“Creating The Future” Series (Part 2): A Philosophy for Entrepreneurial Success, Purpose and Spirituality

In part 1, I looked at how technology has always brought possibilities of progress and how it can still bring more. I also extended my analysis to how technology can help reverse many current societal and environmental hardships, especially through abundance-creation and regenerative ecological design. I also pointed to a potential shift in mindset that helps take advantage of the tools we build. The following essay is about a deeper shift, the one that happens inside the mind of those creating the tools — otherwise called, in society, the entrepreneurs. It is also, ideally, a reminder that the narrative of technological progress must be brought into being and should be by no means taken for granted as a natural progression… It’s really up to you, me and everyone else to create the future we want!

To be specific, this part elaborates on the personal philosophy needed for technology entrepreneurship, and for building a value-creating business, in parallel, behind the grand purpose. I will aim to deconstruct the concept of “Entrepreneurial Energy”, for technological force cannot be separated from the human force who is imagining it. Without this energy, which both exists within each of us and must be nourished, the future will remain as the present is.

I am going to deep dive into the mindset, values and characteristics that should be embodied by the “ideal entrepreneur”. You, dear reader, might already have this energy inside of you to harness, or can choose to internalize these concepts and embark on your own entrepreneurial venture with comprehensive knowledge on how to act and make decisions at every turn. You can decide to become a technology entrepreneur and translate the technology narrative I described in Part 1 into reality. You may also choose to invest, support or work with others to create the future for you, or contribute in any other form. In any case, you remain an important part of the future of humanity, and I wish you the best of luck!

I. The Technology Startup As A Vehicles For Creating The Future

1. Impact

2. Wealth

3. Creativity

II. The Ideal Entrepreneur: Resolving The 5 Mindset Paradoxes

1. BOTH idealistic/vision-driven AND metrics-driven

2. BOTH loves risk and uncertainty AND strives to eliminate risk

3. BOTH plays the long-term game AND a pragmatic experimentalist

4. BOTH compassionate/human-centric AND hyper-individualistic

5. BOTH a holistic thinker/wisdom-seeker AND unlearns/relearns constantly

I. The Technology Startup As A Vehicles For Creating The Future

P.S. This part can definitely be skipped if you already believe in the startup as a force for good, but before we dive into the characteristics of a successful techpreneur, I would like to make sure readers understand the motivations of founding a startup and how startups maximize.

Startups are risky and made to grow very rapidly, so founders have to know exactly why they’re doing it. The “why” of founding a startup are largely subjective, yet many founder depictions I have seen or read about are nestled within the three following reasons: One to make a large impact on the world, two to create wealth, and three to self-actualize through creative endeavour. Impact, wealth and creativity become the primary three drivers behind entrepreneurial energy. Fast growth, becomes then a means to an end, and a continual process that maximizes those three factors.

1. Impact

“People impact the world through institutions they build. The creation of functional institutions is the means by which people are hugely impactful. People who build institutions are far more impactful than people who don’t, and among those, people who build functional institutions are by far the most impactful…The actions and capabilities of [the founders of functional institutions] determine the future social and material landscape of civilization, and thus the future of the world. Societies with many Great Founders will innovate and flourish, while societies with few will stagnate and deteriorate.” — Samo Burja, The Great Founder Theory

What makes the startup organization one of the primary vehicles for creating the future is that it is “founder-led”. Much emphasis in the venture world is given to the founder, their incentives and their leadership abilities. Incumbents and large institutions have, by nature of their management structure and rigidity, a culture of “make no mistakes”. These kinds of non-founder led business are much often short-termist and utterly lost on innovation because they don’t have an entrepreneurial leader with visionary influence — someone hell-bent on guiding the creation of the new, without any prior commitments and the resulting extrapolation of past success. Startups, on the other hand, are by default building something totally new, and starting with a clean slate. They have small teams who operate outside the institutional managerial hierarchies that hinder freedom and increase bureaucracy. By having both a large upside — and the right incentive structure for the founding team to take advantage of it, as well as a small downside — which is basically non-existent compared to large institutions who have everything to lose — the startup organization, led by its founders, makes creating very large impact on civilization a reality.

“Looking back in the last twenty years, the Internet upended telecom (AT&T refused to adopt the internet and cellular), Amazon disrupted Walmart with a clear vision of changing choice and cost structure that Walmart could not imagine. Netflix, Youtube, Facebook reinvented media, maybe even the elections and politics! Airbnb changed hotels, Google changed libraries and many new and old markets, Uber took over the taxi service, Google Photos and Instagram reinvented how we capture moments. You get the picture here. These industries were not reinvented by large corporations, but in fact the power of ideas driven by technological advances and entrepreneurial energy.” — Vinod Khosla

Through their scale and marketing power, startups can achieve what other movements have never achieved, which is to change whole societies, their behaviours and their emotions. I previously wrote a short medium essay arguing that cultural innovation is essential for startup success, pointing to marketing methods such as “the big ideal” by Ogilvy — which takes advantage of an emerging cultural tension taking the world to a better place — as well as the method of championing of new thinking in crowdcultures — the startup’s brand takes advantage of newly surfacing ideological beliefs to resonate with customers and aligns their vision to them. Andrew Chen writes that “for the first time, it’s possible for new products to go from zero to 10s of millions of users in just a few years. This gives startups an cultural influence that no religion or philosophy can attain in such short times. The notion of a startup taking on cultural innovation, as well as their ability to affect millions of people, means that startups themselves are made for large societal impact, and that their founders should not be thinking of anything else.

“When Uber and Airbnb come to a city, the city changes. They’re gatekeepers, disciplinarians, agenda-setters. They generate massive externalities. Pretending to be mere pandars is how they naturalize those externalities. They say, You must have qualities x, y, and z to access this thing (job, practice, opportunity, service, good, infrastructure). Here’s the catch. It’s up to you to gain those qualities, and we take no responsibility for how you do or don’t do that. So they create new incentives, new ways of behaving, new needs, new aspirations, new identities, new ways of feeling, new modes and means of production, new hierarchies, new solidarity networks, new patterns of inclusion and exclusion.” — Rick Liebling, Editor of The Adjacent Possible on Medium

2. Wealth

“A unicorn is a privately held startup company with a current valuation of US$1 billion or more. Beyond the expansion of the definition of terms to include a slew of companies from all over the globe, there’s been a concurrent expansion in the number of startup technology companies to achieve unicorn status. There is a tenfold increase in annual unicorn production. Indeed, while the unicorn is still rare but not as rare as before. Five years ago, roughly ten unicorns were being created a year, but we are approaching one hundred new unicorns a year in 2018.” — Howie Xu, TechCrunch

Money is usually not what entrepreneurs say they’re in it for. But the reality is that they are motivated in a large part by big financial rewards. Venture capital investors, on the other hand, are mostly in it for the money and publicly commit to return their investment funds and bring profits to themselves. The “unicorn” is a term coined by Aileen Lee, a Venture Capitalist who wrote the article “Welcome To The Unicorn Club: Learning From Billion-Dollar Startups” for TechCrunch. A unicorn refers to a startup that has grown to a $1 Billion valuation. The Billion Dollar Unicorn is a good metaphor alluding not only to the rarity of its occurrence (1 out of 1000 achieve Unicorn status), but also to the mythical nature of success with such high magnitude. Indeed, Hiten Shah, points out that the pursuit of unicorn-hood is carried forward by the drive to dream big and create late outcomes. Between 2013, when the article was first out, and the end of 2018, the number of unicorns increased from 39 to 400+, as well as expanded well beyond the US. The method has since been documented and patterned, which leads to an expectation that this number will increasing even further.

