Breakthrough Reinvented: Bridging The Gap Between Technology And Innovation With Sterling Hawkins

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TSP Hawkins | Breakthrough Strategies

Episode Summary:

History has proven time and time again that the breakthrough of yesterday simply becomes a necessity of today. As people of the present, the responsibility of reinventing and reimagining the modern age falls to us. Internationally-recognized thought leader and top-rated keynote speaker on innovation, Sterling Hawkins, joins John Livesay in this episode and to share how he got started in the industry in a non-traditional way. Sterling explains the struggles of coming in blind in the industry, and provides some tips and strategies on what to prepare and focus on for you to gain firm ground. He discusses the different aspects needed to be considered in breaking through and how household companies overcame the challenges in their industries.

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Breakthrough Reinvented: Bridging The Gap Between Technology And Innovation With Sterling Hawkins

Our guest in this episode is Sterling Hawkins, who is an expert at innovation specifically in the retail space. He said, “Your breakthrough potential is connected to your tolerance for risk and that change is happening at such a pace that we don’t know how to cope with it.” He’s got some insights into how he personally copes with it. Finally, he said that discomfort is needed for innovation.

Our guest is Sterling Hawkins who is out to break the status quo to create what’s possible for humanity in our time. He spent his career igniting new views and inspiring people to act on them. His journey has been nontraditional right from the beginning. Sterling grew up a fifth-generation retailer, having to master the intersection of human behavior and technology under extreme competition. In 2004, Sterling cofounded, launched and sold his first tech company, Convena, where he developed innovative approaches to beat the competition, handle high growth, and achieve performance no matter the obstacles.

He went on to be involved with the launch, growth or investment in over 50 companies. Sterling reviews over 1,000 new technology companies every year, further refining the keys to realizing breakthrough innovation. He gives back that experience as a mentor to leading entrepreneurs working through financial growth. He is the Founder of CART, which is a platform to drive the adoption of emerging technologies of Fortune 500 companies. He speaks and runs workshops around the world for Samsung and many other companies, including the United Nations. Welcome to the show, Sterling.

Thanks, John. It’s great to be with you.

I always like to ask my guests to tell their story of origin. We hinted at it with you being a fifth-generation retailer but take us back as far as childhood or school where you started to say, “I want to do something unique and nontraditional.”

I grew up in my family supermarket. I remember being 5, 6, 7 years old passing out cookies to people who were waiting in line for things and grabbing whatever we wanted to eat when we were kids. The selection is endless, especially the child. There was this defining moment for me at fifteen. I didn’t enjoy the life of a supermarket kid. My dad says to me, “You’re going to work here and we’re going to start you out at night crew this summer.” I’m like, “We don’t just get free food all the time and hang out whenever I want?” It’s a real awakening for me like, “This is work and this is how retail operates.” Looking back on it, it’s such a tremendous experience to be exposed to that level of things where I was doing everything from sweeping and mopping the floors to stocking the shelves. I worked my way up through managing most of the departments, which was a blast. It informs everything that I’m doing now because it was people-oriented.

You had that experience and your first real-life job was getting into marketing and branding, right?

It’s very difficult to start a company without a lot of experience. Click To Tweet

I wouldn’t recommend this to people but my first “job” was I started a company with my dad. It was called Convena and we said, “We’ve got a store to test things. Let’s develop some software and create a company that can deliver a personalized message to everybody shopping with us.” We built it together. We launched it in our family store. Long story short, we sold it to a group in the Bay Area, which brought me out to California and this is probably 2005 or so. It was quite a journey. We got acquired by a much larger company that went on to raise $550 million.

What’s one thing that you wouldn’t recommend doing? Is it because it was with your dad?

No. It’s difficult to start a company without a lot of experience. I tell people with entrepreneurship in general, which I’ve done a lot of. For a lot of people, I wouldn’t wish it on them because it is hard to get up every morning, making the bread, getting it done, selling it and marketing it. In fact, I’ve never had a real job in my life. You’re a jack of all trades and you get it at a point where you’ve got some support and help and you’re scaling things. You’ve got to be ready for that because there’s the sexy allure of the “entrepreneur” now. It is a phenomenal opportunity to create something new in the world. You just got to enter into something like that, acknowledging the risks you’re taking on and which you can step into.

I once heard somebody say, “You have a choice. You can work for somebody else for 40 hours a week or yourself for 80.” You’re also involved with this Virtual Reality/Augmented Reality Association. People would love to learn what’s going on in that world. When I was speaking at Coca-Cola, they were talking about using virtual reality to allow people to imagine what the coke machine would look like before it got installed in their store. That’s the baby steps of it. What do you see happening in that world?

