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John David Chesbrough

John David Chesbrough

CFP®
TRAIL FINANCIAL PLANNING
BELLINGHAM, WA
·CRD# 6104183·14 years experience

Professional Summary

John David Chesbrough, CFP® is a registered financial advisor currently at TRAIL FINANCIAL PLANNING LLC located in Bellingham, Washington. John is registered as an IAR (Investment Advisor Representative) and started their career in finance in 2012. John has worked at 1 firm and has passed the Series 65 exam.

At a Glance

Always Fiduciary

Fiduciary Standard

Fee Structure

$100K–$250K

Account Minimum

Active Clients

Fiduciary Standard

Fee Structure

Account Minimum

Active Clients

Services Offered

  • Education Funding
  • Retirement Planning
  • Financial Planning
  • Tax Planning
  • Investment Management
  • Cashflow & Budgeting

Specializations

Financial Therapy
ESG & Impact Investing

Biography

John Chesbrough, CFP(R), is a Bellingham, WA fee-only financial planner. John founded and co-owns Trail Financial Planning LLC in order to provide comprehensive and objective financial planning and investment management to help clients organize, grow and protect their assets through life’s transitions. As a fee-only financial advisor, John is never paid a commission of any kind.  As the owner of an independent business, John can advocate for his clients without the pressures from an umbrella...

Other Aliases

There are no additional aliases reported.

Blog Corner

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Videos & Posts

This advisor has not added any videos or posts yet.

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Contact Information

Direct

(xxx) xxx-xxxx

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Disclosures are events reported to regulators, such as customer disputes, regulatory actions, employment separations, or financial events. Some are resolved, denied, or contested — a disclosure is not a verdict. We recommend asking an advisor directly about any disclosure on their record.

Disclosures on record.

Disclosures can be potential red flags, including customer disputes, regulatory fines, employer terminations, bankruptcies, judgments, liens, or certain criminal activities. Check for any disclosures as part of your thorough research when choosing an advisor.

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Credentials

CFP®
Certified Financial PlannerSince 2019

Years of Experience

14 years in the financial services industry

Current & Past Employments

TRAIL FINANCIAL PLANNING LLC·CRD# 165063
RIA
214 N Commercial St., Bellingham, WA 98225
November 20, 2015 - Present
TRAIL FINANCIAL PLANNING LLC·CRD# 165063
RIA
Bellingham, WA
November 19, 2012 - December 6, 2013

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Current Firm

TRAIL FINANCIAL PLANNING LLC
TRAIL FINANCIAL PLANNING LLC

CHESBROUGH, JOHN | TRAIL FINANCIAL PLANNING, LLC | TRAIL FINANCIAL PLANNING LLC | TRAIL FINANCIAL LLC | TRAIL FINANCIAL ADVISING LLC | JOHN D CHESBROUGH | JOHN CHESBROUGH | CHESBROUGH, JOHN DAVID

CRD#: 165063 / SEC#: 801-135022
RIA
Registered Investment Advisory firm - SEC (1/5/2026 Approved)
Washington
Registered Investment Advisory firm - Washington (2/12/2026 Terminated)
Why is a state registration marked "Terminated"? When a firm registers with the SEC (usually after managing $100M+ AUM), it often withdraws separate state firm registrations unless required by that state. The firm can still serve clients there through its individually registered Investment Advisor Representatives (IARs).

Contact Information

Main Address

214 N Commercial St., Bellingham, WA 98225

Phone Number

(360) 399-6486

# of Employees

4

SEC notice filing (1 States and Territories)

Registered to provide investment advisory services in 1 US states and territories.

Documents

Customer Relationship Summary (CRS / SEC)Latest Form ADV

Part 2 Brochures

TRAIL FINANCIAL PLANNING LLC - FORM ADV PART 2A (3/10/2026)

Regulatory Assets Under Management

Total Number of Accounts

606

AUM (Assets Under Management)

$117,334,223

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Other business activities

Information obtained from regulatory filings. Advisors can request corrections through their firm or regulator.

Outside business activity is any business or activity undertaken by an advisor that is outside the scope of their relationship with their firm (e.g., consulting services, real estate, freelance work, teaching, etc.). Investors should stay informed about these activities to ensure no conflicts of interest.

the name of the other business: 214 Commercial, LLC whether the business is investment-related: NO the address of the other business: 214 N Commercial St, Bellingham, WA the nature of the other business: RENTAL PROPERTY MANAGEMENT your position, title, or relationship with the other business: PARTNER the start date of your relationship: JUNE 2014 the approximate number of hours/month you devote to the other business: 2 the number of hours you devote to the other business during securities trading hours: 0 briefly describe your duties relating to the other business: LANDLORD DUTIES (MAINTENANCE, PROPERTY UPKEEP, ETC.)

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Primary Firm SEC Registration

This SEC-registered firm can serve clients nationwide. Some states may require the firm to submit a notice filing if the firm has more than 5 clients or a physical office there. You can view these state-level filings under the section titled "State Registrations and Notice Filings".
TRAIL FINANCIAL PLANNING LLC
TRAIL FINANCIAL PLANNING LLC

CHESBROUGH, JOHN | TRAIL FINANCIAL PLANNING, LLC | TRAIL FINANCIAL PLANNING LLC | TRAIL FINANCIAL LLC | TRAIL FINANCIAL ADVISING LLC | JOHN D CHESBROUGH | JOHN CHESBROUGH | CHESBROUGH, JOHN DAVID

CRD#: 165063 / SEC#: 801-135022
RIA
Registered Investment Advisory firm - SEC (1/5/2026 Approved)
Washington
Registered Investment Advisory firm - Washington (2/12/2026 Terminated)
Why is a state registration marked "Terminated"? When a firm registers with the SEC (usually after managing $100M+ AUM), it often withdraws separate state firm registrations unless required by that state. The firm can still serve clients there through its individually registered Investment Advisor Representatives (IARs).

State Registrations and Notice Filings

Listed states reflect where the advisor is authorized to serve clients under state regulations.
IAR
means the advisor is registered as an Investment Advisor Representative in this state and is authorized to provide investment advice to clients there.
IAR
Washington
(11/20/2015)

Don't see your state listed? The advisor may still be able to work with you under the federal De Minimis Rule, which allows up to five investment advisory clients in a state without registration. Some states, like TX, LA, NE, and NH, may still require registration or notice filing. Contact the advisor or their firm to confirm their investment advisory availability in your state.

Exams

Financial professionals may take different exams throughout their careers based on the types of services they provide and roles they perform.

Series 65 — Uniform Investment Adviser Law Examination

Passed Jun 2012About the Series 65 exam

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CRS (Client Relationship Summary) - RIA

Click below to view John David Chesbrough's CRS (Customer Relationship Summary).

CRS (Customer Relationship Summary)

Services Offered by John

  • Education Funding
  • Retirement Planning
  • Financial Planning
  • Tax Planning
  • Investment Management
  • Cashflow & Budgeting

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