Episode 49: The Road Less Stupid: Making More By Avoiding Losses And Other Financial Advice With Keith Cunningham And Mary Glorfield

TMS 49 | Avoiding Losses


In business, making more can simply mean avoiding losses. Increasing profit doesn’t have to mean doing more when you could just spend less or avoid expense. In this episode, Michael Silvers invites over Mentor Mary Glorfield to interview today’s highly esteemed guest, Keith Cunningham, the CEO of Keys To The Vault: A Business School For Entrepreneurs. Aside from being a successful entrepreneur, acclaimed author and seasoned international speaker, Keith uses his time to teach business owners critical skills that lead to explosive growth. He gives invaluable advice on how to increase revenue by avoiding critical losses and discusses how you can prepare for a crisis. He also shares insights from his latest book, The Road Less Stupid: Advice From The Chairman Of The Board. Tune in for more financial wisdom to equip you on your road to success!

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The Road Less Stupid: Making More By Avoiding Losses And Other Financial Advice With Keith Cunningham And Mary Glorfield

I wanted to thank you for being on. This is a special call because two of my mentors are going to be interviewing each other and giving you a tremendous amount of information and that’s exciting for me. I’m going to take as many notes as all of you out there and remember how to use this, apply it, and don’t wait. That’s all I’m going to say. Everybody knows me already. Without any further ado, a lot of you know who she is already.

Mary Glorfield was the Executive Vice President for Tony Robbins for many years. She did 4 million miles with Tony with three million participants in 82 countries. She went on to do the same thing with T. Harv Eker and put on many of the major events in the US and is still producing them. There’s no one who has done in this industry what Mary has done. I’m going to turn this over to Mary Glorfield.

The key to getting rich is to avoid doing stupid things. You don’t need to do more smart things. You need to do fewer stupid things. Click To Tweet

Thanks, Michael. I’m excited to share this speaker with you and some of you already know him. I’m excited to have Keith Cunningham here. I met Keith and his wife Sandi in Australia. I was immediately impressed with Keith and his content. Sandi is the CEO of their company, Keys to the Vault, and a big part of the company’s success. I know people would agree with that. I have been blessed to be able to put Keith on many stages all over the world and I’m extremely excited that we’ve become friends over those years.

Keith is a seasoned entrepreneur, internationally-known speaker, and acclaimed author. He is regarded as the world’s foremost authority on business mastery. He has taught critical business skills, mentored and coached thousands of top executives and entrepreneurs around the world. He has appeared on stage with industry giants, such as T. Harv Eker, Brian Tracy, Robert Kiyosaki, and Tony Robbins, to name a few.

TMS 49 | Avoiding Losses
Avoiding Losses: A house that can withstand a hurricane versus a house that cannot withstand a hurricane is indistinguishable until after the hurricane.


Keith is an expert at helping business owners, turning fledgling businesses into highly profitable companies with explosive growth. He speaks at Tony Robbins’ Business Mastery. I can tell you that Keith is the only speaker I have observed where Tony has felt comfortable leaving the room and even leaving the city and turning the stage over to Keith. Tony has said, “I would move heaven and Earth to work with Keith. You are not going to get this kind of coaching for less than $100,000 a day.” Keith, welcome. I’m so excited to have you.

Thank you, Mary. I’m so glad to be here and I appreciate the opportunity.

I have a couple of questions for you and then we’re going to open it up for questions from everybody else. I think you would agree. We’re in an unprecedented time in our history. Do you have any specific advice on how people can roll their businesses or maybe even how to thrive or survive in this time?

We are in an unprecedented event, but a crisis is not unprecedented. In my lifetime, I’ve been through four major unprecedented crises that each had different consequences and ripple effects. They impacted different parts of the economy and different businesses in different ways. I love what Warren Buffett has said, “Bad economies do not cause businesses to fail. They expose the weak ones. The weak ones are almost always offense-only. No defense, no dry pattern, no safety net, no plan B.” If you live on the South Coast of Florida, you know there are going to be hurricanes. The key is, “Can you build a house that can withstand a hurricane?”

