Retire with Clarity
& Confidence.
We help high-achieving professionals and couples build retirement plans that actually work — through markets, through life, and through every season that follows.
Connecting Your Money
to What Matters Most
Our primary focus is to deliver the results that matter most to our clients — family-focused individuals and couples motivated by the opportunity to experience a retirement that's both financially secure and personally fulfilling.
Over two decades, we've consulted with thousands of aspiring retirees. Through that experience, we've identified three core outcomes that guide every plan we build.
Income Clarity
So you never wonder: "Can we afford this?" We build a reliable income floor so your lifestyle is funded — and your spending is guilt-free.
Risk Containment
So no single event can derail the plan. We stress-test your retirement against the scenarios that actually break people — not just the average ones.
Lifetime Efficiency
So more money stays where it belongs. We coordinate taxes, withdrawals, and asset location so your wealth works harder over decades.
No cost · No obligation · No sales pitch
20+
Years helping families retire with confidence
Fiduciary
Advisor
How Retirement-Ready
Are You, Really?
Most people approaching retirement have a portfolio — but not a plan. Our Retirement Readiness Scorecard evaluates your income strategy, tax exposure, healthcare plan, and risk profile to reveal exactly where you stand and what to address first.
No email required to start · Results in minutes
5 min
to know where you stand
SMART Retirement Blueprint® Assessment
Most financial plans are built around a portfolio. The SMART Retirement Blueprint® is built around your life — your vision, your income, your protection, and your legacy.
Vision & Values
Every great retirement plan begins with a clear picture of what you want your life to look like. Before any numbers are run, we guide you through a structured discovery process to define what matters most — your purpose, your relationships, your freedom, and what a truly fulfilling retirement means to you.
Secure Your Foundation
Before any investment strategy is built, the foundation must be solid. We establish an income floor through SS optimization and pension planning, ensure short-term liquidity, and protect your family through life insurance and estate coordination.
Medical & Healthcare Plan
Healthcare is consistently the most underestimated retirement expense. We plan across three stages: bridging the gap before Medicare, Medicare enrollment and plan selection, and long-term care and impairment planning.
Asset Management
Every dollar should be working the right job, in the right place, at the right time. We use a Fiscal House framework — Foundation (safety), Walls (growth and income), and Roof (long-horizon legacy assets) — with tax-efficient asset location.
Risk Management
Retirement doesn't fail on average — it fails at the extremes. We systematically identify and build guardrails around longevity risk, sequence-of-returns risk, healthcare cost escalation, spousal loss, and tax law changes.
Tax-Conscious Planning & Legacy
Taxes are the largest expense most retirees never fully plan for. We coordinate tax location, Roth conversions, RMD planning, bracket management, and tax-efficient legacy strategies so more of your wealth stays where it belongs.
From First Conversation to Confident Retirement
Vision
Map your ideal retirement outcome. Gain clarity around your specific goals and what you want your life to look like.
Assessment
Determine personal benchmarks. A detailed analysis of where you are today compared to where you want to be.
Blueprinting
Build your custom SMART Retirement Blueprint® — a comprehensive, coordinated plan built around your life.
Execution
Break ground and lay your plan foundation. Begin implementation with a focused 6-month runway and clear priorities.
"Retirement is not an end. It's the beginning of the life you've been working toward."
— Jason Rindskopf, WMCP®, RICP®
True Wealth Is More Than a Number
At Two Waters, we believe that financial planning should serve your life — not the other way around. Our Total Wealth approach addresses the four dimensions that together define a truly rich retirement.
Lifestyle-Focused Financial Plan
A comprehensive financial strategy aligned with your ideal life plan, not just your balance sheet.
Health & Wellbeing
Invest in your healthspan — strategies for prevention and protection as you age with dignity and independence.
Relationships
Prioritize the people who matter most. Your retirement plan should create space for deeper connections.
Purposeful Activity
Retirement is your opportunity to contribute, create impact, and pursue what gives your life meaning.
