Hi Tim, can you tell us about your journey as an entrepreneur? What inspired you to start your first business, and what were some key lessons you learnt along the way?
My entrepreneurial journey really kicked off back in 1998 launching Crussh, but the most defining early venture was launching Flutter in 1999, which later merged with Betfair. There wasn’t one big lightbulb moment – it was more about seeing a massive, established industry that was ripe for disruption through technology. We saw huge inefficiencies and a lack of transparency, and believed the internet could change that, offering better value and a better experience for customers.
Key lessons? Firstly, the critical importance of the team. You can have a great idea, but without the right people with shared vision and relentless drive, it won’t go far. Secondly, resilience is non-negotiable. Building something new is inevitably a rollercoaster. You face setbacks, market shifts, and all kinds of hurdles, and you have to be able to adapt, learn, and keep pushing forward. Lastly, truly understand your market and customer. Don’t build in a vacuum – build something people genuinely need or want, and be open to feedback so you can improve as you go.
As both an experienced entrepreneur and investor, how has your perspective on business changed over the years?
It’s definitely evolved. As an entrepreneur, your focus is completely on your own business – the operations, the product, the team, and just keeping things moving. It’s incredibly immersive and all-consuming.
Moving into investing, especially with Augmentum, gave me a much broader perspective. You start to recognise patterns across different companies, markets and founder types. You shift from deep involvement to assessing potential, strategy, and the strength and adaptability of the team.
However, being a founder first gave me a valuable perspective. I understand the immense pressure, the highs and lows, and that helps me support founders in a way that goes beyond just providing capital. You realise that great ideas are common, but great execution is what really matters.
What advice would you give to female founders specifically when seeking investment and scaling their businesses?
The core advice applies to everyone – build a strong business with a clear value proposition, know your market well, and know your numbers inside out. However, given the data which shows female founders receive significantly less funding, my specific advice would be:
Leverage your network, and actively build it. Seek out mentors, sponsors, and peer groups, both male and female. Warm introductions carry more weight, so start building those relationships early. Don’t underestimate the power of community.
Be unapologetically ambitious. Sometimes, there’s a tendency to pitch a ‘safer’ or smaller vision. Don’t. Investors, particularly in VC, are looking for businesses that can scale. Show them the big picture.
Choose your investors wisely. Look for investors who have backed female founders before, who understand your market, and genuinely believe in your vision beyond just the metrics. It’s a long-term partnership, so make sure your values align.
Let the data do the talking. While bias is a real issue, strong traction, clear metrics, and a data-driven approach are hard to ignore. Prove your business is working, and let the numbers speak for themselves.
What’s the best way to handle tough questions or investor scepticism during a pitch?
Scepticism isn’t necessarily a bad sign – it usually means the investor is engaged and stress-testing the opportunity. The key is how you respond:
Listen carefully. Don’t interrupt. Make sure you fully understand the concern behind the question.
Be prepared. Anticipate the tough questions. Know your weaknesses, potential risks, and competitive threats, and have thoughtful answers ready.
Honesty and transparency. Never bluff or try to spin a clear weakness into something it’s not. Acknowledge the challenge. Investors value self-awareness.
Reframe where you can. After acknowledging a weakness, show how you’re tackling it or what you’ve learned. Turn it into a demonstration of your problem-solving skills.
Use data. Back up your responses with data and evidence wherever possible.
Stay calm and confident. Don’t get defensive. Treat it as a conversation. If you don’t know an answer, it’s okay to say you’ll follow up.
Lastly, what are your top three tips for founders pitching their businesses to investors?
It’s hard to narrow it down, but here are three crucial ones:
Nail the narrative. Clearly articulate the problem you’re solving, why it matters, your unique solution, and the size of the opportunity. Make it easy to understand – assume the investor knows nothing about your specific niche initially.
Highlight the team. Investors invest in people as much as ideas. Show why you and your team are the right people to execute this vision. Talk about your experience, your passion, and any key hires you’re looking to make.
Demonstrate traction and know your metrics. Whether it’s user growth, revenue, key partnerships or product milestones, show proof of progress. Be on top of your key metrics (CAC, LTV, churn, margins). Knowing these shows you understand how your business actually works.
