Jamie Smalley: “It is funny but the harder I work, the luckier I get”

Do not participate in any marketing activity that is not measurable. Knowing you have received value for all of your marketing spend is fundamental to scaling a business. As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Jamie Smalley. […]

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Do not participate in any marketing activity that is not measurable. Knowing you have received value for all of your marketing spend is fundamental to scaling a business.

As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Jamie Smalley. Jamie is co-Founder of Runderwear. He is a marathon runner with a PR of 2 hours 42 minutes, has competed in an Ironman triathlon and ultra-marathons across four continents testing the companies new product developments on his journey. The company now sells its award-winning products in Europe, the Middle East & Australia. He now heads up the North American division and the companies growth in the region.

Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?

I grew up in a seaside town in the United Kingdom called Poole. I had a very outdoors-based childhood and as a result, I was an extremely sporty kid. From my very earliest memories, I was always arranging running races in the school playground in between classes, notably always trying to beat another little boy called Alan (he was the only boy I couldn’t beat. I never actually beat him!). Later at the age of 10, I entered the local mini-thon, a one-mile race that held big kudos in my hometown. Having seen the amazingly big trophies on offer in the town library for the first three finishers, I had to win one. I came second on that day and I could not have been happier. My love of running and racing was born.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah-ha” moment with us?

Back in 2007, I entered the New York marathon having been running marathons for a couple of years. I suffered terrible chafe issues. On my return, I was speaking to my best friend from Loughborough University (a fellow runner) Richard Edmonds and we set out to solve this huge issue for the running community.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

Listening to the right advice was key. Identifying people whom I valued their opinions and respected and asking them for advice. I analyzed the advice and made a schedule of tasks that would ultimately lead us to having a commercial product by breaking it down into 90-day objectives.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

Have a coffee with three people who work within the market. Gauge the market conditions. Is it a growing market? Is there any insider information that you may be unaware of as purely an enthusiast/hobbyist? What are the things that are missing within the market that could help drive efficiencies?

Lastly, I would write a list of all new technologies and trends in the world that are springing up and cross-reference them on how these could influence or be implemented within your given market as a form of idea generation. Accessing all of these factors along with my own self-assessment of my own level of passion to execute would determine my confidence in entering the market.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

Having a new project always on the horizon within your task list. For me, this can be in the form of a new product offering. We are moving into sports bras which has been a huge challenge and as a result very motivating. Learning about the market with no preconceived perceptions has been really interesting.

The new project could also be in the form of entering a new geographical market which brings with it new challenges that you have not previously faced. This is fun and keeps you in learning mode. The day I am not learning is probably the day I will start to dread working.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

The most enjoyable aspect of running my own business is the learning aspect. I become bored very easily and every day there is a new challenge to learn and adapt which I find hugely motivational.

The downsides are not being able to entirely switch off from the business which will impact other parts of life. Management of this is key and accepting you will not have a perfect life-work balance is something you have to accept. It is easy to be continually dragged into the ‘next task’. Managing the right balance of what the business needs and what other people in life need of you is a balancing act.

What has helped me over the years of running the business is the systems you put in place with clear time constraints on yourself. This will vary from person to person but finding what works for me has taken time.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

I have not had a full-time job so I had no ‘previous job’ to compare against. I was self-employed from the day I left university. If I am honest I had no idea what my job was. I have had to learn and figure it out as the business has matured. I think in the early days I hadn’t realized how much administrative work was required when trying to get the business off the ground. When you are bootstrapping you have to do this yourself which can be hard and frustrating.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?


Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Diversifying our product offering too quickly. We got a little carried away on the back of the first taste of success and diversified into products we should not have at the time. We could quite easily have lost the business as a result which wasn’t really a funny mistake! However, looking back it is in-line with the entrepreneurial mindset of always expediting all aspects of the business. The lessons learnt are to be patient in the early stages and when you think you are ready for a new product offering, do what you are really good at for another year and double down on it in my opinion.

Who has inspired or continues to inspire you to be a great leader? Why?

A man who will be unfamiliar within the U.S but the soccer coach of Liverpool F.C in the 1960’s called Bill Shankly. I was quite obsessed with him in my teenage years and consumed everything I possibly could on his life and management style. He built a dynasty at the club which still makes the team successful to this day. His ability to build trust, motivate, communicate and lead was decades ahead of his time. Any learnings I tried to take into the world of business when starting and growing the business.

How have you used your success to make the world a better place?

We may be a little early to have changed the world for the better thus far. I would love to be asked this question in years to come. We are socially conscious in that we have internal objectives as a company to minimize packaging, making our packaging recyclable and from recycled materials. This should be par for the course for business owners in 2020 and beyond.

In the future, I would like our business to have had a far-reaching impact on improving the health of our customers whether it be through the products that we produce that enable them to run or workout in greater comfort when possibly they would not have been able. Making them healthier and thus putting less strain on healthcare resources. Also, I would like to set up initiatives for the older population to remain active. As the population lives longer I feel this will be vitally important in our society.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Do not participate in any marketing activity that is not measurable. Knowing you have received value for all of your marketing spend is fundamental to scaling a business.
  2. Do not diversify your product offering for the first 3 years of the business. Keep the messaging consistent will help you gain more traction.
  3. Outsource administrative tasks as early as financially possible to allow yourself to work only on growing and adding value to the business.
  4. Keep a close eye on costs and scrutinize all out-goings and if they are necessary to the growth of the business.
  5. Write a clear Vision statement, Mission statement and agree to the Core Values and re-visit every year to give yourself and any partners clarity on the direction of the business.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

Tough question but it would be around the space of offering channels of opportunity for self- improvement to people who are road-blocked in improving their lives. In whatever capacity this may be and in various geographies. I would take great pleasure and be highly motivated in enabling this and offering opportunities and freedom to people in the future to improve their lives.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“It is funny but the harder I work, the luckier I get”.

The root of this quote dates back to Confucius about 2,000 years ago apparently but was made famous in the 1960s by Gary Player the champion golfer. It was relevant to me in that I have had to work extremely hard in all stages of my life to achieve the goals I have set myself both as a sportsperson and in business.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Al Gore — firstly as a runner we could enjoy a good run together before the breakfast or lunch! I think it would be a fascinating breakfast of learning.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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