5 Things You Didn’t Know About My Early Entrepreneur Days

Jenna Kutcher 

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April 24, 2019


5 things you didn't know about my entrepreneur days

I was thinking about it the other day and there’s a good chance that you don’t know much about how I really got my start or what those early days as an entrepreneur looked like for me… I mean, I talk a lot about my journey and share bits and pieces of how I got started but I’ve never really dove into what my reality looked like as I took a leap from my windowless corporate job into a world of entrepreneurship — and maybe, just maybe you’re sitting where I was those years ago, knowing that your soul crushing job couldn’t be all that this life had planned for you and wanting more but not even sure what “more” could look like or if you could make it happen. So let me pull back the curtain and welcome you into the life of 23 year old Jenna who believed there was more for her out there but could have never dreamed what was ahead… I’m holding nothing back, are you ready?

Before I Took the Leap

When I start to think back about those early days, I’m transported back to our first apartment, the one we moved into when we got married. I remember thinking it was the biggest, nicest little apartment and I didn’t mind the fact that we were in a random Wisconsin village of 1,200 people or that we were the youngest residents by a solid 20 years, we were finally able to live together and it was the BEST! What had landed us in that tiny, random village? Well, my corporate job with Target. We were living in Madison, Wisconsin when I found out that the store I was placed at was actually a solid 50-55 minute drive away which meant for realllllly long days that left me falling asleep during dinner and burnt out. We made the move to land us in the middle so that my commute could be cut in half and so there we were, newly married and living in a place where we didn’t know a soul.

It was around this time that I was starting to get serious about potentially starting my own business. I’m sure your eyes will roll if you’ve listened to this show for awhile but just in case, I HAVE to explain what landed me in a place of even contemplating starting a business. In 2011 we were planning our wedding, we were strapped for cash, broke out of college, I had student loans, and we were funding the majority of the wedding on our own.

To give you a little perspective, our entire wedding budget was about $12,000 to host over 200 people… So yeah, we had pizza at our wedding and served sheet cakes and my dress was a clearance rack dress that cost a whopping $358. It was also a season of life where I felt inspired by making our day unique without breaking the bank and I loved all things wedding, especially the photos. Now, this is pre-Pinterest era but I sat and perused wedding blogs, I even started my own wedding blog with a friend, called A Northwoods Wedding and we ran it for YEARS, it was actually the #1 Midwest wedding blog — but that isn’t the point, the point is that I was looking at wedding photos all day, every day and falling in love with wedding photography. I was on Facebook one day when an acquaintance posted a Craigslist listing for a camera that cost $300 and it had a fancy lens that I knew nothing about and so I jumped on it. Needless to say, I had no clue how to use it, I had never taken a photography or an art class, but I wanted a nice camera to help document things like my wedding shower, the planning process, all the things.

So now that you know I had zero experience as an entrepreneur, was in a season of life that included planning a wedding, having a wedding, working 50+ hours a week at my corporate job, and oh, did I mention we ran a full marathon in there, too? Let’s talk about some of the things that you might not have guessed about my early days as an entrepreneur.

I wanted to do things right — like I went to school for business, but it was corporate management and not entrepreneurship, but even though my education wasn’t fully aligned, I knew that I wanted to jump over some of the bigger hurdles right away. Now, let me just preface all of this with saying: I guessed as I went but I also made some really wise decisions, too. If any of you are an Enneagram lover, I’m a 3, the Achiever, and so I knew that if I was really going to do something and start a photography business, I wanted it to be successful. I’m afraid of failing, especially publicly failing and so that fear probably pushed me in a positive direction for a few things.

Getting Legal from the Start

I found a local accountant and set up an appointment to talk about all of the scary legal things and to figure out what it meant to set up a business, what it would mean for taxes, and how to be legal. Now, let me disclose the fact that I wasted a few hundred dollars on Legal Zoom choosing the wrong things that my accountants then had to undo but hey, you live and you learn, and I’m so thankful that I had the foresight to start there because those accountants? They still work with me today and they’ve watched my business grow and have walked me through every season and every phase. I am so, so thankful for them. So before you think an accountant will cost you a ton of money, chances are, they will save you money and make sure the IRS doesn’t come knocking on your door. If I could go back, I would probably look into something like The Contract Shop which my friend Christina started (and didn’t exist when I was launching) but having someone understand the industry and the legalities of it would be have been a great place to start!

