Future Proofing You With Jay Samit

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TSP Samit | Reinventing StrategiesEpisode Summary:

If your old business ways are not working anymore, it doesn’t mean you need to do a full reset just to try once more. Sometimes, all you need is to start reinventing strategies. When you give a chance to the things you don’t give a lot of love into, interesting outcomes may surprise you. John Livesay sits down with Jay Samit once again, this time to talk about his book Future Proofing You. Together, they talk about how your fears can be leveraged to discover neglected opportunities and how tried and tested tools can be rehashed to achieve refreshing and far better results.

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Future Proofing You With Jay Samit

Our guest on The Successful Pitch is Future Proofing You author Jay Samit. Jay has been on the show before. He talks about the Twelve Truths he’s written about in his book and how he busts through a lot of myths. One is that the world operates as a zero-sum game that if I win, you lose. He said, “That’s not the truth. What is true is that you’re only one click away from having incredible success.” He defines success as going way beyond making money but realizing what your purpose is. When you’re willing to work harder than most people, he says, you have a life that’s better than most people. We talk about the different kinds of fear. The fear of humiliation, failure, rejection, and how to overcome those fears. Enjoy the episode.

Jay, welcome back to the show.

Thanks for having me.

Why don’t you fill us in on what you saw and the success of Disrupt You! Let’s take a minute and brag about that huge success. How many languages has it been translated to and the impact that you saw?

I highly recommend it to anybody who feels that they have a book in them to write it. You’ve learned this as well because I’ve run companies with 300,000 employees and offices all over the world. When you’re at the top of a big company, all that you get is problems, fires, and hate mail. When you write a book that changes people’s lives, you get literally love letters from around the world. People who’ve turned their lives around or people that have stopped a suicide people. It’s an amazing transformation. The response was beyond anything I ever imagined. I’ve heard from readers in 140 countries. With COVID disrupting the world, it’s become a hit again and it’s coming out in languages like Icelandic, Urdu, Italian, Polish, and on and on.

Each time when it launches in the country, I suddenly hear from people whose lives are transformed. That being said, it turns out I have thin skin. Once in a while, I get an email from somebody, usually a millennial that said, “This is all motivational, but I could never do this.” That drove me nuts because my whole reason for writing a book isn’t to make any money, I don’t need it. The purpose is to take what I’ve learned and what I feel you’re not learning in school, and you’re not learning in an MBA program of how to get success and it’s easy.

I grew up in a regular middle-class, working-class family and dozens of friends become billionaires and change the world. We’re not smarter, we’re not better looking, we didn’t have connections, we didn’t have capital, but we saw the world differently and that can be taught. I decided to put my reputation on the line and I took a young man who was an immigrant, grew up on welfare, had no connections, no capital, and no entrepreneurs in their family. I decided to take the knowledge that I have and synthesize it down to twelve truths that if you embrace these, you will be successful.

TSP Samit | Reinventing Strategies

Future Proofing You: Twelve Truths for Creating Opportunity, Maximizing Wealth, and Controlling your Destiny in an Uncertain World

His name is Vin Clancy and I mentored him one day a week for a year. I gave him no money. I introduced him to no one and I didn’t tell him what business to start. By the end of the first month, he made $70,000 and he could have flown to Europe without a plane. He didn’t believe it was possible. I didn’t know if he could keep up that level of commitment. No one says it’s easy but if you’re willing to work one year of your life harder than most people will, you can live the rest of your life better than most people will. He made that sacrifice and spoiler alert for the book, he hit it in less than a year, which was amazing to me. People wanted it to step by step. I went with Wiley as a publisher this time because they’re known more for technical types of books but it’s not a technical book. It’s some basic tricks. I’ll give you an obvious one and you know them. You solved it.

I’ve seen them in action before the transformation. I’ve heard his own personal story. You certainly picked a rags to riches storytelling genre there to come to life.

I’m also a fan of My Fair Lady and the Cockney accent from England so he’s my Pygmalion. Let’s start with a basic premise that people are taught in school that’s wrong. In school, you’re taught to buy an apple for $1 and you sell it for $2. You make $1 but the world is a zero-sum game. The only way for me to make money is to take it from you. When in fact, most of the millionaires and many of the billionaires never made a profit. They didn’t take money. If I start a new company, and I sell you 10% for $1,000, we now have a $10,000 company. I made $9,000 out of thin air. Jeff Bezos lost money for a decade and became the wealthiest man on the planet.

