The Day Series

The Day I found out my cofounder gave himself a raise

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 can't believe it's been 2 months since my last post on this blog.  Seems I have some 'splaining to do.

To make a long (two month) story short, a lot has gone on in my life recently.  In the past 2 months I have:

Quit my job

Driven across the country in a UHaul w/ my car in tow

Broken up with a girl that was crazy -- and that I was crazy about

Flown across the country twice

Interviewed at 6 companies

Had one hell of a going away party

Spoken at 2 conferences

Met about a hundred new people

Said goodbye to a lot of good friends

Was asked to speak at another conference

Had a dizzying first kiss with a girl

Un-quit my job

Wasn't able to say goodbye to a lot of good friends

Gone to TEDxBoulder

Sent a LOT of drunk text messages

Fallen in love with Pearl Street

Completely changed the way I work & live

So there's been a lot on my mind.

To summarize with a bit more narrative

A few months ago I decided to move to Boulder, CO.  This was something I'd wanted to do for several years.  Ever since I drove out here in 2004 for a month to ski during my grad school winter break, I've felt an affinity for Colorado.  I didn't want to live in Denver, and from what I had heard Boulder seemed cool.  Then TechStars landed in Boulder, and the town started to get a lot of national attention for all the tech & startup work coming out of there, so it was an obvious choice.

Why move now?

There were two times I almost did it.  The first time, I coincidentally got my first "real" job out of grad school at EMC.  At the time, all I saw were dollar signs; so I stayed.  The second time, I instead decided to built a house because "it'd be a great investment!"  It would only be for a year, and I'd make $100k because real estate was hot; so I stayed. This time, the catalyst was a girl I was dating.  Notice I said was :)  After we broke up, I spent a few weeks trying to figure out whether or not the move was "for her."  I realized it wasn't, and decided to take the plunge.  I gave notice at work, flew out to Boulder, interviewed, got offers, mulled some stuff over and decided that the best thing for me was to stay with Punchbowl.  They let me un-quit.  I now work from home and I will be flying back to Massachusetts one week a month.[1]

So what?

Why I am telling you all this?  It's definitely outside the theme of this blog, but I wanted to give you all some context as to where the hell I went.  Living in a new place and not knowing anyone translates to something: alone time.  Not lonely time, but time alone.  I've been able to settle into a rhythm that is leaving me with a feeling of being refreshed and revitalized.  My "list of topics" for this blog has grown by over 20 in the past week, and starting tomorrow I'll be blogging them regularly.

Thanks to all those people that have got in touch with me in the last few months -- both strangers and friends -- who asked why I stopped writing.  I was surprised that anyone even notice.  To those people, and everyone else: be seeing ya'll soon.

-Ryan

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 :)

When Scot and I left our jobs to start MessageSling, we didn't know we were going to start MessageSling.  We didn't have the name.  We didn't even have the idea.  We just knew we wanted to be in this sweet spot:

It's pretty funny admitting it, but when we left our jobs, we had a better idea of how we were going to launch our company than what our company was actually going to do.

My cofounder, Scot, came from Jingle Networks, creators of 1-800-FREE411.  FREE411 launched at the DEMO conference in 2005, and Scot saw firsthand what kind of exposure came from the conference.  The way DEMO works is that first you get accepted, then you pay $18,500.  In return, you get 6 minutes on stage to pitch your product.  It's 3 or 4 days long and launches 60+ companies every six months.  It's a big media production.  Tons of press, investors, etc....

We were going to launch at DEMO.

Now when I say launch, I should probably say that we assumed our launch had to be a huge thing.  Not just a press release and a mention in a blog.  It had to be a big deal.  We had to have a major launch and get tons of traffic right away and get in front of investors and get user feedback and there was no route that was 'just' grow the business slowly over time.  That was my mindset anyway.  I won't say that it was wrong, because that option can work for people who have all their ducks in a row.  But it was uneducated and narrow in the sense that, as far as I was concerned, that was the only way to do it (and we didn't have our ducks in a row... but c'est la vie).

And then something neat happened, TechCrunch announced a new startup launch conference called TC50, and it cost about $18,500 less than DEMO.  TC50 was free.

TechCrunch is hip.  They have a huge readership.  TechCrunch's founder, Mike Arrington, does not fuck around.  It was clear from the initial announcement that TC50 was going to be big; that it would rival DEMO in terms of the exposure it would give to the companies that launch at it.  And it was free!  Applying to TC50 was a no-brainer.