Branding Beginnings

I knew the importance of branding. I remember back in college, the courses that fascinated me the most were the marketing courses were we got to dissect brands, look at things like logos and typefaces, figure out which products sold better because of what was on the packaging. I loved that kind of stuff, I still love that piece to this day. One of my college roommates had a boyfriend who’s sister was in design school and was willing to help create a logo for me and so I paid her $200 to help me create a “brand” which at the time I thought was just a logo and fonts and colors, but at least I started my business with a solid idea of branding and invested a little bit into the way things were going to look, beyond just the way things looked though, I also understood how that partnered with the way I wanted to make people FEEL. As a bride-to-be myself, I knew what I valued as a bride: it wasn’t just the picture perfect portraits, it was all of those tiny moments that I knew I would miss being in the center of the show and so I wanted my brand to communicate that I was basically the set of eyes on the day that would live long after the wedding ended. When I think of branding all those years ago, at the time I was focused on the way things looked but I also can now see that I used that image to help people FEEL something when they landed on my page.

Finding My Specialty

After a few months of photographing really random things from babies to boudoir, cats to political rallies, I quickly realized that I wanted to specialize in couples and weddings. I feel like this ended up being a super crucial decision because it not only set me apart from other photographers, but it showed people that I was focused on doing one thing really well and passionate about a facet of photography. It was also helpful that I, myself, had been a recent bride so I could talk wedding with my clients and share my own experiences in being a bride and planning a wedding day. I feel like a lot of times when we are passionate about something, especially a skill or a service, we’re willing to take any project or client that is willing to pay us and while I went through a few months with that mentality, I knew what I loved and what I dreaded and I also understood that my time was even more limited since this was just a side hustle and I still had my 50+hour a week job that kept me alternating nights and weekends, so if I was going to give up my time, I wanted it to be things I was excited about!

A Full Year of My Side Hustle

Did you guys know that I side-hustled this dream for over a year before I left my 9-5? Now, that’s not a long time and when I say the word “hustle” I mean it. But a lot of times we forget that a ton of successful businesses started as a side hustle and I think it’s a brilliant way to get things set up so that when you’re ready to take a leap of faith, you’re ready to rock! I made an early decision to never go into debt for my business — heck, I still had my student loans to worry about — and so I used my 9-5 to help fund and fuel my business. We budgeted and each month I had a hundred or so dollars that I could save and invest. Every penny I earned was being poured back into my business whether it was on new gear or things like a domain name, a WordPress site or business cards. Each month, little by little, I got things aligned and started gaining traction. I didn’t have a full line up of lenses, in fact, I didn’t even know what those little numbers on the lenses meant and was utterly clueless on how to do a thing like shoot in manual, BUT I did have a creative eye and a way of finding light and taking pretty pictures. I also spent a lot of time on youtube, perusing blogs, searching for answers to my questions on how to get better – you could say I subscribed to Google University to learn how to get better. I feel like people are embarrassed to share that what they are doing is a side hustle, but I’m proud of it! I was superwoman and I often look back at that season and wonder how I managed it all, how I balanced things. I think that my passion was so fierce that working late into the night didn’t bother me.

Goal Setting

From the very beginning I didn’t just set elusive goals, I set standards that would support the fact that I didn’t want to run a haphazard business or fall flat on my face after walking away from the security of things like a salary and benefits! I knew a few things about myself that might not look the same for you… Let me preface this by saying that I never quit. Like I hate the word quit. Every job I ever had I left because I was moving so it wasn’t like, “Peace out, I’m done, I’m going somewhere else,” and the thought of a 2 weeks notice scared me. I also grew up in a more traditional home where my parents worked their jobs for decades, understood seniority, worked their way up, and were so thankful for stability and benefits and 401Ks to if I was about to walk away from all of that, I better have a good plan. I knew that I personally wouldn’t feel comfortable leaving until I knew that I had some sort of plan that would at least set me up for success for the upcoming year and for me, that looked like matching my salary before giving notice. For me, it looked like spending an entire year working towards my goal of booking 25 weddings at about $2,500 to match my salary and give me a little cushion for expenses.

When Drew Lost His Job

There are still some things that you might not know about those early days… Did I tell you about the time, 10 days before our wedding, that Drew lost his job unexpectedly? Yeah, I probably left that part out. Talk about stressful. Here, our final bills we due and suddenly we were down to one salary, scary. After our wedding, it took Drew a good three months to find a new job and I supported that (with a side order of passive aggressive) because I didn’t want him to settle into a job he didn’t like and have us both be miserable. He sent out resume after resume, he went to job interviews, he worked a few odd jobs to help make some money and then he got into the wine world. As you can imagine, all of these life shifts led to a little anxiety: we’re newly married, my husband is unemployed, we have student loan payments due, we’re living on one salary, I hate my job, and I’m thinking about starting a business in a field I know virtually nothing about. It wasn’t exactly the perfect situation to up and leave the stability that my salary provided but it didn’t stifle me to stop preparing, I had faith that the time would come and that even though our circumstances weren’t perfect, now was as good of a time as any to get started.

