In the Arena

The wave crashes.

Trashing you head first into the depths.

You gasp for air.  Water fills your lungs.  You’re drowning.

You flail.  You kick.  You fight.  You’re still drowning.

Light begins to fade to dark.

Darker, darker, darkness…

I once read that depression is like drowning – drowning while you watch everyone else swim.  All the while you think: Why can’t I swim like they can?  Why can’t I reach the surface?  Why me?

I can also attest: depression feels like drowning.  I know from first-hand experience.  I know from my own major depression.

Yesterday was a day of much personal reflection – as Bell launched it “Let’s Talk” campaign to change the dialogue around mental health.  To fundamentally shift our perceptions, to battle the “stigma”.  

Stigma was a word that I read over, and over, and over again.  It struck me not because of the “stigma” I’ve personally experienced, and now have a deep understanding of, but rather because it’s difficult for me to intellectualize “why?” there’s any stigma at all.

I’ve thought about this “why?” a lot…

What I’ve come to is this: somewhere in the evolution of Western medicine, the body was divided into separate parts. Physicians specialized in those parts: kidneys, hearts, lungs, ears, noses, throats, the list goes on. 

The brain was no exception.  Part of the brain went to neuroscience and neurology, part went to psychiatry and psychology.  The latter – put in a literal and figurative corner.  The corner for the crazy people.

For decades, maybe better described as centuries, the mind and body were split.  Physical health and mental health were two distinct entities, separated by physical, societal, and financial barriers.  

But here in lies the confusing bit: aren’t physical and mental health one-and-the-same?

The brain is a physical entity.  It is part of our body.  It is an organ.  And like every other organ, like every part of the body, it is not immune to injury. It is not immune to illness.  It is not immune to disease. 

So, why then, is there stigma toward those with brain injuries, diseases, and illnesses?  Do we have stigma towards those with kidney disease?  Heart disease?  Lung disease?  Of course not.  We intellectualize those as “body parts”, but on the other hand struggle to see the brain as a “body part”. 

This is why I reframe mental illness to an illness of the brain.  Not of the mind.  Not of the person.

I believe we have this stigma, this lack of understanding, because the brain, unlike any other organ, has a direct correlation with human behaviour.  With personality.  With the mind.

It’s often the inability of those suffering from these ailments – and those supporting these sufferers – to disconnect the illness from behaviour that causes such deep frustration, misunderstanding, and stigma.  It’s the crazy part.

When we reframe our thinking, we can fundamentally change how we approach “mental illness”.  We begin to see how the brain can get its version of a cold, that the brain can have permanent deficiencies or impairments, that external stress and internal chemicals can have a profound effect on what our brain does - in a moment and over a lifetime.

At its core, the human body is a complex system.  It is not Lego made up of distinct building blocks.  That complex system is controlled by the brain, it’s communication pathway the central nervous system.  It is our own version of an operating system, the O/S that regulates our entire body, the foundation for our consciousness.

So it should be no surprise that peoples’ thoughts, behaviours, and feelings can become impaired.  People can feel low, people can feel like they’re drowning, people can seem “crazy” (based on our perceptions of what’s “normal”). 

As we look to the next 363 days until Bell’s 2018 “Let’s Talk” campaign, I challenge you to reframe how you define mental health and mental illness.  Do not think of it as separate, as distinct from physical health and physical illness. Eliminate the stigma by thinking of the body as a system, with the brain as its central player, and appreciate that the brain is inherently vulnerable.  That’s what makes it – and us – human.  

Now - I’d like to close with one last thought: a thank you.

Thank you to my family, friends, colleagues, medical professionals, and countless strangers for throwing me a life line.  For giving me the space to re-learn how to swim.  For dragging me out of the depths.  Bringing me back to the surface.  

It is because of you that I lightly tread water, patiently waiting to ride the next wave.

#SickNotWeak

Almost 3 years ago (to the date) I wrote my first blog post on “In the Arena”.

There was very little rhyme and very little reason to starting this blog (beyond finding some outlet to express my thoughts in my last semester at HBS).  

And to be very open, I was unemployed and hoping that a few blog posts might make me stand out to whatever lucky (or very unfortunate) soul invited me to join their team full-time.

However, only a few days later I wrote a post titled “Why I’m writing” (evidence here).

In that post I talked about how writing can be a “phenomenal grounding exercise” and that as a person who is “not usually very present”, writing can be a “great remedy to pause and be in the moment”.  My good friend, James, might call that a “necessary prescription”.

I also reflected that writing would force me to “take stock” of what I called “those often fleeting aha moments of insight”.

Turns out, the 27 year-old version of me was able to read my 30 year-old mind.

Though the sentiment about “why I’m writing” might be the same, the content, perspectives, and life experiences are drastically different.

For the most part, the last 2 1/2 years have been a writing hiatus.  

The last 2 1/2 years have also been the most transformational, the most challenging, the most rewarding, the most depressing.  They have been cause for extreme introspection - as, in my view, that introspection was the only way out from what I’d describe as an existential crisis.

But through the fire, I feel changed, reborn.  I feel emboldened to continue to share my learnings - in the hope they resonate with at least someone.  And if they don’t, I’ll take solace in the fact that this is part of my necessary prescription.

With that context, I’ve changed the “what” not the “why” I’m writing.

When I started, I said I’d write about startups, the future, and business engineering - a term I clearly made up to describe the “building” business people like myself do in the context of a startup vs. vocationally trained engineers (who, yes, do most of the real building!).

The only thing I’ve kept constant is startups.

