Resources & reflections from a year of startup life.

Here is a list of resources — people, articles, video, audio, books — that have helped me navigate my first year with my startup, CardBoard.Live.

A few things about me:

  1. I record and document nearly everything: conversations, articles, resources, and so forth. I journal every 2-3 days. I keep a list of people to stay in touch with, use Pocket to save and label the best articles, and find time to re-read good articles so that I can effectively retain the information.
  2. I learn and absorb well from other people. I grew up as the kid who reads instruction manuals and have taken that concept to life in general. I hate not being prepared. I prefer not to make silly mistakes for the first time if I know how to leverage other people’s learnings.
  3. I believe habits are really important. What time of the day you wake up, how you structure days of the week for thinking time vs. exercise time vs. work, etc…that is important to me.

Discovering and revisiting the resources here have helped me tremendously.

This is my personal “best of the best” list and represents <5% of the content I’ve absorbed in this 1-year timeframe.

People

My friend Sean K. (entrepreneur, current Beijinger and life-long Bostonian)

  • Believe in yourself…especially when you’re doing pitch #93.
  • Pitching is about anticipating the reactions/questions from each slide.

Tim Ferriss

  • “Being busy is a form of laziness – lazy thinking and indiscriminate action.”
  • Being chronically “busy” is a sign that you’re not in control of your life.

Jason Calacanis

  • Hustle gets a bad rap — but do you want to be Uber, or do you want to be Lyft?
    • Lyft is a $5B company (& is now IPO’ing!) but clearly isn’t dominating like Uber is.
  • Good investors have a long time horizon.

Wilson Hunter (co-founder of CardBoard.Live and my partner-in-crime)

  • When trying to convince, remove the “no’s” from your audience’s mental equation. Anticipate and be proactive.
  • Concise is best.

Myself (self-reflections)

  • On results
    • Results matter, when it comes to personal performance / managing people / maintaining credibility.
    • Verbalizing “I tried” is a weakness. Nobody cares that you tried. If you try and don’t succeed, figure out a better way.
  • On running companies
    • The “culture” of a company is what you do when nobody else is looking.
    • Look to articulate your culture after-the-fact, when you have the mental bandwidth and credibility to do so. Doing so too early on in the process is not worth it and can destroy one’s credibility.
  • On people & relationships
    • Never mistake for deliberate malfeasance what can be explained by sheer incompetence.
    • People that initially deliver and live up to their reputations can end up disappointing you later on. The opposite, however, is NEVER true. If someone disappoints you from the very beginning, do not ever expect them to turn it around. Move on and don’t waste your time.
    • The biggest mistake you can make is to assume that people are just like you.
    • Credibility is earned.
    • Trust is earned.
  • On critical thinking
    • Quiet confidence is important.
    • Belief and confidence must be earned, and does not have to be outwardly expressed in all scenarios.
    • Read the room and adjust. Figure out who your audience is.

Articles

Do things that don’t scale – Paul Graham

  • What is “insanely great”
  • Customer obsession
  • Startup as newborn baby. “There’s no way this tiny human would ever amount to anything.”

How to convince investors – Paul Graham

  • Be factual
  • Confidence and momentum comes from actual achievement
  • Believe in it yourself
  • “Why didn’t VC X invest in you?” -> “They didn’t think XX was possible. But this is where they’re wrong because YY…”

How to raise money – Paul Graham

  • Avoid investors till you decide to raise money, and then when you do, talk to them all in parallel, prioritized by expected value, and accept offers greedily.
  • Fundraising is not what will make you successful. It’s just a means to an end. Your primary goal should be to get it over with and get back to what will make you successful — making things and talking to users…

Productivity – Sam Altman

  • Compounded productivity gain is huge.
  • WHAT to work on is over half the battle. Spend time thinking about the “what.”
  • Sam personally relies heavily on lists. (I have a modified method which kind of works)
  • Overcommitting to items a “bit” is good, in the sense that it forces you to be more creative/efficient. But don’t overdo it.
  • Don’t neglect family.
  • Don’t neglect doing things that make you happy.

