We Ran A CEO Bootcamp On A Remote Island in Finland

(and no one was murdered!)

What happens when you gather 12 ambitious founders on a remote private island in the Finnish archipelago for 3 days near the summer solstice? It’s either a Fourth Box bootcamp of intense learning or the ominous start of a cult murder mystery.

Over the past few years my friends Clint and Marten from MySQL and I have mentored dozens of founder / CEOs as they build exciting startups in open source, SaaS and cyber security. This spring we decided to run a 3 day bootcamp for top-notch CEOs on a remote private island in the Finnish archipelago. We even shared the storied origins of the Fourth Box.*

It took a leap of faith that we could get a select group of venture-backed CEOs to travel to a remote location and secure sponsorship from top-tier VCs so that we would not lose our shirts. I am grateful to Benchmark Capital, Index Ventures, LifeLine Ventures and Scale Venture Partners for their timely sponsorship and nominations.

Until I stepped off the boat and onto Fagerholm island and met all of our CEO participants in person, there was still some doubt in my mind that we could pull this off. So much of an event’s success depends on the personalities and participation of the attendees. In this respect, our first cohort was superb. They were self-aware, engaged, ready to share their challenges and eager to learn.

Did it work?

Yes, absolutely! But that’s just my opinion as one of the organizers. More importantly, we exceeded the expectations of the participants and delivered real value.

We asked the participants to rate the experience on a scale of 1-5 :

• The FourthBox CEO bootcamp was a good use of my time. (Score 4.875)

• I would recommend the CEO bootcamp to other CEOs of similar companies. (Score 4.75)

We asked participants to share feedback on what they learned that they can apply in their company. Here are a few of the comments (slightly paraphrased):

• I was impressed how much people opened up. Most valuable for me was when we broke off in smaller groups and discussed our specific challenges. I learned how others are running their executive team meetings and this gave me new ideas I can put into practice.

• I learned some good ideas on how to run internal QBRs with sales, marketing and product to review deals we won or lost. This will help us increase the feedback from sales into the product team.

• It was interesting to hear how other companies are using AI internally. It was valuable to take a step back and reflect on this.

• Lots of reflection on my own leadership style from exposure to peers.

• I learned ways to enable my team to step up as leaders so I can focus on the most important items for the company.

• Good take aways to create more urgency in the team.

• I just talked to my head of people ops and we will experiment with some of ideas I stole to improve internal feedback.

We also asked what should we keep or do more of:

• The location was amazing. I think that environment was critical for changing the typical performative founder persona.

• I would keep the location exotic as it makes it easier to learn new things. I would also keep focus on workshop / discussion style rather than lectures.

And some areas that we could improve:

• I wanted to hear more from coaches and long-time CEOs who had done it before.

• It would be good to be able to sign up for a 1:1 on a topic with a specific coach.

• I’d recommend a more narrow range of companies in terms of funding and revenue. I learned the most in discussions with founders at similar stages.

It was an interesting, high-intensity approach to mentoring. While everyone left excited (and probably exhausted) the real test comes in the weeks, months and years that follow. It’s easy to go to an offsite meeting and come away with dozens of ideas. But it takes discipline to apply new techniques and best practices to improve your own performance and that of the team. We will be following up with the participants next month to help with that process.

To me there were a few key takeaways that made the event successful:

• Though it was hard to get to, the remote location contributed to the high level of engagement of participants. There were no distractions, and no other people on the island —only FourthBox participants and Fagerholm staff. We were in close quarters, sharing meals, saunas and sleeping quarters from sunrise 4am to sunset 11pm. You could not achieve the same level of openness and engagement in a hotel in Napa.

• The participants were chosen in part for their humility and willingness to learn. This was not the stereotypical Silicon Valley alpha male CEO group. We had a diverse set of CEOs (9 men / 3 women, 6 from the US / 6 from Europe) which helped keep things balanced and open. There was also a wide spread in the maturity of the companies from pre-product market/fit (sub $1m) to $50m in ARR. In retrospect that was too broad a range and we frequently broke into subgroups based on size / maturity.

• We had a high ratio of mentors (3 men, 2 women executives) each with different areas of expertise.

• We had a lightly structured program with designated topics and leaders. This enabled us to kick off discussions and then zero in on the topics the founders wanted help with. We were also able to pivot (“pivot!”) when necessary.

• There were a couple of hours of down time each afternoon enabling people to catch up on email, phone calls, seek one-on-one meetings, go kayaking, relax or engage in other activities.

• There were no board members, investors or other employees involved, which enabled people to open up more than they might otherwise.

I hope that we will do this again next year. There are definitely improvements we can make to get more in depth, practical discussions. But considering this was our first time running a CEO bootcamp, I think we did quite well.

And of course, mentoring is not a one-way street. All of us, including coaches, learned from each other. It’s interesting to hear how a younger generation of founders think about technology, business and the world. This is the first large group of “AI native” founders that I’ve worked with and their ambition and creative drive is inspiring.

Perhaps most gratifying was the feedback from one of the attendees:

• I’d love to pay it forward some day!

There is no greater demonstration of leadership than planting ideas that others make their own.

(*) The legend of the Fourth Box was revealed in a secret ceremony on the final evening after much partaking of alcohol, saunas and cold plunges. But if you really want to learn that story, you’ll have to get nominated to join our next cohort.

I am grateful to Clint, who convinced us to hold the event in Finland and to Marten who found a wonderful former coastguard island in which to host our inaugural event. The location was a challenge, but it was the catalyst for opening people up to new ideas.

I also want to thank our guest mentors Anna Binder and Kelly Battles who brought creativity and passion to topics that many founders struggle with around building a strong culture and creating accountability. Also kudos to our local host, Alto University undergraduate Casimir Rönnlöf who made sure everyone made it to the island and had a first class experience.