“I’m actually showing people through these images, who they were born to be.”
Daniel Wakefield
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Daniel Wakefield has a folder on his phone he’s never shown anyone.
It’s called “bad headshots.” Screenshots pulled from LinkedIn: cropped wedding photos, blurry cell phone selfies, the kinds of images that make you wonder how someone decided this was the face they’d put forward to the professional world. He doesn’t share it. He just keeps it. A private record of everything his work is trying to fix.
It’s a telling detail, because Daniel is the kind of person who notices things like that. He came to photography the long way around, through a biology degree, a career teaching high school science, and a move to South Florida that put him close to the alligators and wilderness he’d always wanted to photograph. Wildlife led to portraits. Portraits led to headshots. And headshots led somewhere much deeper than he expected.
Today Daniel runs Top Tier Headshots, a premium headshot and personal branding studio in South Florida. His clients are founders, executives, attorneys, and corporate professionals. His goal isn’t to give them the best photo they’ve ever taken. It’s to show them who they’re going to become. Clients walk in convinced they’re not photogenic and leave in tears when he turns the laptop around. That doesn’t happen by accident. It happens through coaching, genuine connection, and a philosophy of client service that runs through everything he does.
That philosophy eventually became a book. Accelerate covers the mindset shifts and practical strategies that took his business from zero to six figures in its first year, centered on what he calls the power of genuine connection. It’s also led to a coaching program for photographers trying to build something sustainable, and a partnership with headshot photographer Peter Hurley.
In this conversation, Daniel and I get into all of it.
Here’s some of what we cover:
- Why most headshots still look like school picture day, and what it actually takes to change that
- The first business that crashed and burned, and what he did differently the second time
- How LinkedIn became both his primary marketing platform and his biggest source of new clients
- The mindset shift that separates photographers who grow from those who stay stuck
- What happens in the studio when a client sees themselves clearly for the first time
- The hype tornado, and how to turn clients into people who can’t stop talking about you
Daniel moves between science and art, introvert and networker, photographer and business coach, and makes every version of it feel like the same person. That consistency is exactly what he teaches. Hope you enjoy the conversation.
Q: You had a photography business before Top Tier Headshots. What happened to it?
Daniel: In that first business attempt, I never got a single client that wasn’t already a friend or family member. I was basically chasing the bottom of the market, trying to be the cheapest person, just all the stuff that is not really a great strategy. I think that really highlighted the fact that I did not know what I was doing from a sales and marketing perspective.
Q: What actually happens when a client sees their headshot for the first time on your tethered laptop?
Daniel: You get reactions of absolute joy that they can’t believe how amazing they look, or moments of speechlessness where people who are normally super chatty are at a loss for words. I had a big-time executive vice president of a major global bank come in for a quick 20-minute session. I took like five shots, captured this moment of calm confidence in her, flipped the laptop around, and she started crying. She said, I can’t believe that’s me. What I realized is I’m not just creating pretty images. I’m actually showing people, through these images, who they were born to be.
Q: AI headshot tools are getting better all the time. Does that threaten your business?
Daniel: Since the development of AI headshots, my business has actually gotten busier, not less busy. It doesn’t matter how good they look. When you opt to use an AI headshot instead of a real one, you’re putting a barrier between you and the people you want to connect with. There’s a missed opportunity, because the imperfections that make you who you are actually increase your power to resonate with people, whereas AI wants to make you quote unquote perfect. Humans have flaws. And that, in a sense, is an asset when connecting with other people.
🔗 Connect with Daniel Wakefield
🧭 What We Talked About
🎓 Early Journey / Origins
- Daniel came to photography through a lifelong love of wildlife, which led him to a biology degree at York University in Toronto and a career teaching high school science.
- He picked up his first DSLR around 2004 or 2005 after a friend offered it to him for $500, but it sat largely unused until he and his wife moved to South Florida in 2015.
- Once in Florida, he started making regular trips into the Everglades to photograph alligators and local wildlife, quickly realizing how far his skills had to go and becoming driven to close that gap.
- A friend who moonlighted as a photographer introduced him to manual mode, which opened up the creative side of the medium and pushed him deeper into the craft.
- He began building an Instagram presence, placed well in international wildlife competitions, and got published in books and magazines, but wasn’t sure how to turn any of it into a sustainable career without sacrificing family life.
📖 Accelerate – The Book and Coaching Program
- About two and a half years into Top Tier Headshots, with the business running at multiple six figures annually, other photographers started reaching out unprompted to ask how he was growing so fast.
- After enough of those conversations, and after people started offering to pay him for his time, he and his wife decided to formalize it, starting with a book.
- Accelerate was written over roughly 10 months, published about a year ago, and covers the mindset traps that hold photographers back as well as the practical steps that took Daniel from zero to six figures in his first twelve months.
- He runs a joint business workshop with Peter Hurley alongside headshot intensives, and has built an ongoing coaching community that has now been running for about a year and a half with members flying in for in-person sessions.
- The book has found an audience beyond photographers, with business owners and executives telling him they found value in it, which he sees as confirmation that the ideas hold up outside the photography industry.
📸 Headshots – The Craft and Philosophy
- Daniel describes most headshots in the market as the photographic equivalent of school picture day, and has built his practice around an aspirational alternative, something that looks like it belongs on the cover of Forbes.
- At least 80% of his clients arrive telling him some version of the same thing: they are uncomfortable in front of the camera, don’t feel photogenic, and rarely like photos of themselves.
- His expression coaching is roughly split between technical direction, things like posture, eye positioning, and the jawline trick popularized by Peter Hurley, and what he calls the art of misdirection, using humor and unexpected moments to surface authentic expressions.
- He shoots tethered to a laptop so clients can see the images almost immediately, which he finds dissolves nerves faster than anything else he could say to reassure them.
- He describes moments where clients have been moved to tears seeing themselves look calm, confident, and genuinely like themselves, and sees this as the deepest part of what the work actually does.
- His goal with every session is not just a great image but something aspirational: showing clients not who they are today but who they are capable of becoming.
🔮 What’s Next for Daniel
- He is rolling out a new premium offer aimed at founders, executives, and speakers, built around what he calls signature keynote portraits, a studio recreation of the in-action speaking shots that most speakers struggle to capture well at live events.
- The offer also includes behind-the-scenes photography and brand-building video content, moving Top Tier Headshots toward a fuller personal brand package rather than headshots alone.
- Longer term, he is moving toward offering personal brand consulting as a standalone service, drawing on what he has already been doing informally with photography clients who have the credentials but not the platform.
