How Jack Sheldon turned his free Jack’s Flight Club newsletter into a money-making business

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.

19 Jun 2017

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