A couple years ago my company was just valued at $500M dollars…but I was totally burnt out and near my lowest point.
The tool that completely changed my life and how it can help yours:
Man this hits so hard. Like many other founders, I used to hire mostly on pedigree (Ivy League degrees and brand name companies) as a proxy for intelligence. Over the past 6 years running
@PinwheelAPI
, I’ve learned that the most successful teammates are actually the ones who had
Elon Musk rejected this single misconception to build SpaceX into the world-changing company it is today.
The Tyranny of the Or.
What it is and why to reject it:
As an entrepreneur, I've learned that making quality decisions is really hard.
But the best leaders make consistently high-quality decisions, day in and day out.
Here are 7 principles for better decision making:
Just interviewed an absolute killer for an exec role.
3 things he did that really stood out that you should too:
1. Spoke passionately and in great detail about his prior work
He told stories in a way that made me feel emotionally invested and also changed elevation tactfully
My
#1
advice for people early in their careers:
Work at a company that is known for being very well run.
Why?
The biggest difference I've noticed between high performers v. underperformers is that they know what great looks like.
High performers have seen how world-class
I raised my seed round from legendary investor
@joshk
at
@firstround
(early investor in Uber, Square, Roblox and more).
Here's the framework he taught me that helped me grow Pinwheel into a 9-figure biz:
I talked to 8 generational founders whose companies are worth collectively over $50B.
I asked them all one question: what is the one must-have thing you look for when hiring?
All of them gave some version of the same answer:
High Agency
Definition: The ability to deliver the
Patience when hiring is a competitive advantage.
Team quality is the single most important determinant of success.
Don’t hire the B player today—hire the A player in a few months.
It’s painful to wait, but hiring the A player is always the right move. Patience pays.
1. Be Patient When Hiring
Team quality is the single most important determinant of success.
Take your time to build high quality teams.
Don’t hire the B player today.
Hire the A player in 3 months.
Although it’s painful to wait, hiring the A player is always the right move.
If you don’t take care of yourself, you won’t be able to take care of your team or your company.
Build the habits that reduce your highs and lows:
• Exercise daily (no excuses!)
• Meditate
• Journal
• Practice gratitude
The goal is to reduce the amplitude over time.
Most people make one big mistake when it comes to company culture.
Culture is the combination of all the wanted behaviors you reward/celebrate AND all the unwanted behaviors that you tolerate.
Most people are good at doing the former but are really bad at holding the bar high
True story: A VC once gifted me a book called the “Upside of Stress” right after I raised my Series B…
That’s like an NFL coach giving their player a book titled “Concussions Make You Stronger” 😂
So to summarize:
1. Be Patient When Hiring
2. If You Want the Best, Pay the Best
3. Take Care of Yourself
4. First Hires Set the Tone
5. “Move Fast & Break Things” Isn’t Always the Best Approach
6. Don’t Mistake Motion for Progress
7. Make Gratitude & Celebration a Ritual
6. Don’t Mistake Motion for Progress
When everyone is sprinting, it may feel like you’re making a lot of progress.
But beware: motion is not progress.
Ruthlessly eliminate work that isn’t moving the needle on what truly matters.
A rocking chair moves, but never gets anywhere.
2. If You Want the Best, Pay for the Best
Many founders believe they can convince the best talent to take a pay cut by selling the equity dream.
But the best know what they’re worth, and they’ll get it somewhere.
Don’t be stingy.
The ROI on top 5% talent is always there.
The Energy Audit
Throughout your day you are doing things that are either:
1. Giving you energy
2. Draining your energy
3. Neutral
Burnout happens when you are doing more energy-draining v. energy-giving things.
To solve it, you need to first audit your day. Here's how:
3. Take Care of Yourself / Reduce the Amplitude
Building a startup is like a rollercoaster.
One day you’re on the top of the world. The next day you feel like a complete failure.
It’s mentally and emotionally exhausting and can render you ineffective if you don't manage it.
4. First Hires Set the Tone
Your first hires create the cultural blueprint for the company.
If you want a culture that moves fast and is detail-oriented, your early hires need to embody those traits.
Subsequent hires will naturally map their actions to the existing blueprint.
Just met up with a founder of a fast growing NYC startup. He told me he actually applied to be a PM at Pinwheel 3 years ago but we rejected him because he was too junior. 😬
Now he's running a successful startup.
Crazy how one decision can totally change your trajectory...
One of the biggest problems in scaling a startup is ensuring the quality bar doesn’t drop with new hires.
Founders: You will always have the highest bar of anyone at the company. How do you ensure the standard when you can no longer interview every person? Clone yourself by your
One rule I’ve learned:
The “cheap” option is often the most expensive in the long run.
Applies to products, but also to decisions.