Progress is sometimes measured by losses avoided. Click To Tweet

What that means is that my experience is that most business owners and entrepreneurs play only offense. They have no defense and yet, if you look at championship teams, you’ll find that the team with the best defense almost always wins. If you look back at the last 15 or 20 Super Bowls and NBA Championships, over and over again, 98% of the time, you’re going to find the team with the best defense wins the championship. Look no further than the Super Bowl in 2021. You had Kansas City and Tampa Bay. Kansas City has got the hottest quarterback in the league. He is a racehorse. Tampa Bay has this old, withering, tired quarterback, but Tampa Bay happened to have a great defense.

Look at the NBA Championship, Phoenix Suns with Milwaukee Bucks. Phoenix Suns had a hot offense. Milwaukee Bucks had one of the best defenses in the league. The key is, “Can we build a company or a business that can withstand future hurricanes?” Now that we’ve had a lockdown and we’ve been through, it wouldn’t surprise me a bit if there were future lockdowns. In fact, what would surprise me is if this is the last lockdown that ever happens in my lifetime, not from COVID-19 or the Delta variant. I’m not talking about this particular crisis. There will be some other thing that happens. Now that we’ve broken the dam of having lockdowns, we’ll have more.

I got to tell you a quick story. Lee Iacocca, who in 1979 was the CEO of Ford Motor Company, got fired by Henry Ford II. There are not a lot of job opportunities after you’ve been fired as the CEO of a major automobile company. It just so happened that Chrysler was going through a crisis and needed a CEO, so Lee Iacocca took the job. Chrysler is a giant financial dodo. They’ve got a huge mess and nobody is loaning them any money. They’re short $1 billion in 1979 to stay alive. The lender of last resort was the federal government.

Lee Iacocca flew to Washington DC and had a meeting with twelve senators and said to them, “Chrysler is going to go broke unless the federal government bails us out.” The federal government said, “No, thank you. We’ve never done that. We will never do that. That is not an option.” Two weeks later, Lee Iacocca met with the same group of senators and said this, “You’re going to write a check. The only question is, how big? If Chrysler goes broke, your check will be $2 billion to pay for all of the unemployment and it will be $1 billion if you decide to bail us out.”

TMS 49 | Avoiding Losses
Avoiding Losses: Great thinking always starts with a question. The quality of your thinking time will be dictated by the quality of the question that you’re going to think about.


In 1979, the federal government, for the first time, bailed out a private company. You and I collectively don’t have enough fingers and toes to count the number of times that the federal government has bailed at a company since then. The idea is that once a precedent has been set, there will be more of the same thing. The key to me is, “In this crisis, what are the lessons that you learned about building a business that can withstand a hurricane?”

I’m not talking about whether or not you lose a couple of shingles. I’m talking about whether or not it blows the house down. The problem is that a house that can withstand a hurricane versus a house that cannot withstand a hurricane is indistinguishable until after the hurricane. What we should be doing is building businesses that can withstand a hurricane. Meaning we’ve got a safety net, dry powder, and some defense, which most people don’t have.

Thank you, Keith. You have a saying, “Not all progress is measured by ground gain. Sometimes, progress is measured by losses avoided.” Can you elaborate on that?

This is my favorite question to ask people. I’m asking you, “If I gave you the opportunity to unwind any three financial decisions you’ve ever made, how much money would you have right now?” You don’t have to tell me. You just think about that. The truth is, for most of us, have we avoided 1 or 2 dumb things, we could be far more financially well off than we currently are. If I was going to put this on a bumper sticker, I would say, “The key to getting rich is to avoid doing stupid things.” That’s the key. I don’t need to do more smart things. I need to do fewer stupid things.

Stupid things have at their root 1 of 3 things. There are only three things in my experience when I look back at my own life that have caused my dumb tax. This is a tax I have to pay every time I do something dumb. The three things are excessive optimism, unexamined assumptions, and number three, ignored risk. When I look back at the dumb taxes, I’ve paid one, if not all of those three things, is obvious. Markets move in cycles and there are times that you can harvest. There are times that no matter how much you want to plant, it’s not a time to plant. It’s a time to tread water.

