BiggerPockets Real Estate Podcast - 495: The Science Behind Taking Risks (and Why They Definitely Pay Off)
Episode Date: August 15, 2021It often seems like the most successful people are the ones who take the most risks. There’s no surprise that at one point, billionaire entrepreneurs were given the choice to either stay where the...y stood or leap for something greater. This is something that today’s guest, Sukhinder Singh Cassidy, understands. She’s helped lead some of the biggest companies around like J Crew, Stitch Fix, TripAdvisor, and Urban Outfitters (just to name a few). The one thing that Sukhinder has found throughout her years in Silicon Valley and through writing her new book, Choose Possibility, is that groundbreaking leaders don’t just take one big risk, they take several small ones. This works for real estate investors too. If you’ve just gotten into real estate investing education, the first step for you isn’t to go out and buy a house, it’s to join a meetup, contact an agent, or even join the BiggerPockets forums. These are what Sukhinder calls the “minimum viable choice”. Don’t worry about doing everything, just do something! Sukhinder gives some great advice on leadership for those in executive business roles, plus how to find talent in this increasingly competitive market. If you’re just starting in your career, take Sukhinder’s advice and do great work for great people, the rest will fall into place. In This Episode We Cover: How Sukhinder’s love of entrepreneurship began “Coconut events” vs. “subway events” (and how you can plan for both) Embracing uncertainty and calculating your risks Starting in Silicon Valley and building a strong reputation Choosing to make the “minimum viable choice” whenever possible How to know whether you’re managing others or having others manage you What leaders and business owners can do to attract the best talent And So Much More! Links from the Show BiggerPockets Forums BiggerPockets Calculators BiggerPockets Youtube Channel OpenDoor Capital Brandon and David’s Books BiggerPockets Podcast 447: Create Your Dream Life in 3-5 Years Using Vivid Visions BiggerPockets Podcast 407: Buying 100+ Houses/Year in 4 Hours/Week Using Teams, Traction, and (Get this…) TikTok Choose Possibility Website Click here to check the full show notes: https://www.biggerpockets.com/show495 Learn more about your ad choices. Visit megaphone.fm/adchoices
Transcript
Discussion (0)
This is the Bigger Pockets podcast show 495.
So my question for everybody listening to this podcast is, okay, now that you've gone through
the pandemic and you may still be going through it, you've realized something about yourself
and your ability to respond, to be flexible, to be resilient, and to take risk when times
are tough.
Imagine what you could do if you took risk proactively towards the thing you want, just not
when you're backed into a corner.
You're listening to Bigger Pockets Radio, simplifying real estate for investors large
and small. If you're here looking to learn about real estate investing, without all the hype,
you're in the right place. Stay tuned and be sure to join the millions of others who have benefited
from biggerpockets.com. Your home for real estate investing online. What's going on, everyone? It's
Brandon Turner, host of the Bigger Pockets podcast here with my co-host. Mr. David, Framework Green.
What's up, man? How you doing? I'm good. I got my condos in Hawaii, finally getting
worked on. So we're upgrading those puppies and I'll have my first Aaron B's up pretty shortly here.
Aaron B's. That's had a new thing. Did I say that?
Short term rentals is what I meant to say. Aaron Bs. All right. Good. Good, good stuff, man. I got a good
contractor. I've been working with the last few weeks who's pretty phenomenal. So I'm going to
share him with you here because I'm just about done with them. So, oh, there's, I don't think there's
a higher compliment in a friendship than sharing a contractor. I agree. I mean, that's like I'd share my
toothbrush before I shared my contract.
All right. Well, man, we're talking today about a lot of good stuff, specifically a real good look at risk, a good look at taking chances about possibility, but kind of a different twist on how we take risks with somebody who has been in the industry for a long time. Not the real estate industry, though, the Silicon Valley industry. We're talking to a power player in Silicon Valley. Her name is Sukinder Singh, Cassidy.
Most recently, she was the president of Stubhub, which is a huge gigantic company.
She's been on the board of a bunch of massive companies that you, I know you've heard of.
For example, J-Crew, Stitch Fix, TripAdvisor, Urban Outfitters.
She worked at Google once.
There's a lot of huge stuff here in her portfolio of businesses she's helped grow.
And she got a new bookout, and you're going to hear more about that as well today.
But we're going to talk a lot about risk.
We're talking about leadership about what makes a successful company grow.
and what makes them struggle.
And yes, that applies if you have no employees or 100 employees.
It's the same concept.
We talk about frameworks a lot and how employees especially and people that you work with contractors.
I mean, like, I had a realization in this interview about working with contractors that I wish I would have had 10 years ago.
It gave me a completely different way of dealing with them.
And that going forward from this moment on, I'm going to have a very different way of dealing with contractors.
I think you're going to love that.
It's going to change your business as well.
So that and more.
Make sure you listen for that.
and yeah, so much good stuff today.
But we're going to talk about how to build your risk muscle.
So that's kind of today's show.
But before we get to the interview, let's get to today's quick tip.
David, what you got for us?
For those that have made it to the top of the mountain, or at least higher up the mountain than you were at one point, remember what it was like when you were at the bottom.
And you were full of vigor and desire to get up there.
And you just didn't know what to do or where to start and throw down a rope.
There's so many people that are just going crazy.
crazy inside trying to figure out what to do. And we know what to do. And it's a little bit of
effort that makes such a big difference in other people's lives. So oftentimes people won't say,
we talk about that in the show, exactly what they're feeling, why they're intimidated,
why they're afraid of risk. But they desperately want to start making some traction. So rather than
always looking up and saying where do I want to go, sometimes it's okay to look down, see people
behind you and give a hand and pull them on it. Powerful stuff, man. Good job. Way to wing that
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All right.
And I think that's pretty much ready to go.
Anything you want to say before we bring in Sukinder?
No, I really like today's interview.
Let's grab her and bring her in now.
All right, here we go.
All right, Sukinder.
Welcome to the Bigger Pockets podcast.
Awesome to have you here.
Thanks, Brandon.
Thanks, thanks, David.
Yeah. So let's dive in. So you have been on, I was reading your bio, you know, a ton of high profile
boards, ran successful companies, started companies. You've been around the whole like Silicon
value world for a long time. So there's about a million questions I could ask in terms of growth and
leadership and all this stuff. But I want to start just by maybe getting a little bit of background on
you. Like how did you like get into this world where you're like this powerhouse in Silicon Valley?
Like how did that happen? Well, it's so funny. You ask that. People always
like, oh, Sukkinder, like, what happened? How'd you end up in Silicon Valley? And, you know,
we all have this image, right, that everybody who's here must be some insider. But I grew up
in a small town in St. Catherine's, Ontario. And both my parents were doctors. But more than being
doctors, my dad loved running a small business. Like when I say he loved being an entrepreneur,
it's like, it was amazing to sort of see him growing up. I only appreciate it now, of course. At the time,
you're like, ah, dad, what are you having me do? But, you know, he had us, believe it or not, like
working on his taxes, like his ledgers by the time I was like seven or eight years old.
like preparing my dad's books at the end of each year to file his taxes was like a family affair.
