Welcome to the final episode of 2025.
I pulled together some of my favorite moments from the year.
These conversations helped me think better, work smarter, and live with more intention.
It's time to listen and learn.
Toughness, kindness, and clarity.
All three.
But don't forget the toughness.
Because you don't want yes people around you.
You want people who say, why don't we push the boundaries of our thinking?
AI makes me get to the answer perhaps more quickly, but you need someone with experience to know which of those references matter to the business.
I am genuinely concerned that, because of different societal factors, because of people who maybe lost out on some social skills during the pandemic, there is not that rejection resilience that many of us need in life.
You mentioned that we can engineer trust.
How do we do that?
One is repeated exposure.
Second is establish a set of shared values.
Everything is here to teach me and help me.
It's all working for my good.
So we're going to go look for those moments when you're most uncomfortable and remind yourself this is my teacher from when a customer orders something when it gets through the distribution center.
How is it going to be picked, packed, packaged, and shipped?
And when you look at that from a flow perspective, you start thinking about new solutions.
Getting really, really comfortable with being uncomfortable is magic.
And I wasn't always good at that.
The right entrepreneurs, the best entrepreneurs, they just simply out-care other people.
When you talk about inputs versus outputs, what inputs do you think about in life?
Well, I think the inputs I think about are.
You know, it depends on what I'm trying to get accomplished.
But if the inputs are just thinking about hard work, do I get up every day?
If I want to stay healthy, do I get up every single day and work out?
I hear that you work out every single day because, instead of trying to figure out which days you're going to work out, it's always a negotiation with which days and some days you don't feel like exercising.
You just work out every day.
I have the same philosophy.
You just get up every single day and do the things that are important.
So the inputs I have is I get up every morning, I work out, I read through my email and I try to think about what's the most important thing that I have to get right today.
And think about first order issues.
What is the first order issue that I have to solve?
What is the first order issue of a company that That needs to get fixed.
What is the thing that I need to do to influence an outcome for a founder?
And that's very, very clarifying.
Often we can create a very, very long to-do list and then you've got to pop up a level and just look at the to-do list.
What's the most important things I have to get accomplished?
Because if you just list all the to-dos, you probably will not be able to get to all of them.
And the most important thing might be the last one you list.
And so you can't just go down that list and do them one by one.
Often it's by popping up a level where you sort of look at the whole list and it's like okay well, most of this is not important.
Is that what you mean by first order issue?
I think you mean something a little more nuanced.
Some people talk about the most important thing.
And I think about... first order.
If I get this problem, I have a problem on my hands.
If I get to the first order issue and get to the root cause of that, usually that helps solve that problem.
And there are other issues that are not first order.
Um, and that concept is quite important.
And we also sort of navigate that into other situations where, um, where they are crucible blown.
So as an example, you have situations where the website's not working fast enough.
At Zappos, we had a situation where the website's not fast enough.
Is the first order issue that we have too many pictures?
Well, we want the pictures.
We have lots of photos.
We want to show those photos.
Is the first order issue that we need to trim the number of search results?
Well, customers want longer search results.
It's like, no, it's none of that.
We need to figure out how to make the website go faster.
And so we start caching.
The search results, we start caching things.
And so you start developing the technologies that solve the speed issue.
But the first order issue is that we need to solve this with technology, not with a bunch of either or solutions.
That's an example that I learned a long time ago.
Another situation is the distribution at Zappos was not flowing well and we couldn't figure out which process was broken.
Was it the picking process?
Was the ordering process broken?
What was broken about it?
And we went and just looked through the flow, and the flow was broken.
And so there was too many handoffs across all of these different discrete processes.
And so we have to sort of pop up a level and figure out what the flow of from when a customer orders something, when it gets through the distribution center, how it's going to be picked, packed and packaged and shipped.
And when you look at that from a flow perspective, you start thinking about new solutions that allowed there to be much better flow throughout the distribution center than to batch things for picking, batch things for packing, batch things for shipping.
That's what you mean by first order.
I want to get into more of your experience, not only at Zappos, but being on the board of some of the companies that everybody has heard of.
And today are being involved.
But before we get there, I want to come back to the school for a second.
Are there any other experiences that you had during school with teachers that might have impacted you?
You know, earlier on in junior high school I was um.
I was suspended from the computer lab because I built uh, this was very old.
So they're a radio shack TRS 80s.
So we call them trash 80s today.
Um, and there was the computer lab.
You know you had to rent time in our computer lab to to use the computer.
And I built this game and the central server at the time was literally a floppy drive where all of us saved our programs there.
And one day a bunch of the students in the computer lab all found the game that I programmed and then started playing with it.
The teacher and the principal just happened to walk in and saw that we're all playing this game.
And I was told that Computer lab is valuable time and you should be doing something much more productive than producing a game.
So I was no longer allowed to work in the computer lab.
And the computer lab teacher was Mrs. Pitosa and she also ran the math team.
And she said well, I'm sorry, the principal wants you out of the computer lab, but you should join the math team.
And I joined the math team there.
And one of the things I was very good at was math.
And she told me that if you want to be a leader and you want the team to win, it's not good enough for me to just solve the problems.
Figure out how to get the rest of the team to perform.
And so I started teaching the rest of the math team some of the reasons why I was able to solve some of these problems more quickly than they were.
They're very talented, but I had figured out tricks that they had not figured out.
And they taught me tricks that I had not figured out.
So we got better and better by riffing off each other.
And so I learned the value of teamwork by just being thrown into a situation like that such an interesting front row seat into what's happening.
Do you think founders go astray when they start listening to too many outside voices?
And this goes back to the i'm sure you're aware the brian chesky.
You know the founder mode.
Do you think talk to me about that?
I have such a nuanced point of view on this because it is decidedly not simple.
Uh so, Broadly speaking, I really like the spirit of founder mode, which is just having deep founder-led accountability for every decision at your company.
I think that that's how great companies operate.
And when you proverbially make decisions by committee or you're more focused on process than outcomes, um that produces all the experiences we hate as employees as customers you know that's the proverbial dmv right you know it's like process over outcomes um and then similarly uh you look at the disruption in all industries right now because of ai you know the companies that will recognize where things are clearly going to change like everyone can see it it's like a you know slow motion car wreck everyone knows how it ends You need that kind of decisive breakthrough boundaries, layers of management to actually make change as fast as required in business right now.
