Optimistic entrepreneur who leads from front

OLLIE Phillips, 42, from Shiplake, is an entrepreneur and runs Optimist Performance, a team performance consultancy. He is an adventurer, speaker and four-time Guinness World record holder and a former England International Sevens player. He has just completed the “World’s Toughest Row” crossing the Atlantic in 38 days. He is married to Lucy and they have three children, Lillie Mae, Nia, and Alfie.

Describe your business:
Optimist Performance has a simple but ambitious mission — helping organisations go from good to world class. We work with senior leadership teams on the things that truly drive business success — culture, trust, alignment and the ability to make sharp decisions under pressure.

How many people does it employ?
We operate with a small core team and a network of specialist optimists, allowing us to bring together the right expertise for each client engagement.

What did you do before you started this business?
I was a professional rugby player for most of my twenties. I captained the England Rugby 7s team. Like many athletes, injury meant that chapter closed earlier than I’d planned. What followed was a mix of coaching, business, and a growing restlessness to test myself in new ways.

When did you start your business?
Optimist Performance was founded in 2014.

What was your objective?
To give ambitious businesses the tools, the insight and the challenge they need to bridge that gap between strategy and behaviour. To help leaders lead better, teams trust each other more and organisations perform at a level they didn’t think possible.

Who or what influenced you to set up your own business?
There wasn’t one single moment — it was more of a slow realisation that built over years. Growing up, I was shaped by coaches and teammates who understood that the difference between a good team and a great one wasn’t talent — it was culture. I saw that at its best in elite sport, and I’ve never forgotten it.

Do you have a mentor or role model?
Two people. My mum taught me the fundamentals that no coach or business school ever could — work hard, be kind, back yourself and never stop believing that things are possible. The late Steve Black. Blackie, as everyone knew him, is one of the most remarkable people in British sport — perhaps best known as the mentor behind Jonny Wilkinson’s extraordinary career. What made him so special wasn't the technical knowledge — it was the way he made people feel.

What would you do differently if starting again?
I’d start with more focus and less fear. In the early days I tried to be too many things to too many people. I’d also invest in building a team earlier.

How is your business doing compared with last year?
Really well and I’m genuinely excited by the momentum we’ve built. We’re working with more leadership teams than ever — both here in the Thames Valley and internationally.
Do you compare on a regular basis?
It’s something I feel strongly about. We track our client impact and business performance monthly but I also do an honest annual review of where we are versus where I’d hoped we’d be at the start of the year.

How do you market your business?
Most of our work comes through word of mouth, relationships and referrals, which I think says something important about what we do. When you change how a leadership team performs, they tell people.

What’s the best thing about running your own business?
The freedom to do work that genuinely matters.

What’s the most challenging aspect?
Balancing growth with protecting the quality and depth of what we deliver. The work we do only has impact if it’s done properly.

Where is your business headed?
Towards greater impact at scale — but always on our terms. We want to be the go-to partner for ambitious leadership teams.

How important are online sales?
Digital platforms are increasingly important for scaling our tools and insights but relationships remain at the heart of leadership development.

Are you using Generative AI to shape your business?
Yes, and thoughtfully. We’re exploring ways AI can help us analyse insights from our leadership diagnostics and accelerate learning for clients, while being very deliberate about keeping the human element central.

Do you have a five-year plan?
Yes — although I hold it loosely. The plan is to grow Optimist Performance into a business that’s recognised as the leading leadership and team performance consultancy in the UK, with a suite of diagnostics, coaching and development tools that create genuine, lasting change.

How do you have a work-life balance?
I’m not sure “balance” is quite the right word for how I live. What I’ve found works for me is integration rather than balance. Exercise is non-negotiable — it’s how I process, reset and show up at my best. Family time is protected.

Do you set any goals at the start of a new financial year?
Absolutely — it would feel strange not to, given that so much of what we teach is about clarity of purpose and direction.

What’s the most valuable thing you’ve learned?
That culture eats strategy for breakfast — and I mean it. The best strategy in the world won’t save a business with a broken culture and I’ve seen this play out time and again with the organisations we work with.

What advice would you offer to anybody starting a business?
Start with a problem you genuinely care about solving — not just a gap in the market. The hard days are easier to get through when you’re genuinely invested in the mission. Build relationships before you need them, and protect your reputation fiercely.

What’s the biggest mistake you’ve made?
Trying to do too many things at once.

How organised are you?
Fairly organised but I’ve learned not to be a slave to the system. I have a great team around me who keep things on track operationally.

How are you planning for retirement?
Retirement isn’t really a concept I’ve given much thought to — and I mean that in the best possible way. When your work is genuinely aligned with what you believe in, the motivation doesn’t fade.

What’s the secret of your success?
Optimism — and I don’t mean blind positivity. I mean a genuine belief that improvement is always possible.

What three qualities do you think are most important to run a profitable business?
Clarity, resilience and genuine care — for your clients, your team and the quality of what you deliver.

How do you dress for work each day and is it important?
Smart but relaxed. I don’t believe in dressing to impress — I believe in dressing in a way that helps you show up with confidence.

What can’t you do/be without every day?
Exercise.

Lunch at your desk or going out?
Out, whenever possible. Getting away from the desk, moving, getting some fresh air — it’s part of how I stay sharp.

What change would you most like to see in 2026?
More businesses treating leadership development as an investment rather than a cost. The evidence is overwhelming that great leadership drives performance, retention and culture — yet it’s often the first thing cut when budgets come under pressure. I’d love to see more organisations making the connection between the quality of their leadership and the results they achieve.

Interview by Will Hamilton, intermediary and global marketing consultant, Hamilton Associates