Every 48 hours, there’s the self-made billionaire. What are these people doing differently? Why is it easy when we’re all one click away? I have to be right for a nanosecond. To make money or to change the world and success isn’t about making money. I believe that the purpose of life is to live a life of purpose. What is your purpose and what do you want to achieve? One of the things that I’ve definitely seen since traveling the world for the past few years on endless book tours is that capitalism has to change and is changing to sustainable capitalism. Things that are both good for the bottom line and good for the planet.

This isn’t some hippie-dippy left-wing philosophy. Walmart, one of the biggest retailers in the world realized that their second biggest cost after employees was electricity so now they’re the biggest solar user. Why? It’s because it’s good for the bottom line and it’s good for the planet. There are many opportunities now to leverage the networks and the technology to do things in ways that don’t end life on this planet but help us sustain life. If you look at all these changes, and you realize with each of these changes, what they are new opportunities. There are many new ways to make money that didn’t exist.

That’s what I love about this book, Future Proofing You. It’s almost a continuation of Disrupt You! which you did brilliantly in laying out the premise that you need to disrupt yourself before it happens to you. Many people are afraid of being disrupted in terms of their job ending or getting fired and now the concept of the pandemic, having many people and industries even going away. The need to future proof ourselves is even more valuable than ever so we’re not living in fear. This concept of, “I’m doing my job. It’s a means to an end. I’m not happy, and it could go away at any moment.” That’s not a definition of anybody’s success, is it?

Yeah. To work at a job that you hate, wake up one day and you didn’t trade a day or a week or a year, you traded the only life you’ll ever have. This makes no sense to me. I was a vice-chairman of a company with 300,000 employees and partners retiring at 60. It’s a consulting firm. Since they run their own retirement plans and all that, they know the life expectancy. Here are the wealthiest and most successful leaders in the world. Their average life ends at 66.

The purpose of life is to live a life of purpose. Click To Tweet

Isn’t that shocking?

Your average NFL players’ life ends at 55. We’re not making choices that make sense and for those that didn’t believe the disruption would happen to them, 2020 proved my premise. Whether by choice or circumstance, you will be disrupted. That’s one of the things when we’re talking about sustainable capitalism. Whether you believe it or not, governments are going to start coming up with regulations that are going to force the industry to do things for survival.

Do you wait until your business gets told to do something and you’re out of business or do you get ahead of the curve? Do you look at the opportunities that are happening with this change? You mentioned this as a second course. In Future Proofing You, I talked about if this was a college course, the prerequisite would have been to take Disrupt You! 101. This is a continuation. This fills in, for me, the gaps of what people said that I didn’t cover and they didn’t understand how capital is created. Fear is one of the truths that we talked about.

Let’s talk a little about that.

Fear is the greatest thing.

You have a quote that I have given you credit for multiple times over the years, which is, “Fear is feedback. We keep going until we get a zombie idea so great that it won’t die.” Every time I say it and say you said it, everyone laughs and they have this insight of, “It’s true.” If you have anything else to say around fear, I’m all ears and I know that our readers are too.

We have to remember that we’re evolved lizards. We still have our lizard reflexes, fight or flight. Those basic reflexes allow our body to do stuff with us not even thinking about it. We have hundreds of thousands of years since we’ve been mammals dealing with this stuff. Why I say that is, we’re not quite suddenly changing, because we have a phone and a computer. Fear is why you’re here. If your great-great-great-grandfather in the cave wasn’t afraid of the saber-toothed tiger, you wouldn’t be here. Fear kept people alive.

TSP Samit | Reinventing Strategies

Disrupt You!: Master Personal Transformation, Seize Opportunity, and Thrive in the Era of Endless Innovation

What you’re afraid of is what you have to focus on. People are afraid of failing. People have a fear of being made fun of, fear of rejection, and all these things. Those are legitimate fears. I’m not going to mock you but isn’t the greater fear of wasting your life? Isn’t the greater fear of never having happiness? If you go to any of your grandparents, if you go to a senior citizen, go to an old age home, and ask people their regrets, it’s not something that they tried and failed, it’s something that they failed to try. That’s the first half. That’s your fear.

