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.

From VC, to IT. Blissfully’s Origin Story was originally published in Blissfully on Medium, where people are continuing the conversation by highlighting and responding to this story.

Your engineers battle big-baddies daily — but are they as effective as MMO players in achieving a swift burn-down of their foes?

World of Warcraft is impressive for its entertainment value, its cartoonish beauty, and the strength of its addictive pull. From a game design perspective, however, especially remarkable is the peerless execution of setting up complex boss battles, and total refinement of the role-based “Trinity” mechanic players must master to win.

As it happens, constructing software benefits from mastering the same mechanic, but most teams don’t know that they’re playing a similar game.

So before your team ventures out next, let me share the fundamental Trinity strategy of the MMO pros, and how to deploy it for efficient teamwork.

The MMO Holy Trinity of Team Roles

For the uninitiated, boss battles in MMOs require team coordination through specialization. The smallest team that could succeed is composed of a Damage Dealer, a Tank, and a Healer. This configuration is known the “MMO Holy Trinity.”

The Damage Dealer ⚔️️

Crouched to the side of the big-bad’s peripheral vision, a rogue issues a scimitar flurry of rending slashes, while at longer range, a wizard shoots potent fireballs — the sort of attacks that given just enough time can slaughter the most frightening of fiends.

These are the Damage Dealers ⚔️️

They train in combat exclusively focused on tearing flesh from bone, and waste no energy concerning themselves with defense. Instead, they measure their success with a single KPI: sustained DPS (damage per second). But these myopic, glass-cannons cannot do what they were born to do without protection.

The Tank 🛡️

It takes a uniquely bold hero to advance upon a gargantuan-horror, stare that certain death in the face… and taunt it.

Positioned in front of the enemy, armor shining, teeth grit, she gains the beast’s singular attention and readies herself to take a beating.

This brave character is the Tank 🛡️

Though she may opportunistically strike with her sword, the Tank’s specific duty is to draw the full ire of the beastie, soaking up as much damage, and surviving for as long as possible, so that her teammates can focus & specialize in something other than being a human lightning rod.

But dragon-kind are hardier than hominids, and even the most robust knight can’t last forever without support, and so she relies on the grace of others.

The Healer 🙌

The pairing between Damage Dealers and Tanks works wonders as long as the Tank can stay alive, but what could that team accomplish if someone could channel divine favor into unnaturally extended battlefield endurance?

The priest, the cleric, the druid of the group, these are the characters who transmute virtue into the hard currency of hit-points that Tanks need to survive, prolonging the distraction gambit while the Damage Dealers focus fire.

And even when battle plans invariably go sideways, these spiritual characters can save a vulnerable Damage Dealer from an unexpected sneak attack.

These supporters are known as Healers 🙌, and they form the final pillar of this deadly trinity.

This triad is the “minimally viable team” of the modern MMO, and together, there is no challenge they can’t overcome — and the same can be true of your engineers if analogously coordinated.

From the Dungeon to Your Office

While you likely don’t have building-sized dragons attacking your colleagues, your team is still playing a sort of engineering boss-battle, except that your “big bad” is a complex bundle of work, fought in hand to hand combat every day (and occasionally beyond).

If you have yet to organize your developer efforts in the same way you’d structure your raiding party, you’re missing out. Let’s fix that!

Role Call

First, understand that no one person can down the work-beast alone, and the foolhardy that try meet an inglorious end of burnout, and failure. This is a team effort, requiring the buy-in and support of every member.

At the beginning of the week, or once daily if you prefer, convene and lay bare the work to be done in front of your team, sizing up your enemy. Then, elect at least one Damage Dealer, one Tank, and one Healer from the group (of course, you can have more than one of each, but you must have at least one of each. We’ll return to this).

Your Damage Dealers ⚔️️ are given the scariest (important, but not necessarily urgent) parts of the monster (workload), and focus-fire it into oblivion. That’s it, that’s all they do. They work on the important. Once the “battle” begins, Damage Dealers gain adrenaline-induced tunnel vision until they destroy their target. Building product is hard, and the most important work is often the most subtle. It benefits from quiet, single-minded, uninterrupted attention. You must elect your Damage Dealers and imbue them with the “social right of refusal” to empower & protect them so that instead of delivering incremental improvements, they are unlocking meaningful new value for your customers. Don’t call Damage Dealers, they’ll call you. Seriously. You’ll know your Damage Dealers are operating correctly when no one hears from them for hours at a time. This is how work gets done.

