Lessons from 120+ legendary investors, founders and executives: Invest in permanent skills

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Most people overinvest in expiring skills & underinvest in permanent skills. Expiring skills are tactical; their relevance diminishes with time and technology Permanent skills are evergreen and create disproportionate impact (e.g. communication, judgment, trust, empathy)

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I’ve interviewed 120 legendary investors, founders and executives on my podcast. Collectively, they have created over $1 trillion of value for the world. Here are the best 20 lessons they have shared with me:
1. Always strive to simultaneously be overrated and underrated. Contrary to popular belief, being overrated is good. It opens doors and gives you credibility. But don’t let this go to your head. Stay hungry, humble and hardworking.
2. Most people overinvest in expiring skills & underinvest in permanent skills. Expiring skills are tactical; their relevance diminishes with time and technology Permanent skills are evergreen and create disproportionate impact (e.g. communication, judgment, trust, empathy)
3. Get comfortable with being uncomfortable If you get advice from enough people, the advice will cancel out. You can find 2 smart people to take opposite sides of the argument on virtually every topic. Focus on developing your instincts and trusting your own intuition.
4. Surround yourself with open minded people vs. close minded people Open Minded People: – Ask genuine questions – Insatiably curious – Listen attentively Close Minded People: – Make statements instead of ask questions – Focus on being right – Speak more
5. Sweat the details Most people hate messes and avoid them like the plague. But this is where the impact lives. If you let details go, you slowly chip away at your core. Doing 1% less consistently makes underachievement inevitable.
6. Focus on inputs vs. outputs. It’s really important to separate inputs (process) from output (outcomes). Every so often you will have a great outcome that seemingly comes out of nowhere — this is luck. Do not get seduced by it; it isn’t repeatable.
7. Be ruthless about what you say “yes” to. Every commitment is 2 decisions: (1) A decision to engage on X AND (2) a decision not to engage on Y. Guard your time. As the road widens, many of the detours are seductive.
8. Consistency is the most underrated element of success Most people hit roadblocks and give up. Successful people understand roadblocks are a part of the journey. When you hit a roadblock – embrace it, work through it, celebrate and then “re-rate” your baseline.
9. Work like a lion, not a cow Cows consistently graze. This is akin to 9-5 jobs. Always operating at ~30% efficiency. Lions pounce in bursts. This is counterintuitive. Work on high intensity, high value projects. Execute at 120%. Rest. Rejuvenate. Repeat.
10. Nip problems in the bud quickly. Every complexity starts out as a snowball. Address it head on. If you let it fester, it’ll turn into a boulder and you’ll either (a) get crushed or (b) have to spend an inhumane amount of energy to fix it.
11. There are 2 paths to success: – Be Top 1% in the world at 1 thing – Be Top 25% in the world at 3 things Top 25% is achievable by most people. The problem is most people focus on being Top 1%. Work on combining “3 pretty goods” and stay at it. It’ll pay off big.
12. Luck can be created Build in public. Send that cold email. Build relationships with people you look up to. The most interesting opportunities are never on job boards, they’re created organically.
13. History is filled with businesses and people that win because they have the best story. – Best idea? Maybe – Correct answer? Maybe – Most useful answer? Maybe Most persuasive story? Definitely Nobody wants the facts, everybody wants a story.
14. Become a master at sales and negotiation Every opening is a sale – partnerships, recruiting, vision, fundraising Every close is a negotiation – hiring, alignment, price, terms, value
15. Focus on what you can control vs. what you can’t control Can Control: – Attitude – Mood – Reaction – Effort – Curiosity – Motivation Can’t Control: – Other People – The World
16. You can’t do it alone no matter how great you are To win big, surround yourself with (A) other greats, (B) “role players” and (C) a system that brings out the best in everyone. All three of these are equally important and allow you to thrive.
17. Play games worth playing How to build a successful business: – Traction – Speed – Simplicity – Consistency – Community – Iteration – Imitation How to feel like you’re building a successful business: – $ Raised – Investor Brand – Advisors – Headcount – Adulation
18. Having a billion dollars is great, having a billion seconds is priceless. Interesting thought experiment: If you had the opportunity to switch places with Warren Buffet, would you do it? You would be a billionaire, but you would also be 90. Time > Money.
19. Everybody wants the same fundamental things At the end of the day, everyone wants the same thing: to feel fulfilled, maintain pride and enjoy what they’re doing. Remember that, apply it to every interaction you have and you can get through the toughest of conversations.
20. Find your anchor. Religion. Family. Friends. Kids. Whatever it is, find it. Life only gets more complicated as you grow older. Anchors help keep it simple – they remind us what actually matters.
BONUS: Don’t get high on your own supply. Don’t be a jerk. It isn’t cool.
And that’s it! I consistently reflect on these 20 lessons – the best part about them is many are counterintuitive / non-obvious. It takes time to internalize and apply these. Step 1: Digest Step 2: Practice I hope these lessons help you in your journey.
Thanks to all the incredible folks that have come on my pod over the years and shaped these lessons. Too many to mention by name, but a special shout out to: 1. @DavidSacks 2. @AndrewYang 3. @rabois 4. @chamath 5. @arachleff 6. @msquinn 7. @ApoloOhno 8. @eladgil 9. @arjunsethi
10. @KatColeATL 11. @thatchriskelly 12. @timyoung 13. @manikgupta 14. @davidtisch 15. @bradleytusk 16. @karanortman 17. @JChillin 18. @GuptaRK22 Many of you have become close personal friends. The internet is so awesome.
If you thought this was interesting – check out my pod. We’ve got an awesome lineup coming up: @lukeburgis – Mimetic Desires @eladgil (round 2) – Techno-optimism @ev – Media, Polarization, Future of Consumer @_ram_ – US & China +Many more!