The issue I have not with Brian's statements, Brian's amazing is how people can sort of interpret that and sort of execute it as a caricature of what I think it means.
You know, there was a I remember after Steve Jobs passed away and, you know, I don't know.
I've met Steve a couple of times.
I haven't never worked with him in any meaningful way.
You know, but he was sort of if you believe the story is like kind of pretty hard on his employees and very exacting.
And I think a lot of founders were like mimicking that you know done to wearing a black turtleneck and yelling at their employees.
I'm like, I'm not sure that was the cause.
You know, I think Steve Jobs' taste and judgment through you know, executed through that, you know packaging was the cause of their success.
And Somehow, and then similarly, I think, founder mode can be weaponized as an excuse for, just like overt micromanagement.
And that probably won't lead to great outcomes either.
And most great companies are filled with extremely great individual contributors who make good decisions and work really hard.
And companies that are like solely executing through the judgment of individual probably aren't going to be able to scale to be truly great companies.
So I have a very nuanced point because I actually believe in founders.
I believe in actually that accountability that comes from the top.
I believe in cultures where founders have license to go in and all the way to a small decision and fix it.
The infamous question mark emails from Jeff Bezos, that type of thing.
That's the right way to run a company.
But that doesn't mean that you don't have a culture where individuals are accountable and empowered.
And you don't want uh, you know people trying to decide, make business decisions because of what will please our dual leader, you know, which is like the caricature of this and so you know, after that came out, i could sort of see it all happening, which is like some people will take that.
I'm like you know what you're right, i need to go down and be in the details and some people will do it and probably make everyone who works for the miserable, and probably both will happen as a consequence.
So totally thank you for the detail and nuance there.
I love that too.
Do you think engineers make good leaders?
I do think engineers make good leaders, but one thing I've seen is that I think that I really believe that great CEOs and great founders um, start usually with one specialty but become uh, more broadly, specialists in our parts of their business.
Um, you know, I think the uh Businesses are multifaceted and rarely is a business's success due to one thing like engineering or product, which is where a lot of founders come from.
Often your go to market model is important for consumer companies.
How you engage with the world and public policy becomes extremely important.
And I think, as you see, founders grow from doing one thing to growing to be in a real meaningful company like Airbnb or Meta or something.
You can see those founders really transform from being one thing to many things.
So I do think engineers make great leaders.
I think the first principles thinking the system, design thinking really benefits things like organization, design strategy and.
But I also think that you know when we were speaking earlier about identity.
I think one of the main transitions founders need to make, especially engineers, is you're not like the product manager for the company, you're the CEO.
And at any given day, do you spend time recruiting an executive because you have a need?
Do you spend time on sales, because that will have the biggest impact.
Do you spend time on public policy or regulation?
Because if you don't, it will happen to you and could really impact your business in a negative way.
And I think engineers who are unwilling to elevate their identity from what they were to what it needs to be in the moment often leads to sort of plateaus in companies growth.
So 100.
I think engineers make great leaders and It's not a coincidence, I think that most of the Silicon Valley great Silicon Valley CEOs came from engineering backgrounds.
But I also don't think that's sufficient either as your company scales.
And I think that making that transition as all the great ones have is incredibly important.
To what extent are all business problems engineering problems?
That's a deeper philosophical question that I think I have the capacity to answer.
What is engineering?
What I like about approaching problems as an engineer is first principles thinking and understanding the root causes of issues, rather than simply addressing the symptoms of the problem.
And I do think that, coming from a background in engineering, that is everything from process, like how engineers do a root cause analysis of a outage on a server is a really great way to analyze why you lost a sales deal.
You know like i love the systematic approach of engineering.
One thing that i think going back to good ideas that can become caricatures of themselves like one thing i've seen though, with engineers who go into other disciplines is um, Sometimes you can overanalyze decisions in some domains.
Let's just take modern communications, which is driven in social media and very fast-paced.
Having a systematic first principles discussion about every tweet you do is probably not a great comms strategy.
And then similarly, you know, there are some aspects of say, enterprise software sales that you know aren't rational but they're human, you know.
Like forming personal relationships, you know, and the importance of those to building trust with a partner.
It's not all just, you know, product and technology.
And so I would say I think a lot of things coming with an engineer mindset could really benefit, but I do think that taking that to its logical extreme can lead to analysis paralysis, can lead to over-intellectualizing some things that are fundamentally human problems.
And so yeah, I think a lot can benefit from engineering, but I wouldn't say everything's an engineering problem in my experience,
You brought up first principles a couple of times.
You're running your third startup now, Sierra.
It's going really well.
How do you use first principles in terms of how do you use that at work?
Yeah, it's particularly important right now because the market of AI is changing so rapidly.
So if you rewind two years, you know, most people hadn't used ChatGPT yet.
Most companies hadn't heard the phrase large language models or generative AI yet.
And in two years you have ChatGPT becoming one of the most popular consumer services in history, faster than any service in history.
And you have, across so many domains in the enterprise, really rapid transformation.
The law is being transformed.
Marketing is being transformed.
Customer service, which is where my company, SierraWorks, is being transformed.
Software engineering is being transformed.
And the amount of change in such a short period of time is, I think, unprecedented.
And perhaps I lack the historical context, but it feels faster than anything I've experienced in my career.
And so, as a consequence, I think, if you're responding to the facts in front of you and not thinking from first principles about why we're at this point and where it will probably be 12 months from now, the likelihood that you'll make the right strategic decision is almost zero.
So, as an example, it's really interesting to me that With modern large language models, one of the careers that is being most transformed is software engineering.
And one of the things I think a lot about is how many software engineers will we have at our company three years from now?
What will the role of a software engineer be as we go from being authors of code to operators of code generating machines?
What does that mean for the type of people we should recruit?
And if I look at the actual craft of software engineering that we're doing right now, I think it's literally a fact that it'll be completely different two years from now.
Yet I think a lot of people building companies hire for the problem in front of them rather than doing that.
But two years is not that long.
Those people that you hire now will just be getting really productive a couple of years from now.
So we try to think about most of our long term business from first principles, everything from.
I'll say a couple examples in our business.
Our pricing model is really unique and comes from first principles thinking rather than having our customers pay a license for the privilege of using our platform.
We only charge our customers for the outcomes, meaning if the ai agent they've built for their customers solves the problem, there's like a usually a pre-negotiated rate for that, and that comes from the principle that, in the age of ai, software isn't just helping you be more productive but actually completing a task.