I live-and-breathe the startup world - whether that’s working at League or supporting young entrepreneurs here in Toronto.  And I believe that startup life, a life on the “frontier” of business, is still central to who I am - and where I can (fingers crossed) provide unique perspective.

But that’s the only constant.

I’ve added mental health as a theme.

I’ve added outlier philosophy as a theme.

And yes, I made up “outlier philosophy”.  I had to make up at least one of this blog’s themes...

Now, I won’t dive into “what” these themes really mean or “why” I’m compelled to write about them.  I’ll leave that task for the next 52 weeks.

Over this time, I will write 52 posts.  

I have no idea what they’ll be about.  I have no idea when I’ll post them.  But I do know that they will be my stream of consciousness.  They will be raw, unedited, unfiltered, and very real.  They will be the truest reflection of me.

I hope you’ll follow along...

Originally posted to Facebook on November 9, 2016 

Now that I've personally (and privately) got all my "what just happened?" and "is this the end of America?" comments - and worse - out, a good night sleep seems like cause for reflection.

What happened yesterday - to me - signals a very clear divide between those that feel that they are being left behind, that they are losing control and those that "have" or have some shred of promise. This is not necessarily a red vs. blue issue, though it played out that way yesterday. What I believe is central to yesterday's outcome is that the major transitions that are happening at a macro level - in the United States and globally - are redistributing wealth and redistributing control.

Those who are losing grip are looking for pragmatic solutions. They hope to no longer live in a "3rd world country" as the President Elect himself described in the first debate.

The sad truth though - is that the macro and micro are disconnected. The policies proposed by the President Elect might sound good in a tweet, but won't actually help these people tomorrow, a year from now, or ten years from now.

Repealing Obamacare will actually reduce healthcare coverage and shift more-and-more costs onto these Americans (given the significant subsidies that many of these people are receiving). Promoting protectionist economic policies - and reducing free trade - are not going to bring jobs back, in fact they will reduce the economic competitiveness of America - and give other countries the chance to "step up" (and trust me, they're just as hungry as you America!). Isolationist immigration policies might keep out a few "terrorists, criminals, and rapists", but they will increasingly detract the high-skilled workers that the future American economy desperately needs. Students - like a younger version of myself - studying at the some of the nation's top universities will look to their home countries or other regions for employment (i.e., saying a quick thanks for the diploma and taking their skills elsewhere).

This is my point - I feel bad for many of the people that are inspired by what the President Elect has promoted. They saw him as a way to "shake things up", but if they looked deeply at the proposed policies it would be clear that what might seem like "smart" ideas are taking America backward not forward.

But I also feel bad because of the hard truth that underlies this - that when there are winners, there are losers. There are many people who are "losing" and will keep "losing". This shift - particularly economically - is not necessarily slowing down and will cause developed nations to seriously consider policies like a "basic guaranteed income". Particularly when one of the world's most prominent companies, Uber, aspires to have no drivers. And Uber is 100% not joking.

I hope this moment, and the next four years, are cause for deep reflection among Americans - a reconsideration of American exceptionalism at its very foundation. A realization that every empire in history has fallen, and the fact that America (no matter how many world wars its "won" or how "great" it is) is not immune to stumbling itself. That there is ultimately more value in Americans uniting as one than continuing to fracture into pieces.

If I were to provide any solace to my American friends, it would be a reminder that not long ago, the "great" city of Toronto elected a crack-smoking, buffoon as Mayor. And not long after, he was out-of-office replaced by a highly intelligent, capable, compassionate person that is leading this city toward global prominence.

I wish the same for you, friends...

I’m feeling nostalgic.  Not surprisingly.

This is my last week at Harvard Business School.  I literally just walked out of my second last class.  Ever.  And I as I sit in the Harvard Innovation Lab, with my cursor blinking, I’m searching seemingly endlessly for a topic to write about in my last #digHBS blog post.

No matter how hard I try, I keep coming back to my nostalgia.  Instead of writing about the latest tech headline, I'm going to write about my experience at HBS.  Well, at least one dimension of my experience.

To step back, #digHBS taught me one lesson this semester: no one is safe from the digital revolution.

That’s the reality we’re staring in the face as we leave HBS for the 21st century economy.  As leaders, managers and entrepreneurs, we’ll have to deal with changing tides.  We’ll have to deal with “software eating the world”.  We’ll be (at one point or another) the disruptor and the disrupted.

This got me thinking: what was my “digital transformation”?

I had come here, nearly two years ago, as a "strategy consultant" turned “digital initiate”.  I had been on both sides of the coin: helping incumbents embrace a brave new digital world and building products to transform the old guard.  Though not an engineer by training, I felt like an engineer at heart.  And I was certain in my goal at HBS: to dive deeper into technology and entrepreneurship.

To say I was surprised would be an understatement.

I stumbled across a student body inspired by technology, passionate about what was (now) possible.  I was exposed to entrepreneurs, venture capitalists and technology leaders like no other place I had been.  And I dove in head first: trying to start two companies in RC year, failing both times, and getting “back in the startup saddle” in EC year… failing again.

If I was ever in doubt whether HBS was the “right” place for entrepreneurs, I had long forgotten.  This is a magical place for entrepreneurs and technologists alike.  There’s no question the experience will exponentially increase my probability of success when I take the plunge back into entrepreneurship.  Even though that dream is on pause (for now).

It was EC year, in particular, that added rocket fuel to my “digital transformation”.  The curriculum was the proverbial the nail in the coffin: a mix of hands-on experience, practical seminars like PM 102 and high-level strategy classes like #digHBS.  I now leave HBS a full-fledged “digital mercenary”.

