The Rundown with Ramon is built for entrepreneurs who actually want to win. In this episode, Ramon Ray talks about why you have to stop “playing checkers” in a world that’s playing chess, how to turn bad situations into brand visibility, what real companies are doing with AI right now, and why you have to challenge your own thinking if you want to grow. He also opens up about his own 2026 business game plan. Don’t miss out – sign up for our YouTube channel.

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Key Takeaways for Entrepreneurs

• Stop playing checkers while everyone else is playing chess. You can’t just react; you have to understand the game, the rules, the players, and your real goal.
• Turn lemons into lemonade. A small company whose truck was used in a high-profile jewel heist didn’t hide from it. They used the moment to get attention and more visibility for their brand.
• AI is not “future tech.” Executives are already using AI daily and tracking ROI. It’s not optional anymore.
• Go beyond the checkbox mindset. Don’t just confirm what you already believe. Try on new ideas and let them challenge you.
• Reinvention is strategy. Ramon shares that he’s in a transition season and lays out his playbook for 2026, including keynote speaking, building platforms for entrepreneurs, and partnering with other leaders.
• Protect your business like you protect your home. You lock your house and your car. Your business needs the same level of security.

Play Chess, Not Checkers

At a recent supplier diversity event hosted by the Manhattan Chamber of Commerce, Ramon challenged entrepreneurs to stop playing checkers while everyone else is playing chess.

Here’s what that means.

Checkers is reacting. You move because something is in front of you. Someone emails you, so you respond. Someone calls, so you answer. You’re constantly in motion, but you’re not in control.

Chess is strategy. You understand the game you’re actually in. You slow down enough to see the board. You know the rules. You know who’s playing. You know what winning looks like for you.

Entrepreneurship is full of things you can’t control. You can’t control taxes. You can’t control the market. You can’t control competitors. You can’t control that someone on your team might disappoint you. You can’t control unexpected hits to your business.

But you can control how you play.

Playing chess means:

• Knowing what business you’re really in
• Knowing who you’re really serving
• Knowing what your real advantage is
• Being honest about your goal

Most business owners are busy. Fewer are strategic. The ones who are strategic win.

Ramon repeats the challenge: Are you even playing the right game? Do you know the score you’re keeping, or are you just staying “busy and tired” with no scoreboard?

This is the mindset shift that separates owners who break through from owners who stay stuck.

Turning Lemons Into Lemonade

There was a high-profile robbery of crown jewels in Paris. The thieves used a specialized telescoping lift truck to reach and move the jewels. That truck came from a small German company that makes cranes and lift equipment.

Here’s the brilliant part.

Instead of panicking over the publicity, the owner went on camera and basically said: “Yes, that was our truck. It’s that capable. Imagine what it can do for your business — legally, of course.”

That is expert marketing instinct.

Why it matters for you:

• A moment happened around their product. They didn’t hide. They framed it.
• They used attention to build credibility.
• They moved fast, and they kept it tasteful.

This is called taking lemons and making lemonade. Most entrepreneurs only look for marketing moments when something good happens. But sometimes the biggest awareness opportunities come from chaos, stress, or surprise.

Ask yourself:

• Did something happen that my audience is already talking about?
• Is there a way to speak to it, with respect, in a way that highlights what we do?
• Can I turn a “problem” into proof of relevance?

That company did not commit the crime. But their equipment became part of a big story. They turned that into visibility. You can do the same when the moment is connected to your brand.

This is also what people call newsjacking: inserting your brand into an active conversation in a way that serves the audience and reminds people you exist.

How Businesses Are Actually Using AI Right Now

Ramon breaks down how leaders are really using AI today — not hype, not theory.

Here’s what matters:

• More than 8 out of 10 executives say they personally use generative AI at least once a week.
• Almost half say they now use it daily.
• Just one year ago, those numbers were much lower.

That is an explosion in behavior.

And this isn’t just curiosity. Companies are tracking ROI. A huge share of executives say they’re actively measuring the return they’re getting on AI and seeing positive results. AI is being built directly into the tools people are already using, so a lot of people are “using AI” even if they wouldn’t say they’re using AI.

