That Startup Hustle

This story will be the first techy kind of post that will be spattered here and there on the blog going forward and is also a little bittersweet.  For around 3 years I had the privilege to represent arguably one of the best storage platforms built for virtualization and to work with some truly brilliant and amazing people.  Join me will you, for the recollection of my adventure at startup company and the ups and downs that made the journey awesome and heart wrenching. 

If you have not ventured onto the about me section then I’ll do a quick recap before we get into the meat and potatoes, ya feel me?  Before joining the startup company I worked as a Systems Administrator/Analyst/IT Generalist, the title really depending on the employer but effectively I managed IT infrastructure.  My favorite stuff to work with is VMware and networking.  In the early 2000’s I attended a Microsoft TechDays (RIP) and it blew my fucking mind.  It was the first time I saw Technical Evangelists and oh man, I was like people get paid to get excited about tech and get other people excited about tech, I WANNA DO THAT TOO!!!111!!1!!  That lead to learning about how those people became evangelists so I could make my way to be one too.  On that journey I learned a lot, I did a lot, I failed a lot, I built some really cool shit and I also met the next awesomest job I’d seen Systems Engineer.
<rant> We are no longer allowed to call ourselves “Engineers” in Canada because real engineers in Alberta and Quebec got upset that we did not earn the title by spending lots of money on school and buying a super sweet power pinky ring, we just devoted years towards honing our craft to become the best in the game so that we could help people solve specific business problems with technology.  So now it’s consultant or some other word that is non-offensive to the power ring holders </rant>

But how did I end up at a startup? well damn I’m getting there ok hold tight.  So I put in some time as a public servant for a large provincial government organization and the opportunity arose to do a really wicked awesome project.  Something that was going to be huge and change my life forever, and something that involved all of my favorite things with the most important one being VMware.  Through this project I worked very closely with several different vendors to achieve great success, albeit there was a ton of failure.  But like Mr. Watson said “The way to succeed is to double your error rate.” eventually we found something that worked, and it worked well.  Through my interactions with VMware I was invited to join an organization called the VMware User Group (VMUG) now I could ramble on a ton about VMUG and I likely will in another post but this is not about VMUG.  This is about how I learned to stop worrying and love the dark side, I mean startups. 

I first met Tintri at a VMUG meeting and I was confused as heck, I didn’t really get it.  Up to that point most of the storage systems I had worked with or managed were kludgy and frustrating and expensive, until Nimble.  Nimble Storage made traditional storage kind of sexy and easy to consume.  As I was watching the Tintri presentation I couldn’t help but think it was just a reskinned Nimble that was really overpriced and I dismissed them.  The second time I met Tintri was at another VMUG meeting and I realized that I had made a huge mistake.  They were not a reskinned Nimble, they were something else, something special.  Tintri is the first shared storage platform created specifically for Virtualization and that was where I made my mistake.  All my experience before I met Tintri was with traditional storage platforms, systems that were built originally to host physical workloads and then adapted for virtual workloads.  I was trying to fit Tintri into knowledge buckets in my head shaped for traditional storage systems and when it didn’t fit in them I threw it out as bullshit.  Tintri was a lot of things but bullshit was not one of them (the product specifically, there was plenty of bullshit elsewhere) Tintri was amazing and I WANTED TO WORK THERE!

The third time I met Tintri was at the VMUG User Conference in Vancouver BC, the user con for those in the know is like a mini version of VMworld or a tech conference if you’re not familiar with VMworld.  Now that I had realized how awesome Tintri was I went up to JD the man who had been presenting at the VMUG’s previously and said “Hey man, your stuff is pretty rad.  If you’re ever thinking of coming into Western Canada I’d love to work for you guys” and then I handed him my number.  Sometimes you should be careful what you wish for because about a week later I got a call from the man who would be my first manager at Tintri, we spoke for a while and then he said the VP of Technology would be reaching out to me.  The next day I received a call from Rex, the then VP of Technology and had one of the more interesting conversations I’ve had in my career.  Before moving on I have to say Rex is a very interesting cat and I am honored to have worked with him, I learned a lot in my short time working with him and have the utmost respect for him.  If you ever have an opportunity to work with or share time with Rex Walters, jump on it!  Anyways Rex ended the call with it wasn’t up to him but if it was the job would be mine and that I would hear from someone soon.