In order to survive uninterrupted, Damage Dealers need the foundation of a solid ️Tank 🛡️️. The Tank’s responsibility is walking right up to the writhing mess of incoming requests & requirements, and staring them into submission. Every bit of existing work is “pulled” (taunted) by the Tank, as well as any incoming bit of new work (an ‘add’ in MMO parlance). The Tank is responsible for shielding others from all distractions, old and new. If somehow a monster/task/request creeps up (Slack message, email) and interrupts their firestorm, the Damage Dealer asks the Tank to step in. The Tank can nibble at the work themselves, of course, but their priority isn’t sword-swinging. Their priority is defending the team from the world so that others can specialize and deliver. Your Tank should let the broader organization know that they are the protector of the team’s scarcest resources (time & attention) and all requests should come through them first. Thus, their work includes coordinating development priorities, resource gathering, bug triage or detective work, taking on some of the support burdens, and being available both internally and externally (If you’re familiar with Agile, the Tank is analogous to Scrum Master).

But Tanks cannot last long when the broader organization sees them as stone-wallers delivering slowly and infrequently, even if the output is good. Occasionally the system needs slack to allow urgent work to happen immediately, without sacrificing a Damage Dealer’s intense focus to pay for that context switch.

Enabling this slack-in-the-system, we have the Healer 🙌. The Healer keeps the Tank from collapsing under the mounting burden of urgent work someone must do and simultaneously keeps Damage Dealers focused & alive by dealing with any adds (distractions). In practice, this means Healers work closely with Tanks to handle tasks on a more real-time, responsive basis. What happens when management throws a critical monkey wrench at your team? You have the Tank hand it off to a Healer, keeping your tunnel-visioned Damage Dealers protected, without missing a beat in the eyes of the broader organization. Secondarily, Healers themselves are direct resources for Damage Dealers who may need help when unexpected or tangential-but-critical work arises. Is there a bug in an unrelated part of the codebase blocking your Damage Dealer? Bring in the Healer! It’s fair game to interrupt them because Healers exist to provide the system with flexibility, handling important, or just plainly urgent forms of work. Frequently, this means bug-fixes, shorter incremental work, and technical customer support. All of which are important, and because those forms of work lend themselves to shorter time-chunking and rapid reprioritization, it’s best left for the folks wearing this support-oriented mantle.

In Practice

No one should be married to the last role they happened to choose, in fact, it’s appropriate for them to ‘re-spec’ weekly or even daily, provided the team has one member of each type. Some days you’re focused and ready to do high DPS, other days you may want to play a support role, and sometimes you’d prefer to coordinate a given project. Is your team larger than three people? Great, double up on roles! Your north-star is arranging your team to do the most DPS (damage per second) by having the maximum number of Damage Dealers you can, with the minimum necessary Tanks and Healers to support & protect them. Maximizing quiet time spent on meaningful work is how you effectively accomplish big things.

Two more practical pieces of advice. First, share this article with your team and those that would seek to interrupt them (Yes, I’ll be personally flattered, but moreover others should know what you’re up to and why). Build the language and understanding of these various roles.

Second, if you use Slack, have your team explicitly set their status-emoji to their current role: 🛡️, ⚔️️, or 🙌. Actively work to reinforce the social norms of how this system works. The outside world goes through the Tank when it needs something. The Damage Dealers are left entirely alone to focus, seeking others only when they themselves need aid. Healers keep the system greased, dealing with urgent and incremental forms of work, and helping un-stick Damage Dealers in times of need.

Happy Hunting.

PS: Damage Dealers may also use ☄️ because wizards are super cool.

PPS: We are Blissfully.com, a high-powered team slinging some fascinating technology to improve a product our customers love, and, we are hiring. We’re remote friendly, but it makes the board gaming a bit tougher. We’d love to hear from you.

In fact, our data shows that the rate of paid-SaaS adoption has been doubling year over year. That means a lot of software, a lot of expenses, and a lot of complexity. A perfect storm for expensive mistakes.

Before adopting Blissfully, we hear operators wonder:

• Are we wasting money?
• Are we using the right tools?
• Are these tools secure?
• What kind of access do tools have to our data?
• Are we at risk of inefficiencies, or worse?”

While you try and focus on growing your business, there’s a brewing chaos distracting your team from activities that uniquely make your business.

Blissfully exists to grant total awareness of what is going, then restore control to you, and finally, outright manage the distractions on your behalf.

How do we calm the chaos?

Our product, Blissfully Aware, uncovers all paid and free SaaS products adopted throughout your company — automatically. From a variety of data sources, we triangulate your full inventory of vendors and your detailed relationships to them. We deliver this in under a few minutes and keep it up to date forever.

We think this fundamental understanding of your vendor dependencies, known and unknown, financial and technical, is a basic building block for a well-oiled company.

