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Entrepreneurship

Founder’s Therapy with James Oliver of WeMontage

James Oliver is the founder and CEO of WeMontage, the world’s only website that lets you bring your photos into a custom collage on removable wallpaper. He shares his incredible personal story and lessons from previous entrepreneurial launches, the importance of family support, and addresses ongoing thoughts and positions on mental health in the black community.


I have known since I was in High School that I wanted to have my own business one day. I went to Morehouse as an accounting major, was number one in my class, and graduated with honors, but in my senior year I specifically I told my mom I did not want to be an accountant. I wanted an accounting degree as a background for business. She didn’t want me to change my mind because she thought it was a good, safe choice where you could always find a job.

My mom is one of my biggest supporters and cheerleaders and always told me that I could be whatever I wanted to be in life, which is ironic given that she didn’t want me to leave accounting. It motivated me to start a tech company even though I don’t know how to write code and the software is all custom software. After business school—I graduated from UNC Chapel Hill in 2002—I did my summer internship at JP Morgan in a private bank, and finished up my MBA in Barcelona. After school I was in Barcelona trying to network and find a job in a very poor job market. It is funny how the universe throws you curves sometimes to get you on track.

I decided to start a lifestyle magazine called Seven Under for black golf enthusiasts but the business plan and the business model was unsuccessful in raising capital. It didn’t work out, but it was my first attempt at entrepreneurship. While the magazine never launched, I did a prototype issue of the magazine and interviewed Jason Kidd. That was validating, here is the guy who was on the cover of every sports magazine working with me. He saw himself in a completely different context and liked it. I still have those magazines in the basement, maybe one day they will be worth something with his autograph.

I got engaged during the process of all that. My wife even back then was really supportive. I think the most important thing for an entrepreneur if you are in a marriage or a serious relationship is a supportive spouse. Obviously, you need to have a reasonable value proposition a good business a good product or service that people are going to pay you for so you can grow your business. Next to that the most important thing is a supportive spouse. Otherwise, the business is going to end badly or the relationship is going to end badly or both.

After getting married I got a job working for Absolut in Chicago and made a decision to be an entrepreneur after being laid off. I actually interviewed for a job at my wife’s company but turned down the final round of interviews because I was choosing a different path. I started a business plan in consulting business, which I knew was not a long term not really sustainable. It was a conscious choice, I was an entrepreneur and I was going to figure it out.

I could not have made that choice without my wife. With that choice things got more challenging than you even imagine. But it is in those challenges, in the fire is where the metal is forged, it is through the challenges where the character is built and where you really learn what you are made of and what is possible and you learn to not be afraid.

I was inspired to launch WeMontage after my wife was watching an interior design show on HGTV and they were in a family’s basement covering an entire wall with these beautiful collages. I thought it was the coolest thing I had ever seen. I had these amazing pictures from my wedding in the DR and I wanted it in my house too. I literally stayed up all night long trying to figure out how they did it, that is when I decided to head down to path of WeMontage.

We were trying to get pregnant and were having some challenges so we did IVF and got pregnant with twins. So my mind is on the entrepreneurial thing and my wife is pregnant. I was still grinding on my little consulting gig which is getting nowhere and I put the last $35,000 I had in savings into building an alpha version of the site. Because I have champagne taste on a PBR budget I wanted it really good and really inexpensive so this website that I was promised was only going to take three months took a year.

I was not financially prepared for that so we get to the end of the year and my consultant business was not doing so well. WeMontage was taking forever to get built and I was really out of cash, broke and hustling, working at the mall during the holiday just to make a couple dollars.

In a lucky turn of events, I was invited to go to an open pitch event at this entrepreneurial symposium after someone mistook me for another James Oliver, which thought was hilarious. At the event Generator was looking for entrepreneurs to apply to their accelerator—a twelve month boot camp where you get mentorship, help validating your business model, support with customer acquisition, and develop a strong position to raise capital and launch your business. I knew it would give me the credibility I needed to get investors, which I had been unable to get on my own. Out of hundreds of applicants, I was one of five that got selected to be in the winter 2013 cohort.

