Episode Transcript
Kirk: This week's guest is a writer, entrepreneur, speaker, investor, and there are just so many ways to describe him. He began his career in tech before the economic downturn ran him out of town, and he went from living in a penthouse to his parents' house. He went on to write a book called Hunting Discomfort: Leadership Through the Pain Points. He's going to be a speaker at this year's Construction Leadership Conference. Please help me welcome, Sterling Hawkins.
I was wondering, what is the last song that you had stuck in your head?
Sterling: The last song I had stuck in my head.
Kirk: The ear worm that you just found yourself humming all day, despite the fact that you didn't want to be.
Sterling: You know what's really funny? I heard it somewhere, and I couldn't get out of my head. It was that memory song from the musical, Cats, way back. How funny is that?
Kirk: That one's a brutal one to get stuck to because it won't go away. It's a sticky, sticky song.
Sterling: I was at the gym this morning trying to pump out a couple of sets to stay healthy, and I've got memories going through my head. I'm tearing up a little bit.
Kirk: I'm sorry. The visual of that is pretty awesome. I tell this story. I used to be in a motorcycle club, a traditional bunch of guys wearing leather jackets motorcycle club. But I am not your traditional motorcycle club kind of guy if there was something to be said for what a traditional motorcycle club person is.
We pulled up to this red light, and the president of my club has these speakers and he's blasting AC/DC. He yells over to someone else who's blasting some Metallica. I have earbuds in because I don't have speakers on my bike.
They yelled over and they're like, hey, Kirk, Kirk. They're like, what are you listening to? I was like, Matilda soundtrack. They're like, what the heck is wrong with you? I'm so many things, but with AC/DC, Guns and Roses, Metallica, to mention Matilda soundtrack, and that's just how I roll.
Sterling: We all get something. I think some music from our childhood, from life, or just because it's so moving, I think just stays with us sometimes. I'm a big fan of whatever's lighting that fire inside, you should do that.
Kirk: Absolutely. Obviously, we want to talk a little bit about your book, your hashtag, and your experience. I've read your bio, and I know a little bit of your story, but can you give me the short version. It was 2008, you're a tech entrepreneur. What happened? Tell me the quick version.
Sterling: It was actually 2004. I grew up a fifth generation retailer in my family's supermarket. Right out of college, I thought, you know what? I want to do something that capitalizes on this knowledge, this life that I've had, but it's time to spread my wings a little bit.
So I started a retail software company with my dad. Long story short, we sell it to a group in Silicon Valley, where it becomes part of this Apple Pay before Apple Pay. We raised hundreds of millions of dollars, multi billion dollar valuation. Have you seen that movie The Wolf of Wall Street?
Kirk: Yes.
Sterling: It was like living a scene out of that movie for a while, models in the office, parties at the four seasons.
Kirk: That can be really great or not so much, but yeah.
Sterling: It was the great part in the beginning, and then the not so great part when the housing market collapsed. Our funding dried up and the entire company went bankrupt. Half a billion dollars gone. It led to one of the hardest, darkest points of my life because not only did the company collapse, but so did I. I ended up playing out the sad country song of a story going from a penthouse, living the dream in Silicon Valley, to my parents’ house.
It was then that I made this decision. It was a very coherent decision that I'm not going to go down like this. I've been avoiding, denying, and just surviving for so long. After that company collapsed I decided, my life is now going to be going after those things that make me uncomfortable to be free from them. And the rest is history.
Kirk: I really liked that. I do have so many follow ups, but your hashtag is no matter what. What does that mean? What does that speak to? What is the message behind no matter what?
Sterling: In that time at my parents’ house, I'm down and out, six figures of personal debt. No matter what was just a personal mantra, honestly to get me out of bed in the morning, to call my creditors. Just baby steps, one foot in front of the other.
I recall, there was this thing my mom said when I was younger. She said, the way out is through. I thought, you know what? I don't have anything to lose. I'm going to put this thing to the test.
The thing that scared me most was speaking in public, believe it or not. Ironic, given what I do today. I think I've always been shy, but it was something about that company collapse and my identity being somewhat lost in that whole process, that I couldn't do it. It was debilitating.