And so, you know, I grew up with this very close in view of small business and of entrepreneurship and a father who loved it.
And by the way, he didn't just love entrepreneurship and medicine, which was his day job.
He also loved tech infesting.
Like, who knew?
Like, I remember when my dad and my dad was older, right?
So he was in his, he was in his, probably in his 60s or 70s.
And I remember calling him up as his broker because you remember, like it used to be that you read stock stock prices in the newspaper.
You'd have this magnifying glass because he couldn't read the numbers.
They were so small.
And he'd calls broke and you'd be like, Tom, let's buy some AOL.
I mean, I didn't even know what AOL was, but he was my 60 to 7 year old dad.
He's probably 67, 68 at the time, buying tech stocks in like 1990 something.
So people always give me credit for being in the valley.
But I give credit to my dad because I feel like I went off to undergrad business school.
I thought I wanted to be a big corporate executive.
I ended up investment banking.
By the time I was in my mid-20 and I was like, you know,
I really want to be an entrepreneur.
Like my dad told me to work for myself.
And so if I did one thing right, it's probably that in my mid-20s, I quit my job and moved to Silicon Valley because I didn't know how to be an entrepreneur.
But I figured there were lots of smart people to learn from.
And turns out that was a pretty good time to quit and move somewhere.
Yeah.
So what did you start?
What was your very first business then?
Well, interestingly, my very first business was a failed business.
When I was sitting in London before I moved to Silicon Valley, I thought I would create,
cufflings for women. I know, don't laugh, but I was like, I was like, you know what?
Like, I'm wearing all these suits and everything that's available is for the guys because I was
on a Wall Street banker. And so I made a prototype and then I proceeded to do nothing with it.
I didn't know how to market it. I didn't know how to set up a website. So fast forward. So that was a
failed attempt. I carried those bag of coupling prototypes with you go from house to house,
like literally through my 40s, just as a reminder. And then when I moved to Silicon Valley,
I ended up at a startup that sold to Amazon. But,
I was at Amazon in my late 20s after the startup I was at sold to them. And many of the investors
in a new company called Jungley where the angel investors were the original founders of the company
I was at. So they sold to Amazon, had a successful exit, became investors. And they introduced me
to five engineers who were looking for a business co-founder. And my first company was Yodali.
And for those of you who don't know what Yodali is, it was the very first platform for aggregating
all your financial data.
And it went 15 years before it went public and then was subsequently bought.
So that was my first company in the Valley and all came through connections through the people I'd worked for.
Can I ask you a random question about Silicon Valley?
Sure, please.
Do you know what the first company was that added LY to the end of their name and started the trend of tech companies that were something Lee, Yodley, Trendley?
Was it musically?
Oh, wait, you're thinking LY. Yotley was L-E, my friend.
So before they were the L-Y's, they were the L-E-E.
So keep in mind, I was it jungly.
I was at Yodley.
Yeah.
Yeah.
I am the original hipster.
Like there was a Lee,
L-A-E before an L-Y.
I'm wondering if you started that whole trend.
Do we have the-
It could be.
Oh, my God.
It might have been us.
I will just say like there's a whole set of companies started by Indian co-founders.
Like I said,
the company I worked that was called jungley and then my company was totally.
I mean, yeah, I think we did.
Do we get some credit, right?
You should.
I mean, that makes you like a legend.
You're like the first person to put cleats on a football field.
Look how much easier it is to run.
For those that don't know in the Bay Area, there's a trend for tech companies.
They always do like something with their names.
And right now it's to add Y to the end of a normal word.
That's true.
Like whatever you're selling, right?
Bigger pockets.
Yeah, we should.
Yeah.
Yeah.
For whatever it's worth, I own a couple of domains that end with an L.Y.
I don't know what to do with them yet, but I did buy a couple myself.
Oh, I think if you got in on that real estate early, you just picked every
words you could and add an L-Wi in domain, you probably made it killing.
I love it.
All right.
All right.
So, okay, so you, then you served on a lot of boards.
You did a lot of that stuff.
And now, you know, here we are in 2021 recording this.
And we just came through a hell of a year to put it lightly, right?
Like a lot of things changed during this year.
And a lot of people, I mean, some people lost jobs.
Some people realized maybe for the first time ever that their job wasn't so secure.
So the first question I have on this is how did risk, like you talk a lot of risk and you got a new book coming out that's largely talking about risk. So what did the pandemic do to our collective mindset when it comes to risk and comes to security?
Well, I think you're hitting the whole reason I'm here and I'm excited to chat with you guys. You're right. I do have a book coming out about how to take risk and how to take risk like systematically, right? How to kind of buck this idea that it's a one-off event that if you're,
If you're lucky once, you'll succeed and embrace risk taking as a habit.
So how does the pandemic fit in?
Well, it's pretty interesting.
I feel like in our daily lives, many of us hesitate to take risks, right?
We worry about what will go wrong.
We fear failure.
We worry that somebody will laugh at us.
We'll worry that we'll lose money.
We'll worry that we'll be unhappy.
I could list like the three or four fears most people have when they try and make a
decision and take a risk.
And then all of a sudden the pandemic comes along.
And the pandemic is what I called a coconut event.
Okay, so a coconut event, according to researchers, is an event that happens that you simply can't predict.
So there are events that can happen with some volatility that you can predict.
There are things called subway events.
Like, you can predict that subway's going to come and it's going to be either a couple minutes earlier,
a couple minutes late.
So you can predict the range of volatility on a subway, right?
And so you can plan for it.
But what happens when a coconut happens?
A coconut is like literally a coconut dropping out of a tree, hitting you on the head and you dying.
That's like, that is the definition of a coconut event.
So we all just had a coconut event.
And it turns out the coconut events teach us a lot about our ability to take risk and to be resilient and take risk in the face of harm.
Right.
So we always are like, oh, my goodness, why is it so hard for people to take risk when things are good?
Yet when things are bad, we find out really how agile we are and how responsive we are.
So I think that's just what happened to all of us.
Now, I'm not saying that the pandemic has been easy.
In fact, it's been very difficult.
But as you know, people all adapted and responded in ways they didn't think they were capable of and they did it on a dime.
So my question for everybody listening to this podcast is, okay, now that you've gone through the pandemic and you may still be going through it, you've realized something about yourself and your ability to respond, to be flexible, to be resilient, and to take risk when times are tough.
Imagine what you could do if you took risk proactively towards the thing you want, just not when you're backed into a corner.
So I think the pandemic taught us all about our ability to take risk.
And it also taught us that even if you don't want to take risk, risk still happens to you.
So isn't it better to kind of embrace it proactively and take advantage of it to its fullest?
In your research, have you found that risk takers are generally just more, like, is that a sign of success?