Things were great up until the day they weren’t. At a routine check up we learned our son was not getting proper nourishment and had to have an emergency C-section. The babies were three months premature, and weighed 2lbs. a piece. The delivery was just so traumatic. My son could fit in my hand, literally.

The accelerator program was starting the next day or so two hours away by car in Madison, Wisconsin. If I don’t go most likely WeMontage is dead, but I can’t leave my kids in the hospital fighting for their lives, my wife just recovering from a C-section. I told my wife I wasn’t going, but then my she looks at me and says I have to go because the family needs WeMontage to be a success.

I cried every day for two months due to the condition with the kids. I was under a tremendous amount of stress and pressure to get my MVP built for demo day. I was paired with a janky developer who was so unreliable, my skin was breaking out, and I woke up every morning at like 2 o’clock and could not get back to sleep. But somehow I persevered and I got through it and I raised $300,000.

I launched and spent six months trying to configure and add critical functionality to it before running out of cash spring of 2014. My investor told me peace out. I remember one investor told me he didn’t want to throw good money out the bag. The personal business account went negative $1000, which is the point at which the bank stops clearing the transactions in case anybody was wondering. I was literally staring into the abyss.

Despite this I continued to hustle and in April 2014 WeMontage was featured on the Today Show, out of pure luck and hustle. NPR was doing a series called a A Day In The Life: Blacks At The Cutting Edge Of Innovation. I also managed to connect with Mario from the Today Show and WeMontage has been featured on the Today Show twice now.

I also secured a feature on the DIY network and we did about $30,000 in Q4 sales because of those placements. As I had a clear path for what I need to do to get things going in the right direction, the same dude who gave me money off the bat invested another $100,000 with his angel group.

At this point I needed to refocus and remember the “why”? People display pictures because they have or feel a loving connection to the people or the places in them and it inspires them. Our product is customized, has a unique large format and doesn’t use nails in the wall. Our users tell us they love WeMontage because they get more love, more happiness, and more inspiration from the product.

I knew that homesickness in college freshman who go away to school was a problem. I believe 25% of freshmen who go away experience some degree of homesickness. 20% experience moderate degrees of anxiety and it gets so bad for some of them that they drop out of school all together.

I had this hypothesis that seeing images of friends and family and loved ones would help students staying connected to them through our unique format. I donated WeMontage because it was a way for me to connect with them. A bunch of college students ordered the product and their friends wanted it or they ordered again so it worked to an extent. It caught the attention of a large national newspaper that I have seen positively change the trajectory of startups. They are doing an article about homesickness and college freshman and will interview some of my customers.

I was trying to figure out how to turn the business around. I was staring into the business module and dealing with screaming 18 month olds all day long, every day. I felt anxiety and fear and the only thing that helped and still helps me manage is meditation.

People don’t really talk about mental health issues with entrepreneurs. Everybody loves to read about the company that just closed a $20 million dollar round. But what about the majority of people out here who are struggling and can’t get product market fit or get from point A to point B to grow their business?

Depression and anxiety are just fear. But you know the amazing thing is I am not afraid. I am just not afraid. I am not anxious because my back has been against the wall so many times and I know it is there where I’ve had the biggest breakthroughs.

From that standpoint people need to understand that you are stronger than you know. You can tolerate more than you think and will grow and learn, then you will transcend those fears.

I raised another round of capital as a work home dad. I’m currently writing an article on my blog with tips for home entrepreneurs to get stuff done. Part of the reason I do what I do is because I realize my purpose is to brand and be a successful entrepreneur and inspire other people to be that too if they want to. I want to create a place where people who are parent entrepreneurs can relate to the journey.

I eschew the platitudes and the click-bait. I care if people read it but that is not what has inspired me to write. I write because I intend to share my story with other entrepreneurs and parent entrepreneurs who may be wondering “Am I in this alone? Am I the only one going through this?” I share some of the mistakes I have made on my entrepreneurial and parenting journey. I want to be a shining example to my twins for what is possible when you choose to live an authentic life and not risk playing it safe.