What is the right and logical business model for something that completes a task well, charging for a job well done rather than charging for the privileges using the software.
Similarly, you know we with a lot of our customers.
You know we help deliver them a fully working AI agent.
We don't hand them a bunch of software and say, good luck, configure it yourself.
And the logic there is.
In a world where making software is easier than it ever is before and you're delivering outcomes for your customer, the delivery model of software probably should change as well.
And we've really tried to reimagine what the software company of the future should look like and trying to model that in everything that we do.
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Do you think we've sort of broken dating in a way where I mean I've been on dates with people.
We all know people who are.
I wish people would come up to me and ask me out.
I wish I didn't have to use a dating app.
And my defense of you know.
Thinking immediately in this is like society has taught guys not to approach women anymore.
What's your reaction to that?
This is something that I'm thinking about a lot, specifically with Gen Z and Gen Alpha.
So I was recently speaking to somebody.
She's a 16 year old entrepreneur and she's trying to deliver help for teen daters.
And she said by far the number one thing that she gets questions about is how to deal with rejection.
And so I am genuinely concerned that, because of different societal factors, because of people who maybe lost out on some social skills during the pandemic, because of people who live a lot of their lives online,
There is not that rejection resilience that many of us need in life.
So if you want your dream job, you need to go out there, get a lot of no's and go after it.
You don't just sit at home waiting for a LinkedIn recruiter to message you about your dream job.
That doesn't happen.
You have to make it happen.
And the same thing is true with dating is that you have to shoot your shot.
You have to approach people in public.
You have to take a risk.
And so I'm encountering a lot of people who are very afraid of rejection and are not taking those risks.
And I think that it's leading to fewer relationships.
I'm a make it happen kind of person in work and in life.
I also know that that can come off as aggressive or assertive.
How do you deal with that?
That's interesting.
So what's a scenario that you feel like could come across the wrong way?
Well, make it happen is like you have a great first date or something, and then you're instantly like on to the next date.
You know, you're like, I want to see you again.
How about tomorrow?
And then the other person, I don't know like.
I feel like we're just in a society now where you know you're supposed to wait till tomorrow, almost.
And I hate personally waiting.
I'm sure there's other people out there like me, too.
Where it's like, no, you're in charge, you have agency, and you can make the world happen.
I love this question because I think it speaks to a really real phenomenon, where people are experiencing excitement about somebody, but they feel like they need to hold it back to seem cool.
And so...
I love to talk to people about attachment theory.
Has that come up on your podcast?
No, let's go into it.
OK, so attachment theory is something in the world of relationship science that's truly backed by the research.
It's something that first came about around 60 years ago with someone named John Bowlby.
And this research was originally done with children to see their attachments to their primary caregiver.
But now we have an entire field of adult attachments specifically around relationships.
And so there are people who are anxiously attached.
What happens for them is their story of love is that I'm going to chase you.
I have to convince you to like me.
You might pull away and we're going to have this chase dynamic and that I'm constantly worried that you're not going to be interested in me and you're going to disappear.
So how those people show up in relationships and I know, because I really was one of these daters is if you don't hear back from somebody, you start spiraling.
They met somebody else.
They don't like me anymore.
You send a bunch of texts to try to reconnect with them.
And you're often just in this danger zone where you're not being the person that you want to be, because you're trying to have this reconnection moment.
You think somebody is going to pull away.
Then there's people who are avoidant attached. they sort of have the opposite experience.
Their version of love is I'm going to be smothered.
I'm going to lose my independence.
And when they get too close to somebody, they are the ones pulling away.
So they're the ones you know.
Great sleepover on a Saturday night.
Sunday morning they wake up the person hasn't left.
And they're like, damn, should I call her an Uber?
Oh my God, that's me.
That's you?
Yeah.
You have that feeling of like, I need my space.
Well, I need my space and I don't want to get hurt.
There's like an element of, Absolutely.
What you're talking about is complete true.
It's not that those people don't want to be in intimate connection.
It's that the fear of being smothered or the fear of being hurt causes them to pull away.
I'm going to reject you before you reject me.
And so for those avoidant attached people who think that they're going to be smothered.
And then for the anxiously attached people who think they're going to be abandoned.
What ends up happening is they often date each other and they reinforce this idea.
So I think that love is a chase.
You think that love is being smothered.
So when I go after you, you pull away.
That reinforces mine and that reinforces yours.
And anxious, attached, and avoidant people keep dating each other in this anxious, avoidant loop that leaves both people feeling pretty unhappy.
But there's a third type of securely attached people.
And these are people who have a healthy relationship with independence and with intimacy.
I want to be close to you, but I also respect and need my alone time.
And so often the way that people get out of the anxious avoidant loop is they either become more secure themselves or they date someone who's secure.
And so that's what happened for me.
After you know, 10 years of Chasing after different people being rejected, being disappointed, thinking well, if only I could prove my value, then this guy would like me.
Instead, when I dated somebody who was secure, it broke a lot of those patterns and we formed what I feel like is my first really healthy relationship.
What happens is 50 of the population is secure, which sounds like a good thing, but those people are so good at being in relationships that they often get snatched up and you have the anxious and avoidant people dating each other.
But in the example that you described, it can actually be very secure for somebody to follow up after a date and say hey, I really enjoyed getting to know you.
I'd love to see you again.
When are you free?
And in that moment, somebody who's used to dating somebody who's avoidant might be like whoa, they're coming on too strong, or that's so obvious.
They're so obviously interested.
That's boring.
But a ton of the work that I do is training people to identify secure partners and to reestablish them in their heads not as boring but as secure, and to know that those are the people to go after.
So sometimes that person who pulls away is exciting, that sparky feeling, because you don't know if they like you or not but instead really honoring the person who says I like you.
I'm interested.
When can I see you again?
And so the slight tweak that I would have to yours is not I like you.
Can I see you tomorrow?
That does kind of feel a little bit intense.
But being clear about like, hey, that was a really great date.
I feel like we really connected.
I'd love to see you again.
And then like working together to come up with the next date.
And a lot of dating that people miss is that it's about matching somebody's momentum and matching somebody's speed.
So it's a dance where I take a step forward and then you need to take a step forward.
If I take 10 steps forward, you might feel overwhelmed and take a step back.
So just paying attention to are you always the one reaching out?
Are you always the one making plans?
There needs to be momentum matching for the speed to feel right to both people.
