Jenna Kutcher: GLC Fall Featured Girl Boss

We were so excited to get the opportunity to interview, Jenna Kutcher of the Goal Digger Podcast! Her inspiring story and real life advice are takeaways ANY entrepreneur or blogger would benefit from.

When asked how she got started in the photography business, she said, “I don't think my story is different than most, I think all of our stories are different but parallel in a lot of ways! … I started with a $300 Craigslist camera that I bought while we were busy planning our own wedding and I wanted to document the process. I was working full time as an Executive for Target and rocking red and khaki every day in what I thought would be my dream job but soon after realized that there had to be something more out in the world for me. That was when I started to blog my photos (that were anything but good) and share my passion and it started to take off from there.”

Jenna Kutcher: Glass Ladder & Co Fall Featured Girl Boss | Jenna Kutcher | Glass Ladder Co


It's easy to feel like an outsider looking in as a new entrepreneur, you can’t help but wonder if these amazing and influential business owners always knew this was what they wanted to do. I asked Jenna if this was the case for her and she exclaimed, “No! I studied corporate business. I wanted to be the girl in the corner office with the windows and wear power suits and high heels. I used to joke that I wanted to come home and kick off my heels and have a husband who had dinner ready and the kids bathed. My life looks almost exactly opposite to those dreams and goals. I work in yoga pants, my husband works from home, we don't have kids yet but we are so dang happy to do what we love every day.”

It sounds like a dream I know… her reality seems to be so many of our wildest dreams but it’s important to remember how much hard work and time it took her to build her empire. It’s common to prolong your start to your entrepreneurial journey for so many reasons. Lack of motivation, self doubt, or even self consciousness that some people won’t approve. As a millennial it can be difficult to convince your parents that you can make it as an entrepreneur. Although they only seem to have your best interest in mind, many parents don’t quite understand how or why someone would want to pursue this. Luckily, Jenna’s parents were very supportive of her. “They were {supportive} but they were also very cautious (with good reason!) Here I was, 23 and leaving a corporate salary and benefits to do something I had ZERO education in. They knew I could do it but they really challenged me to set myself up for success. I think as parents, it's their job to ask the hard questions and that only made me fight harder for my goals which was a good test to make sure I was ready to fight for what I was dreaming of...


"Since then, my parents don't bat an eyelash when I tell them something crazy we are up to... it's safe to say that I've proven that my craziest ideas are usually the best ones.”

Jenna Kutcher: Glass Ladder & Co Fall Featured Girl Boss | Jenna Kutcher | Glass Ladder Co


If you’re just beginning your entrepreneurial journey, or even considering it, Jenna would like to tell you to “set yourself up for success. Take time, study your craft, find out what makes you different, create systems while your slow because someday you'll be too busy to do it, and never ever hide behind what you do. You are so much more than what you do! The industry has changed a ton since when I started, there's so much more accessible education and information and beginners are exposed to a lot more than we were. I had to piecemeal a plan together and it was hard, a waste of time, and energy... now there are so many amazing educators sharing content!”


Indeed there are! There are so many educators out there, some offering better content than others. But before you spend hours, weeks, or months digging through courses and workbooks, you need to take a minute to be real with yourself. Is being an entrepreneur really what’s right for you?


Lori Grenier said it best that if you'd rather work 80 hours for yourself than 40 hours for someone else - that's usually a good sign. You have to be ready to take responsibility for both your successes AND your failures. It's been a lot of years of a lot of hard work, there is no such thing as overnight success or a well-paved path, you've got to forge your own way.”


Jenna Kutcher: Glass Ladder & Co Fall Featured Girl Boss | Jenna Kutcher | Glass Ladder Co


One of the best ways to build your own path is to be authentically you in your brand. Vera Wang once said that the best advice she received was from her father...


He said, ‘sell yourself first, then your brand, and your product last.’


Jenna chimed in, “People want to buy from other people - not brands or businesses. They want to know, like, and trust you and if you're simply a logo posting content, they will never know who's voice they are listening to or who's words they are reading. When people start to know you and trust you, they will be far more likely to purchase from you. I also believe that social media is so much more than marketing. It's our modern day scrapbooks and diaries that share our happiest, best moments and I want to show up in my own story. I'm worthy of that!”


With that being said it’s important that you remain authentic. People want to see and hear from you, the real you. “BE YOURSELF. Your uniqueness is your only unique selling proposition so stop trying to hide the things that make you different or "other," those will be the things that make you memorable and make people WANT to work with you. You're going to feel like a fake or a fraud, that's normal, we all do, embrace it and get out there and put your best work out into the world.”


Jenna Kutcher: Glass Ladder & Co Fall Featured Girl Boss | Jenna Kutcher | Glass Ladder Co

One of the best ways to enhance your business and your quality of work is to have trusted individuals who can offer genuine and insightful feedback. Don’t take advice from someone who hasn’t been where you’re standing. Everyone has their 2 cents to put in, but the cents that are actually valuable are from those who genuinely understand your perspective. You wouldn’t take business advice from your someone who’s never owned a business, essentially. Jenna thinks the best way to achieve this is through a mastermind group! Which is “a small group of people who work together towards bigger goals, bigger impact, and bigger businesses. It's like group coaching but elevated because you're with other people who "get" you. I joined one this year and it's been a year long transformation of my business using tools like: accountability, goal setting strategies, and just elevated business practices. I get to share ideas with 20 other entrepreneurs and we all get to grow together. It's pretty incredible when you put such smart people in one room and troubleshoot any hard spots in your business and it's even better when you have people to celebrate with you when things are rocking!”


If you haven’t heard of Jenna Kutcher you should check out her podcast The Goal Digger! There’s a ton of valuable information and some great interviews. Who would you like to see as our next Featured Boss Babe? Let us know your nominations or requests below!