In December 2007, I left a cushy job to start a company.
That company failed.
This blog outlines that story.
In December 2007, I left a cushy job at EMC as a Senior Software Engineer to start my first company, MessageSling.
I left to start the company w/ Scot Junkin, a friend and fellow geek from WPI. We started without funding. We started without experience. We started without even a clear idea of what we wanted to do. But we started because we needed to.
Eleven months later, we were out of money and I was broke; I was consulting to try and pay the mortgage on the house I just built; and was certain I had done irreparable damage to my relationship with Scot.
In February of 2009, I started working full time for Punchbowl Software. MessageSling stayed running.
In December of 2009, the combination of 10 months of neglect with an Amazon EC2 instance failure caused the service to suffer a catastrophic failure. And in January of 2010, two years after starting MessageSling, we put up this page.
I’ve had a lot of time to reflect on what happened. The highs, the lows, the fights, the wins, the lessons, the consequences. And now I want to open the kimono. [1]
So today, I’m introducing “The Day Series”, a blog that will outline in excruciating detail everything. Everything that happened in the days leading up to starting MessageSling, running the company, raising funding, running out of funding, getting a full time job, shutting it down, everything around and in between.
It will also detail how I still became Scot’s Best Man.

Me (on the left) & Scot
This will not be a chronological catalog of events. It will be a random semi-stream-of-consciousness dumping of what I recall. Each post will outline key days as I remember them.
Scot is on board with this blog, and will be at the very least proofreading all the posts. I expect him to make a few guest posts from time to time.
I want feedback. I want criticism. I want discussion. If you have a question or a suggestion for a post, let me know either in the comments, via @angilly, or ryan@angilly.com.
So with no further ado, I give you The Day I (tried to) leave EMC.
References
[1] A friend of mine who I respect a lot didn’t know what this phrase meant. But I didn’t want to take it out, so you get a definition :)
Thanks
Thanks to Tim Downing and Kate Angilly for providing feedback on drafts of this post.
I just got back from dinner with a buddy of mine from college named Chris. We hadn’t really talked in years, and just randomly decided to get together and catch up.
We talked about what he’s doing, what I’m doing, reflected a bit on MessageSling, and then, mid conversation, he hit me with a ton of bricks:
Chris: Ok I gotta ask —
First of all, I use that line. When I preface something with that line, it’s usually a precursor to something… difficult. Chris didn’t pause after those 4 words, but I immediately thought to myself “oh shit.”
Chris: Ok I gotta ask, what was with that time you sent me that email saying ‘Unfortunately, you are not going to be joining our team at this time’ ?
…
What?
Chris: “Yeah we were talking about working together and I was really excited about it, and then I got some weird email from you and that was it. Done.”
…
?
I had no idea what he was talking about. I pressed him a bit, and some things started to come back. Back during the spring of 2008, MessageSling had just received a bit of funding. Chris was getting his MBA at Babson, and approached me about working with MessageSling. He was really excited about working with us. We chatted informally, tried to setup a couple times for the three of (Chris, Scot, and I) to have a few beers, and then one day I sent him an email that was short, curt, and awkwardly formal which quickly ended all discussion on the matter.
The reasons behind why I sent that email are a bit cloudy. I think the genesis for it was a conversation Scot and I had around how much help we could get actually get from an MBA student. We couldn’t pay him. We were concerned about equity. He’s only a student. He would only be around for the summer. He would only be part time. He isn’t in Sturbridge. Blah blah blah. The details aren’t the point of this post, and I’m pretty sure that cutting him off like that was a mistake — when someone wants to help you, you should never turn them down.
The point of this post? That day was 26 months ago. Chris has been thinking about this for 26 months. I never gave it a second thought. The first time we chat after two years, he brings it up. He prefaced it with “Ok I gotta ask….”
This really bothered him.