Like the more risk taking, the more risky you are, maybe that's the word, adding a why to it, right?
The more risky you are, the more successful you become. Do they correlate?
They do, but they don't correlate in ways people might expect.
I think that we look at the world's biggest risk takers. Let's look at our friend Richard Branson, who just went in.
do space, right? Pretty amazing. I'm sure you guys agree, right? Or you look at Elon Musk,
or you look at, you know, Jeff Bezos. And we often think, oh, my goodness, risk taking is for
the riskiest among us. Does that make sense? But what we fail to consider is that that's not
Richard Branson's first risk. It's not his second risk. It's not his 100th risk. It's probably
his 10,000th risk, right? Jeff Bezos, do you know how many attempts he took at Amazon Marketplace?
I know. I was like the first company he bought to attempt Amazon Marketplace. 1997. No,
1999, Jeff Bezos, 1998, sorry, Jeff Bezos bought our company, jungly.
How long did it take for a marketplace to become successful?
Jeff Bezos killed multiple versions of marketplace before it ultimately happened.
So we tend to think that, you know, the most successful people in the world are risk takers.
That's true.
But they're not the kind of risk taker you imagine from the outside end, like one mighty choice that worked out.
I'm like, they are risk takers because they built risk muscles.
Does that make sense?
And so I think that that's the opportunity for all of us.
It's not to think of risk as this mythical hero's journey where it's like one great choice that
somebody made.
And you look at that person, you go, oh, my God.
Rather, it's that they've been practicing risk-taking with all less failures and successes,
big and small for a long freaking time.
Well, what about the way we define risk?
I think when most people hear the word risk, it is automatically associated with bad.
We see that a lot in our world of real estate.
When people hear He-Lock or Home Equity line of credit, they immediately say, oh, that's bad.
or subprime loan equals morally evil because they were used unwisely for a time.
Can you speak a little bit about maybe some of the misconceptions of risk that the uninitiated
have versus those that have a bigger risk muscle?
Yeah, sure.
Absolutely.
You're hitting it.
So interestingly, if you looked at the dictionary, Miriam Webster's definition of risk is,
I think it's danger or harm, the threat of danger or harm.
Okay.
So if you heard that word, who would want to take it?
That if you look at the definition of risk taking, it says something more along the
lines of, you know, embracing uncertainty on the way to achieving a goal. Okay, that's a more balanced
way to think about risk taking. The reality is most of us think about taking risk. And by the way,
when I say risk, it could mean a micro risk. You speak up in a meeting. It could be a medium-sized
risk. Like, you know, you decide you're going to start a side hustle. It could be a gigantic risk.
Like, you quit your job with nothing to go to, right? All three of those things are risks.
But I think we tend to conceive of risk on the harm side of the equation. And I think that's one of the
biggest misconceptions that risk equates with harm when most of the risks we have an
opportunity to take are for upside. Yet we don't really talk about risk that way. But that's why
the book is called Choose Possibility. It's trying to reframe risk for what it really is.
Like every time we take a risk, we're kind of choosing a possibility, right? It may or may not work out,
but we are actively choosing a possibility and we're pursuing that possibility with every choice.
And so I think that's one of the biggest misconceptions. The other is the one I talked about,
this idea of the hero's journey. I call that the myth of the single choice. Like one big choice
stands between me and success. You know, and I'm like, I don't know. I'm sure you guys know a lot
from your real estate theory that real estate's about building portfolios, right? It's about taking
multiple risks. It's not about the single like home run or Grand Slam. Yes, you might choose to
take one bigger risk in your life. My father is an example. As a doctor, he bought a building, you know,
in order to start a walk-in clinic. But like, that was a big risk where his little risk was like maybe
renting it out to, you know, five other doctors.
Like, real estate goes by the same principle.
You have to think in terms of portfolios and taking multiple and parallel risks,
not a single choice on which you put everything.
I love that you're saying this.
Yeah, I teach this concept a lot on these.
I do these live webinars every week and I teach people kind of how to get started.
And I always say that wealth is not built through a property.
It's built through a portfolio.
In other words, people are like freaking out about that first deal.
They got, it's got to be a home run.
It's got to be the best deal ever, like the kind that we brag about on the show.
occasion, like, oh, I just bought this amazing, like the most important thing that you can do,
and I think I'm going to start rephrasing it the way that you call it the wrist muscle. The most
important thing you can do is get started because, like, even with a mediocre deal, even with a
break-even deal, because like it builds that risk muscle. It builds that like momentum, right?
It builds momentum. It builds learning. You have a feedback loop, right? You can plan for your next
deal better. Like all this abstract planning from afar and then never taking a single risk,
it's like, it's crazy to me. But I think that people,
don't think about risk as portfolios. And it's weird because financial trading teaches us to do that.
You know, real estate investing teaches us to do that. By the way, even tech companies take multiple
risks, right? Like they take risks upon risk upon risk, many little in order to pivot. So by the time
they've pivoted, you know, 180 degrees, it's actually the results of probably 50 different choices,
not a single large, gigantic step into the unknown. Yeah, when it comes to our careers and ourselves,
we really don't embrace calculated risk taking. And I think that's the,
opportunity. What do you think about this concept that, at least from my perspective, when you first
start a new endeavor, you're first working a new muscle, you're learning to ride a bike, you're learning
to snowboard, you got a new job. The risk is always highest in the beginning, right? For a startup
company, the risk is always biggest in the front part of that journey. And then as you figure
it out, the risk starts to decrease. So many people try something once or twice, they fall off the
bike and they go, oh, this wasn't for me. Do you see that happen a lot too? I do. And the irony is,
I think most people presume, so I think there are two things.
Psychologically, the first risk is the hardest.
Does that make sense?
Psychologically.
Because by the time you've made one choice and see how it works out, the next choice is
easier and the choice after that.
Because you know that in a minimum, you know how to respond, right?
You learn how to respond.
So like psychologically, the first choice is the scariest.
Ironically, the best way to get into action is to think about the smallest micro-risk
you can take.
Because I think the minute you make it a big one, it's kind of a doozy and you might
never get started.
And that's why it's so scary because we put everything on.
the first choice. And ironically, I feel like all the power isn't continuing to choose. I always say
to people like, I'd rather choose imperfectly 15 times to get to an outcome than choose once perfectly.
I don't know. What do you want to do? But everybody's so busy thinking that they have to choose
once perfectly. And to your point, so I think psychologically, it's the hardest to take the
first risk. Ironically, you could start with the smallest smid of a movement and get into motion.
What's an example of that, like a smaller kind of micro choice? Sure, like anything.
Like we were chatting about let's say, let's say you think you want to, you know, go join a startup and you just don't know what it's like.
The microchoices, you don't have to take the first recruiter call that comes your way.
The microch choices, you could go do five informational interviews with like five people who are in startups.
The microch choices, you could go figure out if there's a new emerging division at your company.
The microch choices, you could start a side hustle.
