When entrepreneurs see gaps and move fast

Tom McCallum
3 min readNov 19, 2020
entrepreneurs CAL
For the AvGeeks out there, VP-CAL, a B737–400 from the early 90s

Today a story from my past, then a piece of news around another fast entrepeneurial move around Covid vaccines from the Lloyds insurance market.

Cayman Airways and a two hour coup.

In July 1991, aged 25, I started a new job as the Financial Controller at Cayman Airways. After a hugely intense first few months of focus on internal restructuring, I thought I’d be able to cut back on the 70+ hour weeks.

However, on December 4th, 1991, I was woken by an early phone call that simply said: “PanAm is going to announce they are shutting down this morning, get into the office”. PanAm was one of only two competitor airlines on our main route, Miami to Grand Cayman.

One of our managers in Miami had “bucked up on” a PanAm manager who gave them a heads up that they’d announce a permanent shut down by late morning. Very quickly I found myself in the office with the MD/CEO and one or two others, working the phones, running spreadsheet models.

Within two hours (and before the official announcement went public) we had made and agreed on a commercial offer to take on all of the passengers booked on all PanAm flights, a major boost in revenues for us and a major commercial “coup”.

Mid-afternoon the same day the other competitor airline (one of the US major airlines) phoned us to say “hey, have you heard about PanAm?”, only for us to tell them we’d already taken on all their customers.

The airline business is tremendously dynamic at almost every level. Our relatively tiny, Caymanian owned and operated airline moved fast to take the entrepreneurial opportunity.

Lloyds and insuring vaccine transport

Today is November 19th. On November 9th, we had the first major Covid vaccine announcement (Pfizer/BioNTech). The second (Moderna) came on November 16th.

Now, how about this for a headline?

Lloyd’s approves new specialised syndicate to insure transportation of COVID-19 vaccine to emerging economies


After Hurricane Ivan devastated the Cayman Islands in 2004, I had the serendipitous privilege (we met when we were sat together on a Cayman Airways flight to Cayman about six weeks later), I got to know one of the brightest and entrepreneurial thinkers I’ve ever known, and one of the leading insurance brokers at Lloyds.

Over the next several years, I voraciously devoured learnings from that person and people introduced by them.

Lloyds is, almost by definition, an institution founded and based on a) seeing opportunities, and b) moving fast into those gaps.

The announcement above is a perfect example.

Oh, and as to moving fast. The date of that press release was not a few days after the first November 9th vaccine announcement. Whilst that would have been remarkable enough, the actual press release date may shock you at how well Lloyds saw the gap and positioned themselves. The date? July 23rd 2020, nearly FIVE MONTHS before the first such vaccine announcement.

I love smart thinkers, I love fast thinker, I love entrepreneurial thinking.

Kudos to the Lloyds community for being all three in this instance and so often in the past!

Originally published at Tom McCallum.



Tom McCallum

Sounding Board for Visionary Leaders ready to make a Massive Impact. Daily posts here, or https://tommccallum.com/newsletter-sign-up/