A Founder’s Summer Holiday

Blog #5
This summer, I stepped back from the day-to-day to work on the business, here’s a breakdown of the three big questions I answered.

A nice work spot for the afternoon in Lisbon, mixed with some local restaurant research!

Context

Before diving into the three questions I spent the summer exploring, it’s worth sharing where my head was at after our events wrapped up, which led to more time being spent working on the business instead of in it.

The stress of the event period hit me all at once. In the following week, my brain was scrambled. The weird thing was that I could still work hard, I just couldn’t think about events at all, the idea of organising another one gave me a headache, I’d never felt anything like it!

It sounds ridiculous now, but it took a couple of months before I could even look at our event plans again. Only recently have I started to feel genuinely excited as we begin shaping next year’s calendar.

As a result, the period over summer gave me space to reflect and led me to three questions that have clarified where we’re heading and what it’ll take to get there. Here, I break down how I went about answering the questions.

Where do we take the business?

This was a big one. I hadn’t really asked it before starting the company - I just gave it a go and figured I’d see where it led. Having three months to think deeply about direction and purpose was invaluable, and I hope it pays off long-term.

To answer this question, I spent a lot of time wandering, literally and mentally, asking myself what I want from this and why I’m doing it. Clarifying those two things took time.

My favourite note book!

My favourite pastime is dreaming up ideas, running away with them, then working out how I can actually bring them to life. So naturally, this summer involved hundreds of different ideas, directions, and visions for the business. A polite suggestion from my mentor that perhaps I should focus on the cricket events for the time being jolted me back into reality!

I probably spent too much time working on the business instead of in it. Dreaming up billion-pound ideas was, unsurprisingly, more fun than writing an event operations manual. But, hearing Jeff Bezos talk about the value of “wandering” at Italian Tech Week reminded me that this kind of thinking has its place.

And it worked. I now feel crystal clear on our direction and vision - and more excited than ever about what we’re building. I’ll go into what my vision is down the line.

What do I need to learn about running a business?

This question reignited my curiosity for the first time since A-level history (something my university degree never quite managed). It’s now become a bit of an obsession.

My favourite episode: Illustrates so well the importance of building towards something greater than your company.

My favourite way to learn is by studying great founders and seeing what I can apply to my own journey.  I discovered Founders podcast back in the Spring, where David Senra studies history's greatest entrepreneurs, completely changing my life. Many friends who listen have said the same thing. This became the soundtrack of my summer, opening my eyes up to what makes these founders/businesses great,  how they think, and the common themes.

I also rediscovered my love of books, something I didn't expect to see on my 2025 bingo card. Autobiographies by Michael Dell, Richard Branson, and Phil Knight, along with the classic "Good to Great," were standouts. Not groundbreaking picks, but essential reads nonetheless.

One uncomfortable realisation: I need to identify my weaknesses and build around them. It’s not the most enjoyable process, especially when the list is long, but it will allow me to focus on where I can actually add value in time.

Finally, personal development has become a major focus. As cringey as it sounds, working out how to be the best version of myself each day through habits, routines, and reflection has transformed my productivity, knowledge & skills. It’s a process that’s evolved over time, but really clicked in the last month.

What do we need to change going forward?

If there’s one lesson I’m taking into the next phase, it’s the importance of delegation, something that many hours of learning about Branson will quickly teach anyone!

Now that I’ve clarified the vision, delegation will be essential. One simply can’t build something meaningful alone.

I quickly learned that running an event without delegating is tough, let alone running a business. It wasn’t that I didn’t want to delegate, I just didn’t have the knowledge of how best to!

So I spent the latter part of the summer exploring how to hand off parts of the business that don’t need me, freeing me up to focus on the areas where I can add value.

This winter, we’re documenting everything: playbooks, manuals, how-to guides, etc, as we look to get the business to the position where it would be able to run without me. It’s one of those obvious lessons you only truly learn through experience.

Final Thoughts

The biggest takeaway from answering these questions this summer? A far deeper understanding of what we’re building and what it’ll take to get there.

Avoiding the same post-event burnout is priority number one. That means creating a sustainable event season and embedding everything I’ve learned into our operations. Combined with a renewed focus on product and brand, we’re positioning ourselves to earn the right to take the next step toward our vision.