Big Wins

Chapters

[00:00:00] Introduction — What is proactive tax planning, and why does it matter more than tax preparation?

[00:01:23] Big Wins by the Numbers — Mike reads through the top-15 client savings list from this season, with the lowest win coming in at over $100,000.

[00:06:51] Why You Need a Tax Strategist, Not a Tax Preparer — The difference between an IRS traffic cop and a true tax advocate, and why most CPAs never reach out until January.

[00:11:36] Section 1202: The $700K Win — How one HVAC business owner discovered he could sell his company completely tax-free — after he’d already assumed he owed $700,000.

[00:14:11] Opportunity Zones & Rural Opportunity Zones — A tech worker sitting on a major stock gain finds a legal path to shelter and eventually eliminate that gain by investing in Broken Bow, Oklahoma.

[00:19:20] Step-Up in Basis & Estate Planning — Two cases where inherited assets carried far less tax liability than clients expected — once someone actually looked.

[00:23:25] The Alternate Valuation Date Case — A CPA’s missed estate filing cost a client dearly, and how catching it after the fact still saved the day.

[00:24:59] The Bottom Line — Six months left in the year. Why now is the time to act, and what to look for in a tax advocate.

Most people think tax savings are reserved for the ultra-wealthy. In this episode, Mike Pine and Kevin Schneider pull back the curtain on their biggest client wins from this filing season: real numbers, real strategies, and a clear picture of what proactive tax planning can do for high earners who are willing to be proactive and start before December.

Chapters

[00:00:00] Introduction — What is proactive tax planning, and why does it matter more than tax preparation?

[00:01:23] Big Wins by the Numbers — Mike reads through the top-15 client savings list from this season, with the lowest win coming in at over $100,000.

[00:06:51] Why You Need a Tax Strategist, Not a Tax Preparer — The difference between an IRS traffic cop and a true tax advocate, and why most CPAs never reach out until January.

[00:11:36] Section 1202: The $700K Win — How one HVAC business owner discovered he could sell his company completely tax-free — after he’d already assumed he owed $700,000.

[00:14:11] Opportunity Zones & Rural Opportunity Zones — A tech worker sitting on a major stock gain finds a legal path to shelter and eventually eliminate that gain by investing in Broken Bow, Oklahoma.

[00:19:20] Step-Up in Basis & Estate Planning — Two cases where inherited assets carried far less tax liability than clients expected — once someone actually looked.

[00:23:25] The Alternate Valuation Date Case — A CPA’s missed estate filing cost a client dearly, and how catching it after the fact still saved the day.

[00:24:59] The Bottom Line — Six months left in the year. Why now is the time to act, and what to look for in a tax advocate.