Founders are building in the most competitive environment in decades.

So if every hour counts, why spend three days away from your startup?

Every successful startup ecosystem has been built on dense networks of founders who share strategies, solve problems together, and compound each other's advantages.

But many founders still default to building in isolation.

This matters more than most people realise. The difference between a good founder and a great one often comes down to pattern recognition.

• How fast can you spot the warning signs of a bad hire?
• Which growth tactics actually work at your stage?
• When should you pivot versus push through?

Typically, these are insights already gleaned by other founders who've lived through the same problems.

If Europe is going to produce its first trillion-dollar company, we need to change the culture. We need founders who think bigger and support each other through the inevitable chaos of scaling.

As a fund led by founders, we know that rarely happens in Slack channels or online.

We run a founders retreat for exactly this reason.

This year we gathered more than 100 of our founders at Campus La Mola in Spain, with the entire Cherry team, for three days.

The retreat reinforced why we believe these are one of the highest-leverage investments any fund can make.

The magic happens when founders talk to each other. But creating the conditions for that magic requires more intention than it appears.

What Happened (And How We Designed For It)

The core challenge in retreat planning is balancing structured content with candid founder interactions. Our goal of the retreat is for founders to connect with each other, and we believe that happens best in the unstructured time, so we design the retreat with that goal.

Content that creates conversation

The best conversations often start with "what did you think about X”

When building an agenda, we think hard about what content to deliver to avoid generic startup talks that can be serviced by other events.

To do this, we brought in leaders of some of the fastest growing startups in Europe who understand the roller coaster of building a company in today’s environment, and who have wrestled with many of the same challenges our founders are facing:

• Oscar Pierre, co-founder and CEO of Glovo, spoke about hypergrowth culture and navigating rapid scaling.
• Joel Hellermark, founder and CEO of Sana, talked about how to think about defensibility in AI, as well as how to balance AI automation with human agency.
• Hugo Rayne, GTM at ElevenLabs, discussed where infrastructure ends and application begins, and how to approach team building - from hiring to org design.

We also heard from experienced operators in our portfolio like Mirko Novakovic from Dash0, Thibuat Ceyrolle from Aries, and Philipp Povel from Mondu. They shared successes from companies further ahead, while also being open about mistakes they made along the way, and the lessons they've learned. Their candor created a safe space for all our founders to discuss the challenges they face.

Building connections across the team

We bring everyone from Cherry too!

We believe our founders benefit from connecting with everyone, not just investors.

As a fund we bring in first-hand operator experience across all our functions. Each Cherry team member - whether partner or platform specialist - brings insights from their past experience as well as what they are currently seeing in their specialist sector of the market (investment verticals, Communications, HR, Talent, etc). These cross-team connections are really important to the culture we are building at Cherry, and help make everyone more effective.

Scheduling for real conversations

We scheduled deliberate downtime because founders need time to reflect on content, connect with peers, and completely switch off from work. This balance is essential but harder to achieve than most realize.

We hosted workshops and deep dives into key topics we know are top of mind for many founders and their teams: storytelling and brand building, fundraising, preparing for an exit, hiring the best, adding value through AI, and sales and scaling strategies.

These workshops led by experts from the Cherry network served as a catalyst for connections and conversations during meals, in the swimming pool, or over a friendly table tennis match. The vibes for this year’s retreat were centered around radical candor. Everyone had open, honest conversations both on and off the stage, and it created a special atmosphere to talk about the challenges big and small, while sharing solutions.

Building a Culture of Thinking Bigger

A big part of the retreat is creating the culture we want at Cherry and that we want our portfolio teams to embody. Our focus is building global companies in Europe, and bringing founders together is our chance to shape how that culture develops.

Shifting the European narrative

We see that building in Europe can mentally come with a lot of baggage because you're going into it knowing that big Silicon Valley firms and big Silicon Valley entrepreneurs think of you as the little guys.

This year’s retreat was designed to counter this mindset.

Culturally, European founders are often understated. We underplay successes and don't celebrate wins enough. If you look at the global top 10 companies, 8/10 are from the US. None of them are from Europe. These cultural tendencies directly impact how founders think about their potential.

At the retreat we wanted to celebrate portfolio company successes while helping them build and think bigger.

Celebrating wins, not downplaying them

We believe Europe is the place to build the next trillion-dollar company. We have the capital, we have the talent, and we want to support the ambition level. The retreat reinforced this message across every session.

Peer influence has a big impact on this. We encouraged founders to think: “how can I become a category leader in this segment?” rather than “how can I be a dominant player in this small region that I'm operating in?”

We also heard from Cherry founders who understand that sometimes global ambition means thinking out of the box - or even out of this world as in the case of Dana Baki from the Exploration Company, who talked about "building across borders" and developing internationally while Joana Cartocci from Robeauté talked about "building to address patients all over the world."

For Cherry, global ambition means being bold, being brave, and sometimes being contrarian, but with an incredibly high drive to prove people wrong. The retreat created space for founders to articulate these bigger visions amongst a group of the equally ambitious, away from the stereotypical European tendency to hedge or downplay.

Beyond the retreat

Our goal is for this culture shift to extend beyond three days in Spain.

We want founders celebrating each other's wins, energised about tackling global markets, and pushing for bigger visions. We know that relationships between founders is a way to do this, as building non consensus or bold visions can be very isolating.

As partners we felt this as founders, and use the retreat to combat this. This is partially why a key role of the Cherry team at this retreat is actually getting out of the way! The magic happens when you put ambitious people together.

Our job is creating the conditions where that European culture of bold global thinking becomes the default, and events like these reinforce our belief that we’re in the right place at the right time. We look forward to continue supporting the incredible founders and teams in the Cherry portfolio as they tackle some of the world’s biggest problems - and we know they’re only just getting started.