MEET JESSIE WYMAN PHOTOGRAPHY
FOUNDED BY
JESSIE WYMAN
LOCATION: BOSTON, MA
@jessiewymanphotos
THE INTERVIEW
Written by Boston Women’s Market
BWM: First the fun stuff; what is your go-to weekend spot in Boston?
Jessie: I head to Barracuda Tavern because it's tucked in an alleyway by the Beantown Pub so we never have to wait for a spot to open up. And even though it’s bar food, I love the atmosphere. It takes me back to my college days. Fun tip, I went to college at Iowa State University, home of the Cyclones. The Barracuda Tavern is actually a meet up bar for my rival, the University of Iowa, home of the Hawkeyes. Even though seeing the Hawkeye memorabilia makes me cringe, it does remind me of some of the best times back in the midwest.
BWM: What is your go-to Podcast or book of the moment?
Jessie: Well, my own podcast of course! I co-host the Cocktails & Content Creation Podcast with my business bestie, Kate Andrews. We interview content creators on easy ways to create great content and put it out into the universe. After that, I’d say I really enjoy Behind the Design Podcast because the episodes are easy to digest. I also like the Bokeh Photography Podcast which is geared towards photographers.
BWM: Can you tell us a bit about what led you to the launch of your photography business? What was your aHa moment?
Jessie: In 2008 I was gifted a Nikon D60 with a kit lens, but I didn’t really pick it up until 2011. Then after two years of learning how to use it and figuring out my style, I started shooting portraits and weddings in 2013 as a side hustle to my 9 to 5. I left my job in 2015 to get my master’s in Urban Design. But instead of going back to full-time work, I decided to pursue photography and freelance as an Urban Designer - which I still do occasionally.
Though I loved taking photos, I wasn’t sure that wedding and family photography was the right fit for me. My breaking point came after waking up the Monday morning following an epic weekend wedding shoot capped by a two-hour family session. I was convinced I’d been run over by a truck.
But I wasn’t just tired because of my busy weekend, I was tired of missing every weekend. I was tired of worrying about making enough money each wedding season to sustain my income needs year-round. I was tired of doing work that drained me.
From the moment I tried brand photography in 2018, I was hooked. Not only did I love collaborating with entrepreneurs, but I was also able to do it during the week and have my weekends to myself.
And with a lot of work and a few stumbles along the way, I finally feel like I’ve found my niche and my happy place with brand photography.
BWM: Our Members are often just beginning to grow their business and are interested in learning from other successful founders. Can you share a few key pieces of insight or learnings you have acquired from concept to launch?
Jessie: To anyone just starting out I would say make sure you take into account all of the expenses, down to the little things, that it takes to run a business.
Outsourcing my blog writing and other regular tasks have been a huge timesaver - I wish I did it sooner!
You need to figure out who your ideal client is so that you can tailor your marketing to that person. And knowing how your product or service is going to change their lives and explain that to them - that can really help your business take off. Also, beta testing is huge! Before you go crazy on an idea, test it. See if it works, see if it’s what your audience needs. Then go build it out from there.
BWM: The pandemic has affected us all in very unique ways. How has the pandemic impacted your business? What are the positives you've been able to take-away?
Jessie: The pandemic brought my business to a halt. From March through June of 2020 I was unable to shoot. But I realized It's more important to support others as best we can. I ended up doing a week of freebies, including my Lightroom Mobile Preset, in hopes that I could still help other entrepreneurs even though I was unable to actually work. Now I’ve adopted the new normal. I shoot with safety protocols in mind and realize how important open communication is with my clients.
BWM: How did you have to pivot your planned business strategy to thrive in 2020?
Jessie: I turned my focus to creating great content. I hired a blog writer and started posting twice a month to my website. But I don’t just throw up photos of my latest shoots, I try to provide value and inform people about the importance of branding photography, how it can help a business, as well as other business tips. I honed in on providing valuable Instagram posts that weren’t just aesthetically pleasing, but informative as well. I also established a consistent newsletter so, between all of these ways of communication, I’m reaching out to people and establishing myself as an expert in my field. Plus I also have an online course, The Brand Photographer Method, where I teach other photographers branding photography. I really worked to scale that during the pandemic.
BWM: We think the stories of failure are just as important as the stories of success. Can you talk about a time that you failed in an entrepreneurial venture or objective? How did you face and overcome this failure? What was the lesson learned?
Jessie: When I decided to give branding photography a go, I knew I had to build my portfolio. So I held a mini-session event which was a total bust. I didn't even make enough to cover the cost of the rental space! But I did get the photos I needed and it made me think about how to better plan mini sessions in the future.
BWM: How have you continued to manage the growth of your business while also finding time and ways to invest in yourself?
Jessie: I use the Starfish Retrospective Method to organize what I want to keep doing, do more of, do less of, start doing and stop doing in my business. I learned about it during a Mastermind I participated in. Look it up - it’s life-changing!
As for finding time, I decided to set some boundaries for my business this year and so far, so good! The first boundary is that I only take and return any kind of client communication between 10 AM and 4 PM. And if I do receive anything outside of those hours, like an email or DM, I don’t open it or listen to it until I’m into my next workday. The second boundary is that I have “shoot days.” Instead of shooting every day of the week, designating that time also provides me with “office time” to edit photos, answer emails and voicemails, and plan shoots.
I actually budget for education, equipment and other opportunities each year so it's built into my cost of doing business!
BWM: Do you have a favorite go-to business tool or resource you can recommend to our community?
Jessie: I am a junkie for resources and tools so I actually have a few favorites. One would be Slack which I use to communicate with my team. Google Drive is the easiest way to coordinate content creation. And finally, Asana helps me to delegate tasks so everyone stays on track. I couldn’t live without these three!
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