The cheap decision—the hack or shortcut—is rarely the right decision.
When you cut corners to “save” you just pay for it later (with interest).
The better approach is to move swiftly but judiciously.
As the saying goes, slow is smooth and smooth is fast.
Move fast whenever you can.
But understand when you need to slow down to get it right the first time.
7. Make Gratitude & Celebration a Ritual
Teams that celebrate together, stay together.
Appreciated teammates are more motivated and work harder.
Build in the rituals for appreciation and celebration early on into your company’s cultural cadence.
You won’t regret it.
Great companies and entrepreneurs are able to avoid this trap.
Instead of choosing between A or B, they figure out a way to have both A AND B.
This is what Collins calls the “Genius of the AND".
The majority of commercially successful people are actually only marginally above average IQ but they're usually extremely high EQ.
Outliers like
@elonmusk
are anomolies, not the norm.
We recently had a big emergency that put our annual plan at risk.
I immediately called my Head of Product. We broke down the problem, game planned different scenarios, and within 20 minutes had a clear plan of action.
After we hopped off, my first reaction was immense
Fast forward to today:
SpaceX rockets are capable of extremely high performance and operate with a significantly lower cost per launch than alternatives.
Musk's rejection of the false tradeoff has sparked a wave of innovative thinking and new innovation in the space economy.
There are really only 2-3 truly critical decisions you make each year that will end up fundamentally changing your trajectory.
If you get stuck in analysis paralysis, ask yourself if it's one of those BIG ones. If it's not, don't sweat it. If it is, slow down and get it right.
5. “Move Fast and Break Things” Isn’t Always The Best Approach
I used to be obsessive with orienting the team around moving as fast as possible.
But we’re not a consumer app.
We’re operating in a highly regulated industry.
If we mess up, it affects people's financial lives.
Important startup learning: Never mistake motion for progress.
When everyone is sprinting, it feels like progress—but it may just be motion masquerading as progress.
Eliminate work that isn’t moving the needle on what matters.
A rocking chair moves, but never gets anywhere.
One of the common ways this materializes is the perceived tradeoff between speed and quality.
Most people assume the faster you build, the lower the quality of the product--and vice versa.
The truth is you can build fast AND with high quality, it’s just a lot harder to do.
But rather than be deterred, he rejected the Tyranny of the Or.
In his mind, this tradeoff--between performance and cost--was a false one.
It was possible to have high performance AND lower cost. It was just harder to achieve.
When you interview key hires, ask them how they contend with the tradeoff between speed and quality (or another common tradeoff).
If they focus on finding the AND, you’ll know you have a great hire on your hands.
Thrilled to be backing
@alvinhsia
and
@emhsia
!
Ethereum users have paid $700M in gas fees just to emit data – Shadow gives crypto teams drop in infrastructure to get more data, save users gas, and ship products faster. Check them out!
A trap that many companies fall into is assuming they must make a tradeoff.
That they can do either A or B but not both.
This is what Jim Collins calls the “Tyranny of the OR”.
It's a critical concept to understand if you are an entrepreneur or builder.
Happy to report that I've gotten over my childhood fear of large crowds and have embraced being a New Yorker. Grateful to be a part of the
@GGVCapital
family and to be building
@PinwheelAPI
in NYC. The energy here is real!
Thx also to
@lucktm
and
@jrichlive
for believing in us!
1/
@kurtisjlin
grew up in the Bay Area, the son of two immigrants and "a huge nerd in every sense of the word." He remembers visiting New York at age 6 or 7, and jokes that he was "traumatized" by the number of people he saw on the street.
#GGVNYC
As a founder, if you don’t take care of yourself, you won’t be able to take care of your company.
Build health habits that compound:
• Exercise daily
• Sleep 7+ hours
• Meditate
• Journal
• Practice gratitude
The goal is to reduce the amplitude of your wave.
Ruthlessly Prioritize Your Decisions
Our brains are only capable of making a certain number of high quality decisions a day.
Use an Eisenhower Matrix to focus your time on the decisions that are most important AND most urgent.
Push the rest to later or delegate/delete them.
TL;DR:
7 principles for better decision making:
1. Classify Your Decisions
2. Ruthlessly Prioritize Your Decisions
3. Minimize Your Regret
4. Avoid “Resulting”
5. Invert Your Thinking
6. Use the Gold Standard Rule
7. Leverage Franklin’s Rule
So how can you use the Genius of the AND in your daily life?
When someone presents you with a tradeoff, first question the foundation of the tradeoff.
Is this real or simply another example of the Tyranny of the OR?
Instead of focusing on the OR, focus on finding the AND.
Builders: Your most important resource is not runway, profit, focus or even time.
It's your energy.
Success takes years. Take care of yourself first.
If you burn out, so will your company.
