Ethical Startup Playbook 🌱⚖

This is more of an UNplaybook: Questions > Answers. Suggestions > Commandments. An introduction to a wide range of concepts. An invitation into a journey of unlearning and relearning, imagination and courage.

🎶 Listen to audio version here.

–TABLE OF CONTENTS–

[1] Why does this Matter?
[2] What is Ethics?
[3] Commentary, reflection questions, and resources on the Medium dimension of technology startup development
[4] “ “ on Personal
[5] “ “ on Product
[6] “ “ on Organization
[7] Putting into Practice

Mark Henson: Lost Horizon. Last fall, researchers at the Institute for Multi-Stakeholder Initiative Integrity concluded: “ The most significant and transformative human rights project is one that has received little attention within the human rights domain: challenging the corporation itself and re-imagining our economic enterprises.” I used to ignore these critiques. Then I wanted to burn the system down. Now I have deep appreciation for the paradoxes we get to wrestle with in this time between worlds.

[1] Why Another Playbook? 📚

Every week, another major scandal: Facebook, Ozy, Barstool, and endless stories we don’t hear about because of social pressure and disparagement agreements. “The Startup” has become one of the world’s most influential institutions, producing an outsize impact on the lives of its stakeholders. But its growth-at-all-costs mindset is causing pain and suffering to users (Instagram), workers (Amazon), communities (AirBnB) and the biosphere (Bitcoin). Would different mindsets and culture yield different results?

Meanwhile, nearly half of all American teens think they are going to start a business that will change the world. Woah. What’s the distribution of motivations for these 10 million future business leaders? What playbook are they following? Which role models are they looking to? What questions are they asking? I feel simultaneously nervous about the prospect of an army of Zuck’s, and excited by the potential of this entrepreneurial energy. The stakes are high, but the bar to play is low.

Having 10 years of experience with YC/VC/MBA culture as an employee, founder, and investor, I find myself curious about alternative ways to create and live. To bring more quality of life, meaning, and integrity to the startup process. Not to throw away the fundamentals; but to complement and balance them out, challenge the business-as-usual and education-as-usual status quo (Aristotle believed ethics came down to asking tough questions), and source new ingredients that can nourish healthy soil for Gen Z: innovative accountability practices like the North Star Ethics Pledge, inspiring movements for more ethical and inclusive startup culture like Zebras Unite, and evolutionary economic frameworks like Doughnut Economics (meet the needs of all people within the means of the planet).

Inspired by Donella Meadows’ 12 Leverage Points to Intervene in a System, The Center for Humane Technology developed a simplified framework for the tech industry. When I think of shifting how we approach building startups, I look at the Culture & Paradigm side of the scale, which is the highest leverage point and most difficult to shift, occurring when there is widespread change in our core beliefs, values, behaviors, and operating norms.

This playbook is for folks interested in starting a tech company and wondering how to do that in a more ethical way, given the context of their unique life and our unique times. It’s a small starting place; very far from comprehensive of what I think could be useful: essays for different stages and industries; a multiplicity of books on the topic; a de-accelerator program, a whole school for ethical startup education (DM if interested). It’s what I wish I had read while poking around in the dark building Siempo: an attempt at a “full-stack” ethical startup.

Most entrepreneurs don’t have time to innovate on product and org structure and personal lifestyle. To attempt it all might raise the risk of failure. This piece is meant to relieve some of that tension through curating and translating new concepts, highlighting role models and communities of support, and framing the opportunity in a more inspiring way.

“Without reflection, we go blindly on our way, creating more unintended consequences, and failing to achieve anything useful.”
― Margaret Wheatley

[2] What Is Ethics, Actually? ⚖️

Ethics is one of those words that means different things (or no thing) to different people. It’s often engaged superfluously and shallowly, if at all. Ethics does not have the sexiest reputation. It is at most a minor focus in professional education systems.

I’m still wrapping my head around what it is, how to relate to it, even how to use the word. It’s a gigantic and nuanced topic. My cursory understanding is there are three major areas of study, in descending order from abstract to applied:

• Meta-Ethics — study of the meaning and nature of ethics. // What is goodness?
• Normative Ethics — (aka moral theory) study of ethical action, and what makes actions right or wrong. Includes virtue ethics like Deontology, Stoicism and Hedonism, Consequentialism and Utilitarianism, Judaism and Original Instructions. // What should I do?
• Applied Ethics — application to real-world situations. Bioethics, business ethnics, technology ethics. // How do we fulfill our obligations?

I imagine there’s a word in German for what gets lost when abstract academic ideas are simplified and translated to the business world, moving from Meta to Normative to Applied. We can’t expect our business leaders and politicians to be well versed in such vast and esoteric disciplines. But should we? Plato thought so, arguing for philosopher kings. What’s it going to take to get founders, investors, and other actors in the startup ecosystem to weave ethics and wisdom into their process?

