Jack had spent three years personally hunting mistake fares and pricing glitches to visit more than 40 countries before turning the habit into a product. He began emailing the deals he found directly to his own friends, and framed the newsletter as a spin-off of that personal hobby rather than something built to answer a specific request.

“Over the last 3 years, I've been able to visit over 40 countries”

Jack emailed his cheap-flight finds directly to his own friends and contacts. Within eight weeks that had grown by word of mouth to over 2,700 subscribers.

“8 weeks ago I started a free email alert newsletter sending out cheap flight deals to my mates”

The first paying customers came from converting Jack's existing free subscriber base once he introduced a freemium tier. Existing subscribers were offered a discount on the new paid option, and a reported 2,500 of roughly 165,000 subscribers upgraded to paid. This happened well after the free list had scaled into the tens of thousands, not in the newsletter's first weeks.