Opportunity without structure is chaos. Click To Tweet

There are times to harvest and times to tread water. Sometimes when the markets are moving away from us and we tread water, the primary goal should not be making more money. Sometimes the primary goal is to avoid doing something stupid to avoid a loss. Progress sometimes is measured by losses avoided. If we can avoid doing dumb things, then all of us would be better off not only financially but with our lives. What sabotages this is one of three things, excessive optimism, unexamined assumptions and ignored risk.

You have the ability to meet and rub elbows with the rich and the famous, the CEOs, and the big titans in the world. What advice have you received either professionally or personally?

The best advice I ever got in my whole life came after I had paid an enormous dumb tax that cost me all my money. It resulted in bankruptcy. I went from being rich to poor in a short period of time. It was in the real estate business in the 1980s. As a result of that huge dumb tax, that caused me to have to do an entire reset on my life. One of the teachers I had was not a CEO, not somebody that’s rich and famous, but rather a Hindu guru. The Hindu guru that I was listening to said to me one time, “Keith, hell on Earth would be to meet the man you could have been?”

When I heard that, the hair on the back of my neck stood up, it’s a thought that resonated with me. I still every day think about that saying. It would be horrible to meet the person I could have been. I want to be able to meet the man I could have been. I want to be able to look him in the eyeball and say, “I know you because I am you.” What that requires for me is a commitment to mastery, learning, improving and growth. That has become fundamental to my life. It changed my life and it’s the best advice I ever got.

What’s the big risk that you’ve taken in business or the first risk you took?

I’ve taken calculated risk and blind risk. A calculated risk, the first one, was as I was getting out of graduate school and I had an opportunity to work with a bunch of major US companies and I also had an opportunity to work with a smallish business that was in its infancy. The industry was in its infancy, but the two principals of that business were both successful, but they couldn’t pay me a lot of money.

My decision was, “Did I go with the smaller business where I had two mentors, both successful? Was I willing to forego the immediate gratification of a lot of upfront money and instead go for the delayed gratification of money, but in exchange, have two smart people be my mentor?” It was a calculated risk. I left a lot of money on the table for several years by making a choice to go with the smaller company and take a little less money.

My biggest blind risk was the 1980s. I was, by this time, been in business for several years and I had made a tremendous amount of money very fast. The more I made, the more certain I was that my success was the result of my brilliance and astounding business acumen. I kept going all the way in when I should have raked some chips. I was blind to the risk. I love what Bill Gates said on this, “The problem with success is that it lulls smart people into believing they know what they’re doing.” That’s what happened to me. I was astonishingly successful and I thought it meant that I was probably good at it. It turned out I got lucky. I confused my luck for skill and, as a result, made a catastrophic mistake.

That’s probably the biggest financial risk I ever took, but it was a stupid risk that I have learned some very valuable lessons from. I promise you, I will never make that mistake again. There’s a great story that I have to tell. I was invited to speak in Ireland. The promoter of the event asked me the day before the event to go on to a live radio station interview and help promote the event, which was going to happen the next day. I agreed to do it. I was happy to do it. I showed up at the radio station ready for the interview and the disc jockey motioned me into the studio.

TMS 49 | Avoiding Losses
Avoiding Losses: The market really doesn’t care what you got or how passionate you are about what you’re doing. The market wants a problem solved.


We were on a commercial break and the disc jockey said, “Keith, I know about you. I’ve read about you. I know your background. Is there anything you don’t want me to talk about?” I said, “Don’t ask me how it feels to lose $100 million. I’m going to tell you right now, it feels truly horrible. It’s a bad question, so don’t ask me about that.” He said, “Okay, no problem.” He flicked on the little switch and now we were live with the audience. He said to the studio audience, “I’m sitting here with Keith Cunningham, the man who lost $100 million. Keith, how does it feel to lose $100 million?”