I ended up applying and getting accepted to speak at this conference in Singapore that went incredibly well. It was actually the beginning of my entire speaking career. I was like, my mom was right. The way out is through. We just have to go through no matter what.
Kirk: Obviously, half a billion dollars on one day and six figures in personal debt the next day.
Sterling: It wasn't quite that fast, but yeah.
Kirk: I assume it wasn't a day. But having lived through some things like that, it feels like it happened much faster than it did. I don't want the question to sound as trite as it's going to, but any regrets? What would you have done differently? Nobody has a crystal ball, but did you handle it correctly?
Sterling: No. It's not a regret because I wouldn't understand what I know now without it. I'm grateful for the experience and all the pain that went with it. But the mistake that I made is when the company was collapsing, I started to withdraw from people and communities. I got invited to these fancy trips and these big dinners. For a while, I would continue to go, until I racked up all this debt. I wouldn't ask for help.
People would say, oh, how are you doing, Sterling? What are you doing? I would say, "I'm fine." It was really being embarrassed. There was a lot of shame going from that success to the failure that I had run into. It wasn't until I really bottomed out that I said, I'm doing this to myself. I've been avoiding the discomfort of sharing that I need help sharing what I've been going through. It was like, this did happen in a day. As soon as I made that switch, things started to change.
Kirk: Obviously, there's no crystal ball. Other than The Big Short guys, nobody saw the housing [...]. Other than the movie, about the people that did see it coming, nobody saw it coming. You are a successful tech entrepreneur building this empire, if you will.
Sterling: You make it sound better than it feels on a day-to-day basis.
Kirk: You know I'm a storyteller. There was no way to see the dark horse coming. How do we prepare as business owners, as contractors, as laborers? We are The Association of Union Constructors. We are 14 labor unions. We are 1800 contractors.
We are millions of individual tradesmen and laborers, and 3D printing roads affects the pavers' jobs. There are things that are out of our control. How do you chase discomfort when the industry is moving around you outside of your control? How do you handle that?
Sterling: There's some good news. Have you ever stubbed your toe before?
Kirk: Never. Not once.
Sterling: Everybody stubbed their toe, unless you’re some kind of a super person. That's physical discomfort. Maybe you've been through emotional discomfort or some of the folks listening. A new tool gets launched or new technology, it makes you feel a little bit emotionally uncomfortable. It turns out that physical, mental, or emotional discomfort, the brain and body process it almost identically—researchers at the University of Michigan—so much so you can take acetaminophen like Tylenol that it will help you with emotional pain.
All the disclaimers about that. I'm not a doctor, I'm not a biohacker. I don't suggest you do that, but what I do suggest is that where we meet discomfort is the same anywhere. We can grow our capacity to deal with it everywhere. It's a muscle you can build.
You go to the gym to build your biceps. You hunt discomfort in no matter what form it's in, if you want to grow your resiliency, your breakthrough results, your growth in any capacity. As these new tools, these new innovations, these new disruptive things that are happening out there in the world, we're preparing ourselves every single day as we open ourselves to discomfort of any sort.
Kirk: Okay, I like that. I actually had recently read that study. That's an interesting thing to note. That's a cool thing to reference. I liked that. I guess the question is, where is the line between hunting discomfort and creating drama?
We've all seen the person who's like, dude, you're making this way harder than it needs to be. There's one thing like, hey, don't lean into this kid. Chase the discomfort/don't be the problem. Where's the line between those two?
Sterling: I think the important line is between discomfort and real danger. There is a difference between those two things. I'll give you an example. I went skydiving a couple of years ago with my sister for her birthday. She's like, Sterling, no matter what, you got to jump out of a plane. I'm like, okay, let's give it a shot. I don't know if you've been skydiving.
Kirk: It was six weeks ago for the first time. Literally, two months ago for the very first time.
Sterling: And how was it?
Kirk: I was fine all day. All day long, I was like, this is going to be great. Then I got on the plane, and my heart stopped. We're climbing at a 45 degree angle and I'm like, what are we doing? What are we doing? What are we doing? Then the door opened and I was like, this is the stupidest thing I've ever agreed to.
