Episode 76: The Curse of Knowledge, with Brett Gilliland

What You Will Learn:

  • Which key three leadership responsibilities are crucial for getting you past the $3 million revenue plateau, and why each helps in making the transition from entrepreneur to CEO
  • Why sharing your Vision with your team isn’t a one-and-done box to check but an ongoing responsibility in every interaction the leader has
  • How the book “Made to Stick: Why Some Ideas Survive and Others Die” by Chip and Dan Heath can be a powerful resource for improving communication effectiveness
  • Why the Curse of Knowledge means we often make incorrect assumptions that people understand what we’re trying to communicate to them
  • How the Heath brothers outlined six key principles that can help you communicate clearly and effectively, and what those principles are
  • How communicating effectively and in a “sticky” way is vital for setting the Vision and leading others toward that Vision
  • How Gamestop’s stock battle between the short-selling hedge funds and retail investors illustrates an important lesson on power, control, and coordination
  • How setting the Vision is about taking coordinated action as one team and ensuring that everyone is clear on the objective and aligned in execution
  • Why developing your leadership skills is instrumental in your journey from entrepreneur to CEO, and how the best leaders build the best businesses


About Brett Gilliland

Brett Gilliland is Founder and CEO of Elite Entrepreneurs, a company that specializes in giving $1M+ business owners the knowledge, processes, and tools to grow to $10M and beyond. Brett is an expert in organization development, leadership, and strategy and spent 10 years helping Infusionsoft grow from $7M in revenue to over $100M. Brett was involved in the foundational work of Purpose, Values, and Mission at Infusionsoft and facilitated the strategic planning process for many years.


One of Brett’s favorite professional accomplishments is co-creating Infusionsoft’s Elite Forum along with Clate Mask and building the Elite business inside of Infusionsoft. As the leader of the Elite business, Brett has helped hundreds of struggling seven-figure business owners overcome their biggest challenges and achieve new levels of success. He also played a central role in the development of Infusionsoft’s Leadership Model and was serving as the VP of Leadership Development when the decision was made to spin the Elite business out of Infusionsoft. As the new owner of Elite Entrepreneurs, Brett can’t think of anything else he’d rather be doing professionally. When Brett isn’t busy helping $1M+ businesses succeed, he is a family man who enjoys spending time with his beautiful wife, Sharon, and their 8 children.




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If you read this blog consistently, you know that typically, we have a guest whom I interview, either a business owner who’s been through the seven-figure growth journey, or at least part of it and has some lessons to share with all of us about things to watch for along the way and practical tips and lessons learned. Sometimes we bring in an expert who knows about a subject matter that might be of assistance to us as we are in the seven-figure growth journey. However, about once a month, most months, I take the opportunity to do what we call a solocast. In other words, it’s just me. I am sharing some thoughts with you that will be helpful to you as your seven-figure journey progresses.

In this episode, I want you to think about the transition from entrepreneur to CEO that you’re making as a seven-figure business owner. Said another way, I want you to go from scrappy superhuman entrepreneur, will it forward, throw it on your back, keep going, drive, grit, and tenacity in all of the things that you do to go from that place to somebody who is now a capable business builder.

That’s a leadership journey. Whether you like to think of it in those terms or not, you’re going through a leadership journey. Your ability to grow your business beyond the $1 million to $3 million mark in revenue will rely completely on how well you can do 3 things. I’ve talked about these before but let me list them quickly. These 3 things are important for you if you want to get past $3 million.

If you’re in the $1 million range, it is important. If you’re in the $3 million range, it’s even more important. Co-create a powerful vision with your team. We usually call that set the vision but I want to underline and emphasize to co-create a powerful vision with your team. When we say vision, what we mean is purpose, values, and mission. Those three components make up a powerful vision.

The second thing you have to do as a leader if you want to grow beyond that $1 to $3 million range is to build a team to accomplish that vision that you’ve set with them. When I say build the team, I mean to develop the team members that you have to make them better tomorrow than you found them now. You’re growing, nurturing, and developing them. Building the team also means adding new members to the team. These are the new hires that you’re going to bring in.

