This past week my good friend
@JChillin
and I hosted Gametime 2024.
We brought together 150 of the best professional athletes, founders, investors and family offices together for a day of collaboration, learning and sharing.
It was an honor to host this event. The room was
Early career years are painful.
You feel like an idiot 98% of the time - lost, confused and insecure.
I wish I had a cheat sheet of principles for my first job.
So I put one together.
Here are 20 things about building a career I wish I knew sooner:
Early career years are painful.
You feel like an idiot 98% of the time - lost, confused and insecure.
I wish I had a cheat sheet of principles for my first job.
So I put one together.
Here are 20 things about building a career I wish I knew sooner:
Early career years are painful.
You feel like an idiot 98% of the time - lost, confused and insecure.
I wish I had a cheat sheet of principles for my first job.
So I put one together.
Here are 20 (non-fortune cookie) things about building a career I wish I knew sooner:
I talked to a super smart 20 year old this week.
All the potential in the world, but had a major major flaw in his thinking.
This flaw is becoming the most common mistake I am seeing young people make early in their career.
Let's break it down:
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:
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:
2022-2030 will be a Renaissance Decade.
I’m investing $3M in 2022.
Here are the 10 biggest opportunities I’m most excited about.
If you’re building in any of these areas, let’s chat:
The world's most valuable skill:
Clarity of thought.
The problem? There's no school for this.
It takes time, patience and a lot of early career fumbling.
Here are 10 cognitive distortions I faced early in my career and an insight on how to break through each one:
Early career years are painful.
You feel like an idiot 98% of the time - lost, confused and insecure.
I wish I had a cheat sheet of principles for my first job.
So I put one together.
Here are 20 (non-fortune cookie) things about building a career I wish I knew sooner:
I talked to a super smart 20 year old this week.
All the potential in the world, but had a major major flaw in his thinking.
This flaw is becoming the most common mistake I am seeing young people make early in their career.
Let's break it down:
The world has never been more peaceful, prosperous or healthy.
But if you read the news you'd think the apocalypse just happened.
Here's 10 charts on why it’s never been better to be alive and what it means going forward:
Pretty high alpha career move to join Twitter right now imo.
I saw this time and time again when doing M&A at McKinsey. The best career moves (in big companies) are made when everything is in flux.
It’s all up for grabs.
I talked to a super smart 20 year old this week.
All the potential in the world, but had a major major flaw in his thinking.
This flaw is becoming the most common mistake I am seeing young people make early in their career.
Let's break it down:
I have a confession to make: I used to hate public speaking. My palms got sweaty, my voice choked up and I always thought about that time in college when I had to give a presentation, got up at the front of the room and literally blanked. The whole class stared at me. I was up
This week I interviewed someone who:
- Built a $1.5B company as COO
- Sold a $1B company to Microsoft
- Invested in 25 🦄🦄🦄🦄
Here’s 10 timeless lessons from one of the greatest tech entrepreneurs of our generation:
The world's most valuable skill:
Clarity of thought.
The problem? There's no school for this.
It takes time, patience and a lot of early career fumbling.
Here are 10 cognitive distortions I faced early in my career and an insight on how to break through each one:
25 predictions for 2023:
1. TikTok banned in the US
2. US govt budget > 50% GDP
3. PE scoops up 30% of public SaaS companies
4. Global manufacturing shifts from China to India
5. Investing in AI is a headfake
6. A Tier 1 investor blows up
I quadrupled down on angel investing this past year.
I’ve invested $2M in 30 companies.
In the process, I’ve learned what feels like 5 years worth of lessons.
Here are my 15 biggest takeaways for anybody interested in angel investing 👇👇👇
There’s a lot of bad advice out there on how to pitch your startup.
Last year, I invested $1M+ and heard 200 companies pitch.
Every great pitch I've heard nails 5 ingredients.
In this thread, we'll go through each to help maximize your chances when fundraising
Let's dig in👇
Satya Nadella is the 🐐
- LinkedIn at $26B
- Nuance Communications at $20B
- GitHub at $7.5B
- ZeniMax at $7.5B
Now Activision at $70B. All cash.