But I must admit: HBS is not, by any means, done its own digital transformation.

The “business” world we live in today demands far different skills from the world 10, 20 or 30 years ago.  I’d argue that HBS’s curriculum today is still heavily skewed toward “how to think” and not “how to do”.  The latter is what companies, big and small, need more of today.  I don’t think it would be putting it lightly to say that “strategic frameworks” are a commodity, while understanding MySQL, Google AdWords and the technology stack are pure gold.

Though there is still a long way to go, HBS seems on the right track.  With the Digital Initiative, Rock Center, FIELD 3 and HBX, the school is positioning itself for another century at the forefront of business education.  No doubt, it will be a fascinating “transformation” to watch.

Do I follow my gut?  Or the data?

Every product manager (and entrepreneur) seems to struggle with this question.  And unfortunately, there is no hard-and-fast “right” answer about how to best design new products.  As a result, product managers often take an “it depends” approach, varying the balance between intuition and data situation-by-situation.

This raises more fundamental questions about product development.  When is data more reliable than intuition?  How does a data- or intuition-driven culture perform in the long term?  What approach leads to the most “successful”, “delightful” products?

Notwithstanding any empirical data (yes, a proverbial sin in HBS’s “Digital Innovation & Transformation” class), it’s instructive to consider a few examples of data- and intuition- driven product development.

Let’s take Google to start.

So the story goes, Marissa Mayer famously tested over 40 shades of blue to maximize click-through-rates.  This is but one example of the rigorously analytical culture Google is known for, which is hardly surprising given its engineering-centric ethos.  It also seems to fit with their product (at least search) where small percentage increases in key metrics drive millions of dollars in return.

Apple on the other hand was guided by Steve Job’s mantra that “It’s really hard to design products by focus groups… a lot of times, people don’t know what they want until you show it to them.”   This mantra was underscored by a perspective that Apple products are designed for what Apple employees wanted for themselves.  This also fits with their products: ones where it seems hard for consumers to truly articulate their needs, wants and preferences.

However, both approaches have their downfalls.  Google has been much maligned for having poorly designed, emotionless user experiences contrived from a “by the numbers” approach.  Whereas Apple has missed opportunities as a result of its wall-garden approach and has struggled to introduce a meaningful innovation since the iPad’s launch in 2010.

Neither of these examples solves our early questions, though.  That’s why I personally keep coming back to: “it depends”.

It depends what you’re trying to accomplish.  It depends what types of products you’re building.  It depends what fits with your existing culture.

Google highlighted an approach that can be wildly successful for incremental product improvements, especially for web-based products that can be rapidly tested in real-time.  Apple highlighted an approach that can be wildly successful for transformative, new-to-the-world products, especially where hardware and industrial design are critical elements.

Really, the major takeaway is that a balanced “data vs. intuition” product development culture should be built within your startup, company or organization.

In many ways, the New Zealand yachting team in the 1995 America’s Cup struck the perfect balance.  Their engineering team used complex data models to inform design decisions, but ultimately deferred to the “crew” on how yacht configurations “felt” in the water.  If the crew didn’t like a configuration, the engineering team never even looked at the data.

With all of that, I think there are three additional takeaways:

Always start product design from genuine insight: whether from observation or feedback

Create a product feedback-loop that integrates data, intuition and clear metrics

Make the tough call: it’s what the product manager is paid to do!

Healthcare is one of the most perplexing markets for entrepreneurs.  There are more problems to solve, with more urgency, than almost any other market.  However, innovation is often stifled by complex regulatory frameworks, misaligned incentives and an aversion to technology.  These problems are only exacerbated by long sales cycles, tight budgets and unclear purchasing authority.

This leaves many healthcare entrepreneurs, with sound product and service concepts, struggling to scale.  A seemingly endless set of sales channels (from clinics to hospitals to payers) puts these entrepreneurs at a high risk of muddling their target customers and users.

That brings us to Healo: a healthcare IT startup at Harvard Business School, with an initial focus on reducing in-person follow-ups for simple skin procedures.  

Healo is searching for “product-market fit” literally in real-time.  With a high-value, revolutionary technology, the founding team is rapidly iterating to find its “early adopter” sales channel.  From the outside looking in, Healo seemingly has a great problem: multiple routes to market, each with the potential to build a successful standalone business.  However, limited resources make solving the problem much more complex.

As part of “solving” this product-market fit problem, we decided to explore the opportunity to sell Healo’s product directly to home health agencies.  The following blog post outlines our journey by describing:

Why Home Health?

What We Did.

What We Learned.

Tips for Healthcare IT Entrepreneurs.

Why Home Health? To better set the context, Healo is a remote wound monitoring solution for patients and clinicians. Patients use their smartphone, plus Healo’s proprietary software, to monitor healing progress and take pictures of their wounds over time.  These pictures are then transmitted to a clinician for review. The end result: cost savings per episode, more consistent treatment, less in-clinic visits, and better patient outcomes. To start, Healo has been targeting surgical clinics whose entire patient populations require wound monitoring post-discharge (e.g., plastic surgery).  These clinics, like those at Boston Children’s Hospital and Massachusetts General Hospital, have expressed significant interest in Healo given the opportunity to reduce cost, while maintaining quality, within bundled payment structures.

Though an attractive opportunity (at least “on paper”), these clinics are often part of large, academic medical centers with stringent technology, compliance and legal policies.  This has led to long sales cycles that prevent Healo from demonstrating value and collecting clinical data.

This ultimately led the team to consider alternative, parallel routes to market.  At first glance, home health was a natural candidate (with $75+ billion in annual expenditures).