Today’s startup world is rich ground for ethical inquiry, surfacing big questions like what is good for people to produce or consume? According to tech ethics professor Matthew Hastings, to start a business is to make an ethical claim about some product or service being good for people or society. But economic value (i.e. money) alone has become a poor signal for what is good. So who and how do we decide what is good? How can we cohere around shared notions of goodness, and then build good businesses, in a good way?

Popular philosophers in the ethics x technology conversation include Shannon Valor (tech and virtues), Ivan Illich (tools for conviviality), Batya Friedman (value sensitive design). For me, Forrest Landry offers the most inspiring and complete definition and framework, clearly connecting ethics to morality, integrity, justice, knowledge and more (see pg 13–18 of Western Tantra, the updated version of The Effective Choice). Forrest is a living philosopher technologist. A taste (read slowly):

Cool. So it’s about examining how we make choices of what to say and do, and how to improve those choices, for all involved.

Forrest goes on to make a key distinction between Ethics and Morality.

Ethics is not about whether any given choice is ‘right’ or ‘wrong’ (Morality), only about varying degrees of effectiveness and enhancement of life.

Ethics is internal to oneself. Morality is an externally defined set of rules in a particular domain.

To develop the principles of ethics is to determine a method and, therefore, a practice of making maximally effective choices.

What makes an effective choice?

The punchline: “Love is that which enables choice.” Forrest drills down deeper into precise meaning of these key words and the relationship between them.

It’s a lot to take in, but I’ve grown to adore this definition. I think we all know what it feels like to make choices that are out of integrity, less than creative, shying away from fully experiencing something, overly selfless. Forrest expands my calculus of what is worth considering in making a choice, prompting me to think about my relationship to each of these dimensions, which go far beyond the utilitarian, into the really wonderful and even sacred stuff. It provides a compass; but a more fluid one. Not a binary good/bad or effective/ineffective; rather a spectrum, relative to each person.

Reminds me of that advice not to compare yourself to others–only yourself. Or expanded definitions of wealth to include social capital, physical capital, emotional and spiritual capital. The “what is success” pie growing far beyond the single, double or triple bottom line; it actually never ends because nth order outcomes are never fully known, always yet to be revealed. That beyond our primitive ideas of “good” and “bad” are universal truths, paradoxes and mysteries that we can learn and dance with.

Please let me know where my interpretation may be off the mark here. In dipping my toes into the field, I’m struck by how many different dimensions exist to think about what ethics is and how to apply it; how many (myself included) virtue signal ethics without depth of understanding or walking the talk (good washing, hypocrisy, self-righteousness); how every one has their own ethics but varies widely in awareness of how they are making choices; how most sets of ethical principles only negatively specify what characterizes effective choices (what not to choose), vs. describing what or how to choose.

What principles might empower more effective choices for tomorrow’s entrepreneurs?

Heart and Mind

Applying Ethics to Startups

What I want is a playbook for this moment, translated into accessible language that I can peg my process to, walk founders and teams through, shout from SoMa rooftops. A thorough, relevant, and practical principles of startup ethics available for current and aspiring leaders to study and apply, now. Courses, tool kits, shared language. That has yet to cross my desk (please share if you’ve come across or are working on something like it!). The existing playbooks seem silo’d across the different chapters that I dive into below. What would such a comprehensive method and practice look like? Is it even possible today with so many components of startup culture antithetical to ethics?

To be clear, this playbook is not that. I’m not a philosopher or ethicist capable of articulating such a coherent body of work. I’m acting as a curator, weaving together concepts and resources into a digestible format that temporarily fills what I perceive as an awareness gap in the communities I’m connected to. Besides, is writing a new playbook missing the point, since to create a new orthodoxy would be to take a moral stand on the existing paradigm, and potentially reproduce the same problems we are seeking to transcend? Hence the attempt at an UNplaybook orientation here. Although I have lots of thoughts and feelings around the shortcomings of startup culture, my intention is not to take a moral stance on what one should or shouldn’t do; rather to echo that:

At all times there exists an invitation for each of us to make more effective choices in all domains of all worlds we are part of.

I’m also tickled by the branding challenge. How might ethics be rebranded to communicate its hyper-relevance in this historical moment? To attract the authentic interest of the next generation? What kind of startups might those 10 million kids build if the playbook involved taking digital detoxes to connect with their heart and soul, sense of purpose, the big questions echoing through time, emerging economic models, re-enchantment of nature, and healthier interpersonal connection? What if the narrative shifted from how to not fuck up big time to how to make more awesome choices for all involved?

My intention is to add some texture to the ethical startup inquiry based on my experiences and studies, especially for those at the idea stage when each choice has a sizable influence on what unfolds. Close to conception is a critical time to start engaging ethics, as opposed to when something goes wrong at scale.