Absolutely incredible.
Imagine calling an immigrant that came to the US with no money and graduated with $100k+ in debt (despite scholarships & working 2 jobs while at school) a “freeloader.”
@elonmusk
embodies the American dream.
Debating policy is fine. Calling him a freeloader is absurd.
"What does the rest of the world not get about India?"
I asked
@kunalb11
this question last week. Kunal founded
@CRED_club
- a leading Indian fintech valued at $6.4B.
This list is a must read if you're interested in Indian startups.
Here were my favorite insights he shared:
Nothing pisses me off more than Lawyers ripping Founders off when putting investment docs together.
The worst part is most Investors aren’t helpful - 85% push the bill to Founders.
As an ex-lawyer, I saw all the inside tricks.
Here's how to reduce your legal bill by 90%:
No book, podcast or Twitter thread will simulate how you actually feel when:
- A deal falls apart at the last minute
- A key employee leaves you
- A partner abuses your trust
You have to actually live through those things.
My friend
@SahilBloom
has this framework I've stolen that has been really impactful for my life.
He calls it "The Character Alarm Method."
Here's how it works:
I. Break down the components of your ideal day - First, take a step back from your daily schedule. It’s filled with
The world's most valuable skill:
Clarity of thought.
The problem? There's no school for this.
It takes time, patience and a lot of early career fumbling.
Here are 10 cognitive distortions I faced early in my career and an insight for you to break through each one 👇👇👇
🚨Thrilled to announce In the Trenches - a newsletter where I will share practical frameworks, tools & tactics to level up in business and life.
Over the last four years, I have:
- Bootstrapped a company to $50m+ in revenue and exited to a Private Equity firm
- Angel invested
India is on absolute fire. Over the past week, 6 startups have raised monster rounds:
- Groww: $100M
- CRED: $215M
- Meesho: $300M
- Pharmeasy: $350M
- Sharechat: $502M
- Swiggy: $800M
India isn't the future. It's the present.
Time to put some respect on its name🔥
But you don’t.
Even worse, you *think* you do.
Here’s the hard truth: Internalizing all those observations and lessons without having any grounding, context or actual experience is just like WATCHING bball when your goal is to learn how to PLAY bball.
0/ The Domino’s pizza turnaround is one for the ages:
1960: Founded
2004: IPO
2008: Hits record low $2.83/share
2020: Current stock at $367/share (130,000% gain)
The 100x+ growth story is filled with a bunch of lessons for startups today.
Let's dig in.
So why do most people read/listen vs. do? I think a couple reasons:
- It feels like progress
- You can’t fail
- It’s intellectually stimulating
The reality of business is most of the work is not glamorous.
It’s a lot of nose to the grind, brute force execution.
This week I want to share a story of one of the most challenging startup experiences I’ve been through.
Though at the time it was gut wrenching, I’m incredibly grateful for it.
The experience gave me a framework on company building that I have applied ever since.
Here it is:
Principle
#1
: You’re not the “Strategy Guy”
Yet.
To be a big picture thinker, you have to earn the respect, trust and credibility of your team first.
The only way you can do this is through delivering tangible value.
Focus on bringing results, not laying out frameworks.
Atlanta startups are on fire 🔥
Calendly - raising at $3B valuation
OneTrust - $2.5B valuation
Greenlight - $1B+ valuation
Kabbage - just sold for $800M.
We have hit an inflection point in Atlanta - the next 10 years are going to be really runs
@JoePompliano
You know what the best part was?
He learned how to throw a javelin on YOUTUBE.
The internet is wild and huge equalizer for the developing world.
This is the first of many amazing stories to come out of India over the next decade.
This week I had
@chamath
on the pod for a hard hitting 80 min discussion.
Man, this was fun.
Here’s 15 unique insights I learned from one of the greatest tech icons of our generation 👇👇👇
"What does the rest of the world not get about India?"
A question I asked founders of 15 hyper growth Indian companies over the last few weeks.
