Jason Hylan

AI Is Reshaping SEO. Are You Ready?

You've invested time and money building your online presence and visibility. Your site ranks well, it attracts leads, and SEO has been a reliable growth channel. Now AI is changing how people find information online, and you're wondering if all that work still matters. Whether you&

The Google Review Paradox: How AI Search is Reshaping Business Reputation Strategy

You've spent years collecting 50+ five-star Google reviews for your business. Your Google Business Profile looks perfect. ⭐⭐⭐⭐⭐ So why did that AI tool recommend your competitor instead of you when someone asked for the best [your service] nearby? Here's the problem: AI tools can't

The 44.6% Advantage.

Is there a business lesson from tennis? Watching Wimbledon this weekend, a statistic jumped out at me: First serves succeed 81% of the time. Second serves, only 56%. Yes, that's a 25% difference, but 81% is actually 44.6% higher than 56%. So first serves are actually about

Challenges Fuel Motivation

What if I told you that the toughest moments hold the greatest opportunities? That obstacles are a gateway to growth. Challenges fuel my motivation. In fact... * I get energized by them. * I see obstacles as chances to innovate. * As moments to learn from mistakes. * As paths to better solutions. But

When the Forecast Calls for Failure

The Coin Flip: Heads We Light Up the Sky, Tails We Go Home Yesterday I wrote about the parallels between fireworks and entrepreneurship. IMO it taught us a lesson about decision-making under pressure. ➜ The Forecast: Rain and wind threatened to dampen our July 4th celebrations. ➜ The Dilemma: Event organizers faced

Entrepreneurs and Fireworks

What do fireworks and entrepreneurs have in common? I was thinking about how fireworks (in some unexpected ways) mirror the journey entrepreneurs are on: ➜ Controlled chaos Both require managing multiple moving parts with precision timing. ➜ High stakes One misstep can lead to a fizzle. ➜ Brief window of opportunity It’s

I need to fail before I can succeed.

“I need to fail before I can succeed.” Think that sounds crazy? It’s not. It’s actually the truth. If you’re taking big risks … And swinging for the fences … Failure isn't just likely; it's necessary. Think about these phrases: → “I need to feel better

Is Failure Overrated?

The American Psychological Association dropped a bombshell. Failure might not be the great teacher we thought it was. Enter stage left,  “The Exaggerated Benefits of Failure” Wait, what? As leaders and entrepreneurs, we've been sold on the idea that failure is essential. A rite of passage. A badge

Is Criticism Kryptonite?

72% of CEOs admit criticism stings. Criticism can feel like failure. But, handled right, it leads to its opposite - success. Remember when Netflix pivoted from DVDs to streaming after customer complaints? That shift, fueled by criticism, is a prime example of how negative feedback can lead to a positive

Could you handle losing 46% of your battles?

Could you handle losing 46% of your battles? Even the greatest lose half their battles. Roger Federer lost 46% of his points, but won 80% of his matches. Think about that. Here’s why mastering failure is crucial to your success. In tennis and in life, perfection is a myth.

Complexity might impress, but simplicity pays off.

Less is more. But simple is hard. We often overcomplicate things, thinking more is better: - More features - More layers - More everything But what if the key to success is actually simplicity? Try this: 1. Simplify processes 2. Streamline communications 3. Strip away the unnecessary 4. Focus on

Are you prepared for your Game 7 moment?

Last night, the Stanley Cup Finals provided a masterclass in resilience and determination. The Florida Panthers led 3 games to 0, then faced a stunning Edmonton Oilers comeback, only to clinch victory in Game 7. This roller-coaster series mirrors challenges faced in the business world. Let's break down

Is fear holding you back?

Is fear holding you back? Fear isn’t the enemy. In fact, it can be an ally. Fear is a primal response. It's hardwired into our brains. A built-in alarm system keeping us safe. It's there to keep us safe. To alert us to danger. But

Fear fearing Fear

What if your fear of fear was bigger than fear itself? Hear me out. Fear of failure paralyzes us. It leads to self-doubt. It triggers imposter syndrome. It solely serves to limit us. Fear of failure ONLY limits us. Capping our potential. What if, instead, we feared THAT fear? What

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No Mulligans: Lessons from the U.S. Open

Rory McIlroy missed two crucial putts in the last 3 holes at the U.S. Open last weekend. Two. No do-overs. No second chances. No mulligans. Just the harsh reality of a moment that slipped away. Sound familiar? In business, we face our own "crucial putts" every day.

Decisions are free; consequences are not.

Do you know how many decisions the average person makes a day? 35,000.  You may think that sounds outrageous.  Or it may sound grossly understated.  But how many of the 35,000 decisions were truly deliberate? Every decision we make may appear to have no immediate cost. —it'

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Don't play with dead snakes.

Failing matters.

Failing matters. But not in the way you think.

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2 lessons I learned as a founder

As a founder, I've had my share of experiences that have taught me two valuable lessons: 1. the importance of accepting defeat and 2. the need to focus on the long game. Early in my entrepreneurial journey, I found myself getting caught up in short-term metrics. I wasn&

Delegation is not a vanishing act.

Delegation is not a vanishing act. A client of 3 years signed a new contract recently. But not without a comment that made me pause. He joked that my name on the DocuSign was a "fictitious" person, used only for signing documents. Meaning, in his eyes, I was

Advice you won't hear often

Get yourself a mentee. Not a mentor. Not a coach. But get yourself at least one person to pour into and advise. I have mentors and coaches. Highly recommend them. But I find I get just as much value (if not even MORE) from mentoring and coaching others. Here'

It's not luck. 🍀

Last night, the Boston Celtics clinched the NBA championship in a remarkable victory. One of the announcers said it was Jayson Tatum's "growth through failure" that allowed him to succeed tonight. Tatum's relentless work ethic and ability to learn from past experiences (remember the

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Adversity is not personal.

Adversity is not personal. Even our personal adversity. Maybe for you, it's a devastating health diagnosis that's turned your world upside down. Or a spouse who's decided, after years of marriage, that they no longer want to be a part of your life. Perhaps

Fear of failure is a dream killer.

Truth is, it's usually not the failure itself. It's the dreaded "what will they think?" whispers. Reality check: People are BUSY. Your missteps aren't their focus. They've got their own challenges (and TikTok feeds). More dreams are lost to fear