The good stuff sticks – Creating Freewrite, Part 2

  • December 29, 2016

In the last post, I told the origin story of the idea for Freewrite. At the time, it wasn’t called Freewrite; it wasn’t even called Hemingwrite. It was just an idea.

Time went by, as it tends to do. From February until July of 2014, Patrick and I both sat on it. I wrote down the idea on my Projects List in Evernote and continued working on SunDaily.

But the good stuff sticks.(1)(A) This idea for a distraction-free hardware thing churned around in my mind despite my energy being spent elsewhere.

To set the scene, in Jan 2014 I had just recruited an old friend and former roommate of mine to join me at SunDaily. The rest of my small team had dissolved by that point so it was just down to the two of us. We had some good months. April of 2014 was our best with a whopping $3300 in vitamin sales. Jim was hitting the road and selling at gyms and chiropractor offices in the Metro Detroit area. We were sharing a car (my mother’s 10-year-old minivan) since I wasn’t paying him enough to get his own. It was insane but we were desperately trying to make things work. There were sparks of excitement and a lot of prospects for growth but ultimately we knew we were basically out of time (i.e. money).

At about the same time, Jim was desperately needed on the west coast for family matters. Recruiting Jim was my last-ditch effort to get SunDaily to break out so when Jim left, I finally had a very clear signal that SunDaily’s time was up.(2) I had struggled enough for the previous two years by myself that I had no interest doing that again. I had put tens of thousands of my own hard-earned savings and years of my life into SunDaily but it wasn’t even a hard decision at that point. I was burnt out, very broke, and I knew that I desperately needed a break. I also had given it all I could. My 28th year of life, the summer of 2013 (the start of Bizdumb) until the summer of 2014, was my most stressful, by far. It handily beats out any year I spent at MIT or on Wall Street, recession and all. That year was terrible and I frequently think about it as a place I never want to be in again.

Once Jim made the decision to leave, I took a really deep breath. It was probably my first deep breath since April 2013 when I started selling. After spending so much time staring at a computer, I remember thinking that I needed to do something with my hands again that didn’t involve juggling a business.

It was then that I started thinking much more seriously about this project that Patrick and I had talked about some months ago. In my mind it had legs. I really liked it.

The idea was starting to take shape too. I had a basic industrial design in my head that was visually interesting. The primary components were already spec’ed. Patrick could cobble together a software prototype on an E Ink screen using a hacked e-reader (I hoped). I could integrate an off-the-shelf 60% mechanical keyboard into a housing that would hold all the components. Most importantly, I thought other people would find it interesting once we showed it to them. Whether they would buy it or not was unimportant to me at the time. All I really wanted to do was get back in the workshop and work on something interesting.

Lastly, if it got some interest, I thought it would be a perfect candidate to put on Kickstarter. Since crowdfunding came across my radar some years ago, a seed was planted in my head that I wanted to run a campaign one day. But I couldn’t just put up any idea on Kickstarter and expect it to sell. The format of Kickstarter and their users are not amenable to just anything. SunDaily was a terrible candidate. My other ideas up to that point didn’t quite fit either. But this distraction-free thing could be perfect. It was a real product that people could touch and feel. It was unique both visually and philosophically. It had elements of nostalgia while at the same time was very techy/progressive. It could work if we did it right.

Patrick was my next challenge. This project was not happening without him. I had no interest in going back to working alone. I was fine doing my pieces of the project by myself but I needed somebody else to have true ownership, it couldn’t just be me. Plus, Patrick and I had very complementary skillsets. We also both saw very eye to eye on the overall product design. Truthfully, I had never met anybody that had the same opinions on product design, let alone someone who also brought hard engineering skills. It was a match! But he wasn’t onboard right away. He was living his own life and working on Gridpar.

It was all a little too serendipitous. At just about the same time, Patrick’s business partner left to go back to graduate school on the west coast leaving him at crossroads as well. I continued to pepper his inbox with various thoughts and ideas about the project.

At some point during the summer, Patrick and I sat down to have the talk, “do you want to work on this thing?” I did and he did too. But how? Both of us agreed that we needed a deadline or else it would be one of those never-ending projects that we did in our mythical spare time. A little searching the internet found us a hardware competition called Insert Coin that was sponsored by Engadget. The deadline for applications, which required a video of a working prototype, was Sept 26, 2014. We had approximately 3 months to get our shit together. We agreed and parted. (Insert Coin Contest Page)

A solid month went by. Patrick and I met up again to have another talk. “Are we really going to do this thing?” I was as motivated as ever. Patrick was still interested. I figured we needed to go all in the next two months or this thing wasn’t happening. He agreed. After that, everything ramped up extremely quickly. We needed to build a working prototype in record time with a micro budget.


July 14, 2014 email to Patrick

(A) On July 14, 2014 I wrote this email to Patrick revealing some of my excitement about the project (and a hint to both of our future names).


(1) I could make an argument that this concept is so powerful that it is detrimental to keep a list at all! The advice would be to only work on things that are truly memorable. If it is memorable to you, it is much more likely to be memorable with someone else. Likewise, if the idea is not memorable to you, it would be hard to expect it to be any different to an outsider. I try to use the passage of time as a tool by letting the mediocre ideas whither and the best ideas rise above.

(2) Knowing when to quit is one of the hardest things I have experienced as an entrepreneur. I hope to write a future post to elaborate.