Well, I think the big thing about preparation and success is the price has to be paid in advance.
You have to put in the work before you get any results.
So there's no way to honestly know how good your preparation is or isn't.
That's why I always try to emphasize, keep preparing, keep working.
Um, you don't know what the other guy's doing.
He might be, you know, working just as hard as you are.
And that preparation, you know it can't be after the fact of like Oh, I wish I would have studied more.
It's too late at that point.
You have to do it on the front end.
So, um getting in condition um, you know studying, preparing all your film and your opponents, and all that, like those things are, are all have to be done on the front end.
And A lot of times there's, I would say, a little bit of a tendency to just sort of let up on the preparation.
Well, I've watched some film.
Well, I've done some extra sprints.
Well, I've done this.
I've done that.
Well, is that enough?
Is it really enough?
If you do more, will it make a difference?
Not to the point of diminishing returns, but to the point of comprehensive preparation.
So that's really what we try to emphasize on that.
The way that I think of it, that is sort of the pain of losing is sharp, but it's over fairly quickly.
But the pain of regret, not putting in the work, not doing the things, you didn't leave it all in the field that lasts forever.
Exactly.
That's exactly it.
The pain of regret is much more than the pain of preparation.
Absolutely.
I think you had a 24 hour rule sort of after winter losses, you have 24 hours to think about it and then you move on.
Is that?
That's right.
Yeah, you play the game, you go back, you analyze it.
What do we do well?
What do we do poorly?
What do we need to do better?
What adjustments should we have made?
What coaching errors did we make?
And so forth.
And then you factor all that into, you know, how does that affect this next week?
Sometimes there's a lot of carryover.
Sometimes the team you play the following week is completely different.
And some of those lessons may not really become applicable for a week or two weeks or three weeks until you see a, you know, a similar type of opponent um, say like a scrambling quarterback.
You know, maybe you play two or three weeks where those quarterbacks aren't too mobile.
And then when you get up against another scrambling quarterback, you go back and look at a.
How you know how?
How do we need to handle this better?
Uh, against this type of an opponent.
So um, but yeah, you look at all those things after 24 hours win or lose or draw uh you, you Take your lessons and you decide how you're going to incorporate any of those things into this week's preparation and practice, what we're going to do differently or maybe do more of or do less of whatever it is.
And then you're done with that and you move on to your opponent and spend the next five days six days, whatever it is of, just you know, digging in on that opponent and what they do.
Talk to me about the relationship between the best talent in the world and you know, you're playing in the NFL, you're coaching in the NFL and confidence.
Well, again, it's all relative.
You know Shane, I mean as good as the players are in the NFL.
The guys on the other side of the ball are pretty good too.
And you know, I'd say every team, generally speaking, every team has about, you know, five or six players that are elite, have elite payments, elite contracts.
And then you might have some younger players in their first through fourth year.
You know two or three four, whatever those that are elite players.
They just haven't hit those top contracts yet.
But they don't necessarily match up in the same position.
You might have a tackle, I might have a guard, you might have a linebacker, I might have a corner, and so forth.
So The way those elite players match up is very specific from game to game, and how you want to match them, your matches against theirs, and how you want to deal with that is a big part of it.
I think the confidence thing is really interesting.
I think what really separates the great players is their ability to do it even when the bullseye is on their back every week, like it was with Tom Brady, like it was with Lawrence Taylor, like it is with Patrick Mahomes, like it is with players like that Lamar Jackson and so forth.
Every week, the teams are geared towards stopping those players and game planning against them or putting their best guy on them, or however, you're going to handle them.
And for those players to continue to be productive in spite of the game plan.
Attention they get is what truly makes those players, you know, great and elite.
And I think that you know when we had Kobe Bryant come in and talk to our team I think it was around 2018 19, somewhere in there
And you know, Kobe talked a lot about evolving, you know, and he said you know look, when I was 22 23, you know, I could just get the ball and drive by anybody and score.
He said, I can't do that anymore.
I still score, but I found different ways to score moving without the ball, jump shots and, you know, being better in pick situations and all those kind of things that you know he said I found I found ways to evolve my game because I just couldn't do the things I used to be able to do as well.
But there are other things I found that I can actually do better.
And I thought that was a great message for all of us to hear that, as we, you know, as we go through our careers, do the things that are working, do the things that you can do well, but also evolve, continue to learn, continue to, you know, find ways to be productive that are maybe a little out of your comfort zone or are not, you know, habitual for you now.
But if you can become good at them, they can be great, you know, great tools for you.
Are there any other people that you brought to speak from sort of different sports?
That sort of had a different message that resonated with you or the team and just stands out in your mind?
Oh, yeah, we had a lot of them.
Yeah, we had a lot of them.
And it was great because you know just the guys.
You know they hear a lot of football stories, but it's good to hear all the ones.
One of the ones I thought was particularly entertaining, a couple of them, one was Paul Asciante.
They won like 14 national championships in a row.
They won like 160-some games in a row, matches in a row.
I mean, at the Patriots, we were favored in almost every game.
You know, not every game, but most every game for quite a while.
And so, you know, I brought Coach Asciante and I said you know, here's guys who won like 13 straight national championships.
They won 160-some matches in a row.
I mean, you talk about being favored now, like they're favored.
And, and, and like, let's listen to what that's really like.
And he was great.
He talked about, it doesn't matter whether you are or aren't or how many you have or haven't won.
Every day is an opportunity.
You make the most out of each day and you just get better each day.
And you don't worry about what you've done in the past.
You just, you look at today's opportunity and make the most out of it.
It was great.
So one of our coach, one of our players, sticks his hand up and said Hey coach, I have a question.
What's squash?
I thought it was a vegetable.
And Jimmy Johnson.
You know we were going into the playoffs and Jimmy came up and he was doing a um uh, you know a story on somebody.
And I said, Hey, would you mind, you know, talking to him?
So he said, yeah, let me tell you a little playoff story here.
You know, when I was in Dallas, we were getting ready for the playoffs and We're in a special teams meeting.
I'm standing in the back and I see I see one of our, one of our players back there kind of dozing off and not paying attention.
And he said he wasn't a he wasn't a starter, but he played in special teams.
And he said it just really annoyed me.
And so I went over, I flipped on the lights, turn the lights on the meeting.
And I went over to him.
I said, that's it.
You fall asleep in this meeting.
We don't want you.
This is your primary job.