The third thing is that no amount of vision, an amazing team can get anything done if you don’t have the essential element of fuel or runway to enable that growth. You can’t run out of money. A lot of us come from that place. We obsess about the bank account balance and making sure we’re going to have enough in there for payroll or making our accounts payable payments, or whatever it is.

We think about not running out of money and we have to make a transition mentally, and hopefully, financially to a place of securing fuel for growth. When we have a runway, we can stay ahead of the growth of our company. Set the vision, build the team, and secure fuel for growth. Those are essentially your most important responsibilities as a leader starting with set division.

In this episode, we’re going to talk about something that often befuddles business owners that we work with, and that is how much communication is required to effectively set the vision on an ongoing basis. A lot of business owners think that setting the vision is a one-and-done thing. Once you initially set it, are you good to go? The answer to that is an emphatic no.

Setting The Vision

It’s an ongoing responsibility of every great leader to be constantly setting the vision with and for their people. It’s not just for new hires that you’re bringing in to initially say, “Let’s set the vision for you at the outset.” It’s also for current employees, partners, future partners, vendors, and potential customers. Everyone you interact with as the leader of your business needs you to lead in this way.

Again, you don’t own the vision by yourself. You have set the vision initially through a co-creative process with the right team members to make sure we’re all on the same page. We’ve got focus. We’ve got alignment. Everybody’s bought in. There is an initial thing, but once that happens, it’s your number one responsibility to set the vision in an ongoing way and to constantly reinforce that vision through your leadership.

EEP 76 | Curse Of Knowledge

Curse Of Knowledge: You don’t own the business vision by yourself. You set it initially through a co-creative process with the right team members, making sure everyone is on the same page.


The realization that setting the vision is never done is often a new idea and can be a breakthrough for many business owners. Pause for a minute and ask yourself, “How well do I realize that setting the vision is not only my number one responsibility as a leader, but it’s an ongoing responsibility and that it never gets done? I can’t ever check the box and say, ‘Done.’” Hopefully, that was meaningful for you to reflect there for a moment.

The Curse Of Knowledge

Now that we understand there’s a big challenge around knowing that this is an ongoing thing. I have to set the vision. There’s another challenge that comes along as leaders work to consistently set the vision and that’s what I want to talk about in this episode. That challenge is commonly called the curse of knowledge. You’ve probably heard that phrase before. It’s not a new idea but I want to talk to you about the curse of knowledge and how it relates to your job in communicating and constantly setting the vision.

There is a brother duo named Chip and Dan Heath. Hopefully, many of you have heard of Chip and Dan. They wrote a book called Made to Stick: Why Some Ideas Survive and Others Die. In that book, Chip and Dan did a great job of helping us see the impact that the curse of knowledge can have on us as leaders. In the book, they describe a study. There was a study done by a Stanford Psychology PhD candidate named Elizabeth Newton back in 1990. She did this for her PhD dissertation at Stanford University.

EEP 76 | Curse Of Knowledge

Made to Stick: Why Some Ideas Survive and Others Die

The experiment that was conducted was referred to, at least, by the Heath Brothers, as tappers and listeners. I highly recommend you get a copy of Made to Stick, if you have not read it. If you want to improve your communication effectiveness, as a leader as a marketer, or as a human being, there are some great principles in that book. I’ll review the principles quickly at the end of our show but I want to tell you about this study that Elizabeth Newton did.

What she did was assign people to 1 of 2 roles. One of the people had the role of tapper and the other person had the role of listener. She matched these people up. There is one tapper and one listener. The tappers had a list of familiar song titles in front of them. They would look down the song titles and see things like Happy Birthday or The Star-Spangled Banner and immediately, when they saw those titles, they had music going in their head. They had the tunes to those familiar songs going through their mind.

They were asked the question that said, “If you were to tap out the rhythm of that song, no music no humming, no words, just taping out the rhythm of the song.” As a tapper, if I knew the title of the song and I had that music going through my head, if I had a listener there if I had to guess what I thought was the probability that they would get what I was tapping out, 50% of the tappers predicted that the listeners would get the song. Half of them thought, “If I tap this out, it’s a no-brainer. They’re going to guess the song.