Then came a very interesting day.  We got past the first stage of the application process with TC50.  We had a call scheduled with some of the TC organizers to discuss MessageSling.  I'm not sure how many people got to this stage, but when you launch 50 companies at a conference, you can't spend 30 minutes on the phone with too many so I'm thinking it was a big deal.

The call was scheduled for a Wednesday evening.  Wednesday afternoon, we found out we were accepted to DEMO.

We had a decision to make, and we had to make it quickly: a guaranteed launch for $18,500 or a (what we thought to be decent) chance at something comparable and free?

Would TC bash us if we flat up turned them down? No idea.

The world is small, and people talk.  If the DEMO people heard that we were interviewing for TC50 after we were accepted, would they yank our spot?  I dunno.

If we just said no to DEMO, was it worth the risk of not getting our big launching?  Umm, can I have more than 2 hours to think about this?

I remember the conversation being quiet.  Scot's house was quiet.  Jen (his then girlfriend, now wife) wasn't there.  Dogs were quiet.  No music.  No rain.  Just the two of us standing in his kitchen.  The heater wasn't on.  Laundry wasn't going.  I was sitting at the breakfast nook.  Scot was leaning up against the sink countertop.  It wasn't a debate.  It wasn't an argument.  For an hour we sat there, talking, not knowing what to do.

It's worth throwing some facts out there to put things in perspective:

We started MessageSling in early January 2008

We raised $50,000 in March

We were accepted to DEMO on July 24th

Our call with TechCrunch was scheduled for July 24th

We had already hired CJ

The initial payment for DEMO was $9,000

We were going to run out of money in September if we went to DEMO

We were going to run out of money about 10 weeks later if we did not go to DEMO

When we ran out of money, we would still owe DEMO $9,500

We ended up calling TechCrunch, and told them we were going with DEMO.

I can't speak for Scot, but I can tell you what I was thinking at the time: DEMO was a sure thing.  I was not confident we would make it into TC50.  I knew that the voicemail transcription space was already packed with competent competitors.  And given that, I was a tad surprised we got into DEMO.  I didn't think we would get lucky twice.

If I could do it over again, I would do the exact same thing.  I would do the exact same thing because I like where I'm at in life.  I would never go back and change a thing because I don't know how it would affect my development.

That being said, if I ever come face to face with that kind of decision again, I'll have the full conversation with TechCrunch.

Why?  Because we had delusions of grandeur.  Those questions I posed up above? Stupid.  Would DEMO yank our spot?  Would TC bash us if we turned them down?  No. Neither.  Why would they?  We were nobody to them.  We were just a couple of kids that sent a couple emails.  We were in a bubble having a completely unreasonable and wasteful conversation.  TC and DEMO were only concerned with having a full conference of great companies.  We should have gone as far as possible with TechCrunch, possibly even told them we were accepted to DEMO:

Look guys, we just got accepted to DEMO, but we're obviously interested in you because you're the new hotness, a hell of a lot cheaper and we're short on cash.  If we continue things, how soon would we have an answer from you?

That would have been the right play.  And it will be the right play next time :)

His name was Robert Paulson.

  Just kidding.  His name is CJ.  We hired CJ right out of WPI to be a developer for MessageSling.  CJ's a bright kid.  We met him at a "Meet the Entrepreneurs"-type dinner hosted by WPI's Venture Forum a couple months after starting the company.

When it came time for school to end, CJ came knocking on our door.  The decision whether or not to hire him -- really the decision to hire ANY engineers at that stage -- was a tough one, and there will be another post about it.  But for this post we'll focus on the fact that we hired CJ, and ended up letting him go.

It wasn't CJ's fault.  We ran out of money.  When CJ started, we made it very clear to him:

CJ, we have very little money.  We can currently only pay you through 6 months.  Our runway could be even shorter if anything else comes up.  BUT.  We -- me, I, Ryan Angilly -- promise you that we'll let you know with at least a month notice if that's gonna change so you can line something else up.

I ended up breaking my promise.  When I let CJ go,  I told him he was getting his last paycheck in a couple days.  Not only that, but the company didn't actually have enough money to pay off CJ's last paycheck.  We ended up paying some of it out of pocket.  

I never got all the details, but an accounting error gave Scot the impression we had a lot more money than we did.  One day he told me we would be out of money in a few days.  I felt sick. 

