Sky News has been following Ian's journey as a government promise - to end rough sleeping by next year - looks in serious doubt.
It was a target set by the Conservatives in their 2019 election manifesto - but a report by the Kerslake Commission is warning it will be missed, blaming "chronic and unresolved" issues in the housing system as it reports a 26% rise in rough sleeping compared with last year.
The commission was set up in 2021 to learn lessons from the response to homelessness during the COVID pandemic - the same year, an estimated 741 homeless people died in England and Wales. Most were men and drugs, alcohol and suicide were the likely related causes.
On the Sky News Daily, Sally Lockwood speaks to our producer Sarah O'Connell, who first met Ian when he was a teenager, to find out about the challenges he has faced over the years.
Plus, Sally is joined by Emma Haddad, chief executive of the homelessness charity St Mungo's - the secretariat of the Kerslake Commission, as they discuss the wider problems and what they think is needed to end rough sleeping.
Podcast producers: Soila Apparicio and Alex Edden
Senior podcast producer: Annie Joyce
Podcast promotion producer: David Chipakupaku
Editor: Wendy Parker