One thing: Risk Vs Reward

A Bold Start

Risk is everywhere. It’s the currency of opportunity, the toll we pay for growth, and the barrier that holds many back from what they truly want. The thing about risk? It’s never going away. So, the choice isn’t whether to take risks—it’s about which risks to take and how to make them worthwhile.

I’ve always believed that if the fear of failure is louder than the vision of success, you’re not dreaming big enough. But let me tell you, it wasn’t always this way. Early in my career, I avoided risks that I thought might set me back. I quickly realised that playing it safe often meant standing still.

The Balancing Act: What Risk Teaches Us

Risk is like a seesaw. On one side is fear—failure, rejection, loss. On the other side is reward—success, growth, freedom. But here’s the catch: the reward only outweighs the risk if you’re willing to step onto the seesaw in the first place.

One example? Launching TAB. There were easier, safer paths I could have chosen after my previous venture. Starting again wasn’t just risky—it was daunting. But I realised that the alternative, sitting on the sidelines, carried a greater risk: the risk of regret.

The truth is, every big move in life—whether it’s starting a business, buying your first property, or even sending that cold email—is a calculated gamble. The key word here is calculated.

The Psychology of Risk: Why We Hold Back

It’s human nature to avoid risk. Our brains are wired to protect us, to steer us toward comfort. But growth doesn’t happen in comfort zones.

Think about the last time you faced a risky decision. What stopped you? Was it fear of what others might think? Fear of losing money? Fear of failing?

Here’s a mindset shift that changed everything for me:

• Instead of asking, “What if this goes wrong?” I ask, “What if this goes right?”
• Instead of fearing failure, I focus on what I’ll learn—even if I stumble.

Risk is rarely about the external factors. It’s internal—how you perceive it, prepare for it, and respond to it.

Calculated Risks: The Art of Balancing

Taking risks doesn’t mean throwing caution to the wind. It’s about making informed decisions that tilt the odds in your favour.

In business, I manage risk by focusing on:

1. Diversification: Just like spreading investments across different properties or markets, I diversify my decisions. Don’t put all your chips in one pot.
2. Data-Driven Decisions: Whether it’s analysing market trends or leveraging AI in underwriting, I believe in using data to back every risky move.
3. Worst-Case Thinking: I always ask myself, “What’s the worst that could happen? Can I live with that?” If the answer is yes, I move forward.

For example, our approach at TAB has always been to embrace risks strategically. We’ve explored fractional ownership, launched new products, and leaned into technology—knowing full well that some ventures might take time to pay off. But the reward? A scalable business with diversified income streams and long-term stability.

The Rewards of Taking Risks

Here’s the thing about risk: it’s a teacher. Every risk you take, successful or not, builds resilience, sharpens your instincts, and expands your comfort zone.

One of my proudest moments this year came from taking a personal risk—delivering a poem at a product launch. It might sound trivial, but as someone who still battles public speaking nerves, it felt monumental. The reward wasn’t just the applause—it was the confidence I gained by pushing through discomfort.

On a larger scale, risk-taking has allowed me to grow TAB to over ￡500m in originations and aim for ￡1bn. The reward? Creating opportunities for my team, my family, and the investors who trust us.

Personal Life

Risk and reward aren’t just business concepts—they show up in every part of life. Think about parenting: spending time with your kids often means sacrificing other priorities. The risk? You fall behind on work or miss a deadline. The reward? Those moments where your kids open up, share their world, or simply laugh uncontrollably with you—those are priceless.

I’ve also learned that pushing yourself out of your comfort zone personally is just as rewarding. Whether it’s trying a new sport (I’ve been eyeing paddleboarding lately), getting back into fitness after a setback, or finally eating healthier (even when those chips are calling), the short-term "sacrifice" is far outweighed by the long-term benefits.

Here’s one that surprised me: learning to let go. For me, taking an afternoon off to do something as simple as baking cookies with the kids feels risky when there’s a to-do list a mile long. But I’ve found those are the times that recharge me the most. The clarity and focus I gain from stepping back often lead to better decisions when I step back in.

Life, like business, is a balancing act of risks and rewards. The key is choosing the risks that truly matter—and savouring the rewards when they come.

Lessons for the Risk-Averse

If you’re reading this and thinking, “I’m just not a risk-taker,” here are a few truths:

1. Small Risks Add Up: You don’t have to jump off a cliff to grow. Start with small, calculated risks—ask for feedback, test a new idea, or reach out to someone you admire.
2. Regret is the Real Risk: In 20 years, you’re more likely to regret the risks you didn’t take than the ones you did.
3. Prepare, Don’t Panic: The better prepared you are, the less intimidating risk becomes. Do your homework, create a plan, and trust yourself.

What’s Your Risk?

This week, I want you to think about one risk you’ve been avoiding. What’s holding you back? More importantly, what’s the potential reward?

Ask yourself:

• What’s the worst that could happen?
• What’s the best that could happen?
• And can you live with the outcome either way?

Chances are, the fear of risk is smaller than you’ve made it out to be.

Closing Thoughts

Risk isn’t the enemy—it’s the gateway to reward. Whether it’s a career move, a bold investment, or simply putting yourself out there, the greatest rewards come to those willing to take a chance.

So, what will your next bold move be? Let me know in the comments—I’d love to hear your thoughts and stories.

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