There are many ways to slice it, but I find it helpful to think about how when we come up with an idea for a new product or service, we are simultaneously:

• Selecting a Medium
• Creating a Lifestyle
• Developing a Product/Service
• Building an Organization

What kinds of questions, frameworks, stories and tools might empower us to make more effective choices in each dimension?

“The ultimate, hidden truth of the world is that it is something we make, and could just as easily make differently.” — David Graeber

Raphael, “School of Athens” (detail of Plato and Aristotle), 1509–1511. Stanza della Segnatura, Palazzi Pontifici, Vatican.

[3] MEDIUM: The Medium Is The Message 🎨

The conventional startup playbook is a monoculture of Delaware C Corp entity, venture capital financing, dual-class stock structure, and so on. It’s one framework that engenders a particular type of culture, lifestyles, needs and accountabilities. Some might say a message to “grow at all costs” and “consolidate ownership and control to few” and “cut ethical corners to get the job done.” A system that often celebrates ineffective choices. That works for shareholders (owners), but doesn’t always work well for all stakeholders (those impacted by the company’s decisions).

Is this the only way? What else is out there? As the institution of business adapts to a rapidly changing world, my guess is there’s going to be greater awareness of the full menu of choices that a founder has when bringing an idea into the world, and a Cambrian Explosion of innovation on that menu, trending towards greater alignment with the well being of all agents in the system. From Public Benefit Corporations to Decentralized Autonomous Organizations, founders may be empowered to make more effective choices on the medium with which they want to express their ideas and values into reality.

We get to re-imagine everything. It’s a time for experimentation, new stories, communities of practice. This is certainly not the path of least resistance (at least not initially). But it’s precisely friction that can support founders in slowing down and making different choices that realize the desires of all impacted by that choice (aka “win-for-all” or “omni-considerate”). Multi-stakeholder co-op evangelist Austin Robey offers the following:

How To Start A Co-Op. Taking the road less traveled isn’t easy. But that’s the invitation.

Three sub-dimensions to highlight here are Ownership, Capital, and Governance. What one chooses creates the conditions for what can emerge. Scratching the surface:

Ownership

Are there ownership structures that more equitably acknowledge the contributions of all those working on the mission? The core function of a cooperative (a long standing alternative to the corporation, that is recently growing in popularity) is to democratize ownership and control. It’s a collectively owned enterprise that can serve the interests of all stakeholders, from investors to workers to customers. Start.coop is the YC of co-ops, now offering a free Lean Co-Op intro course.

Regardless of the corporate structure, companies are finding creative ways to bend the traditional rules of ownership, e.g. Eileen Fisher’s progressive employee stock ownership plan that gives employees 40% ownership of the organization, and Sharetribe’s “steward-ownership” model that assigns special rights to an outside non-profit foundation tasked with preserving its social mission. Instead of getting acquired or going public, Exit to Community pathways are being paved for startups to become owned and controlled by users, workers, and stakeholders who value and depend on the company. Jason Wiener and Nathan Schneider are your legal and academic guys, respectively, on alternative ownership.

Capital

Whenever you are thinking about taking outside investment, it’s important to consider the intention behind it. What return targets are you signing up to deliver on? How might this capital constrain or support ethical choices? Where is the capital coming from upstream? How do the values of GPs/LPs align with yours? In choosing a boss for yourself and your team, who do you want to labor and make money for?

While it may seem like everybody is living their best life raising venture capital, it’s actually less than 1% of new businesses that take this form of capital designed for rapid scale, and there is a growing ecosystem of alternative capital options that have longer time horizons, lower return targets, and greater ability to center ethics in decision making. VC’s know what’s up–”rocket fuel” isn’t for everyone. The model has it flaws. But there’s enough cultural enthusiasm to keep the rocket ships launching.

Don’t forget about bootstrapping — selling consulting services for non-dilutive funding is a tried and true way to simultaneously become an expert in your domain, while validating the market for your concept. Considered Capital is one of many organizations that help businesses find alternative funding that aligns with their values. Jen van der Meer teaches alternative strategies at Parsons and The New School, with Reason Street helping organizations transition their business model and financing model.

Even within venture, things are changing. Adrian Grenier and Bá Minuzzi’s DuContra Ventures is adjusting carried interest (the return that goes to investors in the fund) to be more equitably distributed across stakeholders, enabling them to experiment with valuing the many immeasurable ways community members contribute, which they refer to as “Yield Beyond Money.”

By Rob Tashima (Village Capital), with Astrid Scholz (Zebras Unite)

Governance

Hierarchy is dead. Long live hierarchy! Who gets to make choices about what? Too many organizations and communities adopt default governance practices that rely on the unchecked authority of founders. Governance can be a highly charged matter. The answer may be something that integrates the strengths and accounts for the weaknesses of both hierarchical organizations and non-hierarchical organizations, to form more organic systems of collective decision making.

