What is the difference between Tax Preparation and Business Advisory?

Tax preparation is a historical record of what happened last year. Business Advisory Services (BAS) is a year-round partnership focused on the future. BAS includes your annual tax filings, but adds tax projections, payroll strategy, and ongoing consulting to ensure you pay the least amount of tax legally possible.

Is Business Advisory designed for S Corps or Solo Entrepreneurs?

Yes. BAS is specifically designed for solo operators and small ownership groups, especially those who have elected S Corporation status. It is for business owners who want proactive planning rather than annual tax surprises.

How does WCG’s Business Advisory differ from the Tax Patrol service?

Tax Patrol is a lighter compliance cadence for simpler situations. Business Advisory includes deeper planning, a higher meeting frequency (approx. 8 touchpoints/year), and robust tax reduction strategies. If you need us to “watch the store” while you run the business, BAS is the right fit.

What is included in the Vail tier?

Vail is our standard comprehensive flagship platform. It includes your S Corp tax return (Form 1120S), your individual return (Form 1040), household tax projections, reasonable salary optimization, and scheduled advisory meetings throughout the year.

When should I choose Telluride over Vail?

For skiing or for advisory? Telluride is the right choice when state taxes get messy. If you want to utilize the Pass-Through Entity Tax (PTET) deduction, or if you operate in high-complexity states like California or New York, Telluride provides the necessary business-level tax projections that Vail does not.

Do I need a separate Business Entity Tax Projection?

Definite maybe. Texas businesses often don’t need one (no state income tax). California businesses almost always do (high franchise taxes). This is the primary fork in the road between our Vail and Telluride tiers.

Is payroll processing included in the fee?

Payroll strategy (determining your salary) is included. Actual payroll processing is an optional add-on. Many clients prefer to DIY their payroll using tools like Gusto or ADP, while others prefer to hand it off to us completely. We have Payroll Quick Launch to help out as well.

How often will I meet with my CPA tax team?

You can expect roughly eight touchpoints a year. This includes pre-planning sessions, tax projection reviews, year-end wrap-ups, and tax return reviews. Plus, you have access to Periodic Scheduled Quick Chats for ad-hoc questions when life happens.

Can I customize my Business Advisory Services platform?

Yes. While Vail and Telluride are our standard “chassis,” they can be fine-tuned. We can add or remove specific services to fit your needs without forcing you into a fully custom Aspen engagement.

Does WCG provide financial investment advice?

Nope. We stay firmly in the tax planning lane. However, we coordinate directly with your financial advisor to ensure our tax strategies work in harmony with your investment goals, rather than fighting against them.

Aspen Tax Strategy Series

Posted Friday, April 24, 2026

Table Of Contents

Key Takeaways

Start With the Goal, Not the Tax Bill: Good planning begins with what you’re trying to build not how fast you can slash taxes. The tax tail should never wag the investment dog. Building wealth is your #1 priority- not the only one, the number one.
Most Strategies Fail the Reality Filter: Session 1 and 2 are about eliminating what won’t work based on your cash, time, and risk tolerance so you don’t waste energy chasing shiny but impractical ideas. Not all that glitters is gold, right?
Every Strategy Requires Cash, Effort, and Risk: The “3-legged stool” is unavoidable. If a strategy doesn’t fit your capital, time commitment, or risk appetite, it’s not a real option.
Promoter Math Gets Replaced With Real Math: By Session 3, everything is modeled with actual numbers such as initial cash outlays and subsequent tax savings so decisions are grounded in reality, not sales pitches. Long-term outcomes need to be discussed, and if necessary, modeled into an IRR analysis.
Tax Savings Today Can Create Friction Tomorrow: Accelerated deductions, depreciation, and losses often come with recapture, exit challenges, or reduced future benefits, so the future you tax impact matters just as much as year-one savings.
The End Goal Is a Clear, Executable Plan (or Confident Inaction): You either walk away with a detailed execution blueprint, or the confidence that you’re already doing the right things and can ignore tax FOMO.

Most high earners have heard the pitch. Few have sat down with someone willing to stress-test it against their actual numbers, risk tolerance, and liquidity before recommending anything. Far too often recommendations are made without any real assessment of your situation, and one size does not fit all. The Aspen Tax Strategy Series is three sessions of structured work designed to do exactly that, taking you from financial snapshot to execution blueprint with the math and the honest guardrails to back it up.

