Emotional Rollercoaster

Leaders' emotions: The Emotional Rollercoaster of a Startup Founder

What is the reality of being a leader? What emotions are involved in leadership? How to manage difficult emotions or cope when things get tricky? What's most important when building a team? In this article, Laavu's client James Cramer shares his journey, talks about leaders' emotions and the emotional rollercoaster leading a company can feel like.

March 18, 2024
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Leaders' emotions: The Emotional Rollercoaster of a Startup Founder

The Emotional rollercoaster of a startup founder – from the highest high to the lowest low

James Cramer, an ambitious entrepreneur, built Skunkworks from scratch in 2018. James "has seen it all" – in the beginning, Skunkworks flew high, raised 5.8 million over five rounds and then, in the end, didn't make it.  Sadly, Skunkworks lasted just a couple of years – which is still more than for most of the game studios. Now James is working on a new project.

Because of his experience, James is definitely a right person to talk about the topic of leaders' emotions. In addition, he shares valuable tips on how to manage difficult emotions, based on his learnings.

“When I talk to people about Skunkworks now, one of the first things I talk about is the fact that it was a rollercoaster. It was the most intense three years that I've had in my entire life”

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The Emotional rollercoaster of a startup founder – from the highest high to the lowest low

The highest high for James was the six weeks of the global launch of merchants. He describes it as follows "It's quite an incredible feeling when you're not really sure like you have a suspicion that things are going to go well because, when you launch a mobile game, you launch it in small markets. You might launch it in six to 12 markets at the very end of the soft launch, and then when you go to the big markets like the US, UK, Germany and so on, you don't really know what's going to happen."

Every time the team increased spend, the revenue kept increasing, sometimes with a few days' delay, but it increased, nevertheless. "That was an incredible feeling", James says. "I don't know how to describe that. That makes you feel like Superman Sam's 10."

Joy

For James, the core feeling as a founder and CEO was joy. He describes it as “winning the Champions League in the World Cup all at the same time”. When one has seen several games failing, even if they strongly believed in them (and thought the player would, too), and then that one finally works, the feeling is fantastic.

At the same time, James was trying to remain humble and keep his feet on the ground.
“People would always congratulate you, but I didn’t pay too much attention to that.”

James felt super happy: finally, putting all the time and effort into building the company was paying off. He wanted to show respect to everybody supporting Skunkworks – and even downplayed some of the “stuff” at the time.

Sadness

Unfortunately, the high had to come to an end. When asking, “ what has been the lowest low you experienced as a founder and CEO?” James doesn’t hesitate: “the end of the company. That was heartbreaking, like really, really heartbreaking.”

They were functioning fine, and then out of nowhere, they weren’t. At that time, Skunkworks had 34 employees. James says that especially explaining to the employees what was happening was heartbreaking. “Like, my heart was broken, and I’m trying to break other people’s hearts by breaking the news to them.”

In addition, James explains that the end of one’s first company is made the end of it even more difficult. He had put his heart and soul into Skunkworks, and the loss felt heartbreaking, especially for this reason.

5 Stages of grief

The whole process took several months. James says it took weeks for the information received from investors to really "sink in". First, he couldn't believe what they were saying – Skunkworks had been doing so well and was the darling of one of their portfolio companies. So how could it be that now they needed to "reduce headcount significantly if wanted this company to survive"?

As mentioned, at first, James couldn't believe what was happening. He told himself stories like "the investors don't know the full story". When reality finally sank in, James went through the five stages of grief.

What James finds sad is that he was ahead with the process – by the time the other team realised what was going on, he had reached the acceptance stage already.

"It can also be a quite lonely place for the leader because you need to go through it all before the team goes through it, so the team has each other, but then as a leader, you need to kind of face it all alone and then think about how do you communicate this and how do you support the others. At the same time, you're doing the grief work yourself. It's extremely lonely, I would say."

James isolated himself from the team before he needed to break the news. He didn't want to break the team's bubble. "I was away from everybody for a long time. Most working days, I would be sitting alone hammering out emails by myself, and everybody else is in the kitchen, and I can hear people laughing and joking and stuff, and I'm thinking: they have no idea".

However, even if James tried to be discreet, some team members noticed what was happening. Afterwards, one of the first employees of Skunkworks said that as soon as they saw James starting to be away from the team, they knew.

