BiggerPockets Podcast 495: The Science Behind Taking Risks (and Why They Definitely Pay Off)

BiggerPockets Podcast 495: The Science Behind Taking Risks (and Why They Definitely Pay Off)

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It 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 they 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.

Click here to listen on Apple Podcasts.

Listen to the Podcast Here

Read the Transcript Here

Brandon:
This is the BiggerPockets Podcast show 495.

Sukinder:
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 realize something about yourself and your ability to respond, to be flexible, to be resilient and to take risks when times are tough. Imagine what you could do if you took risks proactively towards the thing you want. Just not when you’re backed into a corner.

Speaker 3:
You’re listening to BiggerPockets 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.

Brandon:
What’s going on everyone? It’s Brandon Turner, host of The BiggerPockets Podcast here with my cohost Mr. David framework Greene. What’s up man? How you doing?

David:
I’m good. I got my condos in Hawaii finally getting work done so we’re upgrading those puppies and I’ll have my first air and B’s up pretty shortly here.

Brandon:
Air and B’s? Is that a new thing?

David:
Did I say that? Short term rentals is what I meant to say.

Brandon:
Air and B’s. All right, 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 have to share him here because I’m just about done with him.

David:
I don’t think there’s a higher compliment in a friendship than sharing your contractor.

Brandon:
Nope. I agree.

David:
I mean that’s like … I’d share my toothbrush before I’d share my contractor.

Brandon:
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. About kind of a different twist on how we take risks with somebody who has been in an 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 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 book out and you’re going to hear more about that as well today. But we’re going to talk a lot about risk. We’re going to talk 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.

Brandon:
I mean, I had a realization in this interview about working with contractors that I wish I would have had 10 years ago. It would have 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?

David:
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 inside trying to figure out what to do and we know what to do. And it’s that 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 this 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 up.

Brandon:
Powerful stuff man. Good job. Way to wing that at the last second. All right. I think that’s pretty much ready go. Anything you want to say before we bring in Sukinder?

David:
No. I really like today’s interview. Let’s grab her and bring her in now.

Brandon:
All right, here we go. Sukinder, welcome to the BiggerPockets Podcast. Awesome to have you here.

Sukinder:
Thanks Brandon. Thanks David.

Brandon:
So let’s dive in. So you have been on … I was reading your bio. A ton of high profile boards. Ran successful companies. Started companies. You’ve been around the whole Silicon Valley 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 get into this world where you’re this powerhouse in Silicon Valley? How did that happen?

Sukinder:
Well, it’s so funny you ask that. People are always like, “Oh, Sukinder, what happened? How’d you end up in Silicon Valley?” And we all have this image that everybody’s 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, “Oh dad, what are you having me do?” But he had us, believe it or not, working on his taxes, like his ledgers, by the time I was seven or eight years old. Preparing my dad’s books at the end of each year to file his taxes was like a family affair. And so 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 investing. Like who knew?

Sukinder:
Like I remember when my dad … And my dad was older. So he was probably in his 60s or 70s. And I remember calling him up. His broker. Because you remember, it used to be that you read stock prices in the newspaper. Right?

Brandon:
Yep.

Sukinder:
He had this magnifying glass because he couldn’t read the numbers, they were so small. And he’d call his broker and he’d be like, “Tom, let’s buy some AOL.” I mean, I didn’t even know what AOL was but here was my 60 to 70 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 end up in investment banking. By the time I was in my mid 20s I was like you know, I really want to be an entrepreneur. 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.

Brandon:
Yeah. So what did you start? What was your very first business in?

Sukinder:
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 cuff links for women. I know. Don’t laugh. But I was like, “You know what? I’m wearing all these suits and everything that’s available for the guys.” Because I was a Wall Street banker. 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 bags of cuff link prototypes with me though 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 Junglee 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 Yodlee.

Sukinder:
And for those of you who don’t know what Yodlee 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.

Brandon:
Very cool.

David:
Can I ask you a random question about Silicon Valley?

Sukinder:
Sure. Please.

David:
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 LY. Yodlee, Trendly.

Sukinder:
What is Musically? Wait, you’re thinking LY. Yodlee was L-E-E my friend.

David:
Same thing.