If you change what you’re afraid of, you can overcome these insignificant fears. I learned this in college, if I asked that girl out, and she turned me down, I’m being rejected, and that’s horrible. If I ask out 100 girls, someone’s going to say yes. I’m in better shape than that I’ve been afraid to ask at any. Businesses are the same way. Here’s the part about fear that nobody else writes or talks about. That person across the desk across the table that you’re trying to sell, you’re trying to get to hire you and you’re trying to impress, they have fears too. If you can understand what fear motivates them, you can better attune what you’re saying. I’ll give a great example because we came off of the election.

It’s a strange scene two elections ago, not a single presidential candidate was spending any money on social media. I wrote this white paper saying social media will pick the next president of the United States and this is in 2010. It was a little early but I looked at the campaign. This was when Obama, McCain, Mitt Romney, and everybody was running. They’re going to spend $2 billion and I happen to have a digital ad agency at the time that I was building up and we took it from nothing to selling it for $100 million in eighteen months.

The way that I worked fear was I looked at these campaign managers and they weren’t spending any money on social. They were older and they didn’t understand it. They weren’t on Facebook. These were the days so I went and let them know that I could only meet with them on certain days because I was going to the other cities with the other campaign managers. I explained why this works, or whatever and they didn’t believe me.

They didn’t understand it but what they did know is if another candidate was using social media and they won, they would never get hired to be campaign manager again. Their career would be over. By the time I did, my circle of the four presidential candidates all four became clients and all four said, “If I hire, you can’t work for anybody else.” I said, “You don’t do that with ABC, NBC, or anywhere else that you advertise.” That’s how we got presidential elections to buy digital ads. Fear.

The fear of missing out.

Fear of getting fired. If you’re dealing with a big corporation, there’s only one thing and I’ve been CEO of NASDAQ companies. I’ve been through the whole thing. There’s only one thing that anybody thinks about and it isn’t shareholders and it isn’t profits. It’s keeping their job. They fought tooth and nail to get to that C-Suite. The life expectancy of a CMO or CEO is about the same as cheese. I’m not talking about some rare Swiss cheese. I’m talking about the kind that stinks after a couple of days. On average, a CEO lasts less than four years in this country. Self-preservation. How is your pitch of you coming in trying to sell them into business? What impact does that have on their self-preservation? Frame it in that and you’ve won.

If you're not changing your skillset, you're becoming obsolete. Click To Tweet

What’s in it for them?

I know that you pontificate and I mean that in a positive sense, about having to make that emotional connection in that story from the range of emotions that you can play with. Machiavelli taught us 300 years ago that it’s great to be loved but you can’t force somebody to love you, you can make somebody fear you. I don’t mean the fear in the mafia, “If you don’t buy this from me, I’m going to burn down your thing.” It’s the fear of what if your competition uses us and your boss finds out that you turned down this opportunity?

I talked about that. I said, “The new way of doing sales is whoever tells the best story is the one that gets the yes. If your competitors are telling a better story and you don’t even tell a story, you can imagine why you’re going to be losing market share, which goes into and that’s what they’re evaluated on.”

In Future Proofing, I broke down the three fears that drive people in business and how to leverage those for success. The next thing that was new that was an oversight in Disrupt You! that’s in Future Proofing You is there is a myth of the self-made man or woman that somehow you did it on your own. I was part of this myth when I ran music labels with our rock star on the stage alone with that guitar. What you don’t see are the makeup artists, the hairdresser, the production manager, the nine producers on the record, the promotion, the tour roadies, and everybody. It takes a ton of people. It’s the same way, you’re not going to make it to the top on your own.

Don’t fly solo and for each stage of your career, you need different mentors but no one ever taught you how to get those mentors. How do you get millionaires and billionaires to help you and work for you for free? None of us would get here without standing on the shoulders of others. Much of what I did, I did being naive and it worked and now I understand why it works so I teach it. When I was nobody sitting alone in my little five-man company, I wrote to the richest man in the world, Bill Gates. Would he introduce me to the biggest guy in the music industry because I had an idea that would make people playing video games on computers more fun and I have the technology of how to do it?