We’re looking at over 1,000 new tech companies every single year and virtual and augmented reality is a major part of that. It’s one of these situations where the sky’s the limit and there are some great applications of VR but they’re niche. For example, a store owner being able to see a store stand or a new coke machine and what it looks like if you were to buy it. There’s a lot of gaming and I don’t think it’s reached quite that critical mass to get it in the market. It’s a lot of what I talked about, which is the turning points of innovation or the difference between the linear trajectory that most of us are on and most technologies start on and without exponentially possible.

Waze is now sending notifications like, “You’re within three miles of Domino’s Pizza. Here’s a coupon.” Google and Coca-Cola have partnered up so while you’re in the grocery store, they can tell you’re walking by the display in a grocery store and send you a coupon. That is all part of retailing, isn’t it?

That’s right. We live in a day and age now where technology is accessible to many people and it’s changing quickly that it becomes a new normal for us. A good example of that and most people are familiar with this. There used to be this massive industry called the taxi industry. The whole generation wouldn’t think twice about calling a cab. That’s what you would do in New York and other cities when you want to get somewhere without a car. They’ve spent a lot of years improving the taxi industry. They are going to take credit cards and then they’re going to improve the gas mileage and then they’re going to improve where taxis are around the city, state or wherever they are. They weren’t thinking about what’s exponentially possible and then along comes Uber. Whenever I was flying to a new city and there’s not an Uber there, I’m confused about what I’m supposed to do.

TSP Hawkins | Breakthrough Strategies

Breakthrough Strategies: It is a phenomenal opportunity to create something new in the world.
Acknowledge the risks you’re taking on and which you can step into.


It’s like taking you back in time with a rotary phone or something. You’re like, “What’s a taxi stand?”

I’m like, “There’s no Uber in the city, how do you get to the hotel?” Within five years, it has become this new normal for most of us. That’s the world that we live in now where a technology that launched several years ago is almost expected by everybody a couple of years later.

We’re the perfect person to ask this question about because we’re both living in Los Angeles. You watch what’s happening when you get off the plane. LA was probably one of the first cities to have Uber. You had a choice as a passenger getting off a plane. You could go down the stairs and wait in line to get a cab the traditional way, or you could go upstairs like you were checking back in and wait with a group of people in mass ordering Uber and Lyft. It was a bunch of traffic but it was still cheaper than the cab downstairs. It probably would take you longer than a cab would because they weren’t all lined up and people had to get there so you had to wait up.

Convenience and price saving are worth having to wait longer than it would be faster just hopping in a cab. Now, the game has changed again. Everyone has to take a shuttle or walk a mile into a location with your luggage. That’s the last thing you want to do in the rain and the line for the shuttle is worse than any taxi line ever was. You get there and you have a choice. You can order the Uber on your phone while you get there and they give you a code or you wait and you get in the line to get a cab. I got to the Uber and I said to him, “Why would anyone ever take a cab?” Because there’s no longer a savings of time. The whole thing is even disrupted yet again.

Or money in a lot of cases.

Uber is still cheaper so I don’t understand why somebody would unless you didn’t want to deal with your phone. To your point, it keeps changing and it goes, “Eventually, in a few years, we’re going to build some way to get you here faster than the shuttles.” In the meantime, we’re trying to eliminate the traffic so this concept of how we move people and how we move product whether it’s an Amazon drone delivering your food to you now. Overnight is not fast enough anymore.

“I need it in an hour or 30 minutes.”

Your breakthrough potential is equivalent to the amount that you put on the line. Click To Tweet

Domino’s Pizza is doing this. They are using artificial intelligence to anticipate your pizza order to try and shave 30 seconds off the delivery time. People’s expectations keep going up and up. Let’s talk about what you’re doing at the Center for Advancing Retail and Technology or CART. Tell us what it does and what trends you see coming.

CART operates on this premise of most businesses, especially legacy businesses that have been around for 20, 30, 50, 100 years, they’re good at what they do. They’re good at getting toothpaste on the shelf or getting gasoline to the stations then into your car. They’re optimized for that and not much else. They’re condemned in a lot of ways to this linear trajectory of, “How can I fix, adjust and change something that I already have?” There’s nothing wrong with that. We have to do that as humans and as business people especially. The risk is the same thing that happened to the taxi industry where somebody comes in from the left-field and totally rethinks, reframes or solves a problem that you thought was cutting the cost of doing business.