Sukinder:
Before they would be L-Ys. They were the L-E-Es. So keep in mind, I was at Junglee, I was at Yodlee. Yeah, yeah. I am the original hipster. Like there was a lee, L-E-E before an L-Y.

David:
I’m wondering if you started that whole trend. We have the … It might have been you.

Sukinder:
It could be. Oh my god. It might have been us. I will just say there’s a whole set of companies started by Indian co-founders. Like I said, the company I worked at was called Junglee and then my company was called Yodlee. Yeah. I think we did. We get some credit right?

David:
You should. 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 something with their names and write now it’s to add Y to the end of a normal word and that becomes … Whatever you’re selling right?

Brandon:
BiggerPocketsly.

David:
Yeah. That’s exactly right.

Brandon:
Yeah, we should do BiggerPocketsly.

Sukinder:
No, but it’s true. For whatever it’s worth I own a couple of domains that end with an LY. I don’t know what to do with them yet but I did buy a couple myself.

Brandon:
That’s funny.

David:
Oh, I think if you got in on that real estate early you just picked every word you could and added LY and bought the domain you probably made a killing.

Sukinder:
I love it.

Brandon:
All right. Then you served on a lot of boards, you did a lot of that stuff, and now here we are in 2021 recording this. And we just came through a hell of a year to put it lightly. A lot of things changed during this year and a lot of people … 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 … You talk about risk, 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?

Sukinder:
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 risks and how to take risks systematically. How to kind of buck this idea that it’s a one off event. That 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. We worry about what will go wrong. We fear failure. We worry that somebody will laugh at us. We worry that we’ll lose money. We 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. The things called subway events. Like you can predict the subway’s going to come and it’s going to be either a couple minutes early or a couple of minutes late. So you can predict the range of volatility on a subway. And so you can plan for it.

Sukinder:
But what happens when a coconut happens? A coconut is literally a coconut dropping out of a tree, hitting you on the head and you die. That is the definition of a coconut event. So we all just had a coconut event and it turns out that coconut events teach us a lot about our ability to take risks and to be resilient and take risk in the face of harm. So we always were like, oh my goodness. Why is it so hard for people to take risks 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 realized something about yourself and your ability to respond, to be flexible, to be resilient and to take risks when times are tough. Imagine what you could do if you took risks proactively towards the thing you want just not when you’re backed into a corner.

Sukinder:
So I think the pandemic taught us all about our ability to take risks and it also taught us that even if you don’t want to take risks, risk still happen to you. So isn’t it better to kind of embrace it proactively and take advantage of it to its fullest?

Brandon:
In your research have you found that risk takers are generally just more … Is that a sign of success? Like the more risky you are … Maybe that’s the word. Adding a Y to it. The more risky you are the more successful you become. Do they correlate?

Sukinder:
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 into space. Pretty amazing. I’m sure you guys agree, right?

Brandon:
Yeah.

Sukinder:
Or you look at Elon Musk or you look at Jeff Bezos. And we often think oh my goodness, risk taking is for the riskiest among us. Does that make sense?

Brandon:
Mm-hmm (affirmative).

Sukinder:
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. Jeff Bezos, do you know how many attempts he took at Amazon Marketplace? I know. I was like the first the company he bought to attempt Amazon Marketplace. 1997. No, 1999. 1998. Sorry. Jeff Bezos bought our company, Junglee. How long did it take for marketplace to get successful? Jeff Bezos killed multiple versions of marketplace before it ultimately happened. So we tend to think that 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 in. 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 and you go oh my god. Rather it’s that they’ve been practicing risk taking with all its failures and successes big and small for a long freaking time.

David:
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 here HELOC or home equity line of credit. They immediately say, “Oh, that’s bad.” Or sub prime 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?

Sukinder:
Yeah sure. Absolutely. You’re hitting it. So interestingly if you looked at the dictionary, Merriam 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? But if you look at the definition of risk taking it says something more along the lines of 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 risks … And by the way, when I say risk it can mean a micro risk. You speak up in a meeting. It could be a medium sized risk like 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. 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.

Sukinder:
Like every time we take a risk we’re kind of choosing a possibility. 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. 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?

David:
Yes.

Brandon:
Yes.

Sukinder:
It’s about taking multiple risks. It’s not about the single 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 in order to start a walk in clinic. But that was a big risk where his little risk was maybe renting it out to five other doctors. 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.

