The question that saved a failing business...

Hey reader, David here.

Today, we’re covering Jake’s story. A veteran entrepreneur, he shared something that stopped me cold…

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As I sat down with Jake, a veteran entrepreneur, he shared something that stopped me cold…

Picture this…

He's sitting at his kitchen table at 3am, staring at a bill he can't pay. The numbers blur as his eyes well up with tears.

His wife finds him there, sees his face, and rushes over…

"Oh my God, what's wrong? 

Are you sick?"

"No," he whispers, his voice cracking, "I just can't keep this going anymore."

That moment - that feeling of total defeat - could have been the end of his story…

…But something unexpected happened.

Later, during a brutal round of planned layoffs, one of his contractors said something that would change everything…

"This is going to make an incredible chapter in your story one day if you don't give up."

That remark planted a seed and got Jake to start questioning everything.

Soon, instead of asking, "How do I survive this?"...

…He started asking, "What small progress can we make today?"

That shift? It wasn't just mental.

He applied it by creating small daily actions to keep his business moving forward. 

Today, 15 years after that kitchen table moment, Jake's decision to focus on small daily progress paid off. 

You see…

While most hungry entrepreneurs try to do everything at once, he took it one step at a time because he understood what any great business leader knows… 

Success isn't about one big swing - it's about consistent, small wins that add up. 

Which, for Jake, has resulted in something rare - a business that's not just surviving, but thriving after 15 years, when most don't make it past year one. 

An amazing achievement, and watching him tell this story, I could still see the emotion in his eyes - the memory of that kitchen table moment was still fresh. 

Here's why I'm sharing this with you...

In my years of working with great entrepreneurs and executives from high-growth start-ups and Fortune 500 companies, I've noticed something crucial…

The difference between good leaders and great ones isn't about having all the answers. It's about asking the right questions of themselves.

Most leaders stay stuck asking:

• "What's wrong?"

• "Who's to blame?"

• "How do I fix this fast?"

But the questions that drive real breakthroughs are different:

• What chapter of your story is this challenge writing?

• What mountains feel insurmountable right now?

• What if those mountains are actually laying the foundation for your best work yet?

So, I'm curious…

What's keeping you stuck from achieving your goals right now?

Reply to this email with your biggest challenge.

You see, while Jake's story is powerful, it's not unique. 

From being connected with startup founders to executives at McKinsey & Company, BlackRock, PayPal, Stanford, and Meta, I've noticed something striking - breakthrough moments often come from unexpected questions.

So if you reply, I'll share specific strategies that worked for them and could work for you. And if it feels right, we can explore how focused coaching might help you break through.

(Even if coaching isn't right for you, you'll walk away with at least one practical strategy you can use immediately.)

Remember, sometimes the most powerful question isn't the one you ask others - it's the one someone asks you.

David.

P.S.

Here’s the full podcast with Jake - How Entrepreneurs Think: Building a Winning Mindset https://www.youtube.com/watch?v=80eTvG9QrOA&t=1s