Take your playbook and go see his general manager.
You're done.
You're cut.
And everybody's like, whoa.
That woke everybody up.
It was right before the playoffs.
So, any questions?
Yeah, Coach.
What would you have done if that had been Troy Aikman?
Jimmy said, well, I wouldn't have turned on the lights.
I probably would have gone over to him and nudged him and said, hey, Troy, pay attention.
And The message was, if you have a lot of pelts on the wall, you might have a little more slack.
If you don't have a lot of pelts on the wall, you don't have any room.
You don't have any room.
You can't live on what you've done because you haven't done enough.
You better know where you are.
And if you're Troy Eggman and Tom Brady, but he goes, those guys would never do that anyway.
But you might be able to survive that.
But if you don't have that kind of resume, you haven't had that kind of production for this team.
Nobody wants that.
You're replaceable.
They'll find somebody else who will stay awake in the meetings and who will be more attentive.
And it's pretty funny.
I just nudge them and say, hey, pay attention.
As a leader, you've called yourself blunt and direct when delivering a message to people.
I'm curious what you've learned about delivering a message that gets heard.
You know it's an evolving process, if you want to call it that.
Sometimes people deliver messages that are not heard because you haven't really delivered the message clearly.
People actually come out of performance appraisal and say, I think I'm doing a good job.
And you're going, oh my God, I hope that's not what you heard.
You're saying to yourself, because this person was supposed to have told you the three or four things areas that you're supposed to improve upon and the three or four things that you did wrong.
You're supposed to have gotten very direct feedback.
People don't like conflict.
People don't like to deal with issues directly.
They like to beat around the bush and then leave saying, I think I gave the person the message.
I had the opposite perspective, which is give the message, do it in a supportive way And make sure that whatever you tell them they have to work on, you help them get to that.
So I chose to write performance appraisals which said, this is what you've done well.
This is where I think you didn't do well.
This is what you need to work on.
And if you were to work on these issues and show progress, this is where you could go.
So, you see, what this letter did was celebrate them for what they did well, told them what they didn't do well, Told them the three or four things they had to demonstrate progress on in the next year and how I was going to help them.
And then also told them, if you showed progress, this is your trajectory.
Because if we don't do it, I think we're not getting the best out of people.
There's a kindness and clarity.
Toughness, kindness, and clarity, all three.
But don't forget the toughness, because you're confronting them and saying you know, I asked you to really get to know the international markets.
You made two trips internationally last year, and each trip in three days you came right back.
How could you have learned international markets without getting out of the office in the U.S.?
?
OK, and then you write saying, I'd like you to visit the following countries next year.
And when you visit those countries, make sure you go down to this level of detail.
You know, some people would say a CEO shouldn't be getting to that level of detail.
Yeah, they're right.
But if I truly care about this executive and I think they have great potential, I will get to that level of detail.
And I will monitor it middle of the year and say, hey, did you make any international trips?
Did you follow anything I said?
And if they say, no, I really don't want to go, then you go there.
You know, you don't have the potential to be a CEO.
From the outside, we hear these stories about how CEOs pay attention to the top 50 of the top 100.
How many people inside were you really monitoring and trying to develop and having a personal, a real one-to-one personal relationship, where you're doing this and you're in the weeds and you're in the performance report and you're trying to build them?
I think there's about three or four hundred that were corporate assets.
And one watched them all the time because these are people who in 15 years could be CEO.
There's something about them that you know.
You sort of caught your fancy when you were in a meeting or in some project that they were on.
They had brilliant ideas, not brilliant ideas that reinforced your thinking.
Brilliant ideas that challenged your thinking and took us to a better place.
Because you don't want yes, people around you.
You want people who say why don't we push the boundaries of our thinking?
What if we approach this creatively?
And people will put the company before themselves.
I look for that all the time.
And so there are 300 or 400 people that we actually call them corporate assets and we track them to make sure that we game plan them, give them the right assignments.
And even if they couldn't move, Could we give them interesting assignments so that they could get the experiences without constantly moving?
So that's the number of people that we tracked.
What were the signs that somebody was putting the company ahead of themselves?
They would put their hand up for difficult assignments.
And if something went wrong, they didn't look for somebody else to blame.
They would take the blame and say hey, you know, I could have done a different job, or I could have led differently, or I could have staffed my team differently.
These are people who would come to me and say you know, whatever's going on in this other part of the company.
I think may be putting something in jeopardy.
And I'm not throwing them under the bus.
Would it be okay with you if I went and worked with them to perhaps write things?
And I said, be careful how you do it, but go for it.
And I will tell them that I didn't send you there, that you were doing it out of your own good nature.
Otherwise, people say, oh, the CEO's got some pets that she's sending our way.
So you've got to be very careful how you deal with organizational dynamics.
But These are people who look around themselves and are constantly looking for ways to improve the company, as opposed to how do I get the next promotion, the next raise?
You said a lot of people don't read the footnotes or the financial statements.
Is that changing in a world of AI, where you can sort of like, download the financial statement, pop it into AI and say what do I need to know?
I think it's actually exacerbating the situations.
Oh, spend a few beats on that.
Because now, read the financial statements, Anthony.
I just put it into AI.
I asked ChatGPT to tell me, what about this?
Look for that.
Look for that.
And there's all the instances of those things.
And then I just read it and it's all there.
Well, did the AI miss it?
Did the AI understand the linkages between each of those sightings?
If I'm looking at.
For example, I was looking at a company recently And I was looking at it was capitalizing costs okay.
This is a REIT.
And if it capitalizes costs versus putting them through the income statement.
If it goes through the income statement, it makes their operating earnings look poorer lower, and their net EPS ultimately.
But if they put it on the balance sheet, well you know that's an investment in the future and everything looks okay, right.
And so there's a gray area.
Was it an operating expense or was it a capital item?
And so I was, first thing I looked for was capitalized interest.
And so it gave me all the quotes.
And then capitalized costs and gave me all the quotes.
So then you think that that's enough.
But you have to then, and I was showing one of my guys this.
So then let's go to the income.
Let's actually pull up the statements where it told us to go.
Because AI made it faster.
I now no longer needed to flip data the 300 pages but it it gave me where to go.
So now i went there and now i could say well, that means if that is what's happened, then we need to look at this other note to see what you know, the implications of that.
And then we got to look at the cash flow statement to see how it's actually impacting what ends up being reported as cash flow.
