How Jenna Ahern Built Her 7-Figure Company

How Jenna Ahern Built Her 7-Figure Company

We’ve all heard the advice to jump before we’re ready. What’s happening before that jump though? Often, unintentional or intentional preparation of mindset and skills. Here’s how Jenna’s intentional preparation of both helped her build a 7-figure digital marketing boutique.

How Jenna Ahern Built Her 7-Figure Company

Meet Jenna Ahern, Co-Founder, and President of Guardian Owl Digital Boutique

Jenna Ahern, co-founder, and president of Guardian Owl Digital Boutique, a 7-figure business with 9 full-time employees shares with us how she started her digital empire in Louisville, Kentucky.

Kay Makishi: Some entrepreneurs say they wished they would’ve jumped sooner and encourage others to jump before they’re ready. Do you agree?  

Jenna Ahern: I come from a single-mother household and had no security blanket. I’ve seen and heard of people making quick decisions but that’s not me. I was working two full-time jobs for over 2 years before taking my leap of faith in starting my own business.

KM: Could you tell us about those jobs?

JA: I worked as an advertising consultant in the automotive industry. Back when I started, digital advertising was sort of like the wild wild west with absolutely no transparency. Clients couldn’t tell if their $10,000 investments converted into sales or not.

I saw an opportunity to do things differently. So I started consulting personal clients outside the auto industry on the side in the mornings before going to work, in the evenings, and on weekends. Working 17-18 hours a day, I learned I was a really really hard worker.

KM: Could you walk us through how you prepared to jump into your own business full-time? 

Jenna: At my previous employer, I gained experience under 3 Google premier partners and learned a lot from those opportunities. My personal opinion is that you should soak every single resource you can during your day job and make every connection you can.

“Build your empire in the dark.”

I started Guardian Owl Digital Boutique in 2013 as an LLC while I was still working my full-time day job. When I decided to make the leap, I put my 2 weeks notice in with my employer and on week 3, I hosted a digital marketing event as a Google Ambassador where 80 people showed up.

Because I was working on Guardian Owl full-time before leaving my previous employer, I was able to hit the ground running with clients and sales. We transitioned into an S-Corp in 2016 and are about to make our 10th full-time hire.

KM: What was your thought process like when deciding to leave your employer and work full-time on your business?

JA: I wrote the pros and cons out like a typical type A decision maker. At the time, I was working at a $15 billion company earning 6-figures at age 25. It was humbling. I thought who am I to think I can go out and do it better? Plus I thought about the healthcare benefits and my 401K.

Outside my full-time day job, I was consulting business owners to invest and build equity in themselves. Yet I wasn’t taking equity for myself. I was building it for someone else’s company. The biggest thing I was teaching came full circle back to me.

Since leaving my employer, our business doubled. And even if it didn’t, I’d still do it 10 times over again. Leaving my previous employer to work on my own business was the best decision of my life.

KM: What’s your advice to someone wanting to quit their full-time day job to work on their own business full-time?

JA: If you’re sitting there saying I’m not succeeding because I don’t have the time, I would ask if you’re doing everything you possibly can outside your full-time day job. If you’re saying ‘no’, I don’t think that answer is sustainable in business. Working two full-time jobs for me was a stepping stone as a business owner.

“Audit your time management.”

If you’re using every ounce of it, then maybe you are ready to make that jump.

Every entrepreneur’s story is different. How are you preparing for your jump? 


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