The microch choices you could go take, you know, classes or join an incubator and pair up with somebody at night.
Like, those are all micro choices before you have to actually quit your job and take the first thing that comes your way.
You know, so I always think that microchoices are the smallest choice you can make that gets you information and learning and some sense of what it will be like.
Is that the same thing as you've mentioned earlier, minimal viable choice? Is that what that is?
The MVC. Yeah, I would say that I would, I would say when we're contemplating bigger choices, I have this like thesis in my head, which I'm happy to share if it's useful of like the things you should be evaluating on bigger choices.
But I always say at the end, like, suppose you've evaluated.
you know, some bigger leap you're thinking about making a job change, whatever. And you've gotten it all down on paper. You've done the pros and the cons. You've talked to your like, your, you know, your personal kitchen cabinet, all that stuff. You still can't choose. What I would say is like, make the minimum viable choice. What's the smallest piece of the choice you can make to get into motion? Because that's all that matters. Like, you know, that's all that matters. Whether you make the choice in one big swoop or whether you make like 10, you know, 100 little choices to get you along the way, the MVC. I'm just like, just pick the MVC. What's the MVC? So you
You did something after you did all that evaluation.
You know, if you can't bear to do the big choice, do the small choice.
Any choice is a good choice to get you started.
I like that a lot.
When I think of like putting this in an example of like getting started with a real estate investment
portfolio, for example, like you, you don't have to commit to buying a property and
committing hundreds of thousands of dollars right away, right?
Like that's the scary.
That's the big picture.
Right.
The beginning is like you could spend an afternoon going to an open house.
Like that's a super low, easy.
like things you do. You can go and analyze. Yeah, that's it. Just go to an open house. Go talk with one real estate
agent. Costs no money whatsoever. Gets you out of that comfort zone. Like analyze some properties.
Like run the numbers. Just see what you think. Right. And don't you find it interesting? And I know we keep
harping on this. I'm happy to move on. I was feel like people look at big binary choices. And then they're
frozen and afraid to move. And I'm like, well, if you're afraid to make the big binary choice,
make the smallest commitment you can and like get information, you know, get going, discover,
pipeline, you know, learn. These are all great ways.
to spend your time in Iowa. I'm like, if you can't
risk a little bit of time, what makes you think you can risk your whole career?
Yeah.
If you can't risk a little bit of time to go to an open house?
Yeah, exactly.
What makes you think it's right? They'll make buy building yet.
Exactly. I use the analogy often of like if you, like I used to live in the Pacific Northwest and
you know, you're still kind of value. You're familiar with this. Well, it's foggy sometimes, right?
So you're driving in the early morning. It's foggy. You can't see two miles down the road.
And so like the sphere built up. Like, oh, what if there's a,
an accident. What if there was a deer in the road? What if there's an animal? What if I can't,
like, but it would be ridiculous to pull over to the side of the road just because you can't see
two miles down the road. So instead, what do we do? We just drive a little slower, right? Take it easy.
Go like east off the gas, turn your high beams off. Yeah. Well, it's so funny. I heard an analogy
once from somebody in Silicon Valley that I quote in the book because I love it. It's like,
you know, making a move is like being on the monkey bars. We always think we need to see to the end of that course,
but you don't, right? You just need to reach for the next round. And if you reach to the next round. Who has a better
It's wrong. Right? Yeah, it's a good one, right? I like the monkey bars analogy. I can't take credit for it, but I like it.
I really like that a lot. Yeah. And so much, it's so much easier than you like, you take a lot of pressure off yourself. I mean, like, you don't have to think, how am I going to make $10,000 a month from my, from my business? So I can quit my job. Like, that's a scary big picture of things. So stop worrying about it.
Absolutely. And look, I mean, all of these strategies are just to get you in motion, right? I think it's also interesting for us to talk about if you want. How do you get smart?
about the risks you take. Like, you know, first and foremost, you get to get an emotion. And a lot of that is, like, debunking this idea that there's a single choice. If you, the minute you know you can keep choosing, like, the minute you know that, right, it takes the pressure off the first choice. It makes it easier to make the first choice because you're like, wait, after the first choice, there's a second and a third and a fourth, then a fifth, then a tenth. Like, it's not done in one. But I think the second thing that people often kind of, you think about other myths about risk taking. The other myths are really about like, like, how do you become a calculated risk taker? And how do you
get smart about the risks you take. And I think that's also another place where people are like a
hope and a prayer. They tend to sort of overweight that everything is their own execution. Like I need to
be a perfect executor. This is why you see these. I've been a CEO before. So I see all these perfect
plans. Like you try and plan for a quarter. Every team brings you the perfect plan. All the things that
will go right. And I'm like, okay, that's interesting. But like maybe the more strategic, you know,
risk taking approach is to plan for what can go wrong. And David, you talked about this earlier.
Like, you know, this links very much to fears of failure.
Like, it's not just like helping people see that they can take little risks.
I think often being a smart risk taker is helping people conquer their fear of failure.
And think about, you know, all of the choices they might make if something goes wrong and maybe even plan asymmetrically for the downside.
Like, if you actually planned more for the things that could go wrong, then could go right, you're likely to weirdly conquer your fear of failure and be able to go pursue a choice rather than, you know, just hoping everything's going to go right, visualizing only success.
So I think there are these other tactics that can help people get smarter about the risk they're going to take.
It actually get them in emotion too.
I love what you're saying because you're highlighting how emotional this decision really is.
But we tend to operate in our neocortex where we think it's all just whatever is on paper.
But like the concept of momentum is it's all in your head.
What's a good way to describe it?
When you consider going to like a workout class and you see CrossFit people, you're like, I could never.
do what they're doing. Working out is not for me. Well, the reality is they all felt that way first.
Maybe where you need to start off this is just going for a swim in the morning or going for a walk.
And then that wasn't so bad. And then you take a light jog and you're like, actually, I kind of liked
how I felt. I want to take another one. And like those progressive steps get to the point where I'm
going to go to CrossFit, but I'm going to have very low expectations. I don't care if I just work out
with the bar, not even a weight on it. I just want to get through a workout. That's my goal.
And then you get through it and you go, okay, that was a bigger deal than I thought.
Next time I'm going to push it a little bit harder.
So much of business works just like that.
I would bet you, So Kinder, if we went back in your life 10, 15 years and they said,
here's where you're going to end up.
You would have had zero idea that this is where you would have ended up, just doing your best
every day and going to work.
And maybe you would have even said, yeah, I don't want that.
That's not who the version of me right now would want to be doing.
It's almost good sometimes, I guess, that we don't see what's at the end of the monkey bars.
Because the person that we're going to be when we get to the end isn't the person we are right now.
And so we can't know how it's going to feel when we get there.
Yeah, I think that's true.
By the way, I mean, make no mistake.
I always have a plan.
So, you know, I call it my whiteboard plan, which is I kind of roughly knew I always wanted to be a CEO, right?
