Articles
Articles by Trevor McCandless on tax strategy, multi-generational family wealth, leadership, and building a strong finance function.
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Multi-Generational Wealth Strategies: Beyond the Trust Document
The data on multi-generational wealth is grim. Roughly 70% of family wealth is gone by…
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5 Common Wealth Mistakes Families Don't See Until It's Too Late
The pattern I see most in my practice isn't bad strategy. It's good strategy that…
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The Family Blueprint: How to Plan 20 Years Ahead Without Losing the Next 12 Months
Most financial plans I see are stacks of statements. Allocations, projections, beneficiary forms. They're useful…
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The Quarterly Retreat: How High-Performing Families Run Their Wealth Like a Business
The default cadence for most families is annual. A meeting with the CPA in March…
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Tax Optimization vs. Tax Risk
Most people use "aggressive tax strategy" as a single phrase, as if every plan that…
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Why Tax Season Is the Best Teacher for Young Accountants
Tax season is one of the most intense times of the year inside an accounting…
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Why Intentional Networking Beats Casting a Wide Net
Early in my career I went to every networking event I could find. Meetups. Happy…
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The Art of Deciding What Deserves Your Attention
There's an aura of constant pivoting in the air right now. And deciding what deserves…
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Brain Dump Your Ideas to Find the Real Opportunities
When ideas start flying around, it's easy to get overwhelmed. New opportunities, potential initiatives, exciting…
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Why In-Person Relationships Still Win in Business
For a long time, business growth leaned heavily on digital channels. SEO. Online content. Paid…
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Why My Wife and I Hold a Quarterly Family Meeting
Between running a business, raising two kids, and navigating tax season, it's easy to feel…
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The Enterprise Agent System Is Knocking at Our Door
In several founder groups I'm part of, the same conversation keeps coming up. Tools people…
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Tax Season Is More Than Filing Returns: Here's What We're Really Doing Right Now
We're at that point in the year where roughly 20 to 25 percent of 2026…
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The Tax Season Bottleneck Between CEOs and Bookkeepers
One of the biggest tax season bottlenecks? The gap between the CEO and the bookkeeper.…
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Why Every Question on Your Tax Organizer Matters
People sometimes feel like the tax organizer is a lot. It's a lot of questions.…
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Planning Ahead of 2026 Liquidity Events
Going into 2026, we're seeing a lot of liquidity events. Exits, mergers, acquisitions, and private…
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Building Your Financial Castle: A CPA's Guide to Protecting What You've Built
Here's the harsh reality: 65% of businesses fail within 12 months of a founder's death.…
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How Fresh Talent Resets Team Energy (And When You Know It's Time)
We're three weeks into 2026, and the energy in our office feels completely different. It's…
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Embracing 2026: Leadership, Family, and the Power of Strategic Relationships
Heading into 2026 with a lot of respect for what the year will demand. There…
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What December Teaches Us About What Really Matters in Business
This time of year always slows me down in the best way. We spend months…
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Family Business Changed My Mind
I used to think working with family was a mistake. I had seen the tension…
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Disney Cruise Experience 2025
I recently took a break from the world of finance to go on a five-day…
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Why You Should Check In With Your Business Partners
As a business professional who has worked extensively with various service providers, I have learned…
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Why Your Accountant Should Be Your Confidant
As a tax professional, I have heard this countless times: clients who dread talking to…
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My Professional & Personal Tech Stack
As a CPA, technology is central to everything I do. When we recruit new team…
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My Weekly Restaurant Rotation in San Juan
I live on a little island in San Juan, Puerto Rico, and my office is…
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One of the Most Eye-Opening Moments in My Career
Early in my career, I witnessed something that forever shaped the way I view ownership,…
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The One Thing I’d Do Differently In My Career
I’ve made plenty of mistakes in my career. But if I could go back and…
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The Future of Accounting
I've been thinking a lot lately about the future of accounting. And I don't think…
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The Five-Figure Tax Mistake on a Cruise Ship
I was on a cruise talking shop with another CPA. He was a lifelong controller,…
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The $30K Lesson That Almost Cost Me Everything
At 25, I was living what looked like the dream on paper. I started a…
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