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Sherpa Wealth Strategies

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Bend, OR
Sherpa Wealth Strategies

Our customized programs are designed with the goal to grow your wealth by delivering an unprecedented level of personalized service. Member FINRA/SIPC.

Sherpa Wealth Strategies is a comprehensive financial advisory firm in Bend, Oregon, specializing in financial planning, retirement planning, asset management, sustainable investing, and insurance & annuities. Sherpa Wealth Strategies is a comprehensive financial planning & advising firm in Bend, Oregon committed to helping you improve your long-term financial success. Specializing in financial pl

anning, retirement planning, IRA planning, investment planning, asset management, sustainable investing, insurance & annuities, and social security planning. Our dedication to the financial success of our clients is unmatched. We combine our dedication and experience with something else that’s hard to find — a passion for making financial confidence accessible to everyone. Securities offered through LPL Financial. Financial Planning offered through Sherpa Wealth Strategies, LLC, a Registered Investment Adviser and a separate entity from LPL Financial. Third party posts found on this profile do not reflect the views of LPL Financial and have not been reviewed by LPL Financial as to accuracy or completeness. The financial professionals associated with LPL Financial may discuss and/or transact business only with residents of the states in which they are properly registered or licensed. No offers may be made or accepted from any resident of any other state.

12/25/2025

As the snow settles and the year winds down, we pause to reflect on what truly matters: meaningful connections, shared journeys, and the milestones we’ve reached together.

At Sherpa Wealth Strategies, we're honored to walk alongside you — not just through markets and milestones, but through life’s seasons.

From our team to you and your family:
Happy Holidays, and may the coming year bring peace, prosperity, and purpose.

12/16/2025

“What if you could step off the jetway at 60 and still grow your wealth by seven figures?”

That was the question when I met with a long-tenured pilot this week. Her plan: leave the cockpit at 60, delay her company pension to 65, and use those five low-income years—the “Goldilocks zone”—for systematic Roth IRA conversions. By filling the gap with cash reserves and a military pension, she keeps lifestyle intact while shifting pre-tax assets into tax-free territory. The forecast: roughly $1.8 million more in projected assets and significantly lower lifetime taxes, all without picking up an extra flight. The takeaway: retirement isn’t just about dates; it’s about sequencing income, taxes, and flexibility. Where’s your Goldilocks zone hiding?

If you're facing a similar situation, let's run the numbers together. Message us or call us at 541-633-7728.

12/10/2025

“How do I convert money into a Roth without sending a penny to the IRS?”

That was the puzzle in one review this week. My client was juggling everyday goals—booking a spring paint job and dreaming about an Egypt cruise — yet her projected taxable income for 2025 sat unusually low. By running the numbers together, we found room for a $23,000 in-plan Roth 401k conversion that added long-term flexibility while keeping her federal tax bill at precisely $0. A move that small can feel almost invisible today, but it can mean thousands more in after-tax spending power down the road—whether that’s for a new kitchen floor or a Scandinavian adventure. Year-end is the perfect moment to peek at your income and ask: “Am I leaving tax-free opportunities on the table?”

Let's run the numbers together. Message us or call us at 541-633-7728.

12/02/2025

“Once the car is paid off, can we really afford to crank up our Roth IRA?”

That was the big question from a newly married couple, so we crunched the numbers: redirecting the soon-to-disappear car payment into their Roth IRAs bumps monthly savings from $100 to $583. The math? Over 30 years, that single shift could add roughly three-quarters of a million dollars to their retirement nest egg — without touching the rest of their cash flow. Small, intentional moves made at life’s pivot points often carry the most weight. If a loan, subscription, or expense is about to disappear, pause and ask: “Where could this money build the most future value?”

If you're facing a similar situation, let's run the numbers together. Message us or call us at 541-633-7728.

11/25/2025

“Will my spouse be okay if my health takes a turn?”

That was the heartbeat of yesterday’s review. Across the table sat a couple fresh off the husband’s final chemo session—fatigued yet hopeful—wondering how a single-life pension, an expiring term life policy and a half-funded trust would stack up if the worst happened. We walked through every “what if,” from replacing lost income to funding college for a grandchild. We demonstrated that their financial plan holds, even after factoring long-term care and a more conservative portfolio mix. The relief in the room was palpable. Numbers can’t cure cancer, but they can calm the mind. When life throws uncertainty your way, ask yourself: have you modeled the tough scenarios? A few intentional moves today can turn anxiety into confidence.

If you're facing a similar situation, let's run the numbers together. Message us or call us at 541-633-7728.

11/19/2025

“Ever felt wealthy on paper yet stretched to make payroll?”

A client who has been unlocking her business at dawn every morning since June brought me that dilemma. On paper, her net worth tops seven figures, thanks to good savings habits and ownership of a business and a commercial building. In reality, the mortgage on that commercial building — and a creeping credit-card balance from medical expenses — were choking cash flow.

During our review we:
▪️Mapped assets vs. liabilities and income vs. expenses to reveal the gap between net worth and liquidity.
▪️Recommended a lower-cost HELOC to wipe out high-interest credit card debt.
▪️Explored renting the underused building to cover its own mortgage.
▪️Recommend increasing liability insurance coverage to protect what she’s already built.

