Overconfidence Bias: The #1 Financial Blindspot to Avoid
"What gets us into trouble is not what we don't know. It's what we know for sure that just ain't...
By: Shane Bender on Feb 17, 2025 3:16:23 PM
Growing a business isn’t just about hard work and hustle—it’s about making smart decisions. And no matter how experienced you are, there will always be gaps in your knowledge. That’s why the most successful business owners surround themselves with key advisors—experts who provide guidance, strategy, and perspective to help them scale and protect their business.
I recently sat down with Kyle Gabhart, Managing Partner of Bluegrass Legacy Group, to talk about the importance of financial advisors, fractional executives, legal counsel, and other key business partners. Kyle shared his journey from corporate consulting to entrepreneurship and why business owners must strike the right balance between reinvesting in their business and securing their long-term financial future.
📽 Watch the full conversation with Kyle Gabhart below!
Let’s dive into the biggest takeaways from our conversation.
No business owner can succeed alone. Whether it’s financial decisions, legal strategies, or operational improvements, the right advisors can help you avoid costly mistakes and set your company up for long-term success.
Kyle emphasized the power of collaboration, referencing Proverbs 15:22: "Without counsel, plans fail, but with many advisors, they succeed."
So, who should be in your circle? Here are some essential advisors for growing businesses:
One of the biggest questions business owners face is:
“Should I reinvest in my business, or should I diversify my investments?”
Kyle explained a critical principle:
Wealth is built through concentration but protected through diversification.
This means early on, doubling down on your business may be the smartest move—pouring resources into improving your processes, hiring key staff, and growing revenue. But at a certain point, business owners should start diversifying investments to ensure they aren’t putting all their financial future into one venture.
Here’s a simple rule of thumb:
Business owners often face unique financial challenges that traditional investment strategies don’t fully address. According to Kyle, these are some of the most common financial missteps entrepreneurs make:
By working with a fractional CFO and a strong financial advisory team, business owners can avoid these pitfalls and build a more resilient financial future.
Running a business isn’t just about making money—it’s about purpose.
Kyle shared how, after years in corporate consulting, he realized he wasn’t making a real impact. That’s what led him to transition to personal finance, where he could see the direct results of his work on families and business owners.
For many entrepreneurs, burnout happens when they lose sight of their "why." The key to staying motivated long-term?
At Bender CFO Services, we help marketing agencies and other B2B service businesses build a strong financial foundation that supports their growth. Our fractional CFO services go beyond just managing numbers—we help business owners:
✅ Forecast revenue and expenses with confidence
✅ Improve cash flow and profitability
✅ Plan for long-term financial security
✅ Make smart reinvestment and diversification decisions
Whether you’re navigating rapid growth, planning an exit, or simply want more clarity on your finances, we’re here to help. Let’s talk about how to optimize your financial strategy for long-term success.
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