Investing prior earnings into music

Jacinta and Jesse from JC and the Tree have built their version of freedom, in music and in life. They have 3 years of touring Australia to prove it. From the road, gig by gig, they've had a a red hot crack at running a fully DIY music business while travelling Australia.

This is a grounded look at what that actually takes: long drives, small crowds, constant admin, and making the numbers work through gigs, merch, and multiple income streams. They share how they stay organised, why community matters more than scale, and the trade-offs most people underestimate.

It’s a bit romantic, and a lot about being practical, disciplined, and deliberate. A useful and entirely motivating case study for anyone thinking about taking the leap to 'do a lap' and maintain or indeed start a new business.

The message - get out and have a crack! Here's a couple of tracks to get your trip started.

Outrun the Sun

Wide Open Plain

Made to Roam

Main Insights:

• The daily grind of touring they call “no routine,” balancing gigs, admin, and sanity
• How small shows foster a strong community and why passion outweighs crowd size
• The leap from traditional jobs to full-time artist on the road, fueled by necessity and dreams
• The art of DIY—building a van, managing finances, marketing, and staying organized
• Income streams: gigs, merch, streaming struggles, and the promising world of sync licensing
• The mental health camaraderie among musicians on the road and the importance of support networks
• How living minimally on the move enhances life and art
• The future of independent artists: adaptability, passive income, and making space for creativity
• Policy fixes for small businesses, echoing the duo’s call for fairness and ecosystem support

Timestamps:

00:00 - The transformative power of living and working in a DIY artist community

01:02 - A typical day on the road: exercise, driving, gigs, and admin chaos

03:43 - The magic of small crowds: intimacy and authenticity in live music

05:08 - Moving from full-time jobs to chasing music dreams: risk, burnout, and breakthroughs

07:55 - The real costs: gear, recordings, and building a sustainable music business

09:11 - Breaking free from expensive rent, embracing a van life for freedom and purpose

13:13 - Skills beyond music: craftsmanship, bookkeeping, and digital literacy

17:50 - Streaming vs. traditional income: the harsh realities and future promises

21:28 - The potential of sync licensing—turning creative work into passive income streams

25:44 - The resilience of community: mental health, support, and the shared journey

27:23 - The evolving Australian live music scene: opportunities for indie musicians

29:42 - Challenges of balancing passion, business, and personal wellbeing on the road

36:35 - The pros and cons of platforms like Bandcamp, Spotify, and the quest for fair revenue

42:43 - Artistic passion vs. business acumen: living the lifestyle and sustaining the craft

51:45 - Imagining policy initiatives: fairness, tax accountability, and supporting small businesses

55:12 - Final words: the importance of community, resilience, and bold choices in art and life

Resources & Links:

• Michael West Media - Investigative Journalism on Tax Cheats
• Spotify Streaming Platform
• Bandcamp for Artists & Musicians

JC and the Tree 

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Thanks for listening.  Visit the Owner To Owner Podcast website to subscribe, listen back, or check out any resources or information mentioned on the show.

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Reach out to Michael Kerr via the website if you need personal assistance or advice for your small business.

michael.kerr@kerrcapital.com.au

www.ownertoownerpodcast.com.au