When the richest man in the world contacts a billionaire, they take the meeting. It goes back to asking girls out. If Bill Gates had not responded, I wouldn’t have been devastated. The fact that Bill Gates did that for me and I’d never met him at that time. Talk about being elated. When you reach for the stars, you may not make it to Jupiter, but you can make it to the moon. You’ll make it much farther than you ever imagined and this is what I did with Vin.

I’m seeing that it’s the same feeling you had from Bill Gates. You gave him when he made his first $70,000 in the first month. It’s a fantastic legacy.

TSP Samit | Reinventing Strategies

Reinventing Strategies: Work at a job that you hate and you traded the only life you’ll ever have.


I showed him to reach beyond what he could understand. He thought he knew all about social media and he was trying to do online marketing for people. He was going after people who couldn’t pay him anything because that’s all he knew was his craft and everybody else was doing the same thing. I go, “How do you differentiate? How do you show that you were the best in the world at one thing? If you’re not the best in the world at something, no one needs to hire you.” It turns out, I hate competition because I know there’s always somebody better, brighter, nicer looking, better financed, and knows more people. If you go into an area that nobody else has gone, if you’re the first one doing it, if you’re the only one doing something, by definition, you’re the best in the world. How do you differentiate what you’re doing? If you can’t articulate that differentiation, how do you expect somebody else to recommend you, want you, or use you?

Hence the need to have a great elevator pitch so people can understand what you do in a way that allows them to share that story.

I’ve gone into more fields before anybody knew what you were talking about. I’ll give you a great example. Zoom is now worth more than Exxon. Years ago, I was President of a company called ooVoo. It’s the technology as Zoom. They’re the first ones to do multi people used by tons of people but at that stage, the only people who got to use it were teenagers. It had 100 million teenagers using it around the world. It was the number one app with teens prior to Facebook and yet businesses couldn’t understand it and didn’t see a need for it.

Doctors wanted you to come into their office even if it was for something that didn’t involve touching your body. What the pandemic did, it wasn’t changing behavior. It accelerated trends that were already happening. Having a remote workforce is one of those trends that I talked about in Future Proofing You. Since the beginning of time, if you open a business 100 years ago, you don’t get to hire the best people. You get to hire the best people within 5 miles, the best people in your culture, or the best people in your nation and now you can hire the best people in the world. It turns out people who work from home are more productive than people that go to an office.

It’s counter-intuitive than what management thinks.

They’re happier, they stay longer and there’s less turnover. All this had been in studies for years but it wasn’t until the pandemic forced people to change. That’s why I talk about disrupting yourself. If you wait until you’re forced to do something, everybody else is doing it then. To watch a surfer, they don’t wait for the wave to break. They paddle out to where there are no waves so they’re in the perfect position for that one opportunity.

When I was working with Redfin, they were having their customer service onboarding people work part-time from home and part-time in the office. When the pandemic hit and the whole thing about, how do we set people up to work from home for most companies who would never let them do it, they were a little bit ahead of their competitors because those people already had a home office setup.

When you reach for the stars, you may not make it to Jupiter, but you can make it to the moon. Click To Tweet

They put the tools in place and they’re ready.

You talk about being early sometimes doesn’t mean you get to be the market leader when the change does come. At that moment in time, you don’t have competition. If we look back at Beta to VHS. Beta was considered a superior quality and yet VHS back in the days when people were recording stuff took off. I’ve read something that I wanted to ask you about with Skype. At one point, Skype had a big hole in the business world. Suddenly, no one was using Skype for video calls. It was all Zoom. What do you think Zoom did right or Skype did wrong that caused that to happen?

When we went after Skype, long before Zoom, we realized that there were more forms of communication than one-to-one. Skype was revolutionary. Turns out, one-to-one communication, ICQ existed back in the AOL days. Nobody had the bandwidth to do video, but the process was the same. Looking at those unmet needs and unmet audiences of where it makes sense. My favorite example was texting. It’s going to sound weird to people that didn’t grow up pre this era that were never used on phones. You could have always done it. Phones were for talking. What happened was your talking minutes were more expensive, your texting was cheaper, and people still didn’t switch. In the hip hop club culture, you couldn’t hear so people were texting each other.

What a great story of origin.

