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17 Questions: 1-4

So the first is, what if I did the opposite for 48 hours? Okay. What if I did the opposite for 48 hours? This first became very important for me in 2000. I had my first job out of college. And I was the lowest paid person in the company. Then they hired one other person who became the lowest paid, which we found out because they accidentally sent out an Excel spreadsheet to a friend of mine, with his paid time off. And they deleted everyone in that tab but then the next tab had everyone's compensation. Oops. And I was a technical sales guy. I was selling mass data storage in San Jose. And I was not doing very well, I was having a really tough time, I was smiling and dialing, cold calling, cold emailing, it was just tough, if anyone here has ever had that experience. And I realized at one point that all of the other sales guys, all of the sales guys myself included, were making phone calls between 9 and 5, right, business hours. And I thought what if I did, nothing seems to be working, ...

what if I just did the opposite for 24 or 48 hours? And what that meant was, alright, let me try doing my calls before nine, so let's just say, hypothetically, seven to 8:30? And then after business hours from six to 7:30. And by doing that, I said, okay, I'll do it on a Thursday, Friday, they're kinda slow anyway, it's not gonna do any damage that I can't reverse. And I tried it and I ended up getting ahold of almost all of the CEOs and CTOs I needed to get ahold of. Why? Because all of the gatekeepers were gone. So the layers that would have been protecting them otherwise were gone. And I ended up then applying that, what if I did the opposite for 48 hours all over the place? What if I sounded like an engineer instead of a sales guy? So I actually spent more times studying the science and the engineering as opposed to reading my 75th book on spin selling or whatever it would be. What if I only ask questions instead of assuming I knew what solution they needed for X, Y, and Z environment? And long story short, at the end of my tenure at this company, which ended because it imploded like every other start up at the time, I was able to outsell the entire Los Angeles office of EMC by myself. EMC is a big, big company. And it was attributed to, I attributed it to, that first question: what if I did the opposite for 48 hours? So think about, we're gonna come back to how you can de-risk that for yourself. But what if I did the opposite for 48 hours? And like, right now for myself I'm asking that. For instance, because over the last I would say week, I've been a little hyper-caffeinated. A little over-caffeinated. I had some friends send me a big box of smart drugs. And I was like, oh, thank you, but damn you, why did you send me all of these pills and powders? Now I have to taste test everything, so I've been going a little overboard with that. Don't do drugs, kids. So what if I did the opposite? What if I had tea? What if I actually had, like, chamomile tea and did multiple sessions of meditation to de-hype myself. And that's what I've been doing today, will be doing tomorrow, as well. So, alright, I still apply all these questions. Alright, the next one is, what do I spend a silly amount of money on, how might I scratch my own itch? Alright. So what do you spend an absurd amount of money on, just as a percentage of your disposable income, or your total income? And this was relevant to me first, I've done this many, many times since. How can you scratch your own itch? These are related but not mutually dependent. Came about, in 2001, when I was looking to start my own company, just before the demise of the one that I was working for, and I went through my credit card statements, so instead of going to get an MBA, doing a bunch of sophisticated market analysis and so on and so forth, how did I decide where to focus for my next business? Well, I went through my credit card statements and I looked at where I spent the most money, and at $40,000 pretax in the Bay area, especially, I was spending probably $500 a month on sports nutrition. That is outrageous. I mean, that is an outrageous amount of money. And I had dozens of friends who were doing the same thing. So I was not an isolated case. And it was something I knew a lot about. What are the advantages here in scratching your own itch? You know what advertising has worked on you. You know where you buy it already and who sells it. You might even know who the distributors and channels are. And all of that translates into having a huge advantage if you then decide to create a product in a category that you spend money on, that you currently don't have a solution for. Does that makes sense? So you find a category. This is where I spend a ton of money. What is a pain in my ass in this category? What do I wanna spend money on? Okay. And then you go make that. Or you can test it and then make it. You can do some type of dry testing as well. And this is how Twitter started, this is how