We provide this awareness for free.

What you get

After installing our G Suite app, you’ll have a detailed view of all your SaaS subscriptions: all of your vendors, their billing contacts, how often & how much they bill, and specifically what they are billing for, including plan names and access to historical invoices.

We deliver reports breaking down how each department’s spend is trending, and which individuals are responsible for the most spend.

We also provide the easiest way to see how your company’s data is made available to the cloud. You’ll see which apps are granted important permissions, who granted those permissions, when they granted those permissions, and how many people rely on those tools (some of which you might be learning about for the first time!)

Lastly, we package up all these findings as a set of ready-to-consume insights, delivered in-app or to your inbox, helping you stay on top of new internal product adoptions, big swings in spend, possible security risks, and opportunities to eliminate waste.

The doors are open

We’ve been delivering on this vision to hundreds of companies that joined our Early Access Program, helping make sense of their tens-of-thousands of employees, and their complicated relationships to the cloud.

Today, we’re excited to open the doors for everyone. Interested? We’d love to help you, too. Sign up for free.

Originally published at www.blissfully.com on September 18, 2017.

Blissfully Launches out of Early Access was originally published in Blissfully on Medium, where people are continuing the conversation by highlighting and responding to this story.

Return co-founder Ariel Diaz & I uncovered an opportunity, raised a round from superlative investors (juicy details below), assembled the team, and built a product. So, what’s the thing?

The whole of modern work is moving to the cloud, moving to thousands of individual apps & services forming different nodes in the great internet-brain that lets us do that work better, faster, and with less frustration.

This is the era of SaaS.

Now, every individual in your organization is a decision maker, from how they do their job, and to an increasing extent, the tools they choose to do it. The consumerization of IT is not just phones & laptop; it’s individuals discovering, adopting, and leveraging best-of-breed tools marketed to them, their department, their niche, and even themselves.

This is fantastic! Yes!

This has elements of fresh hell! Also yes!

Trading the integrated cathedral of traditional IT, for the bottoms-up bazaar of loosely-coupled SaaS, brings a whole new set of concerns:

• With more software than ever before, do we know all our options?
• When evaluating those, do we have the necessary insight?
• With so many of those vendors continually adopted into our org, do we know what we depend upon?
• Are we integrating those products smartly? At all?
• And, how well are we managing this new complexity?

As if we didn’t have enough things to track & sift through instead of doing what we should be doing.

This trend isn’t abating, it’s accelerating, and that got us thinking. Could we automate the mundane, humanize the complex, and proactively deliver insight?

We think so; therefore we built Blissfully.com

Blissfully installs in under a minute, immediately showing you all the SaaS products your company uses, pays for, and stores data in.

First, Blissfully provides awareness (and a pun, all good companies involve puns, amirite Stewart Butterfield?)

In the minute after installation, you won’t be worrying about the big picture. It’s there for you, keeping itself up to date, forever. Here’s what you’re using, what you’re paying, and this is who’s involved. Sorted.

Now that manual vendor tracking is out of the way, let the automation begin!

Are you wasting money on tools for employees who are no longer even there? Have too many relationships with the same vendor? Could save money by changing plans? Need intel on negotiating better? Wish invoice receipts were “magnetized” to a single place? Need help understanding what all these vendors are? Tada! We’ve got all that.

And what about your company’s data exposure all over the web? Blissfully helps aggregate & navigate, proactively pushing critical information to the right people when the need arises. Blissfully strives to be reserved, self-assuredly, proactively-helpful.

Because our big-big-vision is simple: If you had someone who knew your organization’s tooling inside & out, knew all the products in the world inside & out, and proactively helped people throughout your org do even better, that’d be pretty special.

That’s what we’re doing — we’re building & automating that kind of insight & intelligence.

Our hands are full, we’ve got lots to do, and we find this so, so exciting. I hope you find it exciting, too. And if you do, Blissfully accepts applications to join our early access: http://www.blissfully.com

Great Vision, Aaron [thanks!]. How ‘Bout That Team?

I’m thrilled to be building Blissfully with incredibly smart, hard working people.

First, my co-founder Ariel Diaz, with whom I started Boundless.com years ago. We’ve grayed (read: learned) more, collected fresh chips on our shoulders, and working to make fetch a thing, come hell or high water.

Second, our early development team is fantastically capable.

Third, we’ve assembled a who’s who of high-energy, high-acumen founder-investors & founder-angels.

Eric Paley, partner Founder Collective, returns to work with Ariel & me for a second time around, leading the round. I wouldn’t “board-room” without him.

