Story & Lesson Highlights with Shay Bachelder

We’re looking forward to introducing you to Shay Bachelder. Check out our conversation below.

Good morning Shay, we’re so happy to have you here with us and we’d love to explore your story and how you think about life and legacy and so much more. So let’s start with a question we often ask: Who are you learning from right now?
I’m learning from a professional network called ProInsight, which I joined almost two years ago. I originally joined to build referral relationships, but it has grown into so much more. Through ProInsight, I’m learning how to leverage my existing client base, deepen professional partnerships, and become more referable. It’s teaching me not only how to serve my clients better by connecting them with trusted experts, but also how to think more strategically about scaling and sustaining my business.

Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Shay Bachelder, and I’m a tax advisor at Casler Financial, where we go far beyond preparing returns. Our brand is built on trusted relationships — guiding clients not just through tax compliance, but through life’s bigger financial decisions. What makes Casler Financial unique is our holistic, relationship-driven approach: when clients come to us with questions, they know they’ll get more than answers — they’ll get connections to trusted professionals and strategies that truly support their goals. For me, this work is about being a partner in my clients’ success, helping them feel confident and supported in every stage of life.

Okay, so here’s a deep one: What breaks the bonds between people—and what restores them?
What I’ve seen is that bonds between people are often broken not by dramatic events, but by small cracks left unattended — a lack of communication, a breach of trust, or simply neglecting to nurture the relationship. Distance grows when we stop listening or when self-interest outweighs mutual respect. Yet, those same bonds can be restored through honesty, empathy, and consistent presence. A genuine conversation, an act of forgiveness, or even showing up reliably over time has the power to rebuild what was lost. At the heart of it, connection is sustained when we choose to value the relationship as much as the outcome.

If you could say one kind thing to your younger self, what would it be?
If I could say one kind thing to my younger self, it would be: you don’t have to have it all figured out right away. The path will unfold, and every experience — even the setbacks — will shape you into someone stronger, wiser, and more compassionate. Trust yourself, stay curious, and remember that growth comes just as much from the journey as from the destination. (But get good tax and business advice along the way… it will help you tremendously!)

Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. What would your closest friends say really matters to you?
My closest friends would probably say that what really matters to me is people — building trust, showing up for others, and creating relationships that go beyond the surface. They know I care about integrity and doing the right thing, even when it’s not the easiest path. They’d also say that I value growth — both my own and helping others grow — whether that’s in business, in personal life, or simply in the way we show up for each other.

Okay, we’ve made it essentially to the end. One last question before you go. What is the story you hope people tell about you when you’re gone?
I hope the story people tell about me is that I lived with integrity and kindness, that I showed up for others in ways that made them feel seen and supported. I’d want people to say that I invested in relationships, not just transactions, and that I left things better than I found them — whether in my work, my community, or my personal connections. More than anything, I’d hope they remember that I cared deeply and that my actions reflected that care.

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Image Credits
Kelly Mooney Photography

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