I interviewed 100 legendary investors, founders and executives.

Collectively, they have created over $1 trillion of value for the world.

Here are 20 practical career lessons they shared with me 👇👇👇

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.
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, judgement, trust, empathy
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.
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
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.
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.
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.
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.
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.
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.
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.
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.
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.
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
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
You can’t do it alone no matter how great you are

To win big, surround yourself with 3 things:

1. Other greats
2. Role players
3. A system that brings out the best in everyone.

All three of these are equally important and allow you to thrive.
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
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.
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.
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 LESSON: 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.
If you enjoyed this thread, give me a follow:

➡️@romeensheth⬅️

I tweet 2-3 times a week about lessons learned building and scaling a $50M+ bootstrapped business.

More from Romeen Sheth

The cold hard truth:

Why do companies like Quibi raise billions, while companies like Peloton get nothing?

Because fundraising is a GAME

And the insiders keep the rules to themselves.

Here are 100 tips the insiders don’t want you to see but will help you win the game:

1. You can’t play the game without nailing the basics.

There are 5 core ingredients to a startup pitch.

Most have 2.
Good ones have 4.
The best have all 5.


2. Now that you have a grasp of the basics, it’s time to level up.

Good news - most founders make the same mistakes as each other.

Bad news - these mistakes are really easy to make.

Here's what not to do:


3. Ok so you told me what not to do.

So what should I do?

Read below.


4. We’re in a really unique fundraising environment right now.

It’s important to contextualize all these tips in the “here and now” of what’s going on in the landscape.
Early career years are painful.

You feel like an idiot 98% of the time - lost, confused and insecure.

I wish I had a playbook on principles for my first job.

So I put one together.

Here are 9 threads packed with lessons about building a career I wish I knew sooner:

1. First and most important - have a clear mind.

Without clarity of thought, nothing else matters.

Here are the most common types of distortions I’ve observed over the years.

Self awareness has helped me catch myself before falling into a trap.


2. Enter the side door

Most people enter the “front door” in their careers.

The problem is - when you do what most people do, you get the results most people get.

If you want a n-of-1 career, don’t take the 1-of-n path.


3. Adversity is inevitable

Any journey that’s worthwhile is filled with adversity.

If it was so easy...everybody would do it.

Here’s the way I’ve worked through dealing with the road blocks that are part of every entrepreneur’s journey.


4. Learn from the world's best

I love talking to world class people - CEOs, Founders, Execs, Athletes.

There's a lot of commonality in world class success.

Unpacking how these people got to where they are is always inspiring.

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