Between January 2018 and December 2022, I was the Co-Founder & CEO of Sapien. The Sapien project began as a side project to fix what was broken in online social networking and ended as one of the first startup society experiments. On the journey I learned a lot. Here are 46 lessons from the journey, organized by category:
Table of Contents
Leadership
1. Startups enable you to consciously express your purpose, your values, and your vision for the world. But even more importantly, they are a rich vehicle to continually challenge yourself and undergo necessary transformations.
2. You are not your startup but your startup is a reflection of you. Operate with integrity, intention, and professionalism.
3. Contrary to what others think, your ego is a good thing. Find a way to integrate it with others to collectively elevate your tribe to the highest level of understanding and execution.
4. If you're working on a branding workshop, compliance frameworks, design system, financial projections, external accounting, or OKRs prior to product-market fit; stop.
5. If you only follow the crowd, you will not innovate. If you only think from first principles, you will be oblivious to collective ingenuity. Balance both to escape the cave of ignorance.
6. Be cognizant and recognize the things not in your control, namely timing, entropy of relationships, and the market. Keep a mental (ideally physical!) billboard of knowns and unknowns.
7. Leadership is required to make decisions in uncertainties. Being just and wise requires you to listen and to broaden your perspective before coming to a decision.
8. On making decisions, more often than not, the right brain already knows the right course of action and the left brain will justify it through language and explicit reasoning. While this is fine, try to illuminate any cognitive biases in your process.
Teams
9. Keep your team as small as possible without spreading unreasonably thin or sacrificing mental health. Most additions are linear value-adds but exponential interpersonal scaffolding.
10. Your team makes or breaks you at every point in the journey. Continue to level up yourself and others at every opportunity you get.
11. Have deep regard for the strengths, weaknesses, and motivations of every team member. Empower people to double down on their strengths and if they desire, bolster their weaknesses.
12. Trust is the most valuable asset of a team. Lend it generously, cherish it sacredly, and revoke it expeditiously.
13. Set clear, objective goals with your team and hold everyone accountable to that, including yourself. Make the time to hold 1:1s and build a relationship outside of work.
14. Never underestimate the power of incentives. If a team member refuses to acknowledge them, knowingly or under the guise of altruism, move on. Alt: Play Game B.
15. Diversity is a competitive advantage, not some political stance. Do not let language, location, or appearances color hiring decisions, but rather optimize for culture.
16. Heroes are admirable in the moment but in the long-run, consistent managers that elevate their team win. Do not glamorize the solo brawler.
17. Resumes are to candidates as book covers are to books. Interview for reasoning skills, emotional intelligence, and grit. Meta-skills like learning, asking questions, and communication are paramount.
Flow
18. Know when to sprint and embrace stress, and when to run the marathon and when to decompress. A routine and support system will let you reach for the stars, and if (when) you fall, you will land safely in your net. Invest deeply in your net. Alcohol is not a net.
19. Define your agenda early in the day, eat the frog first, and be absolutely infatuated with your flow state. DO NOT DISTURB.
20. Keep a large water bottle filled and by your side. Let's not have hydration be a blocker to flow.
21. Create an instrumental playlist that can reliably get you into a flow state. Look for melodies that are synthesis-oriented.
22. Maintain a routine that is sustainable and embodied. For example: reading, writing, and filling your water bottle daily. Bonus points if you are able to measure and gamify.
Vision
23. Live, breathe, and become the why. Making your startup's purpose ironclad and finding a truthful articulation of your vision will provide strength when you and your team need it the most.
24. When it comes to your vision, memorization is not understanding. Vision is an embodied truth that orients, transforms, and articulates the horizon. Explicitness makes it stale and thus rebirth it with every vocalization.
25. Vision is never entirely "owned" by one person. It is co-created by many individuals devoting deep thought and offering their insights. Every core team member carries a shard of that original vision within them.
26. Spend time with people that reaffirm your vision and those that reject it entirely. Be wary of sweet talkers by focusing on substance over delivery.
27. Attempting to boil the ocean will only fry your mind. Find a few fish in a pond, eat, and then go hunting for more.
28. Stay on the right side of the metaphysical boundary. On one side is a large TAM, and on the other is an ocean to get lost in. The sirens sitting far in the shimmering ocean will seduce you with their beautiful songs.
29. There is no nobility in rolling a giant rock up a hill for its own sake unless you're a masochist, of course. Like Art, it is the vision beyond that affords us any meaning at all.
Learning
30. Adopt the mindset that there is nothing in this world that can't be learned by reading, listening, and doing. Have an insatiable appetite to learn on an as-needed basis.
31. The difference between empathy and manipulation is intent, honesty, and love. Learning the art of identifying snake oil salesmen can only be understood through hard lessons.
32. Find the most compassionate and intelligent advisors you can. The journey is long and you'll need their wisdom to stay grounded and on the path.
33. Balance execution with reflection as you are in it, for one day you will look back and yearn to immerse yourself in deep purpose once more.
Product & Engineering
34. Complex architecture is best planned up front. Think deeply, build modularly, and document relentlessly to avoid code spaghetti.
35. Do not optimize architecture, code frameworks, design elements prior to product market fit. Code rewrites always have to re-solve already solved problems.
36. Feature bloat indicates a missing or incoherent product vision or an inability to communicate requirements to a team. Stay lean and true to testing to the USP.
37. When attempting to think rigorously about product, start with Why. Then for whom. Then what segments, and finally a vision for a solution, followed by specific ideas themselves.
38. Be wary of trying to introduce sophisticated product-engineering processes when there is not enough personnel to own every part and whole.
39. Craftsmanship is an emergent quality that is intrinsic, collaborative, and glorious. Recognize and reward.
40. If a product, piece of writing, podcast, or performance is not meaningful to you, then it will not be to another.
41. Product-market fit is a form of Love, insofar as love is a transformative and reciprocal opening of one another.
Finance & Ops
42. Market exuberance does not faze the wisest of us all. De-risk the venture at any and every opportunity you have, especially in deep tech endeavors. Minimize or simplify the number of variables in your runway function.
43. Meetings are mostly antithetical to work, but done right, they can cultivate more trust and prevent the commodification of people.
44. What people don't do sometimes speaks volumes more than what they do, whether that's in a call, on a product, or as a team member.
45. Do not be afraid. You can lose yourself in the abyss and you will find your way out once you understand what an entrepreneur is.
Meta
46. Reading this post may have been pointless. Language is an abstraction and the real transformation occurs within. Wisdom is embodied. Just go do it.