As Mark Coopersmith writes, “During [the last 15 years], the entrepreneurial environment has changed dramatically. Over the past couple of decades in particular, we have reframed the way we conceive, evaluate, launch and grow startup ventures. We have identified particular habits, techniques and tools successful entrepreneurs employ, and defined these resources in ways that aspiring entrepreneurs and innovators can easily adopt to improve their own odds. These proven approaches provide a definitive answer to the oft-asked question whether or not entrepreneurship can be taught.” The idea is that it’s all been done before and documented, so now we know more about generating large impact and large returns. The playbook for such successes are already in the collective consciousness of the startup scene, and it’s anyone’s catch if they can match the patterns, and then try different things until something works within a specific target market.

Paul Graham, the influential founder of Y Combinator, defines a startup as a company designed for fast growth and having no limits in serving a large number of people. The main insight that provides this ability to rapidly scale to $1 Billion is this: technology eloquently removes from a business the need for tangible assets, and replaces it by intangibles (information and automation), thereby creating leverage and enabling exponential results. A networked platform model, for example, can come into existence and grow by collaborating with parties existing outside the company through software. The startup becomes the owner of an unlimitedly scalable and mostly information-based tool, which can be distributed to customers with near-zero marginal costs. In a similar manner, a business model that deals solely with digital services, such as fintech or productivity apps, can provide their value without any of the material limits previously found in physical inventory and manufacturing.

The ideal outcome is a company that has increasing revenues and users, much faster that increasing costs are, as the graphic above shows. This business-building mindset has been crucial for the great companies of Silicon Valley, which is unsurprisingly named after companies who built Silicon chips for very low marginal costs (as its basic material, sand, is very cheap and available). These types of high contribution margin models allow technology startups to reap larger cash inflows as they scale towards larger volumes, especially after using Venture Capital money to cover major up-front fixed costs. In this way, startups can dictate much higher valuations and rapidly so. These methods have even been wholly deconstructed in a book called “blitzscaling”, written by the founder of PayPal and Linkedin Reid Hoffman.

“If you want to understand startups, understand growth. Growth drives everything in this world. Growth is why startups usually work on technology — because ideas for fast growing companies are so rare that the best way to find new ones is to discover those recently made viable by change, and technology is the best source of rapid change. Growth is why it’s a rational choice economically for so many founders to try starting a startup: growth makes the successful companies so valuable that the expected value is high even though the risk is too.” — Paul Graham, founder of Y Combinator

3. Creativity

Technology entrepreneurs are also very internally motivated. They are sovereign, non-conformists and refuse to play by someone else’s rule. As I’ve written before, Steve Blank’s research found that becoming an entrepreneur is largely attributed to a signaling imbalance to potential employers, where entrepreneurs are taking value-generation in their own hands, through their own vision, and in consequence capturing part of that value for themselves. The research proved that “Any individual has incentive to start his own venture if potential employers perceive his productive capacity as lower than he does”. This is why the wealth created from cashing out on startup success is often called “F**k you money”. Nassim Taleb, in “Skin In The Game”, harshly criticize the employability mentality yet touches on a matter that is dear to every self-proclaimed entrepreneur: “By being employees they signal a certain type of domestication. Someone who has been employed for a while is giving you strong evidence of submission. Evidence of submission is displayed by the employee’s going through years depriving himself of his personal freedom for nine hours every day, his ritualistic and punctual arrival at an office, his denying himself his own schedule, and his not having beaten up anyone on the way back home after a bad day. He is an obedient, housebroken dog.” Entrepreneurship hence seems to stem in large part by the drive for freedom

But that’s not only it — the entrepreneur, unlike the employee, is taking meaning-making into their own hand and becoming active creators, rather than passive consumers, which brings with it the long term satisfaction normally attached to personal creation. By launching a product they imagined, they are stepping out of the market hierarchies game and creating their own game, with their own rules which immerse other people in experiences. Marrying creativity with social impact objectives previously outside of traditional finance, the entrepreneur can hence be considered an artist. The artist is moved by a drive to put themselves out there and paint their conceptual thoughts on the world’s canvas. Their art has no rules to how to start, and their business has no “shoulds”. They’re also artists because they treat this canvas as an opportunity to envision a masterpiece of their doing. As Louis Lautman, a Life Style Designer and Transformational Artist, once wrote and inspired in Business Insider, the opportunity an entrepreneur is looking towards is the same as the master painter or sculptor sees and acts upon. For Louis, “It takes a true artist to see something out of nothing and an even greater artist to begin the process to sculpt the situation to match that which they envision.” Their creativity transforms into value, and their creation ultimately becomes part of a new world.

“The value of products and services today is based more and more on creativity — the innovative ways that they take advantage of new materials, technologies, and processes. Value creation in the past was a function of economies of industrial scale: mass production and the high efficiency of repeatable tasks. Value creation in the future will be based on economies of creativity: mass customization and the high value of bringing a new product or service improvement to market; the ability to find a solution to a vexing customer problem; or, the way a new product or service is sold and delivered.” — Jack Hughes in the Harvard Business Review

Steve Blank, Silicon Valley guru, also engages in one of his blog posts in comparing entrepreneurs to artists, and notes that by building something new and operating in chaotic environment, entrepreneurs and their early team are acting like improv jazz musicians — everyone is playing along the music of the founder’s vision. We can see here that creativity in entrepreneurship is also about assembling a team of co-creators, to whom the entrepreneur’s vision can also transfer meaning. Early startup employees are, and should, be joining because they believe in the vision and creative abilities of the founder. The same creative purpose of the founder transforms into the whole company’s mission statement. The bigger the mission the more the missionary will have people by his/her side, supporting the mission and taking it up as their own (this extends from employees to investors and partners). It is, after all, shared mythologies and stories about the world that have always moved humans and led to collective action. Having a team of 100–1000 people working on the same canvas, can really only be done in a business-platform context, and this is catalyzed by fast-growth and large fundraisers.

“For the sake of the [Entrepreneurship is an Art not a Job] analogy, think of two types of artists: composers and performers (think music composer versus members of the orchestra, playwright versus actor etc.) Founders fit the definition of a composer: they see something no one else does. And to help them create it from nothing, they surround themselves with world-class performers. This concept of creating something that few others see — and the reality distortion field necessary to recruit the team to build it — is at the heart of what startup founders do. It is a very different skill than science, engineering, or management.” — Steve Blank, author of The Lean Startup

II- The Ideal Entrepreneur: Resolving The 5 Mindset Paradoxes

“The power of paradox — many of the world’s top entrepreneurs and great thinkers share a rare skill called “integrative complexity” — the ability to develop and hold opposing traits, values, and ideas and then integrate them into larger ones” — John Hagel, Management consultant

Little did I know when I first started my analysis how true this quote I saved some time ago is. The initial objective of my analysis here was to understand and be able to describe the philosophy needed to build large-impact, tremendously creative, billion-dollar unicorns. After first putting down the 10 traits that I believe an entrepreneur must have or develop, I saw that for every trait there has an opposing trait. And so the 10 traits combine into 5 paradoxes. I have arrived at a point where I believe the ideal entrepreneur is a paradoxical and complex figure. I also found that indeed many business academics have written about the multiple paradoxes of entrepreneurship, but none fully dedicated to technology startups, and as far as I know none of them try to resolve them. And so the graph below was born.

