About Uncle Aaron - Life Advice, from your Favorite Uncle..

Uncle Aaron

wasn’t something I just woke up as one day. No one hands you that title, not even after years of giving advice, picking yourself up after a setback, or figuring out how to navigate the curveballs life throws at you. It’s a name that comes from living through those ups and downs and sharing what you’ve learned with others. This book is about resilience—the kind you build over time, through hustle, hard lessons, and the people who guide you along the way.

My Experience

My journey began, like many do, with a paper route. My mother, juggling two jobs and putting herself through school, thought it would teach me responsibility. Naturally, she signed me up for two paper routes instead of one (because why do anything halfway, right?). That was my introduction to the grind—learning to show up day in and day out, no matter how tired I was, no matter how early the morning.

From there, life was a series of hustles. I cut lettuce at a sandwich shop as a teenager, ran my own towing company, and taught myself web development back when the internet was in its infancy. I didn’t stick to the traditional path—if there even is such a thing. Every job, every experience, taught me something, often the hard way. But those lessons built the foundation of the resilience I’d need later in life.

Welcome to Uncle Aaron - No BS - Life Advice, from your Favorite Uncle..

Here’s the Short Version:

Hey there, I’m Aaron Kershaw—though most younger folks just call me Uncle Aaron or Mister K. I’m not here to say I’ve got all the answers, but I’ve picked up a few solid ones in my time as a father of 4, grandfather of 2, and uncle to 8 nieces and nephews. Trust me, I’ve given my fair share of advice.

Life’s messy, and no one’s got it completely figured out. But I’ve been around the block—whether it was serving as a U.S. Marine, working as a photographer, running businesses, offering financial advice, driving tow trucks, or producing radio shows. Every step taught me something, and I’m here to share those lessons with you, mixed with a bit of humor and a whole lot of honesty.

Think of me as that sarcastic, experienced uncle who’s seen it all, made a ton of mistakes, and is here to help you avoid making the same ones. Whether you’re navigating relationships, starting a business, or just trying to figure out this whole “adulting” thing, I’ve got real-life wisdom you can rely on.

So, if you’re ready for practical advice with a few laughs along the way, welcome to Uncle Aaron’s world. Let’s figure this out together.

Back to School at 48: Reinventing Myself (Again)

Just when I thought my path had taken shape, life threw another twist. At 48 years old, I found myself back in school. Yep, I was a freshman at Manhattanville College, sitting in classrooms with kids who were younger than my daughter. For the first two years, I was in an adult program, and let me tell you, I was on fire—4.0 GPA, fully focused. It felt like I was finally making up for lost time.

Then came COVID-19, and with it, a complete shift in how I thought things would go. The adult program changed, and suddenly, I was in classes full of 18-year-olds. At first, it felt surreal. I was the guy in class who had decades of life experience, while they were just starting out. But you know what? They had as much to teach me as the professors. These students were navigating college with fresh tools and strategies I hadn’t even considered.

We started learning from each other, and somewhere along the way, these kids started calling me Uncle Aaron. At first, it was a joke. But then, it stuck. They found my advice useful, and to my surprise, they actually listened. This was when I first realized that the lessons I’d gathered over the years—the hard-earned wisdom and resilience—might just have something to offer beyond my own experience.

Setting Goals &Taking Action

One of the most powerful aspects of resilience is the ability to set new goals and work toward them. After my injury, I had to pivot my career and rethink my path forward.

The Pivot into Finance: A New Path at 50

Then came another twist—this time, into the world of finance. After two years in college, I met Rich, a local financial advisor who saw potential in me and gave me an opportunity I never expected. At 50 years old, I started learning about the industry from the ground up. It was a career I hadn’t imagined for myself, but it felt right. Rich gave me the chance to apply all those years of life experience in a new and meaningful way.

But like any journey, there were bumps along the way. Early in my financial career, I decided that one advisor didn’t agree with, and he cut me off for six months—completely ghosted me. Full-on manchild mode. But that rejection pushed me to seek out other mentors—the uncles—who became a core part of my growth.

I ended up working with five other amazing financial advisors, each of whom helped me shape my career and figure out what kind of financial advisor—and person—I really wanted to be. And then there was Bucci. He wasn’t just a mentor—he became like a brother. His advice wasn’t just about the numbers; it was about life. He guided me through tough moments, offering the kind of wisdom and humor that only someone who’s walked a similar path can give.

Thanks to people like Mike and the other Uncles, I realized that resilience isn’t just about toughing it out. It’s about evolving, adapting, and finding the right support system when life throws you a curveball. It’s about having the resilience to reinvent yourself, time and time again, without losing the essence of who you are.

Uncle Aaron: More Than a Name

As I grew into my role in finance, and the title “Uncle Aaron” began to stick, I realized that I had more to share. It wasn’t just about career advice or personal finance tips—it was about the bigger picture. Resilience, growth, and reinvention are not just things you learn once and move on from. They’re lifelong skills, and they’re what this book is all about.

Life isn’t about finding the perfect path. It’s about learning to pivot when needed, evolving when life changes, and building the kind of resilience that lets you keep going, even when things don’t go according to plan. It’s about having a sense of humor about it, too—because if you can’t laugh at the messiness of life, what’s the point?