I was live on this call and I was irritated. I’ve been set up. I looked at him and said, “Life to me is like a university. Universities have courses and life has courses. I just took a course at the university of life and the tuition was $100 million. Let me tell you two things about this course. Number one, not very many people get to take it. It’s expensive. Number two, the question is not, ‘How does it feel to have spent $100 million?’ The question is, ‘Did I get my money’s worth?’ The answer to that question is yes, which is why I keep a log of lessons learned. It’s one thing to take a risk. It’s another thing to learn the lesson. My experience is that most people fail to learn the lesson and so they get to repeat the course.”

I have not heard that story. That’s great. They set you up every time.

Mary does set me up. I’m going to tell you right now. It’s not fun to lose $100 million.

I know both of you and Sandi are extremely disciplined. There are so many things that I’ve learned from you and Sandi. One of the things that have made a difference that has helped me make decisions in my life and very thoughtful decisions, it’s something that you talked about. It’s the thinking chair, thinking pen, and thinking journal. Can you talk about that process?

There’s a book that was written years ago. It has sold 75 million copies. It’s published in 35 different languages. All of you have heard of this book. Many of you have this book on your bookshelf. A few of you have actually read it. The name of the book is Think and Grow Rich. The name of the book is not Follow Your Passion and Grow Rich. The name of the book is not Dim the Lights, Light the Incense, Sing Kumbaya and a Sack Full of Money is Going to Fall on Your Head. That’s not the name of the book. It’s Think. It turns out that business, investing, and money is intellectual sports. I’m great with people following their passion, but if your passion is going to be financially successful, then the business on the stick is going to be critical.

My experience is, sadly, that most entrepreneurs and business owners spend the vast majority of their time reacting to the crisis du jour, playing Whac-A-Mole, and hand-cranking their business. The reason is because they’re using their emotions, guts, and glands instead of their brains. The key is to design and architect two things, structure and leverage. Opportunity without structure is chaos. The price for entrepreneurial success is structure. Unless you intend to hand-crank as opposed to build a machine, then you’re going to need some leverage.

It turns out that designing, planning, and architecting require thinking as opposed to reacting. If I ask you to look at your calendar or day-timer however you keep your calendar, take a look at the last twelve months and find one 30-minute thinking time session where you sat down to actually think about a problem, obstacle or opportunity. When I challenged most people with this, most people can’t find one 30-minute session in the last twelve months where they closed the door, turned off their phones and computers and sat with a journal and a pen with a question.

Success is getting what you want. Fulfillment is giving what you’ve got. Click To Tweet

Great thinking always starts with a question. The quality of your thinking time will be dictated by the quality of the question that you’re going to think about. If you don’t have a question to think about, I promise you when you sit down to think, you’ll take a nap without question. The key is designing a very robust question and then shutting off all possible distractions for 30 to 45 minutes and keep an empty dot on your page. Every time you write something as a possible answer, put a dot on the page. Right below that answer, write another possible answer, thought, or idea and put a dot. Always have an empty dot because that tells your brain, “There must be at least one more thing.”

This idea of thinking time is something that I learned from probably one of the smartest people I’ve ever met. He was disciplined about setting aside regular thinking time. When I learned it, I forgot to use it for the first 8 or 9 years. After I learned it, I did some stupid things and then I started using it. My life has radically changed as a result of only 2 to 3 thinking time sessions a week with a powerful question. A question might be, “What don’t I see?” What you and I can’t see are our assumptions.

A powerful question would be, “How would I have to run my business so that customers would say, ‘I’d have to be crazy to go someplace else?’ How would I run my business if 100% of my future clients were by referral only? How big would my business be if I still had every customer that ever tried me?” I’m looking for questions that cause me to think. When I’m in a thinking time, I’m not trying to come up with the best answer. I’m trying to come up with a lot of different possibilities. Once the thinking time is over, I’ll call and figure out which ones of those are maybe the high-value ideas.