What’s happening is if you overlay on that linear growth that we’re on, technology is on this exponential growth curve. There’s this new normal pace of change increasing every single day. The only way to future proof your business is to develop a culture, a group of people that can create and embrace change at a faster rate. CART is designed to do exactly that with a lot of the companies that we work with. We not only can work with them to accelerate the pace at which they make decisions and will do it by moving them through transactions, discussions and processes. They get to decisions about eleven times faster than they do otherwise but we also bring them new technology and tools that step them further into that innovation gap and gives them a chance to get a piece of what might be exponential growth playing with a virtual reality implementation or an autonomous vehicle. Maybe even 3D printed food or things. As they can connect to some of those technologies and they can do it faster, it positions them much better for the future.

“Because you need to be more agile than ever,” is what I’m hearing. With technology changing fast, you have to make faster decisions. How do you de-risk someone’s fears of making the wrong decision by making a fast decision? That’s traditional thinking. Don’t rush into any decisions and yet, you don’t hold on to that model in your head anymore if the technology is changing fast. Am I painting the picture of the gap accurately that you’re solving?

You are. What’s fascinating to me is that humans, you and I, are not built for that kind of change. Our biology, our feeling and even our thinking are tuned towards tomorrow being a lot like now. We feel a lot of anxiousness or anxiety or fear when it comes to presenting us or confronting us with something new, especially if it’s going to potentially, dramatically transform something or it’s going to cost a lot of money. The key with our clients and for everybody is your breakthrough potential is equivalent to the amount that you put on the line. If you put a little bit on the line, there will be a little benefit. If you put a lot on the line, it could be much more beneficial. To your point, you’ve got to balance those two things to say, “We’ve got enough skin in the game to make a small enough decision that if we were to lose it, we don’t lose everything. At the same time, it’s meaningful enough and inspiring enough that we’re going to work towards the potential breakthrough that this thing is going to bring.”

Do you have a story of one of your clients you’ve worked with at CART?

There are many stories. It’s funny because innovation, like entrepreneurship, can be very sexy especially as a consumer innovation, “I want the latest virtual reality goggles, watches and everything else.” It’s easy to do at an individual level, especially when you pay $100 to get one of these cool devices. For a company which is one of the biggest food manufacturers in the world, it’s a little bit different for them because they’ve been around for more than 100 years, at least some of their subsidiaries. They’ve gotten good at what they’ve done. To talk about implementing new technology, selling their products in a different way or getting them to the consumer in a different way. It totally contradicts because what they’ve always done has worked. I was working with them and we were looking at some social media tools, especially TikTok. Have you done a TikTok yet, John?

TSP Hawkins | Breakthrough Strategies

Breakthrough Strategies: Technology that was released five years ago has become normal and expected by the people of today.


I’m familiar with it, but there should be an age limit. There are certain clothes I shouldn’t wear and I should not be on TikTok. Let the kids have that one thing, but I know what it is. It’s going to be the next Instagram.

It’s taking over. Older generations are on it and companies are putting a lot of money into it. We’re having this discussion about this brand stepping into doing a campaign on the platform. They do some other things on social media. When you’re talking about it as possibilities like, “We could do this. We could do that. We could do something else,” it’s exciting and inspiring. There’s a lot of conversation in the room. As soon as you get to that critical point where you say, “Of all those possibilities, let’s pick one. Let’s pick a possibility and let’s start framing up the contract for what that is going to look like.” At that point, you’ve got to put something on the line. In their case, it was a little bit of money. It’s not bad and it’s not wrong. It just becomes a little more serious when you sign on the dotted line to say, “We’re going to commit to doing this.” That’s the only way to realize new possibilities, which is to put yourself on the line.

Would you say that your breakthrough potential is connected to your risk tolerance then? Would that be accurate?


One of the things that you touched on is we’re not built to take on this much constant change. It’s stressful on our bodies and our own brains. The growth and change at an exponential rate that’s never been experienced before can take a real toll on people’s mental health, stamina and physical health. You are someone who is working on your own self-development and growth. You’re teaching yoga. Can you share the importance of that as someone who’s traveling the world speaking and the stamina that’s required for that at any age? You had literally, from my observation, Sterling and why I respect you so much, is you’re walking your talk. You’re modeling for people how to embrace this disruption and constant innovation and still stay physically centered and calm. Any thoughts on that?

It looks better than it feels on a day-to-day basis. It does take a significant amount of effort, will and everything else. To some degree, discomfort is necessary for any innovation. For myself and for people, we can grow from the level of discomfort. I might be worried about a $500 decision but if I get comfortable there, then maybe I can stretch it and make a $5,000 decision a couple of weeks from now. What we’re doing is we’re acclimating to more levels of stress and faster change. Biologically, what’s happening is the cortisol that gets into our blood when we get nervous, anxious, confronted or excited in some shape or form is it starts to go away as you acclimate to these levels of endurance or performance.