many of the startups and companies that are revered and worshiped in this part of the world, and in the world in general, started. Scratching your own itch, alright? So that would be the next. And then we have, alright. What would I do/have/be, if I had, say, a million, ten million, and so on? What's your TMI, that's not too much information. TMI stands for target monthly income, alright. And these questions, I should point out, are not unique to me. Variations of these questions, I've observed being used by the vast majority of the folks that I've interviewed and had the chance to interact with over the last few years. They have questions like these that they use. So in presenting these, the goal isn't to say you have to use all of them. It's to say you should pick a handful and focus on really reflecting on them and writing them out, your thoughts on them. So what if you had 10 million, a hundred million, whatever the number, the magic number is for you that would mean you don't have to think about money any more. What would you want to do, be, and have? And you write this down, and then what is your target monthly income to satisfy this? That was important to me in 2004. My business was doing extremely well and I was as miserable, probably more miserable, than I'd ever been before. Okay. Had a girlfriend leave me, thought I was gonna propose to. I was working all hours of the day. And I did this exercise because I was miserable and I either wanted to extricate myself from my business or shut it down. Those were the choices. And when you run the math on this, so let's take your dream retirement as such. So if you had all this money and you could do, be, or have anything, what would they be? And get really specific. Once you do that, then cost it out. So what do I mean by that? On a monthly basis, what would you have to spend to do all of those things, right? Ski chalet in Colorado, fine. You want some fancy car, my fantasy at the time was an Aston Martin DB9, because of James Bond. So it's like okay. And you've cost it out. The point being, many of us believe that we have to have millions and millions of dollars to achieve this dream lifestyle. But we make two mistakes. Number one, we never pause to very clearly define what that would be if someone just wrote us a check and said you're done, now what? So you define it very clearly. Then you cost it out. And what I realized is, when I looked at the monthly cost or the total cost of a lot of these things, it averaged out to less than I think it was, $7,000 a month. So why wait? At that point, you then understand the financial realities of it, and you begin to feel a bit more enabled to go into a planning phase where you can start to test some of these things. So if you think that these sort of slave-save-retire, I'm gonna work for 20, 30 years and then I'm gonna sail around the world for the rest of my life and be as happy as clam, like, okay, maybe we should set aside a long weekend where you go down to, like, Key West or somewhere and you get on a boat for three days. And see how that goes for you. (laughter) Instead of, like, predicating decades of suffering on doing that for the rest of your life after that. I'm just saying, you know, I'm not trying to judge. But maybe you wanna do that. And I started to do this, and I found, in fact, that many of the things that I wanted to do and have and so on, that I was pining after for some end of the rainbow experience later, gave me next to nothing. And on the flip side, in the process of testing found things that were much more life-affirming and enjoyable that cost almost nothing, okay. So that's one. Now the next that we have is, what's the worst thing that could happen and could I get back here? This is arguably the most important concept that I'm gonna talk about. Is this interesting, remotely? Yes. Okay, alright. Thank you. So, what's the worst thing that could happen? Because let's say you spec out your total monthly income. All these things you want to potentially experiment with. But, I have a job. Or even harder still, I have a company. I'm the boss. I can't just wind this thing down, or do X, Y, or Z. This exercise that I do all the time, I do it probably once a quarter. if I'm feeling overwhelmed or agitated I do it even more often, probably once a month. Called fear setting. And fear setting, if you search that and my name, you can find all sorts of details on it. It's also written about in Tools of Titans, entire chapter on it. But the basic gist is this. When I decided, for instance, that I wanted to take a trip around the world, to either automate my business or shut it down. Those were the options. And I did the TMI, I did all that stuff. And then I proceeded to postpone doing it for about six months. Dancing around with all these vague notions of what could go wrong. And there's the big issue right there. The vague aspect of these fears. So fear setting, goal setting is great. It's fine. But if you're putting on the gas towards goals and you have the emergency brake