And I roughly knew I'd want to do sort of be a CEO of a consumer company.
But I didn't know how, to your point precisely, right?
And getting into motion gave me the confidence that, you know, A, I could make things happen.
And, B, I could respond to the things happening around me, which is,
as important when you're a risk taker, right? It's like to acknowledge you don't always have
control of the situation. So you don't know quite how you're going to get there because
unfortunately, 100% of, you know, our success is not just about our execution. It's about the
macro environment we're in. The headwinds, tailwinds, in the world of real estate, it's like, you know,
what are the macro conditions, what regions are booming and what regions are flailing? Like,
there's a bunch going on around you that you have to respond to. But I think to your point,
once you learn that you can respond, you know, and be agile, you sort of gain confidence that
you'll figure it out and you'll hit that macro goal. You just don't know.
precisely how, right, but you're more comfortable with things unfolding as opposed to saying,
if it doesn't unfold the exact way I predicted, I'm screwed. So you're right. I, you know,
I always had an intention to be a CEO and I became one. I just couldn't have told you how.
And the irony is 20 years later, I say to people like, my career looks pretty cyclical.
People think of it as linear because they only want to manage that like, they only see the peaks
of my career. They're like, oh, so, Kinder, you did this. And then you did this. And then you did
this. I'm like, yeah, but if I showed you the cycles underneath that, you'd see a different
kind of repeating pattern, which is, you know, the rewards that I imagined were, to your point,
they didn't unfold exactly as I imagined. Sometimes I ended up with an entirely different reward
in an entirely different place for a risk I took. But over the course of time, if you just repeat
the cycles, yes, I have had compounding benefit. And I roughly got where I wanted to go.
Just not exactly the way I imagined. So it's about playing out the cycles. So what about somebody
who wants to get into, say, my analogy of the CrossFit gym, but they don't see anyone there
that looks like them that comes from their background. They don't have a way to connect with any of the
people that are like, these are a bunch of grunting, sweating people and they don't have a
background and that type of thing. But they still know this is important. Do you have any advice for both
what the gym can do to make that a more appealing environment to different people as well as what
people can do to get themselves kind of acclimated? Yeah, well, you're hitting on, I think,
a topic that's near and dear to my heart, which is, is it safe for everyone to take risk?
And for those of us who have to create environments in which people take risk, what do you do?
And then to your point, like, what's the accountability on the person involved, right?
And so let's start with the easier side of that, which we've just been chatting about.
If you're the person involved, I always say, like, one of the ways to be a smart risk taker is to put yourself in environments where you find people who share your values,
because that's one of the things that makes it easier to take risk, right?
Like we all, I think you know this.
The research all suggests it will all do better if we're in environments with diverse
thinking.
That's great.
But you know what's underneath diverse thinking is shared values, right?
Like you can only really put yourself at risk when you trust that the people around
you, you know, are similarly, I don't want to say similarly minded because that sort of like
that means homogeneous thinking.
I just mean like have similar values, you know, that at the end of the day, their sense
of worldview is similar.
Like as I talk about, values is like what you think is just and fair.
So when you're in environments where you can find people with common values, you can do your best work to your point.
You can take more risks. You can say something in a meeting and not worry that you're going to get shamed, right?
Like you can do all the things that are not. You can go to that CrossFit gym, right? And if that CrossFit gym, you know, this is the word of the day. You guys know this feels inclusive, meaning it feels like you have a tribe of people who you can imagine share your values. That could be because, you know, the person at the front, you know, at the front door of the gym at the countertop, even if they look beautiful.
like, you know, is welcoming and friendly and shares a story about something from their personal life that makes you feel like they're not perfect. And then you're like, oh, I can enter this gym. I don't quite feel like an ass, right? And I can go try it out to make the analogy sound. So I think that our job is to look for environments where we find people who, where we think we have values fit. And then to your point, it's to take those little risks. It's to, you know, manage your own fear of failure by like thinking about what's the worst thing that could happen. If I act, I always say that like that. So that's in our realm of what's possible.
I think if you're a leader who's managing environments, you know, and you're thinking about how to make it safe for everyone to take risk, I think, A, there has to be equal access to opportunity.
Like, you know, you think about a company where you're like, well, I want somebody to take a risk.
Well, what they need to see is that everywhere around them, they see demonstration that, like, people who look differently can succeed, that there are multiple paths to the top.
Does that make sense if everybody looks the same?
And everybody who's successful looks the same.
And, you know, the CEO or the leader in question, like, treats only certain people well and not others, or, you know, always uses one person to demonstrate the exercise who's like, absolutely, you know, impeccable.
Like, these are all things that, you know, may make people feel like it's not possible for them.
And we have to realize when people perceive that it's not possible for them, they may take less risk, even though we want them to take more.
So I think as leaders are opportunities, whenever environments we create, we have to expand access to what's possible and show multiple.
types of success, you know, celebrate multiple types of risk taking, celebrate different types of
risk takers. When the introverted person in the room speaks, like celebrate it. You know, when somebody
who never says something in a room, you know, says something smart, say, oh, like, reinforce it
five times over and be like, oh, like Brendan said in that other meeting, they give credit.
Like, these are all things you can do to make it possible for people to feel like they can
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Well, let's talk about one specific group that applies to us as real estate investors.
I'm curious your thoughts on it, and that is women real estate investors.
I mean, 80% probably, give or take, of our listeners are male, and it's a very male-dominated industry.
Is that, like, I don't want to sweep broad generalizations, but is that because women tend to be
less risk-takers?
And that's why they don't necessarily come into real estate as a field more?
Or are there things that we can do to try to foster more women in this industry?
Yeah, I think, well, I think that there are a couple of things to unpack there.
First of all, there is a lot of third-party research.
Like, remember, I am not a statistician.
I'm an operator who wrote a book.
But, you know, there is a lot of research that talks about the fact that men and women do perceive risk differently.
By the way, that doesn't mean that women lack ambition.
It just means they have different perceptions of risk taking.
I will say we put out a very simple quiz with like four different risk archetypes on the book site.
You know, it's at choosepossibility.com.
You can take a risk quiz that's sort of, you know, less than 60 seconds to take.
But interestingly, when we put our risk quiz out to a sample of the U.S. population, we also found
differences between how men and women generally perceive or categorize themselves as risk takers.
And we have four risk-taking types on the site.
One is called a calculator.
You can probably imagine what that is.
Pros, cons, but can make decisions.
The contemplator, which is the most popular style in the United States.
60% of the people we surveyed are contemplators, which means pros, cons, but can sometimes be
stuck in indecision and have regrets for choices they didn't make.
Then on either side of that, to the extreme of the calculators, the change seeker,
somebody who's like moving all the time, almost like so often you're like, wait, can you just sit still for a moment?
They have more of a threat of acting rashly, but they probably never miss an opportunity, right?
They also might be the overcommitter.
And then on the other side, the extreme opposite of the change seeker is what we call the critic,
who more naturally sees the danger in any situation.
