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.


  1. Mallie Hart says

    PBR is GOOD! Oh, but I'm wandering off topic! LOL.

    Derek, partner & husband, is the one who dabbles in any dev, but certainly not to the level you're discussing here. I've got one client who's a good prospect for a custom app. I'll go into any discussions about dev much better prepared after reading this. Thanks!

  2. says

    Thanks James for sharing your struggles. It is helpful to know that other tech start-ups go through the same difficulties. Funding and Development. Oy.

    The 3 options your friend shared: Fast, Cheap or Really good made me laugh. We used to say the same thing in advertising to clients, you can pick 2. No one ever liked those options, but it helped them learn to make tough decisions.

    On a side note, I'm with Mallie – PBR Tall Boy isn't the worst thing in the world. : )

    • James Oliver, Jr. says

      Haha. I had no idea the PBR reference would foster so much banter :p

      Thanks for the feedback. Really appreciate it.

  3. says

    Fast, cheap, or really good. Love that, in fact if you think about it, depending on the situation, PBR fits all 3 of those. Great post, and I can honestly say that every entrepreneur I have ever worked with seems to say the same thing. 2 weeks is 5 and new platforms every time you turn around. Nicely done James, thanks for sharing

    • James Oliver, Jr. says

      Oh, look, another PBR reference! I think I'll be sure to mention it in every post I write. Hahaha!

      Agreed. It takes forever to get these things done. I won't even tell you what the original timeline was on the SOW (statement of work); it'll make your head spin.

      My hope is, going forward, on the really important things, I will just pay someone here in the U.S. more money to get things done faster.

      Thanks for commenting.

  4. brian says

    Thx James. I learn a lot from your posts. Thx for keeping the content strong. Congrats on the most important 2 things in this post. You will love being a daddy

  5. says

    Twins! Dude! I hope you're not a big fan of sleep my friend. Then, again you're a start-up founder. Keep on keepin' on my friend and just remember to stay close to you mentors / advisors. I think it is a great project and I will do all I can to help promote it on my end.

  6. says

    Ooooh this resonates. We're 18 months into development of a marketing analytics product that was supposed to take half that time. Everything takes longer and costs more that you originally anticipate. But I agree: #nevergiveup , or Winston Churchill's version, "keep buggering on!". Good luck with the twins!

  7. Daniel Hebert says

    Great post James!

    Love the advice about "Fast, cheap, or really good". I think a lot of entrepreneurs don't realize this. And good luck with your campaign!

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