Brandon:
I love that you’re saying this. 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.

Sukinder:
You got it.

Brandon:
In other words if people are like freaking out about that first deal … 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 occasionally. Like oh, I just bought this amazing … 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 risk muscle. The most important thing you can do is get started. Even with a mediocre deal. Even with a break even deal. Because it builds that risk muscle.

Sukinder:
You got it.

Brandon:
It builds that momentum.

Sukinder:
It builds momentum. It builds learning. You have a feedback loop. You can plan for your next deal better. All this abstract planning from afar and then never taking a single risk, 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. Real estate investing teaches us to do that. By the way, even tech companies take multiple risk. They take risks upon risks upon risks. Many little in order to pivot. So by the time they’ve pivoted 180 degrees it’s actually the result of probably 50 different choices, not a single large gigantic step into the unknown. Yet when it comes to our careers and ourselves we really don’t embrace calculated risk taking. And I think that’s the opportunity.

David:
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’ve got a new job, the risk is always highest in the beginning, right?

Sukinder:
Mm-hmm (affirmative).

David:
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?

Sukinder:
I do. And the irony is … I think most people presume … I think there are two things. Psychologically the first risk is the hardest. Does that make sense? Psychologically.

David:
Yes.

Sukinder:
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 at a minimum you know how to respond. You learn how to respond. So psychologically the first choice is the scariest. Ironically the best way to get into action is to think about the smallest micro risks 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 is in continuing to choose. I always say to people, 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, to your point. So I think psychologically it’s the hardest to take the first risk. Ironically you can start with the smallest smidgen of a moment and get into motion.

Brandon:
What’s an example of that? Like a smaller kind of micro choice.

Sukinder:
Sure. Like anything. Like we were chatting about … Let’s say you think you want to go join a startup and you just don’t know what it’s like. The micro choice is you don’t have to take the first recruiter call that comes your way. The micro choice is you could go do five informational interviews with five people who are in startups. The micro choice is you could go figure out if there’s a new emerging division at your company. The micro choice is you could start a side hustle. The micro choice is you could go take 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. So I always think that micro choice is the smallest choice you can make that gets you information and learning and some sense of what it will be like.

Brandon:
Is that the same things as … You mentioned earlier, minimal viable choice. Is that what that is?

Sukinder:
The MVC. Yeah. I always say when we’re contemplating bigger choices I have this 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, suppose you’ve evaluated 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 personal kitchen cabinet. All that stuff. You still can’t choose. What I would say is 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 that’s all that matters. Whether you make the choice in one big swoop or whether you might 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 did something after you did all that evaluation. If you can’t bear to do the big choice, do the small choice. Any choice is a good choice to get you started.

Brandon:
I like that a lot. When I think of putting this in an example of getting started with a real estate investment portfolio for example, you don’t have to commit to buying a property and committing to hundreds of thousands of dollars right away. That’s the scary, that’s the big picture right?

Sukinder:
Yeah.

Brandon:
The beginning is like you could spend an afternoon going to an open house. That’s a super low easy things to do.

Sukinder:
That’s an NVC.

Brandon:
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. Analyze some properties. Run the numbers and see what you think.

Sukinder:
It’s amazing. Right. And don’t you find it interesting … And I know we keep hopping on this so I’m happy to move on. I always feel like people look at big binary choices and 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 get information. Get going, discover, pipeline, learn. These are all great ways to spend your time. And I always am like if you can’t risk a little bit of time, what makes you think you can risk your whole career? If you can’t risk a little bit of time to go to an open house-

Brandon:
Yeah exactly.

Sukinder:
What makes you think it’s the right thing buy a building?

Brandon:
Exactly. I use the analogy often of like … I used to live in the pacific northwest. Silicon Valley, you’re familiar with this as well. It gets foggy sometimes. So you’re driving in the early morning and it’s foggy. You can’t see two miles down the road. And so this fear built up. Like oh, what if there’s an accident? What if there’s a deer in the road? What if there’s an animal? What if I can’t … 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. Take it easy. Ease off the gas. Turn your high beams on.

Sukinder:
I totally agree. 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 making a move is like being on the monkey bars. We always think we need to see to the end of the course but you don’t. You just need to reach for the next rung. And if you reach for the next rung-

Brandon:
That’s a better analogy.