It's far easier for them to identify the danger than the upside of a situation.
So when we put that survey out, women and men generally index similarly, but women were more likely to be contemplators and more likely to be critics.
So I do think there are differences in how people take risk.
And so could that explain why women are less entrepreneurial in some fields, including real estate, potentially, right?
But it also, to your point, invokes, well, what do you need to do to make it, you know, make it comfortable for different types of people to take risk?
and, you know, I don't know, and I know it's hard to be the poster child in any situation
when you're the one. But the reality is when you have successful female real estate investors,
what can you do to signal that you are open to attracting more? How do you highlight and celebrate
those successes? You know, how do you acknowledge what those folks needed to do differently?
So I think that there are some explanations for why different fields, including real estate,
you know, have different profiles on men and women. And I think risk taking is certainly plays into it.
the other thing that plays into it is, you know, how to make it possible for all people in any given field to participate. And I don't know, you guys tell me, I would think that in some ways real estate is actually good for women and that it has some flexibility and we're setting your own hours if you want to be, let's call it a, you know, a caregiver. But on the other hand, it's a hundred percent commission based often, right? Like you eat what you kill if you're an agent. I could be wrong, but you guys know better. And I think if you're a real estate investor, you have to take some portion of your savings, right, and put it.
in an asset that might be locked up for a period of time. So these are all things that might give,
you know, people who are more contemplators pause, right? And so maybe what you need to do is even
identify how, you know, how different people can be successful and what micro-choices are available.
Like, is there a way for someone to get started in, you know, investing in real estate through a fund
or through a group of angels? Like, you know, these are all ways you can sort of demonstrate that it's
possible to get started in smaller in smaller waves. I have a I have a real estate fund.
You know, we raised, I don't know, $75 million or something like that in the last year to buy a
bunch of things. Yeah, it's cool. But I would say, I don't know if that's a majority,
but I'd say it's probably pretty close to majority of people have said the reason they're
investing with us is because they want to eventually do it on their own, but this is a low risk way
to get in. To get in, right. To take him. So I just kind of connected that full circle to what we
talked about earlier is it's a good way that like, and a lot of,
of our investors are women. A lot of them are women.
Or, like, led, you know, they're married couples, but the woman's the one that we talk with.
We reach out. We have a conversation with. Yeah. They're leading that. Yeah. Absolutely. But,
but, you know, maybe what, you know, and again, I'm not here to theorize on your business. But, you know, I think what you can do to invite in, you know, groups that are underrepresented and to make room for them, I will just acknowledge that sometimes that takes additional effort, right? Like, it's the same thing with, like, boards. You guys know that I have a platform called the board list that tries to create representation in the board.
room. And there's no doubt. Like I hear from many people like, you know, I go after women and they say
no at a disproportionate rate. They literally say no. I get all the way to the offer and they say no.
I said, yeah, I understand that. So all I can tell you is you unfortunately have to go at it,
you know, multiple more times. Like you might have to fill your pipeline 80% with women to get a 50%
take rate from women because they may say no at a disproportionate rate. Anyway, it's not a single
fasted problem. Yeah, we get that same issue on the podcast itself. You know, like,
We try to get as many women as we can, but I would say we get rejected nine times out of 10 if I ask a woman to be on the show.
My own wife has not been on the show.
She won't do it.
She's too, like, she wants to be behind the scenes where I tend to like put this on like most guys like myself.
Like I mean guys that I know.
We like to be out in front and center.
I like being the guy in the podcast.
And so it's just a it's a difference.
But it goes to like it doesn't mean I just accept the fact, oh, well, you know, most of the people apply in our men.
It's like, well, how do we encourage more women to?
how do we make them feel more comfortable to apply?
How do we reach women where they're at?
And I found this with people of color as well.
I mean, most people that apply for my job positions,
they look and sound just like me.
And so the question,
I had a good buddy the other day called me out and he said,
well,
what are you doing to reach out to other groups of people
that aren't looking and sounding like you?
Because those people are already in your world.
So how are you going into another world to attract more people and more applicants
and more people?
And it's like, I'm not really.
I'm just relying on my own audience, which is just like the self-fulfilling kind of, you know, cycle.
Prophecy. We all live in that. Yeah, we, you absolutely do. If you want to extend possibility,
you have to expand possibility, right? You have to just, and that, and I understand that that takes work.
It also has great rewards, you know, and in terms of better performance, right? We know that, but,
but I totally get it. And so, yeah, maybe coming all the way back, I think one of the fun things for your audience to do,
whether you're a man or a woman, person of color, you know, of, you know, of kind of the majority,
origin, it doesn't matter, but you know, go take the risk quiz and learn a little bit about your
own style because I think, I will say that like, you don't need to sit. I always think that people
think they need to be this ultimate optimist to be risk takers or to be risk takers or risky to,
naturally risky to be risk takers. I'm like, nothing could be further from the truth. You just know
need to know what you are and deliberately make choices, right, that put you on the path to building
the muscle. And, you know, and then I think optimism is the output, to be honest, becoming a risk
takers and output of the practice, not an input. Oh, that's really good. I like that. Well,
before we let you go, I do want a couple, a couple more things. It would be, it would be sad not to
pick the brain of somebody who's been in Silicon Valley and helped numerous companies grow and
succeed and sell and all these cool things. So I just got a few questions I want to just throw
at you related to just growth in general. First one, you know, looking at teams and specifically
like leaders of teams, like whether it's the, you know, not necessarily like the board of directors teams,
but yeah, like the senior leadership team of companies.
What have you found has been like a reoccurring trait?
Or what have you seen that just works?
You're like, yes, this works, whether the team's 50 people, five people, 100 people,
like this trait or these traits seem to really work in terms of helping a company grow and stay successful.
Sure.
So one of my favorite traits and I look for it in people, I try and practice it myself,
albeit imperfectly, is what I call the you manage me or I manage you principle,
which would you prefer? People are like, what, what do you mean? And I think that most leaders think that the job of a leader is to manage down to others. If I said to you like, oh, you're a new manager, what do you do? Do you manage others? Do you manage others? The typical response is, oh, I manage others. And I'm like, really? Is that the path to fastest leverage and scaling for yourself and that person? And if you just step back and reverse it for a moment, think about what happens, right? So I'm a leader. I don't know about you guys, but you know what I really love? I love highly leverage interactions where I meet up with somebody. We talk about a topic. It's
pretty efficient, time efficient. It's pretty effective. We both learn something and we move on,
right? By the way, I'm plenty opinionated, as you can tell. So in the absence of somebody
coming into my room with an opinion, they will leave with my opinion. I will say to people,
if you walk in with no opinion, you will leave with my opinion because I can't help but be
opinionated. But I'm like, but if you want the higher leverage interaction where we both scale
and we both get joy, it looks something like you walk into a room expecting to manage me. I'm your
boss, but you walk in with an agenda, you walk in with your own vision, you walk in with
three potential solutions. You walk in with a couple of things you want feedback on. You take control
of that dynamic the minute you do that, right? And we have a conversation on your terms, not on my
terms. And by the way, if you think that's not fun for me, it's super fun for me. Because I'm like,
oh, great. I just met this person. They're super capable. Oh, my God, look at all the stuff they're doing.
