Why a Playbook?

[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 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 (Public Benefit Corporation, open source, equity crowdfunding).

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