AMA Recap: Illustrator and Podcaster Andy J. Pizza

Last week we held a live “Ask Me Anything” interview with American illustrator and Creative Pep Talk founder, Andy J. Pizza aka Dr. Pizza! Andy is someone we’ve followed for years and while he’s made things for Nickelodeon, Amazon, The New York Times, and been featured by the likes of Apple and Buzzfeed, one of Andy’s greatest skills is helping fellow creatives!

Channeling his infectious positivity and industry know-how into 250+ episodes of insights, interviews, and practical tips, Andy graciously took time out of his busy schedule to respond to specific questions from Instagram and our Booooooom Slack Community! Discussion ranged from dealing with ADHD, advice for new freelancers and, of course, pizza! Check out some of the highlights from the AMA below along with some images created by some of the members who asked him questions.

Levi: What are the biggest changes you’ve seen over the last few years when it comes to balancing being an artist and an entrepreneur? What does a creative definitely need to do now, or focus on, that they maybe didn’t a few years ago when you first started your podcast?

Also, who is your “white whale” guest on your podcast? Someone you really really want but haven’t managed to get them on yet.

Andy J. Pizza: I think the whole idea of building a creative business on a SUPER SMALL but DEEPLY PASSIONATE fanbase is the way forward these days. Kevin Kelly’s whole 1000 true fans if you will. With patreon and all the platforms out there, there are so many ways to make this work for you!

AS FOR MY PODCAST WHITE WHALE: I’d love to have Abbi Jacobson on as she trained as an illustrator at MICA before going to acting and the trajectory there is super fascinating… so if anyone knows her, hook me up!

Jeff: How exactly does one get a pizza PhD?

Andy J. Pizza: HAHA!! It’s hard to explain but I CAN tell you it requires many types of dipping sauces, a vast knowledge of toppings from arugula to goat’s cheese, and what’s known as the second pizza stomach AKA the ability to eat unexplainable amounts of pizza without getting full!!!

Taylor Carroll: When did you know it was time to quit your full time job? or you were mentally ready to freelance?

Andy J. Pizza: HUGE QUESTION. Before I left my job I read this book called “Quitter” by Jon Acuff. It’s really good and answers a lot on this subject. ONE of the big takeaways was that the most surefire way to make that transition as smooth as possible is only leave your job when you absolutely can not keep up with it any longer because of the freelance overwhelm. That season of hustling on both fronts was not pretty but it allowed me to make the transition in such a way that it was less of a LEAP of faith and MORE OF A STEP OF FAITH!

Artwork by Joshua Barrigada

Joshua Barrigada: Me and a few artist over here are new to the freelance artist life. Most of my work has been local smaller jobs, but I want to jump into better paid international work, do ya got any hot tips on baby stepping your way into bigger illustration and art jobs?

Andy J. Pizza: EARLY ON I think for me it helped me to make a public portfolio for the work I wanted to do that applied to small and big companies and then a secret PDF portfolio of work that I COULD do for smaller local companies that helped keep the lights on but didn’t want to water down my main portfolio with. The main thing is to create a portfolio that shows the kind of work you want to get hired to do!

ON TOP OF THAT I recommend finding a weak point of entry into those bigger markets. Find a client that has LOW VISIBILITY but HIGH CREDIBILITY. Meaning it’s not well known and therefore is not bombarded with tons of direct promo BUT it’s highly regarded by the people in the industry who really really know their stuff. FOR INSTANCE: in the music world, I got my start working with bands by approaching the small bands that had super critical acclaim, these bands were the favorite bands of my bigger favorite bands. They were accessible but prestigious! This helped build my rep.

Joshua Barrigada: What’s the best pizza you’ve had while on the road as a speaker?

Andy J. Pizza: Emmy Squared in brooklyn probably!! SUPER GOOD DEEP DISH.

Jeff: What pizza toppings are you NOT down with!

Andy J. Pizza: No pineapple. I just can’t get down with that… I’m also not CRAZY about chicken on pizza… although that’s just because I got food poisoning from chicken years ago and I can’t risk that kind of pizza trauma or potential aversion. My whole career will be derailed!!

Jeff:  You can blame Canada, specifically Ontario, for inventing Hawaiian pizza.