Somebody said to me one time, “Keith, how do you have a great idea?” I said, “Have a lot of ideas and pick the best one.” That’s what thinking time is designed to do. It’s designed to help you either generate ideas or get clarity on the obstacle that’s in the way. I love what Marcus Aurelius said, “What’s in the way is the way.” I happen to agree with that. Whatever the obstacle is that’s in the way is the way. What I need to do more often than not in my thinking time is get clarity on the obstacle that’s in the way. Once I have clarity on that, I can begin to design possibilities, solutions and opportunities that will help me move the needle from where I am to what I want.

I have a thinking-time chair. The only time I sit in it is when I’m going to think. I have a thinking-time pen and a thinking-time journal. I don’t think on a computer because there are too many distractions. I have journals. Over the course of many years, I’ve developed well over 700 questions that I use for various thinking-time topics. In my book, The Road Less Stupid, you’ll find 704 of those questions. I think you’ll like it. I’ve told people, “You can take away everything I have. You can take away all my money and skills, and leave me only thinking time. I’ll figure out how to get it back.” Thinking time is that powerful.

You’ve had so much success in your life, both personally and professionally. What’s next for you?

Success is getting what you want. Fulfillment is giving what you got. I’m in the fulfillment stage of my life. I’m incredibly grateful for the success and the opportunities that we’ve been given. Some of which, Mary, in fact, where you were at the genesis of, which we’re deeply appreciative. The success at this point is less important. I certainly don’t want to lose anything, but I’m in a fulfillment stage. My way to have fulfillment is with teaching, mentoring, advising, coaching business owners and leadership teams, and helping them avoid doing dumb things.

You’ve certainly been one of my number one mentors for sure and I so appreciate that. I love the story about your first date with Sandi. Would you mind sharing that story with us? There are so many great lessons in there for both men and women.

It’s my favorite story. In the mid-1980s, at the height of my financial success at that time, I was told that I had a meeting. I looked at my day-timer and there was no meeting on my day-timer. My administrative assistant apologized and said she had forgotten to put the meeting on my calendar. I asked who the meeting was with. The meeting was with somebody that owned a magazine and they wanted to sell me advertising which I did not need. The meeting happened. I bought some advertising, even though I didn’t need it because the woman who was calling on me was incredibly attractive. She was beautiful. When she walked into my office, the first thing I said to her was, “I’m not sure what you’re selling, but I’m buying all of it. You are by far the prettiest woman I’ve ever seen.”

Right about that time, the real estate market started to cool off. Now fast forward, many years, I’ve gone broke. I’ve remade my financial success. All of that was handled. I’ve been single for about nine years by then and I was at a party. This friend of mine that I hadn’t seen in a long time asked me what I was doing for my career and my business. He said, “Are you dating anyone? Are you married?” I said, “No, I haven’t remarried. I’ve been single. I’m not dating anyone right now.” He said, “Do you know Sandi?” Sandi was the one that was selling me advertising many years before that I hadn’t seen in fifteen years. I went, “Is Sandi still in Austin? I haven’t thought of her. I haven’t seen her. I would love to see her.”

TMS 49 | Avoiding Losses
The Road Less Stupid: Advice From The Chairman Of The Board

This guy gave me her number. I left the party early. I called her on the phone and asked her to go to dinner, which she reluctantly agreed to. This will show you how bad this was. This got off to a horrible start because she wouldn’t even let me come pick her up. We meet at the restaurant. I said, “Let’s have dinner at 7:30.” She said, “How about if I meet you there at 6:30?” I was thinking, “This is going horrible.” We sit down by 7:00 and we have our first date. This is probably the greatest first date that for sure I’ve ever had. It could be the greatest first date in the history of mankind. We laughed and talked. We were vulnerable. We talked about our past, our mistakes, and the future. This thing is going terrifically well.

