- The biggest mindset shifts for entrepreneurs using AI are beliefs you carry in, not tactics you look up: play big, give it a year, and understand what is at stake.
- It is just as easy for AI to write you an email as it is to build you a rocket ship to the moon, so the question is why you are playing so small.
- In AI, days and weeks feel like years. One conversation, one relationship, or one build can change your whole business inside twelve months.
- The number one skill underneath all of it is signal recognition: taking what you see and hear and turning it into something with AI.
If you are an entrepreneur trying to get more out of AI, the thing holding you back is probably not a tool or a prompt. It is your mindset. The mindset shifts for entrepreneurs using AI matter more than any tactic, because the same tool that drafts a quick email can also build you an autonomous business. What you get out of AI is set by how big you are willing to think before you ever open the chat window.
I watched Wyndham Clark win the 2026 US Open at Shinnecock on Father's Day. He set the record for the lowest 36-hole score in US Open history. Sitting there watching it, I pulled three mindset lessons from that win that map directly onto how I use AI as an entrepreneur. Two came from Wyndham Clark. One came from Scottie Scheffler. I wrote them down the moment I heard them, and they became the spine of how I think about this work.
What are the most important mindset shifts for entrepreneurs using AI?
The most important mindset shifts for entrepreneurs using AI are three beliefs you adopt before you touch the keyboard. Play big. Give it a year. Understand what is at stake. Each one came out of the US Open, and each one changes the size of what you attempt with AI.
Most people skip the mindset and run straight to the tactics. They ask me, can AI do this, can AI do that. I would rather teach you how to fish than give you a fish, because everything is on the table with AI. Once you actually believe everything is on the table, you stop asking small questions. The three shifts below are how you get there.
How does playing big change the way you use AI?
The first lesson came from Wyndham Clark talking about his mom. She had breast cancer and passed away. One of the last things she told him, when he was questioning whether he would even keep playing golf, was two words: play big. He built a foundation around it. It is a core part of who he is now.
When I heard those two words, that was it for me. Play big is the playbook for using AI. Here is why. It is just as easy for AI to write you an email as it is to build you a rocket ship to the moon. The effort on your end is almost the same. So the real question is, why are we playing so small?
I build my own self-auditing mantras for this. One is "impress yourself." Another is "play big." They are reminders I use to check the size of what I am attempting. One of the books I am reading again right now is 10X Is Easier Than 2X. The idea is simple. If you want to 2X your business, do more of the same. If you want to 10X it, you do almost none of what you are doing now and focus on the one thing that actually moves you. That is a play-big mindset applied to your whole business.
So here is the question I want you to sit with. What is the last big thing you created with AI? Not the regular stuff you do every day. Something on the scale of winning your second US Open and going down in history. If you cannot name it, that is the gap. This is one of the clearest mindset shifts for entrepreneurs using AI, and it is also the one most people walk right past. For more on this, I wrote a whole piece on how to dream bigger and make it real.
Why does one year matter so much when you are learning AI?
The second lesson came from Wyndham Clark holding the trophy. He had won a US Open before, then hit some speed bumps over the next year or two. He recommitted, he played big, and he came back. Sitting there after 18, he said, "It's amazing what a year can do."
That line lands hard if you are building with AI. It does not matter where you are right now. You could be at zero, you could be dabbling, or you could be printing work with Claude Code all day. On a day-to-day basis it is easy to miss how fast you are actually moving. But one year from now your life can be completely different, because in the world of AI, days and weeks feel like years.
I will give you a real example from my own year. Less than six months ago I was using ChatGPT exclusively. I had been for three years straight. Now I use Claude for everything, and going back to ChatGPT honestly feels gross. That is how fast the ground moved for me. You are one conversation, one relationship, or one AI build away from everything being completely different in your business. I broke down that whole transition in why I switched from ChatGPT to Claude.