The listener was going to listen to tapping and guess what song was being tapped. In actuality and this is shocking, out of the 120 songs that were tapped out, listeners guessed only 2.5% of the songs. 3 out of the 120 were guessed. Why is that so astounding and why did it deserve consideration for Elizabeth’s PhD candidacy? 50% of the chapter tappers thought the listeners would get it right when in reality, it was only 2.5% of those listeners that got it right.

What does that mean? Let’s translate that. If you are a tapper as a leader, you’re going around tapping the rhythm to the vision that you’re always talking about. Even some of those people had spent time, energy, and passion in helping you co-create that vision but you’re out there tapping in ways that you think make total sense to your readers. You would guess that at least half of them are going to get it right from your tapping but in reality, instead of 1 out of 2 that you thought as a tapper would understand what you were trying to tap, 1 out of 40 knew what was going on or could guess.

That’s a little difficult to talk about in this episode, but I want you to think about the implications for you as a leader. If you go around your business, your team, your community or organization where you volunteer, wherever you are trying to communicate and get people to understand, remember, buy into something. You can go into those settings with the music in your head and you can tap like crazy and never get your message to stick. That’s why I love what the Heath Brothers have done with their book Made to Stick. I didn’t mean to do a whole episode here on Made to Stick, but I highly recommend you check it out.

What’s fascinating about this is that the tappers were flabbergasted at how hard the listeners seemed to be working to pick up the tune. They’re like, “This is so simple. I’m tapping it. Can’t you hear it? Can’t you get it from my tapping?” By the way, if I were to tap the rhythm to Happy Birthday as I did and then tap for you the rhythm of The Star-Spangled Banner, maybe some of you, musically-inclined people out there would already guess that it’s the same exact rhythm.

If I tap “Happy birthday to you,” or I tap, “O say, can you see,” the tapping is exactly the same. I probably made a mistake by putting some music to it. I’m not a great singer but I hope you get the point. You’re tapping doesn’t translate to the song that you’re hearing in your head. In many cases, you’re tapping Happy Birthday but somebody else is hearing The Star-Spangled Banner because the rhythm is the same.

As a leader, you might be thinking, “How could these people not get this?” In fact, even if you hadn’t had this reference to tapping and listening, you have had the experience of at least thinking to yourself, “I’ve said the same thing seven times and they’re finally picking it up or they still don’t get it.” We almost question people’s intelligence because of how much we’re saying the same things and they’re not picking it up.

You are like, “I am laying it down and they’re not picking it up.” It’s not the effect of their poor intelligence. Unfortunately, this is another one of those mirror moments for us as leaders on our leadership journey. We have to learn how to be more effective in communicating key messages to our people. Not just our team, but to anybody who needs to know what we’re up to. How are we going about doing it? Why it should matter to them? Again, this could apply to prospective customers, partners, vendors, or anybody with whom you need to communicate and have it stick with them. We have to be more effective as communicators.

Entrepreneurs must learn how to be more effective in communicating key messages not just to their team but to anybody who needs to know what they are up to. Click To Tweet

Heath Brothers’ Six Principles

What does that look like? I thought I would share with you the six principles that the Heath brothers outlined in their book Made to Stick, and I can’t get into any detail on these so you’re just going to have to go look it up or the book. Listen to it. It’s awesome. Principle 1) Simplicity. It’s got to be simple enough for people to get it. If you have to argue a bunch of points, if you have to make a bunch of complex supporting statements, it’s not simple enough.

Principle 2) Unexpectedness. How do we keep them from blanking out or assuming they know what you’re saying? Sometimes we need to use the element of surprise a little bit to have them go, “That was unexpected,” so that they can be open to receiving. Principle 3) Concreteness. I’m guilty of this all the time. I live in the land of ideas. I’m more intuitive. I got my head in the clouds a lot and the people that I work with or communicate with, many of you included, wished that I were more concrete. I have to have to push myself to use concrete examples to get people to know what I’m talking about.

Principle 4) Credibility. If you have lost credibility with your audience, you might need to do some things to get that back or you can leverage the credibility of a third party, somebody else. Principle 5) Emotions. It’s related in my mind and I don’t know if the Heath brothers would say this but that idea of unexpectedness is jolting their mental frame to get them to see something different than they had before but emotions make things stick.

