The Jacky Winter Agency

Can you tell us some hilarious stories about how you started out, early career disasters, and how Jacky Winter began?

Jacky Winter was a direct result of the self-initiated project I did with four others called Is Not Magazine Stuart Geddes and myself were the two designers on the project and we made a point to always commission great Australian illustrators and comic artists. Through these relationships I discovered a huge gap in the market with talent agencies. As a former editorial Art Director in my hometown of New York, I turned to agencies when trying to commission work for Is Not, however there simply weren’t any who were representing contemporary artists, so I went ahead and made one!
Fortunately there have been no major disasters (which I can share publicly!). One of my favourite things though is that there is a band in Melbourne called Jacky Winter – It’s a one man thing I think, and he’s pretty good too! – But he started out at the same time that we did, in late 2006. He play a lot of gigs and has his own merch, so we occasionally get to see the agencies name on the painted wall at The Tote, or shirts in gig photos, which is a bit hilarious.
There was also another time where I had to track down a photo release from an old book called ‘Know your Parrot’ for modification on the cover of one of our field guides. The original book was from the 60’s, and I somehow managed to track down the original photographer who was still living in New York and now in his 80s. The original photo shows a parrot sitting gracefully on the shoulder of a model. He told me that after he took the shot that the parrot totally went nuts and started attacking the model. That was an interesting conversation!
What was Jacky Winter like in the early days, and what major things have evolved into what it is today?
After our very first field guide was printed, I assembled them by hand. We didn’t have enough money to do a proper cover, and have it bound, so I made a slip cover and did them all that way. Then I loaded about 500 of them into an excessively large backpack, and travelled to Hong Kong, NY and LA, just passing them out at reception desks. That was around eight years ago, and honestly I think the only thing that has changed is that now we can afford international post!
Even though the agency has grown significantly, I like to think that our DIY attitude has remained intact to this day. We have always listened to our clients and evolved the nature of our offering so that we are consistently relevant, and my fierce sense of competition has really continued to drive us to succeed as a group, while still maintaining a very singular focus and vision in terms of our aesthetic and our unique voice. I think there has always been a sense of confidence that we had with the business from an early stage, and while there have been large changes in terms of growing staff, space, clients, and scale in general, I do think that it’s always been a natural evolution based on a response to both the marketplace of creativity – both with clients and artists, and we continue to take great pride in our work to grow our reputation and our practice.
Above: The Jacky Winter 2015 Field Guide - Cover artwork by Andrew Fairclough

What was Jacky Winter like in the early days, and what major things have evolved into what it is today?

Jacky Winter was a direct result of the self-initiated project I did with four others called Is Not Magazine Stuart Geddes and myself were the two designers on the project and we made a point to always commission great Australian illustrators and comic artists. Through these relationships I discovered a huge gap in the market with talent agencies. As a former editorial Art Director in my hometown of New York, I turned to agencies when trying to commission work for Is Not, however there simply weren’t any who were representing contemporary artists, so I went ahead and made one!
Fortunately there have been no major disasters (which I can share publicly!). One of my favourite things though is that there is a band in Melbourne called Jacky Winter – It’s a one man thing I think, and he’s pretty good too! – But he started out at the same time that we did, in late 2006. He play a lot of gigs and has his own merch, so we occasionally get to see the agencies name on the painted wall at The Tote, or shirts in gig photos, which is a bit hilarious.
There was also another time where I had to track down a photo release from an old book called ‘Know your Parrot’ for modification on the cover of one of our field guides. The original book was from the 60’s, and I somehow managed to track down the original photographer who was still living in New York and now in his 80s. The original photo shows a parrot sitting gracefully on the shoulder of a model. He told me that after he took the shot that the parrot totally went nuts and started attacking the model. That was an interesting conversation!