The answers spelled out what is driving the velocity behind India’s rise as a startup ecosystem.
Here were my 10 favorite insights:
"I want to switch careers, but I’ve invested 5 years in the path that I am on and I fear that if I switch now I am going to have to start over. How would you think about this?"
Most people idealize careers as clean linear trajectories. They are not. They are windy, messy and
Something most people in tech don't know:
McKinsey is a software 🦄hiding in plain sight.
I worked there for 3 years and saw 10 acquisitions that allowed McKinsey to shatter $100M+ ARR.
Here’s the breakdown 👇👇👇
I came across this wonderful piece from
@mbrandolph
, Co-Founder of
@netflix
, the other day.
Highly recommend reading it and internalizing it.
5 key lessons I pulled away from Marc’s reflection:
1. Everyone should have a north star - success is what you make of it; money,
Here's how I got my first job at a startup:
❌ Applied via job posting
❌ Got a warm intro
❌ Knew somebody at the company
✅ Downloaded the product
✅ Wrote down 10 things I would improve
✅ Cold emailed the CEO the list and said let's chat.
Lesson: Show, don't tell.
For all its flaws, America is still the greatest country in the world:
- best education system
- best system of government (democracy)
- best economic system (capitalism)
- best place for innovation
- most desirable location for immigrants
- dominant world language
- world's
The Indian startup ecosystem is on the verge of a once in a generation explosion.
I've invested in 5 companies that are growing like wildfire and want to do A LOT more. Let's talk if you're building for India.
Here's what's going on and why you should pay attention now:
"What does the rest of the world not get about India?"
I asked this question to
@kunalb11
.
Kunal founded
@CRED_club
- a leading Indian fintech valued at $1B+.
This list is a must read if you're interested in Indian startups.
Here were my favorite insights he shared:
Increasingly, my most common advice these days is - put the business books down, lift your head up and get moving.
Build something. Start a project.
No matter how small.
You’ll learn more from being in the trenches and being IN the game vs. standing on the sidelines.
0/ After evaluating 200+ startups this year, I've been in some awesome and not so awesome pitches.
Here are the top 10 mistakes I see Founders make that routinely derail fundraising 👇👇👇
Time to dust off the corporate law textbooks...
"Would Elon win if he sued Twitter’s Board?"
Doubtful. In this case, it’s actually pretty cut and dry.
But this could get a lot more complicated if Elon wanted to make it so.
Here's why:
I’ve invested a few million over the last 5 years into 50+ startups.
I've had some wins but made a LOT of mistakes.
Of all the things not to do - there's one mistake that stands out above the others.
In this thread I’ll break down what that mistake is and how you can avoid it:
Principle
#2
: Stay true to your commitments
If you make a commitment, see it through. Half-assed problem solving creates more work for everyone.
It’s astonishing how quickly you can get ahead if you simply:
A. Say you’re going to do something
B. Do it
C. Repeat
Yesterday was an epic day in sports history.
@RafaelNadal
won his 21st Grand Slam.
Midway through the match, he had a 4% chance to win.
It was one of the greatest comebacks I've ever seen.
Here are 10 observations I had while watching the most tenacious player on the tour:
On Labor Day, I'm reminded that mega-billionaires like Jeff Bezos:
- Created 1.3M+ jobs
- Created $1.6T of value for society
- Captured 1/8th of it for himself
- Is aggressively allocating much of that 1/8th to space exploration
….and everyone is pretty angry about it
Over the last few years, I’ve grown my bootstrapped business to $50M+ in revenue.
The headline sounds great, but it wasn’t pretty.
There was a lot of failure, misstep and doubt along the way.
Here are 20 hard earned (non-fortune cookie) lessons, I picked up along the way:
And the only way you live through those things is you have to ACTUALLY do it.
You have to get on the court and shoot the basketball.
You have to feel the heaviness of putting up your 50th shot when you have 0 energy left in the tank.
That’s how you become a player.
Narrative Violation : “Don’t invest in MBAs”
If you just invested in the HBS Class of 2011, you would have hit $100B+ in market cap.
