Livvy Cunningham – Outside of the Box Series

Livvy CunninghamLivvy Cunningham – Philadelphia, Pennsylvania

Today’s Outside of the Box Entrepreneur Series is truly excited to introduce you to Livvy Cunnginham. Livvy and I didn’t know each other going to an event in Las Vegas, Nevada last year – but of a coliseum of thousands, we found ourselves sitting side by side. As I got to know this woman – her energy and willingness to help people was very clear. She’s not only an amazing mother of four, she’s also the manager and wife of professional boxer Steve Cunningham – and STILL finds time to fall into her element of a successful entrepreneur.

Her creativity and drive to succeed is unmatched. She has taught me the value in investing in yourself, and more importantly believing all things are possible when you put in the work. I’ve been truly fortunate to be part of Livvy’s circle, and was even more excited to share some of her insight and value with you.

What sparked your drive to become an entrepreneur?


Honestly, I feel like it has always been in me. As a child, I would think of businesses to start, lemonade stands, drawing pictures and selling them, babysitting, etc… I was always attracted to making money but on my own terms.

As an adult, it was when I graduated college and got a real job, working 9-5, that I realized that my dream of being a powerful corporate business woman might not be all that it was cracked up to be. I was working long, hard hours, not making tons of money and missing my family… that’s when I started to seriously think about the fact that there has got to be a better way. I didn’t see that as my life for next 20-30 years. I felt like I was smart enough, certainly had the drive, and if other women could have success working for themselves, then why not me?

You’ve been selected as an “out of the box entrepreneur” would you agree with this statement?


I think so. I would say I am an “out of the box” person. I don’t worry myself with fitting in too much, I know what makes me happy and so I go for that.

In terms of business, I think this is a very important piece of the puzzle in terms of having success. Life is not black and white and neither is business. So being able to adapt or come up with different ideas is really crucial in the marketplace.  

If you could have given yourself a piece of knowledge or advice when you started what would that be?


I would let myself know that the road is not always smooth with perfect visibility, it can get down right bumpy with thick fog, snow, sleet, etc. And also that being an entrepreneur is not glamorous. You read the success stories of people that went from rags to riches following their dreams and it all sounds so perfect. But the truth is, it is hard, long nights and early mornings of straight grinding. But if you are a true entrepreneur, this part while stressful, also gets your blood pumping and keeps you going.

To what do you attribute your success? What would say are the five key elements for starting and running a successful business?

1) Grinding. Getting into a place of tunnel vision and grinding it out. When I come up with a new project, I pretty much block out the world to focus on getting it done. This is exhausting but important to hitting goals and getting ahead.

2) Never stop learning. I am always readying books, watching trainings, asking questions. There’s no such thing as knowing too much. I love mastering new topics. Personal development is so important.

3) Networking/Masterminding. I am so blessed to have super smart and talented friends. I am never scared to hit someone up and ask them a question inside of their expertise. And on the flip-side, I am always available to my friends and colleges in the same way.

4) Planning. While I would not say this is one of my strengths, it is very important to my success. I have a huge white board in my office where I write down notes, ideas and goals. I am a very visual person so I love using this tool. I also utilize daily planners and notebooks to try to keep myself on track.

5) Courage. Lastly, I am not scared to fail. I have done it before and every failure has always been an important lesson. It sounds cliche, but we will never know how big or successful something could be without giving it try. Not just a try actual, but giving it your all.   

Who has been your greatest inspiration and why?


One thing for sure is that I have been blessed to work with amazingly smart women in my career. It just kind of worked out that I have always had super smart, driven, successful women as bosses, and I have learned so much from them. And even though I have chose somewhat of a different course for my career, I will always carry those lessons with me.

Outside of that, I love Gary Vee, his no nonsense, get up and go get it message speaks to me so loud and clear. One of my favorite videos is his Monday Morning Motivational Rant, I love it!

In network marketing, I love Sarah Robbins, she’s a complete Rockstar.

I also really love the book The Greatest Salesman in the World by OG Mandino.

When the readers would like to get in touch with you, what is the best way for them to do so?


The best way for readers to connect with me is on Facebook and Instagram

And definitely check out my newly launched website


How real was that? I’m sure you gained as much value and even as much insight into the reality  of entrepreneurship through this small snippet of what was shared through this interview with today’s “outside of the box entrepreneur”. Comments and Feedback always welcome – either by signing in below, or emailing me at

The entrepreneurs who have participated throughout this series, have done so in donating their time. Always serving, endless value, leading from the front. 

When I began this series of interviews, reaching out to successful, full time, entrepreneurs, I had one purpose – for this information to touch someone, somewhere who might be thinking of giving up. Reaching someone who needed to know that entrepreneurship isn’t always rainbows and awesome sauce – but there’s a real hustle, a real grind. Know that if you put in the work, success is inevitable.

Thank you for reading xo

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