Sukinder:
Yeah. It’s a good one right?

Brandon:
I love that.

Sukinder:
Yeah. I like the monkey bars analogy. I can’t take credit for it but I like it.

Brandon:
I really like that a lot. Yeah. It’s so much easier that 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 business so I can quit my job? That’s a scary big picture thing so stop worrying about it.

Sukinder:
Absolutely. And look, I mean all of these strategies are just to get in motion. I think it’s also interesting for us to talk about if you want, how do you get smarter about the risks you take? First and foremost you get to get in motion. And a lot of that is like debunking this idea that there’s a single choice. The minute you know you can keep choosing, the minute you know that 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 and a fifth then a 10th. 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 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 hope and a prayer. They tend to sort of overweight that everything is their own execution. Like I need to be a perfect executer. This is why you see these … I’ve been a CEO before so I see all these perfect plans.

Sukinder:
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 maybe the more strategic risk taking approach is to plan for what can go wrong.” And David, you talked about this earlier. Like this links very much to fears of failure. Like it’s not just 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 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 than could go right, you’re likely to weirdly conquer your feal of failure and be able to go pursue a choice rather than 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 risks they’re going to take and actually get them into motion too.

David:
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. 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 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 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 like how I felt. I want to take another one.” Those progressive steps get you 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 workout 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.

David:
I would bet you Sukinder 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, “Hey, 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.

Sukinder:
Yeah. I think that true. By the way, I mean make no mistake, I always have a plan. So I call it my whiteboard plan which is I kind of roughly knew I always wanted to be a CEO. And I roughly knew I wanted to do sort of be the CEO of a consumer company. But I didn’t know how to your point precisely. And getting into motion gave me the confidence that 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. It’s like technology, 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 our success is not about our execution. It’s about the macro environment and the headwinds, tailwinds. In the world of real estate, it’s like 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 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. 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.

Sukinder:
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, my career looks pretty cyclical. People think of it as linear because they only want to manage. They only see the peeks of my career. They’re like, “Oh, Sukinder, 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 the rewards that I imagine 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 the 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 was about playing out the cycles.

David:
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. These are bunch of grunting sweating people and they don’t have a background in 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?

Sukinder:
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 risks? And for those of us who have to create environments in which people take risks, what do you do? And to your point, what’s the accountability on the person involved? 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, 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 risks. Like we all I think … You know this. The research all suggests that we’ll 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. You can only really put yourself at risk when you trust that the people around you are similarly … I don’t want to say similarly minded because that means homogenous thinking. I just mean like have similar values. That the end of the day their sense and world view is similar.

Sukinder:
As we talked values is 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. You can do all the things. You can go to that crossfit gym. And if that crossfit gym … 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 the person at the front door of the gym at the countertop, even if they look beautiful 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. 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 where we think we have values fit.

Sukinder:
And to your point, it’s to take those little risks. It’s to manage your own fear of failure by thinking about what’s the worst thing that could happen if I act? I always say that. So that’s in our realm of what’s possible. I think if you’re a leader who’s managing environments 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 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 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. The CEO or the leader in question like treats only certain people well and not others or always uses one person to demonstrate the exercise who’s absolutely impeccable. Like these are all thing that 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.

Sukinder:
So I think as leaders our opportunity is whatever environments we create we have to expand access to what’s possible and show multiple types of success. Celebrate multiple types of risk taking. Celebrate different types of risk takers. When the introverted person in the room speaks, celebrate it. When somebody who never says something in a room says something smart, say oh. Reinforce it five times over and be like, “Oh, like Brendon said in that other meeting.” Give credit. These are all things you can do to make it possible for people to feel like they could take risk in environments you create.

David:
That’s really good.

Brandon:
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 … 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 things that we can do to try to foster more women in this industry?

Sukinder:
Yeah. 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 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 four different risk types on the book site. It’s at choosepossibility.com. You can take a risk quiz that’s less than 60 seconds to take. But interestingly when we put our risk quiz out to a sample of the US 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 contemplator. Which means pros, cons but can sometimes be stuck in indecision and have regrets for choices they didn’t make.