Holacracy and Sociocracy are progressive governance systems that replace conventional management hierarchy with a concrete framework for encoding autonomy, agility, and purpose-alignment into an organization’s DNA. I’ve found the learning curve to be steep, but a gamekeeper once folks gets the hang of it. Like ethics, alternative governance is easier to integrate from the beginning, as opposed to adopting later on as a fix once company DNA has calcified. See CommunityRule for a range of other governance structures, and The Metagovernance Project for the bleeding edge of R&D in online governance.

While I still don’t really understand crypto (keep trying to web3-pill me!), and feel mixed about the environmental impact, criminal behavior, and lightening rod for scammers, finance bros, speculators (✋🏼) and hoarders… I also don’t live under a rock and can see a ton of values-centric innovation happening in the Web3/NFT/DAO space. People finding creative ways to align incentives that make systems work in a more harmonious fashion. I’ve had my own hangups and resistance to blockchain evangelism, but I can’t deny my appreciation for digital infrastructure that acknowledges subtle interactions in networks, creates more fluidity and possibility in how humans exchange value, + the privacy and trust things.

There is no singular ethical or right way to start a business. There are only degrees of effectiveness relative to your unique context.

Reflection Questions

• Medium— Every idea is not a C Corp. What are the different forms/mediums your idea could be expressed through? Are you sure it’s startup? Perhaps it isn’t a technology business, but a nonprofit, an essay, a direct action, a policy template, a one time IRL experiment, just a joyful dream, or nothing at all. Consider the impact of Banksy’s art or Greta’s voice. How do your life experiences and motivations bias you towards the medium you currently envision? What are the tradeoffs?
• Lack Creates Longing— How have you felt impacted by the current paradigm of startup culture? What alternatives exist for those pain points? Who in your network might be able to support you in exploring your options?
• Life Alignment— Do the ownership, capital, and governance structures you have or desire support or inhibit the lifestyle you want for yourself and employees? Does starting a business in general support or inhibit it? Are you sure you want to be a founder, or are you more of an artist, activist, or a weird-trepreneur? If founder, are you more of a swing-for-the-fences or get-on-base kind of person?

Android Jones: Chrysalis

[4] PERSONAL: Who Do You Need & Want to Become? 🐣

And then there’s YOU! Before there was an idea, there was you, the beautiful and messy human filled with innocent hopes and noble dreams, crippling fears and unconscious biases, hungry ghosts and unprocessed trauma. You could not have possibly earned a PhD in systems change, become an expert in facilitating nuanced conversations about race, and meditated for 10,000 hours; all while supporting yourself financially. You are doing the best you can with what you got. We all talked about it and we think you are doing a great job 😹

Being that this is so, what life path might mitigate the ugly stuff that will naturally get expressed in your product and organization, while maximizing your ability to make more effective choices?

“Ineffective actions and choices result from a lack of clarity between the soul and the mind. To have a lack of clarity is to have a lack of knowing and of understanding; it is an absence of wisdom.” — Forrest Landry

Three relevant sub-dimensions here: Continuing Education, Personal Growth, and Lifestyle.

Continuing Education

Whether we’re aware of it or not, we are all lifelong learners, constantly taking in information, making meaning of it, and applying it. I believe that for each of us there exists a gap between where we are now, and where we need to be in order to create and live more effectively. Why not identify that gap and take closing it seriously (any playfully)? And then coordinate studies and practices to support those long-term learning goals. Especially around alternative approaches to entrepreneurship.

“When social systems are in periods of rapid transformation, the role of schools becomes contradictory. They teach knowledge that is no longer relevant, socialize people into roles that no longer exist, and provide mindsets needed to continue ways of life that are disappearing.”–Zak Stein

What and how should the next generation of founders learn? is one of the most important meta-questions I can think of. It’s possible that much of what we learned to date is irrelevant, ineffective, and will need to be relearned. Here’s a table of questions and topics that feel relevant to the founder journey, and may be taught in tomorrow’s business school:

One way to reveal what may be on your Learning Journey is to list out each of the key topics (third column) and check off which ones you feel deficient in or curious about. Think about who in your network might be able to support you in that. When recruiting, consider experience in these domains to be key value adds.

Personal Growth

Hand in hand with lifelong learning is personal growth. There’s a whole industry of executive coaching and professional development programs of various shapes and sizes, operating at the very limits of what the market will bear in terms of quality and ethics. Business schools are starting to toss in some mindfulness and emotional intelligence, accelerators pay lip service to the importance of mental health, and some “conscious” investors are boasting coaching support as their secret sauce.

Whatever the doorway(s), philosophers and ethicists throughout the ages believe it’s important to make an effort to know thyself. Sounds reasonable. By working on oneself, one may discover how trauma shapes their sense making and choice making, the nuances of how their personality type plays better or worse with others, and that intuition and emotions can be a form of ethical intelligence. And perhaps most importantly for founders: how to manage stress, regulate one’s nervous system, and find balance when things get imbalanced.