At 10:00 that night, it was our first date. I looked at Sandi and said, “I’m about to ask you a question I’ve never asked another woman in my whole life.” She said, “What is it?” I said, “What do you want?” She said, “What do you mean?” I said, “What do you want in a man? What do you want in a relationship?” She said, “That’s easy. I want to be loved and adored.” I called our waiter over to the table and I said, “Bring me a pen and a piece of paper.” I wrote down, “January the 4th, 2001. Sandi, loved and adored.” I said, “Sandi, tell me every single thing that needs to happen for you to feel loved and adored.”

The woman talked for an hour and a half. It was unbelievable. This list kept going. I was writing down every single thing. She finally, at one point, during this long monologue, this woman is high maintenance. At some point, she said, “I want a note every day.” I looked at her and said, “You must be kidding me. A note every day is a lot of pressure every day.” I was struggling to write it down. I looked at her and said, “Sandi, what if I forget?” She said, “That’s not a problem. I’ll remind you,” and she does.

It will be 3:00 in the afternoon and I’ll get a little text that says, “Did the mailman break his leg? What happened to my mailman?” I go, “Shit.” I get busy and I write her a little note. Sometimes the notes rhyme. Sometimes they’re romantic. Sometimes they’re short. Sometimes my notes are nasty because she didn’t tell me what kind of note, but she gets a note every day. The key to the woman’s heart was a note every day. I could have spent 100 years trying to figure that out, which is how I had spent the majority of my time in my prior relationships is I’m busy trying to give somebody what I want to give them instead of what they want.

Sandi is very smart. At the end of that, she said, “That’s it and I reserve the right to add additional items to the list should I think of more,” which she has. She said, “Give me your pen and your piece of paper. What do you want?” I said, “I want to create spectacular. That’s what I want. That’s my word, spectacular.” She said, “Tell me exactly what needs to happen.” There are only three. I told her all three things and that’s what we’ve been about. We’ve been about, “Find out what they want, go and get it, and give it to them.”

The mistake we make as business owners in our relationships is we start with number two. We go and get it and then we got to figure out how to jam it down their throats, instead of simply asking, “What do you want? Let me go and get it. Let me give it to you.” To me, that’s a secret sauce that Sandi and I have. It’s a secret sauce that is at the core of all of our business interests over the years. The market doesn’t care what you got or how passionate you are about what you’re doing. The market wants a problem solved. The market has two things, a gain it wants to get or a pain it wants to avoid.

The market has two things: a gain it wants to get, or a pain that it wants to avoid. Find out what they want, get it, and give it to them. Click To Tweet

Thank you so much, Keith. I admire your relationship. You and Sandi’s relationship is an example of the kind of relationship I would want. It’s amazing. You are probably the most brilliant person I know. Thank you for sharing.

I wanted to thank everybody for being on the show. We know your time is important. This was impactful because, Keith, you gave us things to do immediately and how to look at things in a different way because sometimes we don’t see it until we see it. You gave us a way to start seeing it. I appreciate that. We thank you for being with us.


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About Keith Cunningham

TMS 49 | Avoiding LossesAmerican entrepreneur, international speaker and acclaimed author, Keith Cunningham is regarded as one of the foremost authorities on business mastery. With more than 45 years of business and investing experience, Keith has taught critical business skills to thousands of top executives and entrepreneurs around the world.

Keith is an expert at helping business owners turn fledgling businesses into highly profitable companies with explosive growth. In Keith’s Business School for Entrepreneurs courses, he teaches detailed strategies you can implement even in today’s volatile economy.

Keith is the author of Keys to the Vault: Lessons from the Pros on Raising Money and Igniting Your Business and The Ultimate Blueprint for an Insanely Successful Business. His newest book, The Road Less Stupid: Advice from the Chairman of the Board, is a business book for business readers who want to learn the principles and strategies of making great decisions and minimizing risk. The series of short chapters and subsequent Thinking Time questions are designed to maximize clarity and create better choices… either of which will result in fewer stupid mistakes.

Keith is a dynamic speaker with a sense of humor that will leave you equally as entertained as educated. He is the only speaker who appears with Tony Robbins at Robbins’ Wealth Mastery, Business Mastery and Platinum events.


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