Sukinder:
And then on either side of that to the extreme of the calculator’s the change seeker. Someone 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 thread of acting rationally but they probably never miss an opportunity. They also might be the over committer. 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 risks. And so could that explain why women are less entrepreneurial in some fields including real estate? Potentially. But it also to your point invokes well, what do you need to do to make it comfortable for different types of people to take risk? 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?

Sukinder:
How do you highlight and celebrate those successes? How do you acknowledge what those folks needed to do differently? So I think that there are some explanations why different fields including real estate have different profiles on men and women. And I think risk taking certainly plays into it. But the other thing that plays into it is, how do we make it possible for all people in any given field to participate? 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 setting your own hours if you want to be … Let’s call it a care giver. But on the other hand it’s 100% commission based often. 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 and put it in an asset that might be locked up for a period of time. So these are all things that might give people who are more contemplators pause.

Brandon:
Yeah.

Sukinder:
And so maybe what you need to do is even identify how different people can be successful and what micro choices are available. Is there a way for someone to get started in investing in real estate through a fund or through a group of angels? These are all ways you can sort of demonstrate that it’s possible to get started in smaller ways.

Brandon:
I have a real estate fund. We raised, I don’t know, $75 million, something like that in the last year to buy a bunch of-

Sukinder:
Congrats.

Brandon:
Thanks. Yeah. It’s cool. But I would say … I don’t know if I’d say majority but I’d say it’s probably really 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.

Sukinder:
To get in. Right.

Brandon:
To feel like they’re … So I just kind of connected that full circle to what we talked about earlier is it’s a good way to … And a lot of our investors are women. A lot of them are women. They’re married couples but the woman’s the one that we talk with and they reached out.

Sukinder:
Well, yes. Leading. Leading the financial decision.

Brandon:
Yeah. They’re leading that.

Sukinder:
Yeah. Absolutely. But maybe … And again, I’m not here to theorize on your business but I think what you can do to invite in groups that are underrepresented and to make room for them, I will just acknowledge that sometimes that takes additional effort. Like it’s the same thing with 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, “I go after women and they say no at a disproportionate rate. They literally say no. I get all the way to 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 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 faceted problem.

Brandon:
Yeah. We get that same issues on the podcast itself. 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 says she won’t do it. She’s too … She wants to be behind the scenes where I tend to put this on most guys like myself, 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 a difference. But it goes too … It doesn’t mean I just accept the fact. Oh well, most of the people applying are men. It’s like well how do we encourage more women too? How do we fell more comfortable to apply? How do we reach women where they’re at? And I find this with people of color as well. Most people that apply for my job positions, the look and sound just like me. And so the question … I had a good buddy the other day called me out and he said, “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 … They’re already in your world? So how are you going into another world to attract more people and more applicants and more people?”

Brandon:
And I was like, I’m not really. I’m just relying on my own audience which is just like the self full fulling kind of cycle.

Sukinder:
Prophecy. We all I’ve in that. Yeah. You absolutely do. If you want to extend possibility you have to expand possibility. You have to just … And I understand that that takes work.

Brandon:
It does. Yeah.

Sukinder:
It also has great rewards in terms of better performance. We know that. 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, of kind of the majority origin, it doesn’t matter but go take the risk quiz and learn a little bit about your own style. Because I think I would say that like … I always think that people think they need to be this ultimately optimist to be risk takers or risky. Naturally risky to be risk takers. So I’m like nothing could be further from the truth. You just need to know what you are and deliberately make choices right that put you on the path to building the muscle and then I think optimism is the output to be honest. Becoming a risk taker is an output of the practice, not an input.

Brandon:
Oh, that’s really good. I like that. Before we let you go I do want to cover a couple more things. 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.

Sukinder:
Sure.

Brandon:
The first one, looking at teams and specifically like leaders of teams. Like whether it’s … Not necessarily like the board of directors team but yeah, the senior leadership team of companies. What have you found has been a reoccurring trait or what have you seen that just works? You’re like yes, this works whether the team is 50 people, five people, 100 people. This trait or these traits seem to really work in terms of helping a company grow and stay successful.

Sukinder:
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 mange 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, “Oh, you’re the new manger. What do you do? Do you manage others or do you let others manage you?” 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. So I’m a leader. I don’t know about you guys but you know what I really love? I love highly leveraged interactions where I meetup 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. By the way, I’m plenty opinionated. You can tell. So in the absence of somebody coming into my room with an opinion, they will leave with my opinion.