Watch out from personal experience: careful of getting caught in the clouds, stuck naval gazing, or catching Silicon Valley Savior Virus. Go easy on the peak experiences. There’s a whole ecosystem of communities that think that tech x awakening will save the world, and it’s easy to be thrown off balance into the 🐰🕳’s of personal development, leadership, productivity and spiritual communities. Find the balance. Consider finding a therapist or working with a coach. I’ve found a lot of grounding in reconnecting with the tradition of my ancestors. Jamie Wheal’s open source operating system for transformative culture feels good. Slow down (can’t say it enough). Integrate. Integrate. Integrate.

Have patience. It takes time to understand what we’re filled with, what motivates us at the individual level, and how we actually want to live. Understanding personal choice architecture and improving it is essential to meet the complexity of our times. Einstein famously said that no problem can be solved at the same level of consciousness that created it. I’d offer that no problem can be solved without a deep understanding of the consciousness that created it, and how that is still operating inside the problem solver. As above, so below. As within, so without.

Ethical entrepreneurship inevitably becomes a spiritual practice, with lifestyle, product and org acting as mirrors to reveal that which is invisible and out of alignment inside oneself. The dojo is open for practice Monday through Friday.

9 out of 10 startups fail. Might as well learn something along the way. Which practices feel most interesting to you? Source: The Center for Contemplative Mind in Society

Lifestyle

Every morning you wake up and allocate your finite life force to a set of activities and relationships, based on obligations, needs, curiosities and abilities. There are many ways to live. Of all creative possibilities available in this reality, how would you like to spend your day?

It has been said that the tech entrepreneur is the new rock star. But neither lifestyle is always as pretty as it’s made out to be. Most CEO’s have a secret desire to leave. Often mental health takes a massive hit, with founders twice as likely to suffer from depression, suicidal thoughts and have psychiatric hospitalization, 3x more likely to suffer substance abuse, 6x more likely to suffer from ADHD, and 10x times more likely to suffer from bi-polar disorder. Not to mention physical health challenges, strained relationships, and loneliness. Hyper focus on de-risking personal financial payout can come at a price of quality and richness of life. Founders have been hearing this warning for years. Unfortunately, we get so blinded by the light of Silicon Valley success propaganda, that we don’t really get the message until we’re neck deep in it. Given the state of your mental health, would your doctor recommend entrepreneurship?

Are you comfortable committing the next 5, 10, 20 years to a lifestyle that features the aforementioned risks? Check in with yourself and the relationships that are most at risk of being destabilized from a more demanding schedule, or an abrupt rise into power, wealth, or recognition. Consider what a “good life” looks like for you (not your parents or friends or societal expectations).

No need to beat around the bush… and then there’s the money thing. It’s certainly a matter of privilege to have time to think about and experiment with ethics. Having access to generational wealth affords one the ability to take greater economic and social risks: whether speaking out against unethical behavior within an organization, pursuing a path of ethical entrepreneurship, or taking a chance on an underestimated founder with an alternative economic model. If this is you, how can you leverage your position in the web of life to try and role model and empower different paths for the next generation?

Regardless of socioeconomic position, what’s enough, for you? What might you actually do with $1M, $10M, $100M, $1B? What is it in service of? Keeping in mind that happiness tapers off at 100k/year, and excess wealth doesn’t necessarily solve our problems (mo money…)

I don’t know who needs to hear this, but:

You do not need to start a company. You are not your job, your achievements, your net worth. You are enough. You don’t have to do anything.

I appreciate the Wheel of Life as a reflection tool for getting a quick snapshot of the health of your life, and feeling into next steps in each domain. For a much deeper, embodied, and culturally relevant version of this exercise, check out friend and teacher Sara Wolcott’s Circular Time exercise. What’s out of balance in your life?

Reflection Questions

• Learning— Who are you? What are your ethics? See Forrest’s Questions of Self Reflection. What’s in your Learning Journey? In what ways are you prepared to steward an idea and a team around it? In what was are you not prepared? Why shouldn’t you start a company? What needs cleaning up in your life? What learnings from past projects do you want to keep in mind as you begin this new one? Are there patterns of behavior you would like to avoid? If you could download skills like Neo in the Matrix, which three would you learn today?
• Purpose— How do you think about purpose? What do you think your purpose is now? How has that evolved over time? Are you sure that’s your purpose, or are you grabbing onto something because of pressure to find one? How does your startup idea relate to your Ikigai? How does it relate to your positioning in the web of life? Is now the right time? What is really driving you? Where are your goals the result of compensations to old wounds? What are your ultimate desires? How can you best serve your community in these destabalizing times?
• Lifestyle— Describe your “perfect day” 5 years from now. Can you live that way today? What do you need in order to? What are you willing to give up in order to get there? What are you not willing to give up? How will starting a business support or constrain your goals? See Lifestyle Design — Designing Your Life.

