Starting a company is empowering, fun and fulfilling. But every entrepreneur’s journey to success is littered with rookie mistakes, unforeseen challenges and a heap of regret. While most entrepreneurs agree that this is a rite of passage, they also know that a bit of forewarning could have gone a long way.

Being an entrepreneur

To find out more about this, we sat down with a couple of successful entrepreneurs to explore what advice they would give their younger selves when they were just starting out. Our panel was made up of Gregory Lewis, who foresaw the holiday rental boom when starting OIRDXD Vacation Homes Rental LCC, and Tony Belot, who started TBP FZE, a highly successful photography business based in Dubai, over 15 years ago.

We began by finding out about some of their blind spots when first setting up.

Is there anything you wish you had known before starting?

Gregory: The world is a tough place. Working for someone else somewhat shields that. So be prepared that you are out there on your own.

Tony: Being a founder is lonely most of the time so be prepared to experience a roller coaster of emotions.

Gregory: Also, if you don’t do something, no one else will, so know that everything, absolutely everything, falls on your shoulders to understand it, sort it, deliver it, and manage it.

Are there any challenges you have come up against that you weren’t expecting? How have you overcome these?

Gregory: With a new business not seen before it’s the apprehension of how the market will take it. Sometimes you have to keep adapting your business model as you see and experience things that you just didn’t think of. The key is to absorb, and keep absorbing. You will then naturally approach these difficulties in a different way.

Tony: I was discouraged by my family not to take the risk! But if you have a passion for what you love to do, you have to listen to and follow your heart. You will succeed.

We then delved deeper into what it’s like to be your own boss. This is a dream for many of us in the UAE – 73% to be exact, according to a recent survey of both established and aspiring entrepreneurs across the Middle East and North Africa (MENA).

The hope of personal fulfilment and the freedom to choose a work-life balance were top reasons for holding on to this dream. But before we get on to the good stuff, a quick reminder of the bad!

What’s the most challenging thing about being your own boss?



Tony: You alone are responsible for the success or failure of your business.

Gregory: Nothing will get done unless you are behind it. There is no one above you to tell you what to do. It’s relentless and there is no time that you can take your foot off the pedal.

What’s the most rewarding thing about owning your own company?

Gregory: Freedom. Freedom of thought and freedom to action anything in any manner you want. Working for someone else, you are told what to do through the eyes of another, which you might disagree with. To make your own decisions is truly amazing. It gives you back your identity.

Tony: You can get things done faster. You’re able to make decisions without consulting others. And you get to be flexible and proactive.

With every new business venture comes the risk of poor decisions and the inevitable regret. In the same survey of entrepreneurs in the MENA region as mentioned before, the single biggest pieces of advice entrepreneurs had were to ‘Not be afraid of failure’, to ‘Do extensive amounts of market research’ and to ‘Have a great business/marketing plan’. We asked our entrepreneurs what advice they would offer to those just starting out.

What advice would you give your younger self about starting your own company?

Tony: Focus on one thing at a time to master methods and techniques.

Gregory: It’s going to be hard work. But it will open your eyes to aspects of business that working for someone else will never give. Think smart, always follow your gut instinct. Stick to your principles.

If you could go back and do it all again, would you? What would you change?

Tony: Yes, for sure. I would change the time where I started. I would do it earlier.

Gregory: I would for sure, too. The only thing I’d change is that I wish I took more chances when I started. But it’s a big step, it’s a huge step. Over time your confidence builds and therefore you start to make these bigger decisions and take these bigger chances. You have to have huge confidence at the start.

Starting earlier and taking more chances are common regrets among entrepreneurs, so we’re certainly of the same mind as Tony and Gregory. Yet what we would say is that starting early doesn’t have to mean starting the business early.

Wade Foster, founder of task automation business Zapier, once said: “I would have definitely experimented with more stuff in high school and college. Programming, science, selling… and I ended up having some catching up to do.”

So even if you don’t have the chance to start now, you can still get ahead of the game by building the skills you will need in the future.

The best advice of all?

It’s also true that even when we’re prewarned of mistakes we can still fall into the traps. It happens to the best of us, so however you start out don’t be too hard on yourself if things don’t go to plan. Just be sure to learn from the mistakes.

Saying this, we’ll leave it to Gregory to provide potentially the most important tip of them all: “Buy more coffee. Make sure you have a lot of coffee stored.”