When reflecting to his feelings now, James says he’s “over it”. The sadness is still there and sometimes there’s a period when the events are taking up space in his mind. However, this lasts only for a few hours and then he’s ready to let go.

How to cope when things get difficult

During the tough times, James used three methods to cope with the complex emotions:

  1. Physical exercise to "get it out of the system."
  2. Talking to/spending time with loved ones 
  3. Self-reflecting and processing 

Besides going for walks, hitting the gym and talking to his loved ones, James spent quite a lot of time processing and thinking. He says that he's always been well-equipped to deal with even difficult issues. "It's a process", he says. "I'm good at spending time alone and letting the thoughts play out in my mind, getting sort of my ducks in a row mentally."

During this processing time, James aimed to figure out his part in all that happened; what did he say, what did he do, how did he react, was this wrong, and most importantly, what would he do differently in the future? The goal is to learn and process what happened.

Addicted to the ups and downs

James believes feeling strongly comes naturally to founders and leaders – as they were always riding an emotional rollercoaster.

Typically, minimal resources are available when founding a new startup. At the same time, the founder must spread their wings wide across the business while keeping the goal in mind. "The model itself is inherently a rollercoaster. Not everything is going to be working all the time correctly, but you are the one that has to deal with it – all the time."

In addition, James highlights the importance of believing in the vision, even during the more challenging times.

"Your belief in what you're doing has to be unshakable. The moment you start to get some doubt, take a break. Really, step away. Let somebody else take over from it."

James describes all this as sort of an addiction. "You're addicted to that rollercoaster of emotions. Like all addictions, the more you do it, the less you feel. People interpret that as some kind of resilience, but actually, it's addiction." From his experience, one builds up a tolerance to stress, and thus, even high levels of stress start to feel normal.

Shallow LinkedIn

We asked what James thinks about the social stigma around "highs" and "lows" and if the failures are socially accepted.

James believes that social media, in particular, LinkedIn is quite shallow, with people doing high-fives and commenting like "great job, you guys are amazing". At the same time, even if everyone wants to be seen as positive, the reality is different. "As soon as the post has gone off people's news feeds, they forget about it. They aren't there to help you pick up the pieces."

"That's why we liked Laavu at Skunkworks – because we're not talking about an entrepreneurial journey, but everybody has a journey. Services like this are super valuable because not everybody has the tools mentally dig that deep."

James says that to be successful, the founder needs to have a great deal of mental strength – an ability to dig deep and get their way through the problems, because once the old problems are solved, new ones will appear, and they do that without announcing themselves.

Note to self: Build a strong, performance-driven company culture

When asked about major learnings, James mentions the importance of having a performance-driven culture in the team. James learnt that building an altruistic, supportive and friendly culture is essential, but building a performance-driven culture is also vital. How to motivate people to work towards the vision?

"I suppose motivation plays a big part, but it's also ways of working and building systems for performance.", He comments. "We didn't have a performance-driven culture. We had a very friendly culture. It was a nice place to work. Everyone got along very well, but we just didn't have that sort of performance aspect to it."

He believes building a more high-performance culture that wants to win is his next big challenge. It is not easy, though. You may need to be the "party pooper" and encourage people to push harder and learn from your mistakes to do better in the future.

"When we started the company, one of the things I said was I wanted to build a team of people who would run through walls with one another, no matter what. That they would always be there to pick each other up and support each other. We did that, and we succeeded with that, but it wasn't the type of culture where people would say, "it doesn't matter that you fail, but you can do better, let's get better, let's win"."

Tips to other entrepreneurs

Finally, James shares his tips with entrepreneurs.

-Even if you feel lonely, you are not alone – many other people feel very similar to you. James thinks leadership, in general, is quite a lonely place: it's lonely at the top.

-For your own sake, learn to dig deep, find the tools and within yourself, bring yourself through those moments.  Think of it like an addiction: you know you can sort of power through these moments because you have a goal, you have a thing that you want to achieve.

-Accept that lows are part of the ride. It's a good tip for anyone struggling with strong emotions. The biggest problem is that we try to avoid the downs: instead, one should enjoy and accept that it is part of the thing and that it's okay to feel down at times.

-Don't be afraid to play it up. Don't be scared to let your emotions go through what they need to go through in whatever period of time.

People feel quite defensive and don't want to be honest about their failures, maybe because they haven't admitted them to themselves. The paradox is that we'll only get support if we share our mistakes. If we only share the highs, the success stories, then we're only going to get praised for that.

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