Interested in starting your own entrepreneurial journey in photography but unsure what to expect? Then read up on our interview with Kendra and Matthew Henseler, Owners of Summer Street Photography, located in Saint Paul, MN, USA.

What's your business, and who are your customers?

We are wedding and portrait photographers based in Minnesota. We started our business in 2010 on the East Coast and have had the privilege of working with hundreds of wedding couples in the US and abroad. We also photograph families in a relaxed, natural style that embraces the joy and unpredictability of children. Our clients are down to earth and share a fierce love for their families and spending time outdoors, eating good food, and being with friends.

Tell us about yourself

Photography found us in many ways. We are a husband and wife photo team, and our professional backgrounds were both in the performing arts. When we were dating and making plans for our life together, we were very clear on one thing - we wanted our professional life to be an extension of the values we shared in our personal life. We love history, traveling, cooking, baking, going to museums, hiking, and spending time with our family, friends, and pets. The beauty of life, as told through art, really speaks to us.

Photography is the perfect blend of these things, and the element of creating history is why we continue to be inspired as photographers. If someone can look at a photograph and remember how that moment felt, it's a little gift from the heart. The photograph is just a reminder of what's really important to a person, and if we can help remind people what's at the root of their love and joy - well, then we've done our job. That's a great feeling to put out into the world.

What's your biggest accomplishment as a business owner?

When we first started our business, we thought that reaching a certain financial goal or receiving awards for our work might give us the greatest sense of accomplishment. When those things came, they didn't quite hit that mark. We thought maybe it was expanding our business with multiple employees to serve more clients. Nice, but still didn't hit the mark. Then we thought traveling internationally to photograph weddings abroad might bring that sense of accomplishment. In some ways, it did, but still not it.

One day a client-turned-friend invited us over to their house for dinner. Their grandmother had just passed away just a few months after their wedding. On their walls were many framed photos from their wedding, including the one of the bride and her grandmother. That was the moment. Our biggest accomplishment is having our clients print and display their photos because it sparks joy and love in their hearts. After years of reflection on this trade, we stopped self-promoting awards or accolades we receive because they really don't matter. Instead, we try to give each and every client an amazing set of images that they will hang on their walls and remember what matters most to them. That's our motivation and biggest accomplishment.

What's one of the hardest things that comes with being a business owner?

The hardest things for us are that you're always on as a business owner and the amount of rejection involved with the field. It's a competitive field with lots of turnover and trends. It takes a certain amount of drive to stay in the industry for more than a few seasons. It's hard to see prospective clients share their plans with us and for us to get invested in their story, and they end up going in another direction with a less experienced photographer who may not care for them in the way we care for our clients. With weddings, most couples are planning for the first time, and it's easy to fall for sales tricks and photo style trends that won't age well on your walls.

It's also difficult to plan for things like medical or maternity leave, retirement savings, and illness. We've photographed weddings while ill, missed dear family events like our own friends' weddings or family reunions, and things like maternity leave don't exist. Owning a business is 90% the most incredible experience and 10% the most challenging experience. Friends or family who have never done it don't understand, which can feel lonely sometimes.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. When starting out, plan on two years of your business being a side hustle and plan on always working a year ahead financially. For us, year one was entirely built to cover the costs of our equipment, and we were still working other jobs. Year two was about building out a "1-year slush fund," so we were always operating with a year's worth of expenses ahead of us. Year 3 was when we went full-time and quit other work so we could live off of year 2's income and put that year 3 income in the bank for year 4. We've operated this way since we started, and it was the single best decision we made as we started the business. This allows for life to crop up in the weird ways it does (hello, global pandemic!) and provides some security in a field that is not always secure.
  2. Build a network of colleagues in your field, even if you work alone. Not only are the benefits of learning from others and gaining friendships a plus, but when you get into a pinch and get the flu right before a big deadline you can't miss, you can hire these friends to step in for you. Sure, there are losses, but you still remain dependable to your clients, which is a huge part of staying in the game. You're human and can't do it alone - build your village. Go to networking events, workshops, and coffee dates with people of similar styles and values as your business. Hire them to do work for you, trade services with other professionals you would hire anyway, and build your network. And if you're new to an area, check out the Social Media private groups of your niche.
  3. Know what you're good at - outsource the rest. If you reach a certain level of growth, you are going to need to be working nearly all hours of the week. This is not sustainable. When you know what success means for you, you can build your business around supporting that. For us, success means that our business is serving our life and not the other way around. We enjoy caring for our kids and spending time in the creative process with our clients. That means that the majority of our time is spent actually in sessions with clients and doing the creative edits ourselves. It also means that our children don't go to daycare but instead spend time with grandparents or at school. That's important to us. We can outsource other things like accounting, website maintenance, advertising, album design, etc. when we run out of capacity for the things that are not directly linked to our time priorities and values. Your business will only be stronger if you have a team of people doing what they do best, working toward the best version of your business.

Where can people find you and your business?

Website: https://www.summerstreetphotography.com/
Facebook: https://www.facebook.com/SummerStreetPhotography/
Instagram: https://www.instagram.com/summerstreetphotography/

Profile photo by Lauren Kirkbride.


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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