If you like doing photography and you’re not getting paid much, imagine doing photography and getting paid a lot for it. It’s way better.
Jon Meadows
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Jon Meadows wasn’t looking to make art when he started photographing bugs in Louisiana. He was just trying to avoid being eaten alive by them. With a camera in one hand and a swarm of insects in the other, Jon honed his skills on whatever didn’t fly away-and if it did, there was always another one nearby. It wasn’t glamorous, but it taught him to see light, shape, and timing. And slowly, something clicked, and people became his focus.
Fast forward a few years and Jon now runs High-End Headshots from a studio in, yes, his basement. But don’t let that fool you. His portraits are sleek, honest, and wildly effective. He’s built a career helping professionals look and feel confident in front of the camera-and he’s helped fellow photographers do the same through his own business mentoring program.
In this episode, Jon shares how he went from photographing poisonous moths to being one of the most sought-after headshot photographers in D.C. He talks about pricing without apology, why he refuses to sell packages, and how learning to read faces changed not only his work but the way he sees people.
Here’s some of what we get into:
- The unusual (and slightly nerve-wracking) story behind his first-ever client shoot
- Why most photographers undercharge-and how to build a pricing model that actually works
- His philosophy on facial expression coaching, and how it helps clients drop their guard
- Tips on building trust before the shutter clicks-and why he insists on a phone call before every booking
- The unexpected shift in how Jon sees human beauty, and what photography taught him about presence
Jon’s approach is refreshingly direct, deeply thoughtful, and rooted in real-world results. If you’ve ever struggled with confidence-your own or your client’s-this one will hit home. Enjoy!
Q: What are some key indicators of what people should be looking at when they are pricing out their services for headshots?
Jon Meadows: Will your average with all of the kinds of things you do, kinds of genres you shoot, get you to where you want to go? People think, wow, $1,000, that’s a great day. But $1,000 a day won’t get you to half a million dollars. So if your goal is half a million, then $1,000 a day is not a lot. You’ve got to factor in taxes too-if you make $1,000, you’re really getting about $600. You need to pick a price and stick to it. Don’t haggle or try to charge differently based on who the client is.
Q: Why don’t you recommend offering packages for headshot sessions?
Jon Meadows: Packages limit people’s plans for buying more images. If you say, “You can get one or five or ten,” then very few people buy more than ten because you’ve basically told them that’s the max. I’ve had people spend $10,000 in one session-if I had limited them with a package, that wouldn’t have happened. I do a session fee, and then clients buy images à la carte. I’ll offer them options if they want to buy more than they expected, but it keeps things open and aligned with doing a good job every time.
Q: How do you help clients align their headshots with their personal or professional brand?
Jon Meadows: Most of my clients aren’t coming to me with a strict spec-they’re coming to me because they want their headshots to look like mine. I do get some requests to match a certain lighting setup, and I’ll do that if they’re paying what I charge. But often, it’s more about doing a rebrand. These are usually teams of five to twenty people who want my style. So they’re not hiring me to copy another photographer’s look-they’re hiring me for me.
🔗 Connect with Jon Meadows
Making Bank With Photography (Course)
🧭 What We Talked About
🎼 Early Journey / Origins
- Jon’s story kicked off during a semester abroad in London, where he was snapping tourist photos to show friends and family what he was seeing. Nothing fancy-just curiosity and a camera.
- A passing comment from his mom-“you might be good at photography”-stuck with him for six years. Eventually, that seed sprouted.
- His first “subjects”? Bugs in Louisiana. From there, he moved to real estate shoots… and then somehow ended up photographing a top White House legal counsel with a Nikon D3400 and a paper towel-diffused speedlight.
📖 Philosophy / Vision / Storytelling
- Originally hesitant to photograph people, Jon now thrives on capturing authentic expressions-and it’s completely shifted how he views beauty and human connection.
- “Anything that looks real and human is cool.” That simple idea shapes his entire practice.
- He’s known for facial expression coaching, which he calls “the end of not liking your own photos.” It’s personal, practical, and confidence-boosting.
📷 Tools, Gear, and Behind the Scenes
- Started with entry-level gear, now shoots fully tethered in his basement studio-which, according to colleagues, is “a very, very nice basement.”
- Uses Capture One for live reviews with clients during sessions.
- Jon doesn’t believe in boxed-up packages. Instead, he charges a session fee and lets clients buy images à la carte, based on what they actually love.
🔁 Practice, Teaching, Platforms
- Jon shares generously in his Facebook group, where he’s built a strong peer community around headshot success.
- He’s a longtime member (and now mentor) in Peter Hurley’s Headshot Crew, which he credits for most of his technical growth.
- LinkedIn is his marketing playground-where most of his clients find him through mutual connections, not ads.
💬 Advice, Creative Strategy, or Challenges
- Pricing is a huge focus. He encourages photographers to start with a yearly income goal, break it down into session types and averages, and build their pricing from there.
- He’s not a fan of haggling or tailoring prices per client. “You get the clients you get-and you don’t get the ones you don’t.”
- Perhaps most importantly: “Don’t sell what they need. Sell what they want.” His sessions are about listening closely and letting clients guide the experience.
🌍 Influences, People, Brands, or Places
- Big nod to Peter Hurley, whose critique helped sharpen Jon’s skills early on.
- Gear and tools include: Nikon D3400, Capture One, Square app for booking/payment, and plenty of DIY lighting in the beginning.
- A surprising source of inspiration? Formula One drivers-specifically how they handle complexity and focus at high speeds. It’s how Jon thinks about managing light, rapport, and timing all at once during a shoot.
🔮 What’s Next for Jon
- He’s considering developing a new facial expression coaching course, though he admits it’s tricky to teach since it’s so personalized.
- Continuing to mentor through his Making Bank system, Facebook group, and tutorial series.
- Personally? He’s taking a break with two big trips: a family getaway to Nantucket and a 10th anniversary trip to Paris and London with his wife-no work, just travel, connection, and recharge.