And we’re lucky to have assembled a group of angels that would make any dinner party truly stellar:

• Scott Belsky, founder Prefer, Behance
• Dharmesh Shah, CTO Hubspot
• tjmahony, venture partner Accomplice, founder FlipKey
• Mike Volpe & Yoav Shapira of Operator.vc
• Jace Cooke, founder Giphy
• Dave Balter, founder Mylestone, Smarterer, BzzAgent
• Wayne Chang & Jeff Seibert, founders Crashlytics
• Lars Albright & Scott Weller, founders of SessionM
• Drew Volpe, founder Procyon Ventures, Locately
• Andrew Rollins, founder Localytics, Sigma Prime
• Oisin Hanrahan & Umang Dua, founders Handy
• James Tamplin, founder Firebase
• Michael Sheeley, founder RunKeeper
• Dan Reich, founder Troops.ai
• Clark Valberg & Ryan Burke, CEO, VP Sales, Invision
• Philip H. Beauregard, founder OBJL, ReKindle
• Norm Rohr, VP Global Ops/Strategy, Pixability
• Jim Moskun & Frank Grossman, founders NuMega, Mindreef

Collectively, we catalyzed for Blissfully’s $1.5MM seed round, to earnestly begin building. We’re head-quartered in NYC, with an office in BOS.

We’re ready to rock, and we’ve got lots to do.

(And we’re looking for those who want to help us do it)

Wrangling SaaS, Blissfully was originally published in Blissfully on Medium, where people are continuing the conversation by highlighting and responding to this story.

What I learned from my sudden deep-dive into the world of mindfulness is that the point of such meditation is training your brain so you can “observe & respond rather than react,” and if you take some quiet time to simply observe what your mind is spontaneously concerning itself with, you’ll realize the vast majority is unhelpful non-sense — memes arising and falling from the white-noise of your wet-ware consciousness.

Even more disconcerting than just observing the content & frequency of the memetic noise, is realizing how much of your day to day choices and reactions are driven by those happenstance thoughts, and un-critically conditioned habits. That you, this mighty, autonomous, sovereign intellect you are… has so many of his life’s choices dictated by things arising from noise.

Oof, humbling.

As an arm-chair neuroscientist, this seems like a “System 1 vs System 2”* battle for your intentions. Do you allow noise & System 1 lizard-instincts to influence and dictate your choices, or can you slow down just enough to shift some greater percentage of your day into System 2 thinking and deliberate planning? And if you could, how much would that positively compound over the years?

Our lack of a consistently applied System 2 is most apparent when we over-indulge — the supporting battlecry from our inner & outer demons being “live a little!” and “that’s what makes us human!” Surprise, turns out System 2, enabled by our recently evolved neocortex, separating us from mostly instinct-driven animals, is actually what makes us human.

My favorite piece of advice which fits neatly, is from Stephen Covey: “begin with the end in mind”*. I use it as a quick hack for stopping in the moment, asking “what is it I’m actually after?,” forcing myself to slow down, and engage System 2’s planning capabilities a little more deliberately. Mindfulness in action. The more I practice meditation, the more of those opportunities I create for myself.

And sometimes a blog post.

Great reads & resources:

• Mindfulness Meditation by 10% Happier [iOS app]
• Thinking Fast & Slow [Book on System 1 & System 2 thinking]
• The 7 Habits of Highly Effective People [Of course you’ve read this ...right?]
• My thoughts on our “Monsters from the Id” [Blog post]

Finally, I’m an ardent atheist (in particular, because it rhymes) so when meditation or any self-help steers toward the spiritual, I rapidly eject. Thankfully, there are increasingly many secular resources & supporting science, so if you share the same aversions I do, fear not.

I spent the majority of this summer traveling & re-focusing on my health, and was curious what my weight’s trend-line looked like, so I dug it up. With a tiny bit of annotation, what’s most obvious is this: my work’s impact on me isn’t limited to just my mental health, stress impacts my body in a very real and directly measurable way.

The un-annotated & green areas are periods of unstructured travel & consulting, experimenting with new sports. The red areas are periods of consistent weight-gain, and happen to coincide directly with periods of intense work-focus. (One spike of note: my startup, Boundless, was sued in March of 2012, and you can see the outsized-effect it had on my weight)

Interestingly, I’ve intuitively described the difference in stress between entrepreneuriship and venture investing as follows: “Startups are extreme in their highs, but as extreme in their lows. Venture investing operates over a subtle background of more-constant stress.” Looks like the data supports that articulation.

There is of course debate as to whether sustained stress causes weight gain, or merely changes in stress. Whatever the ‘norm’ may be, my data is clear: work = weight gain. (I am fortunate, however, that my fluctuating weight is within relatively tight bounds)

Seeing my own data is a powerful insight & a clear reminder: if we aren’t actively investing in our success (work, life, friendship, etc), by default we are falling behind.