Android Jones: Manifest Alpha

[5] PRODUCT: Stewarding Something Beautiful🌱

I’ll keep this one shorter — product is the dimension that has received the most ethics-related spotlight in recent years, as the real and potential harms of technology have been revealed across AI, social media, biotech and more through the likes of the Facebook Files and The Social Dilemma documentary. In the age of exponential tech, consequences show up faster than we can remediate them.

While we can never fully predict the impact of introducing a new agent into a system, how can we make more effective choices around what to build and how to build it? We might practice creating negative design personas, brainstorming how the product might generate negative externalities, and then adjusting our strategy accordingly. Even though our financial and legal systems don’t require us to take such actions, what might stakeholders stand to gain from the process?

This “slow down and ask questions” ethos is anathema to the “move fast and break things” posture that led companies like Facebook and Uber to the stratosphere, albeit not without lots of collateral damage along the way. Is there a responsibility for startups to self-regulate?

Product is inextricably linked to business model. As the engagement-reliant advertising model falls out of style, how can we get creative in experimenting with new business models that are more aligned with the users’ best interests? Less addicting. More accessible. Less manipulative. More transparent. Less objectifying. More dignifying. See Flourishing Business Canvas for inspiration.

Instead of focusing only on what would be most profitable or popular, what might we create if we also asked:

What makes life beautiful? What is worthwhile? What is good? What brings a sense of depth to our existence?

Omidyar Network’s Ethical OS Toolkit and Checklist — a guide to anticipating the future impact of today’s technology. Also check out the Consequence Scanning Toolkit, Ethical Explorer Pack, Agile Threat Modeling, The Tarot Cards of Tech, & Data Ethics Canvas.

Many organizations and tools have emerged to meet this moment on the product development and design side:

• All Tech Is Human —building the Responsible Tech pipeline: making it more diverse, multidisciplinary, and aligned with the public interest. See their Responsible Tech Playbook, Ethical Tech Report, and list of Supplemental Works.
• The Center for Humane Technology — dedicated to radically re-imagining our digital infrastructure. They just launched a Fundamentals of Humane Technology Course to educate technologists in principles including:

Obsess over values, instead of engagement metrics

Strengthen existing brilliance, instead of assuming more technology is always the answer

Make the invisible visceral, instead of assuming harms are edge cases

Enable wise choices, instead of assuming more choice is always better

Nurture mindfulness, instead of vying for attention

Bind growth with responsibility, instead of simply maximizing growth

• Design Justice Principles—centers people who are normally marginalized by design, and uses collaborative, creative practices to address the deepest challenges marginalized communities face. Other design initiatives include Designing Mindfulness, The Designers Accord, Circular Design, and Inclusive Design.
• Danish Design Centre — The Digital Ethics Compass is a tool to help companies make the right design ethics decisions. Playbook here.
• Tech Ethics for Start-Ups and SMEs’ booklet — practical booklet to help startups and SMEs explore hidden commercial risks and trigger better innovations through the integration of tech ethics.
• Values-Based Social Design —learn to create tech products that tie society together, instead of breaking it apart.

What does Life on Earth want the next generation of founders to consider when birthing something new into the world?

Reflection Questions

• Scale — Imagine your product at the scale of 1 billion people. What are all the things that could go wrong? Is there anything in your solution that makes you uncomfortable? Could your solution be a part of an episode in Black Mirror?
• Existence — Should your idea exist, period? What arguments would a strong opponent of your solution bring forward? How does your idea connect to any of the UN SDG’s or existential challenges of our time? How will you feel about your grandchildren knowing that in 2022, you decided to pour your energy into this idea?
• Lineage — What has humankind learned about this idea space throughout history? Who are the wisdom keepers there? What do they know? Who has been impacted in this space in the past, and how? What values are you embedding into this product? How can your product emulate the models, systems, and elements of nature (biomimicry)?

Android Jones: HanaHaus Mural

[6] ORG: Creating Cultures Worthy of the Human Spirit 👷🏽‍♀️

Last but certainly not least is organizational development, perhaps the dimension that startup founders are most deficient in, and lately quite a minefield. How to engage people in a remote-first environment? What is the role of politics in the workplace? How to create a culture awesome enough to weather The Great Resignation? How to build coherence when everybody is popping different color pills? What are organizations there for, and not there for?

It turns out the top drivers of employee experience are trust, transparency, and psychological safety. And no surprise: diversity leads to more ethical decision-making. What might it feel like to work with a startup that moves at the speed of trust, centers societal considerations, and weeds out employees who do not embrace the organization’s ethics?