F. Scott Fitzgerald famously said that “The test of a first-rate intellect is the ability to retain two opposing ideas in your head at the same time and still retain the ability to function.” Luke Turner seemed to have taken this idea forward in the Metamodern Manifesto, and wrote the following: “Movement shall henceforth be enabled by way of an oscillation between positions, with diametrically opposed ideas operating like the pulsating polarities of a colossal electric machine, propelling the world into action.” The ideal entrepreneur, therefore, is someone who acts in a way that moves in the areas of potentiality between each two opposite elements, but also containing them, and combining the two extremes which on the surface were thought impossible to integrate — in a sense, they operate as an electron in quantum expression (as Hanzi Freinacht has explained about such paradoxes). And by recognizing that both polarities are useful to the entrepreneurial journey, they do not choose one side and eliminate the other — on the contrary, the outcome will be better if they aim to resolve the dilemma by integrating both sides into superposition.

The ideal entrerpreneur, which embodies the philosophy I describe below, is a description of a person I would like to work with, and even a person whom I wish every entrepreneur out there embodies. He/she also is, in a way, the person who I personally aspire to be in order to partner with entrepreneurs and “complete” them. I went ahead with my analysis and tried to nail down the paradoxes by thinking of ways in which they can be resolved. So now I’ll look at the paradoxes one by one, starting with a description of how each polarity alone is useful, then at how the paradox might particularly be resolved in a way that maximizes the startup’s success.

“Innovators understand that it is necessary to believe to see. They believe in what does not yet exist. They see what most do not see.” — Murilo Bueno, The Innovator’s Mindset

Idealism is the view that reality is constructed by the mind. Entrepreneur are, unlike those too involved with living in the boringly crushing dream worlds of other people. They see that the whole point of being is to figure out how their own existence brings creative potential for far-reaching societal improvements. Entrepreneurs live a different life than those who do not dare crossing their comfort zone. Just like the large percentage of traditional companies who are in perpetual fear of losing what already exists, there is a large percentage of people who are in perpetual fear of failing. They are stuck too deep in the status quo to notice the potential of making the future radically better. Entrepreneur rather take the path of both imagining alternative directions to the future and believing that they can happen through their own doing. They, indeed, have their own vision and look to it through an optimistic and romantic perspective. And this makes them uniquely qualified to really build the thing they want to build — no one else can do it, because no one else actually sees it.

Entrepreneurs are a breed of people who, with their own vision, decide to reshape reality and live in their own. Entrepreneurs are in that sense, idealists, and it is mostly their far-reaching imagination that pushes them to act. An entrepreneur is almost every time moved by noticing a gap in reality that creates an open-ended narrative. The narrative is completed through an act of personal imagination, and the world suddenly seems different. They see how things evolve from their own action. By developing, on one hand, a personal conviction of how the narrative will unfold, on another hand an obsessive belief in reaching the end, the entrepreneur becomes the hero of his own narrative. This apparently creates an additional amount of personal meaningness. When an entrepreneur sees the future they want to create, and the narrative’s end, reality is both enriched and meaningful — the boundary is eliminated, and imagination becomes truer than naked facts; fiction becomes stronger than the real world.

Good entrepreneurs are hence like good fiction writers — they create a worldview in which their products exist, and in which other people adopt its own language and norms. Instead of living in someone else’s world, it is now other people who are living in the entrepreneurs’ world. The fact that product value lies in creativity, as we have seen in the previous section, means that the tools they create can embody the imagination of their designers. Techne, as we have pointed out in Part 1, becomes a kind of art where the designer’s mind turned inside out. Software is eating the world and digitizing it, it is taking offline experiences into online experiences — like how the retail store became the ecommerce website, how a live music concert can become a playlist on Spotify, or how cash payment became a mobile-based digital transaction. It won’t be long before the latter, in each of those transformations, will become something else, i.e a virtual shopping mall, launching your own virtual music concert, and mind-to-mind data transfer. As virtual world creators and biotech engineers become some of the most hyped “jobs” of the future, we can see how the technologist’s mind is moving towards further and further reality-design. In mixed reality, as well as biotechnology, software can even amplify, or modify, the real world by adding pixels and DNAs.

“Bold ambition is becoming fashionable. Competitions like the X-Prize, moonshot initiatives such as Google’s “We Solve for ‘X’, and institutions like Singularity University are all focused on deploying radical science and technology ideas to address global problems and challenges. Investors, entrepreneurs and innovators are increasingly focused on the pursuit of the seemingly impossible with venture ranging from low cost sustainable housing and universal education, through to hypersonic travel, colonizing space, and asteroid mining. This desire “to boldly go” where others dare not tread will drive a constant stream of ever-more ambitious initiatives. “— Rohit Talwar, futurist

If you’ve heard the words “Moonshots” and don’t think of technology businesses, then you’re far away from reaching startup enlightenment. Clearly, profit is required for long-term viability, but early-stage investing is mostly focused on other things than profit come first — the grandeur of the opportunity, the nature of the universal problem being solved, the ambitiousness in the founder’s mission. At an even higher level, some venture capital investors themselves have started to envision their portfolio companies as vehicles for building good societies and for social impact on the planet. They too have started to find meaning and purpose in the visions painted by the entrepreneurs they back. Some prominent VCs like Marc Andreesen & Josh Wolfe have publically announced that they prefer to invest in radical products “that look like they are crazy” and straight from science-fiction, because they see financial opportunity in the non-obvious and the non-consensus narratives — which are for them proxies for producing extreme outcomes.

“There are obvious kinds of science fictional modes going on in the way you seek and obtain venture capital funding, for example. Business plans can be as science fictional as novels, depending on the product: think of social media companies like Snapchat and WhatsApp whose future profitability is almost entirely conceptual. As a person seeking venture capital, you write a speculative narrative about all of the value your company is going to produce based on the glorious IP it has, but nothing concrete exists yet. But then the company and the IP does become materialized as money, as economic activity in the stock market and other markets based on how compelling your narratives are. Monetary value may be based more on the quality of the story than on the quality of the product.” — Sherryl Vint, a professor in the Department of English and the Science Fiction and Technoculture Studies program at the University of California

On the other side of this paradox is the big question of startup execution: How is it that we transform the speculative value into real material value, be it financial for owners, or economic for customers? We can talk forever about our own grand plans and visions — and everyone has their own — yet any successful startup business also has to be methodically pragmatic about accomplishing those plans. In dreaming about startup success, an entrepreneur must not forget that business is around numbers, so he/she has to be asking “how do we make the numbers work” and measuring success by tracking it through the right metrics. According to Elizabeth Yin, Co-founder at the Hustle Fund and former partner at 500Startups, the best entrepreneurs are also metrics-driven (In addition to being vision-driven), and for her this means that they fully understand one how to track the levers that drive the business and two how to the align of the team around these levers. The metrics measured would accurately reflect underlying business performance and provide insights into why a company will succeed in reaching the vision. The numbers themselves will tell if the team is getting closer to, or is in the right direction to the ultimate goal.

