When to walk away, with Sam Garven

What happens when the bravest decision a founder can make is to stop - and how do you know when it’s time to let go of the thing you’ve built?

In this episode of Flip the Focus, Jen and Producer Nico sit down with Sam Garven, co-founder of AI HR platform Hello Canopy, to talk about the decision to wind down the business and what happens when the founder journey doesn’t end the way you imagined.

Sam talks about the emotional gymnastics of closing a startup; moving through the decision as a solo founder after her co-founder stepped into an advisory role; and the signals that helped her pressure-test whether to keep going. She shares how customer feedback and investor interest were encouraging, while economic conditions, changing HR budgets, market uncertainty and her own financial reality told a more complicated story.

You’ll hear Sam talk about the implications of taking venture capital, hiring a team and committing to a growth trajectory when you’re no longer certain you can deliver the upside investors expect. She explains why founders need to think carefully about the decisions they’re making today—and where those decisions could leave them, their employees and their families in one, two or three years.

Sam also reflects on the fear and shame attached to closing a business, why she chose to be public about winding down Hello Canopy, and the overwhelming response from the startup community that helped her reframe the experience. She challenges the idea that closing a company is the same as failing, and asks whether we need a different definition for a journey that has changed who you are and what you can do.

For anyone considering a career change, Sam shares what it feels like to lose the identity you’ve built around a company, and how she began working out what comes next. She talks about taking time away from the internet, resisting the pressure to immediately sprint into another opportunity, and rewriting her résumé to identify the skills she developed as a founder.

It’s about making pragmatic decisions in the middle of uncertainty, recognising when persistence becomes pressure, and understanding that the skills you build in one chapter can travel with you into the next. Because sometimes success isn’t about making the company work at any cost. Sometimes it’s about seeing the signals clearly, taking responsibility for the people involved and having the courage to change direction.

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This is Sam’s second conversation with Flip the Focus, and a very different chapter in the Hello Canopy story.