From that approach, I was involved with Nokia back when they were 45% of the global market share of phones. They were one of the first to have a camera on a phone. They thought it was a killer feature. Nobody would use them. Nobody understood. Why would I need a camera on a phone? Nokia hired good-looking models pretending to be a couple in high tourist areas like Times Square, New York, whatever to walk up to a stranger and go, “Would you take a picture of us,” and hand them a phone. It never occurred to people. What I’m getting to is we all calcify. We can make ten million decisions a day so we develop habits.

When I was taking my youngest son to his first apartment, we’re driving around, “There’s a perfect one. There’s a sign. Write down that number.” He takes his phone and takes a picture. That would have never occurred to me. I have a different habit. How can you use the tools that other people have existed to solve a problem with data and focus on? The biggest fortunes aren’t made by the inventors of something new, they are made by those that solve a problem. All success is solving problems.

What you’re saying here is look for ways to use existing tools in a new way.

TSP Samit | Reinventing Strategies

Reinventing Strategies: There is a myth of the self-made man or woman that somehow you did it on your own.


A new market. New use and you own that market. That’s exactly what Vin did that I talked about in the book. There was nothing that he wasn’t doing before. He was charging $100 for and now he could get a client paying him $35,000 a month to do the same thing that you used to for $100. In the book, I talk about my favorite example, and I’ll bore everybody who doesn’t care about magic. Harry Houdini, the name synonymous with magic, one of the most famous magicians of all time used to work in these little things called dine shows, where you come in and see a bunch of shows. He’d do ten shows a day and he was starving to death. He was making pennies. A guy saw him and thought he had a great talent. He took him out, repackaged that same act, and took it to Europe where he made some money. When he came back to the US, it was like, “Here was the star of Europe who would perform before all the kings and queens in Europe. I want to see that.”

It’s easy to make these changes. There’s nothing in either of my books that you’re going to go, “That’s rocket science. I need a calculator.” You’re going to say, “That’s common sense. Why didn’t I ever do it? Why didn’t I think of that?” One of my favorite stories was about a young man who watched Mad Men on TV and wanted to work in advertising. He got a job at one of the big agencies in New York and used to work in New York. That’s an amazing accomplishment until you show up and you’re an acute doing mindless moving of numbers and charts for execs and there’s nothing creative about it probably for fifteen years.

He was googling around and he realized that the big creative directors of the big Omnicom of the world, the WPBs, none of them want their names as keywords. It was obvious to him that every famous person has to google themselves to say something untrue, bad, or whatever. For $9, the cost of that Frappuccino somebody slurping on reading this, he bought the names of the top five creative directors in the world and said, “I’d like to work for you. Click here to see my portfolio.” Three of them offered him jobs and accelerated his career by hundreds of thousands of dollars a year in fifteen years of time for $9.

What a great story. Before I let you go, I was intrigued and I love an open-loop more than anybody else, when I’m reading about your takeaways from Future Proofing You, you talk about ways to get a piece of the trillion-dollar opportunity that’s bigger than mobile. Can you give us a hint of what that might be to entice people to want to get the book?

That’s one of the truths in this book that I hit on hard. It is hard for people to imagine a world without cell phones. We’re all addicted to them. We look at them hundreds of times a day and we spend hours a day with them. In the next few years, that phone will no longer be coming out of your pocket. You’ll be wearing a heads-up display. Augmented Reality is a fact. My consulting clients are Facebook, Microsoft, and Google, I know what’s coming. The best way to predict the future is by hanging out with people that are coding it. I know I’m right, not because I have a crystal ball I’ve seen and I know their schedules when they’re coming out. Here’s the proof for people that don’t believe or like, “I’m never going to wear crazy glasses.”

In 2020, in the United States, 50 million pairs of glasses were sold that cost more than $150 a pair that came with one app, Hocus. Another 30 million were sold that came with a different app called SAN. If you need to read or you don’t want to be blinded out in the sun, we buy glasses. When the phone came out, when the iPhone came out, what were the top ten bestselling apps the first year? I’ll tell you two of them. The Fart app that makes sounds up farts and a game with cats. There was no OpenTable, there was no go through your ten most useful apps, but each of those became billion-dollar businesses.