What I try to do is continually push that edge of what I can acclimate my body and myself to be comfortable with. Inevitably, it’s going to push me right up against things where I’m uncomfortable. I do these crazy things like skydiving, shark diving and any physical activities where I’ll get confronted. By choosing that discomfort, being able to step into it and grow from it gives me the capacity to not only do all the things that I’m doing now but expand the difference that I can make in the world. I’m not special. It’s the human capacity that everybody’s got the ability to do.

Innovation, like entrepreneurship, can be very sexy. Click To Tweet

This concept of, “As soon as I get into a comfort zone, I’ll be comfortable,” and it is counterintuitive but that is not the case. Your comfort zone is like being in a velvet rut. You get depressed because you’re not stretching and challenging yourself to tolerate something new. Students who think, “As soon as I get out of school, I never have to read another book or learn anything new,” are in for a rude awakening. You’ve posted on Twitter and things that you’ve spoken at the Technology Innovation Gap and spoken with leaders of a supermarket called Hy-Vee.

It’s a great group of people out in Des Moines, Iowa.

Can you share what’s going on in that huge supermarket world? What gaps are there between technology and innovation that was going on at that event?

I can’t share specifically. Supermarkets are one of these legacy businesses in often cases that have gotten good at sourcing products, distributing them out to their stores and creating decent experiences to shop those stores. What they’re confronting is, almost cliché at this point, Amazon and everybody that are selling things online as well as with these different delivery mechanisms whether it’s drone delivery, autonomous vehicles or anything else. Retail, especially when a lot of industries are under this huge pressure, Hy-Vee included reinventing the experience, what the store means, and how to satisfy the consumer’s wants and needs. One of my favorite parts about retail is it’s at the heart of most societies, satisfying our wants and needs, feeding us, getting us clothes and everything else and reveals part of most everything.

Do you remember the time when you could not pump your own gas?

I do remember that.

When they started asking people to do self-service or full service and you have to pay more, people were mortified. They’re like, “What? I’m paying someone to pump my own gas so I don’t have to get smelly gasoline on my hands.” We’re starting to see that in grocery stores where they’re not incentivized. What I find fascinating is you’re not saving any money by bagging your own groceries. Supposedly, it saves you time if you do it faster is the reason to do it but I’m thinking to myself, “There’s no financial incentive like there was with gasoline.” It’s like, “Help us save overhead and bag your own groceries and bring your own bags, by the way, too.” “Why don’t you pick up lettuce while you’re at it?”

TSP Hawkins | Breakthrough Strategies

Breakthrough Strategies: A human’s biology, thinking, and feelings are tuned towards tomorrow being a lot like today. That’s why we get anxiety and fear when there’s something new.


It’s a notoriously low margin business, especially supermarket retail. As they get crunched by more people buying some of their products online, they’re looking for, “Where can I save pennies?” That leaves us bagging our own stuff in a lot of cases.

What do you think about Amazon’s test? There are still a lot of hotels. You go into the hotel, there’s a minibar, you pick up a drink and you go, “I don’t want it.” You put it back and say, “Sorry.” You picked it up and you buy it. They figured out technology-wise to be able to let somebody pick something off a shelf in a grocery store and read the label and say, “I’m not buying that.” It puts it on your phone as a purchase and takes it off when you put it back in. To me, that is revolutionary. That’s a huge leap of, “I can pick touch something and not be committed to buying it.” We are eliminating union paid jobs of thousands of people who’ve been checking people out of grocery stores for decades. Do you think that’s going to take off?

I do. It’s a brand new experience and a good one. By the way, have you been into any of these stores?

I would love to.

Whenever you’re around once, check it out because whenever I’m in there, you go in, you take the products off the shelf and you just walk out. I have this sinking feeling that I’m stealing and it’s uncomfortable.

It is because we’re trained that way, “Where are the handcuffs?” “John, can you come to bail me out? You’re my one phone call.”

It’s still funny because I’m walking out with the product visible in my hand like, “I’m not trying to take something here. I’m doing it by the book.” As soon as you get used to that, a couple of things happen. One is you’re now rooms for shopping in most other places because you can walk into stores and you have to wait in line. It creates this new normal as Uber did. Secondly, it doesn’t feel like you’re buying anything. People tend to buy more things. The same thing happened with credit cards, by the way. As soon as you don’t have to take cash out, you spend a little more money.

