Sherpa Wealth Strategies Financial Planner in Bend, Oregon

Comprehensive wealth management

Comprehensive wealth management

An overview of the client experience

Starting Your Financial Empowerment Journey

At Sherpa Wealth Strategies, we know you need a financial planner who truly understands your unique situation. Someone who will help put you on a path toward addressing your goals, someone who will help solve your problems, and someone who will be there to educate and guide you along every step of your financial journey.

Hiring a financial planner is a like hiring a therapist. After all, you’ll need to share the intimate details of your financial life to get the best results. And though comprehensive wealth management can seem like a math problem, we’re really focused on helping you find solutions.

First – We start by really getting to know you – your goals and your dreams, what keeps you up at night and what motivates you to get up in the morning, where you are today, where you’d like to be and why.

Second – We help you implement a comprehensive financial plan, with the objective of making those goals and dreams of yours a reality.

Third – We’ll walk right by your side every step of the way, listening to you, coaching you, educating you and guiding you. When life inevitably throws you a curveball, we’ll make sure you’re prepared to hit it out of the park.

We call our process the Financial Empowerment Journey – and with it, we’ll put you on a path toward achieving all of your financial goals so you can spend more time focusing on what’s important – living your best life, enjoying your friends and family, and making a difference for the people and causes you care about.


Our Process: Part One

The Wealth Management Process

The first thing to acknowledge is that Comprehensive Wealth Management is a process, not an event. In fact, we call our process The Financial Empowerment Journey. The journey starts with a 90-minute Discovery Meeting, during which we listen deeply to understand your goals, your values and your current financial situation. We then develop a preliminary Investment Plan and the first draft of your Advanced Plan. Over the course of the next several months, we’ll meet regularly to address each key area of concern – wealth enhancement and tax minimization, wealth transfer, wealth preservation and maximizing charitable impact. Over the years we’ll continue to revisit your plan and refine our strategies moving forward.

Wealth Management Process

Our Process: Part Two

The Advanced Plan

Over the course of first several months, we’ll meet regularly to address each key area in your comprehensive wealth management plan. We focus on the key areas of concern for high-net-worth families – wealth enhancement and tax minimization, wealth preservation, wealth protection and maximizing charitable impact. Over the years we’ll continue to revisit your plan and refine our strategies moving forward.

Advanced Plan

Advanced financial planning

Wealth management topics we address

Investment Planning

  • Construction of investment portfolios to match your time horizon, risk tolerance and interests
  • Allocation of assets to appropriate account types for tax efficiency
  • Using different investment themes across multiple accounts in a household to create diversification among asset classes and investment styles
  • Regular account rebalancing
  • Careful monitoring of capital gains and losses to smooth out tax consequences

Tax Planning

  • Review of most recent tax return to understand the nature of your income
  • Identification of issues to discuss with your tax professional
  • Modeling long-term tax consequences of Roth IRAs and Roth IRA conversions
  • Modeling long-term tax consequences of Health Savings Accounts
  • Modeling tax consequences of timing Social Security benefits
  • Modeling tax consequences of Required Minimum Distributions from retirement accounts

Retirement Planning

  • How to organize your various assets and income streams into a comprehensive financial plan
  • How to allocate assets in retirements plans – IRAs, 401(k)s, 457s and 403(b)s – to provide a monthly or annual income
  • Whether and when to convert assets in a traditional IRA to a Roth IRA and other tax arbitrage strategies
  • Using life insurance to maximize after-tax income for beneficiaries
  • Strategies for beneficiary withdrawals under the SECURE Act
  • Whether to roll your employer plan into an IRA
  • When to take Social Security benefits
  • How to plan for the tax consequences of Required Minimum Distributions at age 72
  • How to choose which pension option to take, including coordination of survivor benefits with other assets
  • How to recalibrate your budget in retirement
  • Net unrealized appreciation options for employer stock

Insurance & Risk Reduction

  • Helping business owners and highly compensated executives create large life insurance cash values they can access tax-free at any time, but primarily for retirement
  • Helping young families secure term life insurance to provide the most protection for the least amount of money
  • Referring clients to professionals who can help them secure adequate health insurance or Medicare supplemental insurance
  • Helping high net worth families, especially those with large illiquid assets like ranches or closely held businesses, purchase enough permanent life insurance to provide cash to pay estate taxes or keep a business afloat after the death of the founder
  • Helping plan for long-term care expenses for themselves or their loved ones
  • Helping retirees create insured streams of income with annuities
  • Referring clients to professionals who can help them optimize their property-casualty coverage
  • Helping business partners properly fund buy-sell agreements
  • Helping business owners protect against the death of a key employee
  • Helping professionals protect their largest asset, the ability to turn their advanced educations into a high income for their families, should they become disabled
  • Helping parents plan for the care of a special needs child after they are gone

Estate Planning

  • Helping you identify estate planning goals
  • Taking inventory of existing estate planning documents – wills, trusts, durable powers of attorney and healthcare directives – and comparing those documents to the client’s stated wishes
  • Consultation with client’s current estate planning attorney or referral to a suitable attorney to make necessary changes
  • Review of all beneficiary designations – on retirement plans, insurance policies, annuities, etc. – to ensure that they are up to date and in harmony with the client’s current wishes and estate plan
  • Strategic use of beneficiary designations to achieve client’s charitable goals in a tax-efficient manner

Education Planning

  • Helping clients identify education funding goals for children or grandchildren
  • Selection of appropriate savings vehicles – 529 college savings plans, UTMA accounts, Coverdell education savings accounts and ABLE accounts, Roth IRA or permanent life insurance
  • Creation of flexible accounts that are earmarked for education but not limited to education

Lifetime Cash-Flow Analysis (Crystal Ball Experience)

 We actually do have a crystal ball in our conference room, but in reality we use powerful financial planning software to help clients model “What If” scenarios. As a part of financial planning, we prepare lifetime cashflow analyses that help clients answer questions like:

    • What if I retire at age 55? 62? 70?
    • What if I start Social Security at 62? 67? 70?
    • What if I get a divorce and lose half of my net worth?
    • What if I get an inheritance? Or don’t get an inheritance?
    • What if I retire from my career and get a part-time job on the side?
    • What if I sell my home and downsize? Or upsize?
    • What if I make a major charitable gift during my lifetime?
    • What if I help my kids purchase a home or business?
    • What if I sell my rental property?

Helping people manage their financial goals since 2001

Through recessions, wars, political turmoil and even a global pandemic, we’ve helped people address their financial goals with personalized, comprehensive wealth management plans. It’s rewarding and fun. Here are some of the folks we’ve helped over the years:


    • We’ve helped successful small business owners turn their current cash flow into long-term wealth that outlasts their business.
    • We’ve helped young doctors come up with a plan to pay off their student loans and turn their high incomes into long-term wealth.
    • We’ve helped middle-aged couples create retirement income plans, transition into retirement 10 years later.
    • We’ve helped an inventor use his royalties to send 10 grandchildren to college and make a foundational gift to the local university.
    • We helped a mom set up a college plan for her daughter and watched that daughter graduate from college, start her career, purchase her first home and start her first Roth IRA account.
We could go on and on, but you get the idea. With our process, we’ll put you on a path toward achieving all of your financial goals so you can spend more time focusing on what’s important – living your best life, enjoying your friends and family, and making a difference for the people and causes you care about.

Learn from our advisors.