Charlie Regis is the founder of Styliff, a creative agency that creates apps that stand out. They are to go-to agency for many Fortune 500 companies and the most exciting startups in the world.

Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?

Growing up, tennis was my life and I ended up laying the low levels of the pro tour in my late teens before having to make the hard decision to choose another direction in life. There have been two key skills that have translated very well into entrepreneurship:

  • Reflection

In tennis the vast majority of the time you are traveling and competing alone which means that you have to be very reflective and self-critical in order to analyze the performance and understand how to improve in the next match. You will often hear that players are their own worst critics. Yet the next time you walk onto the court you need to be full of confidence to perform at the top of your game.

In entrepreneurship the guiding hand that has been with you your whole life through education and your professional career telling you what is right and wrong has vanished and now you are in the wild. This reflective process is vital for growth as an entrepreneur as you have to be critical of your performance in meetings, your product, your vision…but the next time you step onto that stage or into that meeting, you need to deliver your pitch with 100% conviction and belief that you are going to change the world.

  • Losing like a champion

Tennis is a brutal sport. Unless you are Roger Federer, once you find your level, you lose every week. It might be the second round, quarter-final…but you would eventually lose. This has many parallels to entrepreneurship where you are constantly bouncing back from disappointments and putting out fires. Being able to shake off a loss and refocus on the long-term mission is absolutely key for both disciplines!

What is something you wish you would’ve realized earlier in your life?

If you are going into entrepreneurship expecting people to put in the same amount of work/ make the same level of sacrifice, don’t’ do it. It only leads to resentment which can and probably will kill a venture. Your priority should be to focus on delivering to your fullest potential and putting people around you in a position to succeed.

What are bad recommendations you hear in your profession or area of expertise?

The glamour of this narrative that entrepreneurs should be working 16 hours a day and sacrifice every aspect of their life in order to chase a dream is totally unsustainable. Whilst it may enable you to connect to an ‘identity’ of an entrepreneur you will find that experienced entrepreneurs focus much more on bring sustainable balance to life (it is worth keeping in mind that this looks different for everyone). If you are a few years into your journey in this game it is likely you are obsessed by your venture, learning how to disconnect and give your energy to family, friends, a hobby that fulfills you is key to creating a long term relationship with work that is ‘balanced’.

Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?

At this point I am involved with about 6 ventures at a meaningful level and others with a much lighter touch. It was a huge learning curve for me when 3 of them were simultaneously going through crisis situations which had to be navigated very carefully. I was too emotionally attached to not just the venture but the people I was working with and their level of sacrifice to each of the projects to get it to this point. The compound stress of each situation on top of each other was something that took a very costly physical and mental toll. It also happened to be during the winter lockdown which didn’t help. I am currently still in the process of learning how to become less emotionally attached in order to preserve my mental health.

What is one thing that you do that you feel has been the biggest contributor to your success so far?

Grit. There are no promises in this game. No guarantees that your level of sacrifice, loyalty, and persistence will pay off. But turning up every day and with a focused commitment to the cause over span of years is what it takes to become successful and that to me is best described as being gritty!

What is your morning routine?

My alarm goes off at 6 am. I am fortunate to have a gym in my condo complex so I get to the gym at 6:30, I usually work out for an hour depending on my workload for the day it may be 45 mins. I keep my phone on airplane mode during this session for a number of reasons. It is a key time for me to collect my thoughts around the day rather than answering emails in between sets. This gives me an almost meditative effect. It also helps to make the session effective.

I cook a comprehensive breakfast and am at the office by 8:45. I like to be physically working by 9 am. I have a pretty strict cut at 7 pm where I try to put it all down for the day. This is not always possible with international calls and urgent situations but if I hit 4 days in a week finishing by 7 I consider that a success.

On Saturday mornings me and my girlfriend have a ritual of homemade pancakes. I think it is important to have a Saturday morning ritual that rewards you for a hard week.

What habit or behavior that you have pursued for a few years has most improved your life?

I try to take the weekends off. Again, this is not always possible. There may be a big pitch to prepare for or something important, but I do not get stuck into the ritual of answering emails on the weekends. I have found that detaching from work frees my mind to explore the playful side of ideas that relate to work which are not draining energy from you and rather providing you with energy.

What are your strategies for being productive and using your time most efficiently?

I like to literally create a to-do list at the start of every day where I identify my priority items.

Prioritization is key. There will always be 15 things on your to-do list. Focus on fulfilling the top 2-3 and don’t kill yourself about not getting to the #15 on the list. It is important that you are completely transparent with people around your priorities so that you don’t overpromise and put yourself under unnecessary pressure. Focus on the things that move the needle for you and your business(s) and delegate where possible.

I also think that it is very easy to bounce around your to-do list half completing a bunch of things. Focus on completing each task where possible. This results in fewer errors and allows you to take mini breaks to reenergize.

Another quick tip is to take one call a day whilst on a walk. It is a good mix-up and gets the body moving which is key.

What book(s) have influenced your life the most? Why?

There are a number of books that have influenced my way of thinking however, as I spend a meaningful amount of my time in digital innovation Play Bigger by Al Ramadan was a real game-changer for me. It focuses on the fundamental principle of category design which is all about creating a game-changing innovation that has you in a league of your own in your vertical. As a founder, it is vital that you focus on a problem that is category-defining rather than just an idea of a product!

Do you have any quotes you live by or think of often?

I am a big believer that ‘entrepreneurship is a game’. There is a game-like quality to it whereby viewing things through a lens of taking positions and making moves you are able to detach emotionally from outcomes and focus on making the best decisions possible with the information that is on the table.