“Very often we see that a transformational idea, pushing the boundaries of our existing system, loses its power when implemented. We observe that most ideas regress during the process of realisation/manifestation. Transformational ideas are often not financially sustainable. New business ideas or social initiatives fail to attract funding, customers or users.” — Keks Ackerman, entrepreneur and metamodern writer (Future Sensor Publication)

Therefore, one of the main task of the entrepreneur, after clearly defining the imagined mission of the startup, is translating “Mission” into “Metrics” that will guide the materialization of their unbounded imagination — especially in a business context that, needless to say, abides by the constraints of the market. “By tracking progress consistently”, Sofia Quintero from Techstars writes, “it becomes easier to iterate quickly and make noticeable improvements.” While mission and meaning move the entrepreneur in the background, metrics enable action and iteration loops on a daily basis. Because once you know the specific output that you’re aiming to reach (say it’s to grow revenues by 20% monthly), you can better manage the inputs you can control (say increase marketing expense by 3x, or improve customer sales support by 50%) that move metrics like revenue-growth and others. Numbers can help build a mathematical model for the growth engine of the business, in which the entrepreneur can play with the numbers and prioritize resources that really make the output much larger. It is only in this way that moonshots can come into being.

“So much emphasis, particularly within startup communities, is given to imagination. Imagination is the ability to see the world in a different way, yet an organization that relies on imagination alone may be at risk. Without the experience and observation accompanying it to reduce an idea to practice — an imagined idea remains trapped behind the brick wall instead of inventing and implementing ways around it.” Karen Roter Davis, Hi-Tech Executive & Advisor and portfolio manager at Google X

While many might solely see metrics in relation-to business performance, there is another mindset in product management that looks at customer-centered KPIs. This mindset is relevant for ambitious and impactful visions because the change we are trying to bring is at mostly at the customer level. This mindset stems, as argued by a fascinating post by product thinker Jan Milz, from the fact that we should be measuring progress from the customer journey’s point of perspective, rather than only from the startup’s financial perspective. For example, instead of measuring the number of subscription conversions or an ARPU figure, we rather be measuring the amount of time a user is spending with the solution and how it’s leading to an upgrade in their life. In many startups, the latter measure is a proxy for customer satisfaction and potentially shows that customers can later be monetized when they become loyal users. In making one of one of the most important metrics for startups work, the ratio of customer lifetime value to customer acquisition cost — AKA as unit economics — and all their sub-metrics, the customer value proposition is tracked, pursued, and optimized until it works. Have an ambitious/attractive solution, and the marketing costs per user goes down. In parallel, have a great/useful experience, and the CLTV per user goes up. Once the unit economics work, the founder has a high likelihood to attract large funding (as late-stage growth investors will be mostly looking at this metric) and hence to reach the imagined end-state.

“Only the customer knows if a product helps in making progress or reach a specific goal. And they measure the hired solution against an expected outcome. She simply will not care for your company goals. And while we think we are doing great because KPIs are great this might not be the truth for the customer. That’s why we need to think in user-centered KPIs. “ — Jan Milz

“Most people in business reduce the risk of failure to the point where the consequences of success are inconsequential on society, but they can make money for their shareholders as they are obligated to. My philosophy is different. I’d rather invest in something with a higher probability of failure if the consequences of success are consequential. There is as much profit and increased social impact to be gained here, although with a higher variability ” — Vinod Khosla, Entrepreneur and Investor

At first sight, this paradox between taking risks and eliminating them is confusing. Remember we started talking in the introduction about not being able to predict the future, about complexity, and about the uncertainty-loving “generation flux”. These ideas will become more practical here as we resolve the paradox and explain how uncertainty about the future can be translated into extreme business outcomes. In the uncertain early stages of forming a technology company, achieving a kind of linearity in prediction and modelling is a hard task, as what goes in doesn’t only depend on your company’s actions — there are hundreds of external variables that may affect your outcomes. Consumer needs are always changing, the market environment is always changing, and new entrants will always be attempting to copy or disrupt again. The presence of complexity not only makes analyzing the current landscape harder, but also makes inaccurate the prediction of any future state where the startup wins.

“Like it or not, we live in a world of butterflies and black swans, and it goes without saying that this increasing unpredictability has enormous consequences for business. Connectivity, complexity, and unpredictability, therefore create challenges of a different nature than those that we had to deal with in the past. And this forces us to change our way of thinking about strategy, planning, forecasting and organizing.” — Julian Birkenshaw, London Business School professor writing in his book ‘Fast/Forward: Make Your Company Fit for the Future’

Startup-building can be thought of as the engagement in building a huge organization with the knowledge that it is a flawed or unachievable task. The entrepreneur attempts the impossible in spite of skepticism and predestined failure. In a long essay on startup ideation, Jeron Paul asked: “What startup founder is typical? What startup journey is typical? All of them are outliers…The odds are the business will fail. We might even say that it is effectively surprising that any startup, given their outlier status, succeeds at all.” The odds of actual startup success — as shown by the low percentage of startups that make it and really reach the valuations needed by early-stage investors — are very low at close to 500 to 1. Yet founders know that improbable scenarios are the only way society can advance; they take the risk anyway and so do their early investors. The reason for that is clear, there’s a chance that the impact they would have on the world is incomparable and unprecedented, and that our society will forever be changed if this thing they’re building actually works.

Technology entrepreneurs have a high tolerance for risk-taking and are willing to change the world by imagining what’s possible, even sometimes making the impossible possible. As Peter Drucker explains, “Entrepreneurs discover, evaluate and exploit opportunities; they initiate and motivate the process of change.” Change plays a great part in storytelling and almost every story we tell has its dramatic change moments. At the heart of every worthy entrepreneurial story is a theory of change and novelty. But change is always hard. The future, hence, belongs to those dreamers who think of these unreasonable possibilities, who take on a mission regardless of the improbability of success, and who take bold, large, risks which carry with them equally large rewards. They go after the project that has 1% chance of success and a payoff of $1B+, instead of the project that has 90% of success with $10M dollars in outcome. As Vinod Khosla explains, “Improbable things happen all the time and probable things fail to happen all the time. Otherwise there wouldn’t be risk, probable things happening has no rewards at all.”

Michael Mauboussin and Richard Zeckhauser explain that extreme financial outcomes in venture come from the state of extreme uncertainty/complexity and even of non-knowledge, and that the wise entrepreneur operates by seeking to become “antifragile” rather than trying to predict outcomes that are not computable (Nassim Taleb defines antifragile people as ones who love adventure, risk, and uncertainty and thrive when exposed to volatility, and randomness). A mindset that accepts and loves uncertainty is critical because, in the early stages of a venture, you are operating only based on hypotheses — with very little data and little clarity on many things such as market demand, product NPS and unit economics. From an investor’s perspective, betting on unproven hypothesis before everyone else dictates that the price they’re paying to own part of the venture is actually a bargain, and that if proven right will generate 10–100x returns on the long-term.

Goals are often crafted with ambitious expectations and try to ignore the fact that chance occurrences will disturb their best-laid plans. And by trying to ignore this random factor, they become extremely vulnerable to them. According to LBS professor Elroy Dimson, risk means “more things can happen than will happen”. As a founder or early-stage investor, the best way to increase your startup value is to kill failure by addressing risks — subsequent investors are then supposed to pay a higher price because they are taking less risk. The most important principle is to avoid risks that, if lost, would wipe you out completely. Some of the best investors follow this method, from Josh Wolfe of Lux Capital who says that “Failure comes from a failure to imagine failure”, to Leo Polovets from Susa Ventures who has his own “startup as a bundle of risk” valuation framework.

“The future should be viewed not as a fixed outcome that’s destined to happen and capable of being predicted, but as a range of possibilities and, hopefully on the basis of insight into their respective likelihoods, as a probability distribution.”

