Premium Members, click here to access this interview in the premium area.

Putting together an intro for celebrity portrait photographer, Jesse Dittmar of was one of the toughest ever – there's so much I want to include, but it'd take up the whole show!

Here's a taste…

Jesse is a commercial and editorial photographer based in NYC who has worked with clients such as The Washington Post, Rolling Stone, Vanity Fair, and Apple to name a few.

A lot of his work is centred around celebrity portraiture where he has photographed people such as Tom Hanks, Denzel Washington, David Letterman, Sting, Serena Williams and the cast of Star Wars to name another few.

His career took off after an assignment to photograph an actress for The Washington Post. Suddenly he was getting calls to shoot celebrities for Rolling Stone, the Village Voice and The Hollywood Reporter, and other magazines.

I'm guessing there was a lot more going on behind the scenes before that assignment.

On his website, he says – I take portraits of people who are affecting the world: artists, activists, journalists, athletes, politicians, musicians, and regular people too. He also says – I treat my portraits as conversations.

In this interview, Jesse shares his thoughts and experience on the business side of celebrity portraiture, working with photographers like Annie Leibovitz and sticking at it till your break comes – as it has for him.

Here’s some more of what we cover in the interview:

  • Jesse shares his experience working with Tom Hanks
  • How Jesse works with publications or known brands
  • How Jesse presents and shows his work to his clients before shooting
  • Photographing and working with celebrities – what's it like
  • The importance of knowing what you can control and what you can't in a photo shoot
  • Security considerations when working with any celebrity
  • How Jesse treats his photography as a conversation
  • Jesse's number one goal when shooting
  • How and why Jesse shoots film and digitals for his clients
  • Does shooting film today, attract more clients
  • Do clients always get a digital file that looks like film
  • How does copyright work when you are commissioned to do a shoot
  • Jesse's advice on being an assistant and working with well-known photographers
  • How Jesse was hired to work with Annie Leibovitz and became her assistant
  • The biggest break or turning point for Jesse's photography career
  • Working within the means available to you
  • Where does Jesse get most of his income
  • Thoughts on pricing and value for photography

Jesse Dittmar Photography Podcast

What’s on Offer for Premium Members

If you’re a premium member, you should have received an email with links to your version of this interview – the full length and more revealing version where you hear the absolute best tips and advice from every guest.

If you’re on the fence about becoming a premium member, join with the $1 trial today and get access to the FULL interviews each week, get access to an amazing back catalogue of interviews and ALL future interviews delivered automatically to your phone or tablet.

The goal of my pictures is the ability to represent people that are meaningful and the world in some capacity and put my spin on them. – Jesse Dittmar

Plus special member-only interviews.

You'll also receive access to the members-only Secret Facebook Group where you can connect with other Premium Members and interview guests to help, support and motivate you to take ideas you hear in each episode and put them into action. There are also FB live video tutorials, role-play interviews and special live interviews happening in the group.

You will not find more friendly, more motivated, caring and sharing photographers online.

Joining a Mastermind Group (encouraged by Andrew) has been incredibly valuable and fun, I look forward to connecting with my group members every week. Jina Zheng, Premium Member and Melbourne Children photographer.

And that's not all… you get a set of steak knives… I'm kidding!

Seriously though, that's not all. In addition to everything above, you'll get access to and instructions on forming or joining a MasterMind Group with other premium members. These groups are super motivating, make you accountable and build friendships with other pro photographers with similar motives to you – to build a more successful photography business.

Jesse Dittmar Photography Podcast

What is your big takeaway?

Following this interview, I’d love to know if you're taking anything away from what Jesse shared. Is there something you heard that excited or motivated you to the point where you thought, yeah, I'm going to do that! If so, let me know by leaving your thoughts in the comments below, let me know what your takeaways were, what you plan to implement in your business as a result of what you heard in today's episode.

