Jenna Kutcher

Jenna Kutcher: Yoga Pants, Mac ‘N Cheese & Minnesota Grit

14 mins read

Not so long ago, you would have found Jenna Kutcher in a stuffy, windowless corporate office, stuck in a ladder-climbing nightmare that originally presented itself as a “dream job.”

Today, this #girlboss is a self-made multimillionaire. 

How’d she do it? 

Patience, perseverance, and Minnesota grit.

Using her $300 Craigslist camera, Jenna pursued her love of photography… one image at a time. Had you suggested that this minimal investment would eventually lead to the creation of a formidable mini empire, she likely would have smiled with Midwestern politeness and quickly changed the subject.

Today, Jenna is a digital marketing and business expert who uses the expertise gained in building that empire to help other entrepreneurs grow profitable, passionate, authentic businesses that allow them to live more and work less— turning their passions into profits.

“In retrospect, I probably should have known that the girl who would haul a cooler half a mile to reach the intersection of two desolate dirt roads in a tiny Minnesota town to sell lukewarm lemonade for fifty cents a cup would eventually become an entrepreneur,” Jenna joked.

Her impressive success was undoubtedly hard-fought, yet achieved in what many would consider to be in expedited fashion. A key element of her success? Recognizing the need to hire a team when she knew she didn’t want to stay stuck in the “trading dollars for hours” business model. 

As her photography business flourished, she recognized that in order to scale and create more revenue streams, she’d need the support of others. She started with one hire, then the next and soon she was leading a team of ten. In recent years, it’s become blatantly obvious that her brilliance is as the visionary… not as manager or operator, though she’ll be the first to admit that she loves to integrate.

For a long time, it felt unnecessary to pass off the work she was very capable of handling to someone else. This is, perhaps, a large part of what her tribe finds so appealing—Midwestern sensibilities with, according to Jenna, “a brain that operates like it has a million open tabs.”

While each tiny decision made along the entrepreneurial path has contributed to her overall success, saying yes to each hire has played a significant part in her business growth. When referencing the business, Jenna often uses the term “we” vs. “me” because it truly is a collaborative effort.

Equally important? Launching The Goal Digger Podcast—Jenna’s liveworkshop style business podcast for creative “girl bosses.”

“When I started my podcast, it was literally an experiment,” Jenna said. “I was just going to do it for 30 days. We launched before podcasting became what it is now, so I really didn’t know what to expect.”

Recording her episodes using iPhone headphones from her car in the garage (so the audience wouldn’t hear her barking dogs), Jenna had no idea that her show would find its stride so quickly and help so many redefine success and chase bolder dreams. 

Her “experiment” turned into a movement, and with more than 33 million downloads (and counting), it continues to grow and gain traction every day as it provides listeners with productivity tips, social media strategies, business hacks, and inspirational stories to help them tackle goals and design their dream career.

Goal Digger Podcast with Jenna KutcherDespite her success—The Goal Digger Podcast consistently ranks as the #1 Marketing podcast on virtually every distribution platform—Jenna foregoes the fancy recording studio to this day, continuing to record in a closet in her home.

“I love to do the most with the least. My podcast has revolutionized our business in such incredible ways. It’s become the hub on our wheel of how we communicate to people, build trust, and get our offers into their hands. And I just love it! I’m so proud of our show. I feel honored to get paid to talk into a microphone,” Jenna shared.

Living proof that one can literally plug in headphones and hit record, Jenna hopes people can see that sharing your message is more important than using a specific technology or having a “perfect” set-up. 

“It’s about the message, and your message matters. Podcasting is a beautiful way to get your message out into the world and to continue to imperfectly lead, share, and craft a life you’re proud of… a story that is being written as you live it. It’s also a perfect way for people to integrate learning and community into their life,” Jenna said.

Community is vitally important to Jenna— and the timeless, instinctual human need to be part of a community has heightened relevance right now during quarantine, especially for location-independent entrepreneurs. 

“Often, we’re working behind a computer screen. We’re clocking long hours, dreaming up projects, or creating free resources. When we don’t connect with whom we’re serving, it all starts to just feel really heavy,” Jenna said.

Podcasting provides entrepreneurs with the opportunity to connect with those they’re most compelled to serve while garnering the requisite exposure needed to achieve the next level of success they’re striving to reach. 

