We’re excited to introduce you to the always interesting and insightful Daniel Wakefield. We hope you’ll enjoy our conversation with Daniel below.
Hi Daniel, thanks for joining us today. What were some of the most unexpected problems you’ve faced in your business and how did you resolve those issues?
When I started my business, I have to admit that I probably had too idealistic an attitude about getting clients. I assumed that if my portfolio was good enough, I could just put out a nice looking website and people would start booking.
Wrong.
My first full month in business, I made $60. It was truly a wakeup call.
What those early months taught me is that I can’t wait around for clients to find me. I need to get out there and find them.
I started to do this through in-person networking and LinkedIn. I began focusing on building relationships with people instead of just selling them on my services. And over time, this proved to be one of the secret sauces for an increasing number of referrals and growing a thriving business.


Daniel, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
My name is Daniel Wakefield, and I’m the founder, photographer, and first impression architect of Top-Tier Headshots. I used to be a high school science teacher who had a passion for wildlife photography (still do). As I developed my skills with wildlife photography, I began to fall in love with the photography itself and wondered how I might make a career out of it. I had been doing the occasional people portraits on the side to make some extra cash (teachers aren’t known for having incredible salaries). In those sessions, I found myself increasingly fascinated by genuine human expression. I eventually met someone doing headshots full time who ended up becoming a mentor for me. Headshots became the perfect blending of photography and intense focus on human expression.
I built my business around corporate headshots for individuals and companies, but quickly began to expand into offering other types of branding portraits for those same clients. I’m currently working on developing a style of portraits for keynote speakers that I’m really proud of and solves a great problem for them (how to get great photos of them on stage).
I help my headshot clients with two primary problems: 1) how do I get great photos when I feel nervous in front of the camera? 2) how do I level up my online image when headshots are typically reminiscent of school picture day?
The Expression Coaching I do with my clients is a mixture of tips, tricks, and coaching with my own personality/humor that brings the best expressions out of people. And part of that process is building rapport and genuine connection with people that adds to them forgetting they’re in front of a camera and genuinely enjoying the experience.
The coaching that I do combined with the lighting styles I’ve learned from A-List photographers like Peter Hurley and Felix Kunze (with my own unique style thrown in) contribute to producing images that help my clients be ready for any opportunity. Whether it’s a podcast appearance, a speaking engagement, or a top-tier business magazine feature, my clients are primed for these business-accelerating opportunities.
I think there are two primary things I’m proudest of in my business. The first is the incredible network I’ve built. This is a network of meaningful relationships that go well beyond business referrals. We’re always strategizing how we can help each other level up our businesses, and the results are evident.
Another thing I’m proud of is how quickly we’ve grown over the past 4 years. We went from zero to six figures in year one (2021), and then blew it out of the water with multiple six figures every year after that. We’re about to head into year five and revenue is still on an upward trajectory.


We’d love to hear a story of resilience from your journey.
Entrepreneurs don’t win because they get lucky. They win because they don’t give up. I already mentioned my first month in business being a $60 month. That was extremely disheartening. There were also many other setbacks and challenges along the way. There were sales prospects that never made it to the finish line. There were people who criticized me for being too expensive. There were people who thought it was a mistake for me to specialize in just one area of photography.
One of the things I’ve learned as an entrepreneur is that everything worthwhile is on the other end of difficulty. Some people have looked at the business I’ve built in four years and call me an overnight success. What they don’t see is the sleepless nights, the tears, the knot in my stomach, the endless networking events, the sales calls that ended in “no”, and the empty calendar staring me in the face when I had kids to feed and rent to pay.
Entrepreneurship is a bit like Captain America getting punched in the face *again*, but getting back up and saying “I can do this all day.”
The people with a good idea, the wisdom/advice to know how to implement it, and the resilience to not give up when the going gets tough are the people who win.


Any thoughts, advice, or strategies you can share for fostering brand loyalty?
LinkedIn has become my online network. I’m connected with most of my clients on the platform, many of them finding me on the platform in the first place. Not only is it a great place to meet new prospects, it’s also a great place to add more value to your clients. Not only does my service provide my clients with an exceptional profile picture for the platform, but I can also use the image to give them a shoutout and encourage my followers to go follow them as well. I’m essentially providing my clients with free advertising. And who doesn’t want that?
Contact Info:
- Website: https://www.toptierheadshots.com
- Instagram: https://www.instagram.com/toptier_headshots/
- Linkedin: https://www.linkedin.com/in/toptierheadshots/
- Youtube: https://www.youtube.com/@toptierheadshots