Andy J. Pizza: OH CANADA! I LOVED YOU SO MUCH…. but now you are dead to me!!!!!

Artwork by Abhishek Joshi

Abhishek Joshi: Do you have any advice for new freelancers on how to find and approach creative agencies/prospective new clients? Or just a way to expand current pool of contacts let people know you are available for freelance work? Especially to expand outside of your hometown/city.

Andy J. Pizza: First of all I recommend that you don’t go unarmed!! In my favorite game Zelda: Breath of The Wild you can go to the main boss right at the start of the game, but if you do, you will get your butt kicked. You have to go get the master sword and arm yourself with a bunch of weapons before you can beat him.

The same is true in your creative work. As an illustrator you can’t just email the New York Times and get work from them. You have to arm yourself with the right weapon. A weapon perfectly designed to take down that boss.

FOR ME this means developing strategic side projects (I call them side quests) that mirror the client work I want to get hired for. SO that means making my own magazine or zine that has articles on topics the NYT covers and illustrating them myself. THEN sending that to the NYT.

SOOOO find a niche that has lots of clients you want to work for, design personal work that is SUUUPER targeted and then approach them with relevant stuff they actually might care about. That’s the best way I’ve done it!

Jeff: Successfully doing what you love for a living is not easy, what are the most common reasons people fail at it? Maybe this relates to what you’ve said about your biggest enemy being in your own head?

Andy J. Pizza: I think the most common reason people fail is found in something my dad says: “Life is hard, but that doesn’t mean it’s bad, hard and bad are not the same thing.”

I think that we almost all have a FIXED MINDSET that says if I am going the right way it should be easy, when in fact OFTEN it’s the opposite! If there are still booby traps the treasure is still there!

Artwork by Mark Sarmel

Mark Sarmel: Mentorship is something that really seems to have fallen by the wayside. Did you have a mentor in your life? Also, any ideas on bringing creative mentorship back into fashion?

Andy J. Pizza: I had a lot of people who I considered to be digital mentors. Folks who were just a few steps ahead of me who I would reach out to via email and get a hand when I needed it. They were instrumental!

I really want to build a community in the near future with the ability to take classes with creative super stars that doesn’t require insane debt from art school. Getting rid of the high overhead of brick and mortar and massively reducing the admin costs should be great for both students and teachers!!

Katie: I love your podcast. My question is: Are you coming to ICON 2020?


Kimi: In one of your recent podcasts (I think the one about finding your style) you really hit on the fact that creativity takes bravery. Can you share a time when you were really scared? And how it went?


I was actually really scared to drop my new Skillshare class. It’s a lot more philosophical and theoretical than most of the stuff that works on that platform. Mostly it’s HARD TECHNICAL SKILLS and although I completely believe in the content, it felt risky to make that bet.SO GLAD I DID because it’s crushing my expectations!!!!

The work of LIZ GILBERT and STEPHEN PRESSFIELD have really helped me start seeing FEAR in my creative practice as sign posts that say Im going the right way rather than the opposite!

Jeff: I loved your collaboration with Hitrecord and wanted you to see if you would answer two of the questions that you posed to the community there — What’s the creative advice you needed to hear 5 years ago? And what creative advice might “you from 5 years into the future” give yourself now?

Andy J. Pizza: The creative advice I needed to hear 5 years ago was this: THAT’S NOT STRESS IT’S STAKES and STAKES MAKE THINGS INTERESTING! I think I was trying a bunch of new things and taking some risks and I was really feeling the weight of it and letting it get me down. Looking back I realize that the stakes just meant I was doing stuff that matters to me and that those same stakes are what keep this job from being BORING!!


Artwork by Graeme Zirk

Graeme Zirk: You speak really candidly and well about having ADHD and working independently as an Illustrator. These are things we share in common and I’d like to thank you for your service. You have clearly found a way to make neurodiversity work in favour of you and your practice. Consistency can be a really tricky thing when focus and calm are an inherent moving target. How have you managed to keep things consistent and on point in respect to your work and how you actually get the work done?

