What Keeps these Five CEOs Awake at Night?


Here's how they ease their minds.

Robin Gadsby, CEO of Forever Beta

Robin Gadsby, CEO of Forever Beta

Do you wake up in the middle of the night with your mind whirring, worrying or buzzing with big plans for, or crushing concerns about, your company? You’re not alone. According to a survey conducted by Yell Business, 66 per cent of business owners say that they’re kept awake at night by said worries, with paying bills, generating profit and acquiring new customers topping their reasons for tossing and turning. We asked five CEOs to share their midnight thoughts – and how they tackle them to safeguard their sleep.

“Why aren’t my staff engaged?”
Alan Crabbe, CEO of Pozible

“The main thing that keeps me up at night is when I feel like a team member is becoming disengaged with our goals,” says Alan. “I will lay awake when something is getting in the way of my team meeting their target.”

With more than 12,000 projects launched through the platform, and pledges coming in from 105 different countries, Pozible has grown from a two-founder operation to a team of 10. In that time, Alan’s worries have shifted from cash flow and technical issues to company culture.

“Honest and transparent has generally worked for our team,” he says. “If I have concerns I try to resolve things… right away. I typically send staff meeting invites at all times of the day and night.”

He also fights fatigue with endorphins. “I’ll get up early and go for a run,” he says. “For me, it’s the first small step to resolving a problem.”

“How can I make my clients trust me?”
Robin Gadsby, CEO of Forever Beta

With big-ticket clients like Google and British grocery chain Co-Op on his roster, this founder loses sleep over the need to act quickly, which isn’t always easy.

“If something is disrupting a client’s business sector, we want to help them by moving quickly, testing and developing a new counter proposition,” says Robin, who heads up creative communications company Forever Beta.

“But, most of the businesses we work with are unable to shift quickly, both from a business and cultural perspective. I lay awake at night working out the best way to take them on a journey where they feel comfortable to experiment.”

Safeguarding his own company culture also makes his mind whir at midnight.

“Ensuring that our culture promotes the best autonomy, experimentation and empowerment is a constant battle against sleep at night,” he says.

He finds that mindfulness techniques help him drift off. “When I’m at home, I try to put away things that will pull my mind away from home. I basically create thresholds for myself where I stop doing one thing – working – and start doing another – rest.”

Keri Kitay, CEO of All I Sea active swimwear

Keri Kitay, CEO of All I Sea active swimwear

“Is my startup sustainable enough?”
Keri Kitay, CEO of All I Sea active swimwear

Having co-founded All I Sea with Leisel Jones, Keri Kitay doesn’t lie awake worrying about the look of her latest collection, so much as how to reduce its environmental footprint.

“I love my sleep but, since starting All I Sea, my mind constantly races at a million miles an hour, which often keeps me awake at night,” she says. “I’ll be up researching fabrics, new technologies, athletes and stockists around the globe. That is the fun stuff.” But what keeps this entrepreneur awake most frequently is far more sobering.

“After producing our first collection, I realised how much producing apparel can impact our environment,” she says. “We have dedicated our next collection to begin the process of implementing recycled fabrics and packaging.” This means burning the midnight oil to research fabrics, biodegradable polybags and how to make it all work financially.

“My strategies to a good night’s sleep involve a good daytime routine,” says Keri. “This means, without fail, every morning I begin my day with a training session. Meditation is another saviour, and I use detox saunas to quieten my thoughts. I take magnesium every night – it relaxes my mind and muscles.”

“What if I wake up to a crisis?”
Oli Wheeler, CEO of THRSXTY

With 25 years in the PR industry, including 18 as right-hand man to iconic publicist Matthew Freud, Oli Wheeler says disrupted sleep is the norm for him.

Recalling his pre-internet days at Freud Communications, where much of his work was around reputation management, Oli admits that he would go to sleep every night worrying about how a story he had worked on that day would be reported in the morning.

“There were many times I woke up at 4am and couldn’t handle the anxiety, and I would jump in the car and go to King’s Cross station where I could get the first editions that were being loaded onto the intercity trains. This often paid off, because if parts of a news story were plain factually wrong, I could get hold of the newsdesk and work fast to get it changed for the second edition.”

Now the CEO of communications agency THRSXTY, he still wakes up at 4am, but these days he stays in bed.

“The difference between then and now is the internet,” he says. “I can review the news without leaving the house. As a small business with narrow margins, I’m more likely to be thinking about the agency’s numbers.”

As a crisis management expert who is also an adrenaline junkie, Oli uses visualisation to control his anxiety.

“I ride off-road motorbikes and much of the training for this sport is done by riding across miles of forests and rugged countryside,” he says.

“If I imagine I am riding across these landscapes, I can hypnotise myself into an enjoyable and peaceful state of mind.”

Jonny Nicol, founder and CEO of Stratajet

Jonny Nicol, founder and CEO of Stratajet

“Is our tech efficient enough?”
Jonny Nicol, founder and CEO of Stratajet

By day, he disrupts the private jet travel industry; by night, Jonny Nicol seeks a peaceful slumber.

“I once heard another entrepreneur say they sleep like a baby – waking up every couple of hours kicking and screaming,” says Jonny. “It’s not always quite that bad, but switching off from the daily grind can be tough, especially when everything you have is riding on the success of your business.”

Developed to revolutionise the private aviation industry by making it accessible as a means of mass transport, his online platform relies on a complex algorithm that fills empty legs of private jet routes.

“It took us two and half years to build these incredibly sophisticated algorithms, and another two to get the program to run quickly enough to be a viable consumer proposition,” says Jonny, a former pilot.

“We lost investor confidence and most of my nights were spent thinking of ways to trim valuable seconds off the time it took for the system to search through the available aircraft.”

His strategy for surviving sleepless nights? Boost your support crew. “I’ve brought in some of the best individuals from in and outside of the aviation industry,” he says. “They head up my customer service and marketing teams, ensuring that customers are getting the tailor-made attention they deserve, as well as access to a range of top-of-the-range services and partnerships. My team are so important.”

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