Healo could deliver real-time monitoring and cost containment for home health agencies whose patient populations have wound care needs, alongside other co-morbidities.  In addition, these are independent (often smaller) agencies that contracted with payers and providers to deliver in-home care.  As a result, the sales and implementation process could be much more streamlined.

This led us to develop three core hypotheses:

Healo solves a significant wound monitoring problem for a meaningful percentage of home health patients (>10%)

Healo needs to evolve its current product offering to include “in-home nurse” functionality across multiple assigned patients

Healo’s sales and implementation cycle (for a pilot) would be meaningfully shorter than that for clinics within academic medical centers

  What We Did

To begin exploring these hypotheses, we scheduled a 45-minute “pitch meeting” with the Home Care Alliance of Massachusetts’ (HCAMa) board of directors, which includes executive directors from 10 home health agencies.  

This “pitch meeting” would serve two purposes.  

First, it would act as a focus group for additional customer discovery.  This would allow us to test our 1st hypothesis on whether there is a meaningful opportunity for wound monitoring within home health.  Second, it would be our first sales call to these 10 agencies in the longer process of selling and implementing Healo’s beta product.  This would allow us to measure our “conversion rate” from initial pitch meeting to follow-up conversations with each agency.

In preparation, we sought to better understand the dynamics and needs of the home health market.  Through independent research, it became apparent that our 2nd hypothesis about home health was correct: we would need to reframe Healo’s value proposition and ultimately refocus the product around the visiting nurse.

As a result, we redesigned our pitch deck to highlight our nuanced understanding of the market and how the product would evolve to serve visiting nurses.  This included:

Visualizing a home care-specific workflow where visiting nurses check-in, transmit wound images and specialists review images through a centralized dashboard 

Articulating a future product vision that would include nurse schedules and tasks, Google Maps integration, productivity analytics and patient profiles 

Lastly, we drafted a letter-of-intent for potential pilot participants  of Healo’s beta version product.  This LOI was meant to be a “leave behind” that outlined the pilot’s goals, product functionality and expectations.  We felt this tool would shift the focus (at the end of the meeting) from “customer discovery” to “pilot sales” allowing us to follow-up for direct sales conversations with each agency.

What We Learned

The “pitch meeting” with the MCAMa was a success validating Healo’s potential application in home health.  Overall, reactions to both Healo’s solution and the perceived wound monitoring need were very positive. 

Interestingly, many of these agencies are already using smartphones, electronic health records and other technologies to perform clinical tasks.  However, none of these solutions was focused on wound monitoring, which was identified as a need for 15-30% of each agency’s patient population (further validating our 1st hypothesis).  

There was a wide variation in technological sophistication across agencies that appeared correlated with an agency’s daily patient census.  Among the executive directors agencies, daily census ranged from 100 to 5,000 patients with the larger agencies (1,000+ daily census) expressing the most interest in Healo’s solution.

With that positive feedback, we've already confirmed follow-up meetings with two of the largest agencies in attendance (20% conversion within the 1st week).

These follow-up meetings will be focused on understanding the specific product requirements for home health.  This is particularly relevant as we validated our 2nd hypothesis: Healo needs to evolve its current product offering to include “in-home nurse” functionality.  In addition, we uncovered new requirements, such as EHR integration and multi-user log-in, that will need to be evaluated further.

Overall, Healo has enough positive evidence to continue exploring pilot programs within home health.  However, the team will need to carefully evaluate the extent, and required investment, of any home health-specific product refinements.  The biggest uncertainty is whether these investments in home health will complement or fragment Healo’s solution for its primary target: specialty surgical clinics.

Tips for Healthcare IT Entrepreneurs

Through this experiment in home health, we've identified three “tips” across sales channel, business model and product development.  Though applicable to technology-driven companies broadly, these tips are especially salient for healthcare IT entrepreneurs in the search for product-market fit.

#1 Engage with industry associations for lead generation

Healthcare industry associations, particularly at the state-level, can be an effective channel for generating sales leads at scale.  Only a few conversations can unlock access to dozens of viable customers, business partners and advocates.

#2 Design low-cost prototypes to experiment within new markets

Vaporware, pitch decks and letters-of-intent are effective, low-cost tools to test product-market fit.  Given the regulatory, financial and clinical complexity within healthcare, these tools are particularly useful to mitigate poor investment and product development decisions.  

#3 Target customer segments with aligned payment models

It’s hard to ignore the firestorm that has become Facebook’s acquisition of Oculus.  It’s (literally) sparked fiery emotions and a range of strategic, even philosophical, questions like “how does a crowdfunded company sell for $2+ billion in less than 2 years?”, “did Oculus break a contract with its original crowdfunders?”, and “is Facebook the natural owner of a company like Oculus?”

On the surface, it’s fair to argue that this acquisition is nothing more than perplexing.  Facebook has no experience, or prior success, building and launching hardware.  They are hardly a gaming company (unless you consider them a gaming “platform”).  There isn’t any clear upside in the near-term (or maybe even in the medium-term).  And as a kicker, Facebook already spent $19+ billion to acquire Whatsapp just weeks ago.

A lot this criticism, and cynicism, also centers on virtual reality.  For many, it’s almost inconceivable that virtual reality will be the “next big thing” in gaming let alone mobile computing.  In the search for the next frontier, virtual reality can’t possibly be the winner when it’s up against wearable devices like smartwatches, smartglasses and sensors (so they say).

But this analysis seems flawed: it focuses solely on what Oculus is today, not what it can become in the future.

