A STRATEGIC TAX RELATIONSHIP—ALL YEAR LONG
THE TAX PREPARATIONSHIP™
While an ongoing, long-term, comprehensive approach is often ideal, not everyone is ready to make that full commitment. The Tax Preparationship™ was created as a standalone service for ongoing, current-year tax strategy and preparation—without the requirement of a full advisory engagement.
Tax preparation shouldn’t be a once-a-year paperwork event; it should be an ongoing relationship. A Tax Preparationship™.
Traditional tax prep focuses on what already happened, often rushing through forms and deadlines without meaningful strategy. A Tax Preparationship™ redefines the experience by offering proactive guidance throughout the year—anticipating opportunities, planning ahead, and refining your tax approach as life evolves. Rather than a reactive checklist each spring, you gain a trusted partner focused on clarity, connection, and long-term results.
A TAX PREPARATIONSHIP™ INCLUDES:
ANNUAL FEDERAL & STATE TAX PREPARATION
Accurate, timely filing with careful consideration of deductions, credits, and planning opportunities designed to minimize your overall tax burden.
MID-YEAR STRATEGY REVIEWS
Proactive check-ins to adjust withholding, evaluate projected results, and implement strategies before year-end.
COMPLEX CURRENT-YEAR EQUITY COMPENSATION & CAPITAL GAINS PLANNING
Guidance on RSUs, ISOs, ESPPs, and investment sales to optimize timing, manage tax impact, and support long-term outcomes.
CHARITABLE & GIFT PLANNING COORDINATION
Thoughtful support in structuring philanthropic giving and wealth transfers to align tax efficiency with personal and family goals.
ON-DEMAND TAX GUIDANCE
Direct access to your advisor when questions arise, helping you make confident, well-informed decisions throughout the year.
WHO IS A TAX PREPARATIONSHIP™ RIGHT FOR?
Those who want proactive, year-round tax support—not just a seasonal filing event. Ideal for:
- Professionals with equity compensation — including RSUs, ISOs, ESPPs, and other similarly complex planning considerations.
- Business owners — navigating both personal and business tax decisions throughout the year.
- Individuals or families with evolving financial lives — who value thoughtful guidance as circumstances change.
- Anyone who wants an ongoing tax partner — with a preference for clarity, communication, and strategy all year long.
WHO IT’S NOT FOR
Tax Preparationship™ is focused on current-year tax strategy and decision-making. It is not intended for long-term or multi-year financial planning needs such as retirement strategy, investment management, or broader wealth planning. Those goals are best supported through a comprehensive advisory relationship that integrate your full financial picture beyond the scope of the current tax year. To learn more about an ongoing, comprehensive advisory relationship see Our Process page.
EXPERIENCE THE FIVE8 DIFFERENCE
If you’d like to explore whether our approach is a fit, schedule a complimentary discovery call. We’ll learn about your priorities and explain how our planning process would apply to your situation.
HOW THE TAX PREPARATIONSHIP™ PROCESS WORKS
The process is designed to create clarity, consistency, and proactive support throughout the entire year—not just during tax season.
PRICING BASED ON YOUR PREVIOUS TAX RETURN
The first year’s fee is based on the complexity of your most recent tax return and any known changes for the current year. This ensures pricing is fair, transparent, and reflective of the work involved.
ANNUAL ENGAGEMENT LETTER
Each spring, you’ll receive an engagement letter confirming your commitment for the upcoming tax season and outlining the scope of current-year tax planning. This keeps expectations clear and aligned from the start.
TECH-FORWARD ONBOARDING & DATA COLLECTION
Secure, modern tools are used to streamline document delivery, questionnaires, signatures, and communication—making the process simple and efficient from anywhere. While the experience is digital-first for convenience, accommodations are available for clients who prefer to drop off paper documents or sign in person, ensuring the process feels comfortable and accessible.
MID-YEAR STRATEGY CHECK-IN
After filing season concludes, we will schedule a mid-year review to project your current-year tax outlook and identify planning opportunities or course corrections before year-end. This reduces guesswork and helps prevent unexpected outcomes.
ADDITIONAL SUPPORT FOR DYNAMIC INCOME SITUATIONS
For those with equity compensation, irregular income, or other complex planning needs, the relationship can include additional mid-year projections as appropriate. Pricing is adjusted accordingly to support the level of complexity and ongoing guidance required.
TAX PREPARATIONSHIP™ PRICING
As a standalone engagement, Tax Preparationship™ begins at $1,200 for clients with W-2 income and passive investment income only. For individuals or businesses with additional complexity—such as rental properties, business ownership or self-employment, equity compensation, multiple state filings, or other advanced planning considerations—pricing is adjusted to reflect the scope and intricacy of the work involved.
Pricing is discussed transparently upfront, barring any material changes, and a formal quote is provided after reviewing your documents and confirming the full scope of your tax situation.
LET’S CONNECT
If you’d like to explore whether Five8 is the right fit, we invite you to schedule a complimentary discovery meeting using the calendar below. Prefer to start with a message instead? Submit the contact form, and someone from our team will be in touch soon to continue the conversation.