Skinny O'Leary

Sidequest

Roster: Sly Withers, smol fish & Ursula
State/Territory: WA
Socials: @sidequest.music

Listen: Skinny’s Manager Of The Month Playlist

AAM’s Impact on My Journey

I was very lucky to be chosen for the Co-Pilot mentoring and professional development program in 2025, which is a testament to the work that AAM does throughout the year to champion and lift up managers across the country.

Trend Or Issue Needing Manager’s Attention

Monopolisation and duopolisation of the wider industry, and speaking up about our concerns about it. It's leading to the enshittification of every aspect of music and touring, whilst everything else about it gets harder and more expensive.

Advice That’s Stuck

Focus on what you like doing, do it well, and surround yourself with people who are good at doing the things you don't like doing. I try to keep this in mind when the many roles of the manager start piling up (as they always do). It's important to pick your battles, and know when to bring in other team members to help. A strong team surrounding an artist leads to a highly adaptable and versatile platform from which careers are made. I'm super lucky to have a brilliant team around me.

Advice I’d Give My Younger Self In Artist Management

It’s worth it, but it's also worth it to rest. It's taken me a long time to realise I don't have to put the whole candle in the oven. That and maybe passing myself a note about the 2023 festival market collapsing and "hey you might have ADHD".

Key Achievements

1) Guiding Sly Withers to two ARIA top 10 album releases in Gardens (2021) and Overgrown (2022), and working on the third To Be Honest, out now.
2) Working with smol fish on their first ever headline tour - to Europe and the UK, as that's where we had signs their market was popping off.
3) Successfully bringing back the festival "Sidefest" in 2025, a collaboration between myself, Sly Withers and their booking agent, Casey O'Shaughnessy.

Inspiration and Motivation

I've been playing in bands and organising gigs since I was in high school, so I think at first I kinda stumbled into the management role of my own bands, and it snowballed from there. I began to take it seriously after Sam from Sly Withers sent me a lengthy message outlining why the band wanted to work with me, and if I'd like to be their manager. I was driving home from Christmas at the time, and I remember pulling over briefly to write "I'm driving, but yes!" and the rest is kinda history. The lessons I learned promoting my own hard-to-promote bands worked wonders on a band with actual marketability and talent!

I'm motivated by the magic that keeps us all engaged in the creative arts. A great song. A crowd singing along at the top of their lungs. A DM from a fan saying how a band you work with changed their life. That feeling in your stomach when you're just about to drop a new song/album/tour. I'm also motivated by my mates in the industry, who support me every day - whether it's sharing a joke, horror story or expertise that all remind me that whilst I generally work alone in mgmt, I'm surrounded by the best "co-workers" in the world.

A Passion Project

I'm just about to start building a house with my wife. It's been a huge process planning with our architect and builder, and a really different world to anything within my day-to-day. I know so much more about soak wells and tap hardware than I ever thought I would. If anyone's handy with a paintbrush, the beers are on me in 9-12 months time!