Guy Thurner (early stage VC at Hyde Park Venture Partners) makes the difference between Uncertainty (which is the unknown future state of the world, and you don’t really know how customers are going to respond to your product) and Risks (which are defined and known possible outcomes where probabilities and business impacts are understood). Guy believes that it is an entrepreneur’s job to design the right processes that translate uncertainty into specific risks in order to gain a significant edge, as well as that startup founders should do more forecasting — which for him is about assigning probabilities and risks to different outcomes and then going out to find the evidence needed to support the analysis. Every venture strategy and business plan, is hence made of a set of unproven hypotheses until put into execution, and that’s what good entrepreneurs do when de-risking.

By transforming uncertainty into probabilistically-calculated risks, we are more likely to understand the likelihood of events that can impact the business and hence not only make higher-certainty decisions that lead to growth outcomes, but also know exactly what resources are needed to wholly eliminate the risk of not growing. “Our lack of perfect information about the world gives rise to all of probability theory, and its usefulness. We know now that the future is inherently unpredictable because not all variables can be known and even the smallest error imaginable in our data very quickly throws off our predictions. The best we can do is estimate the future by generating realistic, useful probabilities.” Entrepreneurs with better data about different variables can ultimately back-up their assumptions in predicting future outcomes — hence better strategize and increase the level of preparedness.

It’s always good to plan for the worst because “what can go wrong will go wrong” as per Murphy’s law. Whenever planning for something, it’s good to start with the biggest risks we can foresee and make our way through the rest, also making sure you don’t do anything stupid because sometimes, avoiding stupidity is easier than seeking brilliance. If they can find the fatal flaw before they write their business plan or before it engulfs their new business, they can deal with it in many ways. They can modify their idea — shaping the opportunity to better fit the hotly competitive world in which it seeks to bear fruit. If the flaw they find appears to be a fatal one, they can even abandon the idea before it’s too late.

Polovets, in his words, essentially says that there are 9 major risks:

• Product/Market Fit Risk (is your product something that people want?)
• Product Quality Risk (can you build a great product?)
• Team Risk (do you have a great team for achieving your vision?)
• Recruiting Risk (are you able to grow your team effectively with strong talent?)
• Sales Risk (can you and your team sell your product effectively?)
• Market Risk (is your target market large enough to support a huge company?)
• Funding Risk (do you have enough capital to hit milestones that will either let you raise more capital on better terms, or get you to a place where you no longer need to raise capital?)
• Short-Term Competition Risk (are you differentiated enough from existing competitors?)
• Long-Term Competition Risk (will you be able to fend off strong, well-funded competitors in the long-run?)

“Imagine all the things that can go wrong, then you can flick them off the table, because I think of it almost like the first law of thermodynamics, like energy is not created or destroyed, risk and value just change form. Technology risk, product risk, market risk, finance … All those things are risks. I kill one of those risks with time or talent put into it. If you’re a subsequent investor, you should be paying a higher price and demanding a lower quantum of return, because you’re taking a low quantum of risk.” — Josh Wolfe, VC

As a simple and practical example, the very early stages of a startup revolves around systematically reducing product, market and team risk to be able to get to series A financing. A company which has reached product-market fit, and has experienced founders who know their market inside-out, will be worth more than another startup without those characteristics. A VC’s job is to find the least risky point to invest in a company relative to what they can afford to invest, and a founder’s job to imagine all the things that can go wrong in his business, start tackling the biggest risks they could foresee and make our way through the rest, one by one. Ultimately, lowering risks drive higher valuations. A unicorn, to be specific, is built only by embracing huge uncertainty about the future and taking risks, then proceeding to kill them and proving oneself right.

“I think the biggest competitive advantage in business — either for a company or for an individual’s career — is long-term thinking with a broad view of how different systems in the world are going to come together. One of the notable aspects of compound growth is that the furthest out years are the most important. In a world where almost no one takes a truly long-term view, the market richly rewards those who do.” — Sam Altman, Y Combinator

Unlike traditional lifestyle businesses and public organizations, startups are most often temporarily organizations that are made to scale fast on a 5-to-10 years period and that are packaged to be acquired or exited by the original founders and early investors through equity sale. By this mandate, technology entrepreneurs are naturally playing the long-term game when they start out, and must look at what will become of the company deep into the 10-year future. This kind of long-term thinking starts by an ambitious mission, and by a vision for real change, as I argued previously — and change, it appears, takes a long time. Most startup success stories we hear about in the media are mistaken for overnight successes, yet none of them really happened overnight. Writing about “the exponential mindset” — which is an ideal process of ever-growing output with little input — Jesus Gil Hernandez makes it clear that “At the start, it takes vision and a leap of faith to commit to the unknown. In the early days, it takes courage and patience to build the foundation for growth even when results aren’t yet apparent.”

By that account, we would believe that the mindset of playing the long-term game (and succeeding) is very much different mindset than that of a slow growth-oriented, and incremental change-led. Surprisingly, it is not. The long-term view, alone, is not enough. It has to be combined with the ability to operate in “failure/learn” mode. By the time one starts to dream about the future they want to create, they should have already started executing and letting the world judge their ideas. Entrepreneurs have to both strategize for the long-term and test today, knowing that any strategy is temporary and ultimately unpredictable. Practicing strategy today is hence about balancing the long-term view with organizational processes that help create systems for repeatable wins. The technology ecosystem, in this way, seems to give emphasis to long-term change and to short-term execution at the same time. When change is the only constant, strategic long-term planning can only create a semi-coherent direction, but the strategy is only completed with real-time experimentation. So while the entrepreneur is working every month to achieve the 20–30% incremental change towards the grand objective, they also must be looking to innovating with 10x mindset.

Playing the long-term game means sacrificing instant gratification today, and even maybe suffering by doing the hard things that pay off in the future. Playing the long-term also means sticking to your mission after everybody else would have given up. Playing the long-term game means having an exponential mindset that can fathom bold ambition and global impact. As Sam Altman reiterates in his essay on success, “Almost always, the people who say ‘I am going to keep going until this works, and no matter what the challenges are I’m going to figure them out’, and mean it, go on to succeed. They are persistent long enough to give themselves a chance for luck to go their way.” During the early stages of launching a venture, no one is there to witness a founder chasing their first supplier-partnership for months, or the twenty “NOs” they got from investors who didn’t believe the story for every one “YES” from those who did, or the non-scalable messy growth tactics used to go from 100 to 1,000 customers, or even the many wrong paths taken on the months-long journey from 1,000 to 10,000 users. No media ever tells about those struggles, yet the great entrepreneurs get to work regardless, because they believe that every step they’re doing today will matter on a longer horizon, and that the pieces of the puzzle will somehow fall together after multiple tries.

“The first step to the long game is the hardest. The first step is visibly negative. You have to be willing to suffer today in order to not suffer tomorrow. This is why the long game is hard to play. People rarely see the small steps when they’re looking for enormous outcomes, but deserving enormous outcomes is mostly the result of a series of small steps that culminate into something visible.” — Shane Parrish, Farnam street

As Jordan Bates from HighExistence notes, “You realize that what other people view as an insurmountable challenge can actually be broken down into clear, small, manageable actions that gradually cascade into major shifts.” And so the best entrepreneurs are the ones who build the future one step at a time, laying brick by brick and testing if each brick will hold, but also if the structure as a whole will hold with the help of any single brick. By bringing together both looking at the horizon and pragmatic experimentation, entrepreneurs thus understand that they have to constantly make small and fast decisions — because the faster decisions are taken, the faster the startup will be moving towards its grand objective — and that’s because of the compounding effect working in this favor. Naval Ravikant, a prominent entrepreneur and tech investor, for one, says “the compound interest from many small iterations is greater than the compound interest from a few big iterations”. Shane Parrish additionally writes that “What starts small compounds into something more. The longer you play the long game, the easier it is to play and the greater the rewards.”