A few days after my call with Rex I received and accepted my offer, I resigned from the company I was working for at the time and really had no idea what to expect.  The next two weeks were kind of long, trying to wind down the old job and thinking about what this new job in a new realm was going to be like.  My shiny new MacBook Pro showed up in the mail just before my start date and I logged into my email.  One of the first things I was going to do was head down to VMworld, now this would be the second time I’d ever attended.  If you know about VMworld then you know it’s like nerd mecca, we all want to go there and for years I had only dreamed of it.  VMworld 2013 I scored a free pass via VMUG so my partner and I drove down from BC to San Francisco for the pilgrimage, it was amazing.  Silicon Valley blew me away, we went to the computer history museum and I saw things I had only read about.  I learned about all the startups that made Silicon Valley and ultimately the field that my career was based in.  Drunk with what i saw in the bay area I wanted to be at a startup.  VMworld 2014 was the second time I’d ever been and this time I was there in a shiny new company polo shirt attending as a newly minted Senior Systems Engineer and I had no idea what I was in for.  It was wild, I learned a lot, met so many people and my liver hated me for weeks.  VMworld deserves a post of its own but we finally made it, I was working at a startup and I was in the role that I wanted to be in. 

The first year at Tintri was crazy, I was covering Western Canada so that meant I lived on a plane.  I was averaging over 300 flights a year, I leveled up with the travel status things and became a road warrior.  Most of my job was meeting with customers and talking about their infrastructure and seeing if there was a way we could help them with our technology.  Another function of my job tho and one that I was super stoked to dive into was evangelizing the product at tech conferences and meetups.  I killed two birds with one stone, I was doing Technical Evangelism and was also a Systems Engineer.  It was really rad, I love doing that work, meeting people and getting them excited about technology.  I loved the job so much, it was pretty amazing however it did have a few dark clouds.  There was lots of company drama, corporate seemed detached from the field and they were making decisions that didn’t make much sense to us in the field.  Some of them actually really hurt our ability to execute as effectively as we could have.  We tried to share our thoughts but they seemed to land on deaf ears.  My personal life was also in a dismal place so I doubled down on working and travelled more, that reached a critical mass when I started to burn out from travel.  Who knew there was only so much travel a human body can tolerate before systems start to breakdown, I didn’t but boy did I ever learn the hard way.

After 2 and a half years the travel and my personal life really took its toll, I needed a break.  I resigned from Tintri and worked as a Solutions Architect for a friend at a networking company.  It was nice to not travel anymore and to wake up in one place for more than a few days at a time.  People who travel get it, shit gets kinda janky after a while.  But I do know how to live out of a single roller bag and a backpack for over a week, so I guess that’s something.  A few months after I left my phone rings and it’s one of my old managers “Hey man, how are you doing?  feeling relaxed? done fucking around? ready to come home yet?”  They were firing up another team in Toronto and they wanted me to come home.  At first I wasn’t too keen on the idea, but I also didn’t want to say no and burn a bridge.  The West has also always been my home, Was born in Alberta and spent the bulk of my life in British Columbia.  But they made me an offer than I could not say no to and so I threw my most special things into a U-Haul trailer, strapped it onto my Volvo station wagon and hitched wagons east for Toronto.  That adventure will have it’s own post eventually, it was kind of epic so yeah stay tuned for that.

So now I’m in Toronto, the east is a little different from the west in ways I don’t really know how to explain yet.   I uprooted my world for this company but was feeling pretty good about coming back, the manager who convinced me things were better did a good job selling me.  He quit not long after I came back and that’s when we started falling down the rabbit hole. In the year that I was back I had 4 different managers, one of them definitely gets an award for being the single most awful manager I’ve ever had to endure, two of them quit to pursue better jobs.  Excluding the black sheep they were awesome dudes and I would work for 3 of them again any day and I kind of do work with one of them again because we landed at the same company :) That year of being back was crazy, there was a lot of buzz about us in the tech rags, we were ramping up for an IPO and many pundits were calling for our demise like those cats who wore sandwich boards with “the end is near” asking people if they had time to talk about jesus.

