Today we’d like to introduce you to Chad Isaiah.
Hi Chad, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
The creative gene runs in my family — my grandfather was an avid hobbyist photographer, my uncle played accordion, and I spent my high school years at a piano. Photography got serious in college where I was one class short of a photography minor because of a scheduling conflict, and for years after that it stayed a hobby.
When I relocated to Pittsburgh in 2018, I started photographing for my local church. Through my church, I ended up photographing weddings for a year and finally in November 2022 I took my first paid headshot and I fell in love with the complexity of photographing someone so close and realizing the impact that headshot was going to have on their career and earning potential. For the entire next year, I worked remotely with Peter Hurley in NYC, widely considered one of the best headshot photographers in the world and eventually became one of his Associate Photographers in January 2024. A few months later in May 2024, I quit my day job and went all-in on my headshot photography business.
Today, Chad Isaiah Studios operates out of the Brookline neighborhood in Pittsburgh, PA. We specialize in professional headshots, conference event photography and headshot booths for conferences and tradeshows. We have over 580 5-star Google reviews (all earned in just over 3 years) and were named the Monroeville Area Chamber of Commerce’s 2025 Small Business of the Year.
My whole approach comes down to one thing: I photograph people who don’t like being photographed. No forced smiles, no awkward posing — just genuine connection and maybe a few terrible jokes.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
It definitely has not been a smooth road. I went from a steady paycheck to business fluctuating with the seasons. We think of wedding photographers as having seasons, but headshots, especially for working professionals, are also seasonal as many go out of town during the summer. So finally deciding to take the leap was rough.
One of the biggest struggles was learning how to run a business on the fly. I had trained to be a great photographer, but the art is only part of it – the business still needed to run. Growing up I never had any entrepreneurial role models to look up to, so it was important for me to find a local group of small business owners to toss ideas around with.
An ongoing struggle is AI and how it’s changing not only photography, but the business landscape as well. AI headshots were becoming a thing as I took my business full-time, and that pressure has never stopped because our studio is a premium experience with a premium price – and that doesn’t compete well against $15 headshots from an AI software.
As you know, we’re big fans of Chad Isaiah Studios. For our readers who might not be as familiar what can you tell them about the brand?
Chad Isaiah Studios is a headshot and event photography studio based in Pittsburgh’s Brookline neighborhood. We do three things: professional headshots (in-studio or at your office), conference and event photography, and headshot booths for tradeshows where attendees step in front of the camera and have a polished, professional headshot delivered to their phone within minutes, before they’ve even left the expo floor.
What we’re known for is the anti-awkward experience. Most people would rather get a root canal than sit for a headshot. They show up stiff, apologizing, insisting they’re “not photogenic.” My job is coaching them past that, which is a directing skill, not a camera skill. It’s also the thing I trained hardest on. I’m a Headshot Crew Associate Photographer under Peter Hurley, the highest certification in headshot photography. Only 180 photographers worldwide hold it, and I’m the only one in Pittsburgh.
What sets us apart beyond that: I treat a headshot as a business tool, not a piece of art for my portfolio. The question I’m answering isn’t “is this a beautiful photograph?” but “will this image help you get hired, promoted, or chosen?” That mindset changes everything about how a session runs. Nobody leaves with an image they don’t love, because an image you’re embarrassed to post is worthless no matter how well-lit it is.
Brand-wise, I’m proudest of two things. First, our 580+ five-star Google reviews, earned in just over three years, most of them from people who walked in dreading the camera. Second, that we’ve built this as a Disability-Owned Business Enterprise (Disability:IN), and were named the Monroeville Area Chamber of Commerce’s 2025 Small Business of the Year.
For readers: if you or your team have been putting off new headshots because the last experience was miserable, that’s exactly who we built this for. And if you run conferences or sponsor tradeshow booths, the headshot booth is the busiest activation on any expo floor since people line up for something genuinely useful, and sponsors get the traffic.
Can you talk to us a bit about the role of luck?
I think luck is what we make of our situations. Originally I was never planning on moving to Pittsburgh 8 years ago, but circumstances changed and I ended up here. If it weren’t for that random circumstance changing, then I would have never met my partner who convinced me to try my luck and start a business.
I also lucked out in that I started my business after the pandemic. Pre-pandemic, headshots were still thought of as something for actors, but afterwards, the landscape changed and zoom calls and remote work became more important. And thus someone’s digital presence (and by extension their headshot) became more important.
But while these events might have been lucky, or unlucky depending on how you frame it, nothing beats the hard work that was put into all of this and finding ways to adapt to the situation.
Pricing:
- Headshots start at $300
- Event photography starts at $250/hr
Contact Info:
- Website: https://www.chadisaiah.com/
- Instagram: https://instagram.com/chadisaiahphoto
- Facebook: https://facebook.com/chadisaiahstudios
- LinkedIn: https://www.linkedin.com/in/chadisaiah/
