June 26, 2025
At Calm/Storm, we often say the startup journey feels like navigating a storm. From overcoming the hurdles of fundraising to pivots, few things prepare founders for the challenges that come up along the way. That is why, twice a year we host the Calm/Storm Academy: our private, portfolio-only founder event. Here, founders don’t just talk about metrics or headlines, they talk about the real stuff. The human and unfiltered lessons that only come from living it. For a few hours of online honesty we hold conversations with different founders about fundraising, pivots and what it is actually like to build something from scratch.
This quarter our Academy brought together founders from across our community, each bringing their own raw and honest reflections. Among them was our Supporting Partner, Nora Blum (co-founder of Selfapy, exited) and our portfolio founders Sebastian Gruber (co-founder of hi.health, exited), Mo Chachin (Founder of Twain) and Sachin Raoul (co-founder of Raspberry Circle).
During our Acadmey, these seasoned sailors - founders - share the lessons they’ve learned from navigating the stormy seas of startup life. They speak openly about how they’ve weathered challenges, and often, how they’ve learned not just to calm the storm, but to embrace it. But what do these sessions look like in action?
We usually think founders leave only after an exit - but what happens when they step down before?
What does one experience leaving a company before the exit? We spoke about the early days of cracking the DiGA system, and how building a good team is one of the keys to success. But also, reflecting on why stepping aside might allow a company to move forward faster.
It wasn’t just a conversation about company-building, it was a deep dive into understanding company dynamics in time and understanding the needs. At some point, the conclusion was made that the company required a more professionalized structure to keep scaling at speed. Something rarely talked about in the ecosystem, but sometimes necessary.
We heard the story of successfully building hi.health which merged with Pliant. The deal made strategic sense - but how does it feel to go from founder to being part of a much bigger team?
The transition was a completely new experience and it brought new challenges: legal hurdles, cultural shifts, etc. but joining a larger player also brought a fresh perspective and room for professional growth.
And because the merger was with another startup, it still felt dynamic, the culture remained fast-paced and familiar. Big deals are never just about strategy; they’re also about endurance, empathy and finding the right rhythm in something new.
Our final session brought together remarkable founders who have experienced the hurdles of pivoting several times but also achieved huge milestones like being backed by Sequoia.
One of the toughest decisions a founder can face is whether to pivot or walk away. We heard firsthand stories, including a journey that began as a relationship therapy app and evolved into a creative app studio, a testament to the resilience and adaptability that early-stage founders often need.
We also explored what it takes to navigate those in-between moments: when traction is elusive, fundraising is tough, and yet somehow, through persistence and clarity, you break through and catch the attention of world-class investors.
In a world where startup life is often glamorised, it was a powerful reminder that the best advice doesn’t come from perfect slides; it comes from founders who’ve been through the storm and are still standing.
Besides our annual portfolio days - Storm Days - we’ve built something distinctive: an ongoing community. A community centered around honest conversations and mutual support. That’s why our academies are important, we try to strip away the noise and create a space where founders can talk about what’s really going on, the good, the bad and the uncomfortable.
After all, it’s easy to feel alone in the chaos. But when founders gather, we realize: everyone’s in the storm. The trick is to navigate it together.
