From Schoolyard Hustler to CEO: How Simon Chappell Built a Data Protection Empire Simon Chappell, CEO and co-founder of Assured Data Protection, shares his journey from corporate life to entrepreneurship, revealing the risks, resilience, and relationships that shaped his success.

Opinions expressed by Entrepreneur contributors are their own.

You're reading Entrepreneur United Kingdom, an international franchise of Entrepreneur Media.

Assured Data Protection
Simon Chappell, CEO, Assured Data Protection

At just eight years old, Simon Chappell was already flexing his entrepreneurial muscles - selling posters in the school playground without his parents' permission. Decades later, that same drive led him to leave a secure corporate career and take the leap into building a London based Assured Data Protection, a company that provides cloud-based data protection. In this Entrepreneur UK interview, he reflects on his biggest challenges, creative funding tactics, and the lessons that have fueled his success.

What inspired you to start your business?
From a very young age I was always entrepreneurial. My parents tell a story about me selling posters in the school playground aged 8, having taken them off the walls of my bedroom without permission!

What was your biggest challenge and how did you overcome it?
For me it was the very first step out of corporate life into my entrepreneurial journey. In my case I was working in Private Equity, with the many things that brings (good and bad). Walking away from a regular income was difficult and is almost impossible without the support of people around you.

Related: The Growth Blueprint: Lessons from Scaling UK Unicorns

How did you secure your initial funding?
I had a pay-out from my final job as we were taken over by another PE fund. That was the "now or never" moment. Not to be recommended, but during the first two years as money got tight, I juggled 0% credit cards to buy computer servers.

How do you handle failure or setbacks?
At the heart of the entrepreneurial mindset, you will almost always find the traits of a salesperson. Anyone in sales knows rejection is the common thread of most opportunities. The moment you win a deal that numbs all the pain of the ones you lose and enables you to go again.

What advice would you give to someone starting their own business?
Surround yourself with talent. In my case, I've started three business – all with co- founders – all of whom were friends before we went into business together. When we set up Assured Data Protection nine years ago, the five of us were industry friends and former colleagues, so we knew what we were getting into.

How do you stay motivated during tough times?
Think of what an alternative day looks like in a job you don't really enjoy and only do to pay the bills. The worst day running your own business is better than the best day doing a job you dislike.

Share your tips for achieving success.....

Here are five tips for achieving success that have worked for me:

  • Surround yourself with good people
  • Accept that the more you succeed the harder it will be to fund your business
  • Don't dream about exits, dream about selling stuff
  • Create a working environment where people can feel like they belong
  • And most of all, HAVE FUN!

Related: Why Risk Management Gets Overlooked in Startups - And What Happens When It's Ignored

Growing a Business

How I've Mastered the Art of Watching Trends to Predict and Create Viral Products — and How You Can, Too

I've made trend-watching and in-depth analysis my habit. Here are the hacks that will be useful for anyone who wants to create products that appeal to global audiences.

Starting a Business

He Built a $100 Million Brand in Menswear — Now He's Taking On Baby Monitors After a Scary Wake-Up Call

Kevin Lavelle of Harbor proves that success in entrepreneurship comes with solving the problems you face yourself.

Business News

AI Could Cause 99% of All Workers to Be Unemployed in the Next Five Years, Says Computer Science Professor

Professor Roman Yampolskiy predicted that artificial general intelligence would be developed and used by 2030, leading to mass automation.

Leadership

Your Team Doesn't Trust You — These 5 Leadership Habits Are to Blame

Trust isn't a soft value — it's a measurable driver of performance and retention.

Science & Technology

Generative AI Is Completely Reshaping Education. Here's Why Leaders Can't Afford to Ignore It.

From dorm-room startups to faculty-built chatbots, the future of learning is being rewritten right now — and the institutions that can't keep up are getting left behind.