I Had No Connections

Another thing you might not know is that I had ZERO connections. We literally didn’t know a single soul who lived in our town, I was over six hours from my hometown in Minnesota, our college friends had all dispersed, so it wasn’t like I had an eager audience of brides and grooms ready to trust me with their wedding day. I think a lot of times we assume that people are starting businesses that grow because of the support of connections whether it’s family or friends or a built in network but we had none of that. I had zero social media following, no online audience, and I didn’t have the chance to kind of start small and build up which was why it was so critical that I started off on the right foot building a brand, creating an online space, and then figuring out how to get my message out there. I think this forced me to get comfortable marketing myself early on because I knew that no one was going to market for me and I didn’t have an eager audience awaiting every move.

I Didn’t Know How to Use My Camera

I hate to admit this next point but if I’m keeping it real with you, I didn’t really know how to use my camera. I didn’t understand how to shoot in manual, I didn’t get what all the numbers meant when people talked about lenses, I had absolutely no clue how to use a flash, and so I was totally winging it and while I hate admitting that, I also think it helps you to see that it’s okay to start and to take imperfect action. Now, I’m not telling you to go out entirely undereducated and take a chance on hoping you can photograph someone’s most important day of their lives but I am telling you that it’s okay to begin before you have all the answers. If I had waited until I knew everything, I’d still be waiting. I remember when I was at one of my first weddings, I ended up sitting next to a guy who knew a lot about photography — now, mind you, the bride and groom chose me to photograph their day and not him, but he had a lot of questions for me. I remember him asking me which lens was on my camera and I had to look down at it and read off the numbers to him because I didn’t really know.

It’s wild now, how I don’t even think before shooting in manual, I can spit out every model number, every shutter speed, every aperture without a second thought. But it took time. Things take time and when I look back at what I did when I was starting, I still see beautiful images. Sure, the editing was a little weird, and some of the poses were a little funky, but I had the ability to connect with humans in a way that I wanted to be connected with and I used that to create beautiful photos that only got better with time. Sometimes passion can trump perfection and in my case, that’s exactly what happened. I didn’t have a photography degree, I didn’t have a full bag of gear, but I did know what kind of photos I wanted as a bride and I gave my couples those photos and so much more. People expect your skill but what they don’t expect is the experience that only you can offer them and dang, my experience was pretty good.

My Own Imposter Syndrome

One other thing I feel like I have to explain is the fact that I was struggling SO hard with feeling like an imposter…. Like actually. I couldn’t even say the words: I am a photographer. When people asked me what I did, I’d always hide behind the corporate job that made me feel powerful, worthy, impressive. Saying that I was trying to be a photographer meant that people could ask me questions I might not have answers to, it left me feeling vulnerable, cautious, and after coming across a few nasty feeds in Facebook groups about faux-tographers, it made me want to hide. It’s wild to think about how uncertain I was in that season because I knew exactly what I wanted but I was so worried about what people would think about that dream that I hid behind titles that the world knew, ones that didn’t invite more conversation or questioned my path. The world is comfortable with corporate things… executive terms… but I felt like it was against the dreamers, the doers, the people who were pursuing something more and I knew I was fragile enough to believe others opinions if I welcomed them into my life so I often just left out that little detail that I was attempting to escape the impressive corporate job that I, in fact, hated to do something different.

I think no matter what you do, when you step into a new role, there’s this feeling like someone is going to call your bluff or remind you that you really don’t know what you are doing. It’s this fear of being found out. But here’s the thing, while you’re so worried about what everyone else is thinking, they are probably not even thinking of you. It’s like we’re letting people’s potential thoughts that they probably aren’t even having hold us back and when you look at it that way, it’s the silliest reason to not pursue your biggest dreams. Right? So as you embark on this new adventure, don’t worry about what other people are thinking, worry about what you think about yourself and what your life should be filled with. You only have one life, make it count.

Looking Back

I’m reminded of all of the growing pains, the doubt, the fear, the small bank accounts, the bills, the questioning… But I am also reminded of the straight up passion, the passion that made me go to bed with a camera on my nightstand, the passion that left me eager to respond to every email, the passion at the thought that THIS could be my life, a life not filled with punching a timeclock or sitting in meetings, but a life that was fueled by what I loved. Not a day goes by that I don’t wake up with so much gratitude that I don’t have to report to a boss or an office, not a day goes by that I don’t have gratitude that I am in control of what’s next and how I show up and serve the world.

Not a day goes by that I don’t think of you, wherever you are in this journey and whisper a silent prayer that you will go for it, that you will pursue those passions, that you won’t ignore that greater call to live a bold life, one filled with excitement and enthusiasm, and serving the world in a way that only you can serve it! You don’t have to have all the answers, you don’t have to wait for perfection, today is the perfect day to start really going after those big dreams on your heart as an entrepreneur and I think it starts RIGHT now.

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  1. Branding and finding your speciality is one of the most important things for being an entrepreneur no doubt.


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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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