They told me at the beginning, you cannot be sarcastic when they asked the question. This is not the time to joke. When they say, are you good, you have to be honest. We cannot make you jump. They're like, are you good to go? I look at him and I'm like, uh huh. All of a sudden, I get my 230-pound person thrown out. I'm like, I guess this is just what we're doing now.
At this point, I am surrendering to gravity, the parachute, and experts. We're just going to see how this goes. I was fine all day. I was fine on the way down. But that three minutes of approaching the ledge, no, I thought I was going to die.
Sterling: It's exactly the same for me. It was terrifying. I could hardly speak myself going up in that plane. But I did some research afterwards, and I found out that the risks of jumping out of that plane are far lower than just driving there. The difference between the discomfort you're experiencing and the danger that's actually there.
As you can draw that line, you can understand what's happening in the laws of physics and hard reality. You can start to separate, hey, am I just being dramatic here? Or is there something I actually need to worry about and deal with?
Kirk: Let me try to draw that back to something very real for our listeners. Our industry is on the verge of a generational shift. The union membership is at an all-time low. It's right around 10%, not just the trades, for all union membership across. It's right around 10% depending on who you ask in the survey, the study, and stuff like that, which it's been as high as 40%–60% as 50 years ago.
That is beyond discomfort. That is terrifying. That is paradigm altering. How do we fix that? How do we get people into the trades? How do we differentiate, like you said, that danger from that discomfort and operate in a pretty stark reality?
Sterling: Oftentimes, I think many of us are focused on the finite goals that we have. How many members do we have? How large have we grown? How many projects are we on? Those are really important. We have to pay attention to those things, but they're not the most important things, at least according to German-American theologian Paul Tillich.
He says, we spend almost all of our time on those finite things, but what's actually important to us are the things that, no matter what happens in the world, can't be taken away from us. Things like love, joy, peace, and gratitude. Those are the infinite ‘no matter what’s, things we can call on any time. As we can align our lives, our businesses, and the impact that we're making in the world with what's ultimately important to us, those finite things really start to work out in much, much better ways. Does that make sense?
Kirk: Yes, I understand what you're saying. I'm trying to make it fit in the context. What's the action item? From Joey with the hammer, I get it. I need to worry about my kids, my wife, my life. I get it. Their discomfort is, can I put food on the table? Got it. You go up to the contractor, and he doesn't have one table to put food on. He has 40 tables to put food on.
I was an entrepreneur for many, many years. People were talking about, you need to just worry about putting food on your table. It's like, you don't even begin to understand. I have 10 tables to put food on. If I decide not to come into work, lots of people suffer beyond just my children.
We now have this next group, but it isn't just Joey with the hammer. It's now this contractor that has 40 tables or 400 tables to put on. You go over the labor unions, and they have hundreds of thousands that they need to worry about, these larger groups. How does chasing discomfort work when you are worried about a statistically large group and not just your no matter what, but your group's no matter what, your tribe's no matter what, your industry's no matter what?
Sterling: When people see my book, it's called Hunting Discomfort. Some of the snap judgments I get sometimes. Or, Sterling, look at my business, my bank account, my family, my relationship. I don't need to hunt for discomfort. I'm surrounded by it.
Kirk: It's right here.
Sterling: Right. Look at the world, Sterling. Who needs more discomfort? I get that. The world's an uncomfortable place. There are things that we need to do, not only for ourselves but for those that are dependent on us, those that we serve.
My answer to those folks are always the same, which is, if you're surrounded by discomfort, you're not hunting it. You're living with it. You're probably rationalizing and placating why you have those uncomfortable things in your life.
As you can get to the root of those things, understand where that discomfort is coming from. It starts to free you from it. Not circumstantially free, not when I have this much money in my bank account, or when my kids go to college, or whatever it is, but truly free, because it's not based on anything except you.
Kirk: I like that. I like some of that. I see how that applies. I know, I definitely understand.
Sterling: I see the wheels started over there.
Kirk: There's a lot of this kind of talk, the inspiration/motivation, whatever word you want to use, that makes absolute sense on a personal level. I know, personally, and I know you do too just from the story you told at the beginning, what it's like to know that it's not about my discomfort. It's about, will braces get on my employees' kids?
