynamics

  • (37:11) — Remote work & 4-day work week

  • (42:08) — Asynchronous remote work

  • (44:41) — “Burstiness”

  • (47:41) — How to create a successful remote team

Rapid Fire

  • (52:51) — Who is one investor you’d recommend?

  • (53:28) — One thing you’d change about startups?

  • (55:55) — Advice for first-time founders?

  • (56:34) — Something you believe that most disagree with?

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