The growth edge for organizational leaders is to take into consideration the realization of the ultimate desires of all that are affected by a particular choice.

I thought I was fairly attuned to subtleties of organizational dynamics, but through supporting my friend and teacher Simon Mont’s forthcoming book on the topic, I’m struck by how many considerations go into building just, joyful, and effective organizations. Power. Accountability. Agency. Inclusion. Identity. Process. Belonging. Healing. Emergence. Culture. Facilitation. Conflict. Compensation. Delegation. Change. Dignity. Trust. Toxicity. Patterns. Communication. Authenticity. Systems. Humanization. Dehumanization. Relational dynamics.

According to professor Noam Wasserman at Harvard Business School, 65% of failed start-ups fail for avoidable reasons like co-founder conflict and other people problems. How can founders get ahead of the curve here? 15 Commitments of Conscious Leadership is my favorite leadership book for the moment; Culture Amp provides employee engagement tools and insights needed to build a healthy culture; Harmonize helps align governance, operations, strategy, culture, and values to unlock a team’s full potential; and JumpScale provides culturally relevant organizational wellbeing services.

Indicators of Wellbeing that JumpScale analyzes in developing a treatment plan.

Josh Bersin: As the pandemic continues and competition for talent heats up, becoming a Healthy Organization is more important than ever. Everyone wins when employees feel healthy, empowered, and recognized.

Inspired by Ken Wilbur’s Integral Theory, Frederic Laloux in Reinventing Organizations posits that as humans have evolved states of consciousness throughout history, they have developed organizational models to coincide. And that what is emerging is the “Teal” organization built on pillars of wholeness, self-management, and evolutionary purpose.

“In organizations, real power and energy is generated through relationships. The patterns of relationships and the capacities to form them are more important than tasks, functions, roles, and positions.”
― Margaret Wheatley

Reflection Questions

• Role — How do you most want to contribute to this vision? Which aspects of the process are most nourishing and interesting to you? Is there another team already working in this zone that you could collaborate with? If you’re not interested in engaging with all these org dev dimensions, maybe a CEO position isn’t for you?
• Blind Spots — Which aspects of org dev are you hesitant to learn or engage with? Why do you think that is? Where is your success occurring at the expense of others? Where is credit seeking or image management influencing how you are choosing? Where are you acting out of reaction, habit, or unconsciousness? Where / when / how do you allow fear to influence your choices?

Sam Brown: Plaza Blanca Spiral

[7] PRACTICE: Walking The Talk 👠

How to put this exhaustive amount of new material into practice? Slowly and consistently. Like doing yoga or playing guitar, it requires practice, community, and ritual. It’s one thing to know something in your head; another to know it in your body, such that it becomes second nature. One thing to do a team workshop every now and then; another to integrate ethics into the natural rhythms of the organization. The complexity and breadth of considerations most enterprises face today means that to seriously integrate ethics would require making it a consistent organizational focus, rather than a one-off initiative or list of principles posted on a wall.

Practically speaking, The Startups & Society Initiative’s Ethical Tech Self-Evaluation promotes practices such as:

• Engage a third party to conduct an ethical review of your product
• Hold regular meetings to try to anticipate and manage harms that your product or business might cause
• Hold trainings in ethical risk
• Tie employee compensation to ethical or social good metrics
• Have at least one board member (ideally an independent voice) or an advisor with expertise in ethics. Permission and empower them to regularly check in, voice concerns, and hold you accountable.
• Build a team (and/or cap table) > 50% women, POC, or LGBTQ+

Operationalizing Responsible tech — from Responsible Tech Playbook

Maya Health and Consilience Project exemplify organizations that have prioritized these practices far beyond virtue signaling, centering ethics in key internal and external documents from business plan to mission statement. Making a public-facing ethics pledge creates a level of accountability to actually honor one’s commitments. Making it a seasonal ritual to sit down as a team and check in with those commitments adds another level to make sure it happens on a consistent basis.

The ancients understood this well. Thinking of texts like the Torah that serve as teaching tools that are ritually engaged with, in community, on a regular cycle (daily, weekly, lunar, solar, lifetime), I wonder what it would look like to create a set of teaching stories that cover an array of important aspects of the entrepreneurship process, inner and outer? Here and Now Studios offers two powerful stories for the psychedelics movement in We Shall Call It Pala and In The Light of Dying Stars. How can we create rituals in time to support our ethical intentions?

Consider aligning with the seasons. Winter is a time for slowing down and shedding, spring for budding, summer expansion, fall harvesting. If you have an idea percolating, perhaps you could carve out time this winter to recharge and connect with some of the ethical questions posed here [centering], start prototyping in the spring [vision], launching in the summer [action], servicing in the fall [support], then slowing down again over the winter to reflect on the cycle and what you want to shift in the next one. Looking for a supportive space to get started? Check out the upcoming Hestia Winter Incubator (I’m an alum and mentor!) to ground your creative vision in ethics, healing, and nature.

