A winner never quits and a quitter never wins

15th June 2026
June Sherpa dinner 1 - A winner never quits and a quitter never wins

Tom Matthews


We recently held our six-monthly Pemba team Sherpa dinner and took the opportunity to reflect on what has been an exceptional 12 months for our team.

It has been a year of significant exits, strong DPI generation, new platform investments and continued accelerated growth across many of our partner companies.

As we celebrated these achievements, one observation stood out to me.

The thin line between success and failure

Many of our most successful outcomes came remarkably close to not happening at all.

There were transactions where the preferred buyer walked away.  Deals that appeared dead.  Processes where vendors chose another path.  Situations where, at various points, it would have been easy to conclude that the opportunity was lost.

Looking back, the margin between success and failure was often razor thin.

What ultimately separated the successful outcomes was not superior modelling, intelligence or strategy.  It was perseverance.

Persistence is an underrated advantage

The common thread across many of these situations was the refusal of our team to give up.

When others may have moved on, they stayed engaged.  When the obvious path disappeared, they continued looking for solutions.  They had one more conversation, made one more call and explored one more option.

In investing, there is a tendency to look at successful outcomes in hindsight and assume they were inevitable.

The reality is usually very different.

Most successes are fragile.  They require resilience through uncertainty, setbacks and moments when the odds no longer appear favourable.

What I’ve learned

One lesson I have observed repeatedly throughout my career is that perseverance is an underrated competitive advantage.

Many people are capable.  Many people are intelligent.

Far fewer are willing to persist when things stop going according to plan.

The ability to remain committed when the outcome is uncertain often becomes the difference between success and failure.

A quote worth remembering

A quote that has always resonated with me comes from Siggy Wilzig, who survived the Nazi death camps before building a banking legacy in America.  His advice to his son was simple:

“Never give up.  Only death is permanent.  Everything else can be fixed.”

Final thought

Success is rarely about avoiding setbacks.  More often, it is about refusing to let setbacks become the final chapter.

The best outcomes are often achieved by those who simply stay in the game long enough, work hard enough and persist long enough for the opportunity to emerge.

Related Articles.