[1] The following year he began working at the Department of Treasury at the Crown Companies Monitoring Advisory Unit as an advisor on state owned enterprise privatisation.

Gilmore left the public service in 1999 to join Ernst and Young, where he worked on international projects advising utility companies.

However, with the counting of special votes and the release of official results, National lost a seat to the Green Party so Gilmore was not returned.

[5][6] Emails were released under the Official Information Act in May 2013 from his time as a contractor to the Ministry of Business, Innovation and Employment (MBIE) in November 2012, just prior to his return to Parliament in 2013.

[7] The emails contained comments to a Treasury Manager during an argument in which Gilmore said, after noting he may be returning to Parliament as a government member, "I am sure this sort of thing will come back to haunt you if you want your career to reach its full potential.

[13] Gilmore runs a private property investment company, The Mighty Rocket Group, later renamed St Pauls Asset Management.

[16] In December 2021 Gilmore was ordered to pay NZ$11,000 in costs after a failed attempt to enforce a statutory demand against Mighty Rocket's landlord over the termination of its lease.

[19] After announcing his candidacy, Gilmore's parents commented that he needed to "pay his bills" before he seeks a seat on Wellington City Council, in reference to his unpaid debts that he owes them.