Wealth strategy that meets tax reality
For pre-retirees, families inheriting wealth, and residents of Continuing Care Retirement Communities. We integrate portfolio strategy with tax and lifestyle reality, simulate scenarios in real time, and coordinate directly with your CPA. Portfolios are managed by Farther's investment team.
When planning matters most
The transition years carry the most tax weight and the most irreversible decisions. Our practice concentrates on the moments where getting the plan right matters most.
- Retirement transitions
- Individuals inheriting wealth
- Continuing Care Retirement Community (CCRC) residents
- Business owner saving strategies
Four services, one integrated plan
Proactive tax planning
Third-party review of your tax returns, Roth conversion analysis, and tax letters prepared for your accountant. The goal is to maximize after-tax wealth every year and avoid the end-of-year surprises that catch most households off guard.
Collaborative financial planning
We build your financial plan on-screen alongside you, linking your portfolio directly to your tax reality and lifestyle expenses. You see how every decision affects your long-term goals in real time, not months later in a report.
Behavioral risk alignment
We measure your personal risk tolerance and align it directly with your portfolio allocation, so you can hold your strategy with confidence during market volatility rather than reacting to headlines. Take the risk assessment: https://pro.riskalyze.com/embed/423f5bab8785e102ca3b
Multi-generational wealth transfer
We advise across your entire family tree, from grandparents to great-grandchildren. Your legacy stays preserved, organized, and efficiently transitioned to the next generation, with estate documents and beneficiary structures reviewed as things change.
What working with us looks like
STEP 1
Initial consultation
Discuss your financial ambitions and determine exactly how our approach helps you achieve them.
STEP 2
Information gathering
Share your financial data so we can identify specific opportunities to optimize your wealth.
STEP 3
Strategy proposal
Review a precise, actionable plan built around how you actually want to live.
STEP 4
Implementation
We execute your strategy, establishing a clear view of your complete financial life in one place.
WINTER
December – February
Execute year-end tax-loss harvesting to lock in tax benefits
Finalize Roth conversion strategies
Deliver a summary tax letter for your records
SPRING
March – May
Review filed tax returns
Provide a detailed tax observation report
Request fresh financial data to align your plan with your current life
SUMMER
June – August
Update your financial plan
Review estate and beneficiary designations (even years) to protect your legacy
Evaluate insurance coverage (odd years)
FALL
September – November
Prepare estimated tax projections so you know exactly what to expect
Adjust your financial plan for the year ahead
Proactive review meetings
Tax optimization and Roth conversion analysis
Professional portfolio management
Monthly client newsletter
Wondering how this applies to your situation?
Getting to know Olsen & Little Team
The Olsen & Little Team builds financial plans on-screen, alongside you, that link your investments to your tax situation and lifestyle. Robert Olsen and Brayden Little serve individuals and families entering the transition years, when tax decisions carry the most weight. The Olsen & Little Team provides integrated wealth management for families, individuals, and business owners. We deliver coordinated guidance so investment strategy, long-range planning, and tax strategy work together rather than in parallel silos. Robert Olsen brings two decades of experience to this approach. After surviving a rare cancer in 2013, he learned firsthand that true financial security means having the freedom to focus on your family when the unexpected happens. Brayden Little, a CFP® professional, anchors the team's comprehensive tax planning, cashflow management, and long-range retirement forecasting. Since 2018, he has guided more than 200 families through complex financial decisions. The practice has grown entirely through client referrals.
Our team
Frequently asked questions
Do you prepare our taxes?+−
We provide deep tax planning and strategy, not tax preparation. We simulate tax scenarios and work directly with your CPA to implement the strategy accurately.
Do I need to be local to work with you?+−
No. We operate a national practice and serve clients across the country via virtual meetings, so you receive guidance wherever you are located
How do you manage investments?+−
We use Farther's institutional investment team to deliver personalized investment strategies. That allows us to dedicate our time to your integrated financial and tax planning.
Your all-in-one financial ecosystem
Our Intelligent Wealth Platform brings your financial world into a trusted, single-view, with technology natively built to avoid the limitations of legacy wealth management institutions. Your information and accounts are protected with the highest levels of data security and compliance.
Deep Integration With
Pershing, Apex, Schwab, Fidelity, and 90+ additional custodians
Complete Financial Operation System
AWS Security & Privacy and Plaid Connectivity
Your full wealth picture, in one place
Effortless control+−
Gain a comprehensive view of your financial landscape — banking, investments, lending, insurance, and more — all organized on one platform.
Streamlined collaboration+−
Share specific financial data with your CPA, attorney, and family members — promoting transparent and collaborative wealth management.
Centralized document hub+−
Store every financial document in one organized, secure, and easily accessible location.
Cash management+−
Our intelligent system continuously monitors your bank accounts — maintaining your liquidity, while ensuring excess cash is efficiently invested and working to increase your wealth.
Save time and hassle+−
Find answers and perform financial tasks swiftly with just a few clicks, from anywhere, at any time.
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