← The Knowledge Project

#98 Sahil Lavingia: Observing the Present

Dec 8, 2020 1h 11m 33 insights
Sahil Lavingia is the founder and CEO of Gumroad, an online marketplace for creators. In this conversation Sahil and Shane cover building a billion dollar business, the most critical skills for success, how he hires, his worst mistake, the patterns of success and failure and so much more. -- Want even more? Members get early access, hand-edited transcripts, member-only episodes, and so much more. Learn more here: https://fs.blog/membership/   Every Sunday our Brain Food newsletter shares timeless insights and ideas that you can use at work and home. Add it to your inbox: https://fs.blog/newsletter/   Follow Shane on Twitter at: https://twitter.com/ShaneAParrish
Actionable Insights

1. Own Your Problems

Take full responsibility for your challenges and company, as no one else will fix them or make you rich; it’s up to you to convert potential into kinetic energy.

2. Curate Your Peer Group

Consciously choose the people you surround yourself with, as you become the average of your five closest friends, and their questions will become your own.

3. Gain Perspective Through Distance

To overcome self-consciousness and analyze your life objectively, create physical or mental distance from the environment that shapes your identity.

4. Avoid External Identity Validation

Do not conflate your identity or value with your rank, position, or what you can do for others, as this can be detrimental long-term.

5. Build Voluntary Relationships

Form relationships that feel ‘at will,’ where both parties frequently re-up, fostering a voluntary and less attached connection with employees, investors, and others.

6. Prioritize Saving Others’ Time

Operate in a way that requires less effort from others, acting like a concierge service to make interactions stress-free and easy for them.

7. Over-communicate Proactively

Consistently communicate your needs, feelings, and what’s happening now, next week, and next month to reduce stress for others and allow them to solve problems before they arise.

8. Master Written Communication

Spend time writing and revising emails and other communications to ensure clarity and provide all necessary context, saving time for all involved and elevating the conversation.

9. Make Specific Requests for Help

When seeking help, make very specific requests (e.g., ‘an intro to X’ with a blurb and deck) rather than generic ‘how can I help?’ to enable quick and efficient assistance.

10. Consciously Choose Your Inputs

Be mindful of the books you read, people you listen to, and tweets you follow, as you absorb their perspectives and ‘you are what you eat’.

11. Read Deeply and Broadly

Engage in deep reading about your industry and other subjects, and also explore broadly to find new and different connections and insights.

12. Read Without Social Incentive

Read books and learn for the sake of knowledge and becoming smarter, rather than for social signaling or immediate external validation.

13. Prioritize Observation as Skill

Recognize that observation is a fundamental skill; truly seeing what’s in front of you and noticing details is often the hardest part of learning or creating.

14. Break Down Skills into Fundamentals

To learn a skill, break it down into its fundamental building blocks and master those sequentially to gain a deep understanding rather than just memorizing.

15. Understand Physical Reasons

Seek to understand the fundamental physical reasons behind phenomena (e.g., why hot water cleans faster) to gain a deeper grip on reality and apply knowledge effectively.

16. Immerse Yourself in Your Field

If you aspire to a certain role (e.g., founder), spend time hanging out with people in that role and working in related early-stage environments.

17. Build Relationships Without Agenda

Cultivate relationships by discussing product or other topics without an agenda, as this builds trust and can accidentally do the work for future opportunities.

18. Build and Create Things

Actively build and create things, rather than just having ideas or needing others to do everything for you, as this demonstrates initiative and capability.

19. Start Small and Figure It Out

If you want something badly, figure out how to start with what you have, even if it’s not your ‘dream project,’ and learn as you go.

20. Don’t Ask for Permission

Take initiative and proceed with your ideas and projects without waiting for external validation or permission.

21. Focus on High-Quality Outreach

Instead of a numbers game (e.g., 100 emails for 3 yeses), focus on sending fewer, highly personalized emails (e.g., 3 emails, 3 hours each) with the expectation of a high success rate.

22. Recalibrate When Growth Slows

If your venture-backed company isn’t growing as fast as needed, pause, recalibrate, and figure out a new strategy before drastic measures are required.

23. Automate Tasks with Software

Utilize software tools like Calendly, Zapier, and Airtable to automate routine tasks, effectively operating as if you had a full-time executive assistant.

24. Clarify Meeting Agendas Upfront

When someone asks to ‘catch up,’ proactively ask them what they want to talk about to ensure both parties are prepared and the meeting is efficient.

25. Prepare in Advance for Meetings

Do the necessary work ahead of time (e.g., reading material) so that you can contribute effectively and potentially avoid the meeting altogether if information can be shared asynchronously.

26. Process Obsessive Thoughts by Writing

If a thought is stuck in your head, process it by figuring out what it is, why it is, and packaging it for clarity, then share it to release it.

27. Engage in Deep, Focused Work

Dedicate focused, intense effort to solve problems, treating it like a workout where you push yourself to concentrate deeply.

28. Balance Conversation and Solitude

Structure your life to alternate between engaging in interesting conversations and spending time completely alone.

29. Read ‘How to Win Friends’

Read Dale Carnegie’s ‘How to Win Friends and Influence People’ as a canonical example of operating in a way that makes others’ lives easy and stress-free.

30. Read ‘Thinking, Fast and Slow’

Read Daniel Kahneman’s ‘Thinking, Fast and Slow’ to understand cognitive biases and decision-making.

31. Read Matt Ridley’s Books

Read Matt Ridley’s books to understand the physical and biological constraints of the brain and body, helping to differentiate what you can and cannot control.

32. Read David Deutsch’s Books

Read ‘The Beginning of Infinity’ and ‘The Fabric of Reality’ by David Deutsch to explore concepts like parallel universes, quantum mechanics, and free will.

33. Learn from Past Entrepreneurs

Read books like ‘The PayPal Wars’ and ‘In the Plex’ to learn from the experiences of those who built companies before, applying timeless lessons rather than starting from scratch.