If you prefer, you can watch this presentation as I delivered it at the Shift Split conference.

The Power of Stories

As a child I believed logical arguments were enough to convince anyone of anything. You just needed enough time to explain them in painstaking, rational detail, and others would listen and understand.

As an adult, I know the world operates on story first, and logic second. The truth only matters for good stories, and most people don’t know how to tell good stories.

The difference in story-telling ability is massive; a poorly told story might bore the dinner table, a well-told story starts wars, create nations, and (one day!) colonizes mars. Behold the power of words: you make a bunch of sounds or symbols, and someone else reprioritizes their time & energy… woah.

The story of your company is a major, major piece of what “it” is, throughout its entire life — in fact, it’s the only thing “it” is in the very beginning, and that story, that “it”, is how you recruit employees, convince customers to give you a shot, and secure funding. Investors & smart hires will always do appropriate diligence before investing money & time, but they won’t bother doing that any diligience at all unless they are excited about your story. You can’t hand people a dry plan and expect them to “grok” the genius of your opportunity the same way you do. Generating excitement in others solely rests on you and the power of your story.

So this post is about story telling, and specifically about the 4 types of stories you’ll need to be able to tell well when fundraising for your company- but all of them are useful for recruiting, internal alignment, business development, and beyond. The pen (keyboard? thumb? Siri?) is mightier than the sword, so don’t neglect the narrative.

Let’s take a seat, it’s story time.

Helen Keller & The Hero’s Journey

When Helen Keller was only a year-and-a-half old, illness left her blind & deaf, and her prospects for communication looked grim. Six years later, in 1886, her parents found & called upon Anne Sullivan, an experienced teacher of the blind, to help a 7-year old Helen learn to communicate in terms of names and letters. Teaching Helen was immensely challenging, and when it seemed like she might never learn, Anne spelled “water” on Helen’s hand while running it under cool water. In that moment, language and naming ‘clicked’ for Helen.

18 years later, Helen graduated from Radcliffe (now a part of Harvard) as the first deaf/blind person with a Bachelor of Arts. She became a prolific writer (12 books, while you & I struggle with 1 email or 1 blog post!) She became a lecturer. She was a political activist fighting for those with disabilities, for women’s suffrage, for birth-control, for peace.

Helen Keller was a hero.

In fact, her life follows the “Hero’s Journey” wonderfully, and if you’re not familiar with the concept, you can see the arc here:

At its core, the Hero’s Journey is about venturing from the known into the unknown, and with a bit of help & digging deep, learning something critical to conquer your challenge, and then sharing that revelation with world for broader transformation.

Who better to advocate for the capability of the disabled than Helen Keller, who not only triumphed & demonstrated communication-competency, but mastery of communication in all its forms?

Being told factually that blind/deaf individuals are capable of writing & lecturing isn’t nearly as powerful and moving as the Hero’s Journey of Helen Keller. In the same way, you and your startup are your own “Hero’s Journey” and are much more compelling when framed in that narrative. Investors are looking for the “why you?” “what makes you so special?” “what hard-fought secret have you learned?” — don’t share the insight, tell the story.

Exempli gratia: Slack.

Stuart Butterfield had a vision for a non-violent MMO, and founded Tiny Speck to bring that vision to life. Team assembled, they set to work building tools, and building the game. Years later, they enthusiastically released their baby, “Glitch”, to the world, and though the game earned some following, it wasn’t enough. Tiny Speck decided to sunset Glitch and began winding down its operations. However, in a great moment of insight, Stuart & team realized the chat platform they had developed to support more productive game-development was a product that could help any team be more productive. Thus, Slack was born in the companies darkest hour, and now Slack’s team is bringing a new platform for team productivity to the world.

Interestingly, Stuart’s previous project Flickr was born from a previous failure at making the game. The poor guy just wants to make games and keeps accidentally changing the way the world communicates. A nice account of Stuart’s story is here.

The Kudzu & Disruption

Evolution is a fascinating thing to study. Understanding that species not only evolve against their environment, but how their environment co-evolves simultaneously against them, I find intriguing. Did the humming bird’s beak evolve & lengthen to get at a long-flowered plant’s nectar, or did some plant have the opportunity to evolve in length in order to keep pollinating-inefficient bees out, because a primordial humming-bird was there to provide a substitute?

When you look at a biological ecosystem, the creatures in it have spent thousands & thousands of years co-evolving against one another in a careful dance. The same metaphor is true for modern, ‘legacy’ businesses — most businesses that exist today have co-evolved against one another in a careful dance of suppliers, distributors, competitors, and partners.

