Summary

The beginning and end of a venture get all the glory – the messy middle is where everything actually happens. Endure the volatility by anchoring to your customers (empathy for problems over solutions), building a team through initiative and kill-ambiguity culture, and relentlessly simplifying the product. Optimize yourself: cut passive commitments, audit routines, ask for forgiveness not permission.

“The accounting of how you spend your minutes is the hard truth of your values.”

“The more voluntary suffering you build into your life, the less involuntary suffering will affect your life.”
~ Tim Ferris

Key Takeaways

Notes

1: Endure

1: Leading through the anguish, unknown

• Manufacture motivation
• You can’t change the truth, but you can assign meaning to it
• Commit to uncertainty, suffering
• Shared struggle, friction brings ppl together
• Be the steward of perspective
  • Landmarks, road ahead
• Leave every convo with energy, purpose

2: Strengthening your resolve

• Nobody remembers those who fit in
• “What would it take to achieve 100x of what you’re proposing?”
• Grit
• Investigate mistakes impartially

3: Embracing the long game

• Requires moves that don’t map to traditional measures of productivity
  • Eg. brainstorming
• Bezos’ legendary investor letter postscript
• Break the long game into chapters
• Fake it til you make it
• Be proactive

2: Optimizing team

4: Building, hiring, firing

• Be resourceful
• Initiative > experience
• Hire for diversity, adversity
• Need dreamers and doers
• Integration: build confidence upfront
• 70/20/10 model for leaders: 10% teaching, 20% feedback + coaching, 70% experience
• Apprenticeship is mutually beneficial
• Keep reevaluating people
• Keep shaking things up
• Build up team’s tolerance for change
• “The more voluntary suffering you build into your life, the less involuntary suffering will affect your life” - Tim Ferris

5: Culture, tools, space

• Need stories from the past
• Free radicals: people who are destructive or instrumental depending on context
• Give people ownership, praise
  • Credit: assigning influence for future decisions

6: Structure, communication

• Be flexible with “the rules” / convention
• Let people have their own processes
• Abstract idea needs a mockup
• Be less polished, more real
• Assign a DRI to everything
• Be candid: say it like it is
• Be explicit, specific, and brief

7: Clearing the path to solutions

• Take organizational debt
  • Give process + incentive to call out bad processes
• Kill ambiguity
• Don’t avoid conflict
  • Friendly front stabbing > backstabbing
• Channel competitive energy
  • Be grateful for competitors
• Humility in face of truth
• Ask for forgiveness, not permission
• Intuition → conviction > consensus

3: Optimizing product

8: Simplifying, iterating

• Essentialism: identify what you want to be bad at
• One subtraction for every addition
• No sunk cost fallacy
• Beware creativity → friction
• Maximize vs satisfies
• Mentality: users are lazy, vain, and selfish
• Leverage novelty
• Constant evolution

9: Anchoring to your customers

• Empathy for customer problem > solutions
• Know your “why” / narrative
• Be fair + transparent in network
• Don’t promote products before ready
  • Soft launch, don’t be first
• Create information gaps

4: Optimizing yourself

10: Planning, making decisions

• Systems thinking: choose projects based on skills, relationships
• “Cheering from the sidelines, but out of bandwidth”
• Overcome endowment effect: “if I didn’t own this, how much would I be willing to pay?”

11: Creating business instincts

• Explore contributions in thought/opinion
• Minimize tracked core metrics
• Preserve the art in your business

12: Sharpening your edge

• Cut out your passive commitments
• “The accounting of how you spend your minutes is the hard truth of your values”
• Audit your routines
• Make room for the circumstantial
• Disconnect, understand your myopic perspective
  • Be proactive, not reactive

13: Staying permeable and relatable

• Let others have their own creative process
  • Keep your distance → ownership
• Keep making a ruckus

14-15: The finish line

• Seek advice, don’t go it alone
• Stay in the early innings
• “You deserve it”

16: Passing the baton

• End gracefully and with humility
• Go out on your own terms

17: Never being finished

• Realize when your deeply held convictions are wrong
• Friction → remembrance