From VC to IT: Blissfully's Origin Story

Alone in the dark

I’m in a coffin-sized closet, alone in the corner of a dusty basement, sweating and staring at a blinking BIOS terminal. I'm being asked to pick a number between 1 and 4, and I can no longer hear the deafening server-fans over the sound of my own heart. If I pick the wrong number, a client with 100 years of operational continuity is going to lose gigabytes of critical data, none of it backed up, go down in flames, and, rightly, take down my own fledgling operation with it.

Six months prior, I was flying first-class, hunting for hyper-growth companies run by intensely resourceful & charismatic founders. My aim: evaluating their odds of creating multi-hundred-million-dollar returns, and positioning our firm as the ideal investment partner.

But right now, I’m the only person in this basement, and the sole technical authority in an acute, high-stakes test, desperately trying to remember OS boot-sequence nuances from distant childhood memories, back when I used to dick around with operating system fundamentals to make DOOM run faster.

Welcome to the origin story of Blissfully.com

I can fault this basement-drama back to a single whiskey-fueled conversation with my co-founder.

Ariel and I had previously built a startup together; I moved on to pursue an opportunity VC, and he remained running our high-tech operation inside the larger tech company that had acquired us.

Our old startup, Boundless, consumed and integrated apps like our survival depended on it (and in many ways, it did!). But our acquiring company? Technical excellence just wasn’t in its “soul” - none of their core systems were integrated, passwords were shared all over, new tools like Slack were scoffed at, a large percentage of the laptop fleet was collecting dust awaiting software-repair, and they couldn’t manage to keep the wifi operational.

But the bit that made Ariel the most salty? They didn’t seem to care.

I listened to his exasperations frequently, and the absurdity could only be absorbed along with lowball glass of sixteen-year aged Glenlivet. “What is wrong with that IT manager?”

Sadly, that one-man IT team was deep under-water - and he would never see the surface again. The organization was managing their technical operations like it was 1999, and swimming in technical debt. Debt created, ironically, by the absence of time spent investing in technology.

But it wasn't 1999, it was 2016 - and Ariel and I needed to know: “What's great IT in the age of SaaS?”

Our experience has shown us that smart IT teams evolve to embrace the cloud, providing their colleagues leverage and flexibility, as well themselves. Those that don’t either trade control for anarchy, or strangle an organization’s ability to stay competitive. With such fundamentally different outcomes at stake, we smelled opportunity.

“We should become the cloud-forward IT partner we would've wanted.”

From zero to Blissfully 1.0

We incorporated as a two-person Managed Service Provider, helping companies leverage cloud apps in ways they'd never dreamed, and bootstrapped up new ventures into  “cloud native” operations day 1.

That's how I found myself 10 feet below the surface of the earth with an entire business worth of data at risk. I was moving a venerable organization off a single rack-mount server (where backups hadn’t run successfully in years) and into the world of cloud storage. A critical reboot had reset the RAID controller back to factory defaults, and a wrong re-configuration would wipe critical partition information along with gigabytes of business data.

Caffeine, adrenaline, and my experience playing DOS games somehow came together in time to guide my selection, and Blissfully 1.0 succeeded at not destroying our first customer’s business. (Option #1, RAID level 0)

But the most important outcome of the crucible as an early MSP was gaining a deeper appreciation and empathy for IT professionals: this is hard, high-stakes work.

We slowly accumulated more scarring/learnings and began expanding our fledgling operation, subcontracting smart friends, building our toolbox of IT software, and more deeply understanding the challenges prospects and customers faced.

Interestingly, the most common speed-bump to evaluating a prospect’s technical setup was the same the same challenge we had to overcome when initially wrangling a new customers environment: no one had any idea what their IT and app infrastructure was!

Ariel and I are company builders, so we had experienced this ourselves. Yet the universality of this issue and the depth to which it prevented operational excellence was eye-opening.

Being able to quickly answer “what is this organization's actual relationship to technology?” would be key to unlocking new business and better serving the business we had.

So naturally, we fired up our code editors.

One month later we had a working prototype: we could detect several apps, including users and spend. Three months later, we could detect hundreds of apps, installation took less than 10 clicks, and reports were ready in 60 seconds. The following month, we had 50 organizations in our closed beta.

After our first year, our service business had evolved into a software company, and Blissfully 1.0 was born. We were learning at an incredible clip, and it was clear that:

• The opportunity was larger than we had originally assumed.
• We’d need a team and investment immediately.

Fortunately we had relationships with smart investors & technologists, and rapidly assembled an all-star team to get to the next level.

Welcome to Blissfully 2.0

We spent the next two years working with IT, Finance, and Ops to answer the fundamental question "what apps does my org use, and how secure/compliant/valuable are they?"

We've learned that most operational challenges can't be solved if you don't know where you are and where you're going. Specifically,

• How can you productively and completely onboard a new employee if you don’t know the tools they'll need and when they finally have access to them?
• How can you swiftly and securely off-board someone if you don’t know all the apps they accumulated during their tenure?
• How do you identify waste when ownership and utilization are diffuse and un-mapped?
• How can you properly adopt new vendors if you don’t understand how it overlaps or even replaces your choices?
• How can you responsibly approach contract renewals if you don’t know how well your teams are utilizing that vendor?
• How do you gracefully terminate vendors if you don’t who will be impacted and if alternatives are ready to go?
• How can you assess your compliance-posture if you don’t know your inventory of tools, let alone the thousands of distinct relationships users have with them?

And on and on and on...

We call this complicated network of people using apps the “SaaS graph”, and for most organizations, it’s largely unknown, and constantly changing, making operational excellence a pipe dream.

Blissfully does two simple things:

• We uncover the SaaS graph, keeping it automatically and continuously organized.
• We provide powerful workflows to productively and consistently respond to the constant change.

SaaS management may be IT’s responsibility, but SaaS leverage is everyone's opportunity- and Blissfully is built to let organizations fully realize it.

Welcome to a modern operating platform for IT.

We can’t wait to show you what we’ve built, where we’re going, and get there together.