Steve Blank makes it clear that the defining characteristic of a startup is that of experimentation. For him, experiments are the only way a startup can align a vision with reality, and truly find a repeatable and scalable business model to support the grand vision. The concept of the “lean startup”, is materialized out of this mindset of experimenting with change. Its main practical insight is this: Generate hypothesis instead of plans, test them as fast and minimal as possible, and get customer feedback — then repeat. The most-overheard startup advice is to “fail fast”, but what does it mean? It means that the failure path has given us a sign to go through a different path, and that we are closer to reaching the end. Ken Norton, Senior Operating Partner at Google Ventures, explains: “Trying something remarkable requires failure, and failure is learning.” For him, every failure provides new insights into problems, customers and products — those insights become lessons for tomorrow. Silicon Valley and most successful startups run by this fail/learn process. Silicon Valley, in fact, culture can be described in one, and sentence (and I am paraphrasing Benedict Evans, an analyst at the a16z fun): “Run thousands of experiments, most will fail but there will be a few winners which will really really work!”

Led by product analytics and big-data crunching, the entrepreneur has to be testing every cause-effect relationship and input-output relation which he/she thinks may be true, to really understand what works with customers and what doesn’t. Scaling towards the grand vision happens with constant feedback from the complex and real world of interactions and relationships — a kind of feedback that shows you the right way to bring about real change. Donella Meadows, complexity scientist and author of “Thinking in Systems: A primer”, playfully describes creating the future as a dance with systems. For her, the approach of trying to predict and control outcomes is not the right one. “Systems can’t be controlled but they can be designed and redesigned”, she adds. Her practical advice, instead, is to combine our imagination and values with a process of iterative learning from observing the properties of systems and the surprises they generate. In a similar play fashion, Kathleen M. Eisenhardt and Shona L. Brown, who wrote the paper “Competing on the Edge: Strategy as Structured Chaos” described this strategic process through a metaphor of musical improvisation where there is only specification of a few crucial rules; the rest comes from real-time and unpredictable creativity.

“The general underlying principle here is to play the long game, keep your options open and avoid total failure while trying lots of different things and maintaining an open mind. Focus more on avoiding things that don’t work than trying to find out what does work“ — Buster Benson, Author and Previously product at Patreon, Slack, Twitter, and Amazon

In the book “Switch: How to Change Things When Change Is Hard”, Dan & Chip Heath recommend that one of the main processes for bringing about large changes is to find the bright spots, and then double down. Through experimentation, pragmatism, and the right analytics tools, the bright spots will be clear to the entrepreneur. Dan & Chip write that “ To pursue bright spots is to ask the question “What’s working, and how can we do more of it?” Sounds simple, doesn’t it? Yet, in the real world, this obvious question is almost never asked. Instead, the question we ask is more problem focused: “What’s broken, and how do we fix it?” Instead of repeating the same mistakes expecting different results, the better way is to stop and think about that time when things were working the way you want them to be, then rework the context and steps that got you there. Or maybe try small nudges in different directions and see if any stick, then scale those successes. Each forward step brings with it a deeper understanding and tells you what the next step should be. Andy Hertzfeld, the architect of the original Macintosh, puts it this way: “I think the essential way to do anything great, you have to have some incremental development philosophy because you’re just going to be wrong with your grand design that you don’t iterate on.”

The final thread to go on in this paradox of “long-term thinking VS pragmatic experimentalism” is the concept of idea generation. I have slightly touched on the topic in a previous essay on “the idea maze”, on how ideas grow like trees and then branch out, or even bloom like flowers until they become beautiful. While many think that innovative ideas are mostly born from small hunches and “Aha-moments”, The reality is that startup ideas take time to develop. Just like scientific discoveries, ideas often take years in time and multiple precedent discoveries in numbers to really come to light. Many startup ideas start simple, and as many VCS refer to as “looking like toys”, and take hundreds of hours of team discussions and mission expansions and to turn into something really visionary. It could, as seen with Facebook, start with a website to compare hotness between Harvard students, and suddenly 5 years later you have the largest social network connecting the whole world. Steven Johnson of “Where Good Ideas Come From” wrote that many important ideas have very long incubation periods and can often linger on for decades in the back of people’s minds.

“A yearning for innovation requires real exploration. It requires a persistent search to try (and fail) to move your understanding forward with a new tool, a new technique, a new insight. Sadly, the first innovation often isn’t even all that helpful, but may well provide a path to ones that are. This is an idea that Steven Johnson of Where Good Ideas Come From popularized called the “adjacent possible.” Where finding your way through a labyrinth of ignorance requires you to first open a door into a room of understanding, one that by its very existence has new doors to new rooms with deeper insights lurking behind them.” — Sam Hinkie in his Philadelphia 76ers Resignation Letter

“In response to a clear challenge to develop the intellectual depth and resourcefulness required to address a complex and fast changing agenda, an increasing number of leaders are turning to spiritual practices such as mindfulness meditation to help tap into the capabilities of our subconscious mind and tune into our intuition.” — Rohit Talwar

In today’s world, spirituality is becoming trendy for two reasons: there exists a spiritual hunger in many of us, especially non-religious millennials, for a) feeling a divine attunement with the universal higher power, b) feeding the soul with a transcendental and meaningful existence. The goal of a meditation practice, is to arrive at the non-dual awakening state where you realize that you are connected to all other human beings, the whole of life and the entire planet. We see everyone else as part of us, and everything else, as part of us as well. Another spiritual aspect, relevant to the modern globalized world, is pluralistic world-centricity. This is what Ken Wilber defines as integral theory, and what he links in his book “Integral Buddhism” to the future of spirituality. In an entrepreneurial context, the individual motivation is deeply associated with a social and spiritual value, and the entrepreneurial opportunity itself might emerge from and feed off a need for social impact and solidarity with others. Hence, the success of the venture is dependent on compassion, where the entrepreneur responds to and works in major part to alleviate it the suffering of others.

“This century, this age of collapse, urgently calls for us to expand our moral horizons to include all of us. That’s the only way we care about the planet, about inequality, about greed, about everything going wrong — by caring about everyone on it. Because now that human activity envelopes the planet there is no ‘out group’ for us to compete against, no external pressure to drive the emergence of global cooperation. And yet we are faced with existential problems like climate change and nuclear war which can only be resolved at the planetary level.” — Umair Haque

Meditation, and spirituality in general, are starting to become essential for leading a fast-growing business and facing all the complexities of it. In order to run a technology company and achieve large societal impact, the entrepreneur will have to deal not only with a universal mission that spans many cultures, but with specific individuals from all backgrounds — with different ambitions, different motivations, different dreams. By attaching oneself to the startup’s fast-growth world-centric mission, the entrepreneur would have to strip away part of the ego and embrace every person whom the business might touch, including the millions of customers they will have at scale, and also be empathetic the investors who don’t share our vision and those who do, with the partners we will be working with for a long time, with their diverse team of employees who represent wide cultural and ideological diversity. Technology, and the scale it can reach, is itself a catalyst for brings increasing awareness to other cultures, from which the entrepreneur can learn to look for commonalities that put everyone else in equality before the network built by the company. As M. C. Bateson wrote, designing modern social systems would have to be informed by a switch, from the machine age when we tried to create schools to be like factories, to an ecological age, where the design of institutions is done in terms of maintaining the quality of life for our species and for the whole planet.

