CROSSPOINT PLANNING: RETIREMENT ON YOUR TERMS
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You Built The Wealth. We Help You Actually Enjoy It
Fee-only financial planning for the critical years leading up to and into retirement.
The decisions you make in the "Retirement Risk Window" decide everything that follows. This is why we exist. 
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We want you to move forward with absolute clarity and peace of mind.
We believe you deserve total confidence and peace of mind in how that plan is delivered. For us, that means complete transparency, zero jargon, and taking the time to educate you every step of the way.
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​We get it because we’re right there with you—navigating real life, just like you.
Meet The Team

Retirement's Approaching (Or Already Here)
The strategies that built your wealth won't protect it. Retirement runs on a completely different playbook.
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How do I turn savings into income I can't outlive?
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How do I reduce taxes in retirement instead of leaving the IRS a tip?
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How do I protect what I've built and make sure it reaches the right people?
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Are my investments built for retirement, or still positioned for accumulation?
How We Help
The Freedom to Live Framework
Taxes, income, legacy, and investments don't work in isolation — and your plan shouldn't either. We build them as one coordinated strategy.
See How It Works
Investments Taxes Legacy $ Income

Why Choose Crosspoint?

How Our Retirement-Focused Approach Compares to Industry Peers

Crosspoint Planning

Other Advisors

Retirement Projections

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Custom Investment Strategy

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Tax Loss Harvesting & Rebalancing

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Strategic Withdrawal Sequencing

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Tax Bracket Management In Retirement

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Medicare and Healthcare Planning

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Estate and Legacy Planning

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Social Security Optimization

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Advice Across All Assets—Not Just What We Manage

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Download our Retirement Playbook→​

OUR GOAL

To help you live your best life in retirement
​Your 'why' is our compass. Together, we’ll craft a financial plan that's tailored to your life, your goals, and your values.​
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Meet With Us

First Let's

Discover
You’ll schedule an introductory call with our team to see what working with Crosspoint looks like.

Now let's WORK

The Crosspoint Way
We use a structured, collaborative process to build a plan that unlocks true financial freedom.

We Provide

Continuous Service
 Our partnership doesn’t end with a plan. We continually evaluate your needs to maximize and protect what matters most to you.
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Common Questions
Answer

We work primarily with successful prospective and current retirees navigating the most important years surrounding retirement — typically those within 5 to 7 years on either side of leaving full-time employment, no matter the age.

Our clients tend to have built meaningful wealth ($2 million+) through decades of disciplined work and saving, and are now looking for clarity and confidence as they transition into the next chapter of life.

We work primarily with successful prospective and current retirees navigating the most important years surrounding retirement — typically those within 5 to 7 years on either side of leaving full-time employment, no matter the age.

Our clients tend to have built meaningful wealth ($2 million+) through decades of disciplined work and saving, and are now looking for clarity and confidence as they transition into the next chapter of life.

The retirement risk window is the 5 to 7 years before and after retirement — the period when investment risk, financial decisions, and major life transitions have the greatest long-term impact on your financial future.

Decisions made during this window can shape the rest of your retirement, which is why we focus our planning specifically on helping clients navigate it with clarity and confidence.

This is one of the most common — and most important — questions we help clients answer. Confidence to step away from work doesn't come from a number alone; it comes from understanding how your resources, spending, and goals fit together.

We help you organize the financial complexity, stress-test your plan against real-world scenarios, and build a personalized roadmap so you can make this decision with clarity rather than guesswork.

Determining a safe, sustainable spending level is central to our planning process. We look at your full financial picture — including income sources, taxes, investment risk, and the lifestyle you want to live — to build a spending strategy you can rely on.

Just as importantly, we help many clients overcome the emotional hurdle of actually spending and enjoying the wealth they've worked so hard to build.

Market downturns early in retirement are one of the biggest risks pre-retirees face — a concept known as sequence-of-returns risk. A poorly timed drop can permanently impair a portfolio if the plan isn't built to absorb it.

We design portfolios and withdrawal strategies specifically to address this risk, combining our proprietary investment approach with planning safeguards so that early market volatility doesn't derail your long-term retirement.

Our process starts with an introductory phone call to learn more about you and your values. By understanding what matters most to you, not just the numbers, we can start building the lifestyle and legacy you want to create.

From there, we align your resources with your goals to build a clear, personalized roadmap. We address the emotional realities of retirement alongside the financial ones, and we meet regularly to update the plan as life and markets evolve. Get started here.


​Retirement Education
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Why Retirement Readiness Is About Much More Than Money
Why stressing over ‘Do I Have Enough’ leaves retirees vulnerable on health, identity, and social connection.
Read More
A 401(k) Is a Savings Tool, Not a Retirement Plan
By: Andrew Lancaster, ​CFP® / July 28th, 2026

The Scarcity Mindset is Costing You The Best Years of Your Retirement 
By: Andrew Lancaster, ​CFP® / April 14th, 2026

Statistically, Your Investments Are Probably Too Conservative
By: Andrew Lancaster, ​CFP® / February 24th, 2026

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© COPYRIGHT 2026. ALL RIGHTS RESERVED.
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P: (415) 291-2911
Crosspoint Capital Management, LLC dba Crosspoint Planning (“Crosspoint”) is a CA-registered investment adviser. Registration does not imply a certain level of skill or training. The content on this website is for informational purposes only and should not be construed as personalized investment, tax, or legal advice. Advisory services are offered only through a written agreement with Crosspoint Capital Management, LLC.
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All investments involve risk, including the potential loss of principal. Past performance does not guarantee future results. Crosspoint may provide guidance on financial planning concepts, but does not offer legal or tax advice. Clients should consult their own legal or tax professionals for advice specific to their situation. 
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