He and wife Caroline bought Faigan’s Millers Flat Kitchen and Cafe in July, only for Alert Level 4 to stymie its planned August opening.
For Mr Jessop, it has been a case of taking things on the chin and rolling with the punches.
Covid-19 has left the couple reeling with the loss of four of six of their full-time staff who chose not to be vaccinated, two of whom were the head chef and front of house manager, brought in as salaried business partners.
The Jessops have had to close the cafe doors two days a week because of staff shortages and turn away Christmas events, while still paying full salaries for four weeks to the four former staff members.
Mr Jessop also sold his Queenstown restaurant Prime on Wednesday, citing the uncertainty caused by Covid as the biggest factor in his decision
"It’s unlikely that there will be international tourists in Queenstown until July, even though they’re allowed in from May.
"To have to look eight months ahead until we get meaningful customers is too far ahead for me."
At their Millers Flat Cafe, the couple said it was always hard to get staff as there are few people in the valley and not many are qualified in hospitality, but having to pay people to not work for four weeks was unfair.
The Government had said unvaccinated staff could be given outside work but that was not possible in a kitchen or cafe.
"Other’s people’s stances have flow-on effects for others," Mr Jessop said.
"I’m a fighter, and a battler. I’m a ducker and a diver, but ... no staff, no customers."
The couple were unable to attend family events or give time to their parents, and their remaining staff were suffering similarly through needing to work double rosters.
They were dispirited and sad at what should be a busy and profitable time of year, but their fighting spirit remained, even if dulled by constant blows.
"We love the community and we love being here," Mrs Jessop said.
"We know we just need to do the hard yards now and it will come right."