- Coupang: $60B
- Grab: $17B
- Gojek: $10B
- Oscar Health: $7B
- Stitchfix: $5B
Lesson? Don’t make up “proxy rules” in a game of outliers.
The Domino’s pizza turnaround is one for the ages:
1960: Founded
2004: IPO
2008: Hits record low $2.83/share
2020: Current stock at $391/share (3,000% gain)
The 100x+ growth story is filled with a bunch of lessons for startups today.
Let's dig in.
0/ 2021-2030 will be a Renaissance Decade.
I’m investing $3M this year into startups solving across this spectrum.
Here are the biggest opportunities I’m most excited about. If you’re building in any of these areas, let’s chat.
Let's dig in 👇👇👇
I came across this wonderful piece from
@mbrandolph
, Co-Founder of
@netflix
, the other day. Highly recommend reading it and internalizing it. 5 key lessons I pulled away from Marc’s reflection:
1. Everyone should have a north star - success is what you make of it; money,
When I was 22, I could've made 30% more in my first job.
But I didn't.
Why?
I didn't ask for a raise. I had no clue you could do that!
Early career years are painful. You feel like an idiot 98% of the time.
Here are 20 things about building a career I wish I knew sooner 👇👇
The concepts / strategy of business isn’t what makes succeeding hard.
It’s the emotional steadiness, tenacity, persistence and focus to actually gut it out and will the universe towards an outcome you want.
Over the last 2 years, I’ve grown a bootstrapped business by 8 figures in revenue.
Sounds awesome right? It wasn’t pretty. There was a LOT of failure, misstep and doubt along the way.
Here are 20 (non-fortune cookie) lessons that made me a 10x better leader
[THREAD]
If somebody built an online course on “how to be an adult” they would mint money.
I’m thinking an engaging and easy to understand course covering:
1. Taxes
2. Personal Finance
3. Insurance
4. Healthcare
5. Property Maintenance
6. Etc.
Who is building this?
It’s been two weeks since I launched my newsletter and over 500 unique responses have come in to my question: “What is the biggest challenge you are facing right now.”
Wow! For the foreseeable future, I’ll be answering 2-3 questions a week in a Tuesday mailbag post (in addition
Walt Disney created one of the all time "business vision boards" for Disney in the 1950s:
- Thought through all the network effects
- Connected the dots between 5+ different businesses
- Mixed hardware, software, digital and print
- Understood the specific connectivity between
A few days ago I mentioned I’ve invested $2M in 30 companies over the past year.
Over that same time frame I’ve seen 300+ companies fundraise.
With a few tweaks - a lot of these Founders could raise a lot more.
Here are 20 tips for fundraising 👇👇👇
Principle
#6
: Learn just enough to be dangerous
Know a little bit about: (a) how the world works, (b) how your industry works and (c) how the business works.
Cross functional knowledge is underrated.
If you bring it to the table, you’ll be an asset in any company from Day 1.
To be clear, the point of this thread is not to say “reading, learning about business, etc.” is useless. It is obviously helpful.
But it’s not the straight line shot to your end goal.
The only way you will hit your end goal is by actually getting in the game itself.
Good luck!
Principle
#1
: You’re not the “Strategy Guy”
Yet.
To be a big picture thinker, you have to earn the respect, trust and credibility of your team first.
The only way you can do this is through delivering tangible value.
Focus on bringing results, not laying out frameworks.
Once upon a time:
- Clubhouse was worth $4B
- Hopin was worth $8
- BYJUs was worth $22B
- FTX was worth $32B
- Peloton was worth $50B
ZIRP truly was crazy.
No book, podcast or Twitter thread will simulate how you actually feel when:
- A deal falls apart at the last minute
- A key employee leaves you
- A partner abuses your trust
You have to actually live through those things.
What a privilege it is to be a second generation immigrant.
We get to care about finding purpose, fulfillment, meaning.
Our parents came here and figured out how to survive.
The GOAT "Zero to One" story.
Of all the lessons I've learned in business over the years, there are 5 foundational principles that have been most impactful for me.
