Thank you for considering Woolstone Wealth Management. Starting a relationship with a financial advisor is a big step, and I understand it can feel uncertain, especially when so many advisors use confusing jargon, bury their fees, or try to sell you something the moment you walk in the door.
I want this to be different.
I spent 12 years at Vanguard and Schwab managing over $300 million across 170 households. I've seen, firsthand, what separates the families who retire with confidence from those who don't. The difference is rarely the stock market. It's having a clear plan, a tax-smart strategy, and someone who actually explains what they're doing and why.
This document walks you through exactly what happens when we work together, step by step, in plain English so there are no surprises.
What Makes Woolstone Different
Fee-Only
I am paid only by you. No commissions, referral fees, or compensation from any financial product. My only incentive is to do good work for you.
Fiduciary
I am legally and ethically required to act in your best interest at all times — not just "suitable" for your situation, but genuinely best for you.
Evidence-Based
Every recommendation is grounded in decades of academic research. I use low-cost, broadly diversified index funds because the evidence shows this approach works.
Retirement Red Zone Specialist
I work exclusively with clients aged 55–70 — the most consequential financial decade, when Social Security timing and tax strategy can mean hundreds of thousands of dollars.
Services & Fees
Option 1 — Comprehensive Wealth Management
AUM-BasedThe full-service option. I manage your investments, build and maintain your financial plan, and serve as your ongoing advisor for all retirement-related decisions.
- Tax-aware investment management
- Comprehensive retirement income planning
- Social Security and Medicare guidance
- Withdrawal sequencing strategy
- Quarterly portfolio reviews and check-ins
- Annual full plan update
- Unlimited email and phone access
1% per year on the first $2 million of investable assets
0.5% per year on assets above $2 million
Option 2 — One-Time Financial Plan
Project-BasedA comprehensive written retirement plan with no ongoing management commitment.
- Full analysis of your retirement readiness
- Social Security claiming strategy
- Tax-efficient withdrawal sequencing
- Scenario modeling (retire sooner, spend more, market downturn)
- 90-minute plan presentation meeting
$5,000 – $15,000 depending on complexity
Option 3 — Monthly Retainer
Ongoing AccessOngoing access to me for questions, guidance, and annual plan updates — without full investment management.
Best for clients who prefer to manage their own investments (a 401(k) with limited options, for example) but want a fiduciary advisor available when questions arise.
$200 – $400 per month, depending on scope
Your Onboarding Journey
Listens to your situation, explains how Woolstone works, and answers any questions. Will tell you honestly whether we're a good fit.
Show up. No preparation necessary. Ask anything.
Prepares and sends three documents via DocuSign: ADV Part 2, Investment Advisory Agreement, and Privacy Policy.
Sign account opening and transfer documents. Most everything can be handled electronically.
Sends a secure client fact-finder form and document upload portal. Reviews everything before your Discovery Meeting.
Complete the fact-finder (30–45 min) and upload your financial documents using the checklist below.
Guides a structured conversation covering your goals, fears, priorities, health picture, and what "retirement" actually means to you.
Talk openly about what matters most. There are no wrong answers in this meeting.
Builds a comprehensive financial plan with multiple scenarios — different retirement dates, spending levels, Social Security timing, and market conditions.
Nothing required. Jake may reach out with a clarifying question or two.
Walks through the complete plan in plain English — every recommendation, the reasoning behind it, and what the scenarios show.
Ask questions, push back, absorb. Jake will keep explaining until every part makes sense.
Opens custodian accounts at Schwab or Altruist, coordinates transfers from existing accounts, and implements the agreed investment strategy.
Jake handles the investment as we agree on the plan.
Quarterly portfolio reviews (30–45 min), semi-annual check-ins, and a full annual plan update every year. Available by email or phone between meetings.
Attend reviews, notify Jake of significant life changes, and stay engaged. Jake would rather hear early than late.
Document Checklist
Financial Accounts
- Investment account statements (all non-retirement brokerage accounts)
- Retirement account statements (401(k), IRA, Roth IRA, 403(b), 457, TSP)
- Most recent 401(k) or retirement plan summary
Tax Documents
- Federal tax returns — most recent 2–3 years (Form 1040 with all schedules)
- Most recent W-2s or 1099s
Social Security & Pension
- Social Security Statement from ssa.gov (log in → "My Social Security" → download)
- Pension benefit estimate letter and plan documents (if applicable)
Insurance
- Life insurance policy declarations pages
- Long-term care insurance policy (if applicable)
- Health insurance info, including Medicare enrollment
Estate & Legal Documents
- Most recent will or living will
- Trust documents (if a trust exists)
- Durable power of attorney
- Healthcare proxy or medical power of attorney
If Still Working
- Recent pay stubs (last 1–2 months)
- Employee benefits summary or open enrollment materials
Don't worry if you can't locate everything before your first meeting. Start with what you have — Jake will help identify what matters most for your situation.
Frequently Asked Questions
What to Expect in Year One
Ready to have a conversation?
Schedule a free 30-minute consultation — no obligation, no sales pitch. Just a conversation to see if working together makes sense.
Schedule Your Free Consultation