5 July 2018 Courier Issue 17

How Jack’s Flight Club became a money-maker

Turning a digital hobby into a money-making business has flummoxed many. Jack’s Flight Club has made it work by offering paid-for supplements on top of a free service.

Jack Sheldon has a talent for finding the cheapest flights. Thousands of his newsletter subscribers would attest he’s better at it than even famous sites like Skyscanner and Expedia.

Sheldon is a private travel agent: all he needs for work is a laptop and his geeky insider know-how concerning every aspect of how airlines price their flights. 

In September 2016, Sheldon spent £30 on setting up Jack’s Flight Club. It was nothing more than a newsletter containing cheap air fares – a simple service that he thought could strike a chord with some of the 40 million-plus people that search for flights on Skyscanner each month.

Three months in, nearly 3,000 people had subscribed through word-of-mouth. Promoting his newsletter on Reddit gave it another boost; his AMA (‘Ask Me Anything’) generated 42,000 more subscribers.

Could he turn this popular email into a moneymaker?

Sheldon considered several ways to monetise his newsletter: a total paywall felt too aggressive and likely to alienate people, while ‘affiliate links’, where Sheldon would take a cut on bookings, seemed antithetical to the idea of finding cheap flights. He settled on a ‘freemium’ model. For £35 a year, users could opt in to receive Sheldon’s flight alerts on a more regular basis. Non-paying users would still receive semi-regular flight updates.

His 165,000 original subscribers were offered a £10 discount. Of these, he says 2,500 signed up for the paid version. The challenge will be keeping up momentum now these users are paid up for the year.


Sheldon ensured an attractive product was still free, while affording sufficient additional value to people who pay. 

Your weekly dose of inspiration, advice & generally smart stuff.

Courier Workshop
Courier Weekly
Please wait...
Thanks! You've been added to our mailing list.
Oops! Something went wrong. Please try again.