If you decompose the capabilities that Oculus brings to Facebook, you’ll find the building blocks for the next “killer” wearable computing experience.  At their core, these “blocks” include expertise in display technologies, wearable headsets and virtual reality software.  All surrounded by a passionate developer community.

Together these building blocks are Facebook’s “Trojan Horse”: through Oculus, Facebook can become the premiere manufacturer of head-mounted displays and smartglasses.

Playing this hypothesis out further, it’s not hard to imagine how this might happen:

Virtual Reality (1-3 years) – Oculus’ VR headsets allow for experimentation, community building and revenue generation

Augmented reality (3-5 years) – next-generation Oculus AR headsets overlay a virtual gaming experience onto the real world

Smartglasses (5+ years) – Oculus-branded smartglasses integrate the company’s expertise in heads-up display and augmented reality technologies

Though potentially unorthodox in its evolution, this glidepath for Oculus might be a more viable alternative to Google’s head-first dive into smartglasses, especially as Glass looks poised to struggle without a killer app and lingering product challenges (in the near-term).

However, this hypothetical strategy doesn’t make Oculus a sure thing alone.  But with emerging forecasts predicting global demand for smartglasses to exceed 100 million users by 2020[i], a $2 billion bet for a head-start in this race seems much more reasonable.  We’re already starting to see elements of this strategy emerge within the broader technology community.  Startups like Sulon Technologies and Technical Illusions are hard-at-work developing augmented reality (AR) gaming headsets, while Epson and Vuzix are early leaders in AR smartglasses for the enterprise.

Now, Mark Zuckerberg may have made the worst bet of his career with Oculus.  But I’m increasingly convinced that what seems misguided is actually a shrewd move to become a major player in wearable computing.

“Virtual reality” is the Trojan Horse, smartglasses technology is what’s inside.

The Web 2.0 era is often characterized by the advent of online, social networks.  These networks transformed analog, offline interactions into dynamic, virtual connections that were unbounded by distance, time and cost.  They redefined the internet’s purpose from content consumption to digital interaction.

Seemingly, this narrative has been characterized as a “social revolution”.  The Arab Spring, and the central role played by Twitter, Facebook and YouTube, provided only further evidence.  It illustrated the power of online networks to fuel political and societal change.

However, this narrative is missing part of the story: the internet’s role in a rapidly evolving “economic revolution”.

If we rewind the tape to “Economics 101” (for just a moment), we’d stumble across the conditions for an efficient market, one where supply and demand drive economic behavior.  In this “efficient” world, three conditions must be true:

Open competition – competition, and participation, is open to any economic actor

Price transparency – prices are transparent to all economic actors

Enforceable contracts – contracts between economic actors are enforceable

The inverse, an “inefficient” market, is characterized by limited (or closed) competition, opaque pricing and a lack of standards.  The result: higher costs, suboptimal outcomes and disequilibrium between supply and demand.

Naturally, the question is: how does the internet create an “efficient market”?

At its core, the internet enables online networks (or multi-sided platforms) to bring together buyers, sellers and other economic actors previously engaged in analog transactions.  This digital distribution platform sets the foundation for an efficient market.

We’ve seen this transformation play out, not surprisingly, in the retail sector.  Amazon and eBay created level playing fields for sellers, opening up distribution for companies (or individuals) traditionally shut-out of bricks-and-mortar stores.  They also provided real-time insight into pricing, product comparability, reviews and standard terms-of-service.  Along with purchase tracking, digital payments and analytics that ensure contracts are “enforced”.

Though these “features” may seem insignificant individually, the “secret sauce” is in their combination.  Looking ahead, some of the most meaningful opportunities for entrepreneurs are related to applying these principles to other markets (beyond retail).

This leads to my final question: where are the opportunities to create efficient, market-driven online networks?

The final frontier appears to be more structurally complicated and heavily regulated markets.  In the near-term, back-end supply chain functions, such as after-sales industrial parts or restaurant procurement, seem ripe for disruption (with traditional players like Ariba at the helm).  Beyond that, markets such as healthcare, energy and education seem to be the most likely suspects.

Each of these markets is starting its “glide path” toward truly open marketplaces.  In healthcare, we’re seeing individual elements of open competition (ZocDoc), price transparency (Castlight Health, Procured Health) and enforceable contracts (aptitude).  In energy, we’re seeing more actionable usage and pricing data through companies like Opower.  And in education, we’re seeing the creation of new distribution platforms (edX, OpenEnglish, Skillshare).

At its core, the efficient (digital) market hypothesis is that the internet will disrupt traditionally analog, offline markets through efficient, market-driven online networks.  The cues for entrepreneurs:

significant search costs and a high degree of price opacity for end consumers,

inefficient sales processes and closed markets for suppliers, and

a lack of (or no) digital distribution platforms

Marc Andreessen famously said “software is eating the world”.

I’ll go one step further.  The entire construct we’ve used to understand industries is dead.

For the last 30 years, business strategy has centered on “industry analysis” characterized by Michael Porter’s “Five Forces”.  This analysis was predicated on first pre- defining an industry, like car manufacturing or consumer electronics, and then a comprehensive review of each force: buyer power, supplier power, substitutes, barriers to entry and rivalry.  The end result: the relative attractiveness of an industry and an implied set of strategic choices facing competing firms.

Not only was this thinking pervasive within Fortune 500 companies, it remains the core foundation of Harvard Business School’s strategy curriculum.  It’s the anchor framework taught to the next wave of business leaders here and across the globe.

This is fundamentally flawed.  If not blatantly wrong.

The “Five Forces” effectively presumes that industries are insulated and static, that each industry is mutually exclusive from the other.  It could be argued that “substitutes” and “barriers to entry” seek to address this problem, opening managers’ eyes to impending disruption.  But the flaw seems to be in the myopic view of what an “industry” is in the first place.

