Your move to Costa Rica deserves a real plan, not another Google search.
A structured path from “we're thinking about it” to “we're living it”, built by a CFP whose family made the transition themselves.
Last updated March 2026
Why most families stay stuck
You've read the blog posts. You've joined the Facebook groups. You've started three spreadsheets and finished none of them.
You're not stuck because you lack information. You're stuck because the information is scattered, contradictory, and none of it was written for your situation.
Meanwhile, your current financial advisor has never dealt with a client leaving the country. Your accountant doesn't understand cross-border tax. And every “expat expert” online is selling a lifestyle, not a financial plan.
You need a process, not more content. And you need it from someone who's actually done this.
We didn't just plan this. We lived it.
My family made this transition on a real budget, with real kids, and real financial constraints. Not from a position of wealth. From a position of clarity.
That experience, combined with my CFP® certification, is the foundation of everything we do here.
Every recommendation comes from someone who sat where you're sitting and figured it out.
90 Days
Family Relocation
CFP®
Certified Financial Planner
100%
Cross-Border Focus
Where are you in your journey?
Three paths. Each one meets you where you are.
Find your fit
Three options. One goal.
Each option is designed around where you are in your journey.
For families with specific questions
$800
Strategy Session
Get real answers before you commit.
A focused 2-hour session with Brennan to address your specific cross-border financial questions. No generic advice — just clarity on what matters to you.
- 2-hour deep-dive session with Brennan
- Focused on your specific cross-border financial questions
- Personalized analysis, not generic advice
- Clear next steps documented after the session
Your $800 is credited toward the Cross-Border Blueprint if you decide to move forward.
For families ready to move
$7,500
Cross-Border Financial Blueprint
Move with a plan, not a prayer.
In 90 days, you'll have a complete financial architecture for your relocation — 12 deliverables covering every dimension of your cross-border financial life.
3-phase advisory process
- Phase 1: DIAGNOSE (Weeks 1–3)
We map your complete financial picture — income, assets, liabilities, tax situation, retirement accounts, real estate, insurance. - Phase 2: ARCHITECT (Weeks 3–8)
We build the financial plan for your move — investment repositioning, tax transition strategy, and everything sequenced in the right order. - Phase 3: EXECUTE (Weeks 8–12+)
We put the plan into action — sequenced execution calendar, pre-departure checklist, post-arrival financial setup, ongoing check-ins. Complete Architecture Guarantee kicks in at day 90.
12 deliverables included
- Dual-country tax transition strategy
- Investment repositioning plan
- Healthcare coverage map (both countries)
- Account migration sequencing
- Social Security & Medicare optimization
- Complete action plan with execution timeline
- Vetted cross-border professional network
- Ongoing advisory access through the transition
$18,250+ compared to sourcing each deliverable separately from a CPA, estate attorney, and financial advisors. 6–10 sessions over 90 days plus behind-the-scenes work.
Complete Architecture Guarantee: If after 90 days you don't have a complete plan, I keep working at no additional cost until you do.
Subject to engagement agreement terms.
For families with $500K+ in investable assets who have decided to move.
For families who want ongoing support
Starting at 1%
Investment Management
Your finances managed across borders.
Ongoing investment management and financial planning for families living cross-border. We manage your portfolio with the same cross-border expertise that built your Blueprint.
- Cross-border portfolio management
- Tax-aware investment positioning
- Ongoing financial planning and check-ins
- Coordination with your CPA, attorney, and local advisors
- Proactive adjustments as tax laws and your life evolve
Ongoing financial planning is included for clients with $1M or more in assets under management.
Most clients start with a Blueprint before transitioning to ongoing management.
You'll know exactly how these work in your new country
Your taxes in both countries
Your investments during the move
Your healthcare from day one
Your kids’ schools
Your money in and out
Your will and trust across borders
Your insurance coverage
Your retirement income abroad
Your property in both countries
Your visa and residency
Not ready for a call? Start here.
Take our 5-minute Readiness Quiz and get a personalized assessment of where you stand, plus a checklist of what to do next.
Questions we hear often
The Strategy Session is a great starting point. In two hours, we’ll dig into your specific questions and give you real answers — not generic advice. You’ll walk away knowing whether the move makes financial sense for your family.
12 deliverables over 90 days: dual-country tax strategy, investment repositioning plan, healthcare coverage map, account migration sequencing, Social Security and Medicare optimization, a complete action plan, and access to our vetted professional network. Plus 6–10 sessions with Brennan and behind-the-scenes work between sessions.
Yes. If you start with a Strategy Session and decide to move forward with the full Blueprint, your $800 is applied toward the $7,500 fee.
If after 90 days you don’t have a complete cross-border financial plan, I keep working at no additional cost until you do. You’re paying for the outcome, not the hours. See engagement agreement for full terms.
Not necessarily. Many clients keep their existing advisor while working with us on cross-border planning. We’re happy to coordinate.
All meetings are virtual via Zoom. We’re flexible across U.S. and Costa Rica time zones. Most clients meet monthly during active transition phases and quarterly once settled.
Families with $500K or more in investable assets who have decided to relocate to Costa Rica. If you’re still in the decision phase, start with a Strategy Session.
What your life looks like after
You land in Costa Rica knowing your taxes are handled, your investments are positioned, and your healthcare is covered from day one.
Your kids are enrolled. Your accounts are where they need to be. Nothing is dangling.
You stop carrying your financial life in your head. It runs quietly in the background, and you get to actually enjoy the life you moved here for.
The first step is a conversation.
No pitch, no pressure. Just a conversation about where you are and where you want to be.