Following our visual below is a pulled curtain on session specifics and checklists.

Aspen Tax Strategy Series

Not every tax strategy belongs on your tax return. The Aspen Tax Strategy Series is a structured three-session engagement designed to cut through the noise, pressure-test your options, and deliver a blueprint built around your actual numbers, risk tolerance, and wealth goals.

Series Fee
$1,800
All three sessions

Sessions
3
Foundation, exploration, blueprint

Deliverable
1
Execution

Session 1

Foundation

Map Your Wealth Trajectory
Diagnose Your Taxable Surface
Analyze All Income Sources & Structures
Assess Liquidity & Leverage Limits
Pressure-Test Material Participation
Define Financial Risk Tolerance

Session 2

Strategy Exploration

Tie Loose Ends From Session 1
Refine Constraints & Reality Filters
Mark Tax Strategy Must Haves
Eliminate Poor-Fit Strategies
Deep Dive Into 2-3 Tax Strategies
Evaluate Cash, Effort & Risk Tradeoffs

Session 3

Math & The Blueprint

Model 2-3 Surviving Strategies in Real-Time
Map Capital Requirements & Cash Flow
Analyze Cashless Tax Savings Ratio
Calculate First-Year Cash-on-Cash (CoC) Return
Forecast 5-10 Year Exit & Recapture Impact
Deliver Your Execution Blueprint

Add-On

Scenario Tax Plan & IRR Modeling

Is our Aspen Engagement right for you? Learn how we map the taxable surface, pressure-test the path, and build a strategy that works. Schedule a kickoff conversation when you’re ready.

Aspen Tax Strategy Series

Session 1: Foundation, Footprint & Ambition (75 minutes)

Most tax strategy conversations start with the wrong question- “how do I pay less?” We start with a better one- “what are you actually trying to build?”

Session 1 is a structured teardown of your entire financial picture including income, entities, real estate, liquidity, and risk tolerance. We need to know exactly what’s viable before we waste a single minute exploring strategies that were never going to work for you.

Pre-Session Prep: We analyze your tax returns, income drivers, and life events ahead of time to identify missed opportunities.
Wealth Ambitions First: We start by defining what “winning” actually looks like because the tax tail should never wag the investment dog. Woof.
The Footprint Teardown: We strip your current tax setup down to the studs to see exactly what you are already doing to reduce taxes, and what you are leaving on the table.
Income & Entity Analysis: A thorough review of your current business entities, investment and real estate income, W-2s, K-1s, expected capital gains, deferred compensation, and anticipated spikes like RSUs, ISOs, or other equity compensation.
Capital & Leverage Appetite: We assess your availability of cash and your willingness to use debt, which are the primary engines that make advanced tax strategies work.
Material Participation Reality Check: We evaluate your actual capacity to meet IRS material participation rules to ensure your deductions won’t get trapped by the passive activity rules.
Risk Tolerance Assessment: We define your true tolerance for financial risk. We don’t do “promoter math”; we establish what is legally and practically viable for your specific reality.

What remains after Session 1 is a short, honest list of strategies that actually fit your cash, your time, and your risk profile. Your homework is to review WCG’s advanced tax strategy materials, rank your top two or three based on genuine interest and feasibility, and come back ready to defend your choices. Session 2 is where that list gets stress-tested, and where the promoter math gets replaced with real math.

Session 1 Checklists

We do not show up to Session 1 with a blank notepad and good intentions. Before we ever meet, your tax strategist has reviewed your returns, identified your top income drivers, flagged missed opportunities, and mapped your AGI trend. The checklist below is what makes that possible. Your job is to get us the documents and complete the questionnaire at least 48 hours before we meet. Our job is to show up ready to work. The more complete your submission, the more productive Session 1 becomes, and the sharper the strategy that comes out the other side.