The heart of companies is what they stand for, who they are, and what they believe in. Click To Tweet

The same is true with me. I’m like, “Did I order that on Amazon? What in the world is in this box?” I’ve already forgotten I’ve ordered it and you do a little more impulse shopping with Amazon.

What was fascinating about Amazon is how they’ve gone from a company that sold books online to now they’re doing everything. The heart of companies is what they stand for, who they are, and what they believe in. Amazon has got this great mantra that says, “Day one.” Whether you’re on the first day on the job or you’ve been there for 7, 8, 9 years, you walk in like it’s your first day. The genius of it is on your first day of a job, you’re looking for how to do things differently and why they do those things. You’re questioning things, you’re looking for where you can add value and you’re a little bit uncomfortable. They created an entire culture of people that go in every day looking at things new and asking questions like somebody is starting out. It’s given them this fantastic growth in arms into everything.

It sounds like they’ve got a great culture where it’s safe to ask questions and you’re not going to hear, “This is the way we’ve always done it. Therefore, we don’t even discuss it.” That’s the opposite. I’ve talked about this when I give keynotes. It’s focused on “one thing first” and people forget Amazon just sells books. Many startups want to boil the ocean like, “Look at all the things we’re doing.” Imagine if Amazon launched with all the products they have now. People will be completely overwhelmed by buying toilet paper and books. They were known as an inexpensive way to get books. First, you got the social proof before they started expanding. That lesson is true, whether you’re an entrepreneur or not. Be known for one thing first and then you can expand beyond that, but it doesn’t, in any way, shape or form diminish the fact that they still sell books and they’re now selling everything else. As a speaker, anytime at branding, you’re more known for one thing first and then you can speak to other things. The easier it is for people to go, “This is who Sterling helps and what problems he solves for them.”

Apple has done a good job at that as well. Their mantra for a lot of years was, “Think Different.” That’s certainly uncomfortable if you’re the one person in the room that thinks differently than everybody else. They’ve built the whole culture that your point started with one thing and has mushroomed into all sorts of different devices and industries that they’ve disrupted.

You give a lot of different keynotes around innovation thinking and the innovation gap. What I love about your takeaways on the innovation gap is, “You have to first let go of everything you think you already know,” which is so Zen. I love that.

It is difficult to do.

It’s because you’re like, “What?” and that’s our entire identity into our knowledge. Only when we let go of what we think we know can we discover what’s possible. You have to take the audience on a journey because they’re already resisting letting go of what they know before you can start getting them to imagine new ways of doing things.

TSP Hawkins | Breakthrough Strategies

Breakthrough Strategies: Retail is under a lot of pressure to reinvent the experience of what the store means and how to satisfy a consumer’s wants and needs.


It is a blast every time. Speaking is one of my favorite things in the world to do and to step in front of a group of people that more often than not tends to be cynical about whatever it is that they’re doing and rightly so, the world is a hard place. To break through that force field to discover some new things is a blast.

How can someone reach out to you? If someone wants to hire you as a speaker, find out about CART or even have you come in and do a workshop, what would be the next step for them to explore? is the best place. CART’s website is I’m searchable on most social media except TikTok. I’m not there yet.

Any last thoughts, a quote or a book you want to leave us with?

It was great spending some time with you, John. I know we go back several years now but then having this conversation, I appreciate being on your podcast, who you are and the difference you’re making out there in the world.

Thanks a lot. That’s Sterling Hawkins, everybody, breakthrough innovation. If you want to watch somebody walk their talk, follow him on social media and explore having him come and speak at your next event.

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About Sterling Hawkins

TSP Hawkins | Breakthrough StrategiesSterling Hawkins is out to break the status quo to create what’s actually possible for humanity in our time. He has spent his career igniting new views and inspiring people to act on them.

His journey has been non-traditional right from the beginning. Sterling grew up a fifth-generation retailer, having to master the intersection of human behavior and technology under extreme competition. In 2004, Sterling co-founded, launched and sold his first technology company, Convena, where he developed innovative approaches to beat competition, handle high-growth and achieve performance no matter the obstacles.

He went on to be involved with the launch, growth or investment in over 50 companies. Today, Sterling reviews over 1,000 new technology companies every year further refining the keys to realizing breakthrough innovation and giving back that experience as a mentor to leading entrepreneurs working through exponential growth. He is the co-founder of CART, a platform to drive adoption of emerging technologies at fortune 500 companies. And he speaks and runs workshops around the world for clients such as Samsung, Criteo, Synchrony Financial and the United Nations.

Sterling is an internationally-recognized thought leader and top-rated keynote speaker on innovation, transformational leadership and exponential growth.

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