After our very first field guide was printed, I assembled them by hand. We didn’t have enough money to do a proper cover, and have it bound, so I made a slip cover and did them all that way. Then I loaded about 500 of them into an excessively large backpack, and travelled to Hong Kong, NY and LA, just passing them out at reception desks. That was around eight years ago, and honestly I think the only thing that has changed is that now we can afford international post!
Even though the agency has grown significantly, I like to think that our DIY attitude has remained intact to this day. We have always listened to our clients and evolved the nature of our offering so that we are consistently relevant, and my fierce sense of competition has really continued to drive us to succeed as a group, while still maintaining a very singular focus and vision in terms of our aesthetic and our unique voice. I think there has always been a sense of confidence that we had with the business from an early stage, and while there have been large changes in terms of growing staff, space, clients, and scale in general, I do think that it’s always been a natural evolution based on a response to both the marketplace of creativity – both with clients and artists, and we continue to take great pride in our work to grow our reputation and our practice.
Above: The Jacky Winter 2015 Field Guide - Cover artwork by Andrew Fairclough

As a creative, where did you learn to be so business savvy? Can you tell us about Jacky Winter Gives You The Biz (JWGYTB) and your favourite (business tips you took away from this years conference?

Above: Jacky Winter HQ, in Collingwood, Photography by Sean Fennessy

This was one of the hardest things about starting the business as there was just no information out there, we really had to cobble it together ourselves. You still can’t go to school to be an agent or a producer – it’s pretty old school in that way which is lovely in that you really have to learn it on the job or be passed the information down verbally.
Fortunately I had experience on the other side of things during my work as an art director, so I had a bit of information there – however from there I really did need to cobble things together. At first, professional societies like the Association of Illustrators in the UK were an invaluable resource. I also spent lots of time on forums and hearing about how agents worked with their talent. When it came time to learn about production, I looked to other creative industries such as the film and TV world, or even architecture, building, and more corporate-scale project management. You realise that many of these concepts are really universal if you can adapt them in relevant ways. As the business evolved so did the available information on the subject – Books like Stephen Heller’s were amazing resources, as well as the growing network of blogs and other online channels where information started to flow more freely.
In many ways I think we’re seeing an overabundance in education and information now – A big part of doing business though is simple common sense, plus a little compassion, and a whole lot of patience. It’s not just the raw info, but it’s really an emotional and psychological game on so many levels!
To that end, it’s been really exciting to share some of these nuggets of wisdom during our tour of JWGYTB – Especially seeing these things crystallized in a tidy package on screen. The info that the Media Arts Lawyers guys are giving away alone has been worth it’s weight in gold – I always learn something new when I speak with them and the way that they are able to retain and organise information as a legal practice is incredibly impressive!
As the Melbourne CreativeMornings (CM) host, who are some of your favourite creatives that have spoken at CM Melbourne and what did you learn?
I think Adele Varcoe was a real standout, just because of how she worked the room. It really was a special event and made the whole thing necessary to be there in person. I learned that it’s really challenging to stare at someone for an extended period of time, and it’s a diminishing skill!
Rohan Anderson was another favourite – I had literally never heard of him until CM, and his story really moved me. I think a lot of people really connected to him and his background in design and how he made a major change to follow his passion and lead an authentic life. I really did start to question and examine my choices in food after hearing about his journey. It also made me commit further to ensuring that we are bringing in people who stray from the normal design circuit!
Finally, Spencer Harrison up on stage was also really special. Spencer essentially started the chapter with me as our first volunteer and speaker liaison and it was really inspiring to see his journey from behind the stage to in front of it! I really learned how quick things move in our industry and how far you can propel yourself if you have the right mindset and dedication.
Above: Guy Shield and Pete McDonald for Drinkwise via Flutter

As the Melbourne CreativeMornings (CM) host, who are some of your favourite creatives that have spoken at CM Melbourne and what did you learn?

