My Biggest Start-Up Challenge? Software Development.

I blog for three reasons. (1) It’s fun working on a start-up, but it’s also extremely challenging and frustrating at times. So, blogging is a catharsis. (2) I blog to share the kewl things I learn and the bone-head maneuvers I make, so that others might benefit. And (3) I blog to connect with entrepreneurial-minded people.

Last night, while having dinner with friends in Chicago, someone asked me, “what was the most challenging aspect of working on my start-up, WeMontage?” Without hesitation, I replied, “getting the software developed to bring my vision to life.”

Startup ChallengeI recently discussed the challenge of finding a founding partner with a tech background – someone who complements my skill set.  While navigating said challenge, I discovered three key things about the software development process and, most importantly, about myself.

I Can Have It All. Just Not Right Now!

A good friend of mine, Neil, a software engineer who wrote the iPad and iPhone app for Pandora, shared a lil’ wisdom with me about writing software. He said, “you can build it fast, cheap, or really good. Pick any two.”

Ugh! Seriously? Now u tell me. :-)  Can you guess which two it’s gonna be for this guy? Here’s a hint. I’ve got champagne taste on a PBR-er-Pabst Blue Ribbon-budget. Nothing against PBR, but it ain’t the lovely bubbly!

So, it’s the cheap and really good options for me. Thus, my awesome web design and development firm is in NY, but they are project managing software engineers in the Ukraine. Ukraine?! Yep, the Ukraine. And that’s why WeMontage has been in development since January. Yes. Since January.

Enjoy The Journey. Don’t Focus On The Destination.

Two of my heroes, Dr. Wayne Dyer and Deepak Chopra, preach the mantra of staying in the present, and enjoying the process without attachment to the results; this is incredibly hard for me. I truly aspire to be more virtuous, but I often fall short of the mark.

So many of my friends are über supportive of WeMontage and think the project is super-kewl and I’m doing a great job. But I’m always surprised to hear this because sometimes, I’m just in the weeds trying to get things done.

From finding the right founding partner; to early on, trying to understand why I should build the software in HTML5 vs. the soon-to-be-dead, yet ubiquitous, Adobe Flash; to understanding if the developers say it’s gonna take two weeks, it’s really gonna take 5-6 weeks; It’s hard to enjoy the journey and not focus on the results and road toward the destination.

will do better.


Despite my the challenges I’ve faced, the concept of WeMontage was pure inspiration, and I’m trusting the Universe to support it, and to do so abundantly. So strong is my faith, I’m launching a crowd funding campaign on, which competes with, to give WeMontage a jolt.

Below is a brief demo of the web application that is part of the IndieGoGo campaign. I’m incredibly pumped about the simple, clean, and elegant website and web application we’ve built!

If you’re interested, you can check out the WeMontage IndieGogo crowd funding campaign by clicking here. If you like it, please share it across your social media platforms.

My amazing wife is pregnant with twins and I’ll be a first-time dad in March. When my kids are older, I will teach them many things. But one of the most important things I’ll teach them is Never Give Up. Ever. 

Have you had challenges starting a new biz? Please leave a comment and tell me about them and what you did to overcome them. What did you learn about yourself? 

James Oliver, Jr.
Co-founder of the world's cutest twins. Founder of Parent entrepreneur advocate via Alum of the startup accelerator and UNC-Chapel Hill (MBA). Cheeky. ESTP. Golf nut.
James Oliver, Jr.

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