At the time, though, I wasn't mad at Scot at all.  He didn't have any experience keeping track of money at that level.  Quickbooks is a nightmare.  We were doing this crazy thing where our "salaries" were >$100k, but we were only taking a fraction of that and keeping track of the difference as a "loan" that we were giving the company.  He was doing his best.  On my end of things, this was "My First Rails App ©" so there were plenty of app deficiencies that he had to put up with from me.

As an aside, I will say that our financial setup was unnecessarily complicated.  We were a startup with $50k and no revenue.  It was a disaster waiting to happen.  Any Series A we raised surely would not have honored our "loans" to the company, and any oddities in accounting would have been cleaned up by their number crunchers after the fact.

So Scot tells me we're basically out of money, and I'm dreading talking to CJ.

I tell him.  And guess what?  The world didn't end.  He didn't reach across the table and try to strangle me.  He didn't come in and shoot up our office a few weeks later.  My tires never got slashed.  He was even nice enough to proofread this post for me.  This was a startup.  CJ knew that.  I think all startup employees need to really understand that.  You can get axed at any time whether it's "your fault" or not. 

Moral:  It really sucks having to let someone go.  It's even worse when it's not because they suck at their job.  But it comes with the job.  Make sure people understand that when you bring them in.  CJ did, and it worked out.

UPDATE: Everybody loves CJ!  Comments via email and over at Hacker News made me realize I should have given you all an update on what CJ is doing now.  Well, he's doing just fine, and told me if you want to chat with him, feel free to send him a note at @waltz. 

For those of you who don't know Randy Pausch, do yourself a favor: block off 80 minutes, and go watch this.  76 minutes for the video, 4 more to wipe the tears from your face and blow your nose.  Seriously.  If "the second head fake" doesn't make you tear up, check your pulse.

I left EMC to start on MessageSling in December of 2007.  By mid July 2008, things were in full swing. We had raised $50k, moved into some office space, hired a junior developer and had just been accepted to DEMOfall08.  Things were going well.

I was on a camping trip that weekend.  It was planned by friends of my girlfriend at the time.  We drove up to somewhere in NH, camped out for a couple nights, and rode down the Saco River in between.  Weather was pretty nice, people were friendly, there was plenty of beer, and I was fucking miserable.

Not because I got sunburned or forgot my sleeping bag.  I was miserable because I didn't have broadband.  By this time we already had customers.  We had the eyes of DEMO looking at our product.  But since this was "My Very First Rails App ©" there were no tests, random exceptions (syntax errors being checked into production were not uncommon), poor process & system monitoring on EC2 (what's monit?).  Basically, anything could go down at any time, so we had to be constantly on alert.  The way Scot and I split the technical work up, the phones were his domain, and the web was mine. There was really no "hey keep an eye on things for me while I'm gone" -- there was nobody that could keep an eye on things.  It was always on both of us.

I couldn't sleep the second night.  Around 5am, the sun started to come up, and I decided that trying to get any sleep was hopeless.  I cracked open my Blackberry and started reading my RSS feed.  That's when I saw that Randy Pausch had just died a few days earlier.

I put my phone down, rolled over in my sleeping bag, and started to cry.  But not because I was sad for Randy.

For those of you who didn't take my advice and watch Randy's talk, a quick rundown. It's about following your childhood dreams.  Randy was diagnosed with pancreatic cancer in 2006.  In late 2007, as part of an ongoing series of talks at CMU called "The Last Lecture Series," Randy talked about realizing childhood dreams.  At that point, he had gone through all of the available procedures, and his prognosis was terminal. Despite that, he gave the most inspiring, energetic, brilliant, moving talk that I have ever seen.

So why was I crying?  I was in this cold tent.  Miserable.  Tired.  Nervous.  Stressed out. I had just wasted a weekend bitching about everything, pissing off my girlfriend, being mean to all her friends, and "worst of all" not getting any work done.  And suddenly I'm confronted with the death of a guy who looked TERMINAL CANCER in the face, held up his middle finger to it as he laughed and used his last lecture to tell the entire world to enjoy life to the fullest and achieve their dreams.  

FUCK.

A startup can be a destructive force.  Not only did MessageSling destroy my bank accounts, strain my relationships, and affect my health (I gained weight during this time), but that morning I realized something even more terrible was happening: my beloved startup had started to chip away at my spirit.  Unacceptable.