Sukinder:
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 if you want the higher leverage interaction where we both scale and we both get joy, it’s looks something like you wank 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 things you want feedback on. You take control of that dynamic the minute you do that. 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. And I got my dose because I got to throw in my three ideas because I always have three ideas. It was really fun and interesting and leveraged. 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.

Sukinder:
Nothing drains me more than feeling like I have to manage down 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. You get your 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 is 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 show up and drive in a structured way and being able to compliment and give them leverage to their efforts.

Brandon:
I really, really like that. I heard once Gary Vaynerchuck … You know speaker Gary Vaynerchuck?

Sukinder:
Yeah.

Brandon:
I don’t even know what to call Gary. Somebody said hey … 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 tip. And it’s like they’re the ones running this company. I work for them. If they need me for something I’m going to do what they need me 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 managed people. I don’t want to tell them, this is your next step and this is the one after that. But how do you find those people? That’s something that a lot of us 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.

Sukinder:
Yeah. It’s a good question. Because I think that part of it might be the construct we create. Like 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? 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. And certainly look, I don’t know about you … What do I look for natively in people? I look for … This brings us full circle. I look for people who have shown flexibility in a capacity to operate in different environments and still find success. By the way, I don’t mean success as in never failed. To me success might be I went to a startup, I started a company. It didn’t workout but here are the five things I learned 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 the were successful. They managed to have impact in different environments.

Sukinder:
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 … There are people whose leadership style in coaching is much better than mine. I would not call myself a very effective step by step coach. There are people who really love that style of management. But to your point, given my style, I definitely am looking for people who want to scale and grow and are not completely frightened by white space while giving them some construct in which to grow.

Brandon:
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. So I have a flip going or I have a rehab going. I actually have one right now. It’s a condo out here in Maui. And I have created a situation and I have created a relationship with my contractor that I say paint this, caulk this line, tear out this flooring here and then he does it and then okay, now do this, now do this, now do this. He’ll do exactly that because that’s the relationship that I as the leader, as the one with the checkbook have then created. And so then I get frustrated. I’m like why am I managing this? Why doesn’t he just do his own thing? It’s my own fault. I created that expectation versus this is the vision where I want to see and then I want you … I trust you as my contractor. Had I phrased the entire thing differently … And at any point we can stop and readjust too. I can have a conversation with my contractor and be 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 I can change that. Anyway-

Sukinder:
I love it.

Brandon:
It just occurred to me why I’m struggling with this.

Sukinder:
You can change it. But just to be clear, I think your contractor does need a framework. I think that some people … Some people can operate without any framework and they create the framework. What I’ve found though often is when you give people a blank slate it’s also frightening. So you sort of have to say, here’s the framework. 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 from 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, you want to put your next five steps on a Google sheet?” So I think-

Brandon:
Yeah.

Sukinder:
Let’s put it this way. I’ve always been somebody who gave people a lot of rope and sometimes they’re like, “Sukinder, you give people too much rope and they’re drowning then you’ll 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. I’ve learned to my own chagrin that you can’t just give people 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. 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 and say this is the way the canvas operates. This is its size. This is its dimensions. And 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.

Brandon:
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. Like Traction’s 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, this is 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 it 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.

Sukinder:
Exactly. A hope and a prayer.

Brandon:
That would just create a mess. Yeah exactly. There’s a middle.

Sukinder:
There’s a method. So you want to agree on the method. A method that allows people to feel like they’re getting leverage too. 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 principle was, that’s one of the big ones.

Brandon:
Okay. I like that a lot. What about hiring? We mentioned hiring a little bit and finding people but in this world where tech companies are paying $200,000 a year and they’re giving free lunches and they’re giving three day unlimited … How do we compete? The people we’re hiring, is that what they expect? The candy wall at the office and they need the ping pong table. What is what they’re looking for?

Sukinder:
Right. 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 make a living, provide for their family. So of course that matters. 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. So one is that. But number two is soft benefits. And this is one of the places where I feel like small business can compete. Because whether or not the benefit now is remote work, whether the benefit is bring your dogs to work, whether the benefit is, “Hey, guess what if you have a daycare we’re going to contribute, I don’t know, 10% to the costs.” Whether it’s if you have a sick parent you can go wherever you need to be.

