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The Entrepreneur's Tax Playbook

Most high-earning business owners overpay $30K–$120K in taxes every year.

Not because they're careless — because nobody is paid to sit across from them and look at the entire picture. Good Deals Advisors closes that gap. Start with the free playbook below.

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Andrew Escher, CFA · Registered Investment Adviser (TX) · Austin · Flat-fee fiduciary · No commissions, no product sales
The Core Frame

The 4 Jobs of Every Dollar

Every dollar your business earns has exactly four possible destinations. No dollar you've ever earned has done anything else. The goal is simple: shrink Job 1, expand Jobs 2, 3, and 4.

JOB 1

Taxes

The government's cut. The one job you want to shrink.

JOB 2

Living

Your lifestyle. The life the business is supposed to fund.

JOB 3

Investing

Money you send into the future.

JOB 4

Giving

Money you send into the world.

The principle: The tax code isn't punishment — it's a list of incentives. The government wants you to start businesses, hire people, invest, fund retirement, and give. Your job is to do the things they're already paying you to do. Most of the difference between two identical earners — one who retires comfortable, one who retires wealthy — isn't returns. It's structure.

The Playbook

Five layers of keeping more of what you earn

Ordered by impact. Start at the top, work down — every layer builds on the last. Here's what's inside the full playbook.

Layer 1 · Entity Structure

S-Corp election + Accountable Plan

Net profit over ~$80K? An S-Corp election stops the 15.3% self-employment tax on distributions. Stack a written Accountable Plan to reimburse home office, phone, mileage and travel — tax-free to you, deductible by the business.

Combined impact: $23K–$35K / year recurring
Layer 2 · Retirement Vehicles

Solo 401(k) · HSA · Backdoor Roth

The Solo 401(k) is the single biggest retirement tool in the code — up to $69K combined ($76.5K at 50+). Add the triple-tax-advantaged HSA and a Backdoor Roth for high earners phased out of direct Roth.

Combined impact: $25K–$40K / year + tax-free growth
Layer 3 · Business Tactics

Augusta Rule · Depreciation · QBI

Rent your home to your business up to 14 days a year — tax-free (§280A). Time equipment buys for 100% bonus depreciation (restored under OBBBA). Optimize the 20% QBI deduction around the phase-outs.

Combined impact: $15K–$60K / year, situation-dependent
Layer 4 · Investment Efficiency

Asset location · Loss harvesting · 1031

Where you hold each asset is worth 1–2% of after-tax return a year. Harvest losses against the wash-sale rule. Chain 1031 exchanges to defer real estate gains indefinitely — then step up at death.

Combined impact: $10K–$40K / year on a $1M+ portfolio
Layer 5 · Giving That Pays You Back

Appreciated stock · DAF · QCD

Donate appreciated stock instead of cash — full deduction, zero capital gains. Bunch years of giving into a Donor-Advised Fund to recapture deductions. QCDs (70½+) never count as income and satisfy your RMD.

Combined impact: $15K–$40K / year — same gift, better outcome

Typical total impact

$50K–$110K a year in recurring tax savings for an owner earning $500K–$1M. Not one-time. Every year. Compounding for decades.

Why this is left on the table

The coordination problem

Why doesn't every business owner already do this? It isn't laziness, and the strategies aren't hard. The answer is structural — nobody's job is to watch the whole board.

Your CPA is a historian

Their job is to report what you did last year. They won't call you in June to reorganize your entity. That's not the engagement.

Your advisor is a tailor

They optimize the last dollar — the one that already survived the tax code. They're playing for 3% while the code offers 20%.

Your attorney drafts documents

On request. They don't watch your numbers or update your plan when your income doubles. They wait for the phone to ring.

Nobody is paid a flat fee to sit across from you and look at the entire picture. That gap is where the money lives — and closing it is the job Good Deals Advisors was built to do.

Free download

The one-page Tax Cheat Sheet

Every strategy in the playbook on a single page you can hand straight to your CPA. Updated for 2026 tax law (post-OBBBA).

  • All 5 layers, with typical dollar ranges per strategy
  • A Quick-Wins checklist to take to your next CPA meeting
  • The exact moves owners earning $500K–$1M use to save $50K–$110K a year

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For educational purposes — consult your CPA before implementing.

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Andrew Escher, CFA

Andrew Escher, CFA

Founder, Good Deals Advisors · Austin, TX
10,000+hours as a Fractional CFO to 30+ companies
$300M+revenue run through his systems
9-figuresoftware exit, led the financial side
CFA+ Series 65 · Fiduciary to every client
Who's behind this

CFO-level rigor, applied to your whole financial life

Andrew is a CFA charterholder and the founder of Good Deals Advisors, a Registered Investment Adviser with the Texas State Securities Board. Before Good Deals, he spent 10,000+ hours as a Fractional CFO and helped take a Kansas City software company from scrappy startup to a nine-figure acquisition.

Good Deals doesn't take commissions, sell insurance as a primary business, or accept referral fees. What that buys you:

  • Flat-fee annual planning — no commissions, no product sales, no quotas
  • One relationship covering tax, investments, retirement, business structure, and estate coordination
  • Fiduciary to every client, every decision, every quarter

What does this look like for you, specifically?

That's the whole point of a Foundation Review. 30 minutes, on Zoom, one-on-one with Andrew — your 3–5 highest-leverage moves, each one quantified in annual dollars.

What it is

  • 30 minutes, on Zoom, one-on-one with Andrew
  • Your 3–5 highest-leverage moves, walked through
  • Each move quantified in annual dollars
  • You leave with a prioritized punch list for this quarter

What it isn't

  • Not a sales pitch
  • Not a webinar or a group call
  • Not a product push — Good Deals doesn't sell products
  • Not a commitment to hire us
Book Your Foundation Review →

Worst case: you walk away with a couple of five-figure tax-saving ideas. Best case: we build something that compounds for the rest of your life.