Rupert Cook joined the Cyber Runway Scale Founders Fireside to discuss his entrepreneurial journey and share insights on navigating the cybersecurity landscape. Topics included fundraising, product-market fit, and leadership lessons learned while building a successful cyber business.

On 11th February 2025, Rupert Cook, Chairman of Overe, joined a “Founders Fireside” event as part of Cyber Runway: Scale, a programme delivered by Plexal and supported by the Department for Science, Innovation & Technology (DSIT).

As a serial entrepreneur, investor, and mentor, Rupert has built and supported numerous businesses, particularly in cybersecurity. During this session, he shared hard-earned insights into what it takes to succeed as a founder, covering fearlessness, sales strategies, exit planning, and knowing when to pivot.

For anyone leading or scaling a startup, his advice was refreshingly direct, no-nonsense, and pragmatic, a must-hear for founders navigating the highs and lows of entrepreneurship.

I attended on behalf of Cyber Tzar, the Enterprise Supply Chain Risk Management platform, gaining invaluable insights into long-term business growth, strategic decision-making, and preparing for a successful exit in the cybersecurity sector.

Contents

Founders Fireside Rupert Cook 11th February 2025

This video is publicly available on the Plexal YouTube playlist for the Cyber Runway programme.

The Three Essentials for Startup Success

Rupert distilled the core traits every successful founder must have into three key elements:

1. Fearlessness
2. Charisma
3. Domain Knowledge

These, he argued, are non-negotiable. If an entrepreneur lacks any one of these three, their chances of building a scalable, sustainable business drop significantly.

1. Fearlessness: Making Decisions and Taking Risks

Being fearless is not about recklessness—it’s about bold decision-making and relentless execution.

• Move fast and break things. The best founders aren’t paralysed by indecision. They act, learn from mistakes, and adjust rapidly.
• Failure isn’t fatal. If you make the wrong decision, acknowledge it immediately, pivot, and course-correct.
• The worst thing you can do is dither. Many startups fail not because of bad ideas, but because they spend too long debating rather than executing.

2. Charisma: The Power to Persuade

Rupert defined charisma as “an infectious enthusiasm for what you’re doing”.

• Startups need believers. If you don’t exude confidence and excitement about your business, how can you expect employees, investors, and customers to get on board?
• Convincing investors. Raising money is not just about the numbers—it’s about selling your vision and getting others excited to be part of it.
• Hiring great people. Founders with charisma can persuade talented individuals to leave secure, well-paid jobs to join their risky but potentially world-changing startup.

3. Domain Knowledge: Why You?

Being passionate is not enough—you need deep expertise in the problem you’re solving.

• If you don’t have domain knowledge, you need a co-founder who does.
• Investors look for founders with unique insight, not just those who spotted a gap in the market.

A great example is James Hadley, CEO of Immersive Labs. As the lead instructor at GCHQ’s summer school, he saw how outdated cyber training was and built a better way to train security professionals through gamification and real-world scenarios. His first-hand industry experience gave him credibility—and an edge.

---

Setting Goals: Why Are You Doing This?

Rupert emphasised the importance of setting clear goals before diving headfirst into a startup.

• Why are you putting yourself through this? Being a founder is incredibly hard—financially, emotionally, and mentally. If you don’t have a clear reason, you’ll struggle when things get tough.
• Money isn’t enough. If your goal is purely to make money, think realistically about what it will take to reach financial success.
• Plan for the long game. Building a startup is often a 10-year journey. Ensure you have milestones and rewards along the way.

The Importance of Fun

“Are we having fun?” was a question Rupert suggested every founder should ask themselves regularly.

• Hard work doesn’t mean misery. Building a startup is tough, but it shouldn’t be relentless grind with no joy.
• Celebrate wins. Whether it’s landing a big customer, hiring a key team member, or securing investment, make time to recognise achievements.
• At Immersive Labs, they built fun into the culture—from “Thursday Thursday” social events to quarterly business reviews that were essentially big parties.

---

Always Be Selling

A piece of advice that Rupert repeats to every founder:

👉 “Always be selling.”

Many founders believe they are not natural salespeople—but if you’re bold enough to start a company, you’re already a salesperson.

• Speak to customers constantly. If you don’t fully understand their pain points, you’re building in the dark.
• Identify your ideal buyer early. What do they need? How much will they pay? What’s their buying process?
• Avoid “build it and they will come” thinking. A startup without paying customers is just a hobby.

Rupert warned that many startups spend too much time building and not enough time selling. Some founders he had spoken to had never even spoken to a customer—which he described as absolute madness.

---

Exit Planning and the Power of “Blatancy”

Rupert shared a simple truth:

👉 If you want to be acquired, you need to be noticed.

He introduced a concept he calls “blatancy”—a skill that many UK founders lack, but successful entrepreneurs master.

What is Blatancy?

Blatancy is about visibility. It means talking a lot, writing a lot, standing a lot, drinking a lot (at networking events), and not spending a lot.

• Get on stage. Speak at conferences, join panels, and make sure people associate your name with your industry.
• Write often. Publish blogs, articles, and LinkedIn posts. Winning awards also raises your profile.
• Be strategic with events. If you can’t afford a trade show stand, attend anyway and network aggressively.
• Position yourself near your future buyer. One entrepreneur Rupert knew deliberately placed his company’s stand next to Experian’s at every conference—they ended up acquiring his company.

---

Scaling and Raising Money: The UK vs the US

Several founders in the session raised concerns about UK investors being too conservative and asked whether they should raise funding in the US.

Rupert’s response was blunt:

👉 “If you’re too American for UK investors, you’re talking to the wrong investors.”

• The US moves faster and takes bigger bets. If UK investors hesitate too much, go where the money is.
• Some founders have doubled their valuations simply by flipping to being a US company.
• However, moving to the US isn’t always necessary—it depends on the market and where your customers are.

---

Knowing When to Pivot (or Walk Away)

One of the toughest questions for founders is: “When do I give up?”

Rupert’s take was pragmatic:

• If you’ve been running for 1–2 years without finding product-market fit, something is wrong.
• If you aren’t talking to customers, you’re just playing startup.
• Sometimes, it’s better to stop and start something new rather than waste years on a failing idea.

Startups require relentless optimism, but blind persistence in the wrong direction can be damaging.

---

Final Thoughts: Be Bold, Be Visible, Be Fearless

Rupert’s session was packed with practical advice for founders at any stage. His key takeaways:

• Fearlessness, Charisma, and Domain Knowledge are non-negotiable for founders.
• Always be selling—talk to customers and refine your pitch constantly.
• Set clear goals—know why you’re doing this.
• Maximise visibility—blatancy gets you noticed by investors, partners, and potential acquirers.
• If UK investors are too slow, consider raising in the US.
• If you haven’t found product-market fit in two years, rethink your approach.

Startups are tough, but as Rupert emphasised: “You can’t wait 10 years to have fun.”

The best founders build companies that work hard, move fast, and enjoy the journey.