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Bay Area, CA
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Humphrey started Craft Oak in 2017. They detail the beginnings of their company in their Starter Story interview: 
Q: How did you get started on Craft Oak?
My backstory is that I had quit my job at a mobile gaming company in Nov. 2016, where I had been working for nearly 3 years in monetization. My goal at that job was to monetize our users via in-app purchases based on data that was available to me within the game’s ecosystem.
I had always wanted to "start" something on my own, and when I was talking about doing that in January of 2017, I was approached by a friend who wanted to also start something - but for him, it would be a side gig because he had a full-time job already. This friend would become my business partner, and still is a part of the business today - he would like to remain anonymous for the purpose of this Starter Story.
The idea to start this business in the custom poster space was actually my business partner’s, he saw it being done in Europe at small custom gift shops, and we had done some market research and saw some other incumbent websites doing the same thing.
I was just eager to get started on working on anything (as I had been unemployed for about 2 months at the time and was not sure of what to do next), but I knew I wanted to try my hand at a direct-to-consumer type of business. Looking back on it now, I’m thankful for the experience and where we are with our business, but I do believe direct to consumer is a really tough grind and requires a bunch of luck. I read this article by the Twitch founder, and basically he says that "B2C is a gamble while B2B is (more) within your control." and I tend to agree, it’s tough to argue with his viewpoints.
Anyway, I had some money saved up from working at the gaming company, and both my partner and I put around 10,000 USD each into the business, for a total of 20k. We started an LLC, a bank account, and contracted one of our contacts to start making us a website.
To be honest, I had zero experience in e-Commerce, but I did know from my previous job that I was good at learning from data, setting up and creating experiments over and over again, and making business decisions with the information provided to me. I try to do my best in making decisions without any ego interference. I personally believe that this is one of the most important qualities you can have to being a successful entrepreneur. Another thing I try to avoid is to make a business decision based on a singular anecdote.