Not to dwell on music too long, but there’s a power in music that elicits emotional response. At least, well-written music does that for many people. Just like music communicates through feeling or emotions often, our communication could learn another lesson from music around taping into emotions. Finally, the Principle 6) Stories. How do we get people to act on our ideas? We tell stories. Stories tend to stick a lot better than just teaching principles or practices.

I’m not here to do a book review or to do an in-depth summary but I’ve taught you about the curse of knowledge that we all have as leaders. You can’t not have the curse of knowledge. If I were here as a doctor trying to diagnose one of your problems, I’m going to tell you emphatically and definitively, “You have the curse of knowledge.” There are no exceptions out there. You can’t say, “No, I don’t.” Yes, you do. We all have the curse of knowledge.

When we go to communicate, we’re going into tapping mode. We’re assuming they hear the music just like I do when in fact in reality, only 2.5% of the time are they hearing what you’re putting out there with the tapping. That’s the six principles of making your messages more sticky. You can go check out the Heath brothers’ Made to Stick if you want if you want to learn more about that.

Communication To Stick

I want all of us as leaders to be better at making our communication is made to stick. When we set the vision, we don’t want to say it once and have it go in one ear and out the other ear. We don’t want to go over their head. We don’t want them to blink and miss it. Whatever example or analogy you resonate with, we don’t want them to not get it. We want them to get it. Not only do we want them to get it, we want them to be excited about it and we want them to take action.

Good communication leads to people taking the desired action. That’s what it’s about. We don’t communicate to hear ourselves. We like to hear ourselves. Most people like to hear themselves talking over listening to somebody else. However, it’s not in our heart of hearts to have our voice be heard. We want people to do something as a result of what we’re sharing. It’s an important part of our leadership journey that we learn how to communicate effectively in ways that not only stick with people but that they can now take the desired action. We want everyone pulling in the same direction.

Good communication leads to people taking the desired action. Entrepreneurs don’t just communicate to hear themselves. Click To Tweet

GameStop Stock

Before I wrap up, I want to reference an event that ties into what I’m sharing now. It may surprise you a little bit. You might hear me talk about this event and go, “What in the world does that have to do with Made to Stick or anything that Brett’s talked about around setting the vision?” Here’s what I want to reference. If you were paying attention to the business news at all, you would have learned or heard about the fascinating thing that happened with GameStop stock.

I’m not an expert on telling the details of the story and nor are the details of the story super important for our purposes, but the gist of it is that there was at least one large notable hedge fund involved who shorted the stock. In other words, they anticipated that the stock price was going to go down so they wanted to sell a price with the promise of buying at a lower price if it got there.

They made a huge bet and poured millions of dollars, but it resulted in billions of dollars of impact on them. They lost investment when a large group of well-traded coordinated individual traders got together and drove up the price of GameStop stock through their interests, through their purchasing activity. The hedge fund thought the price was going to go way down. The individual traders all got together and drove the price way up, and the hedge fund lost out big time.

Billions of dollars were lost at the hands of a large number of well-coordinated individual traders. If you have not heard about that story, you go check it out. There are plenty of plenty of opportunities here. It’s all over the place. The details aren’t that important for the point I want to make for the solocast but here’s what I want to share. Many people wrote or commented about this incident, more than I can count.

Buried in one of those articles is a genius quote, a gem that he’ll never know probably that I’m referencing his article on my show and then I’m sharing it in the context that I’m sharing it now. His name is Kaihan Krippendorff. He’s the Founder of Outthinker. He’s a Senior Advisor at Coplex. He’s a keynote speaker and author on strategy innovation and transformation. If you’re interested, look him up.

He wrote an article about the stock of GameStop and what went down. Buried in this article was a quote that jumped off the page at me. Here’s the quote. “What we need to do is appreciate that power increasingly comes from coordination, not control.” Brilliant words by Kaihan. Again, he might be surprised that I’m using it in the context I am now. What in the world does that have to do with our topic of setting the vision?

