Summary

Good ideas start with personal passion + problem solving. Look for problems that exist, preferably your own. Leave your safety zone safely, find partners with complimentary skillsets, and do things that don’t scale. Explain why you exist. Experiment, put it out early, get honest feedback. Build a moat around a niche and find where the community is. A pivot can open a much bigger opportunity even when the old idea is working. Build a culture where people do the right thing, share values + purpose, and feel valued. Factor happiness into wealth vs control. Everyone gets lucky; it’s what you make of those flashes of luck.

“Starting a company is like throwing yourself off a cliff and building a plane in the way down.”
~ Reid Hoffman

“The real danger is getting to age 65 and saying ‘boy, I wasted my life.’”

Key Takeaways

Chappy’s Review

A good book! Very fun and easy to listen to and enjoyed hearing stories of entrepreneurs. Perhaps a little too approachable and not relevant enough to venture backed tech.

Notes

1: The call

• Adventurer → entrepreneur as frontiers are now social, intellectual, technological, economic
• Aware of risk and rewards of going out alone

1: Be Open to Ideas

• Ideas happen when you’re actively moving + searching
• “The intersection of personal passion and problem solving are where good ideas are built”
• PG’s “how to get startup ideas” - look for problems that exist, preferably your own
  • Most common mistake: solving problems no one has
• Hobbyist → tinkerer → entrepreneur

2: Dangerous → Scary

• We don’t do well with uncertainty
• “The real danger is getting to age 65 and saying ‘boy, I wasted my life’”
• Dangerous → scary
• The leap towards new, exciting, one’s own - now more than ever seems almost normal

3: Leave Your Safety Zone

• “Starting a company is like throwing yourself off a cliff and building a plane in the way down” - Reid Hoffman
• Either…
  1. Part-time til escape velocity
  2. Have a fallback plan
• Runway

4: Do Your Research

• Best: you find a problem but no good solution and others have it too
  • And you know how to solve it
• You’ll know it’s going to work
• Don’t rely on market research - Steve Jobs quote
• “Build a foundation of knowledge on which you can leverage your creative instincts and professional judgement in order to truly innovate”

5: Find Your Co-founder

• Importance of partners with complimentary skillsets
• Lonely, lots of ups and downs

6: Fund the Business, P1: Bootstrapping

• Do things that don’t scale
• Design research mode: watch your customers work
• Embrace the adversity
• Eg. Airbnb

7: Get Your Story Straight

• Must explain why you exist
• Customers, investors, employees, and ultimately yourself
• Eg. Bumble
• Stay anchored

8: Fund the Business, P2: Other People’s Money

• Do friends + family first: they’re betting on you > the idea
• Rejection. Going to need a thick skin

9: Iterate, Iterate, Iterate

• Phase 1: experiment
• Phase 2: put it out (early) and get honest feedback
• MUST mentally reframe feedback as positive
• Entrepreneurship incompatible with perfectionism
• Sweet spot of iteration

2: The tests

10: Go In Through the Side Door

• Niche
• Monopolize / build a moat around ↑

11: It’s All About Location

• Figure out if you have to move to break into industry or move to break out

12: Get Attention, P1: Building Buzz

• Insane power law of mobile apps: top 5 apps capture 85% of usage
• Media
• Find where the community is
• Be scrappy - eg. conventions
• Testimonials > brand story
• Create buzz

13: Get Attention, P2: Engineering Word of Mouth

• Create a “surround sound effect”
• Eg. Five Guys

14: Survive the Crucible

• “The best way out is always through”
• Crucible moments
• Distance yourself from the daily grind
  • Dancer in the chaotic ballroom vs viewing from the balcony and seeing the forest instead of the trees

15: Fund the Business, P3: Professional Money

• “The job of a VC is to be wrong 90% of the time”
• But often don’t invest in problems they don’t see / understand
• Learn a little more from each rejection

16: Protect What You’ve Built

• IP stuff - maintain ownership
• Watch out for people who’ll steal your business from you

17: When Catastrophe Strikes

• Eg. J&J
• Trust is paramount

18: The Art of the Pivot

• Must re-conceive
• What Got You Here Won't Get You There
• Eg. Justin TV → Twitch
• Often old idea was already working well, this is just a much bigger opportunity
• Eg. Slack

3: The destination

19: It Can’t Be All About the Money

• The mission
• Why > what (JTBD, emotional)

20: Build a Culture, Not a Cult

• Culture = so people do the right thing
• Cult = too centered around the founder, trying to do everything themselves
  • Monarch CEO
• Control freak → brain drain

1. Find people who share your values + purpose

• Bad people = not aligned = spoils the whole company
• Eg. Netflix 130-slide culture deck
• Values = consistency = trust

21: Think Small to Get Big

• Think small / stay within your means and opportunities will present themselves
  • Foothold
• Eg. Belkin
• Build adjacent to / shovels for the current revolution

22: Manage Partnership Tensions

• Like romantic relationships

23: Know Thyself

• Know your company’s DNA + how the team is feeling

24: When to Sell and When to Stay

• Wealth vs control: The Founder’s Dilemmas
  • Rich vs king outcome
• ↑ must factor in happiness
• Eg. Cliff Bar co-founder $60M buyout

25: Be Kind

• Make being kind your North Star
• Empathy, customer and otherwise
• Make team feel valued
• Give people ownership / equity
• Eg. Patagonia
• Confidence in people to manage their own time
• Culture has to start with the very first team member
• Build a team that can’t imagine working anywhere else

26: What You Do with Your Luck

• Luck vs hard work?
• So many smart people out there - it necessarily has to be mostly luck
• His theory: everyone gets lucky, it’s what you make of those flashes of luck
• You have some agency over it ↑

Afterword

• Moments of reflection are crucial
• Founding is lonely
• Need to share + reflect with people
• Chatter perspective take