How to be successful – Sam Altman

  • Compounding gains.
  • Possess strong self-belief, but constantly ask and internalize feedback.
  • “I will fail many times, and I will be really right once.”
  • Sales: show up in person whenever possible.
  • “I have yet to meet a slow-moving person who is successful.”
  • “A big secret is that you can bend the world to your will a surprising percentage of the time—most people don’t even try, and just accept that things are the way that they are.”
  • “The size of the network of really talented people you know often becomes the limiter for what you can accomplish.”

Zero to $10B – Jonathan Swanson

  • “Be confident that you can eventually figure everything out; be humble about everything else.”

A Decade of Remote – Viktor Petersson

  • True “remote” requires equal commitment from everyone — those that don’t fit culturally should find other employment
  • True “remote” is a way of (working) life, not an option where some go to an office and some don’t
  • The right discipline and habits are what separate “successful” remote workers from non-successful. Also, eliminating bad habits and distractions is key (“deep work” principle).
  • Sleep really matters, and is a great natural performance-enhancing drug.
  • Invest in yourself, and this includes buying high-quality equipment for work.

Feeling good: Justin’s program – Justin Kan

  • “Disease of more” – “hedonic treadmill” – how much is enough?
  • Explicit gratitude helps.
  • Practice ongoing negative visualization – Tim Ferriss calls this “fear-setting.”
  • Be aware of phone overuse. (Justin averaged 5.5 hours/day before he changed habits)
  • Be authentic. Be honest with friends about what they mean to you.

Audio

Startup Playbook – Sam Altman

Tim Ferriss podcast – Tim Ferriss. I admit this is very general but Tim’s podcast has consistently been the best thing I’ve listened to over the past five years.

Video

Amy Buechler and Michael Seibel on Founder Coaching and Having Hard Conversations

How to start a startup – Stanford lecture series – Sam Altman

Lecture 2 – team and execution

  • Important topic

Lecture 9 – how to raise money

  • Be so good they can’t ignore you (Marc channeling Steve Martin)
  • Peeling away the onion. Startup = set of risks, more capital allows you to de-risk

Lecture 10 – Culture (Brian Chesky)

  • Culture = a shared way of doing things (in a collective/company/team/whatever)
  • Helps inform key decisions
  • The core values aren’t just about integrity — those, everyone should have. Question: what are YOUR special values? Figure out 3-4 of them.
  • Hire slowly. Brian’s standards for first employee(s) were super high. Took hundreds of candidates to land one. Culture focus actually slows down the process.
  • AirBnb value examples:
    • Champion the mission – be here for the right reasons, do you believe in friendship and connecting people, job vs. calling
    • Creative frugality – story about selling Obama/McCain cereal to fund the early days

Casey Neistat’s life advice compilation

“How to raise money” – Jess Lee (Partner @ Sequoia)

David Rubenstein interview w/ Bezos in 2018

Takeaways from Bezos interview:

  • Excellent video & worth re-watching.
  • Intuition should guide a lot of decision making, contrary to Amazon and Jeff’s public data-driven “persona.”
    • The problems requiring data-driven analysis to solve are relatively easy.
    • Buying WaPo was an intuition-based decision, and based on recommendation from 15-year friend.
  • What’s his principle to life?
    • Minimizing the number of regrets over a long period of time.
    • Imagining what his life would be like when he’s 90 years old.
  • Decision-making approach
    • It’s about making high-quality decisions
    • Also limiting the number of decisions made in a given time span.
    • Jeff’s tackles his biggest intellectual challenges in the AM, not in the afternoon.
  • Ideas
    • Holding strong convictions and beliefs are key to success.
    • Powerful ideas (Prime, AWS) often come from the unlikeliest places.
  • Leadership
    • Jeff’s direct reports “live in the future” — they don’t concern themselves with daily minutia. It’s about thinking about the future.
  • Quirks
    • Opening a “Montessori-like” school and calling the students “customers” — a bit disturbing, only slightly better than calling kids “users”, but consistent with Jeff’s ethos.
  • Beliefs about the future
    • Expanding beyond the Earth is a choice. Humans can choose to curb their growth, and hence energy usage. But Jeff wants future generations to be able to consume and use more energy than ever. (it’s a conviction AND a choice)
    • Blue Ocean is about building foundational, affordable pieces for future space travel. It’s like UPS making long-distance mail sendable for all.

Thanks for reading! I hope you enjoy these resources.

Peace,
James

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