He wasn’t trying to start an argument or trap me or throw me under a bus, and he wasn’t being a dick about it. He just wanted to know why. It really froze me. I felt like he deserved to know why. I felt terrible that he had wondered about that for years. I owed him an answer, but I couldn’t give him one. I really don’t remember all the details.
This is a startup example of something I’ve noticed in other areas of my life: sometimes an action which can seem inconsequential to one party can mean a great deal to another.
This wasn’t some random biz dev guy at another company — those guys you can snub when there’s too much going on :). This was a smart friend reaching out. Not only did we not accept his help, but I basically told him to fuck off (in an email!) and never gave him an explanation. You can’t do that to people.
Moral: As a startup founder, you’ve got to keep in mind how your actions affect other people even more than usual. A small one line email that takes you 10 seconds to write can reverberate though someone’s mind for YEARS making them wonder: “Why?”
Bonus Moral!: Another thing this little blog post highlights is how valuable keeping in contact with people can be. Out of it, Chris finally got a bit of closure (we didn’t hate him). I was reminded of how small actions can mean a lot to other people. And you got this blog post :)
Thanks
I want to thank Chris for proofreading this draft and letting me post it.
We started MessageSling in two places: Scot’s house, and the SnowHo ski house in Killington, Vermont. During the weeks, I’d head over to Scot’s house. On the weekends we’d head up to the mountains for 3 or 4 days at a time. We’d get a few hours of skiing in each day, and work the rest.
It wasn’t as awesome as it may sound.
Sitting on a couch or at a kitchen table on a laptop all day, day after day, really starts to suck after not that much time. I seriously was getting on Jen’s nerves. Their dogs got on mine. And we originally joined the ski house to party; the fact that we were now working did not stop anyone else from pursuing that original goal.
The Space
So we decided to get office space. We didn’t go crazy. We kept it cheap: renting a windowless 150 sq. ft. office from a biotech company in Worcester. We bought a couple used desks, a locking file cabinet, and some chairs from a used office supply warehouse next door. We got a whiteboard and a couple 21” monitors from Staples. We didn’t put our name on the door. The wireless internet that we shared w/ the biotech company was always going out. It was a perfect startup cliche.
Scot and I would spend most of our time there. We had CJ coming in regularly after a while. Greg would stop by one or two days a week. Tanya would come in one day every week or so. There were a couple conference rooms that we used to have brainstorming meetings, code reviews, or calls with the DEMO people. It felt very “office-y.”
One day we decided we should have our investors come visit. We were going to give them a demo in the conference room, show them the space we worked in, and give them a state of the business report.
The Visit
They called Scot when they showed up. He went out to greet them. We had spent days getting everything ready. Making sure we had the presentation down to every last detail. Scot had all the cashflow numbers to show them. These guys cut us pretty substantial checks, and we wanted to show them what we were doing with it.
I was pretty nervous. They were always super nice and friendly, but I hadn’t seen them since Scot picked up the checks. Since then, this had become a REAL business, and I had never dealt with that before. They came in, and I forget exactly what was said, but I can remember that I was standing in the back corner of our office. I was facing them — they were all standing as well — explaining to them the state of the technology and where we were at when one of the investors cuts me off.
Investor: (in a serious tone) I have one question for you…
Investor: (3 second pause)
Investor: (breaking into a huge smile) … Are you happy?
I don’t know if I was able to keep my eyes from watering up. I know that I didn’t need to give him a verbal answer. It was all over my face. Of course I was happy. I was literally living a dream.
To this day thinking about moment really gets me. That day is a good explanation of why I love startups so much. Because I get to meet people like that. And some day, one of these startups might end up putting some cash in my pocket. And then I’ll be able to cut checks to some young kids who have nothing but some brains and a dream. And I hope some day I can stand in a shitty subletted office, look across at those kids and ask them: Are you happy?
I hope it’ll have the same effect on them that it did on me.
Tags: MessageSling, investors, office space, inspiration,
The Day I found out my cofounder gave himself a raise
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