Enter the Kudzu.

Co-evolution in an ecosystem is a beautiful and importantly a relatively stable thing. But what happens when you transplant an organism from one ecosystem into another? Three things:

• Likely, it will be brutally selected against (i.e.: die)
• Occasionally it will find a niche & join the careful co-evolution dance.
• But sometimes… sometimes it DOMINATES the ecosystem and changes the waltz to a salsa.

This is an invasive species. It’s alien to the ecosystem, doesn’t know the dance-steps and doesn’t care, because none of the native-organisms had any chance to evolve meaningful defenses against it. It dances the salsa while flustered waltzers leave the ballroom floor (read: they die).

The Kudzu is a salsa-dancing plant, native to a colder salsa-dancing Chinese ecosystem. And while the Kudzu is naturally fast-growing (up to a foot a day), and can kill existing vegetation by growing right over it & shading it out, this isn’t a problem when the Chinese winter beats it back each year, keeping it in check relative to other plants it salsa-dances with.

Then, also in the 1880s, some clever American entrepreneurs decided to market a “fast growing, shade generating” plant to the overly warm citizens living the waltz-dancing climate of the south-eastern United States.

Flash forward 100 years: now listed as a noxious weed, the Kudzu is found as far north as NYC and Nova Scotia Canada, and covers 7.5 million acres of land.

The Kudzu, and other invasive species, are disruptive technologies — the ecosystem it was introduced into didn’t stand a chance against it, because they never had a chance to co-evolve against it- and so it runs rampant. In contrast to the heroism of Helen Keller, your startup’s story also needs to demonstrate its Kudzu-like invasiveness, how no incumbents are adapted, nor could any adapt fast enough. Are you aggregating & leveraging a competitive data-set none will be able to reproduce? Are you bringing an army of algorithm authors to attack a sleepy non-technical industry? Are you able to achieve pricing 10x better than incumbents due to unfair cost advantages? Etc, etc, etc. While stories of ‘disruption’ are numerous, real disruption stories look like invasive species stories.

My favorite recent disruption story is, somewhat predictably, Uber’s story. Uber was born from a simple desire, “why can’t I just use my phone to tap-summon a taxi?” and a brilliant insight: tap-summoning black-cars skirts the laws that prevent non-taxis from picking up people on the street. Since the tap-summon is a “pre-arrangement”, no laws have been broken.

So what happens when a singular silicon valley tech/UX/data-driven/mobile focused company invades a progress-sleepy/frustrating/dirty-money-driven/waving-into-the-air based taxi industry that is horribly fragmented not only nationally but per-city and could never recreate the experience or market liquidity of an aggregated (and far superior) offering from Uber? Well, the un-adapted /un-adaptable industry fights the only way they can (litigating) while the rest of us cheaply & happily zip from place to place, and the tech-Kudzu that is Uber is valued in the tens of billions.

Be the Kudzu.

Babe Ruth & The Called Shot

Babe Ruth is an American baseball player famous for his larger than life personality, and larger than life talent. He played for the New York Yankees between 1920 and 1934. In 1932, when the Yankees made it to the world series, and Babe Ruth stepped up to the plate as batter, he was met with lemon throwing and jeers from hostile fans. With two strikes (three and you’re out) Babe Ruth pointed straight down the field. The pitch was thrown, he swung the bat, and hit a home run exactly in the direction he had pointed, and that moment became famous as the “Babe Ruth called shot”.

The “Called Shot” is the epitome of execution- “this is what I’m going to do, watch me do it”, and the implied “I told you so”. Data can sometimes speak for itself, but when it’s part of a “called shot” story, it’s incredibly powerful. I’m not a sports guy by any stretch of the imagination, but here you & I are 80 years later reading/writing about someone who pointed his finger and swing a bat, that’s how emotionally impactful the called shot is — it burns a memory like little else.

Each financing you raise is to get to the next milestone, so when pitching your startup, some portion of your pitch should include a called shot.

“We are raising this seed to go do X”…. then go do X.

Because then when you go back to the same capital market for your Series A, and say “We are raising this A to do Y” you’ll have a lot of folks leaning in. Even if you didn’t pitch a particular investor for your previous round, if you contextualize your raise around “Seed was designed to do X, we did X, Series A is designed to do Y” you’re showcasing your foresight and execution powerfully.

This data & execution framing technique isn’t limited to financings. Trying to recruit a co-founder or key-employee? Regularly update them on your plan, expectations, and show that you’re a predictable knock-it-out-of-the-park machine.

