Over the last 10 years, I’ve made tons of mistakes, had some lucky breaks and a few big wins.

When you're starting out there's so much stuff that nobody tells you. Here are the top 20 lessons I learned the hard way that I would've loved to know when kicking off my career:
1/ Everything boils down to AMA

A: Ability - do you have the skills to pull it off?
M: Motivation - do you have the desire to pull it off?
A: Attitude - do you have the headspace to pull it off?

Strive for situations where each of these 3 are firing on all cylinders.
2/ People don’t have short attention spans, they have short consideration spans

If you want to meet someone, work with them and/or get their help, you need to figure out "the hook." Busy people get thousands of inbound emails, DMs and phone calls.

Focus on standing out.
3/ Adding value will get you consideration.

There’s one resource we’re all constrained by - time. If you want to build a relationship, figure out how you can make someone's time more valuable.

Make an introduction, help with an initiative, deliver an insight. Accelerate them.
4/ Don’t overstudy outliers (e.g. billionaires)

Outliers are unique by definition. If you obsess over analyzing how they succeeded, you'll likely pull out the wrong lessons.

If the ball bounced slightly sideways, the outcome would have been completely different.
5/ Aggressively seek out knowledge

A lot of rich people often say "nobody really knows what they're doing." 🤷‍♂️

Bull. Shit.

Most successful people I know are well intentioned, well networked and well read. There are clear proven tactics/strategies - learn these early on.
6/ Build in public

I wish I started this earlier. Building in public is one of the most underrated and powerful things you can do in your career.

College is $250k for a credential. The internet now allows you to do that for free.
7/ Build an audience

When I started my podcast, I did it with really strong selfish interest. I wanted to learn from the best in the world.

But sharing my thoughts created lots of opportunity.

⬆️audience = ⬆️reach = ⬆️surface area = ⬆️serendipity =⬆️opportunity
8/ Internalize asymmetric upside

An asymmetric bet is simple to understand. If you lose, you lose 1x. But if you win, there's no limit to the upside (♾)

You want to make sure you're taking enough swings (and the right types) to give yourself a shot at meaningful upside.
9/ Play games worth playing

My friend @ChrisJBakke has a pithy quote:

“$30M Under 30 > Forbes 30 Under 30.”

He said it in jest, but it’s spot on. In the internet era, it's easier than ever to chase vanity metrics (meaningless PR/accolades).

Focus on what actually matters.
10/ Optionality caps your downside AND your upside

As you progress in your career, the accumulation of skill is more attractive than the promise of potential. This shift can be painful - it happens very suddenly.

Sacrifice optionality early, so you can get more of it later.
11/ Building is 99% execution, 1% vision

We glamorize vision and foresight too much. The majority of any project is actually really boring.

It's all about being present, consistent and giving it the right level of effort day-in and day-out. This is deceptively difficult.
12/ Break up challenges into component parts

1. Incentives
2. Personalities
3. Perspectives
4. Constraints
5. Resources

Most difficult situations I have faced have been a function of ~2-3 of these being out of whack. I didn't realize this until long after the fact.
13/ "Anything is possible" doesn't mean "everything is probable."

It's important to understand: (1) whether something is likely and (2) the impact of a stated outcome.

There's no "right or wrong", but you should always be aware of the risk you're taking and its implications.
14/ The right time to start is yesterday

If you’re waiting for the right time, you’re implicitly assuming: (1) there is a “right time” AND (2) you will recognize that right time.

Think about that. Each is individually borderline impossible to diagnose, let alone both.
15/ Don’t compare yourself to others

As you get older, the likelihood that you will have an amazing friend that doesn't get the credit they deserve and a morally soulless person that gets ahead is pretty likely. Especially in tech.

Play your game and just focus on yourself.
16/ Learn just enough to be dangerous

You don't need to be an expert, but you should know enough about: (a) how the world works, (b) how businesses work and (c) how people think.

Most people surprisingly don't. If you do, you'll be an asset in any organization from Day 1.
17/ Learn the 101 of equity

Don’t EVER get duped. I've seen too many people accept options packages that they flat out don't understand.

It takes a small person to look smart.

It takes a big person to act smart.

If you don't know what something means - ASK.
18/ Seek out situations that maximize your value:

1. What am I GOOD at?
2. What does the MARKET need?
3. What do I WANT to do?

If you’re lucky enough to find the intersection of these 3, hold on tight.
19/ Spend time with people that are better than you

The quickest way to accelerate your personal growth is to surround yourself with people that are better than you at specific things.

Pick their brains and learn from them.

It's the fastest way to level up.
20/ Spend more time on Twitter

Seriously.

It sounds crazy, but I've made many of my best friends IRL from Twitter and learned a TON from them.

LinkedIn DMs = Death to Me
Twitter DMs = Deal Making

This platform is criminally underrated (and undermonetized! cc: @jack)
21/ BONUS: Don’t get high on your own supply. You’re not really that cool.

And the quicker you figure that out, the better it is for you and everyone around you.

*******

If you enjoyed this thread, give me a follow. I post threads like this 2-3x a week.
You can follow @RomeenSheth.
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