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Rob Cook isn’t your average tax guy. Yes, he’s a CPA and CFP®, but more than that — he’s a strategist who knows that taxes are your #1 expense and the most overlooked wealth-building lever. In this episode, we dive deep into the power of proactive planning, why tax prep is not the same as tax strategy, and how even savvy entrepreneurs leave money on the table.
Rob shares the mindset shifts, frameworks, and real-life examples that help his clients keep more, grow faster, and live freer. We also talk about the emotional side of money, the myths around real estate and write-offs, and why choosing the right advisor is one of the most important money decisions you’ll ever make.
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Key Takeaways:
- Tax planning is not tax preparation. Strategy starts long before April.
- Your CPA must work with your financial team. Silence between advisors leads to lost money.
- If you’re only a W-2 earner, you’re paying max tax. The IRS rewards investors and business owners.
- Wealth = What You Keep. Taxes are often the single biggest leak in your wealth bucket.
- High-net-worth clients don’t DIY. Rob’s most successful clients build a team of experts.
Memorable Quotes:
- “Most people think tax strategy is just saving receipts. It’s not.” — Rob Cook
- “You shouldn’t be doing this alone. The wealthy never do.” — Krisstina Wise
- “You can’t invest what you give away to the IRS.” — Krisstina Wise
- “There’s a reason the wealthy use entities, trusts, and structures — it’s to legally keep more of their money.” — Rob Cook
- “The goal isn’t to pay zero in taxes. It’s to pay your minimum legal obligation.” — Rob Cook
Time Stamps:
00:00 — Intro to Rob Cook
03:45 — What most people get wrong about taxes
09:22 — Why W-2 income gets taxed the hardest
14:10 — The power of proactive planning
20:30 — What tax strategy actually looks like
27:40 — How the wealthy build teams to protect wealth
35:15 — Rob’s personal philosophies on money and success
43:00 — Final thoughts and resources
Myth Busted:
Most people believe that tax strategy only matters in April — that once you hand everything off to your CPA, your job is done. Rob Cook challenges this myth head-on.
As a CPA and wealth strategist, Rob reveals that by the time tax season arrives, it's already too late to make meaningful changes. The biggest tax-saving opportunities happen months — sometimes years — before returns are filed. From choosing the right entity structure to aligning with wealth-building goals, strategic tax planning is a year-round process.
Rob explains, “Tax prep is compliance. It’s looking backward. But tax strategy is proactive — it’s designing your life and income in a way that minimizes taxes and maximizes wealth.” Most W-2 earners, he notes, are unknowingly paying the highest effective tax rates simply because they never learned how to play the game.
His approach shifts the entire conversation: taxes aren’t a once-a-year burden — they’re a lifelong wealth lever. With the right knowledge and team, anyone can structure their income to keep more of what they earn, legally and confidently.
Resources Mentioned:
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