Edit 8/31/2017: This was a complete fail. I overlooked the complexity of adding new sites to our operations and even the straw that broke the camel's back was having to do a lot of work to get the payments to show that they were coming from a different entity than 80sTees.
Small companies are often characterized as being more nimble than larger companies. I think this is true mainly because a large company will have much larger consequences for launching half baked features. But for a smaller company half baked is often exactly when you should launch.
It is possible to run a small business with clunky systems and processes in the backend. If the website looks decent to a visitor they don't care how inefficient everything else is. In fact there are no points for doing things smoothly other than insuring a high percentage of your customers have a great post purchase experience. If you have to handwrite all of your labels and hand enter tracking numbers into Shopify the customer does not care.
I believe your marketing materials should look the way a duck looks to an observer. The duck swims along and it looks beautiful, effortless, and graceful. Under the surface the duck is kicking like mad. The duck is creating turbulence and lots of eddies and swirls under the water. A small particle in the ducks path would end up being buffeted about as if it were in a tornado. Your customer is the observer, your business needs to be the duck, and you and your employees are the buffeted particle.
Our company has experienced significant changes due to a strategic shift where I decided to drop ship as many products as we can while stocking as few products as we can. I made the decision to move forward with drop shipping before we actually were equipped to handle it with systems. We have an ugly process that requires man power. For me this was a big deal. I hate processes that rely on a person doing a task perfectly with any variance causing system failure.
We have 3 vendors we are drop shipping with and as of right now we have integrated into only 1 of those vendors. Getting orders to the other 2 vendors involves emailing, formatting .csv files, manual followup, and manually entering tracking numbers into our order management system.
This has been hard on me and some of employees. My personality is not one that easily tolerates imperfect systems and many of my employees are used to well designed processes that force standard protocols on them, and most importantly don't allow for failure.
Overall the introduction of drop shipping has been a huge home run for us. The key to this success, I think, is that I knew there would be dropped balls and mentally prepared myself for it. That way when the process broke it was not a failure, it was an inevitability. We let our customers know when we messed up, we tried to make amends, and we moved one without dwelling on it.
This lesson of moving fast and tolerating broken systems is one I've learned in the past, but I find the need to remind myself. We were hacked in 2012 and because of that 2013 was a time of accepting just barely good enough solutions to get out from that mess. We still don't have the amazing website I would like, but we're operating and making progress. I've got a great front end developer working with us and we are regularly launching small and large improvements.
So the question, and the real reason I'm writing this is because there is only one acceptable answer to this question and I want to put this out there publicly so I feel embarrassed if we don't follow through, is why haven't I done what I've wanted to do for 10 years? I've owned two domains for a long time, one of which has been trademarked for a long time. The intention has been to launch new t-shirt sites to take advantage of our infrastructure. The truth is my ambitions are even greater than this but I'm not willing to hold myself accountable for more than these 2 sites.
So come hell or high water, by June 30, 2017 you will be able to make a purchase on www.90stees.com and www.LicenseToWear.com.
This might mean that we have a very simple storefront and that we hand key orders on our vendor's websites and then hand key the tracking numbers to Shopify, but the sites will be up. We will be the duck.