Pre Session Checklist

Required Documents (at least 48 hours prior):

Last 2 years of complete tax returns (all federal + state)
Current year-to-date paystubs (W-2 earners)
Expected full-year-to-date profit and loss (business owners)
Most recent K-1s (if applicable)
Summary of real estate holdings (address, ownership %, use, expected net profit/loss for each)
Investment account snapshot (taxable + retirement)

Client Questionnaire (must be completed):

Any major life changes (marriage/divorce, new child, job change / spouse employment change, relocation)
Any anticipated events (large bonus / equity vesting, business sale or acquisition, property purchase or sale)
Current cash availability (rough ranges are fine) including lines of credit
Self-identified risk tolerance (Low / Moderate / Aggressive)

Before We Meet (Tax Strategist):

Review of tax returns (identify top 3 income drivers, flag missed opportunities, note AGI trend)
Review of all current year income sources
Review Client Questionnaire

Session Checklist

Session 1 Objectives

Session 1 isn’t about throwing ideas at the wall- it’s about eliminating what won’t work so we can focus only on what will.
Establish a clear tax baseline and decision framework for Sessions 2, 3 and 4.

Income & Tax Profile

Review all income sources (W-2, business, investments, real estate)
Identify marginal tax bracket (and depth) and state tax exposure
Assess income consistency (stable vs. variable, future spikes)
Understand depth of current tax strategies (401k, QBID, PTET / SALT)

Business Profile (if applicable)

Review current entity structures including ownership arrangements
Identify structural inefficiencies or missed elections
Assess depth of current tax strategies (APlan, automobiles, paying spouse / children, QBID, PTET / SALT)
Review 1-2 year goals and 5-7 year goals, including exit strategy

Real Estate Profile (if applicable)

Evaluate ownership structure (individual, spouse, HoldCo, PropCo, OpCo, trusts)
Review real estate holdings and usage (short-term vs long-term, commercial)
Evaluate level of participation and time involvement for each
Determine viability of strategies like cost segregation, REPS and related strategies
Discuss long-term plans, including potential liquidation or personal-use conversions

Cash Flow & Liquidity

Assess available cash and access to capital including lines of credit
Evaluate ability to fund and sustain tax strategies
Identify any constraints that limit planning options

Risk Tolerance Alignment

Define comfort level (Low / Moderate / Aggressive)
Discuss trade-offs between savings, complexity, and redemption exposure (financial risk)

Baseline Strategies

Review current 401k contributions and Roth 401k options
Evaluate use of Health Savings Account (HSA)
Identify opportunities for Roth conversions in low-income years
Assess Backdoor Roth IRA eligibility and execution (if applicable)

Baseline Business Owner Strategies (if applicable)

Evaluate use of Accountable Plan reimbursements
Review S Corp salary structure and QBID optimization
Review retirement plan options (Solo 401k, Cash Balance) for contribution optimization
Assess feasibility of adding children to payroll
Evaluate Augusta Rule (IRC Section 280A(g)) opportunities and compliance requirements

Reality Filter & Strategy Guardrails

Identify commonly discussed or promoted strategies
Eliminate approaches that lack economic substance
Narrow focus to strategies aligned with your time, cash, and risk profile

Session Next Steps / Homework

Review WCG’s advanced tax strategies and niche asset materials (links provided)
Rank your top 2-3 strategies based on personal interest and feasibility (appetite / tolerance)
Note any strategies you want to explore or eliminate based on Session 1’s reality filter
Re-confirm any missing documents or questionnaire items not submitted prior to Session 1
WCG will provide a brief Session 1 summary noting your tax footprint, identified opportunities, and confirmed guardrails / limitations.

Tax Patrol Sample Proposal

Explore our comprehensive tax patrol services and personalized consulting sample offer!

Advisory Sample Proposal

See our comprehensive tax advisory services and tailored consulting sample offer!

Transparent Fee Structure

Read about our philosophy on fees, how they change, and what influences your tax prep costs.

Session 2: Strategy Exploration

Oftentimes tax strategy is defined in the negative- you remove everything that won’t work, and you’re left with the “maybe so’s.” Session 2 is where that elimination happens. Your shortlist gets stress-tested against the 3-Legged Stool, the Economic Substance Doctrine, and the Financial Tattoo test. What survives is worth modeling. The promoter math gets replaced with real math. What survives is worth modeling. Everything else gets cut.