That being said, Jenna cautions: “We often set our bar for success based on what we see other people doing. I’ve really had to learn to put the blinders on and keep my head down, to define success on my own terms.” 

Her definition of “success” may not be what you’d expect.

Yes, she is proud of the titles, her business, and her accomplishments. But what is she most proud of? 

“My freedom,” Jenna answered without hesitation. “While titles, accolades, and awards are beautiful, that’s not why I do what I do. I do it because I want to pursue freedom and encourage other people to do the same.”

Serving her community with this as her overriding mantra is part of what “puts fire” in Jenna’s soul… as does recognizing and applauding the countless number of people whose job it is to complete the necessary tasks essential to our society— trade-related tasks that others may define as lacking “passion.” 

Smiling, Jenna said, “The trades are super important! My dad worked in a paper mill or steel factory nearly his entire life. I think you can find fire in your soul no matter what career you pursue.”

And she should know, having held many jobs she considers “weird.” From limousine cleaner and working retail at Abercrombie & Fitch, to selling golf clubs in a pro shop (regardless of having never golfed a day in her life) and following in her father’s footsteps by driving a forklift for a paper mill, Jenna has what she calls “Minnesota grit.”

A self-proclaimed “really hard worker,” Jenna was able to find little sparks of fire in everything she did before ultimately discovering what really lit her up: her career, and being present for her family. 

Jenna’s journey to parenthood was not an easy one; in fact, it took three years to come to fruition. Now mom to a healthy, happy little girl Coco, Jenna has developed a fierce commitment to being present in every moment.

“If I’m reading my daughter a good night story, I want to be fully present,” Jenna shared. “If I’m working with my team or recording a podcast, I want to be fully present. That applies to everything in my life now.”

One of the greatest gifts that came out of Jenna’s journey to motherhood—in addition to her daughter, of course—is “being able to show women that they don’t have to choose between having a dream career and being a mom. You can do both, and you can do both well! It’s not going to be easy, and it’s not going to be glamorous, but it is absolutely possible.”

Of course, “having it all” requires balance… and Jenna rivals Simone Biles on the balance beam. 

She seeks out and accomplishes that balance by living her catch phrase, “Nothing is urgent,” and by operating from a place of “enough-ness.”

In a world where so many entrepreneurs draw arbitrary lines in the sand, reach their defined goal, cross out that line, and identify a new goal further down the path, Jenna does the complete opposite. Instead of continuously setting the bar higher and higher for herself, she perpetually contemplates how she answers the question, “What is enough?”

“I’m always redefining what is enough,” Jenna shared. “This applies to the number of hours worked, clients onboarded, the income we bring in, the team we hire, and how many products must be sold in order to live the kind of lifestyle we want to live.  

“When we operate by working backwards from that number, I found that I began claiming my time as my currency instead of my money… that’s when my business grew and scaled the most. Time IS our greatest resource. When you are clear on your priorities, everything takes on new meaning. Fact is, our lives are happening, and our families are waiting.”

Operating from this place of “enough-ness” also helps entrepreneurs avoid approaching their business from a place of urgency or scarcity, which rarely works out well. Neither does calling Jenna an “influencer.” 

Despite having a significant Instagram following, a top-rated podcast, and a flourishing business, Jenna admits she’s not a fan of the moniker.

“I hate the word ‘influencer,’” she admitted. “I am blessed to have influence, and I truly believe that if you have one follower, you ARE an influencer. I prefer the term ‘role model,’ because I get to paint possibilities for people.”

No matter how many followers she has or monthly downloads there are of her podcast, you won’t catch Jenna making her husband take 18 pictures with the perfect latte. Perhaps it’s her Midwest roots that keep her grounded. 

“I really don’t like people seeing me doing the Instagram-type things, though it’s a part of business today, and I’ll do some of it,” Jenna said. “It’s super uncomfortable for me to be ‘posing,’ and it feels narcissistic. I’d much rather be known for inspiring people to be the best version of themselves.”

There’s no doubt Jenna is able to accomplish this objective daily… both for her tribe and, most importantly, for her family. 

Enough-ness accomplished.

Steve Olsher

Steve Olsher is known as the world’s foremost reinvention expert. Famous for helping individuals and corporations become exceptionally clear on their WHAT – that is, the ONE thing they were created to do – his practical, no-holds-barred approach to life and business propels his clients towards achieving massive profitability while also cultivating a life of purpose, conviction, and contribution.

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