I wish I could say I flipped a switch and all was better after that day, but it wasn't. Those realizations, just like realizations of being overweight or lazy, don't mean that the problem will just fall away.  But you can't fix a problem until you're aware it exists. Until that day, I was blind to what was happening to me.  Afterwards, I was aware.

It's been almost two years since that morning in NH.  It was pretty crappy, but I wouldn't do a thing differently if I could do it over again.  Because over the last two years I've learned the hard way that the day's moral is more than just a witty one-liner to finish a blog post:

In college I tried to start a company three times.  Twice I entered local business plan competitions.  Once I applied to this new cool thing in Boston called Y-Combinator and got called in to meet a couple nice guys named Trevor and Paul[1].  All three times I came up short, and never got around to scratching that entrepreneurial itch.

In high school, I impressed my AP calculus teacher by completing the textbook in a weekend (I got grounded for swearing at my sister and had nothing else to do).  My teacher's husband was a Director at EMC.  He got me an internship in the Performance Engineering group.  I interned there throughout college and worked there full time for almost two years after completing my Masters.  It was a fun environment full of great people -- not exactly the doldrums depicted in Office Space.  But at the end of the day, it was a large corporate environment.  And no matter what I did, I never could shake that feeling of being out of place.

After a little over a year I put in for a transfer into a new "startup within EMC."  There were three different product lines in EMC's midrange storage division.  The mandate of this "startup" was to merge the codebases of all three lines and produce the ultimately flexible storage system.  The "startup" was pulling in top talent from all over EMC and bringing them all to the same building in Southborough, MA.  This felt right.  It felt like a place I'd really fit in.  It sounded awesome.

It wasn't.

Only 6 months went by before I was beginning to see the writing on the wall: anything I did wouldn't see the light of day for another 2 or 3 years.  Even though I was surrounded by kind, bright people -- I just didn't fit.

Aside:  I want to take a second to admit that I know how this all sounds.  I've always been a stubborn, playfully-arrogant little bastard.  When I would explain my situation at the time to some of my friends,  some called me right out on it: "You're complaining about a great paying job working with great people that respect you.  STFU and get back to work."  But it wasn't enough to make me happy.  And I think that -- that feeling of not fitting in, that feeling of not being happy, that drive to do something about it -- is an important part of what makes an entrepreneur.  I'm not going to apologize for it.

So in October I went out and got myself a job offer.  It was a monster offer.  The company was small, but they had raised a bunch of money and been around for a few years.  It wasn't exactly a "startup" but it also wasn't a huge corporate entity.  I walked into Jeff (my manager) office, and told him I was done.

And then we talked for a while about why I was leaving.  I told him I wanted more responsibility; that I didn't feel like I fit.  And Jeff said we could work on that, that I could move around, that EMC had a lot to offer.

And then I met with his boss, Doug.  I told him I was being offered a monster increase in salary, and Doug said they'd work with me in terms of salary, bonus and stock options to increase my compensation.

And then I met with one of the other managers under Doug Wood.  We talked about moving into his group and giving me some exposure to building web services and writing C++ and learning Flex.

It took just about two hours.  I changed my mind.  By the end of the day, I told the other company I was turning down the offer.

I chickened out.

A couple months went by and there was no change in my responsibilities.  I was in the same group.  I was given a few more stock options.  Still didn't fit in.  Still didn't feel right.

I want to be fair to everyone at EMC.  I don't think any of them outright lied to me that day.  I just think we were speaking different languages.  I was probably the one that did most of the lying.  Lying to them when I feigned excitement at what they were offering, and lying to myself as I drove home telling myself I did belong at EMC.

In the end, everything worked out the way it was supposed to.  Going from one company to another wouldn't have made me any happier.  I wasn't just afraid that day, my gut was also signaling that I was about to make a mistake.

When you're about to make a life-changing decision -- like leaving your job for a new opportunity -- there's a difference between being afraid and your gut telling you that you're making the wrong decision.  That day at EMC I had both.  The next time I tried to (and did) leave EMC, I only had the first one.  I was afraid, but I knew that I was doing the right thing.  But that story is another day.

Moral:  Listen to your gut, and tell fear to fuck off.

References [1] For those not aware, this is a joke.  Y-Combinator is a huge deal.  I happened to apply the first year they existed, and I met Trevor Blackwell and Paul Graham.  It was pretty cool :)

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 [email protected].

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 :)