A case study in personal wellbeing

At the advent of the Instagram and paid newsletter craze, David Sherry, a young photographer from LA, had the idea of selling high-quality, editorial-level stock images for publications and other freelancers to use. Around 2013, he started with a free weekly mail-out containing photos that he and his partner had shot around town and further out whenever possible. ‘We had about 20,000 people on the newsletter who were getting our photos on a zip file,’ he says. Eventually, they crowdfunded $20,000 for a US road trip, with photos going to all those who chipped in to the campaign. This proved a hit and set the groundwork for a paid subscription service.

Within two years, Death to Stock had 250,000 subscribers – but with the success emerged new problems. David had to pivot from being a photographer to managing staff, clients and finances. ‘At first you’re just excited, you’re not thinking about anything; I didn’t expect things to grow the way they did. What starts to happen – and this is the common thread I see with other founders – is that suddenly I’m a CEO and the spotlight shifts. The business itself is a subscription business, and if you’re in the startup world, there’s a whole host of things that you have to think about that creatives don’t: lifetime value, churn, cohort analysis… There’s a whole side to the business that, frankly, I didn’t know.’

With his small team of three to four full-timers plus freelancers, David tried to juggle much of the work himself while often feeling ill-equipped to do so – typical imposter syndrome. Yet he was equally unwilling to raise his concerns, not wanting to let the team down. ‘Once you start perceiving yourself as a CEO and you’re not focused on the market and creatives, you start to second-guess yourself more. That led to a lot of anxiety and stress. What I wanted to do in the company was one thing – creative projects – but what I had to do was another – make sure our budgets are great. I remember being nervous in a meeting where I was going to hire somebody. You feel like you don’t know what you’re doing.’ Things got so bad that he couldn’t unplug himself from work and the anxiety followed him around. He recalls having a mini panic attack after bumping into a friend on the street and his social faculties had completely left him.

Reaching breaking point

The sum of this stress culminated in David getting ill. In 2016, on the eve of a company trip to Thailand, he came down with shingles – a painful rash that can often arise as either a result of stress or an autoimmune deficiency. Far from trying to bury the problem, the paralysing extent of the sickness forced him to stop and take time off, at which point he was forced to reconsider his work-life balance.

Among the first things he noticed was that the company worked just fine without his nannying every issue, which was revelatory. ‘That’s the funny thing: I don’t think there was that much need for stress, necessarily – I think it was a bit self-induced. I should have trusted myself a lot more and been OK with not knowing a lot of things. The truth is: there is no one way of being a CEO.’

A crucial point, too, was that David had been conflating himself with his company – an idea he delved into with the help of several business and life coaches as he was recovering from his illness. ‘That’s the biggest thing I see when I work with other founders: if you tie your identity to this company, then the ups and downs of that business will be your ups and downs. It’s a really bad recipe. And if the business is you, you think, “If I make more sales then this stress will relax.” But you can never win that way.’

Looking inward and making changes

So, if the company was doing fine – bar learning some budgeting skills here, and hiring the right person there – the issue was personal. So David started focusing on himself and reading more about diet and sleeping. He took up yoga. After exploring Tim Ferriss’ book The 4-Hour Body, he completely changed his eating habits. ‘Before, it was unconscious and haphazard; I’d eat out a lot. Now, the only sugar I have is either from fruit or dark chocolate. And no processed foods.’

Much of the stress that we experience is molecular, often unnoticeable, and David tried to address this, too, with breathing exercises and cold exposure, which he practices daily. ‘I start every day with meditation, breathing and a cold shower – you start off warm and turn the water cold for the last two minutes.’ This is part of the Wim Hof Method – developed by the Dutch extreme athlete – whose app David highly recommends.

But far from being neurotic about his health now, David says that he’s simply more conscious and educated. ‘One big shift was becoming aware of all those things. How do I feel when I have coffee? How do I feel when I get less sleep? It’s done in a healthy way – it’s fun and I don’t feel I’m off if I miss a day.’

In 2019, one of David’s employees bought into the company and took part of the daily management off his hands. With this newfound free time, he has launched several community-driven ventures. One is Jacuzzi Club – an online members’ space for business founders to throw around ideas and network. The other is his own foray into coaching. Since recovering from the burnout, David has given advice to around a dozen founders on how to get through similar issues. Sometimes, just having a forum to voice your problems is the most crucial component to wellbeing.

‘It’s hard as a founder to talk about this type of stuff,’ he says. ‘You’re not going to talk to your team. You’re hiding because you think you’re supposed to feel a different way. There’s a lot of self-sabotage that can happen there. You might want to get rid of your company – I’m glad I didn’t do that.’