“A human being is a part of the whole called by us universe, a part limited in time and space. He experiences himself, his thoughts and feeling as something separated from the rest, a kind of optical delusion of his consciousness. This delusion is a kind of prison for us, restricting us to our personal desires and to affection for a few persons nearest to us. Our task must be to free ourselves from this prison by widening our circle of compassion to embrace all living creatures and the whole of nature in its beauty.” — Albert Einstein

Compassion, however, must not really oppose the other side of this spiritual equation, which is reaching a wholly meaningful individual existence. Far too many people never really become themselves - their thoughts remain other people’s opinion, mimicking friends and family, and imitating the career aspirations of those they long to impress. Our ego has another limitation, which has a strong need for the approval of and communion with others, helps develop increasing influence our culture has over us by looking to societal norms for guidance. This insight, adapted from Oscar Wilde, is meant to awaken the soul into overcoming the cultural thoughts that imprison one’s own creativity, to stop current societal beliefs from putting a limit on one’s worldview. Terence McKenna would call this the diminution of humanness, or a lack in realizing one’s true potential. The point is that one should not only fear social conditioning and entrapment but also strive to be different and unique, to have one’s own opinions, to reject what others try to indoctrinate with and make one do what they want — in short, being a true rebel.

“We fear our highest possibilities…We are generally afraid to become that which we glimpse in our most perfect moments, under the most perfect conditions, under the conditions of greatest courage. We enjoy and even thrill to godlike possibilities we see in ourselves in such peak moments. And yet we simultaneously shiver with weakness, awe, and fear before these very same possibilities.” — Abraham Maslow

In our context of entrepreneurship, the overly cultural-inclined mindset pushes us back into a fearful state of inaction, of living by the creations of others and their imposing worldviews — thus limiting even the belief of starting one’s own journey of creativity and understanding. What this state of inaction really fears is the rejection, ridicule (ie. being called crazy) and disappointment we might face when expressing our unique selves. But in the venture world nonetheless, crazy is good, different is good, unrealistic is good. If one is “blending in” too much, they risk to take part of the status quo and not change anything. The ideal entrepreneur is not afraid of taking his/her unique weirdness to the extreme. In fact, having non-consensus and unique insights to the world is the first step to building a successful and startup, because “If something is already consensus then money will have already flooded in and the profit opportunity is gone”, as Marc Andreessen notes. Thus, an entrepreneur must really his/herself ask what their distinct voice is, and what unimitable potential that they can bring into the world is, in a way where their inner nature intersects with the world’s nature.

“From the immanent direction of nature’s total evolution there may be elicited a destination of man by whose terms the person, in the act of fulfilling himself, would at the same time realize a concern of universal substance. Hence would result a principle of ethics which is ultimately grounded neither in the autonomy of the self nor in the needs of the community, but in an objective assignment by the nature of things.” — Hans Jonas

Our individualistic subjective experience can be flicked by the individual him/herself to comprehend the interdependence and cooperation in life’s ecosystems. This is definitely hard to notice when one is led by the ego, but it’s there all around us if one learns to look. There is an opportunity for self-actualization to melt into self-transcendence. Such ecological thinking requires getting to a balance, even a superposition, between individual freedom and care for all society, and between personal identity and social coherence — as Murray Bookchin has alluded to. Coherence, as Jordan Hall, describes, is about “entering into a relationship where the whole is simultaneously much more than the sum of the individuals and the individuals are much more themselves for being part of the whole”. In this case, the “I” isn’t separate from the world, but only exists in relation to how it is manifesting in the world, especially when the world is better because there’s this I in it. As Bookchin explains, there is a “logic of unity between the ‘I’ and the ‘other’ that recognizes the stabilizing and integrative function of diversity…Initially, to be sure, it is formed by a continuation of nature’s cooperative and associative tendencies into the individual’s personal life.” To have an individual purpose, such as wealth and self-expression, driving your actions does not retract from with loving all people and life, because the purpose is to simply help them — the mission you carry forward is for them. This kind of win-win mentality, because that’s how you add value to others on your journey.

“Only by cultivating our individuality, can we strengthen the tie which binds every individual to the race, by making the race infinitely better worth belonging to” — John Stewart Mill

The concept of the supermind is also interesting in a way that links up the personal human mind with the higher universal mind, that which regulates the complexity and relationships found in the natural world. We can hence assume that there is this inner immaterial essence, previously called the “soul” by religions, and that it deeply connects the inner meaningful self with the universal oneness outside of bodily existence that created the natural world. Only with this kind of non-dual spirituality can one actualize the self and help it transcend from personal meaning into synergy with the collective consciousness. This sense of connectedness helps is that all life opens up to intuition, because one becomes completely “tapped in”, operating from the supermind, and pulled forward by the universe. When that happens, the person, in this sense becoming a “conduit” of intelligence and creativity, will feel like the universe is really supporting one’s higher purpose by throwing opportunities in the way and clearing the roadblocks ahead. They will start seeing synchronicity everywhere. As Vishen Lakhiani, speaker and founder of Mindvalley, “You have these little intuitive nudges, you might be waking up in the morning and boom with the idea for that next blog post and the idea for that next product”. Those thoughts will turn into realities significantly faster, and everything seems to be unfolding into the next moment where you’re one step closer to the end.

“Supermind is the epitome of freedom and responsibility. You, and in the deepest sense you alone, become responsible for the entire planet and all of its beings. Immanuel Kant beautifully defined a “cosmopolitan” as one who feels that, “when anyone anywhere suffers, I suffer” — a profound world-centric awareness. And the ultimate cosmopolitanism is when one feels that, when anyone or anything anywhere suffers, I suffer, because I am them.” — Ken Wilber

“Within [the holistic and systems-thinking paradigm], the ultimate sources of knowledge seem to derive not from elementary component parts, but instead from reference to the systems broader context. Given that something can only be properly understood within this context, to gain a fuller understanding of something requires gaining a greater understanding of the environment or context to that system.” — ‘Holism & Reductionism’ video, The open and collaborative ‘Systems Innovation’ platform

The main challenge for innovators in modern society is that we have reached a certain scale of complexity that requires them to think at a systemic level. It is apparent in universal issues such as global trade wars, climate change, the monetary system, healthcare supply and other fields that span across the global complex system: people don’t always have the ability to grasp the whole, and they rarely look at systemic consequences of their actions, which got us into the troubles we are in today. If certainty is dead and complexity rules, then it is only entrepreneurs who can thrive in this kind of environment who will be able to create something new and accrue value. Wisdom, as I define it here, is the ability of an entrepreneur to really understand the world and act upon it to create new realities. In the sensemaking part of their job, an entrepreneur cannot escape the journey to seek wisdom, because they have to be, to a large extent, right in their understanding in order to be successful. The most important tool for the modern entrepreneur is the ability, on one hand, to make sense of the different nonlinear causalities leading the problem being solved, on another hand, to be able to understand the potential consquences his/her innovation brings into the larger systems.

Compared with a reductionist method for problem solving, which places emphasis only on elementary parts of a system a limited way, systems-thinking lets go of narrow understanding and monolithic solutions. Systems thinking, we can add, is also a sophisticated method for dealing with the areas within subjective human nature such as psychology, ethnography and sociology — areas which launching innovative products is really reliant on. Instead of focusing only the trees without seeing the whole forest, systems thinking introduces a modern way of understanding problems at the scale of the whole, and of then solving them by participating at the level of the whole. S. Sterling adds, in his elaboration on systems thinking, that through a reductionist thinking method the different domains of knowledge (how we see/feel the world, how we interpret the world, and how we participate in the world) are fragmented and narrowly drawn; whereas through the ecological-systems method they are connected and re-integrated, thus in his words conducive to wisdom. He suggests that those who focus on the three domains alltogether, are relieving the tension between idealism and realism, between philosophy and reason, and between spirituality and practicality.

