Liability Guy

Hi, I’m Simon.

Most people in the South African insurance industry know me as “The Liability Guy” — a nickname that somehow followed me around long enough to become a personal brand.

For more than 30 years I’ve worked in specialist liability insurance, helping businesses understand risk, protect themselves from the unexpected, and occasionally sleep a little better at night.

Somewhere along the way I also became:

• a public speaker,
• a television judge,
• a digital innovation addict,
• a writer,
• and a part-time mentalist fascinated by human behaviour.

Life gets interesting when you stop trying to fit into one box.

What fascinates me

There are three things I care deeply about in business.

Leadership

I’ve seen bad leadership destroy great businesses.

I’ve also seen strong leadership completely transform struggling teams and organisations.

Having spent years in both corporate environments and start-ups, I’ve become obsessed with the impact leaders have on culture, innovation, performance, and people’s lives.

Liability insurance

Yes, I genuinely find liability insurance fascinating.

Not because of policy wording or legal jargon — but because almost nothing meaningful happens in business without someone carrying risk.

Buildings get designed. Products get launched. Advice gets given. Technology gets built. Companies grow.

And behind all of it sits trust, responsibility, and the right protection.

That’s why I spend so much time speaking, writing, and educating people about specialist insurance and risk management.

Technology & AI

I’m convinced we’re living through one of the most important technological shifts in history.

Artificial intelligence has the ability to dramatically improve how brokers and underwriters understand exposure, manage risk, and protect clients.

That intersection between insurance, human insight, and technology is where I spend most of my time thinking.

Also… what a time to be alive.

The corporate world, and what came after

Most of my career was spent building and leading specialist insurance teams focused on areas like:

• Directors & Officers liability,
• Professional Indemnity,
• Cyber,
• Crime,
• and Commercial Liability.

But eventually I realised that many of the ideas I had about technology and innovation would probably never reach their full potential inside a comfortable corporate structure.

So in 2022, I resigned from my executive role and stepped into the far less comfortable — and far more exciting — start-up world.

Today I’m the CEO of The Liability Company, where we’re building a modern specialist underwriting business focused on expertise, innovation, and helping brokers navigate increasingly complex risks.

Other slightly unusual things I do

You can also find me:

• speaking at conferences,
• appearing in the media,
• performing mentalism,
• experimenting with AI tools,
• or playing the role of “Dread” as Head Judge on The Insurance Apprentice.

Yes, insurance has a reality show.

One last thing

I’m also a recovering addict with more than 24 years clean and sober.

That journey changed the way I see people, leadership, pressure, failure, reinvention, and purpose.

It taught me that the most important transformations in life rarely happen on the outside first.

Thanks for stopping by.

I’m Simon Colman.
The Liability Guy.