Today we’d like to introduce you to Shay Casler.
Shay, we appreciate you taking the time to share your story with us today. Where does your story begin?
I’ve spent more than 20 years working with taxes and small business owners, but my path here hasn’t been linear. I started my career in tax preparation early on, drawn to the mix of problem-solving, strategy, and helping people make sense of something that often feels overwhelming. Over time, I realized that what clients needed most wasn’t just compliance—they needed clarity, confidence, and someone who could see the bigger picture of their financial lives.
Along the way, I also built and ran other businesses, including a photography business, which gave me firsthand experience with the challenges entrepreneurs face every day. That experience fundamentally shaped how I work with clients now. I don’t just advise from behind a desk—I understand the pressure, the risk, and the responsibility that comes with owning a business.
Casler Financial grew out of that realization. Today, my work focuses on proactive tax strategy, advisory services, and helping business owners build systems that support both profitability and peace of mind. I’m passionate about helping clients move from reactive decision-making to intentional, values-aligned financial leadership. Where I am today is the result of years of technical expertise, entrepreneurial experience, and a deep commitment to helping others build sustainable businesses and lives they actually enjoy.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Not at all—it’s definitely been a road with twists and setbacks. Like many entrepreneurs, I’ve navigated seasons of uncertainty, learning curves, and moments where I had to make hard decisions with incomplete information. One of the biggest challenges was realizing that technical expertise alone isn’t enough to build a sustainable business. I had to learn how to set boundaries, build systems, and shift from doing everything myself to leading more intentionally.
There were also personal seasons that required significant resilience—times when I had to keep the business moving forward while managing life changes and responsibilities outside of work. Those experiences forced me to get very clear on my priorities and values, and they reshaped how I define success.
Ultimately, those challenges became catalysts. They pushed me to build a business that’s not just financially sound, but also sustainable, flexible, and aligned with the life I want to live. Looking back, the struggles were uncomfortable, but they were essential in getting me where I am today.
Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
Casler Financial is a tax advisory and consulting firm built specifically for small business owners who want more than just tax preparation. We specialize in proactive tax strategy, advisory services, and financial clarity—helping clients understand not only what they owe, but why, and how today’s decisions impact their future.
What sets us apart is our emphasis on education, strategy, and relationship. Many of our clients come to us after years of feeling reactive or confused about their finances. We help them move into a more intentional role as business owners by building systems, forecasting proactively, and aligning tax strategy with both business goals and personal values. Because I’ve been a business owner myself, I bring both technical expertise and real-world perspective to the table.
Brand-wise, I’m most proud that Casler Financial is known for trust, clarity, and integrity. We don’t take a one-size-fits-all approach, and we don’t believe in fear-based tax advice. Instead, we focus on thoughtful planning, clear communication, and long-term sustainability—for both the business and the person behind it.
What I want readers to know is that good tax strategy isn’t just about saving money; it’s about creating margin, confidence, and freedom. Our work is ultimately about helping business owners build something that supports their lives, not consumes them.
Before we go, is there anything else you can share with us?
One thing I’d encourage readers to remember is that financial leadership is a skill you can grow into—it’s not something you either have or don’t have. Too many business owners carry unnecessary stress or shame around their finances simply because no one ever taught them how to think strategically about money.
You’re allowed to ask better questions, slow down, and build a business that supports your life instead of competing with it. When you lead with clarity and intention, your numbers become a tool rather than a source of anxiety. That shift alone can be transformational—not just for your business, but for your overall quality of life.
Pricing:
- Tax advisory session $250
- Individual tax preparation billed by the form
- Business/entity tax preparation starting at $2000
- Tax planning packages starting at $1500
- Tax representation services billed at $250 per hour
Contact Info:
- Website: https://www.caslerfinancial.com
- Instagram: https://www.instagram.com/casler_financial?igsh=MTltcjdicGw4eWJkbA%3D%3D&utm_source=qr
- Facebook: https://www.facebook.com/share/1Abmc86qD9/?mibextid=wwXIfr
- LinkedIn: https://www.linkedin.com/in/shay-bachelder-301b1a75?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app
- Twitter: https://x.com/shaycasler?s=21
- Youtube: https://youtube.com/@caslerfinancial?si=clJ8lsfeCBPk890-
- Other: https://www.oregontaxplanning.com