And so those linkages come it.
The ai makes me get to the answer perhaps more quickly, But if I don't already know where I want to go, then AI just gives me information.
But that information doesn't help my decision if I didn't start with where I want to get to.
And it sounds like that information doesn't help your decision if you don't know the second third, fourth order consequences.
100%.
I love it.
If that's where investors go and that's where they're going, everything's going to AI.
The bottom level of being an analyst, the junior analyst is going to be replaced by an AI.
The one that said, find me all the references of, you know, where the company capitalized costs.
That the AI can do.
I get it.
But you need someone with experience to know which of those references matter and to what that means to the business.
And this brings about a number of challenges because well, if that junior person doesn't learn, doesn't get on the in on the ground floor, they'll never learn to be able to make all those connections.
And the only way to learn is sort of like being in the weeds and not being in the air.
Yes.
In fact, it ties to so many things.
With my own children, I've seen growing up when we went to school and we were in elementary school.
We would be, you know, we'd have to do the math tables and recite them.
Yeah.
Two times two is four and so on.
I remember I was struggled with my nine times table and then my 12 times table.
And so I had to memorize them and get them going.
But then my children came along and they were using a calculator.
And apparently that was okay.
I went bananas.
I said, you're not going to use the calculator.
You need to learn it without the calculator.
And then you can use the calculator, which is the same with AI.
You need to understand how the financial statements are prepared, understand the linkages, developmental models, so that when the AI gives you information,
You can digest it and make decisions.
Reminds me of this funny story.
When I started university, I ended up in first year calculus.
And for whatever reason, the professor who was supposed to teach that class couldn't teach it.
So the dean of the math department took over.
And on the first class, in the first like minute, he said, there'll be no calculators in this class.
Oh nobody, of course, listened to him, because graphing calculator, you're like oh my God, this makes my life so much easier.
We show up to the final exam, which is, like I think, 80 of your final mark.
Yeah, and on the front page it's no calculators and he did not grade that on a curve and it was not pretty for most students.
I taught at university for about uh 14 years at york and uh, truly one of a very fulfilling time uh in my life and uh, I still love doing guest lectures.
I remember I would always start to you know, I would go over the outline and I would tell the students I said so.
Assignments are due at the beginning of class.
If they're handed in after the 8.30 start time, it's a zero.
It's a zero.
And invariably.
At some, whether it was the first, and usually the first or second assignment, somebody would show up and hand it in late.
And I would say it's a zero.
Yeah.
And they would whine and say, it's how can you do that?
And you're so draconian.
And I said, well, you think in the real world.
When an RFP is required and you've signed with the contract with a client that they demand the report by 9 am on Monday and you show up at 905.
How's that look?
And somehow it's okay.
So it wasn't okay in my class.
And ultimately, I think you build respect because people see that there's a rule and it's followed.
And then people have respect for the rule.
There's this sort of like weird dichotomy, I think, with students right now.
And dichotomy is probably not the right word.
There's this weird path where students are coming out and they're more powerful and capable than ever because they use AI by default.
And so they can get more output than somebody who's maybe been in their career 15, 20 years.
And I use my 14 year old as an example.
You know, in a world where he never had to show up to work, he's a mid-level employee at most companies, based on output.
If you never saw him, he can give you the exact same output than a mid-level employee is going to give you, if everything goes right.
But the minute something goes wrong, He doesn't quite understand all the nuances and all the and AI.
I guess the race for him is like well AI, catch up quicker.
You know, because he uses AI by default.
And I sort of think about this as like making a recipe, right?
Like if I pull out a cookbook and I make a recipe and I do everything perfectly, you wouldn't be able to tell the difference between me and the chef.
Like the food, maybe it's not plated as well, but it's going to taste great.
It's going to taste the same.
You'd be like, this is amazing.
But if something goes wrong, if the oven's too hot, if I don't stir enough, I don't put enough salt in, I don't know why it didn't go right.
But the minute a chef the chef who created that recipe, who's got all the experience, who did the you know, who's made it hundreds of times they taste it and they're like oh, your oven said 375, but it's actually 350.
You stirred this too much.
You let this boil.
They instantly know what went wrong.
Yeah.
Yes.
Correct.
Correct.
Experience teaches you judgment.
And you talk about this in your book.
It's all about the mental models.
I believe that strongly.
The experience teaches you what the numbers mean as we've spoken about.
And when you have experience, you say, I've seen that before.
And a lot of the things I see happening today are link back to things I've seen when I started my career over the last 30 years.
And I think that's something that the AI can't quite do unless you tell it where to look, because it doesn't know the link that I'm thinking about.
But if I can make the initial stage, it can help me get there quicker and more accurately.
And But if I don't, if I don't already have a model of what I'm looking for, it's not going to get there.
So you use the word trust.
And I'm wondering, is there a nuance with likability?
Because I had heard before and I don't know where I got this from, but I remember reading something about like we're more convinced by people we like and use the word trust.
And I'm wondering if that was conscious.
We're more convinced by people we like and we like people that we trust.
So they are related.
It is possible to believe someone you don't like.
Picture someone that you really dislike and they say they're going to do something, but you immediately believe that they're going to do it.
So let's say that there's some foreign adversary who makes a threat and you believe that they'll follow through on their threat, because they usually do, even if you don't like them.
That is possible.
But there definitely is a link between if you like someone, you're more likely to believe them.
And if you believe someone, you're more likely to like them.
And I think that liking is actually really underrated.
So have you heard of the affect heuristic?
No.
We have different decision-making heuristics.
We have mental shortcuts because we don't have all the time in the world.
This is like an evolutionary thing that everybody has this.
We don't train it.
It just comes with us out of the box.
We don't have all the time in the world to take in every single piece of information and make a decision all the time.
Sometimes it's like if you see smoke, you just got to go.
Right.
And so we make we take mental shortcuts all the time.
And one of the big mental shortcuts is if we like something and feel comfortable with something.
It's more likely to be real.
Someone we like is more likely to be competent.
Someone we like is more likely to be smart.
All these things just kind of go together.
And so liking is at the center of that.
You mentioned that we can engineer trust.
How do we do that?
One is repeated exposure.
So in order to trust somebody, first you have to have a sense of who they are.
You wouldn't trust a stranger.
You wouldn't trust a mystery man.
So one is you have to know who are they?
They have to show up enough for you to get a sense of you actually know them and they're not a total stranger to you.