Above: Jacky Winter HQ, in Collingwood, Photography by Sean Fennessy

This was one of the hardest things about starting the business as there was just no information out there, we really had to cobble it together ourselves. You still can’t go to school to be an agent or a producer – it’s pretty old school in that way which is lovely in that you really have to learn it on the job or be passed the information down verbally.
Fortunately I had experience on the other side of things during my work as an art director, so I had a bit of information there – however from there I really did need to cobble things together. At first, professional societies like the Association of Illustrators in the UK were an invaluable resource. I also spent lots of time on forums and hearing about how agents worked with their talent. When it came time to learn about production, I looked to other creative industries such as the film and TV world, or even architecture, building, and more corporate-scale project management. You realise that many of these concepts are really universal if you can adapt them in relevant ways. As the business evolved so did the available information on the subject – Books like Stephen Heller’s were amazing resources, as well as the growing network of blogs and other online channels where information started to flow more freely.
In many ways I think we’re seeing an overabundance in education and information now – A big part of doing business though is simple common sense, plus a little compassion, and a whole lot of patience. It’s not just the raw info, but it’s really an emotional and psychological game on so many levels!
To that end, it’s been really exciting to share some of these nuggets of wisdom during our tour of JWGYTB – Especially seeing these things crystallized in a tidy package on screen. The info that the Media Arts Lawyers guys are giving away alone has been worth it’s weight in gold – I always learn something new when I speak with them and the way that they are able to retain and organise information as a legal practice is incredibly impressive!

I think Adele Varcoe was a real standout, just because of how she worked the room. It really was a special event and made the whole thing necessary to be there in person. I learned that it’s really challenging to stare at someone for an extended period of time, and it’s a diminishing skill!
Rohan Anderson was another favourite – I had literally never heard of him until CM, and his story really moved me. I think a lot of people really connected to him and his background in design and how he made a major change to follow his passion and lead an authentic life. I really did start to question and examine my choices in food after hearing about his journey. It also made me commit further to ensuring that we are bringing in people who stray from the normal design circuit!
Finally, Spencer Harrison up on stage was also really special. Spencer essentially started the chapter with me as our first volunteer and speaker liaison and it was really inspiring to see his journey from behind the stage to in front of it! I really learned how quick things move in our industry and how far you can propel yourself if you have the right mindset and dedication.
Above: Guy Shield and Pete McDonald for Drinkwise via Flutter

Where to find The Jacky Winter Agency online.

Above: James Gulliver Hancock environmental illustrations for CBA via Frost
Can you tell us about your multiple other side projects and how they began?
Where to even begin? The biggest one would be Lamington Drive, our physical gallery space in Collingwood which has been going since around 2008. That in itself has it’s own range of projects – from our fine art printing service, New Blank Document, to our own special projects like Lamington Drive Editions, which just put out the 1000 Colours Puzzle, now entering it’s third edition!
Recently, I have been seeing my side projects more and more tightly integrated with Jacky Winter, and not really as separate things. Even though people think we are just a rep, we are so much more. We really are our own creative studio in many ways. From our Children’s book with Thames and Hudson, to our Field Guides and conferences, it all comes back to the Agency and our Artists and our core services of production and contributing to the creative community.
(That said! There is one particular side project that is a bit of a left turn for us in some ways, that we are launching in July of this year. I can’t say much now, but if you follow us on Instagram or our newsletter, you can be the first to know!)
What advice do you have for design graduates finishing up in 2015?
Take dead aim on the rich boys. Get them in the crosshairs and take them down. Just remember, they can buy anything but they can't buy backbone. Don't let them forget it. Thank you.
Above: Bianca Bramham speaks at the Melbourne edition of Jacky Winter Gives You The Business
Above: Various Jacky Winter artists on display throughout the 1888 Hotel, Sydney
Above: The Jacky Winter Travelling Roadshow, currently on display at DDB Sydney
Above: Lamington Drive Gallery, in Collingwood, Photography by Sean Fennessy