Yeah. Yeah. And I got my dose because I got to throw in my three ideas because I always have three
ideas. And, you know, that was really fun and interesting and leverage. And now I get to turn around
and go do that again with somebody else. And I have a really fun day when I do those things.
Nothing drains me more than feeling like I have to manage down to people and tell them what to do.
I can also tell you nothing drains people more than feeling like they are micromanaged by others.
And so the way to reverse that dynamic, you tell people actively like, yeah, your job is to manage me.
We both scale, right?
You get your vision.
I get my vision.
I get my insight.
And we both get more leverage.
So I think that one of the traits I really like in others and I seek out and I seek to be,
as I seek to find people who want to manage up.
I feel like they learn pretty quickly how to identify their vision and share it and put problems on the table.
And I like leaders who don't hang on to control and management because they think it's a sign of their perfection.
I'm like, look, you scale when the teams around you scale.
When people become great around you, you are seen as a great leader.
So let go of this idea that greatness is in micromanaging everyone else.
greatness is in letting people, you know, show up and drive in a structured way and being able to
compliment and give them leverage to their efforts.
I really, really like that.
I really, I heard about Gary Vaynerchuk, you know, speaker Gary Van der Chuck.
I don't even know what's called Gary.
But somebody said, hey, explain.
They said, like, what's your best tip for managing people?
And he said, I work for them.
And I remember just hearing that he said that.
And I was like, that's such a great, like, tip.
But it's like I work for like they're the ones running this company.
Like I work for them.
If they need me for something, I'm going to do what they need to do.
And I can offer my opinion.
But I work for them.
And it's kind of the same concept that I think, yeah, because nobody wants to be managed.
And I don't want to manage people.
I don't want to tell them this is your next step.
And this is the one after that.
I want them.
But how do you find those people?
That's something that a lot of a struggle with is how do you find people that want to operate
that way that aren't just waiting to be told what to do?
Yeah.
You know, it's a good question because I think that part of it might.
be the construct we create. Like, you know, at some point in all of my leadership teams,
I've been like, guys, I only have one ask, please create a freaking agenda on Google Doc and start
every one of our meetings with an agenda and give me like 3,000 feet, 300 feet and 30,000 feet.
Like, what are your issues? You know, and like, so sometimes you can just create a construct
in which people feel like, you know, support and a framework in which to operate that way.
I think that's a big part of it, right? And certainly, look, I don't know about you. And like,
what do I look for natively in people? I look for, this brings us full circle. I look for people who
have shown flexibility and a capacity to operate in different environments and still find success.
And by the way, I don't mean success as it never failed. Like to me, success might be I went to a startup.
You know, I started a company. It didn't work out. But here are the five things I learned, you know, and the skills I achieved.
That to me is success as much as the person who comes in and has only ever had the perfect resume.
So I look for people who are pretty agile in their background as demonstrated by they were successful.
They managed to have impact in different environments.
And when I can see that somebody can have impact in different environments, I have a pretty good sense that maybe
they can come in and they would find this type of management style freeing.
There are other people, by the way, for whom it's frightening.
I have certainly also worked with people who want to be coached.
And I certainly, you know, there are people whose leadership styles in coaching is much better than mine.
I would not call myself a very effective, like, step-by-step coach.
There are people who really love that style of management.
But to your point, like, given my style, I definitely am looking for people who, you know,
want to scale and grow and are not completely frightened by white space while giving them
some construct in which to grow.
I really like that you're, it makes me think of, like, times where I'll give you an example,
I'm managing contractors on a project, let's say, right?
So I have a flip going or have a rehab going.
I actually have one right now.
It's a condo out here in Maui.
And I have created a situation in, and I've created a relationship with my contractor that I say, paint this,
culk this line, tear out this flooring here.
And then he does it.
And then it's like, okay, now do this, now do this.
And he'll do exactly that because that's a relationship that I as the leader, as the one
with the checkbook, have then created.
And then, and so then I get frustrated.
I'm like, why am I managing?
Why would we just do his own thing?
It's my own fault.
right like I created that expectation versus this is the vision where I want to see and then let I want you
I trust you as my contract like it's had I phrased the entire thing differently and I and at any point
we can stop and readjust too I can have a conversation on the contract like hey I was leading
this wrong I want to readjust I want to trust you let's set up a new framework for how we're
going to operate and this is the vision and and I can change that I know I just I love it yeah it just occurred to me
why I'm struggling with this. You can change it. But just to be clear, like, I think your contractor
does need a framework. Like, I think that some people, you know, some people can operate without any
framework and they create the framework. What I found, though, often is when you give people a blank slate,
it's also frightening. So you sort of to say, hey, here's the framework. So in my case, it might be like,
hey, can you come with a weekly agenda? Just put your thoughts down in this order. So like, I can see
how you're thinking about things. But I know if I didn't give them a construct, it would just be like,
what, what do you want for me? Because people are always worried about disappointing other people's
expectations. Does that make sense? So I think if you create a shared construct or worldview and
you say, hey, what do you want, you want to put your next five steps on a Google sheet? Like,
what's a like, you know, so I, I, I think, let's put this way. I've always been somebody who gave
people a lot of rope. And sometimes they're like, so kind of, you give people too much rope. And
then when they're drowning, then you like, yank it all the way back in. So I'm making fun of myself.
So I'm trying to give you better advice than that, which is really, you know, I've learned to
my own chagrin that you can't just give people like complete white space either if it's frightening
and daunting and then they do nothing. It's about that framework. Just like the book is a framework.
People like frameworks, right? They like they like a known canvas in which to paint. But you have to
trust that they can paint. You just have to give them a canvas, you know, and say this is the way the canvas
operates. This is its size. This is dimensions. And like I can't tell exactly what masterpiece you're
going to create, but I can say if you use the canvas, you'll find success. Yeah. This is what I like so much about
My company uses a system called EOS, the entrepreneur operating system.
It's from the book Traction, which I think I have, yeah, sitting here on my desk.
Yeah, and like traction is just one example, or EOS is one example of a framework that we then adopted.
Now, I could have chosen another framework.
There's lots of management frameworks out there.
I just chose that one.
And then it's like, we meet once a week.
That's what the conversation is.
And as soon as I did that, it dropped my workload down to like, I don't know, a quarter of what I was working before.
And everything just went through the roof.
I mean, just exploded in my company in a good way.
And I don't have to manage people anymore because the framework manages people.
But it wasn't just a go buy real estate, guys, have fun.
I'm over here on the couch watching TV.
Right.
Like that was just great a mess.
Yeah, exactly.
It's a, there's a middle.
There's a method, right?