The reality for today’s business leaders is that there is no such thing as an “industry”.  Digitization, software and the information age have completely blurred (and broken down) the lines across industries.  This convergence, as Mark Andreessen alludes to, will only accelerate as the boundaries of competition are redrawn by tech giants and entrepreneurs alike.

You can see this playing out (rapidly) today.  Honeywell never thought it would compete with Google.  I bet neither did the world’s largest car manufacturers.  It’s a seismic shift in the structure of global commerce that (not surprisingly) is catching incumbents asleep at the wheel.

So, this begs the question: how should we think about industries in today’s digital economy?

My opinion: like a designer.

Reverse top-down, industry-level analysis toward bottom-up, customer-driven thinking.  Instead of seeing “industries” and “markets” see “problems” and “customers”.  This seemingly subtle reframing is actually a drastic, profound change.  It requires us to throw aside the intuition about strategy and competition we’ve been trained in.  It requires new definitions of “what business” we’re in.

Five years ago had you asked Bose what business they were in: they would’ve said “manufacturing speaker systems”.  But an upstart in Santa Barbara, led by John MacFarlane, reframed the problem: “people want to fill their homes with music”.  It led to a solution that combined world-class acoustics with proprietary networking and software technologies.  That company is now called Sonos.

For designers (and entrepreneurs), this line of thinking is more natural.  We identify a problem.  Hack together a solution.  And experiment.  It’s the underlying mindset that Fortune 500s struggle to replicate.

But it can be done.  It “just” requires the courage to disrupt yourself.

Curt Nonomaque, CEO of VHA, the largest healthcare GPO, challenged his company (in 2011) to reimagine its business before Amazon or Google did.  It led a small team (that I was part of) to reinvent the healthcare supply chain entirely online.  Today that platform, aptitude, combines elements of online marketplaces and big data analytics not seen before in often “tech resistant” healthcare.

It’s one of only a handful of stories of incumbents leading the charge into uncharted “digital” territory.  Though it underscores a simple message:

I have a complaint: the lean startup method has focused too much on consumer-facing products. 

Even at HBS, where the lean method is a core tenant of the entrepreneurship curriculum, we skew heavily toward these types of startups (e.g., Rent the Runway, Zipcar, Dropbox).  In my view, this has come at the expense of how the method applies to enterprise-facing and SaaS companies. 

I understand why this has happened.  First, it’s out of convenience: the examples themselves are easier to find and relate to.  Second, it’s about process: consumer-facing startups tend to focus on rapid product iteration.

It’s this almost dogmatic focus on (often narrow) product experiments that left me feeling like something was missing.  That there was a need to better apply the principles of the lean method to enterprise startups.

To back up for a moment, enterprise startups matter.  Even though consumer-facing startups capture the majority of our attention, and represent some of the biggest names in tech, enterprise startups have (recently) created the majority of value (see here, here, here).

Beyond that, the advent of cloud computing has unlocked new opportunities for entrepreneurs.  Now companies can purchase the “best-of-breed” application for a very specific use case instead of relying on a single technology provider (see here, here).

This brings me back to my initial point: the focus on the lean method has overlooked enterprise startups.  It’s not that the method doesn’t apply.  It absolutely does.  But rather that the process, experiments and tools are different.

What’s so different?  Well, enterprise startups are not just testing product or usability.  They’re also testing their sales cycle and business model.  It’s a holistic process and, as a result, entrepreneurs often struggle to narrow that process into a single “experiment”. 

That's why I wanted to create content for aspiring enterprise entrepreneurs.  I firmly believe that with only $500, without writing a single line of code, entrepreneurs can make more well-informed, data-driven decision about whether to take the “founding plunge”.

Now, you might be wondering: “how do you run an enterprise startup for only $500?”  To be honest, the accounting is pretty simple:

Powerpoint ($0): you should already have this, if not, Google docs is free!

Wireframes ($79): annual cost for a subscription to Balsamiq

Surveys ($25): monthly cost for SurveyMonkey or Google docs is, well, free!

Transportation ($200): for cabs and subway rides if you need to meet in person

Coffee ($100): a “thank you” for people you meet with… though they’ll often pick-up the tab

Today, I’m not going to describe these tools in detail.  Instead, I’m going to write dedicated content (over the next few weeks) tailored to what I’ve used in my own experience:

Process and workflow maps for understanding your customers

Pitch decks for concept testing

Vapourware mockups for “lite” product demos

Sales cycle tracking for prototyping your go-to-market model

Economic value added analysis for cashflow modeling

Letters of intent for building your “beta” version customer pipeline

Yesterday I had a chance to chat with Mark Newhall, Co-Founder and Managing Director of IdealWave Solutions (a tech recruiting firm), at a networking event for the CENE.

As we were eating dinner, Mark said something that instantly caught my attention: "when we're recruiting, we're always looking for the best athlete".  Coincidentally, I'd been thinking along similar lines based on my experience this summer at Wildfire.  The question I had been asking myself was: "are you better off recruiting, and hiring, the best athletes or the best specialists?"

Turning back the clock a few months, what I noticed at Wildfire was that the team, and many new hires, were what I would call "athletes": people from diverse backgrounds that would quickly identify problems and learn the skills needed (on-the-fly) to solve those problems.  This approach wasn't grounded in years of experience, but rather intuition, hustle and raw talent.

This sat in contrast to what I noticed at Google (especially in the search org): many open positions were looking for "specialists" to fill a very specific, often narrow, role.  

