A Life Well Lived

As part of our journey to redefine Wealth we are exploring what “A Life Well Lived” means: interviewing artists, entrepreneurs, explorers, and change-makers as they share their stories and ask “what is my life well lived?” Here we talk to Henry Hales, founder of the London based men’s clothing brand, Sir Plus, about his business and what living well means to him.

Founded in 2010, Sir Plus began life selling men’s boxer shorts on Portobello Market. Having steadily grown since then, the business is now based on the corner of Golborne Road and Portobello Road in their first bricks and mortar store, a stone’s throw from where it all began.

“The business is a men’s clothing brand that makes staples from surplus fabric.” Says Henry.

“Prior to founding Sir Plus I was at university – I studied real estate management so not massively creative – and when I graduated I started making boxer shorts, selling them on Portobello Market. At that stage I still expected to go into property, but really wanted to try and build a business.”

On Work

“I saw a gap in the market for well-made men’s underwear, but I’ve since discovered that they aren’t necessarily the best business venture, simply because somebody like Justin Bieber could sell far more than I can, just by being on a Calvin Klein billboard. They’re relatively low margin as well, so I would have needed to be making hundreds of thousands to benefit from economies of scale which as a startup, I certainly couldn’t do. The business has since evolved into a clothing brand, which was a bit of a surprise really, and boxer shorts are now just a small part of the range.”

“I always wanted to run my own business, ever since I can remember, and I knew that the best time to do that would be after I graduated. In the beginning I never thought I’d be able to take it full-time, or I thought I would at least have to start a “proper job” and then slowly build this into something later on. But after maybe four or so months of working on Sir Plus, I put the proper job on hold, and carried on doing this. I didn’t have myself down as a menswear designer, but I love it.”

“Compared with a typical 9-5 job, I don’t ‘switch off’ – but at the same time it never feels like a grind, because you know that everything that you’re doing is to improve your business, and if you’ve got a good team around you – which we really do – then it should be a pleasure coming in to work.”

“It is all-consuming. You even think about it in your sleep. I imagine it’s probably like having children in that it’s immensely hard work, and immensely satisfying at the same time.”

On Advice

"I feel like anyone can do it. It is just down to applying yourself, taking a gamble, and being able to stick it out and evolve.”

“I think there might be something in an entrepreneur that drives them really hard, or allows them to better manage risk – but I feel like anyone can do it. It is just down to applying yourself, taking a gamble and being able to stick it out and evolve.”

“If you are starting in an industry, or in a sector where you think there’s a gap, or something you believe in, then I would just say persevere. Sir Plus definitely wasn’t an overnight success, so I think a lot of it is just down to perseverance and hard work. It is definitely a passion of mine, but it also needs to be a commercial business otherwise it simply won’t survive.”

“I had a stall on the market for about five years, and you always read about how dead the high street is, so it really put me off taking a proper bricks and mortar shop, but since we opened the doors here we’ve been really busy – we couldn’t have had a better response. So I think to also try and be less influenced by what you read, and trust your own instincts, because I should have done this a long time ago. Hopefully we’ll know next time, and we’ll be able to make the step sooner.”

On Milestones

“There were many different moments that combined, all helped – but I think getting my first bit of press was pretty huge. It wasn’t a massive publication, but to me it really validated the business.”

“Another was the first time we ran a sale event. I remember us taking good money and thinking, “you know what, this could really work.” Another thing that had a real impact was getting a feature by a guy called ‘The Grey Fox’ for quite a niche product which we then ranked top of Google for. I realised that by adapting the website and the range to include more unique items, we could sell well online, something we hadn’t really tried until then.”

On Success

"I suppose what I mean is that money isn’t the most important thing. For me it’s quality of life.”

“Personal success probably has a lot more to with your state of mind, and your friends and family. How much I am enjoying life is basically the most important thing for me. That is of course influenced by how successful the businesses is, and my lifestyle will ultimately be impacted by how much we grow and how much we can evolve, so the two are definitely combined. I suppose what I mean is that money isn’t the most important thing. For me it’s quality of life.”

“In terms of success for the business, to have been running for seven years now – and to have sold I don’t know how many thousands or tens of thousands of garments – to know that they have all been made in a decent way, to have built a successful team and to have a brand that people have heard of, is immensely satisfying. I certainly don’t have any kind of ballpark figures that we need to reach, so if we can carry on evolving the way that we are now, then that’s a good thing.”

On Living Well

“To live a good life I think is to be happy. To simply be a nice person and to not do anything that you know is unpleasant to somebody else. To have fun and to enjoy the benefits that hopefully, a successful life might bring. Whether that’s family and children or holidays – to just live every day like it’s your last.”

On Wealth

"If you're not constantly worried about money, that's a rich position to be in."

“I don’t know what most people’s definition of wealth would be, but to me, if you have sufficient to do the things in life that you would like to do, and if you’re not constantly worried about money, that’s a rich position to be in. It doesn’t matter if you can’t afford a really expensive car, or a watch. For me to be able to go on holidays and eat out – to enjoy the normal things that I want to do is important. In terms of being ‘super wealthy’ I can’t imagine that would make you much happier – it just means you can buy more stuff.”

On Retirement

“I would imagine always having some element of work in there, but to be able to wind down a little bit, to have somebody else manage a lot more of the admin side of it would be great.”

“I enjoy traveling and it’d be cool to have shops in different cities across the world to be able to travel to, visit and help the team. So I don’t think of retirement as stopping, but hopefully the balance will shift and I’ll have a little bit of work and a lot of pleasure. Maybe even some sea and some mountains.”



You can find out more about Henry and Sir Plus by visiting their website or following them on Instagram.