How I Became an Accidental Stay at Home Dad-Er-Entrepreneur

Photo by bjornmeansbear
Photo by bjornmeansbear

Starting Up Then Running Out of Cash

It’s cliché to say being an entrepreneur is hard. Duh!

I was fortunate enough to launch my company, WeMontage, after completing a tech accelerator in Wisconsin called gener8tor. And I was even luckier to raise investment capital, which gave me twelve months to try to get to product/market fit before having to raise an additional round of capital. But as we all know, things don’t always go as planned.

One year after launching the business, we built a great product and had lots of super happy customers. I can’t even put into words the pride that I felt in this. It made it feel like all the hard work was worth it. I finally had a business that I created myself up and running and I couldn’t be prouder. To be honest, I really enjoyed myself. I loved getting stuck into every part of the business. Of course, there were some things that I enjoyed more than others, but anyone who has ever started their business will tell you the same thing.

One thing I particularly enjoyed was creating advertising campaigns for the business. Until I looked into this more in person, I didn’t realize how many different types of adverts there are. Online adverts, dynamic promotions ads, carousel ads. The list is endless. And while they all offer different things, they all have the same aim. To get your business recognized by the wider community. Well, it clearly worked because my business had many customers coming through its door each door.

Unfortunately, my joy and happiness didn’t last for as long as I would like. One day, everything just changed. For the worst. It is hard for me to say this but we ran out of cash and were unable to secure additional financing, which I wrote about extensively here. Like any entrepreneur in this situation, I cut expenses, both for the business and personally, while I continued to look for repeatable, scalable paths to market.

The Decision To Stay At Home

Photo via PageTX
Photo via PageTX

The decision to stay at home from a practical standpoint was an easy one. Our nanny was going back to school and the timing of this was really a blessing in disguise because, as I said, we needed to cut expenses at home. The thought was I could stay home with the twins, while working on WeMontage between their naps and in the evening. Makes perfect sense, right?

However, what makes logical sense doesn’t always work emotionally. My initial feelings were not supportive of the idea. I know this was ego talking, but it felt like I failed at the business. After all, when I started WeMontage, my goal was to build it and sell it for tens of millions of dollars in five years. I was also doubting my ability to work from home. I was concerned about all the potential distractions. I also panicked about my company looking unprofessional as the address for my business would be a home property and I was concerned it would be judged for that. Again, this was ego talking, but I was still worried. It was at this point which I discovered yourvirtualoffice, which gave me a registered office address to list with my business. It also meant I had somewhere for meetings, which was a bonus. I also decided that I would just have to manage the distractions at home, including the twins. Of course, there were other concerns too. One of them was my internet and phone provider. Working from home would mean that some of my bills would be higher, so it was important that I considered looking at other providers to keep the cost down. One of my friends actually told me that I could get a deal for my internet and phone by visiting She said that I would probably need a good internet connection and a phone system to interact with customers and clients, so I also had to think about things like that. I looked around all the providers in my area, and paid particular attention to how much I would be paying for the services (fortunately, things like Xfinity internet prices are very easy to find online) to make sure that I would be able to get the best connection possible for my money.

Then I realized the twins are only going to be this age once and it could be a really special bonding experience for me and the kiddos; so, I decided to focus on this, and not feeling like a failure.

Success Is Still Possible

The reality is WeMontage is still moving forward, albeit slowly as I work hard to rebuild momentum, and it still has the potential to be a huge success-just not in the time nor manner in which I initially envisioned.

There is also still a very slim chance I may get called to appear on Shark Tank (check the P.S. section of this post for a fun social media recap of my efforts to get on the show). Additionally, we are scheduled to appear on the DIY Networks show, I Want That, in November, and I just learned we will appear on a SUPER popular national morning show in October. So, the fourth quarter will be good. I just gotta keep grinding and hang on.


A good friend of mine once told me that most people who have set backs never push through and persevere; they let the obstacles define them. I chose not to be defined by failure and certainly choose to persevere.

Have you ever had to reverse course on your entrepreneurial dreams and make a choice to be a stay-at-home parent while chasing your dream? I’d really love to hear about it in the comments section.



‘trepLife Dad

P.S., Here’s a link to that fun Shark Tank social media recap I promised ya –>


    1. Thanks, Ashley, for stopping by and commenting. Doing the best I can, you know? Please keep me posted on how things are going with you. And don’t hesitate to reach out, if I can ever help.

  1. You know I think you have a great product! It’s important not to let the obstacles define us…nothing that is worth having ever comes easy. That’s what I always tell myself. 🙂

    1. So true. Thanks so much for all the support these past few years, Michelle. I am blessed to have met you.

  2. Thanks for the link to your blog. It’s interesting reading about the people behind the company. I also love your description… “co-founder of the world’s cutest twins” that cracks me up. 🙂 So far I love WeMontage, and am looking forward to getting my print. Thanks again for everything! 🙂

    1. Thanks, Debi, for stopping by! I look forward to engaging with you. Let me know how you like your WeMontage!

  3. Being an entrepreneur is not for sissies and being a parent is for rugged maniacs! You are an inspiration to many James and your beautiful babies will grow up to tell the story of their incredible dad who didn’t quit, who sacrificed and went after his dreams with passion and HUSTLE! We are all cheering you on! From a fellow entrepreneur (20 years now) and mother of 4 (30 years now!)

  4. Hi, this is pretty cool. I just stumbled onto your site from twitter. I recently quit my job to become a part time stay at home dad, part time entrepreneur. The experience has been amazing so far.

    I had a chuckle when you said you planned on working during naps. I remember when I thought I could get things done digging the day. It didn’t take long before I realized it would have to be before she woke up or after bed time.

    1. Hey Isaac, glad you stumbled on me. I’m lucky that I have two and they play with each other. So, I can get work done sometimes when they are awake.

      Please stay in touch. Would love to learn more about your project, too.

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