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Robert Joseph Caldwell

Advisor at Mass Mutual Investors Services — Lake Oswego, OR

Updated today

Credentials

CFP®, ChFC®, Series 66

Experience

13 years

Location

Lake Oswego, OR

Mass Mutual Investors Services logo

Mass Mutual Investors Services

Institution

Total advisors

5,064

Across 1,219 offices

Clients per advisor

89 Typical

Avg AUM per client

$249,379 Low

HNW client ratio

0% Very Low

About

Robert Caldwell is a financial advisor at Mass Mutual Investors Services with 13 years of industry experience. He holds the CFP® and ChFC® designations and has worked with several firms including Price Financial Group and Wealth Management, Inc. Caldwell also engages in insurance and annuity sales through Asset Preservation Wealth and Tax in Lake Oswego, Oregon. Mass Mutual Investors Services operates as a broker-dealer and SEC-registered investment adviser serving individuals, high-net-worth clients, business owners, trusts, estates, charitable organizations, and employers. The firm offers financial planning, asset management, and educational seminars, using firm-approved tools and a collaborative approach to deliver written recommendations tailored to client goals.

Client services

Based on Mass Mutual Investors Services

Financial planning Portfolio management Pension consulting Selection of other advisers Educational seminars or workshops Asset allocation programs

Expertise

Based on Mass Mutual Investors Services

Divorce financial planning General estate planning guidance Multi-generational wealth transfer Cash flow / budgeting

Occupation focus

Based on Mass Mutual Investors Services

Founder/Business Owner Attorney Executive

Demographic focus

Based on Mass Mutual Investors Services

Married/Couples/Partners Divorced

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Fee options

Commissions

Commissions on securities and insurance products sold; commissions vary by product

Other

Minimum fee: Minimum annual fee of $500 for Financial Planning Services Fee-only: Annual financial planning fees range from $500 up to over $35,000, negotiable and possibly waived

Location

See office

Lake Oswego, OR

Lake Oswego OR

Advisors at this office

1

Most active in

Washington

Work history

13 years of industry experience

Mass Mutual Investors Services

2026 - Present • 1 year

Lake Oswego, OR

MassMutual

2026 - Present • 1 year

Springfield, MA

Foundations Investment Advisors, LLC

2025 - 2026 • 1 year

Lake Oswego, OR

Wealth Management, Inc.

2022 - 2025 • 3 years

Portland, OR

CWM, LLC

2021 - 2022 • 1 year

Omaha, NE

Price Financial Group

2018 - 2025 • 7 years

Portland, OR

Fsc Securities Corp

2018 - 2018 • 1 year

Atlanta, GA

LPL Financial, LLC

2016 - 2018 • 2 years

Portland, OR

Mass Mutual Investors Services

2016 - 2016 • 1 year

Lake Oswego, OR

MASSMUTUAL Life Insurance Company

2016 - 2016 • 1 year

Lake Oswego, OR

Disclosures

Exclamation point means they have disclosures of this type. Check mark means no disclosures of this type were found.

Business activities & affiliations

Will S

Series 65

Lake Oswego, OR

Stoneholt Wealth

After seven years of in and around this industry (as a marketer, consultant, and content creator... but never an advisor) I decided to hang my shingle and start Stoneholt Wealth. We're a fee-only financial planning firm that's built exclusively for high-income millennial couples with kids (I have three kids under 5... it's a crazy time). We help our clients with career transitions, concentrated wealth, variable sales income, liquidity events, and all the little stuff in between--if you can call buying a home "little". We cover everything from income strategy to investments to tax planning to insurance review, all in the name of taking this very important responsibility off your plate, so you can focus on the stuff that makes life better.

Wealth management RSUs / ISOs / NSOs Equity compensation tax strategy Early retirement planning Life insurance needs analysis Technology Professional Sales Professional HENRY (High Earners, Not Rich Yet) Mid-Career Professionals Career Changers

Chris R

Series 65

Lake Oswego, OR

Cascara Financial Planning LLC

Chris Ramsby is the principal of Cascara Financial Planning LLC in Lake Oswego, OR. He holds a Series 65 designation and has experience working at Para Wealth Advisors and Elite Sales & Marketing prior to founding Cascara Financial Planning in 2025. Cascara Financial Planning advises individuals and high-net-worth clients with wealth management and financial planning services that include retirement, tax, estate, business, cash-flow, and college savings planning. The firm’s investment approach is based on modern portfolio theory, combining passive and active strategies with options for socially conscious investing.