Somebody did the hard part and the glasses are all coming out. He saw things that you couldn’t do with the phone. What is that killer app? Here are the obvious ones and the thing that’s hard for people to understand. Google has the greatest business model and makes them a boatload of money. I don’t need to convince anybody that but if you’re no longer looking at your phone or your desktop computer for searching for stuff, they go out of business if they don’t own this.

All success is solving problems. Click To Tweet

Apple no longer caring about showing people the new iPhone doesn’t come out of your pocket. Apple goes out of business if they don’t sell this. Facebook, if you’re not using your phone or computer to get the message, this is an existential threat. This is a trillion-dollar opportunity. The big guys, with the deepest pockets, are solely focused on that piece of hardware and the OS around it. They’re not thinking of the millions of millions of apps. They want to get market share that they will use OPM, my favorite money, Other People’s Money, to make your app successful or advertise it because it makes people use their device.

One proof. I’m the old guy on the wrong side of 50 with a gray beard. There was a time when no one ever swiped, now, I can’t imagine. No one knew how to swipe. We know how to use a mouse. We didn’t know how to swipe. Apple, knowing that they were coming out with a tablet, the iPad, wanted to find a game that uses swiping. There weren’t any. They went to any little company that wasn’t successful because the big guys were busy making hit games. Make a game that swipes and we’ll put it in our TV commercial.

There was a company that had 30 failed games and they were on their next one in Northern Europe in Scandinavia that no one had ever heard of. They made a little game of the pandemic of that year. The pandemic that year was because there was swine flu. All of Asia had to kill every single bird because they were catching it. Remember this? H1N1. The birds were angry about the pigs causing them to die. The most bizarre game you could ever say would be it.

Apple spent $100 million in TV commercials for the iPad and everybody saw Angry Birds in that commercial. When you flew business class or coach, it didn’t matter what for the next three years, all you saw anybody doing was playing Angry Birds and buying Angry Birds lunch boxes, birthday toys, blankets, sheets, and $12 billion worth of merchandise. All because somebody else advertised a solution to a problem they had. How much of that ownership did Apple take? It’s zero. There are people that will give you millions. I have had companies give me tens of millions of dollars.

I remember Sony.

Coke or McDonald’s. They’re the biggest brands in the world. They didn’t want any equity. They don’t want to get paid back. They didn’t tell me how to do it because I could solve a problem that they had. Whatever business you’re trying to launch, there’s somebody else that wants to reach that same audience that isn’t a competitor. You can make that person that doesn’t have an idea look smart.

Jay, I can’t thank you enough for coming back on and sharing your wisdom. Thank you for writing Future Proofing You. I’ve got my copy. I can’t wait to share it with other people because not only are you helping us, but it makes an ideal gift. If you know people that are struggling and wondering why can’t I figure out how to get my life going, this is the roadmap.

TSP Samit | Reinventing Strategies

Reinventing Strategies: If you’re the first and only one doing it, by definition, you’re the best in the world.


This is why I write. Nobody’s writing a book to make money. This isn’t Harry Potter. This is taking years of my knowledge and the knowledge of everybody that was kind enough to help me along the way and synthesizing it in a way that is actionable. That’s the keyword. Everybody needs to commit to lifelong learning. The world is changing. If you’re not changing your skillset, you’re becoming obsolete. You’re going to be roadkill in the future.

We know that we’re not going to get back to a world that doesn’t change or suddenly has all this certainty and stability. It’s up to us to control our own destiny by realizing these twelve truths you’ve written about.

The world is changing faster than ever before. That’s what’s causing so much angst in people. That’s why there’s a generation that is not going to live older than their parents. I love democracy. Democracy only exists with the middle class and the middle class only exists with entrepreneurs creating jobs. Governments don’t create jobs. I don’t care what party you are in. When you solve a new problem, if you’re reading my words now and you have problems in your life, congratulations, you’re halfway there. That’s all that you’re doing and I’ll leave you with one acronym that’s in the book, MOVE. It starts with a Mindset, an Obstacle, finding a Void in the market, and Executing. All you have to do is move.

I love it. It’s a great metaphor on so many levels because we know without action, nothing happens. We need to keep moving our bodies. Why in the world do we think we need to not keep moving our brains to keep learning? Jay, thank you so much. The book again is Future Proofing You. I can’t thank you enough for inspiring all of us to future proof ourselves.

Thank you so much for the time.

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