Here is what I want you to notice. I do not have a technical background. Neither do most of the people I work with. We are not romantic about AI. What we have is a big vision for what becomes possible when we actually use it. Over the last three-plus years, nothing I do looks the same year after year. In a year you can build a rocket ship. You can build a business run by AI agents. You can build a life where you work four hours a day. A year is enough.
How do you decide what AI is actually worth to your business?
The third lesson was about Scottie Scheffler. He came into the US Open having won the other three majors. This was the one he needed to complete the Career Grand Slam. They asked him about it, and he said, "It's appropriate to understand what's at stake." For 99% of people that is a throwaway line. For me it was a signal.
Imagine if you took that exact line, dropped it into Claude or ChatGPT, and asked, how does this apply to me and my business using AI? That single move is one of the quieter mindset shifts for entrepreneurs using AI, and it costs you nothing.
Jump on LinkedIn right now and you see the split. Half the people are standing there with pickaxes saying AI is the worst, I can tell you wrote that, look at the em dashes. The other half are saying this is changing my business, come this way, we are going to make everything better. I bring a specific seat to that table. I have no AI background, no tech background, no coding background. I am not the developer. I am the entrepreneur. My goal every day is to be better than I was yesterday, and I have been grinding on that for 16 years straight. So I am unromantic about it. How do I turn a dollar into a dollar fifty?
It is appropriate to understand what is at stake. That does not mean you have to do anything in particular with the answer. What matters more is your ability to ask the question and give yourself the awareness and the context. On my whiteboard I have a line: a willingness to ask better questions. That is the complete key to success in AI. What is at stake right now is the biggest opportunity in the history of the world to make your dreams and goals happen now. You can use it for cooking, parenting, or building a company. The word that matters is opportunity. Those of us who place the bet get to see the chips fall. This is the same ground I cover in what separates the high performers who use AI from everyone else.
What is the number one skill for entrepreneurs in the AI era?
Underneath all three lessons sits one skill: signal recognition. It is the ability to take what you see and hear and use it as the clay you put into AI. I can promise you that not a single other person who watched the US Open on Father's Day saw Wyndham Clark win and then wrote down three notes about how it relates to the AI era. I did, because I am always hunting for words, phrases, and sentences I can co-create on top of.
Signal recognition is what turns a golf tournament into a strategy session. It is what lets you walk through a normal day and come out the other side with ten things to build. The mindset shifts give you the size of the swing. Signal recognition gives you something to swing at. Together they are most of the game. I get deeper into this way of operating in the undeniable way to win in the AI era.
How do you put these mindset shifts for entrepreneurs using AI into practice this week?
You do not need a new tool to use any of this. You need to change how you walk in.
- Play big on one thing. Pick the single most ambitious thing you could attempt with AI this week and start it today. Building a rocket ship costs the same effort as writing the email.
- Run a one-year audit. Write down where you were with AI a year ago and where you are now. Then write where you want to be a year from today, and pick the one conversation, relationship, or build that gets you there.
- Borrow a line. Take any line that catches you this week, drop it into Claude or ChatGPT, and ask how it applies to your business. That is signal recognition in one move.
- Ask a better question. Put "a willingness to ask better questions" somewhere you will see it. Before each AI session, ask a sharper question than you asked last time.
The bottom line
The mindset shifts for entrepreneurs using AI do most of the heavy lifting, and they cost nothing but a decision. Play big, because the tool does not care how big your ask is. Give it a year, because a year in AI rebuilds a person. Understand what is at stake, because the opportunity in front of you is the biggest in the history of the world. Then sharpen your signal recognition so you have something worth swinging at every single day.
Did you watch the US Open? If you pulled your own takeaway that maps onto the AI era, I want to hear it. Send me a DM @robcressy on Instagram or LinkedIn.
Want to build these mindset shifts into how your team actually operates? That is the work inside UNDENIABLE. It is where founders and operators move past AI curiosity and into building real systems, with the mindset and the skills locked in together. If you are ready to play big with AI in your business, come find me and let's get to work.