3-Legged Stool Reminder: Every strategy requires some combination of cash (capital or debt), effort (time and documentation), and risk (financial and audit exposure).
The Effort Spectrum: Some strategies require little effort (retirement contributions), while others demand significant, documentable involvement (real estate, equipment leasing, operating businesses).
Excess Business Loss (EBL) Buzzkill: Tax strategies can be capped against non-business income such as high W-2 earnings. Excessive business losses above IRS thresholds ($512,000 MFJ for the 2026 tax year) are carried forward, not immediately usable.
Economic Substance Doctrine: Codified in IRC Section 7701(o), your money must be at risk, and the deal must have commercial purpose. If the only mathematical way an investment makes sense is the tax deduction, it is likely an abusive tax shelter.
The “Reverse Marginal Bracket” Trap: Tax strategy is about optimizing rates, not just minimizing income. If we use aggressive deductions to drive your taxable income down into the 10% or 12% bracket, your last dollar of deduction loses its power.
First-Year “Sugar High”: Advanced strategies rely heavily on Section 179 or Bonus Depreciation. It is critical to understand the difference, and how that difference impacts you today and tomorrow. Oh, and many states decouple from federal bonus depreciation.
Financial Tattoo (Exit Risk): A bad investment made for a tax deduction remains a bad investment long after the tax benefit fades. Many advanced strategies (syndicates, captives, DSTs) are incredibly difficult to redeem or sell. They are like a tattoo- make sure you’ll still like it in five years.
Strategy Narrowing: We cut through the noise and focus only on the strategies that actually fit, and eliminate / postpone everything else before it wastes your time or capital.
WCG’s Role: We are agnostic. We don’t promote products or sell pitch decks. We stress-test the math to see if a strategy can survive IRS sunlight and actually build your long-term wealth.

Before Session 3, we close the loop again. WCG delivers a brief Session 2 summary confirming the surviving strategies, the key assumptions we’ll model, and any outstanding data needed to run the numbers. If Session 1 set the playing field and Session 2 cleared the bench, Session 3 is game time. Come ready to model each tax strategy (and perhaps commit).

Session 2 Checklists

Session 1 gave us the map. Session 2 is where we start narrowing the route. This is an exploration session, not a commitment session, so come in with curiosity rather than conclusions. We will tie out any loose ends from Session 1, stress-test your top strategy candidates against the three-legged stool of cash, time, and risk, and eliminate anything that looked good on paper but does not survive contact with your actual situation.

The two or three strategies that make it through this filter are the ones worth modeling in Session 3. Everything else gets set aside for now but is not dismissed. In three to five years, your income, liquidity, and risk tolerance may look very different, and some of those strategies have a way of popping back up as both feasible and desirable.

Session 2 Objectives

Session 2 is about exploring and comparing—not committing
Identify which strategies are worth deeper modeling in Session 3
Align potential strategies with your cash, time, and risk constraints

Tie-Out From Session 1

Confirm Session 1 summary (tax footprint, guardrails, limitations)
Address any missing documents or open questions
Reconfirm income expectations and any near-term changes

Strategy Prioritization

Review top 2–3 preferred strategies from assigned materials
Discuss why each strategy is appealing (tax savings, cash flow, long-term growth)
Eliminate strategies that no longer fit based on Session 1 guardrails and constraints

3-Legged Stool Evaluation (Per Strategy)

Evaluate required cash (capital investment, debt, liquidity impact)
Evaluate required effort (time, material participation, documentation)
Evaluate risk (financial exposure, audit scrutiny, complexity)

Strategy Deep Dive (2–3 Core Strategies)

Outline how each strategy works in your specific situation
Identify expected tax impact (high-level estimates, not modeled yet)
Review operational requirements and ongoing responsibilities
Identify key dependencies (timing, income levels, entity structure)

Structural & Tax Constraints

Evaluate impact of Excess Business Loss (EBL) limitations
Assess interaction with current income (W-2 vs business vs passive)
Identify any structural changes required (entities, elections, grouping)
Consider state tax implications (PTET, residency, apportionment)

Risk & Exit Considerations

Evaluate liquidity and ability to exit or unwind the strategy
Identify potential recapture or future tax consequences
Discuss long-term viability beyond initial tax benefit
Eliminate strategies that create unacceptable long-term financial or exit risk

Session Next Steps / Homework

Confirm the 2–3 strategies selected for Session 3 modeling
Provide any additional data needed for scenario analysis
Begin thinking through implementation timing (current year vs future year)
WCG will prepare high-level modeling assumptions for Session 3