on, which is the fear side of things, you're just not gonna go anywhere. You're not gonna get to those goals. You need to remove that emergency brake. And the way that I do that. You take a piece of paper, alright. Just take a piece of paper like this. And you'd put at the very top whatever it is that you're considering doing. Sell, approaching someone, asking someone out on a date. Ending a relationship, quitting a job, whatever it might be. Taking an eight-week trip around the world. And trying to not check email for that period of time. Whatever it is. And then you have three columns. You have two lines, like so, dividing the page into three columns. In the first column, you ask: what are the worst things that could happen? And you write down, get really specific, the worst things that could happen. So for me it was, like, well, I'd probably miss a letter from the IRS and then my business would get shut down and then I'd be in Ireland, say hi to a stray dog, it would bite me on the face, and like... You know, I really get imaginative. Be really, really specific. And you make that list. In the second column, what are the things I can do to minimize the likelihood of each of those happening? Right, so with, say, the IRS issue. Well, maybe, okay, I could potentially use something like Earth Class Mail. So they'll scan my mail and email scans of my mail. Okay. That would certainly lessen the likelihood of something catastrophic happening. I could put, say, my blah-blah-blah on prepayment. Right, I could prepay some of my federal taxes. Whatever it might be, there are ways to decrease the likelihood of those things happening. Alright, next column is: if this thing happened, that is causing me so much anxiety, what could I do to get back to where I am now? How could I repair the damage? Right? So let's say you start with, you're considering starting your own company. Okay. Worst thing that could happen. Well, I don't make enough and have to go back to my job. How could I minimize the fear associated with that? Maybe you start moonlighting, okay? So don't quit your job. Keep your job and start working on that business in the evenings and on the weekends. And then, in terms of how you can get back to where you are now. Let's say you do that, you get the company up to a point where your business is making you, I'll make up a number... $5,000 a month. That's a decent chunk of change. And maybe you're making $75k a year or whatever it might be. You quit your job. And then the company goes south. What do you do? Alright, well. To cover your costs, right, to get back to where you are now or just to repair the damage, what could you do? You could move in with friends, you could move in with your family to cut down on rent costs. You could become a bartender, you could be a Task rabbit, you could be an Uber driver. All of these things. And in defining all of those and getting very, very specific, you de-risk it for yourself. So I use risk in a very particular way. I was worried I wasn't going to be able to talk 30 minutes, we'll see how it goes, if I can get through five questions. Alright. But I front loaded the most important, I think, or the ones that are most critical. De-risking. So risk to me, when people say it's risky, or people might tell you, oh no, you can't do that, it's too high risk. Risk, for me, is a very, very specific thing. It is the likelihood of an irreversible negative outcome. Okay. And irreversible is super, super key right there. Because when you are saying, alright, I want to do X. And if it works, I'm looking at, on a scale of one to 10, a nine or 10 life changing impact for me. Permanent impact. Okay. And then you do this fear setting exercise, and you realize, wait a second, okay. If I do it, nine or 10 magnitude, life changing, permanent. And if it goes sideways I'm looking at a two to three temporary negative. Well you start to do these types of exercises and you're like, that means that, I have a six-sided die, every time I roll it, one to five, the universe gives me 10 dollars. And if it's a six, I pay the universe 10 dollars. Okay. I'll take that bet every day of the week. And you realize that, in fact, it's not risky at all. It is a very, very prudent, in some ways, decision. And you have to weigh the cost of inaction, not just the cost of action. Does that make sense? So if, for instance, you're saying, I wanna start the company but all these things scare me. You go through the fear setting, it still scares you. Part two, and I'll keep it short, is if I stay in my current job and I don't start that company, what does my life look like six months from now? What does the life of my loved ones look like a year from now? How do I feel about myself? How am I relating to the world? What am I making, etc., a year, two years, five years from now? And you have to telescope out and say, if I don't act, what are the costs? And this is not, I don't think it's an evolutionary adaptation that we naturally think in those terms. We think in the cost of action, not inaction.