Finally, consider the overall alignment between your health, the health of your team, the health of your organization, and the health of the broader ecosystem it’s embedded in. Aligned incentives create the conditions for thriving, resilience, and harmony between all levels. Fitting into nature, instead of going against it.

Interested in participating in this conversation about alternative startup culture? I am a proud member of Zebras Unite: a founder-led, cooperatively owned movement creating the culture, capital & community for the next economy. This is where I find the most innovative energy swirling. Zebras (distinct from unicorns) are real, mutualistic, profitable and impactful, sustainable. Start with the manifestos.

🎷 Outro

“There is an urgent need to make ethics more central to our lives, and allow it to be more attractive. As important as offering mindfulness to the world.” — Rob Burbea, Ethics Series

One of my favorite things about ethics is that it’s a never ending exploration; a conversation across millennia that touches on some of the biggest questions imaginable, that in turn shape the trajectory of society. We have much to learn from those who came before us, and we get to co-create what happens next, without attachment to being right or having the final world.

The path of the ethical startup is a beautiful one not only for creating a significant differentiator in today’s startup landscape, but also providing meaning in a culture that has become rather meaningless. A context to connect with greater purpose, self learning, world learning, health, wisdom, community, service, maturation. Maybe some of the ineffable. Maybe even more wealth.

I can vouch. Ethical technology has been my greatest teacher. Permissioning me to enroll in a perpetual school of life. A priceless investment in self and whole that keeps compounding in unexpected ways. While my startup Siempo wrestled with these ethical startup paradoxes (aligned capital? aligned business model? how much self-work?) and didn’t “make it” in the traditional sense, I’m proud of the choices I did make, including the hardest one just days before closing what would have been our next financing round: to put down my sword, having realized that taking money from friends/family and soldiering onwards as CEO for the next X years would be a violation of my personal integrity. I chose the path that allowed me the greatest freedom to make additional future choices for myself and others. And now here we are: I’ve been able to slow down, integrate those experiences, and share learnings with you.

Remember all those kids that have the drive to start a game changing business? What if they were empowered with ethical mindsets and tools to pursue long-term paths of sufficient financial sovereignty, through starting a planetary-crisis relevant business connected to their Ikigai, that becomes their greatest teacher and spiritual journey, that can proliferate and have a multidimensional impact without centralized scale?

From “grow at all costs” to “unfold more awesomely for all involved.”

We are crafting the new economy and future of society with each new business. This is our growth edge. May we choose wisely. May the highest good be revealed.

Michael Divine–Apotheosis

✅ If You Appreciate These Words

• Discuss with your co-founders, team, class or community. Share on tech/business Slacks, Discords, and other social channels.
• Join an intimate Community of Practice of idea stage founders diving deeper into each of the themes in the Ethical Startup Playbook. Six bi-weekly sessions + coaching support, starting in January 2022.
• Engage me through coaching, consulting, or facilitation. My dream is to become an Ethics Advisor or Chief Ethics Officer for multiple founders/organizations I feel really connected to, being that voice of ethics in the room as they grow.
• Approach me with feedback, reading recommendations, introductions to those who may help me further my studies and work (andrewmurraydunn at gmail).
• Consider returning the gift if you feel like you received substantial value from reading this writing (Venmo: @andrew-dunn)
• Help me take the playbook to the next level through offering editing, design, research, and marketing support. There is a powerful book wanting to be written here.

Thank you for your time, attention, trust and hope!

Andrew Dunn’s mission is integrate ethics and eros into life and business. He hangs around NY, CA, and beyond.

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He has been terminated by and quit startups for ethical tensions, co-founded award-winning Siempo: an attempt at a “full-stack” ethical startup (Public Benefit Corporation, open source, equity crowdfunding), written extensively on related topics, and currently advises early stage founders and teams on ethical entrepreneurship and living.

Acknowledgements

• Thank you to the following friends who reviewed and shared feedback: Dr. Wilneida Negrón, Matthew Hastings, Mara Zepeda, Jeff Pawlak, Jared Kasner, Kanupria Sanu, Daniel Roth, Arian Razzaghi
• This piece was developed in dialogue with an early stage startup called Autopilot as part of an ethics consulting engagement, furthered through participation in the October FutureProof Tech Summit, and finished in time for a Wharton Expert In Residence conversation with Zebras Unite co-founder Mara Zepeda and undergrad/MBA students.
• Many of the organizations referenced are ones I am involved with to some extent. I would be thrilled to learn about other relevant individuals and organizations. Please let me know who you’re tracking and I will consider adding them!
• Disclaimer: The materials here are for informational purposes only and not for the purpose of providing legal advice etc etc. You should contact your attorney to obtain advice with respect to any particular question or challenge.