Andy J. Pizza: Let me start by saying: I still kinda suck at this.
Two weeks ago I let this new piece of personal work totally derail my deadlines and it meant that the next week I was having to get up at 3am and 4am to meet deadlines and it was a mess. SO take this advice with a grain of salt :stuck_out_tongue_winking_eye: HOWEVER I HAVE got better at this. HONESTLY I think it’s two things: a growth mindset and healthier living.

GROWTH MINDSET: I’ve been working on my habits for the past decade like a madman. I make very very incremental progress. OFTEN very 3 steps forward 2 steps back kind of thing. BUT compounded over time, it means that 10 years ago I was a chainsmoking pizza addict who was constantly late and generally a mess.

TO NOW I haven’t smoked in YEARS, lost lots of weight, started running and living a pretty tight routine most of the time.

NONE of it happened quickly, I failed a ton and still do and none of it came naturally. but this neverending dedication to growth and believing I could change has lead to me being a dramatically different person over time!

Annette Womack: Your candidness about your ADHD was a big thing for me because I struggle with it too. But after listening to you, I almost look at it as a super power 🙂

My question for you is about time management. Can you walk me through a typical day of yours? How much time do you spend on various projects and tasks and balancing work/family life and all of it? What works best for you, a little bit of everything everyday or attempt to focus on one major project at a time?

Andy J. Pizza: SOOOO I usually wake up around 6am and read and plan my day, review my schedule, etc.
7:30 – 9am I help my three kids get to school. YES 3 KIDS! YES IT IS INSANE
9AM – 1PM – Creative work, sometimes planning podcast, sometimes working on books or client work
QUICK SMALL LUNCH somewhere in the 1pm to 2pm range
3PM to 5PM – emails, phone calls, podcast interviews, meetings!!!!
AFTER 5PM I am 100% family man. IF I have more than I can do, I don’t pull all nights I get up SUPER EARLY like 3 or 4 am. I usually have one or two days a week where I am getting up at 4 or 5am to finish something!

Hayworthdesign: What do you do to recharge when you’re feeling drained from your busy life?

Andy J. Pizza: whiskey… pizza. I actually mostly don’t drink during the work week… mostly… haha. BUT I am OBSESSED with taking baths. I know it’s weird. ON SUPER STRESSFUL DAYS I TAKE TWO BATHS!!

Jeff: We are almost out of time… I wanted to squeeze in maybe a couple last questions here! I’m wondering if you have any thoughts on people who have ideas VS people who go out and do things (they are not the idea people but they actually execute)?

Andy J. Pizza: Telling people ideas you haven’t done is essentially telling people stories you haven’t lived. SUPER BORING and ANYONE CAN DO IT. IN FACT ANYONE CAN actually DO THE IDEA but VERY FEW PEOPLE DO!

My buddy Kyle Scheele is a pro public speaker and basically his life is coming up with RIDICULOUS IDEAS and THEN DOING THEM so he can then go tell the story on stage.
RIGHT NOW he’s about to burn an enormous (like 15 ft tall and 20 foot wide) viking ship made out of cardboard full of cards with thousands of people’s regrets written on them. WHY??? He had the idea. So he did it.

He told me that his dad did a bunch of silly things growing up and he’d always asked ‘why did you do that dad’ and his answer would always be: seemed like the thing to do at the time! I believe that’s the only reason you need to DO YOUR IDEA.

WE OFTEN DON’T ACT because we over think things! WE SAY IS THIS THE RIGHT IDEA??? AND THERE IS NO WAY TO KNOW so we just never do it!!! INSTEAD I’ve started asking: IS THIS THE IDEA THAT SEEMS LIKE THE THING TO DO AT THIS TIME? If the answer is YES. DO IT!

Jeff: Ok final question! You have a superhuman ability to recall the most amazing quotes. I’ve written down so many that you’ve mentioned over the years. If you were to be known for one quote, what would it be? (at this point in your life)

Andy J. Pizza: I will probably butcher this now… haha but here it goes!

“The real question is wether you’re going to be able to say a big hearty yes to your adventure” -Joseph Campbell

TO ME this is what life is about – all the crap and opportunity that’s thrown at you. ALL OF IT are you going to say NO to life and live cynical and jaded OR are you going to SAY YES and stay engaged and soft hearted!!

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