ON THE BLOG

In Your Corner

In Your Corner

ABOUT THE BLOG

Welcome to my transformative coaching blog, designed to help founders, executives, business owners and leaders think differently and see things more clearly. This is for business owners and leaders who are in the thick of it and value clarity, growth and thinking deeply about leadership — and life.

With each blog post, I’ll be sharing perspective shifts, strategic frameworks, and questions that help leaders think differently. Whether you’re leading a team, running a business, navigating a transition or simply trying to make better decisions, these blogs will help you see things more clearly. I’ll share frameworks you can use immediately, questions that shift your perspective, and real talk about the messy middle of growth and leadership.

I invite you to sign up for my weekly newsletter by clicking the button below. Think of it as having a strategic thought partner in your corner to help you cut through the noise and focus on what actually matters! Some weeks it’ll be tactical, and some weeks it’ll be deeply human. But every week my goal is the same - to give you something that makes you think differently and decide more confidently.

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past newsletters

Kasey D’Amato Kasey D’Amato

The client i turned down this thanksgiving week

A few weeks ago, I was having a casual conversation with a family member at dinner—who happens to be the Chief Marketing Officer (CMO) of a massive $3 billion company.

I love to chat about business, marketing, and growth strategy at any chance I can so that I can learn from people who are a few steps more advanced than me. As we're chatting about how things are going, I start to notice something super interesting—her headaches sound a lot like the ones my smaller-scale clients have.

In fact, what I learned during that 2-hour conversation was:

the billion-dollar companies mirror the same exact challenges of those of us entrepreneurs operating earlier stage 6, 7, or 8-figure ventures.

There were a handful of distinct issues that I found fascinatingly similar!

Read More
Kasey D’Amato Kasey D’Amato

what the government shutdown taught me about leadership

A few weeks ago, I was having a casual conversation with a family member at dinner—who happens to be the Chief Marketing Officer (CMO) of a massive $3 billion company.

I love to chat about business, marketing, and growth strategy at any chance I can so that I can learn from people who are a few steps more advanced than me. As we're chatting about how things are going, I start to notice something super interesting—her headaches sound a lot like the ones my smaller-scale clients have.

In fact, what I learned during that 2-hour conversation was:

the billion-dollar companies mirror the same exact challenges of those of us entrepreneurs operating earlier stage 6, 7, or 8-figure ventures.

There were a handful of distinct issues that I found fascinatingly similar!

Read More
Kasey D’Amato Kasey D’Amato

what turning 49 taught me about leadership

A few weeks ago, I was having a casual conversation with a family member at dinner—who happens to be the Chief Marketing Officer (CMO) of a massive $3 billion company.

I love to chat about business, marketing, and growth strategy at any chance I can so that I can learn from people who are a few steps more advanced than me. As we're chatting about how things are going, I start to notice something super interesting—her headaches sound a lot like the ones my smaller-scale clients have.

In fact, what I learned during that 2-hour conversation was:

the billion-dollar companies mirror the same exact challenges of those of us entrepreneurs operating earlier stage 6, 7, or 8-figure ventures.

There were a handful of distinct issues that I found fascinatingly similar!

Read More
Kasey D’Amato Kasey D’Amato

why your business feels like constant fire drills (and how to stop it)

A few weeks ago, I was having a casual conversation with a family member at dinner—who happens to be the Chief Marketing Officer (CMO) of a massive $3 billion company.

I love to chat about business, marketing, and growth strategy at any chance I can so that I can learn from people who are a few steps more advanced than me. As we're chatting about how things are going, I start to notice something super interesting—her headaches sound a lot like the ones my smaller-scale clients have.

In fact, what I learned during that 2-hour conversation was:

the billion-dollar companies mirror the same exact challenges of those of us entrepreneurs operating earlier stage 6, 7, or 8-figure ventures.

There were a handful of distinct issues that I found fascinatingly similar!

Read More
Kasey D’Amato Kasey D’Amato

The shocking surprises I learned from the CMO of a $3B company

A few weeks ago, I was having a casual conversation with a family member at dinner—who happens to be the Chief Marketing Officer (CMO) of a massive $3 billion company.

I love to chat about business, marketing, and growth strategy at any chance I can so that I can learn from people who are a few steps more advanced than me. As we're chatting about how things are going, I start to notice something super interesting—her headaches sound a lot like the ones my smaller-scale clients have.

In fact, what I learned during that 2-hour conversation was:

the billion-dollar companies mirror the same exact challenges of those of us entrepreneurs operating earlier stage 6, 7, or 8-figure ventures.

There were a handful of distinct issues that I found fascinatingly similar!

Read More
Kasey D’Amato Kasey D’Amato

Why Do I Constantly Feel Like My Business Struggles to Make Money? (Part 1)

If you've ever found yourself scratching your head, feeling utterly bewildered as to why your business perpetually teeters on the brink of financial ruin, let me tell you, you're not alone in that sinking feeling. I swear, every entrepreneur who's taken the plunge into the wild, unpredictable world of business ownership has ridden the rollercoaster of emotions, from the dizzying highs of success to the gut-wrenching lows of uncertainty. Picture those stomach-churning moments when cash flow seems to evaporate faster than a puddle under the blazing sun. It's enough to make you want to pull your hair out!

There's a whole host of reasons lurking beneath the surface of your cash flow woes: a broken business model with profit margins thinner than tissue paper, marketing messaging that's about as exciting as watching paint dry, a lack of diverse marketing efforts leaving your brand adrift in a sea of indifference, a sales strategy that resembles a leaky boat, taking on water faster than you can bail it out, or perhaps, just maybe, an owner (ahem, you) who's been a bit too liberal with the business credit card, splurging on things that don't quite move the needle.

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Kasey D’Amato Kasey D’Amato

Why Women Hold Themselves Back in Business

So, here’s an interesting (and kind of funny) fact I recently came across: in 2023, the number of female CEOs in the S&P 500 finally outnumbered the number of CEOs named “John.” Yep, you read that right. It's a funny comparison but also a bit sad, right? Even though women have made some serious strides in leadership and the corporate world lately, there's still a long way to go.

Maybe you decided to start your own business to break free from the “old boys’ club” and make your own way. But guess what? There are still plenty of ways we women might end up holding ourselves back, even when we're trying to define success on our own terms. Let’s chat about some of the unique challenges you might face as a female entrepreneur and how to tackle them.

Read More

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