The now 37-year-old had achieved his goal of retiring before the age of 30 but soon realised that money, cars and girls did not make him happy.
That is when the entrepreneur in him surfaced.
Four years ago, Mr Guest started Perth-based Infinite Wealth to share his knowledge of generating wealth.
His work over the past four years won him the Grown Entrepreneur prize at the third annual Networking WA Entrepreneur and Innovator Awards.
Mr Guest said he got �deeply philosophical� during his retirement and spent his time reading, studying and listening to mentors.
He said he had always wanted to be inspirational but �the way I thought about inspiration� was not quite right.
�It�s about having the courage to talk about what you�re scared of,� Mr Guest said. �It�s about doing something for more than yourself, like the community.
�I�m very proud of myself but it didn�t come the way I expected it to.�
When Mr Guest started Infinite Wealth, he committed to donating 10 per cent of annual profits to charity, including Youth Focus.
The entrepreneur has lost three friends to suicide, inspiring him to initiate the #screwthetaboo campaign.