You need to play the long game if you want to build something great.
Minimize Your Regret
A great way to simplify decision making is to ask yourself:
“In 20 years, will I regret not doing this?”
If the answer is yes, do it.
If the answer is no, don’t.
As a founder, you have a unique responsibility to reject the OR in your startup or company.
You set the tone for how the organization handles perceived tradeoffs.
Win in a competitive market by Creating The Scorecard for prospects.
I used to think marketing was overrated. Like many other first time CEOs, I assumed if you had the best product that you would just win.
After 6 years of running a VC-backed startup from Seed to Series B, I
That’s all for today.
I’m going to be sharing more earned insights from the journey in the weeks and months ahead.
Follow me
@kurtisjlin
to catch this writing in your feed.
PSA: Startups must hire missionaries, not mercenaries.
Things will inevitably get tough and you need people who are committed enough to see things through.
Mercenaries may deliver short-term results but the cost of replacing them (culturally & financially) is too high.
This simple rule has helped me build a world-class team and a 9-figure business in 4 years:
If it's not a hell yes, it's a no.
Team quality is the single most important determinant of success.
Yet, many managers make the mistake of hiring a B player now instead of waiting for
Another example comes from a conversation I had with
@t_xu
in the early days of building
@DoorDash
.
Conventional wisdom was that they could either give you:
More selection of restaurants but less efficient drivers
OR
Smaller selection of restaurants but more efficient drivers
1. Label every meeting on your calendar 1 of 3 colors:
- green: gave you energy
- red: took your energy
- yellow: neither
2. For each day, start at 0 and then add 1 point for each green + subtract 1 for each red (ignore yellows).
3. See how many days are negative v. positive.
One of the simplest and most powerful ways to differentiate yourself is to BRING THE FIRE.
Stand out from other employees by bringing a won't-stop-'til-I-figure-it-out approach to problem solving.
Stand out on a panel of speakers by speaking with unparalleled clarity and
When you’re doing work that truly fulfills you, you’ll feel it in your body.
When you’re not, you’ll feel that too.
Your body always knows before your mind does.
First Round is best-in-class at what they do. Just look at First Round Review, Fast Track, Angel Track, Discovery Assist and all the other innovations they've created to actually be value-add investors. If the past is any indication, PMF Method will be a can't miss for B2B
Most people describe finding PMF as an art, not a science. We're here to change that.
Introducing PMF Method. After 20 years & 500+ investments, we've worked with iconic founders and created a 14-week intensive experience to help B2B founders build epic companies. Apply by 5/7:
Takeaway: Make it a goal to end everyday at least +1. If you do, you'll be making a huge leap towards being fulfilled and energized every day.
If you found this helpful, follow me
@kurtisjlin
and share or RT the first tweet below!
A couple years ago my company was just valued at $500M dollars…but I was totally burnt out and near my lowest point.
The tool that completely changed my life and how it can help yours:
Tony rejected that false tradeoff--it wasn’t actually true.
He looked for the AND, finding you could keep selection plentiful while ensuring efficiency if you remove the time drivers waste waiting around at the restaurant.
That rejection allowed DoorDash to dominate the market.
In the early days of SpaceX, Elon Musk encountered an apparent tradeoff:
Performance of the rockets on one side and cost of the rockets on the other.
He was told by his team that it was impossible to build a rocket with higher performance at a lower cost than existing designs.
Good habits are hard to build. Here's a simple trick to build long lasting habits:
Keep the schedule but reduce the scope.
We all start off with the best intentions by scheduling time to do something good for ourselves: exercise, journal, etc.
But then life gets in the way.
Building fast does NOT imply sacrificing quality. That is a false tradeoff and a losing mentality. You can build fast and with quality--it's just harder to do.
Classify Your Decisions
Jeff Bezos puts decisions into two categories:
Type 1: Irreversible–cannot be easily changed after execution.
Type 2: Reversible–can be easily changed after execution.
Take your time to be right with Type 1 choices.
Move quickly with Type 2 ones.
That's all for today.
If you enjoyed this, follow me
@kurtisjlin
for more content like it as I share insights and lessons from my journey as a founder.
And remember: always question the foundation of every tradeoff. Reject the OR, embrace the AND.
Avoid “Resulting”
High quality decisions sometimes still lead to bad outcomes.
Poor quality decisions sometimes lead to good outcomes.
Don’t bias your perception of whether a decision was good or bad based solely on the outcome.
h/t
@AnnieDuke
Use the Gold Standard Rule
Imagine you were fired from your position and they hired the best person in the world into the role.
What would they do differently?
For myself: If I'm fired as CEO and the board hired Jeff Bezos, what would he change? What would stay the same?
Invert Your Thinking
When problems are hard to solve forwards, they may be more readily solved backwards.