There’s also an internal tension. Senior leadership is excited about the vision and long-term transformation. Mid-level managers are often caught in the middle, because they’re the ones who actually have to implement the tools, train the teams, and change the process on the ground.

What this means for you as an entrepreneur:

• If you’re still in “we’ll test AI soon,” you’re already behind people who are standardizing it.
• AI is now part of decision-making, workflow, messaging, marketing, scheduling, and security.
• The question is no longer “Will AI replace people?” The question is “Are you using AI to make the people you have more effective?”

As a small business owner, you cannot afford to burn money on manual work that could be automated. You also cannot afford to hand all your customer experience to slow, human-only processes if your competitors are using intelligent automation to respond in seconds.

AI is not just about speed. It’s about margin. For a lot of entrepreneurs, margin is survival.

Go Beyond the Checkbox Mindset

Ramon highlights a concept from Seth Godin: beyond the checkbox mindset.

Here’s the trap Seth describes.

Most of us are flooded with information — emails, posts, meetings, videos, articles, updates. The default behavior is:

• Scan it quickly.
• If it supports what you already think, you “check the box” and say, “Yup, I agree.”
• If it challenges what you believe, you dismiss it and move on.

That mindset feels efficient, but it keeps you the same.

The alternative is harder, but it’s how you grow:

• When you get new information, don’t just confirm or reject. Try it on.
• Ask, “If this is true, how would I act differently?”
• Ask, “Could this help me, even if it doesn’t feel natural yet?”
• You can always go back to what you were doing. But at least you tested.

This is maturity. This is how leaders evolve.

Entrepreneurs who win are willing to update the way they think, the way they charge, the way they lead, the way they deliver. They don’t cling to “how I’ve always done it.” They cling to “what actually works.”

And this directly connects back to chess vs. checkers. Checkers says, “I already know how I do things.” Chess says, “I’m willing to rethink my play, because the board just changed.”

Ramon’s 2026 Game Plan

Ramon does something most entrepreneurs are afraid to do in public: he tells the truth about where he is right now.

He says clearly that he’s been in a slower season. Things have cooled down. He’s been in a slump. He’s actively re-evaluating who he serves, what he offers, and where he creates the most value.

That honesty matters.

Then he lays out his playbook going into 2026:

1. Continue as a high-energy keynote speaker. The goal is to get in front of rooms and ignite the audience. Corporate events. Associations. Entrepreneur communities. Stages that need energy and direction.
2. Keep building media for entrepreneurs. Daily insights. Training. Interviews. Platforms that help business owners think better and operate smarter. Right now that includes ZoneofGenius.com and the surrounding content ecosystem.
3. Go deeper into partnerships. Not just solo stages, but teaming up with organizers, hosts, and business communities around the country. The plan is to show up, deliver value to their audience, and grow together.

This is important for every founder to hear:

Repositioning is not failure. It’s leadership.

If you’re in a transition, that does not mean you’re done. It means you’re choosing your next level with intention instead of drifting.

Lock Your Business Like You Lock Your House

Ramon ends with a warning that every small business owner needs to take seriously.

You lock your house at night. You lock your car when you park it. You would not leave either one wide open and hope for the best.

But a lot of business owners are basically leaving their business unlocked. Get the small business cybersecurity solution from Bitdefender

That looks like:

• Weak passwords and shared logins
• No backup of bank info, proposals, or contracts
• Clicking “urgent” invoices that aren’t real
• Letting anyone on the team respond to “customer requests” without verifying identity
• Not having a plan for what happens if you get hit by a cyber attack

Most small businesses think, “We’re too small. Nobody’s coming after us.” That thinking is wrong. Small businesses are usually the easiest target.

Treat digital security like basic survival, not “something I’ll get to when I have time.” You are protecting your cash flow, your brand, and the trust of the people who pay you.

Final Word

Here’s the real message of this episode:

Play the right game. Move with intention. Use AI to buy back capacity. Stay open to new thinking. Protect what you’re building. And if you’re in a transition period, don’t hide from it — design it.

Ramon Ray is actively partnering with event hosts, associations, chambers, and entrepreneur communities for 2026. If you’re looking for a keynote speaker to wake up your audience and give them practical, usable direction to grow, reach out to him.