“Our vision is to be the world’s most consumer-centric company, where customers can come to find anything they want to buy online.” — Jeff Bezos

David Copperfield & Framing the Theory

If I wanted to do something bold, something big, something impossible like making the Statue of Liberty disappear and televising it— what would have to happen for you to believe I did that? Well certainly:

• Not only would the TV cameras show it had disappeared, but
• They would film in long, un-cut arcs free of trickery,
• A credible live crowd would testify live at the truth of the spectacle,
• Search lights would pass right through where the statue used to stand,
• Helicopters circling with cameras would confirm the dissapearce from multiple perspectives,
• and even radar would confirm the loss of a giant metal structure.

David Copperfield proposed, and dramatically executed the disappearance (and re-appareance) of the Statue of Liberty in 1983 to a live audience on Liberty Island, and live audiences around the world. This was more than just a called shot, and far more than sleight of hand, this was story telling of the grandest kind.

If a magician can convince people of the truth of the impossible, what you should be able to do around probability of the plausible?

Ultimately, your startup is a hypothesis you’ll build into a theory. “Because of insights A/B/C, if we build D/E/F, we’ll grow fast in markets J/K/L, and you’ll know we’re on the right path because of metrics that look like X/Y/Z.” You need to clearly frame your core hypothesis, and you need to frame the metrics & indicators that would confirm its deeper truth.

The point isn’t to emulate the friendly deceitfulness of magicians like David Copperfield, but to appreciate how much care they take in guiding the audience to understand the depth of their illusion, how to judge its execution, and how to appreciate the experience. Define your startup’s hypothesis, help others see the best way to appreciate it, explain the metrics by which they should judge your execution, and let them appreciate the results you have to date.

Be authentic, be believable, and take charge of the framing.

Go Forth & Story Tell

Never burden your audience- you should be so lucky to get the attention of someone smart, let alone someone masochistic enough to dig-in on something they don’t find exciting. If they are worth talking to, their attention is already valued at a premium, and they have plenty of options.

Moreover, why should others invest time & money into a poorly told story? If the founder of a startup isn’t their own opportunity’s best story-teller, who could possibly come to understand it better than they? And in the rare case that the listener might appreciate the genius buried beneath a cloudy, uninspiring story- does that same smart listener expect the budy world of talent and would-be customers would have the same patience that they have?

Be a hero, be the kudzu, call the shot, and frame the theory. Above all else, tell a good story.

(Adapted from a presentation I gave at the awesome Shift Split conference)

Lurking behind our thin, rational facade is an impulsive demon. A demon that takes control of us, acts without thinking, and serves its own purposes regardless of the impact to our ultimate well-being.

That demon is your id.

Your id, your lizard-brain, your ‘animal’ impulses, that piece of you evolved in a context wildly different from the one in which you now live.

Our vast technology network, now held and ever-accessible in the palm of your hand, push-notifying for your attention wherever you go- that tech is the make-shift key that not only unlocks your inner-demon, but amplifies him & allows him to run your life unchecked & afoul.

This isn’t a new observation- it’s the central warning of 1956’s classic science-fiction film, “Forbidden Planet.” Explorers discover the remnants of an advanced alien civiliation (“the Krell”) & attempt to uncover its secrets while under attack from an invisible monster. The great reveal of the movie: the peaceful Krell created machinery so advanced it turned desire into matter. But even the most rational Krell were evolved from creatures less noble, and at the center of every Krell brain still hid a lizard-core, a place of base instinct… a place of pure id. The Krell’s machinery faithfully transformed even the darkest subcioncious impulse into a literal “monster from the id,” wiping one-another out. The explorers realize dramataically that the invisible monster they fight, is in fact themselves.

Someone dreamt that up in 1956 (kudos to you, writers!)

Back to 2015: Would you like cheap, gut-inflating chinese food delivered to where you stand… in under 5 seconds of tapping? Why not add libations delivered with equal ease? Slightly inebriated and upset: reach across space & time to speak (read: thumb-scribe) your mind to someone who has wronged you, regret for drunk-texting can wait until morning. Even then, you can console yourself by splurging thousands on luxury fashion, confirming the indulgent transaction by simply pressing your thumb over the small circle at the bottom of your phone, all financial hesitation set aside by easy credit. Never mind driving yourself deeper into debt, ignore it and satisfy the impulse to order the next plate of General Gao’s chicken instead.

Repeat.

The fundamental problem is that our well-meaning side is the slow-side of our mental machinery, while our impulsive animal side rapidly & frequently seizes on whatever it can, after it all, it evolved in a context of relative scarcity. Which is why we crave sweets & fats… because they were rarer historically. We consume such treats not in moderation but until they are gone, because that is what it used to take to survive. Over-supply was not a problem in the ancient world, but certainly a problem if you’re drunk-shopping at 7/11, or hungry-walking the aisles of Market Basket in 2015.