I try to set aside time every week to reflect on them and apply them as the basis for everything I do.
Here are the 5 principles + a 15 min
So why do most people read/listen vs. do? I think a couple reasons:
- It feels like progress
- You can’t fail
- It’s intellectually stimulating
The reality of business is most of the work is not glamorous.
It’s a lot of nose to the grind, brute force execution.
Principle
#5
: Figure out what your boss hates and take it off their plate
An exercise I like to do is the “Value Venn Diagram”
- What do I like...
- What am I good at...
- What does the company need..
Figure out what the company needs AND your boss DOESN’T like doing.
There’s a multibillion dollar startup opportunity waiting to be built in religion.
1. Large Market: 6B+ users w/ lifetime stickiness
2. Highly Fragmented: 1M+ communities
3. Low NPS: Terribly subpar product experience
Here’s how I see it playing out…
I am a firm believer that most people can achieve an order of magnitude more than they believe. Over the last 15 years, I have seen so many *normal* people achieve incredible outcomes.
There was a consistent theme that permeated across all of these outcomes: non-linearity
In
The world's most valuable skill:
Clarity of thought.
The problem? There's no school for this.
It takes time, patience and a lot of early career fumbling.
Here are 10 cognitive distortions I faced early in my career and an insight on how to break through each one:
But you don’t.
Even worse, you *think* you do.
Here’s the hard truth: Internalizing all those observations and lessons without having any grounding, context or actual experience is just like WATCHING bball when your goal is to learn how to PLAY bball.
How to build a successful startup:
- Traction
- Speed
- Simplicity
- Consistency
- Community
- Iteration
- Imitation
How to feel like you're building a succesful startup:
- $ Raised
- Investor Brand
- Advisors
- Headcount
- Adulation
- Complexity
Principle
#3
: Get on the scoreboard
Identify the low hanging fruit. This can be for your boss, your team or the company.
It’s obvious, everybody knows it’s there, but for whatever reason it hasn’t been fixed.
Fix it.
Why? It shows momentum and creates a rallying point.
The most important decision you make in your career is where you work.
The problem is most people don't have a toolkit to inform this decision.
Early in my career, I wish I had a guide on how to evaluate a job.
So I put one together.
Here's how to choose where to work:
No book, podcast or Twitter thread will simulate how you actually feel when:
- A deal falls apart at the last minute
- A key employee leaves you
- A partner abuses your trust
You have to actually live through those things.
The cold hard truth:
Why do companies like Quibi raise billions, while companies like Peloton get nothing?
Because fundraising is a GAME
And most people don’t know the rules.
Here are 8 frameworks packed with 50+ hard earned lessons to help you win the game 👇👇👇
Here’s a common pattern I’m seeing more and more amongst young people:
- Get on Twitter and follow “the right people”
- Listen to every business podcast
- Read about all the “frameworks” and “mental models”
In 2020, Apple's AirPods did ~$18B in revenue.
This was more than:
- Paypal ($17.7B)
- Salesforce ($17.1B)
- Kellogg ($13.6B)
- Wayfair ($9.1B)
- Foot Locker ($8B)
- Ralph Lauren ($6.3B)
- Clorox ($6.2B)
- ServiceNow ($3.6B)
And audio is only in the first inning... 🤯
Principle
#7
: Use the “Challenge Framework” to solve difficult problems
Every situation is a function of:
- Incentives
- Personalities
- Perspectives
- Constraints
- Resources
In most “tough” situations, 2+ are misaligned.
Figure out which and hone in on them.
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.
Principle
#2
: Stay true to your commitments
If you make a commitment, see it through. Half-assed problem solving creates more work for everyone.
It’s astonishing how quickly you can get ahead if you simply:
(a) Say you’re going to do something
(b) Do it
(c) Repeat
There’s a multibillion dollar startup opportunity waiting to be built in wealth management.
- Large Market: 600k millennials with $3T+ in assets
- Fragmented: Mix of legacy institutions and 1000+ boutiques
- Low NPS: Subpar product experience
Here’s how I think it plays out: