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Martin Luther King Jr.'s original typewritten, I have a dream speech.
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I had read and please feel free to correct this but you've said the most important conversation is the one you have with yourself.
Yeah, so could you elaborate on that please because I think that self-talk is and I'm not sure that's what you're referring to but it's so so terribly important.
So I'd love to hear you just to elaborate on that.
The older I've gotten the more under my mind, I won't do $5,000 for the collectibles.
He had over 100 pieces and I said, Ryan, is there anything I can be doing for you in the next 30 days?
I've always had this theory that if you help enough people get what they want, you'll always get what you want.
So I've never tried to enter a relationship based on selfish motives that if I notice person, I'm going to get these benefits.
So I try to find out what do we have in common as people?
What is it that we can share?
How can I help this person?
No matter how famous they are, how successful they are, everyone has certain needs, even if they're just psychological needs or we all need truth tellers in our life.
So in building relationships, I try to make sure that I surround myself with people who want to see me become better and can help me become better that I can learn from them and that I can contribute to their lives.
And so most of the friendships I have in life, they all started by mistake.
You wanted a young man that's here today that has taught me almost all I know about technology.
I spoke at a clinic in Orlando, a friend of mine, Kevin Eastman was running the clinic and I said to him, I said, who's going to put my presentation up on the screen in that?
You have a IT guy and he said, yes.
And so I said, well, introduce him to me because I want to put my presentation up.
I want to walk to the back at a room and make sure it's clear and so forth.
So I met and I start there.
That's actually how I purchase a book.
When I'm in the bookstore, I have this routine that I go through that and if it passes, I buy the book and if it doesn't, I don't buy the book.
What's your routine? So if I, let's say I'm going to envision this one.
So our office is in El Segundo, which is outside of Los Angeles, banking schools, streets.
He did something for me because he made me feel good.
What she really did is help fortify my mind that I should probably be giving more instead of less.
Well, you've given a lot in a lot of ways in many years of your life and certainly one capacity is that of coach or educator or teacher and we could spend days and hopefully we will.
Hopefully we'll get to know each other even better and spend more time together.
But for now, I thought we might jump forward, at least from your childhood stories to, and that's business books.
I'm just going to be perfectly honest to him.
I often read the beginning of business books and then I never finished them, but you're building and they were like, maybe, I mean, it eventually became like we don't give feedback to direct reports because a lot of people who listen to this or who are watching this have smaller teams.
And my experience is that often people who are good at having these direct conversations in a personal context or a business context are sometimes compartmentalized in their capability in the sense that they're very good, for instance, I think I'm better on the personal side than I am in the business side, specifically when it is team members of mine employees.
If it's with contractors or joint venture partners, I can do that.
For whatever reason, I think it's probably we can also do years of psychotherapy on this, but I feel like with people who are earlier in their career, they're more, I'm all growth mindset, but they're a little more moldable and you can actually coach people out of this as like a way of operating.
If they're later in their career, it's a little more ingrained and it's quite hard, especially because they tend to not be aware of it because they've somehow been successful operating in that mode.
And so they're kind of like, what are you saying?
You see leaders who, and you know how they behave, Tim, is they say, well, if it's not under my direct control, then I am not responsible.
And so they become empire builders.
And some organizations let them get away with it.
They're like, sure, you can have all the infrastructure teams then.
Like, it becomes they grew up.
My parents are both teachers.
My father was a high school English department chair and teacher and baseball coach.
By the way, he would probably say he would stay.
You're like, the points of view are shifting.
Who's the real narrator here?
What is the story? There's not like, you're not being driven by your classic plot or character driven story.
It is much more internal.
It's like John Wick in some sense.
I'm kidding, I'm kidding.
I feel like the plot of John Wick is pretty clear.
You know, I am going to take vengeance.
Excuse me now. I'm going to come out of retirement and kill everyone.
Oh, what a great work of art.
I don't think you have to be a people manager.
But I've come to believe it's the best practice if you are going to be managing people to do your best to write a user manual to working with you.
The idea came to me. Actually, I was moderating a panel at Google.
Google had then evolved to a point where it's trying to celebrate management.
So we've done this great manager award.
And I was the moderator interviewing the great managers that we'd selected across several teams in front of this big room of people at Google.
And I asked them, you know, you ask what are some practices that you think have really benefited you as a manager?
And one of the panelists said, well, I copied this thing that oars.
And this is Oars Holeshole who's along many minutes.
That you're texting me, what's happening?
Me calling me, slacking me, rarely emailing me.
Actually, emailing is really the least interesting channel to them.
So you give guidance, like, what are the best channels, like how to use our one-on-one, but also things like, how do I tend to make decisions?
So if you're coming to me for a decision, here's what you can expect.
If it's this kind of decision, how long will I need, what kind of data might I lay?
Like, I have a section in my doc, which is I tend to be intuitive.
So I've taken a lot of different personality assessments.
And I actually don't really spike in a lot of areas, but I spike as highly intuitive, meaning you come to me with something I intuitively have an opinion.
I'm like, oh, I think this is going to be the right thing to do.
I think I say, I'm intuitive.
And then I write dot, dot, dot, don't worry.
You're available. Should I slack you stuff?
Or should I wait till the next morning?
Or like, you're looking for guidance, you're looking to read the Peeley really feel strongly that you need to process that information and like, have a response.
Whereas for me, I'm like, all the time, I do it all the time.
So email policies, I had a request from Kevin Kelly recently, who's been on the podcast and is a close friend asked me if I could help him with anything, wherever I have a conversation, he said, well, I do have one request.
And it's not for him. It's because he gets asked about it so much.
He doesn't have any issues with email.
But he's like, I want you to ask everyone of your guests about email policies slash rules, systems, anything that they have.
That's one of the things.
And it is a combination of the people and what's being sent to you directly.
So I think that's like a number one rule I have that I'm pretty actually good at.
So there's certain people who feel I'm very responsive on email because I'm very responsive to them.
I'm not maybe responsive to everyone as consistently.
The other is I have, this is like more of a cheat, but you're an investor, I think, right?
So I'm invested in some companies.
And a lot of them send these investor newsletters or investor updates.
And of course, I've, because I do have some Gmail skills, I label them.
I know there's a folder full of them.
And I have every intention to him.
On Friday, I guess, I guess, I'm gonna last two years.
Could you talk a little bit more about how you have used that in your life, personal or professional, how that shows up?
Like examples would be really helpful here so people can really get a grasp on it.
I'm having like almost a physical reaction to relating to you about this calendar.
It's like your past self.
I used to say, oh my gosh, I just mailed myself a letter bomb.
So one is of course, we all strive to improve, which is do not make a decision in the moment about a time or a commitment of resources or time without trying to project your future self.
But of course, we all do because you're right.
We're rushed. We're trying to be responsive.
We're trying to move through our inbox, by the way, because we've only got 30 minutes.
So we might fail the corporate training test.
Or the Japanese TV show.
Don't want to come in last?
Yeah. So one thing is trying to be better about projecting.
And I also, because she's a talented founder, she's persistent.
And she said, why don't you just come and be an observer?
No. Why don't you come to tricky?
I know. I know. Come to the board meeting.
And then she told me why she really needed help in this particular moment.
And there was a situation where having someone who was sort of a friendly, who was neutral in the room was going to be valuable.
So I said, okay, I will come, but I will not like, I really want to set your expectations right back.
I was like, I am not, this is not going to reel me in.
I'm not going to join the board.
And I did go. And she actually convinced someone else.
And look, it's a product that has people's money.
And you need to have good support experiences when something is wrong with any kind of payment.
I'm expecting money. I'm trying to take money.
I'm moving money. There's a high expectation.
And Patrick is like, we need to build 24, 7 global support.
We had really good ambitions.
And by the way, I want to be clear.
One of the things that Stripe has as a value is to be users first.
It is always our most important operating principle.
It is actually deeply in the culture of the company.
So much so Tim, that when the support team would get behind, the entire company would stop and answer support emails.
And so this was becoming an existential problem because we had to do engineering work and other work to build the company.
But we were like, ending up on Fridays before the weekend because you want to get back to people quickly, answering support tickets.
By the way, you hit product market fit, you get traction.
This is a super normal problem to hope to deliver.
What does that conversation look like?
I mean, it's not exactly semiotics, but I know you like language.
And I know you consume a lot of language.
So what is the language that you use to have that conversation, whether it's verbal or in email?
I think you made the connection and then you didn't finish making the connection, but it is so easy to sound like a victim when you are facing this kind of a situation.
And if you're someone who prides themselves on being a player on taking ownership and you've made this commitment and you're like, oh my gosh, there's no way I'm either coming to that meeting or delivering 24, seven global support in six months.
And so what does it look like?
I think what it looks like, the first thing I did that was probably the smartest thing I did when I joined Stripe was I listened and I didn't my first 90 days and I talked to everybody and I heard sort of hears priorities, there's what people need, here's what need my attention.
And then I sat down with Patrick and I said, I'm hearing these four things.
One of them was the support thing, by the way, that really need my attention.
And I am going to rank them.
And then I want you to see my ranking.
And I want to agree on my level of priority.
I said, is I can't make meaningful progress on four things at once.
I can maybe keep and I actually predicted in that moment, I said, because we had to build sales, we had to build recruiting.
We had some internal operational stuff that needed to be fixed.
And then we had this support smoldering fire.
And I said, I think I actually need to build sales and recruiting ahead of fixing support.
But I predict support, this is where when you're working with founders, maybe this is a side, what do you call them side quests?
This is a little bit of a side quest.
Love side quest. But when you're working with founders, people describe this reality distortion experience, which often is more that they have a version of reality and they're like, no, no, we can ship the iPhone in five minutes or whatever, you know, and like everyone's like, yes, Steve, yes, we can.
There's another version of reality distortion, I find, which is you can fix that thing in five minutes.
It's now a joke between Patrick and I, because he'll be like, can't actually make one of ones happen.
So point is, I got in your like, all that organization sounds amazing.
But then do you want to waste an hour of your time and their time learning about it when you realize I don't have time to commit a lot to this organization?
What they would rather have is one, no, it's not on my list of causes that I support.
Or by the way, too, I will give you X amount of money.
You never have to meet with me.
I don't actually have time, but it sounds good.
Here's some money. Goodbye.
And they'll say, well, can you make that commitment for multiple years in a row?
Maybe, maybe not. But I think getting faster at like, there's a pattern here, which is you want my money and my time.
Am I willing to give any money or time?
Yes, no. If I'm willing to get a little bit, just tell them and get out.
Don't have a dog and pony show about it.
Or investments, I just don't really invest in a lot of B to C.
I'll just write back and say, this is not for me.
I don't really do B to C. Good luck.
And they're like, thank you, because they didn't waste their time sending you a deck sending you, you know, they're not chasing the Glen Gary.
So you think you're being an empath by saying, oh, let me hear your story.
This is my trap. My personal trap is, I think I'm being an empath, giving them 30 minutes.
Let me hear your story. And in fact, the empathic thing to do is to say, I'm going to do a probability assessment.
The chance that I'm going to invest, slash, make a donation are sub five percent.
No. No for you. No for me.
And you don't have to think about it ever again.
You don't have to email me tomorrow and ask me again, right?
Like, they're going to keep coming back.
Yeah. Absolutely. I love that.
So glad I asked. And the great answer, also very useful useful answer.
What are some other rules we are going to back the car into the garage of self-awareness?
Because a lot of this pulls at the hem of self-awareness from a bunch of different directions.
But you mentioned that there are certain rules you have because your kid is going off to college and therefore x, y and z.
What are some of the other rules that you have for yourself around what you will or will not do?
Well, I have a rule. This is more of just a self-awareness.
I do get intuitive and I do jump to sort of judgments, conclusions, quickly.
So I have a rule that, like, especially if I'm in a position of leadership and I'm in a meeting and there's other people instead of stating my opinion, I have to ask a question.
Because if you're the senior person and you state your opinion, like, the whole thing is over.
Yeah, right. Yes, Steve, we can ship it in five minutes.
Uh-huh. Exactly. Here's an iPhone.
So that's a rule. Could you give an example of what that would, because you could also ask a question.
Is that being a player enough?
I don't know. Yeah, hitting the snooze button can lead to, like, a delayed 24-car pile-up later.
Profiles of people they're thinking of hiring.
And yeah, that's my hypothesis.
Yeah. So actually, I was going to ask you about the question, when have you seen me do my best and worst work?
But we can come back to that.
We can come back to that.
I'm going to bookmark that.
Maybe we'll get to it. Maybe we won't.
But how should people think about self-awareness?
And I'm just going to share something that I found in the course of doing homework.
And you can certainly fact check this.
But I thought it was quite thought-provoking.
This is from CNBC and I think it was an interview with you.
So this is, you know, if you're not self-aware, how would you know?
That's a hell of a question.
It's kind of like, you know, the tree falling in the forest.
You don't want to hear it kind of question.
Here's some tell-tale signs.
You consistently get feedback that you disagree with.
This doesn't mean the feedback is correct, but it does mean how others perceive you differs from how you perceive yourself.
Interesting. I added the interesting.
You often feel frustrated and annoyed because you don't agree with your team's direction or decisions.
You feel drained at the end of a workday and can't pinpoint why.
You can't describe what kinds of work you do and don't enjoy doing.
So that's setting the table or maybe just peaking people's curiosity.
How would you suggest people think about self-awareness?
Why is this important in the world in which you operate?
I spend a lot of time thinking about how do you get results through people, through teams.
Like, I'm not actually the one building the product.
So I got to do it through kind of brute force human brain power and human time.
And I think that most people who think that way start with the individuals you're managing or the team or the organization.
And my argument is where you're a fan of.
The other is more of a simple one, but Patrick Callison, obviously, who I've worked with, I think I brought him around.
He felt like these things are like horoscopes.
He's like, they're just going to give you a report and it's going to sound like a plausible prediction of you.
And I said, I get it. I get the skepticism.
And I really do, by the way, for anyone.
And actually, I think there's value in getting a horoscope.
How does it actually make me feel?
Like, do I agree with it or not?
What am I really? Like, it actually is part of a process, in my opinion.
Yeah, it's a prompt, like a workshop prompt.
It's a prompt. And how you react to it is interesting, right?
Like, you're like, I really, yes, I am finding love this year.
You know, you know, or am I not?
But, but so point is he then did some research.
And there is the big five personality test is very simple.
It's available for free online as far as I can tell or I've seen.
And it's just these five factors like neuroticism, agreeableness, conscientiousness.
There's one that's sort of entrepreneurial comfort with ambiguity.
Like, whatever. And you can tell a lot from, well, one, the research supports that they're pretty indicative of certain human behaviors.
Sort of decisive, like, no, efficient.
She's very efficient. And sometimes that efficiency is a no, right?
I mean, my version of it is someone who I think is least doing it carefully with others, others like feelings.
I think that I don't love the person who has an assistant, for example, who cancels everything.
No, there's a model here to him.
You've seen it. Where they agreed everything.
And then they have a clean up crew.
Yeah, it's super. They have a clean up crew.
Like the wolf from pulp fiction.
They sent it out to do the dirty work.
Yeah. Yeah. I think what's happening is I'm doing left hand column filtering names of people right now in my mind where I'm like, nope, can't mention them because I think they actually have a clean up crew.
They use the clean up crew.
They use the clean up crew.
Like, like, there aren't that many who seem, I mean, I think you have some good, I think it's in four hour work week.
I don't know if I'm adding that much value, but is the Atlantic, which is private.
So it's easier. But the quality of the people involved, we're doing the business brand stuff, but there's also like, you get to meet these amazing writers and you get to be part of exchange of ideas about the future of democracy.
Yes. You know, that's enriching me.
That's the other thing is making sure there's an exchange in the board of your learning.
You're getting enriched, they're benefiting.
And I don't think it's easy to always get that balance right.
And so you just have to be careful.
I think you just have to be and I think I just didn't realize the level of commitment, not just time, but sort of to do it well.
I mean, it goes back to renegotiating.
So what I'm doing is I'm saying no more boards until I've renegotiated some of my current commitments.
And then we'll see. That's also a very powerful language right there.
Categorically, I'm saying, I have a policy of saying no to X until I have A, B and C.
That's right. It's undil.
And by the way, people can't argue with that because they're like, that's not like a very same thing to do.
But I already managed them is you make sure that they are a priority of yours, even though they are perfectly good on their own, which is the sort of dilemma, right?
Like, how do I help them?
In my book, I still, I mean, I don't steal.
I credit, I source a lot of frameworks.
The book, Scaling People, Tactics for Management and Company Building.
Oh, yes. Thank you. Just to throw it in there.
So there are a lot of QR codes.
You can scan and look at the sites where I reference a lot of materials and books, conscious business, Fred Kaufman's in there.
One framework, I think, I mean, as far as I can tell, I made up myself, was a top talent framework, which is, again, I try to like simplify things, but I think high performers fall into two categories.
And I call them pushers and pullers.
And so the pusher is the one who's like, give me more, give me more.
They're often wanting to get more comp too.
But they're like, I want recognition, I want responsibility, I want scope, I want to move the needle, I'm high impact.
They're very impatient with themselves, with other people.
They can be a little high friction for the team because they're like, going for it, grabbing it, grabbing it.
But, you know, it's fun because you load them up and they're just like carrying the whole thing up the hill without you.
But they can be tough. My main coaching often ends up with them is saying, until I believe that the people working with you love working with you, I don't think you're succeeding.
And they're like, why? Because they're all keeping score.
But they're keeping score in the sort of maybe early in his life, Tim Ferris version, I don't know.
No, that's fair assessment.
I mean, I think I am a pusher as an entrepreneur for sure.
And that I've learned how that can be a liability.
They can be a huge superpower and they can be a huge liability.
Right. And your job is to sort of like I say, you know, giving direct feedback is holding up a mirror and just being like, here's the beauty of you.
And here's the liability part.
And if you can't show me that you can work on the liability part, I can't keep loading you up.
Because in the case of the pusher, yeah, they might burn themselves out, but they actually like burn out the people around them.
So that's the pusher. So the polar, it's funny.
This happens to be in a couple of conversations I've had is I'm usually being interviewed by someone who's like the pusher.
I'm the polar. But anyway, I'm the polar is someone who no complaints, you load them up and they're like, yep, yep, I got it, but they're not asking for it.
They're not grabbing it.
They're not pushing, but they're highly confident.
They're very organized.
They're very consistent, reliable.
And they have good judgment.
And you're like, okay, I know that person won't screw that up.
I know that person will get the people to the party and that, you know, whatever it is.
And you just start loading them and they don't renegotiate.
They don't know how to say no.
And then they explode. Like they basically implode or exit.
That's what I've run into with past employees.
Yep. And there's some like I went through a period of my own development where I was like, I think of it as my martyr period where I literally, I don't know who I thought I was bartering myself for like everyone else.
I would be doing all this stuff for my colleagues, for my team.
And I was like, no one appreciates like, I don't know.
And I eventually had a really good open conversation with a guy, not my boss who worked with me.
And he's like, did I ask you to take that on?
Like you to start running that project or you run our planning process or like, did someone ask you?
And I'm like, well, no, no one was doing it.
So I'm doing it. And I was like, hmm.
And he's like, and why?
