My Hour with Donald Trump: What I Learned 

On October 8, 2012, I had the rare opportunity to sit down with Donald Trump for an hour. At that time, he was best known as a larger-than-life business figure and reality TV star, a figure whose bold approach to success, while not without controversy, fascinated many—including me. Back then, I found his perspective compelling. But over the years, much has changed, both in my own perceptions and in the broader understanding of his often polarising and divisive rhetoric.

The insights he shared during that encounter have lingered in my mind, taking on new meaning as the years passed and his public persona evolved. Now, as he works his way through his second term as President with the same bold energy that defines him, it feels like the right time to revisit those lessons and consider what lessons, if any, still resonate today.

This blog begins with a transparent look back at what I wrote 13-years ago, capturing how I saw things at the time. From there, I’ll fast-forward to today, focusing on one lesson that feels especially relevant to cybersecurity in this complex and unpredictable era.

Back to 2012: Donald Trump on Rolling the Dice

This year, Donald Trump is being showcased at the NAC, London. It's 2012, and thousands of people have stayed to hear him speak, including me. The atmosphere at the ExCeL is excitable. He's filled the same spot as Richard Branson did last year – the finale.

Everyone knows the man. He's an American real-estate billionaire, a television personality and author. He's also the chairman and president of The Trump Organization and the founder of Trump Entertainment Resorts. He's known for his hair, extravagant lifestyle, beautiful wives, outspoken manner and role on the NBC reality show The Apprentice.

Anyway, I have to say, having seen him in the flesh and heard him speak – I like the guy. With anecdotes and stories, he came across as being down-to-earth yet rather ruthless, which always makes for an interesting combination.

Right from the offset, he's straight talking. He immediately begins by mocking some of the weekend's speakers – those who've only ever made money by selling books online or from the stage on how to be successful. Having spent a year in Internet Marketing, I know exactly what he means, and I chuckle.

Trump's Top 10 Tips for Business Success

1. Love what you do. If you don't love what you do, you'll resent every working day. Furthermore you won't actually be very good at whatever it is you'll be doing. For me, it's interesting that he places so much value on this as it's something I've heard time and time again. And, I know it to be true from my own personal experience.

2. Always be mistrusting, and prepare for the worst. He elaborates more during point 3.

3. Hire the best people. Gone are the days when he proclaimed, ‘hire the best people and trust them.' Now, he advocates ‘hire the best people and don't trust them.' His reason being that if they're exposed to your weaknesses they'll want to take over your company, your wife or even your dog! He highlights managers of athletes and entertainment artists as an example – sadly.

4. Be focused. If you're not focused, learn to be. He's talks about the fact that there's some truth behind the old saying,

‘The harder you work, the luckier you'll get.'

He gives a dinner meeting and event with 2,000 bankers, when he was on the point of business failure as an example. Had he not said yes to this, his business would have gone under.

5. Don't quit. There's only one way to fail in business and that's by quitting. So many people, in his opinion, don't have the drive and quit far too soon. They might have a good plan, or even a bad plan, but who knows – as they quit half way through – shame!

6. Go with your gut and trust your instinct. He uses how he came to sign for The Apprentice as his next example. The story goes that his agent (Jim) had instructed him not sign as 96% of TV shows in the US fail, no business show had ever worked on prime-time TV, and no American woman in their right mind would want to watch him!

He ignored his agent's advice and went on to reap the harvest of one of the most successful shows in America and the UK.

7. When someone hits you, hit back and five times as hard. His reasoning is simply on account of the onlookers. He argues you need to show them that you're a force to be reckoned with.

8. Believe in yourself, love who you are, and understand your subject. Do all of these and you'll get what you want – fact!

9. Sign a prenuptial. In his opinion too many great businesses have been destroyed through marriage breakups so be prepared from the start as you need to be able to work it out. From my own personal experience I couldn't agree more - there are always ways to take a company over, or ruin one even if you have legals in place.

10. Create certainty – in your business and life. To be successful, you have to be a warrior and confident in yourself and your ideas.

So that's it, and he ends by saying,

"Now go make Trump look like a small-timer!”

Back to 2025: Why Trump's Seventh Tip Resonates in Cybersecurity

When it comes to Trump's seventh tip—when someone hits you, hit back and five times as hard, it strikes a chord with me, especially within the context of cybersecurity and the tumultuous times we're living in.

At first glance, this advice may sound overly aggressive or confrontational, but when applied to the world of cyber defence, it takes on a deeper, more strategic meaning.

The cybersecurity landscape is characterised by relentless threats with data breaches and compliance failures happening daily. Organisations can't afford to adopt a "wait and see" attitude; they need to be resilient, proactive, and, yes, forceful in their response to ensure both survival and stability. Cybercriminals often rely on the apathy, hesitation, or unpreparedness of their targets. By the time an attack hits, it's not just about recovery—it's about the message your defence sends to future would-be attackers.

Trump's notion of hitting back "five times as hard" embodies the concept of deterrence. Cyber defence isn't just about patching up vulnerabilities or quietly restoring systems post-breach. It's about creating an environment where attackers think twice before attempting another assault.

Some companies I work with exemplify this proactive strategy by leveraging cyber deception and early warning technology to detect and divert cyberattacks before they can do harm. Many partner with others and take their defence capabilities to the next level. For example, they may be integrating advanced threat intelligence and AI-driven detection methods, and enhancing ability to identify and mitigate threats in real time.

This combination of deception, early warnings, and high-powered intelligence not only neutralises ongoing cyber threats but also delivers real consequences to perpetrators where attackers may face exposure, disruption to their operations, or even legal ramifications. This demonstration of strength not only protects against current aggressors but also warns others that you’re not an easy target.

Trump's advice is also particularly resonant in cyber resilience planning. Attacks happen—it’s not a matter of if but when. And the when isn't always future focused. Increasingly it'sa case of when you discover a breach has already happened.

What matters is how prepared you are to respond and how robust your recovery plan is. When an organisation bounces back swiftly, strengthens its posture, and showcases its ability to resist being brought down, it sends a clear message to internal stakeholders, the industry, and attackers alike: "We are prepared, and we won’t go quietly."

Finally, this tip is crucial in an era where reputation can make or break a business. A company’s response to a cyber incident is as public as it is technical. Customers, partners, and even regulators watch closely to see how you handle adversity. A firm, decisive, and effective retaliation shows leadership, preparedness, and competence. It’s about more than plugging security holes—it’s about demonstrating to the world that you’re not vulnerable, and that despite setbacks, you’ll emerge stronger.

While not every piece of advice on the list, in my opinion, has stood the test of time, tip seven is undeniably relevant in cybersecurity. It encapsulates the mindset required for navigating today’s threat climate—proactive, resilient, and never passive when tested. For those of us working in this space, it's as much about strategy as it is about survival.

Now I want to hear from you

Join me for a conversation on LinkedIn and tell me, what's the top tip you find most interesting from Trump's list? Explain as much or as little as to why - it's up to you.