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John Cunningham

Principal/Chief Compliance Officer/Managing Member at Reality Financial Planning Services in Sarasota, FL

Investment adviser registrationUpdated

John Cunningham is Principal/Chief Compliance Officer/Managing Member of Reality Financial Planning Services, LLC, an investment adviser managing $126M, and works from its Sarasota, FL office. John Cunningham has been registered as an investment adviser representative through Reality Financial Planning Services since 16 November 2020, has 11 years in the industry across 3 firms and has passed the Series 65, Series 7 and Series 63.

11
Years in industry
5
Years at firm
3
Adviser firms
1
States registered

From the IAPD record, checked 22 October 2026SEC record

Career

John Cunningham has been Principal/Chief Compliance Officer/Managing Member of Reality Financial Planning Services since January 2023, is a control person of the firm and directly owns 75% or more of it. John Cunningham studied at the University of Florida.

Reality Financial Planning Services, LLC is a Sarasota, FL firm with $126M under management, 214 clients and 2 advisers in one office, as of its March 2026 filing.

John Cunningham III is with Reality Financial Planning Services, LLC, based in Sarasota, Florida. He began his career in banking and later moved into financial planning. He focuses on income, risk management, incapacity and estate planning for education, medical and nonprofit professionals in Sarasota.

John Cunningham’s longest registration is the current one, 5 years at Reality Financial Planning Services since 2020. Before joining Reality Financial Planning Services in 2020, John Cunningham was registered through Advice and Planning Services and Global Financial Private Capital, LLC.

  1. – present · 5 years
    Sarasota, FL · Adviser representative · Firm CRD 143352
  2. Advice and Planning Services
    – · 2 years
    Sarasota, FL · Adviser representative · Firm CRD 20472
  3. Global Financial Private Capital, LLC
    – · 2 years
    Sarasota, FL · Adviser representative · Firm CRD 132070

Credentials and registrations

Professional designations

Listed by Reality Financial Planning Services

  • CERTIFIED FINANCIAL PLANNER™ (CFP®)

Investment adviser representative registrations

John Cunningham is registered as an investment adviser representative in Florida, since November 2020.

  • FloridaSince 16 November 2020

Examinations

SIECredited
Name
Securities Industry Essentials Examination
Series 6321 June 2018
Name
Uniform Securities Agent State Law Examination
Series 711 June 2018
Name
General Securities Representative Examination
Series 651 September 2015
Name
Uniform Investment Adviser Law Examination

Key facts

Full name
John Joseph Cunningham
CRD
6543551
Role
Principal/Chief Compliance Officer/Managing Member
Office
3947 CLARK ROAD, Sarasota, FL 34233
Registration
Investment adviser registration
In the industry since
October 2015
Disciplinary history
Not yet shown here · SEC record

Common questions

Where does John Cunningham work?

John Cunningham has been Principal/Chief Compliance Officer/Managing Member of Reality Financial Planning Services, LLC since January 2023, and is a control person of the firm.

Source: Form ADV, Schedule A, filed 20 March 2026

Is John Cunningham a financial advisor?

Yes. John Cunningham has a current investment-adviser registration in Florida, through Reality Financial Planning Services since November 2020.

Source: IAPD individual record, checked 22 October 2026

How many years of experience does John Cunningham have?

John Cunningham has 11 years in the financial industry, since October 2015, across 3 adviser firms.

Source: IAPD individual record, checked 22 October 2026

What exams has John Cunningham passed?

John Cunningham has passed 3 licensing exams: the Series 65, Series 7 and Series 63. The earliest, the Series 65, was passed in September 2015. FINRA credited John Cunningham with the SIE, which began in October 2018.

Source: IAPD individual record, checked 22 October 2026

Where did John Cunningham work before Reality Financial Planning Services?

Before Reality Financial Planning Services, John Cunningham was registered through Advice and Planning Services, June 2018 to November 2020; Global Financial Private Capital, LLC, September 2015 to May 2018.

Source: IAPD individual record, checked 22 October 2026

Where is John Cunningham based?

John Cunningham’s registered office is in Sarasota, FL.

Source: IAPD individual record, checked 22 October 2026

Is John Cunningham registered with FINRA?

No. John Cunningham has no current broker registration.

Source: IAPD individual record, checked 22 October 2026

Is John Cunningham a CFP?

Reality Financial Planning Services lists John Cunningham with the CFP credential (“CERTIFIED FINANCIAL PLANNER™ (CFP®)”) on its website. CFP Board confirms certification status.

Source: John Cunningham III biography, realityfinancialplanning.com

How can I verify John Cunningham’s record?

Search CRD 6543551 on the SEC’s adviser search (adviserinfo.sec.gov), which publishes John Cunningham’s full registration record.

Source: IAPD individual record, checked 22 October 2026

Sources

  1. IAPD individual record, CRD 6543551, checked 22 October 2026. Registration status, employment history and examinations.
  2. Form ADV Part 1A, Schedules A and B of Reality Financial Planning Services, LLC, filed 20 March 2026. Title, control and ownership bands.
  3. Reality Financial Planning Services team page. Biography, education, credentials, awards.