JESSI CAPARELLA: LIKE A BOSS INTERVIEW

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I recently had the pleasure of interviewing my FAVORITE photographer to follow, Jessi Caparella. Jessi and I went to the same college (GO KNIGHTS!) and I have been following along (and completely admiring) her photography business and entrepreneurial journey since she started. She is a total BOSS. She’s booked out for wedding after wedding, featured in The Knot (I mean, whoa), and adored by everyone she works with.

Read along to see our q&a on business growth, her leap into photography, and her tips on consistency!


CASEY: Hi Jessi!! Before we start, tell us a little about yourself and your biz!

JESSI: Hi! I’m Jessi. 32, full time photographer, obsessive puppy mama to my yorkie Louis, social butterfly one minute, reclusive homebody the next, people pleaser to a fault, optimistic but realistic, lover of interiors and design, music connoisseur, vinyl collector, candle snob. 


CASEY: Yess, love it! When was the point when you thought ‘ok, I can take this photography thing from a hobby to a legit business’?

JESSI: I actually got my degree from UCF in Broadcasting. My dream was to be an MTV tv personality (back when MTV was still MUSIC television). When I moved to NYC after graduating to pursue tv production, my love of photography began. It was the one thing that made my soul feel alive and so every spare day I had I was wandering on adventures just to take pictures of anything and everything. Once I moved back to Florida the next year I went from pictures of street signs and architecture to pictures of humans and emotions. The joy it brought me was infectious and I think that was obvious every time I posted them on Facebook (yes, pre instagram). Friends were overflowing with support both emotionally and of course monetarily, booking me for sessions. It was when I started picking the brains of other photographers that I realized the potential of what this ‘hobby’ could become if I gave it my all, which of course would also mean making the jump into the lucrative wedding world. So I jumped! And here we are, 8 years and hundreds of weddings later!

CASEY: Every time you post wedding pics it makes me want to get married all over again! You have such a great eye for capturing all the beautiful details - when did you decide to pursue weddings specifically? [I know you also do lifestyle shoots but you seem to be constantly booked for weddings!]


JESSI: Since we’re talking business, the fact is - weddings are the bread and butter. I remember when I first started out thinking, ‘I’ll never do weddings, it's one of the most significant days in a couples life, I can’t handle that pressure!’ Well, I knew if I was ever going to take my business to the next level, this was where the growth potential was at both personally and professionally. I have come to appreciate the significance of wedding photography with such gratitude over the years, seeing pictures shared year after year on anniversaries, special holidays like Mother’s Day and Father’s Day or to pay tribute to the loss of loved ones. Timeless memories are the greatest gift to give these couples and their families.

CASEY: Where does the majority of your business come from? (Instagram, referrals, Pinterest, paid ads, etc)

JESSI: WORD OF MOUTH!!! The most beautiful and powerful tool. I was always very social growing up and made the most of being greek in college, so I started with a large network. With each wedding that network grew exponentially. I was always very conscious of the fact that each ‘job’ was simultaneously an interview for a future job (with the bridal party or guests in attendance.) I’m often surrounded by multiple of my former couples at weddings these days, I call them my tribe! It’s a huge part of my brand and the experience I put out to the world, that I want us all to feel connected together by something pretty special. 


CASEY: One thing I always tell my clients is that one of the biggest goals in branding (for all businesses) is for someone to see a photo, post, or graphic and KNOW that it’s from you before they even see your name. You have done an INCREDIBLE job of that. I could pick out a photo of yours in a crowd and be 100% sure that you took it. How has that evolved over time? How has staying true to that helped the growth of your business?

JESSI: Oh man, this is the single greatest compliment. CONSISTENCY. Thank you! It is something I hear pretty often and it keeps me going on days when I find myself comparing my work to others. Comparing is natural, but can really eat you up if you let it! In the first few years I would lean towards whatever was trendy in editing at the time, fluctuating from season to season. But then I would look at work only a few months old and not even like it anymore, so I made a decision one day to be confident enough with my style to stay constant. It’s been harder recently as darker and moodier trends have taken over, but I learn to admire it from afar but stay in my lane! So many of my inquiries start with “I love how your photos are so clean and bright!” and that’s a significant validation of staying true to myself and my vision.


CASEY: What’s been the HIGH POINT in your career so far?

JESSI: My TRIBE! They are truly my most valued treasures and the greatest reward for the grind.

Be a force of all the things that promote expansion! A force of ‘yes!’, a force of positivity, a force of perseverance, a force of social media, a force of support for others, a force of friendship, a force of passion!
— Jessi

CASEY: What are some of the things you struggled with when you were first starting out? How did you overcome those struggles?

JESSI: My business was fueled from an innate desire to over achieve. I was always an over achiever in life, I put so much pressure on myself for as long as I can remember. Had to be class president, had to get straight A’s, had to stay out of trouble… ya know, one of those goodie goodies. Most of those things always came pretty easy and quickly to me, so I struggled when starting this business was a hard and slow process. That’s something I need people to really understand and prepare for when becoming an entrepreneur. It doesn’t happen overnight, or even over a year or maybe even a decade. It’s a long hard grind, but it sure can be worth it.

CASEY: I’m a big believer that working on PERSONAL development (specifically as a woman) plays a major role in the success of a business, whether it be through self-care of the mind, body, or ideally, both. What are your thoughts on this? If you have any fav resources, books, etc. please share with us!

JESSI: You are right to believe it! I can say I have found refuge in home decor and skin care over the years but unfortunately, this is a more difficult question for me. I have definitely lacked in this department, always giving so much of myself to my business and to others over the years. I could argue my sacrifices have been for the better of my business and have led to its success but I can’t argue it has burned me out more times than I’d like to admit.. so I’m still trying to find that balance.

CASEY: Biggest piece of advice when it comes to EXPANDING your network?

JESSI: I truly believe you attract what you put out into the universe, so be a force of all the things that promote expansion! A force of ‘yes!’, a force of positivity, a force of perseverance, a force of social media, a force of support for others, a force of friendship, a force of passion! Your vibe attracts your tribe!

CASEY: Yes, yes, and YES. THANK YOU! Any other thoughts you’d like to share?

JESSI: It may sound trite, but I’d like to end with Ellen’s famous words... “be kind to one another”.

FOLLOW ALONG WITH JESSI AND HER BUSINESS, BREATHE J PHOTOGRAPHY:

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