In a startup everyone puts up with the abuse because we are all issued stock options when we sign up.  Depending on how early you get in denotes how many options you get.  But that’s the name of the game when its comes to startups, high risk, high reward.  The pay day comes when the startup puts on its big boy pants and launches its Initial Public Offering.  This was the promise we were all given, stick it out and we will be rewarded for our loyalty.  All the years I was at the company that was part of what excited people, how awesome it will be when we finally IPO.  The IPO was a shit show to put it mildly, actually it was downright embarrassing.  We didn’t end up raising enough money and this was worrisome because we only had so much runway left and the IPO was going to guarantee that the company could survive until we became profitable and self sustaining.  We should have looked towards those kooks that believe in perpetual motion machines to see what our future held.  Much like a perpetual motion machine we were doomed to fail because of a series of missteps from management and market climate.  But there was a beacon of hope, Tom Barton.

To say that Ken Klein, the CEO who took Tintri public is an asshat would be one of the kinder things you could say about him.  The board should have ejected him and several other senior people years prior and maybe the company wouldn’t be on the bankruptcy auction block this week (if you have a few million kicking around, it’s a great fixer upper with solid bones).  After the anticlimax of our IPO the board finally turfed Ken and the hunt for a new leader began.  This is where Tom enters the scene, now this guy, he is the guy we needed at the helm from the start.  If someone with the leadership qualities he possessed was running the ship before it became a massive shitpocolypse, well then maybe things would be different.  I feel bad for Tom, he is an awesome leader who was sold a bunk sale of goods.  He started with us in April and thought he was coming into a company that had just enough money to last till we became profitable, the product was selling, customers loved and still do love the product immensely, things looked promising.  We all thought, with this new leader we were going to make it.

Part way through May we were all told that the company had only enough money to last till the end of June and likely wouldn’t make it very far into July.  This was akin to a kick in the jewels and lead to some feelings of panic.  If I lost this job, well my life as I knew it would change dramatically and not for the positive.  Thank goodness we had Tom, he gave us the bitter pill, but he was honest with us about it.  He set up a weekly call to bring us into what was happening so we would know, instead of wonder and then panic.  It was bad, there was no way to spin it really but it wasn’t over.  He was working hard to find a way to save the company, to save the jobs, to protect as many people and their families as he could.  He fought hard and I respect him immensely for it.  Around this same time I received a message from a competitor.  I met with him and liked what I heard so we talked some more.

I was torn because I loved the Tintri VMstore, it is an amazing product built by brilliant people that should have been more successful than it was but because of management missteps could be nothing more than another could have should have story, a case study in what not to do.  But I was also being courted by another company who had a really great story and had something Tintri didn’t, stability.  As much as I would have liked to stay for love we live in a capitalist society that requires money for rent and food, my landlord is a cool dude but “hey man I don’t have rent but I really love my job so lets just hang in there.” would have likely landed me on the streets.  So I kept talking with this new company and they gave me an offer letter and for the second time I had to part ways with Tintri.  This time was even harder because there was a possibility that we were going to be saved, in just a couple of days we would know and here I am getting ready to quit.  I wanted to stay till the end be it awesome or bitter, but I couldn’t do it, I needed stability. 

The Tuesday after I tendered my resignation we found out that Tom had quit abruptly and with no explanation, I’m honestly surprised he stayed as long as he did.  I don’t think many other execs would have fought as hard as he did to fix a situation that he had no part in creating.  We also found out that bankruptcy was inevitable and people were going to lose jobs, fast.  I was relieved that I already found a new home, but I was sad for my colleagues, many with families where they were also the sole earner.  The greed of a few affected many people who were loyal to them through thick and thin.  What a ride, insanely great highs with depressing lows.  I appreciate every minute that I was allowed to spend there though and am honored that I was a Tintrian.

I was able to do some really awesome things during my time at Tintri.  I met really great customers across both coasts of Canada and helped out teammates with projects in the US and Australia.  I was able to speak at almost every VMUG in Canada which was so cool, along with various tech conferences across canada.  I was able to represent the company at VMworld, Microsoft Ignite, RedHat Summit and OpenStack summit which are massive tech conferences and it was incredible to be part of those events.  The best part were the people, our customers we’re amazing and I love so many of my teammates and we are still friends today.  I wish them all the best in where their paths lead to next and glad our paths crossed at Tintri (you can see some of them below).  Would I do a startup again? maybe, but I certainly don’t regret taking a chance on Tintri.  I hope the auction goes well this week and someone buys them for more than just the IP. I’m rooting for the scrappy VMstore because I still believe it’s the best storage made for virtualization so far.