Instead of asking yourself: what are all the things I need to do to be successful at this job?
Ask yourself: if I fail at this job, what will have been the reason why?
Feeling unfulfilled? Here’s a quick hack that might help:
Think back on your life and identity someone who helped you (even if it was in a small way).
It could be a teacher, a coach, a family member, a friend, or anyone else.
Write them a quick note thanking them for
If you're burnt out like I was, I'm willing to bet you're ending the majority of your days below zero.
Let's fix that! Here's a 3-step process to follow:
One common trait that I've noticed every world-class GTM leader I've ever encountered has: they all take lost deals personally.
Since they take every loss as a personal affront, it motivates them to work even harder to make sure it doesn't happen again.
They simply hate losing
2. Reduce the red and increase the green.
Obviously you can't get rid of all the things that drain you. But you can be intentional about delegating or reducing the number of red things you do in any given week.
If you have a day that's -5 and another that is +4, spread it out.
Leverage Franklin’s Rule
Ben Franklin once advised a friend deciding between two job positions.
His recommendation:
(1) List the pros/cons
(2) Assign weightings for each based on importance
(3) Make decision accordingly
Not all pros/cons are the same--focus on the big ones.
1. Identify trends.
Internal meetings, especially HR ones, drained me. So too did 1:1s with certain people.
Contrarily, I got tons of energy talking to customers, recruiting candidates, or jamming on product with my team.
Figure out for yourself what your red and greens are!
The "What Must Be True" Framework
For any company to become a big success, there are a few critical things you must believe will be true.
Here are some examples:
Airbnb
1. People will want to rent their homes to complete strangers
2. People will pick that over hotels for vacay
@jaltma
I really agree with the second point about founder refreshes. It’s awful that the “market rate” for a refresh equity amount is well below the replacement cost of a new CEO.
Worse yet, VCs hide behind that number as their only justification. Then if you threaten to walk away to
Here's how to use this for yourself:
1. Figure out what key things must be true for your biz to be big
2. Create goals and assign metrics to them (e.g. # of drivers for Uber)
3. Anything that doesn’t help you get closer to hitting those goals should be deprioritized
Founders and CEOs: Don’t be afraid to be transparent and lean on your team!
As leaders we tend to think we need to shoulder everything ourselves. If you have good people, they want to help and will be empowered by you trusting them to help solve the co's hairiest problems.
@SahilBloom
LFG! You guys are solving such a massive need in the market. As a lot of startups are struggling to reach profitability, moving some roles overseas is going to be a key cost savings lever to pull.
Hot Take: You should NEVER ship a unloved product if you're a B2B co.
Why?
There's one huge difference between building B2C v. B2B products. With B2B, you can and should be building alongside your customers before you ship.
B2C v. B2B Product Management
Consumers are fickle.
Grateful to have had the chance to sit down with the always amazing
@tjack
to chat about our path to finding PMF. For those founders on the journey looking for super tactical advice, check it out!
3. Create GRG (green-red-green) sandwiches.
If I know I'm doing something draining, I will intentionally sandwich that meeting with a green one before and after it.
This ensures you're going into the meeting with an energy surplus and you immediately refill yourself afterwards!
5. Focus + simplicity = excellence.
Whenever we missed a deadline, it was bc the team was juggling too much or overcomplicating stuff.
1. Give each team exactly one problem to solve at a time.
2. Reduce the scope to minimum prod for delight.
Your shipping speed will go ⬆️!
Hopefully you find these principles helpful in improving how you make decisions. They've certainly helped me!
Follow me
@kurtisjlin
for more on leadership, entrepreneurship, and company building.
It was a real pleasure sitting down with
@sytaylor
,
@siddiquiahmed
,
@FrancesKNeal
and the entire
@FinTechInsiders
team to talk payroll APIs and the potential they have to empower consumers and build a fairer financial system. Check out the episode below!
6. Nothing is ever as good or bad as it seems.
Whenever we signed a big customer I was convinced we were the next big thing.
Every time we had a customer complaint, I wouldn’t be able to sleep for days.
The key is to zoom out and realize 99% of things are not existential.
The hard truth of hiring:
A players hire A players.
B players hire C players.
C players hire D players, etc.
Never compromise your quality bar because you’ll never get it back.
7. Let your team prove you wrong.
I used to be impossible to convince of a new POV.
I would just continue to argue with my team until they saw things my way.
It burnt people out.
If you hire well, you will have great people who disagree with you.
Listen to them! :)
Oof this really hits home.
Every few months, I realize we aren’t moving fast enough and it’s ALWAYS because we’re trying to do too many things.
After 6 years building Pinwheel, this is the most valuable lesson.
Saying no is a superpower.
Focus on the most important thing.