He was referring to the power that the Army of well-coordinated individual traders had against the major hedge fund. That major hedge fund was used to control significant levers in the financial markets. They made big bets. They hyped up. They influenced others’ thinking for the market to move in directions that would favor them. I’m not suggesting that they’re doing anything illegal. I’m just saying they have a lot of power.

In this case, they weren’t able to control anything. I want you to think about this quote from a different lens now. Through setting the vision, our job as a leader to set the vision is a mechanism by which we coordinate efforts and resources in our businesses. I want you to ask yourself. Do you think you will be more powerful if you maintain all of the control in your business? Is it possible that you will be more powerful if you coordinate thought, energy, focus, resources, and commitment in your business?

It’s a little scary for some of us to think about that, especially if we’re the founder. For the founder, we controlled everything in the beginning. We had to learn how to do everything or else it wouldn’t get done and we learned how to do it well. We then started bringing team members in and we had a hard time letting go because we knew it had to go. Now, we’re trying to bring somebody in to help and we have a hard time letting go and relinquishing control.

At the end of the day, do you have more power as a leader if you maintain control or if you relinquish control and learn how to masterfully coordinate thought, energy, focus, resources, and commitment? How much more influence, leadership, or power could you unleash if you were better at coordinating and controlling less? What I want to submit to you in this episode is that setting the vision is how we coordinate more.

It is how we feel more comfortable letting go of control. When everyone on the team knows what’s happening especially if they’ve been involved in creating it, there’s so much more that we can do together than any one of us here. As superhuman as you may be as the founder-entrepreneur, you can’t do it all. Your power is limited until you begin to coordinate others’ actions.

EEP 76 | Curse Of Knowledge

Curse Of Knowledge: There is so much more entrepreneurs when they work together. You cannot do it all. Your power is limited until you begin to coordinate your actions with other people.


People talk about getting teams to run in the same direction. I call it taking targeted coordinated action as one team. Setting the vision is making sure everyone is clear on the objective and that everyone is aligned in the execution. It’s coordination, not control. With that, I hope this episode has been helpful to you as you continue on your leadership journey. I hope you consider yourself to be on a leadership journey because there is no way to go from a $1 million entrepreneur mindset to a $10 million CEO.

You might not even have an aspiration to get to $10 million and maybe you despise the term CEO. However, for any growth objectives or aspirations you have beyond the $1 million entrepreneur mark, you must be on a leadership journey. You must figure out how to go from being in control to coordinating efforts. Targeted coordinated effort is what we have to do as one team. Otherwise, we hit a ceiling. We can grow no further.

Winning Business

Again, I hope this has been helpful. I’m going to end with a thought I frequently reference but I want to sear it into your brain. Think of me using a branding iron and that may be cruel. Some of you might be like, “I can’t believe we brand cattle,” but I’m trying to burn something in your mind especially if you don’t think you’re on a leadership journey as a business owner.

Here’s the thought. “The best leaders build the best businesses and the best businesses win.” That’s true always. Whether we’re in a pandemic, coming out of a pandemic, in a bear market, a bull market, or when times are good or bad, it doesn’t matter. The best leaders always build winning businesses. They build the best businesses. They build very successful businesses full of great people who do great work and those businesses win.

The best leaders build the best businesses, and the best businesses win. Click To Tweet

If in the short term, they hit some challenges, they learn. They figure it out. They innovate and they come back out on top. They always win in the end. If you want to build the best business that wins, you must become the best leader. I hope that my thoughts on your ongoing responsibility to set the vision are not a one-and-done checklist item at the front end of your job as a leader but an ongoing integral part of how you lead people to take targeted coordinated action on an ongoing basis as one team.

I hope that’s been helpful to you and that you’ll continue reading. We’ll continue to bring great guests. Some of them are business owners just like you and some of them are business owners that are a step or two ahead of you and can share some lessons. Some of them are experts who know very specific things that will help you along the way. I look forward to the next time I have an opportunity to share some of my thoughts as well. Keep reading. Keep sharing. Keep liking. Help us spread the word that we are here to help seven-figure businesses build meaningful businesses and have a ton of fun and satisfaction along the way.


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