Her takeaway: profit and peace of mind come from aligning cash flow, debt strategy, and risk protection—not just owning more stuff. If your balance sheet looks strong but your bank account feels weak, it may be time for a deeper look.

If you're facing a similar situation, let's run the numbers together. Message us or call us at 541-633-7728.

11/13/2025

“Will all this paper really protect our family?”

When a couple walked in carrying a three-inch estate-planning binder packed with colored tabs, that was their question.

We spread the documents out, traced each account on a whiteboard, and quickly found three gaps—a life policy missing from the asset worksheet, a taxable account with no beneficiary, and assets earmarked for a minor but not tied to the descendant’s trust. Ten minutes of retitling and a simple beneficiary form fixed what could have been months of probate headaches.

The lesson? Drafting a trust is step one; aligning every account and insurance policy to it is where the real peace of mind happens. When was your last beneficiary audit?

If you're facing a similar situation, let's run the numbers together. Message us or call us at 541-633-7728.

11/11/2025

“Why do we have EIGHT different IRAs… and do we really need them?”

That was the moment of truth in a recent meeting. Each year this couple had opened a fresh IRA without realizing the cost of fragmentation. The kicker: their current custodian charges $100 per account to transfer out. By consolidating those IRAs into a single account for each spouse we avoided $600 in transfer fees. We also decluttered statements and set the stage for real planning: risk-aligned portfolios, tax-smart Roth conversions, and a simpler path to future withdrawals. Before you chase performance or the latest market theme, ask yourself: could a little housekeeping create instant value and a cleaner financial life?

If you're facing a similar situation, let's run the numbers together. Message us or call us at 541-633-7728.

11/04/2025

“Building a multimillion-dollar app is exhilarating—realizing almost all your wealth is tied up in that one business is another story.”

In a recent review, a business founder admitted he had about $500k idling in a checking account, a condo loan at 6%+, yet only a modest investment portfolio outside the company. The business is growing at 30% per year and generating amazing cash flow. We discussed a business valuation and exit strategy, then mapped a three-year plan to move excess cash into a diversified investment account while still attacking the high-rate mortgage. One twist they loved: seeding a donor-advised fund so their charitable dollars earn an immediate tax break and can provide a lasting legacy.

The takeaway? When your company is soaring, remember to land some profits safely elsewhere—and let your generosity work just as hard as you do.

If you're facing a similar situation, let's run the numbers together. Message us or call us at 541-633-7728.

10/30/2025

“We’re ready to retire—but with two different advisors are we really coordinated?”

That was the question over homemade lemon-zest cookies at a recent kitchen-table review. My clients had healthy balances, a beach house they love, and big travel plans—yet two different advisors were making moves independent of each other. The result: surprise tax bills and an investment mix that no longer matched their comfort level.
In one conversation we mapped every IRA, brokerage, and inherited IRA account, then designed a single timeline: Roth conversions during their low-income window, a glide path to reduce equity exposure, and an umbrella liability policy to shield their growing net worth. The numbers didn’t just look good, they finally felt good.

Coordinating the moving parts is what turns “we think we’re fine” into confident, first-class retirement living. How seamless is your plan?

If you're facing a similar situation, let's run the numbers together. Message us or call us at 541-633-7728.

10/02/2025

“How much should we keep in the bank—and is it working hard enough?”

That question came up in a recent review when a couple realized their comfort-zone cash was sitting in a traditional savings account earning 0.04%. We did the quick math: moving the excess to a money-market fund at roughly 4% could add more than $1,500 a year—enough for two round-trip tickets to visit family overseas—without locking the money away. The insight wasn’t about chasing yield; it was about aligning the emergency fund with their goals: liquidity, safety and a fair return. Take five minutes this week to ask yourself: Is my “rainy-day” money still parked in 2020’s interest rate landscape, or have I let it catch up to 2025? Small moves can make a real difference.

If you're facing a similar situation, let's run the numbers together. Message us or call us at 541-633-7728.

09/05/2025

“What happens to my future if I can’t go back to work?”

That was the question on a client’s mind after a sudden health setback. Together we laid everything on the table—COBRA health insurance premiums of nearly $900, a car lease, groceries and other expenses trimmed to $1,000, even the possibility of selling her home after fresh paint and new carpet. By mapping cash flow line-by-line, we found two high-impact moves: reallocating her overly conservative portfolio and delaying Social Security to age 70. The result? Her retirement confidence increased, all while keeping medical coverage intact during the transition.

Sometimes stability isn’t about earning more—it’s about re-ordering the pieces you already have. When life throws a curveball, a clear plan can turn anxiety into actionable steps.

If you're facing a similar situation, let's run the numbers together. Message us or call us at 541-633-7728.

Address

444 NE Norton Avenue, #101
Bend, OR
97701

Opening Hours

Monday	8:30am - 5pm
Tuesday	8:30am - 5pm
Wednesday	8:30am - 5pm
Thursday	8:30am - 5pm
Friday	8:30am - 5pm

Telephone

+15416337728

Website

http://www.sherpawealthstrategies.com/

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