An Accidental Entrepreneur: How I Started Four Businesses and What I’ve Learned Along the Way


On my return flight home from Boston, I found myself crawling my way off the plane with a case of the flu. I had just returned home from a long week of traveling for work. And little did I know, my day was far from over. I walked through my front door to find my 16-month-old son on a breathing treatment with RSV.

I literally laid down on my living room floor and said “I’m done.”

It was at that very moment I made the decision to do something different. I knew I wanted more flexibility in my life to be there for my family and spend time with my growing children. And my current job just wasn’t cutting it. While I had those desires and dreams, I never set out to be an entrepreneur. Hence, why I often like to label myself as an “accidental entrepreneur.”

Since that living room floor moment I had in 2004, I’ve started four businesses in the last thirteen years in the apparel, software, and service-based industries. I’ve also successfully sold one business, while two others are still in operation today.

So, you might be wondering: how did I get started on my journey?

Well, simply put, I walked into my boss’s office with a proposal in hand. That proposal highlighted all the reasons why they should hire me on as a contractor to finish out the projects I was currently involved in.

Transitioning from full-time into an independent position would allow me more flexibility, while they would be able to fulfill their current obligations without training anyone new. (Plus, I actually ended up getting paid more! Go figure.) It really was a win-win situation.

From that point on, as I was working from home and being my own boss, my entrepreneurial spirit was growing by the day. Suddenly, I was 100% in charge of my own schedule and the amount of money I was bringing in.

Was it scary? YES! But, was it worth it? Absolutely!

Over the years, I built a successful software consulting business working with government contracts and healthcare clients. Being an entrepreneur is all about taking risks. And that can be downright terrifying.

But, because I made the leap and started my own business, I was able to fund my other endeavors. I could finally spend more quality time with my kids (I have four of them, so believe me when I say I know the chaos with kiddos). Not to mention, I could succeed without having to depend on my location. Like all good stories, however, there’s a twist…

I became an active duty military spouse.

My husband, who was a reservist at the time, came home one day to tell me he wanted to go active duty. Of course, I was 100% supportive because, being a business owner of a virtual business meant I can pick it up and go wherever, whenever. So, what did we do? We started our military family journey.

When we moved into our first predominately military community, I was amazed to find out that many of the talented and highly-educated spouses around me were struggling with unemployment.

This space was new to me and I had no idea this problem existed. Seeing spouses unable to continue their careers lit a fire in me. And, that inspired me to begin hosting coffee dates and sharing how I translated my skills into a new business of my own.

After that, we moved four times in five years of active duty service. Talk about baptism by fire!

During one of our short PCS moves, I met my co-founder, Erica McMannes, at Fort Lee, Virginia. We kicked off our relationship in an online fitness group. Through it, we shared our stories of business ownership and professional experiences as military spouses. But, like all military spouse friendships, ours was cut short by another PCS.

Two years later, I got a message from Erica out of the blue with an idea to create virtual job opportunities for the military spouse community. She knew I had the business and tech background to help make this happen, and I was instantly onboard. Thus, MadSkills was born and we officially launched it in 2016.

Since then, we’ve worked with more than 25 employers, placed 60 military spouses in virtual jobs, and we have an internal team of seven military spouses helping us achieve our mission. Now, we’re coming out of the startup phase of business and growing in year two with more than 2,200 military spouses in our talent community.

From the very beginning of my entrepreneurial journey, I’ve learned a lot about myself. It’s not always easy, but it’s a great path for military spouses looking for seamless portability. You just have to pick the right business!

That said, I’d like to leave you with some of my key takeaways after being a business owner for 13 years now:

Activate your grityou need a whole lot of grit to make it on the entrepreneurial path. It’s okay, though. If you’re a military spouse, grit is practically your middle name.

Don’t be afraid of partnering with someonemy cofounder is my battle buddy. She compliments my skills, challenges me to be better, and is always in my corner as we work to achieve the great things in store for MadSkills. Having someone working towards the same dream as a team is priceless. Just make sure you pick a good one, like mine!

Know when to delegateyou’re not going to be good at everything. Please take time to recognize when outsourcing or bringing on another team member might help you move things along faster and more efficiently.

Find a mentora mentor helps get you where you want to go at a much quicker pace. You want someone who is honest and successful so you get the feedback you need to grow your business. A good mentor is worth their weight in gold.

Good luck on your journey. Let your passion drive your purpose and keep reaching towards your goals!

Have you ever started a business? What tips would you give someone who’s considering it?

Posted by Liza Rodewald, military spouse and cofounder of MadSkills

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