It's not about my discomfort. It's about making sure that I'm providing not just for me, but I'm providing for my people, for my industry. I totally hear what you're saying, but I'm trying to figure out how we can make that something that these guys can act on. What does that look like? How do you chase discomfort when it's not your mortgage on the line?
Sterling: Discomfort is very personal just by nature. I think one of the traps of it is understanding it. It's distinct and different from going through it. I think that's where a lot of these influencers and memes go wrong. It's all positivity, and they're saying the right things.
But they forget, hey, wait a minute. I need to slow down for a moment. I need to understand what that discomfort is about my life, or the discomfort, which might sound like my fear of being able to provide for those people that are dependent on me. When you slow down and you start to feel some of those uncomfortable feelings, it starts to let them move through you, so you're forever free of them.
I think one of the tactics is to slow down. Understand what it is that maybe you've been avoiding, denying, or surviving. Reconcile that, and then look forward to saying, hey, what action do I need to take next from the new place that I'm in?
Kirk: That makes absolute sense from an interpersonal and personal level, but do you think that works to the CEO of a company? Do you think that works for organizational shifts, not just personal shifts?
Sterling: No question. The work that I do is not only with individual leaders, but oftentimes with the executive teams of companies. The first step always is, let's identify the discomfort and the limiting beliefs that are holding us back. I believe that you, me, and all of us have this infinite potential. The only reason it's not unleashed is because we have these limiting views about what we're capable of, what's possible in the industry, the impact that we can make in our business and in our lives.
As we can set those things aside, we can start to unleash something that's much greater than anything in this circumstantial world. We connect with inspiration or source energy that starts to draw us forward and becomes not like a PR mission that some marketing group has put for the company, but something that lives true in the hearts of the leadership. That serves like a ripple effect out into everybody that not just works with those people, but interacts with them anywhere.
Kirk: That one really resonates with me. One of the things that I always try to tell people and makes people very uncomfortable very quickly is that it's never about the money. I feel like it's always about the money. It's never about the money, ever.
Even my boss who will absolutely listen to this and come and talk to me later when he hears this episode, it's never about the money. You can prove it. There's always something that drives. Money can buy it, and money makes it feel better. Money makes the discomfort go away, but there's always more to it than the money.
Sterling: Totally. It's our views of how we're assessing ourselves, others, and the world. As we can sit back and reflect on what those views are, I promise you, the money comes. It's not this woo-woo feel good like, oh, just watch that movie, The Secret, and your dreams will come true. I don't mean it like that.
This is hard work to sit down and face some of those beliefs that you have, core beliefs. Axiomatic beliefs are hard. It's uncomfortable, and at the same time, it is transformative for everybody that does it and everybody that's around them.
Kirk: I really like that. Just wrapping up, one last Hail Mary of an open-ended question. It can go anywhere.
Sterling: We're stepping into the unknown right here.
Kirk: Again, I start off with a ridiculous question. I end by throwing you off a cliff. I want to see that it's open ended to the point of, like you said, not the memes, not the platitudes, not the feel goods, not the hashtags, but the actual action.
Tomorrow, when someone listens to this and they go, I listened to it, when they wake up, what do they do? What's the verb? Not the feeling, not the thought. What's the first step? What's the first action? What does it look like? What do they do?
Sterling: I got a great one for you. Every day, do at least one thing no matter what. It could be a big thing or small thing, it could be call your mom, could be make cold calls, could be talk to a client, or get whatever piece of work done. But if you wake up in the morning and you say, I'm going to do X no matter what, and then you do it, it starts to free you of the circumstances of the world. You start to know yourself as the kind of person that can do things that you really committed to doing. You don't even have to do #nomatterwhat. You can just say, no matter what.
Kirk: Awesome. I appreciate that. Sterling, it has been great talking to you. I look forward. You are going to be one of our speakers at the Construction Leadership Conference in Savannah.
Sterling: I am. I can't wait to join you.
Kirk: I will be excited to meet you in person, and I'm looking forward to it. Thank you so much for coming on the show today.
Sterling: Thank you so much for having me. It's been an honor.