It's hard to trust a stranger, but it's easy to trust even a stranger that you have a parasocial relationship with, because they're not a stranger.
There are people that you've never met in your life who would trust you because to them you're not a stranger.
So first is just become not a stranger.
Second is establish a set of shared values.
I wouldn't necessarily trust your opinion on a restaurant unless I knew that you and I like the same type of food.
So if you are like a vegan that hates spicy food and whatever, I probably wouldn't take your restaurant recommendation, even if I like you as a person.
So you have to establish some shared baseline of values.
Here are some core things that I believe about the world.
And if you share them, then listen to what I have to say next.
If you don't share them, that's okay.
Right.
Not everybody has to show them.
So they have to get a sense of who you are and you're not a stranger.
And they have to get a sense of how you think and how you view things, such that when you say the things they already have ingrained in their mind that they think like you think.
And therefore, if you believe this thing, they're more likely to believe that thing, too.
This is how to resolve a debate or an argument, by the way.
The better way to argue and you see really smooth people like Gavin Newsom does this on his podcast, maybe a little bit too slick, but he's clearly very good at it is he'll have somebody who totally disagree with him on a bunch of things.
And he'll always make sure to start with agreeing with them on something.
Even if it's trivial, I agree with you that that thing was totally insane.
And now we can have a productive conversation, because we've established that it's even possible for you and me to see things the same way, as opposed to your knee-jerk assumption that it wouldn't be possible.
I wonder if that's why sommeliers almost never disagree with you when you are like oh, I taste whatever in this wine.
They're like, possibly, or, you know, in their head, they're like, no way.
Like, that's a completely different taste.
But they never actually come out and say no.
They always sort of like bridge a little bit of a gap.
And then they'll like direct you or steer you towards what they want you to notice.
That's interesting.
I'm a teetotaler.
So I'm the person that If I sniff a wine, I'm like, I think it's wine.
But what I have noticed, which is related to this, is do you ever see online when people are insulting someone or dunking on someone, but then that person shows up and says thanks for your feedback.
The original person who was insulting them or dunking on them almost immediately folds like a cheap suit.
Have you seen this?
Yeah.
Almost immediately they fold.
Hey, man, thank you.
No, totally understand.
I would be doing the same thing.
I got you.
Like what?
What just happened?
And it's because, once you're actually confronted by a person instead of just like a concept or some kind of nebulous idea of a person or some representation of a person, like once the person is there talking to you, even if it's online, we behave in a completely different way.
And so one of the things I tell founders to do is just to show up and defend yourself, or defend your people, defend your companies.
Sam Altman is really good at this.
He defends his employees.
And it's very hard, even as much as with any public figure, people like to dunk and hate and insult.
And when he shows up, a lot of the time you see the person immediately fold because they're just like flattered or they don't want to fight with him directly or something.
It's one of the most powerful things is just to put a human in their way.
I have very high cringe pain tolerance, whatever you want to call it.
I have no issue with that whatsoever.
I think that there is this This gets easier also with age, I find.
The older I get, the less I really care about that stuff.
But yeah, I think most people are not willing to look stupid for a period of time.
I think the other thing is that I think about this all from the concept of entrepreneurship.
In my office here in Montreal, the Shopify office, I have the original screen print that Ben Francis used to create Gymshark.
It was a gift.
It's a super meaningful gift that he gave me.
I love it.
I have it hung up in my office.
Part of the reason why it's up there is because I think that it's an amazing gift and Gymshark is this homegrown success story on Shopify.
It exemplifies everything we stand for.
It's incredible.
But the other reason I have it up there is because what most people don't know is that that was not Ben Francis' first company.
Ben Francis actually had a bunch of failed companies before he landed on Gymshark.
And I think about this idea of this cost of failure, not just from an entrepreneurship perspective but in general.
You have to basically figure out, with anything you're doing, what is the cost of failure here?
If the cost of failure is really high, you really have to think about it.
You have to do a little bit of the math of, is the benefit of success worth the cost of failure?
In some ways, it's just not.
For $39 a month, you can build a store.
It's not a pitch for Shopify, but $39, you can build a store.
If it works, blow it up.
If it doesn't work, try something else.
There are still too many people that apprehensive that, that that don't want to put themselves out there because of this fear of failure.
And I've long believed that, you know, getting really, really comfortable with being uncomfortable is magic.
It's totally magic, and I wasn't always good at that.
I don't think you can be born with that.
I think you can learn that.
I think you can learn resilience, but I don't.
I don't know anyone that I admire who's had success and who has not gone through that period of making kind of look, looking kind of dumb.
And if you're watched the first interview you've ever done, Me?
Oh, God.
Yeah.
I wouldn't listen to the first, I think, like 20 or 30 of them.
I wanted to get a catalog and then I wanted to listen to them.
And then I went for like a really long run and I started listening to them and I was like, oh my God.
And it's like, I should have asked this follow up.
Why did I phrase it that way?
And like you, I'm incredibly hard on myself.
Came back, went through every transcript and like i was like i want to get better at this for everybody else.
But yeah, there's no secrets to why you've been so successful in my, in my view.
I've known you now for a number of years.
You, you simply out care other people and i think that out caring thing supersedes iq eq, raw talent.
Double click on that for a second.
I think that I will take someone—it's the reason why I like entrepreneurs so much that I think entrepreneurs the right entrepreneurs, the best entrepreneurs.
They just simply out-care other people.
They are willing to—if you put two people in a room, one person has 50 capacity, another person 100 capacity, but that 100 capacity person is just not caring as much as 50.
I think I can help that 50 person get more skill.
I'm not sure I can change their level of ambition.
I think you can change ambition, but I think, like sheer innate, deep-rooted ambition, which call it care, whatever nomenclature you want to use, I think that is a superpower.
And it's also the reason why, when I meet someone, they say what do you think I should do with my life?
I often ask them, what do you do for fun?
Because often the what you do for fun question ends up turning into I really want to be a fashion designer.
And I'm like, you should go be a fashion designer.
Even if you've never done it, you may not have the raw skills.
You will learn those skills, but you seem to really care about this thing.
You're probably going to be good at it.
Is there a difference between who cares the most and who wants it more?
Or like, how do you see that?
I look at them the same in my view.
Usually high care comes from high intent or high, an elevated level of desire to succeed.
I'm trying to teach my kids that right now.
I spent a lot of.