Information technology not only efficiently matches supply with demand in the palm of our hand, but increasingly jujitsus our minor vices (boredom, insecurity) into demand-generating opportunities. These desires, freshly heightened by rapidly evolving, data-driven marketing, can be satisfied instantly by equally scientifically developed products & funnels…. long before the rational mind can speak up and say “hey wait, woah there!”

Your mental machinery remains the same, meanwhile every product & marketing department the world ‘round is leveling up.

Worse still, the negative effects of id indulgement essentially compound: bad habits are more easily reinforced than good ones, quickly entrenched, and willpower erodes. The battle for self-control isn’t lost, but if we aren’t proactively fighting & improving, we should be aware we are actively losing by default.

I welcome technology that can keep up on the positive side of the arms-race, though by nature, the consumer markets (and thus capital ones) favor catering to the id. Therefore, the only remedy I’m aware of is to deliberately take control of your environment in greater measure than those who are paid to market directly to your id. Willpower itself is not the solution, we must erect automatic, high-friction walls to provide breathing room for our slower, rational-brains to work their magic, and automate proper decision making, removing as many opportunities for failure as we can.

The battle for control over our id will not easily be won back, and our collective well-being hangs on the outcome.

Addendum

Instead of waiting for the world to provide more productive tooling, I have tried employing various strategies to construct more id-barriers in my own life, a few of which are listed below:

Nutrition:

• Deleting all my “food delivery” accounts to prevent eating poorly.
• Owning neither a microwave or toaster, in effect forcing myself to eat fresher.
• Never stocking any unhealthy snacks at all, no exceptions.
• Pre-making healthy breakfasts on Sunday so I have no excuses during the week’s rushed mornings.
• Buying weeks worth of pre-made paleo dinners so during my lowest energy point of the day (evenings), the right decision is the by default the easiest/fastest.

Time/Energy Management:

• Not owning a TV to prevent time-wasting (or cable, or Netflix, etc)
• Uninstalling social media apps from my iPhone (no more Snapchat, Tumblr, Instagram, etc).
• Installing a Chrome extension to limit social-surfing to under 10 minutes per day.
• Checking email in batches.
• Daily meditation.
• Daily goal-setting w/ social accountabiltiy via a “goals group”.

Finances:

• Generally living as minimalist to keep financial & psychic ownership costs down.
• Fully automating my finances all the way down to a weekly allowance (that hard-bounces) to prevent wasteful shopping.
• Un-installing & deactivating on-demand/e-commerce *accounts* when consumption becomes subconscious or habitual.
• Favoring predictability/automation of purchases over price-optimization.

Recommended Reading:

• The Power of Habit
• Willpower
• Thinking Fast & Slow
• Marshmallow Test

For those also fighting their inner monster, I welcome your own suggestions & insights.

Shift Split just concluded its 4th annual conference last week, and I’m grateful & inspired to have been a part. I met with Shift’s founder, Ivan Burazin, while he was taking his company Codeanywhere through Techstars Boston. Following great conversation about startups, programming, and cloud trends, he invited me to speak at his conference. Excited as I was to accept, I had no idea what a home-town hero, hustler, and entrepreneur Ivan truly is. Shift began when Ivan returned from an Austrian conference wondering “why can’t we have one in Croatia?… why not?” After four years of doubling attendance, from all parts of the region and beyond, it’s amazing what a little vision can do.

But between startup pitches, speeches & beaches, sailing, wining, and dining, I ended up learning something more about time. Specifically:

Time well-spent is the time that moves wrong.

You’ve lost yourself in the “flow” of good work or great conversation and wonder where all the time went: time well-spent. When days feel as full as weeks, and you realize “that was only just yesterday!”, and time seems to have moved slower: time well-spent.

We know that habitual activity doesn’t register the same in our memory. You made that coffee, you dressed yourself, you commuted to work, but do you remember how specifically? Conciousness is perhaps a sort of shark, if it ceases to experience the novel, when life becomes habitual, it dies, or at least it goes into a sleep. Time passes, but nothing is noted. Days filled with empty-calorie, non-experiences.

After 6 days in Split, engaged in fascinating conversation, I write this wondering “where all that time went”. And even though I can distinctly remember the details & schedule of every day, I remember being baffled that I could have learned so much, experienced so much, met so many amazing people, “all in just this one day!” — time extremely well-spent.

This trip has reminded me viscerally that with time, you can’t control if it’s spent, yet you do control how. When deciding how to spend your days, make time move wrong.