It's more like the work I show is the work I want to be making and you get hired to take pictures you've already taken. – Jesse Dittmar

If you have any questions that I missed, a specific question you’d like to ask Jesse or if you just want to say thanks for coming on the show, feel free to add them in the comments area below.

Jesse Dittmar Photography Podcast

iTunes Reviews and Shout-outs

Each week I check for any new iTunes reviews and it's always a buzz to receive these… for a couple of reasons.

Firstly, it's confirmation that I'm on the right track with the interviews and that they really are helping you improve your photography business. That's awesome!

Secondly, iTunes is the biggest search engine when it comes to podcasts and it's your reviews and ratings that help other photographers find PhotoBizX. More listeners mean more interviews and ultimately a better show.

If you have left a review in the past, thank you!

If you haven't and you'd like to, head to and you can leave some honest feedback and a rating which will help both me and the show and I'll be sure to thank you on the show and add a link to your website or blog if you let me know the URL of your website and your name.

Alternatively, if you've left a review for PhotoBizX and are looking for more backlinks to help your SEO, leave a review for the new Photography Xperiment Podcast and email me your keywords or keyword phrase and where you'd like me to link to.

Another great way to get a backlink to your site is to send a video testimonial. It doesn't need to be fancy and your phone will be perfect. Click record and tell me how PhotoBizX has made a difference to you and your photography business.

Here is the latest review:

Lifetime Stories Photography

In iTunes by Brisbane maternity and newborn photographer, Victoria Burcusel on February 22, 2019

I am so grateful that I can listen to Andrew every night… doing a night shift and learning the best practices to run a business doesn't sound so bad now.

I have listened to 172episodess then decided to join him as I believed I was missing the best part. Now I need to go back and hear the entire interview and put them into practice.

I will start with the Facebook Ads and will let you know how I'm going.

Thank you for the podcast.

Jesse Dittmar Photography Podcast

Giveaway to test messenger bots

I've put together a PhotoBizX giveaway on Facebook to test a few things with messenger bots.

  1. Can I make the whole bot experience feel like you're talking to a real human – to me?
  2. Can it be fun?
  3. Can it be profitable?

The answer to the first two questions are a resounding YES!

To prove it, check out the giveaway and my bot experience here:

As for thing #3 – being profitable?

I'll update you on how this whole thing plays out but the response has been great with comments like this one…

That was the most fun bot experience ever! Up until now, any I've encountered have been pretty dry and uninspiring and feeling a bit intrusive. This one shows what can be done and making me open up my mind to trying it myself! – Ruth Brown

And this…

Hey Andrew 👋just wanted to say that the messenger bot setup is killer!” – Michael Conlin

Back to the 3 things I want to learn from this bot test.

  1. Can an experience with a messenger bot really feel like you're communicating with a human where it's actually fun and engaging?
  2. Can a photographer use a messenger bot to generate new leads, bookings and sales?
  3. Can utilising a bot in your photography business be massively profitable when running campaigns and promotions?

I'll come back and share exactly the kind of promo you could be utilising a bot in your business this week, but to get an idea of what I'm talking about, and to get you thinking, you need to experience what I'm talking about.

Click the link to try it out –

Jesse Dittmar Photography Podcast

Links to people, places and things mentioned in this episode:

Jesse Dittmar Website

Jesse Dittmar on Instagram

Two the Book by Jesse Dittmar

Messenger Marketing for Photographers – Nice Chat Let's Book

Starving Artist to Well-Compensated Creator Registration – The Busienss of Pet Photography

Thank you!

Thanks again for listening and big thanks to Jesse for sharing his thoughts on photography, shooting, business, branding, style and his big break into the world of photographing celebrities and famous people of the world

My first immediate job is to prove that I'm up here and that my work is good and hopefully we're doing something that is going to be mutually amazing. – Jesse Dittmar

If you have any suggestions, comments or questions about this episode, please be sure to leave them below in the comment section of this post, and if you liked the episode, please share it using the social media buttons you see at the bottom of the post!

That’s it for me this week, hope everything is going well for you in life and business!

Thanks and speak soon