So you want to agree on the method.
And, you know, a method that allows people to feel like they're getting leverage to,
not just like pulling on you.
It's draining both ways the other way.
So anyway, you asked, I think like 10 minutes ago what my principal was.
That's one of the big ones.
Okay.
I like that a lot.
What about hiring? We mentioned hiring a little bit and finding people, but in this world where like tech companies are paying, you know, $200,000 a year and they're giving free lunches and they're giving, you know, unlimited vacations. Like, how do we compete? Like the people were hiring. That would they expect the candy wall at the office and they need the ping pong table. Like what is it looking for? Well, I think people are looking for three things as we chatted about. And one is hard benefits. Like literally cash comp. I mean, people have to like make a living.
you know, provide for their families.
Of course that matters.
And it's very hard to compete with big companies.
For me, like, I didn't run like Google, but of course, I worked at Google and then
I ran Stubhub and had to compete against Google for talent.
So I totally get it, right?
So one is that.
But number two is soft benefits.
And this is one of the places where I feel like small businesses can compete, right?
Because whether or not the benefit now is remote work, whether the benefit is bring your
dogs to work, whether the benefit is like, hey, guess what?
If you have a daycare, you know, we're going to contribute.
I don't know, 10% of the cost, whether it's, you know, if you have a sick parent, you can,
you can go wherever you need to be.
I feel like flexibility in how we work is one thing small businesses really offer.
And also, by the way, generally less FaceTime.
You know, generally everyone is so productive in a small business.
FaceTime is often like when you get big and bureaucratic and you want to make sure people
actually getting done.
So when your company's smaller, like, you know, you have the benefit of actually knowing
everybody and what they're doing.
So I think the soft benefits is a place to compete.
And the last one is what I talked about.
My feeling is we're living in an era where not just millennials, but even older folks,
really care about the values of the place they work.
What do you stand for as a leader?
And I would say to people, whatever it is, whatever your value system is,
making that transparent is what people expect.
Do you know what I mean?
They come to work now, not just wanting the hard benefits and the soft benefits.
They will come to work wanting to feel like they have a tribe of people with whom they share,
you know, a view of what's important and what's right.
And I think we can all agree that that's been, you know,
know, something has become even more apparent over the last five years, not just for millennials,
but quite frankly, you're Gen Z, but for all of us. And so that's another place to compete.
What do you stand for? Yeah, that's cool. Yeah, one thing I've said in my business. Now,
not all companies can say this, but I let, but like in real estate, we kind of can is that, like,
if you work for me, like, I might, my hope is that this is the last job you ever have to have.
Like, maybe you'll have other job in food, but like, that's kind of that third thing.
Like, I want you to come on not just as an employee, but I want you to like, look, like,
be an apprentice.
Change a very mindset.
Yeah, yeah, exactly.
Exactly.
Yeah, it's that model.
Yeah, I think the model of apprenticeship is really powerful.
Yeah.
I think the model of apprenticeship is really powerful.
Yeah.
Because people get to be very proximate, right?
That's something you don't get in a big company.
Again, you get it's hard to learn faster working with you.
And I think it's hard to underestimate
make those benefits. Yeah, really good, really good stuff. All right, well, David, I've been
hugging the thing. Any questions you want to ask of a Silicon Valley powerhouse here before we
move on to the famous four? So, Kinder, starting from the bottom working your way up to CEO,
sitting on multiple boards, you really have a vast array of experience in seeing what works and
what doesn't work in different places. Is there a key piece of advice, maybe like a fundamental
understanding or a skill set that you tell people, hey, if you want to be successful,
overall, this is what I would have you focus on?
Sure. I would say, I have one phrase that I believe, and I don't think it's, I think it's
very complimentary to this point of view of how you become a risk taker, which is do great work
for great people. It doesn't even matter what. Like, people think it matters what? And I'm like,
no, no, it matters who. Do great work. So yes, hustle, flex, adapt, you know, soak it all in,
apprentice for great people. And great people doesn't mean the nicest people. It doesn't mean like,
it means people who share your values and can teach you something and who you admire for their
capabilities, right? So shared values, really like people you'd be lucky to be in a room to learn from
and just like hustle for those people. Like 99.9% of my success is doing great work for great people.
And like it kind of then didn't matter what the industry was or whatever. I found joy in my job and
they saw the best of me. Oh, that's really good. That's so good. All right. We got to slowly start working
towards the end. We're going to move to our last segment of the show. And that
is called our
Famous Four.
This is the Famous Four.
The part of the show, we ask the same four questions
every guest every week.
So we're going to throw them at you.
Is there a habit or trait
that you're currently working on improving
in your own life?
Not letting people finish speaking.
I'm always thinking so fast
that I finish people's sentences.
It's my ongoing work.
I can't stop my great.
I'm glad it's not just me.
Okay, next question.
Do you have a favorite business book?
It used to be good to great,
but now I'm going to give you my second one,
which is growth beyond
the hockey stick for McKinsey, which analyzes, you know, strategy beyond the hockey stick.
Sorry, I'll say growth beyond the hockey stick. It's actually called strategy beyond the hockey stick by
McKinsey, which analyzes why, you know, a set of companies over 30 years become outsized performers.
So I like that plus good to great. Good to great. It's an old classic.
Strategy beyond the hockey stick is like an even more recent framework.
And the hockey stick is the understanding of like linear or a geometric progression of your slowly
learning and then boom, you hit an inflection point and success takes off.
Yeah, growth beyond the hockey stick, like how companies really, like, succeed over a long period of time.
Beautiful.
Okay.
What about some of your hobbies?
Tennis, these days, though, I just hurt my hand.
Tennis skiing, fashion decor, my kids.
Those are the five.
You ripped those off very fast.
Have you answered that question before?
Tennis skiing fashion decor.
And my kids.
And my kids.
They're still a hobby.
They may not want to be a hobby any longer, but there's still my hobby.
All right.
Then my final question, what do you believe sets apart success?
successful entrepreneurs from those who give up, fail, or never get started.
It's kind of what you answered a minute ago, but maybe you got another piece of advice in there.
Yeah, my other piece of advice is that entrepreneurs who win consistently choose possibility.
They underweight a single choice and move in favor of knowing they have multiple choices to make between now and success.
And they just keep iterating.
Okay, that's awesome.
Last question of the day.
Where can people find out more about you?
You can always find me on LinkedIn, just at my handle, Sue Kendrickson Cassidy.
or you can find it more about the book at the book website,
www.
www.
Chosepossibility.com.
All right.
Thank you, Sukkinder.
I really appreciate you sharing your wisdom, your experience, your encouraging words.
Everybody, please go check out the book.
If it's half as good as this interview, I know that you will love it.
Thanks again for coming on.
Any parting words before we get out of here?
No, I loved it.
You guys did an awesome job.
Thank you for having me.
All right.
Awesome.
Thank you very much.
This is David Green for Brandon,
the $75 million man Turner, signing off.
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