College savings (529s, UTMA, etc.) Business ownership considerations General estate planning guidance Wealth management Retirement income strategy Self-Employed Educators, Teachers, and Academics Pharmacist Sales Professional Executive HENRY (High Earners, Not Rich Yet) Young Professionals Young Families Mid-Career Professionals Gen Y/Millennials (Born 1980-1995)
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Suzanne H

CFP®, CFA®, Series 65

Portland, OR

Core Planning

Suzanne Highet is a financial advisor at Core Planning in Portland, OR, holding the CFP®, CFA®, and Series 65 credentials with 21 years of industry experience. Her prior roles include positions at The Stanich Group LLC, Highet Advisory LLC, and CTC Consulting, LLC. Outside of her advisory work, she operates Highet Advisory LLC, a business consulting service focused on supporting registered investment advisors with investment programs and portfolio management. Core Planning provides fee-based financial planning and wealth management services to individuals, retirement plans, trusts, estates, charitable organizations, and business entities. The firm customizes investment strategies based on client goals and risk tolerances, using a combination of in-house advice, third-party money managers, and model portfolios.

Early retirement planning RSUs / ISOs / NSOs Wealth management ESG / Sustainable investing Passive / index investing HENRY (High Earners, Not Rich Yet) Mid-Career Professionals Women's Finance Approaching retirement LGBTQIA
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Joshua T

CFP®, Series 66

West Linn, OR

Independent Financial Group, LLC

Joshua Tschirgi is a CFP® professional with 14 years of industry experience, currently serving at Independent Financial Group, LLC since 2019. He previously worked at Somerset Securities, Inc. from 2015 to 2018. Outside of his advisory role, he is a licensed insurance agent and manages True Path Capital Strategies, a marketing DBA. Independent Financial Group, LLC is a dual-registered broker-dealer and SEC-registered investment adviser that provides brokerage, portfolio management, financial planning, and retirement plan services to individuals, charities, corporations, and plan sponsors. The firm offers advisory programs through its AccessPoint platform and third-party asset managers, serving a diverse client base including high-net-worth individuals and institutional clients.

Wealth management Passive / index investing Active portfolio management Private / alternative investments Retirement plans for business owners (SEP, solo 401k) Founder/Business Owner Executive
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Todd C

Series 63, Series 65

Lake Oswego, OR

Executive Investment Services, LLC

Todd Caudle is a financial advisor at Executive Investment Services, LLC with 36 years of industry experience. He holds Series 63 and Series 65 licenses and has worked at Executive Investment Services since 2009, as well as at Independent Financial Group during overlapping periods. Caudle is an officer and principal of Medical Professionals Financial Group, a marketing entity within the investment channel. Executive Investment Services provides asset management and financial planning to individual clients, including high-net-worth households, and consulting for small- and medium-sized businesses. The firm offers discretionary portfolio management with strategic and tactical asset allocation, and integrates investment management with insurance and executive-benefit services.

Private / alternative investments Business exit / sale strategy Founder/Business Owner Executive
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Jeremy W

CFP®, Series 65

Lake Oswego, OR

Davidson & Watson Financial

Jeremy Watson is a CFP® and holds a Series 65 license with seven years of industry experience. He has worked at Watson Financial, LLC since 2020 and previously at Tony H. Davidson Comprehensive Financial Management, LLC from 2017 to 2020. Prior to his financial career, he was affiliated with St. Andrew's Presbyterian Church for seven years. Davidson & Watson Financial provides portfolio management and financial planning services to individuals, high-net-worth clients, and small businesses. The firm employs both fundamental and technical analysis, managing portfolios with a variety of securities and reviewing accounts at least quarterly.

General retirement planning Income planning Wealth management Founder/Business Owner
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