You know this is kind of weird, but I kind of wish I had kids pre IPO rather than post IPO.
Why?
I think whatever success that I've had and success of of of things I've been involved with, they are more meaningful to me because obviously I know where I come from.
I know how hard it was, but I also see how Lindsay, how my wife, sees my relationship with things that I've done, in particular with Shopify.
Lindsay has great a wonderful emotional connection.
It's Shopify for Lindsay.
Even my wife is not just a company.
She remembers, you know, those early days.
She remembers those like being on top of Tucker's marketplace in the Byward market.
Uh, the office stunk like the buffet restaurant and, and struggling.
This is pre pre series a even.
And, and I, I like that.
I love that.
She knows that she knows how meaningful it is because she's seen the entire journey.
Um, My kids were born in the last eight years or so.
They kind of only know our life being pretty good.
Our lives changed post IPO.
I don't think that's a secret.
Financially my life changed and I don't take it for granted, but I kind of wish they knew what Lindsay and my first apartment looked like to not in Ottawa Canada, and how gross it was.
It wasn't gross because it was dirty.
It was just, it was a nice apartment because we couldn't afford anything else.
And so what I often, what Lindsay often tells me, is just like yeah, the kids didn't see that, but but tell them those stories.
And so I do.
I tell those kids, I tell my daughters the stories of those early days and how scary it was.
And we didn't know if it was going to succeed or not.
And I want them to see that.
I think I don't want them to think any of this came simply because it was fate or just kind of happened.
I mean, luck plays a role here, but this was sheer grit and willpower, and it still is.
Part of the reason why I like starting these small projects like Big Shot or Firebelly is...
I want the kids to see that.
I want the kids to see this thing, that you know that first episode of Big Shot we did was it was Charles Bronfman.
It didn't do very well.
I wasn't very good at it.
I wasn't a good interviewer.
I didn't know what questions to ask.
Dave and I were kind of awkward fumbling along together.
And Bailey, my eldest, has sort of memorized most of that episode.
And now she watches that.
They love watching Big Shot.
They also watched the most recent episode, Bobby Kotick, who built Activision Blizzard.
We put that out last week.
And I love watching her see the difference in style and the articulation.
Because I want her to know that all the things she wants in her life, she can have.
But it won't be easy.
No one's going to give it to her.
And it's going to kind of suck at the beginning.
Whenever you're in that moment, when you're nervous and you really want something.
Obviously, the best performance comes when you have freedom.
But it's easy to get attached to that because you're like thinking, OK, this is really important.
And so we get attached to it and have tension.
So what you can do is ask yourself, what do I want more in this moment?
To be successful right here this one time or to get better at these moments?
In other words, to master my ego, to not be so caught up in what people think.
So what happens to most people is that they come to these points in their lives where they're really uncomfortable.
Maybe they're giving a speech or playing ping pong in front of a bunch of people.
It doesn't matter what it is.
If you're nervous and other people are watching, they come to those moments where they're really uncomfortable and they back away because they're too uncomfortable.
They're too afraid of looking foolish in front of others.
Whereas the most successful people, they're willing to look foolish.
They're willing to make mistakes.
And so I think a lot of people know that, but how do we get there?
And so in that moment, it's realizing that when I'm the most uncomfortable, that's the moment, that's the key for you.
And it's principle number one for inter-excellence.
Everything is here to teach me and help me.
It's all working for my good.
So we're going to go look for those moments when you're most uncomfortable and say and remind yourself this is my teacher.
And inner excellence is about expanding what you believe is possible.
There's three pillars of inner excellence belief, freedom and focus.
To be fully engaged in the moment, have freedom to play like a child and expand what you believe is possible to become, to do things you've never done and become someone you've never been.
And to expand what you believe is possible, kind of that crucial pillar is we need to find those moments where we're uncomfortable and we need to embrace that moment.
And the way we do it, if we understand that the key thing here is not the outcome, But it's my willingness to be in this moment and not back away.
It doesn't matter if you fail horribly.
You do that 10 times and fail horribly 10 times.
Eventually, you're going to get comfortable in those moments and then your skills will be able to match and break through.
But people don't break through because they come to those moments and they shy away.
I mean, this is we've all done it.
I've done it way too many times.
What do you struggle with today in relation to that?
Anything?
Well, it's the same thing everyone struggles with.
When I come to those moments, I'm like, oh, I'm so uncomfortable right now.
And then sometimes I've forgotten.
It's like I had this conversation with my spiritual mentor, Nick Osborne, and he said what God does is is he gives you a jacket that's two sizes too big.
And that's what a loving parent does when you're four or five years old.
You don't buy them a jacket that's perfectly fit because they're going to grow out of it too fast.
So the parent's going to buy them a jacket that's a little bit too big, right?
So they can grow into it.
And he said, that's what God does.
He gives you this jacket that's too big.
And then you put it on, you're like, whoa, this is not good.
This is not right.
This doesn't feel right.
What's happened?
And that's what I felt so much.
It's like, okay, this is not okay.
What's happening?
I don't get it.
This is uncomfortable.
But God did that intensely.
He's doing that intensely because that's where you need to.
Self-reliance is the biggest problem that I face.
And because I've got very little power, I've got very little ability.
I've only seen the world through this little lens that I want to be able to see all of reality.
And so to do that, I need to surrender my little power.
Is part of this reframing failure into there's no such thing as failure?
It's just it's not a verdict.
It's like data.
Yeah.
Redefining success and failure for sure.
Like the Hall of Fame linebacker, Brian Urlacher told me that I asked him what is the difference between you and the best performers that you've ever NFL, that you've ever competed against?
And he said, most NFL players, they make a mistake and they get tentative.
Hmm.
I make a mistake and I don't get tentative.
And so that's that courage.
That's that willingness to fail.
That's that relentlessness that's needed.
So that's what happens.
I mean, it happens with people, too.
Like if you give a talk at work and you know it doesn't go quite right, it's in your head the next time you do it.
So you're less likely to be successful in a way.
But the counterbalance to that would be, OK, well, what do we do?
We do more preparation.
We, You know, we go through our mistake, we reflect on it, we learn from it, and then we sort of like let go of it and move on, so we don't make the same mistake again.
Yeah, so failure, that's all obviously a big part of it.
And you know, there's one of the principles the presupposition is there's no failure, only feedback.
The emotional part is the issue.
If there's no emotional aspect to it, then, you know, what does it matter if you fail?
Thank you.