This led to a few insights about the answer to my earlier question: it really depends on a company's 1. stage and 2. philosophy.

As for stage, the analogy I like to use is that your "draft" strategy depends on what "sport" you're playing.  

Early- and growth-stage companies are like basketball: it's a fluid, dynamic game that constantly ebbs-and-flows.  And as a result, you draft the "best athlete".  More mature, large scale enterprises are like football.  It's a complicated team sport where no one individual wins the game.  Instead, you need to fill specific positional needs.  And as a result, you draft the "best specialist".

As for philosophy, this really comes down to what you believe about people development.  

If you hire "athletes", you have to accept that the talent is raw.  It requires an investment in coaching.  It requires patience.  It requires a culture that promotes learning from doing (and failure).  If you hire "specialists", you have to accept your implied trade-off of versatility for deep expertise.  It requires a functional organizational structure.  It requires career paths tailored to each function.  It requires diverse, complementary teams.

Interestingly, I've also found this distinction applies to individual careers. 

Personally, I've thought of, and pitched myself, as an "athlete".  Maybe not surprisingly, I literally played every position in soccer and hockey growing up.  I was the rover: I could defend, score goals and even play goalie.  As for my career, I've gravitated toward early- and growth- stage companies and solving ambiguous problems.

Looking ahead though, I fall back on a great piece advice from Paul Limbrey, Head of Sales at Wildfire.  He said: "you can only get by as a smart guy for so long... at one point you need to get as close to the revenue or product as possible".  It's savvy advice that begs the question: "how can you be the best athlete with a specialist bent?"

Jason Goldberg, Founder and CEO of Fab, recently wrote a supremely honest, self-critical and genuine long-form essay on the "16 Lessons Learned in 2013".  If you haven't already, you should read it here.

Beyond the insightful learning (and best practices) Jason shared, I was also struck by his view on blogging.  In particular, he noted that he spent too much time "tooting his and Fab's horn" as opposed to actually "doing the work".  

This fit well with the firestorm I wrote about previously where Keith Rabois said “I don’t know of a single successful CEO or entrepreneur who blogs regularly”.  Jason's comments validated Keith's perspective from the standpoint that using blogging as a channel for "self promotion" is a distraction to what actually creates value.

However, Jason's post was a great example of how blogging allows executives to take stock of what they've learned, codify those takeaways and improve their own performance in the future.  All while contributing valuable advice to others fighting the good fight.

With those intentions, I personally don't see a conflict between building a company and blogging.  Actually, they can be quite complementary.  It's only evidenced by Jason's commitment to write about what he's learning in a long-form post once a quarter.

I was talking to a long-time friend the other day about writing.

I had always been impressed by his (almost) religious daily journal entries while we traveled through Europe in 2008. Especially since I had never been much of a writer and English was my worst high-school subject (behind even French and Spanish… go figure).

What we agreed on – and I whole-heartedly believe – is that writing is a phenomenal “grounding” exercise.  For me, I’m not (usually) a very present person, constantly thinking about what’s next.  But writing has been a great remedy to pause and be “in the moment”.

Beyond that, it’s forced me to really take stock of those often fleeting “aha” moments of insight.  To do this, I started jotting down short reflections, sometimes just a few words, in my to-do list each week.  It’s helped me synthesize what I’m learning and grappling with on the fly.  As much as its let me proverbially “park” my thoughts somewhere else.

Also, for the kid who never quite got his Dad’s “drawing genes”, writing has (started to) become my own form of fine arts, my creative outlet.  In many ways, it’s become a prototyping tool.  By starting to write, I’ve experimented with different styles from more light-hearted (here) to more serious (here).  And developed a backlog of topics to write about at an alarming pace (see: “Snowball Effect”).

Coincidentally, as I was thinking about this post, I stumbled across a vigorous debate sparked by Keith Rabois’ tweet that said “I don't know of a single successful CEO or entrepreneur who blogs regularly”.  This took me by surprise.  I thought it was an overly strong, not well founded argument.  Essentially it implied that “successful” executives are too busy running their companies to do anything else.  With this logic, only journalists (and unsuccessful executives) would have time to blog.  Oh, and apparently venture capitalists?

Personally, what I’ve seen is that the most successful executives (from early-stage to Fortune 500 companies) are never too busy to reflect.  They are acutely self-aware.  They find time to “think”.  This is what I believe Keith misses: blogging is simply one of many outlets for reflection, passion and creativity. 

Frankly, I also think the argument confuses correlation (that most successful executives don’t blog) with causation (that not blogging helps make you a successful executive).  For me, the lesson is that to be a “successful” executive you not only have to put in the work but also the time to reflect on what’s working and what’s not.

On Tuesday I wrote about how founding a company is a lot like dating.  It was a tongue-in-cheek post to describe my views on “running experiments” and “prototyping”.  However, I couldn’t help but feel that I neglected a lot of genuine content.  I didn’t talk about my own struggles deciding whether to take the founding plunge.  I didn’t share any of the lessons learned as a solo founder.  And frankly, I skirted past true reflection.

Well, this is the (first) post to change that.

For (more) background, I spent the last semester working on a startup I believed I was perfectly suited to found.  It sat at the intersection of several past experiences in SaaS (D3 Security, Wildfire), healthcare IT (aptitude LLC) and behavioral health.  And was consistent with my broader vision: that our fragmented healthcare system would become “mapped” through virtual networks.

I actually returned to this idea after setting it aside earlier in the year.  I couldn’t help but feel that I too quickly dismissed the opportunity; it was more a result of convenience and timing that I “put it to bed” than fully vetting and evolving the concept.  So, I hit the ground running diving into prototyping and “selling”: I mocked-up vaporware, created a demo video and made a pitch deck. 