Jason Rindskopf
WMCP® · RICP® · Founder & Lead Advisor
Jason is the founder of Two Waters Wealth Management, author of Survive the Crash, and creator of the SMART Retirement Blueprint®. He holds the Fiduciary Standard and has spent over two decades helping families build retirement plans that actually hold up — through markets, through life changes, and through every season that follows.
Prior to founding Two Waters in 2018, Jason spent 13 years advising over 1,000 financial advisors nationwide on more than $1 billion in retirement plan assets.
Real Planning. Real Results.
The following scenarios illustrate how coordinated planning creates outcomes that no single product or strategy can achieve alone. Names and details are fictional; the planning concepts are real.
Social Security Strategy
The Social Security Bridge
Michael and Linda were ready to retire at 62, but knew that delaying Social Security until 70 would significantly increase their lifetime benefits. The challenge was funding the gap. By repositioning a portion of their savings into a structured income strategy, they created a bridge that covered their lifestyle needs for 8 years, allowing their Social Security benefit to grow by 32% and providing a much stronger foundation for the rest of retirement.
Tax Planning
The Roth Conversion Window
Tom retired at 64 with most of his savings in a traditional IRA. His advisor identified a 6-year window before Medicare surcharges and Required Minimum Distributions would push him into a higher bracket. By systematically converting a portion of his IRA to Roth each year, Tom reduced his projected lifetime tax burden by over $180,000 and left his children a tax-free inheritance.
Risk Management
Sequence-of-Returns Protection
Mark retired in early 2020, just before a significant market downturn. Because his plan included a dedicated income floor and a short-term liquidity buffer, he never had to sell investments at a loss. His long-term portfolio was left untouched and recovered fully. Without that structure, his plan would have been permanently impaired in the first year of retirement.
Healthcare Planning
Bridging the Medicare Gap
Carol retired at 60 and faced a 5-year gap before Medicare eligibility. Pre-Medicare healthcare costs can run $30,000 to $40,000 per year for early retirees. By coordinating the ACA marketplace, an HSA drawdown, and careful income management to qualify for subsidies, Carol saved over $50,000 during the bridge period.
Legacy Planning
Spend It, Give It, Leave It
George and Barbara had more than enough. Their real question wasn't how to grow their assets. It was how to allocate them intentionally. Through a structured legacy conversation, they clarified that 60% was for their lifestyle, 25% for charitable giving during their lifetime, and 15% for their children. That clarity changed everything: their plan became a tool for living their values, not just managing their money.
Income Planning
Building an Income Floor
After losing her husband, Susan found herself managing their finances alone for the first time. With one Social Security benefit gone, covering essential expenses felt uncertain. Her plan established a guaranteed income floor that covered her fixed costs regardless of market conditions. That foundation gave her the confidence to keep her growth assets invested and the peace of mind to stop worrying about the market every morning.
Ready to see what a real retirement plan looks like?
Schedule a free 30-minute call. No cost, no obligation, no sales pitch.
_178b2c07.jpg)
Survive the Crash
Recession-Proof Your Retirement: Strategies to Protect Your Wealth and Secure Your Future
In this essential guide, Jason Rindskopf shares the strategies he uses with real clients to protect retirement wealth during market downturns — so you can stop worrying about the next crash and start building a plan that holds up in any economic environment.
Jason Rindskopf
WMCP® · RICP®
Author & Retirement Strategist
Latest Insights
The Question Nobody Asks Before Retiring (And Why It's the Most Important One)
Almost everyone leads with "Do I have enough?" But that's not the first question. The one that actually matters, the one...
The 5 Medicare Enrollment Mistakes That Cost Retirees Thousands
Medicare is not automatic, and the rules around enrollment are more complicated than most people expect. Missing a deadl...
How Much Cash Should You Keep in Retirement? The Answer Might Surprise You
Most retirees either hold too much cash (costing them returns) or too little (leaving them vulnerable to sequence-of-ret...
Questions We Hear Every Day
If you've been wondering about any of these, you're in good company.
Your Retirement Deserves
More Than a Generic Plan.
Schedule a free Retirement Brainstorm Session. We'll explore your goals, identify gaps in your current plan, and show you what a SMART Retirement Blueprint® could look like for you.
No cost · No obligation · No sales pitch