Sukinder:
I feel like flexibility and how we work is one of the things that small businesses really offer. And also by the way, generally less face time. Generally everyone is so productive in a small business. Face time is often like when you get big and bureaucratic and you want to make sure that people are actually getting shit done. So when your company’s smaller 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 always 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 a view of what’s important and what’s right. And I think we can all agree that that’s been something that’s become even more apparent over the last five years. Not just for millennials but quite frankly or gen Z but for all of us. And so that’s another place to compete. What do you stand for?

Brandon:
Yeah. That’s cool. Yeah. One thing I’ve said in my business, now not all companies can say this but like in real estate we kind of can. Is that if you work for me my hope is that this the last job you ever have to have. Like maybe you’ll have other jobs in the future but that’s kind of that third thing. Like I want you to come on not just as an employee but I want you to-

Sukinder:
Be an apprentice.

Brandon:
Change your very mindset.

Sukinder:
Yeah, yeah. Exactly. You get to apprentice.

Brandon:
It’s that model.

Sukinder:
Yeah. I think the model of apprenticeship is really powerful. Because people get to be very proximate. That’s something you don’t get in a big company. Again, you get it in a smaller company. So I think there’s … And by the way, oh there’s one more. Right job, job moving laterally. Trying different roles in jobs. Like having two roles at once. Like these are all the types of things when people know they’re going to learn faster working with you. And I think it’s hard to underestimate those benefits.

Brandon:
Yeah. Really good. Really good stuff. All right well David I have been hogging the thing. Any questions you want to ask of a Silicon Valley powerhouse here before we move on to the famous four?

David:
Sukinder, 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 where it’d be like a fundamental understanding or a skillset that you tell people hey, if you want to be successful overall, this is what I would have you focus on?

Sukinder:
Sure. I would say … I have one phrase that I believe and I think it’s very complementary 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. 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. So shared values. Really people you’d be lucky to be in a room to learn from. And just hustle for those people. Like 99.9% of my success is doing great work for great people. And 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.

David:
That’s so good.

Brandon:
All right. We got to slowly start working towards the end so we’re going to move to our last segment of the show and that is called our …

Brandon:
(singing)

Brandon:
This is the famous four. The part of the show where we ask the same four questions to 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?

Sukinder:
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 brain.

David:
Same. I’m glad it’s not just me. Okay next question, do you have a favorite business book?

Sukinder:
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 from McKinsey which analyzes strategy beyond the hockey stick. So I will say Growth Beyond the Hockey Stick. It’s actually called Strategy Beyond the Hockey Stick by McKinsey which analyzes why a set of companies over 30 years becomes outsized performers. So I like that plus Good To Great. Good To Great’s an old classic. Strategy Beyond The Hockey Stick is an even more recent framework.

David:
And the hockey stick is the understanding of geometric progression of you’re slowly learning and then boom, you hit an inflection point and stuff just takes off right?

Sukinder:
Yeah. Growth beyond the hockey stick. Like how companies really succeed over a long period of time.

David:
Beautiful. Okay. What about some of your hobbies?

Sukinder:
Tennis. These days though I just hurt my hand. Tennis, skiing, fashion, décor, my kids. Those are the five.

David:
You ripped those off very fast. Have you answered that question before?

Brandon:
Yeah.

David:
Tennis, skiing, fashion, décor.

Sukinder:
And my kids. And my kids. They’re still a hobby. They may not want to be a hobby any longer but they’re still my hobby.

Brandon:
All right, then my final question, what do you believe sets apart 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.

Sukinder:
Yeah. My other piece of advice is the entrepreneurs who win consistently choose possibility. They under weigh the single choice and move in favor in knowing they have multiple choices to make between now and success and they keep iterating.

David:
Okay that’s awesome. Last question of the day. Where can people find out more about you?

Sukinder:
You can always find me on LinkedIn. Just at my handle Sukinder Singh Cassidy or you can find out more about the book at the book website, www.Choosepossibility.com.

David:
All right. Thank you Sukinder. 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?

Sukinder:
No. I loved it. You guys did a awesome job. Thank you for having me.

David:
All right awesome. Thank you very much. This is David Greene for Brandon, the $75 million man, Turner signing off.

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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!

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Books Mentioned in this Show:

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