I won’t go into the nitty-gritty details about what did (and didn’t) validate the concept.  But instead wanted to expand on the very personal challenges I struggled with.

First, it was (at times) really lonely.  As a solo founder, I often found myself lost in conflicting thoughts.  I was riding a rollercoaster by myself: one conversation would feel like a complete beating, the next completely exhilarating.  It was a challenge to stay motivated week-to-week, to stay accountable to myself. 

Second, trying to read the “tea leaves” across multiple, often contradictory meetings seemed nearly impossible.  Were the “sold” or “not sold” customers right?  How much negative feedback was a result of technology “skeptics”?  Could I simply design around the potential challenges or did they make the concept “dead on arrival”?

Finally, I felt a constant tension between two roles: the passionate entrepreneur and the venture capitalist.  As much as I wanted to believe I was “right” (and on the cusp of creating the next great healthcare IT startup), as much as I wanted to will my startup into existence, I couldn’t help but play the role of skeptical VC. 

I really struggled with this.  On the one hand, great VCs dig into the market dynamics, customer incentives and revenue opportunity.  On the other hand, great entrepreneurs are fanatically passionate about their vision.  They see something that others don’t, that a model can’t forecast.  I constantly wondered: am I striking the right balance between each?  Am I teetering too far in one direction? 

As a result, I’ve come to a few lessons that will be core to my entrepreneurial journey (and hope they're cause for reflection for aspiring entrepreneurs).

1.       Quickly find mentors and a support network

As I said, founding a company can be lonely (especially as a “lone wolf”).  But mentors are invaluable to test hypotheses, provide encouragement and as forcing mechanisms to “do the work”.  For me, I looked for a balance across healthcare experts (Graham Gardner @ Kyruus), product development (Tom Eisenmann @ HBS) and other entrepreneurs (Rock Accelerator, iLab).

However (looking back), I often felt like I used my mentors more as sounding boards than as pseudo- team members.  In the future, I’ll do a better job of sharing what I’m hearing from the field to really dig-in into the startup’s challenges together.

2.       Mock-up a “business plan” prototype (and work on it over time)

I realize business plans are out-of-favor.  But to help “read the tea leaves”, it’s worth the time to not just capture what you’re hearing from the field, but also synthesize that into your startup’s story.  

Think of it as a “rough prototype” of what a business plan would be.  What is the core problem you’re solving? What hypotheses do you have?  Are you validating demand and business model? 

As an example, I used a Google doc to track insights from all my meetings.

3.       Spend as much time on “recruiting” as “customer development”

I don’t think I spent enough time “recruiting” potential team members (and co-founders).  Though I attended the odd hackathon and talked to almost anyone who would listen, there was still (a lot) of room for improvement in building out a team.  Realistically, you can only go-it-alone for so long.

Luckily, I’ve ended up meeting a team that might bring my vision into the world.  However, it’s come with another takeaway: stay committed to your long-term vision, but don’t be dogmatic about its early execution. It'll help you build the team and expand your horizons about what’s possible.

4.       Understand your own founder profile

Really, the takeaway is trust your gut: understand what will give you confidence to take the “plunge” and what kind (and scale) of business you want to build.  For me, I’m unlikely to be a truly “spontaneous” entrepreneur even though I’m highly optimistic about what’s possible.  I’m just far too analytically-minded to dive right in without doing the work.

I’ll admit: that’s one corny title for a startup blog post.  But (recently) it’s really occurred to me how much founding a company is like dating. 

For background, I’ve spent the last twelve months exploring two startup ideas in depth (one is still evolving post- HBS’s Rock Accelerator) and kicked around countless others. I’ve also thought a lot about how you know when to take the proverbial founding “plunge”. 

It’s clearly not an inconsequential decision: it’s a significant commitment of time, opportunity cost and capital.  And is only magnified once you raise funding (given the fiduciary duty that comes with it).

Now, back to dating. 

I think you’d be hard pressed to find someone that would propose on day one. 

Instead, there’s a somewhat predictable process: you have a first date (make paper prototypes), meet the parents (do customer research), move in together (run a live experiment), and discuss careers and family (vet the business model). 

Essentially, you’re "de-risking" a potential life-long commitment by testing hypotheses and gathering as much information as possible.  And like any great entrepreneur, you've always got an “exit” strategy.

In the end though, every founding story is different.  Sometimes it’s love at first sight.  Sometimes it’s years of dating.  And sometimes it’s a chance meeting.  But as long as you’re in the “game”, you’re bound to stumble upon “the one”.

As for me, I’ve definitely been dating.  Though can’t say I’ve fallen in (startup) love.

p.s. credit due to Wildfire Co-Founder and CEO, Victoria Ransom, for inspiring the “love at first sight” title during a conversation in July 2013

Growing up in a family of entrepreneurs, I’ve always been inspired by the (daily) commitment and conviction of those truly “in the arena”.  And maybe not surprisingly, I’ve spent much of the last year and half (in school) scrapping my way back into it.

During that time, I’ve had a lot of time for reflection: What really matters?  What do I want to achieve?  How can I make the biggest impact? 

Though I don’t have the exact answer, what I do know is that Teddy Roosevelt’s quote about the “Man in the Arena” always rings true.  It’s also a fitting quote for my first blog post: it will guide my writing about startups, “business engineering” and the future.

So here it is: "The Man in the Arena" from President Teddy Roosevelt's speech on "Citizenship in a Republic" (April 23, 1910):

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”