“We’ve been extremely successful in in manipulating a concrete world with powers of rational thinking and planning and purpose. But now that we’ve reached this point of scale, where it’s our inability to conceive of the whole that that is holding us back that maybe is threatening our way of life. This is where we need to act and be aware of the whole, and so I think it’s integral.” — Ken Wilber, author and founder of Integral Theory

It may also seem today that the more knowledge we gain, the more confused we are. Knowledge acquisition is becoming harder to come about, not only because there is so much complexity that makes it almost impossible to grasp the full context, but also because we have been witnessing for the past two decades an explosion in information (and misinformation), mostly thanks to the internet. This obviously hinders true knowledge acquisition. The de-facto state of the media today is noise over quality. It is mostly salience and availability. There is neither any authenticity nor any reality. Most of it is really just hype, and this is especially true in technology news. We are in an era of non-stop digital distraction and the platforms keep optimizing for hacking attention further and further. The ideal entrepreneur, in reaction to that, keeps themselves sane by making space for your existing thoughts to play out and focuses only on the knowledge that matters for their own journey. They know that not all kinds of knowledge is useful, as Leo Tolstoy noted. They try to continuously understand things in greater depth and — because it’s in those states where the magic of creativity and progress happens.

In an article called ‘both/and’ leadership, Wendy Smith, Marianne Lewis and Michael Tushman argue in the Harvard Business Review that “leaders must go into the job appreciating multiple, often conflicting, truths” and that “they need to be consistently inconsistent and focus on managing that inconsistency.” They also note that “Paradox has long been at the heart of great accomplishments — revealing profound truths and spurring creativity” meanwhile quoting Niels Bohr, Nobel prize-winning physicist, saying “How wonderful that we have met with a paradox. Now we have some hope of making progress.” A large part of systems thinking is hence about thinking in shades of grey, integrating two or more conflicting ideas, embracing two mutually exclusive perspectives and reconciling them in a useful way to solve problems. One must be looking for resolving the paradoxes, instead of landing on an ‘either-or’ solution. The end result may be something completely innovative, and transcending whatever was before it. Josh Wolfe, an investor that likes companies on the sci-fi level and a thinker that I have quoted previously, advises that a true contrarian must take advantage of the volatility between conflicting knowledge, rather than just deciding to pick a side. This is otherwise also called a strategy of leveraging the polarity.

“Opposites can be united only in the form of compromise, or irrationally, some new thing arising between them which, though different from both, yet has the power to take up their energies in equal measure as an expression of both and of neither.” — Carl Gustav Jung, Swiss psychiatrist and psychoanalyst

Now that we’ve covered systemic thinking and wisdom-seeking, I’ll switch to the other polarity, which is “re-learning and “un-learning”. To do that, we must first turn attention to questioning. We’ve already established that entrepreneurship is when the person decides to control the narrative his/herself, and this requires questioning all the dogmas and directions of society. That seems the only way to build the future, as we have seen that most innovations disrupted and disturbed the prevailing thinking of their times. But we’ve also said that the best entrepreneurs have a total belief in the new, and don’t take what culture has taught them as the ultimate truth. This explains the main reason why a “re-learning” mindset is indispensable for creating the future — the past will not work in the future. Creativity is anyway itself to go beyond the accepted consensus, and to transform new connections into new possibilities. Henry David Thoreau famously wrote that “only when we forget what we were taught do we start to have real knowledge.” The philosophy of re-learning includes not listening to industry leaders who succeeded only in the past, and exploring new territories that the experts do not dare to go, and even dare to question themselves if they’ve been at it for quite sometime.

“The important thing is not to stop questioning. Curiosity has its own reason for existing. One cannot help but be in awe when he contemplates the mysteries of eternity, of life, of the marvelous structure of reality. It is enough if one tries merely to comprehend a little of this mystery every day. Never lose a holy curiosity.” — Albert Einstein

In his book “Unlearn”, Barry O’reily makes the case for “un-learning “as a method for reaching breakthroughs. Mark Boncheck explains, in the Harvard Business Review, that un-learning is about letting go of the behaviours and paradigms one has previously learned in their lives or has built his/her career upon. The then replacing them with the newer habits. It gives an entrepreneur the mindset to tackle new problems and win through new business logics. Shunru Suzuki, a Zen Buddhist monk, said that “In the beginner’s mind there are many possibilities, but in the expert’s mind there are few.” The expert’s mind may settle on ideas too hastily and have the illusion of knowledge, but the beginner’s mind embraces novelty, imagination and creative thinking. The constant updating of assumptions as part of re-learning is very relevant to technology entrepreneurship, as it is a similar concept to product experimentation and feedback loops — and may even stem from it. Data signals from small losses or wins, from customer interactions with the product, or from business analytics can really change one’s assumption or view of an issue hand. And as change accelerates, quickly adapting to the uncertainties, by unlearning and relearning, becomes the most necessary skill for creating the future. This belief was also mirrored in Yuval Noah Harari’s advice about constant self-reinvention, which he pointed to as necessary to keep up with the world in 2050.

Emilie Wapnick, who in her TED talk hits the right note talking about being a multipotentialite, a polymath who constantly seeks new experiences and knowledge but gets bored very easily, whose passions start like explosions through which he/she moves quickly one by one. She believes there are people who can’t ever be specialists, and who don’t really have a “one true calling” but many. These generalists, Hanzi Freinacht explains, “take knowledge from one area of life applying it to another, moving back and forth freely between many different areas, between many different paradigms, or, or different inquiries or disciplines.” When the knowledge and expertise of one domain are very disconnected, or even maybe in conflict between each other, the polymath embraces the interdisciplinary “multilemma” and quickly fills up the gap. James Surwillo, in his book on metamodern leadership, proposes that “our next generation will have in their grasp counterintuitive breakthroughs that span the disciplines to enact solutions that seem impossible even by today’s advanced standards.”

This leads us to the ultimate combination of opposites. It’s obviously great that someone has sincere interdisciplinary curiosity and strives to pursue learning as an infinite endeavour of understanding the world further. Yet the apparent trap is this: Pursue too much knowledge without humility, and a person is no more aware of what he/she is unaware of, and is sure he/she doesn’t have to learn anything new. To solve this paradox, Socrates noted that “True wisdom comes to each of us when we realize how little we understand about life, ourselves, and the world around us.” In other words, he described the wise man as one who knows himself to be a fool. The wise man, here, I’m adding is someone who is willing to unlearn the old and relearn the new, to keep up with modernity and rapidly changing times. Therefore, the more knowledge one gains, the less knowledge he/she has, and the more he/she must re-learn. The wise entrepreneur only has loose convictions and follows a pragmatic journey where something previously thought to be true could turn out to be false, and this allows gaining new insights that complete his/her knowledge. The wise entrepreneur also accepts that his/her perspective, or opinion, is only one of many and incorporates other perspectives through multiple framing and integration. They, most importantly, perfect the art of questioning by way of the beginner’s mindset — and that’s the only way innovation functions.

“Part of our emergency is that it’s so tempting… to retreat to narrow arrogance, pre-formed positions, rigid filters, the ‘moral clarity’ of the immature. The alternative is dealing with massive, high entropy amounts of info and ambiguity and conflict and flux; it’s continually discovering new areas of personal ignorance and delusion.” — David Foster Wallace