Derek Cheshire
Advisor at Scholar Financial Advising, LLC
Data sourced from SEC public records (and other sources when available). Some details may be added by the advisor after claiming their profile. Refreshed daily • Updated today.
Advisor at Scholar Financial Advising, LLC
Data sourced from SEC public records (and other sources when available). Some details may be added by the advisor after claiming their profile. Refreshed daily • Updated today.
Location
Westminster, CO
Credentials
CFP®, Series 66
Industry experience
12 years
Derek Cheshire is a CFP® with 12 years of industry experience, currently serving at Scholar Financial Advising, LLC. His prior experience includes roles at Origin Financial, Securities America, Inc., and Ameriprise Financial Services, Inc. Outside of advisory work, he provides tax preparation and bookkeeping services through Cheshire Financial Services and offers outsourced CFO services via Level 10 CFO. Scholar Financial Advising serves high-income and ultra high-net-worth individuals, delivering comprehensive financial planning and a Signature Coaching Program primarily through online platforms. The firm emphasizes a long-term, allocation-driven investment approach focused on passive market exposures and tax-aware asset location, operating on a flat-fee and hourly project basis rather than traditional asset-based fees.
Based on Scholar Financial Advising, LLC
Based on Scholar Financial Advising, LLC
Initial comprehensive financial plan flat fee starting at $7,000; Signature Coaching Program initial fee typically $15,000 to $30,000
$385 per hour (hourly financial planning after initial plan)
Signature Coaching Program recurring monthly flat fee starting at $4,000/month
Account minimum: $1,000,000 income or $10,000,000 assets (recommended for Signature Coaching Program, waivable) Fee-only: Flat fee comprehensive initial plan starting at $7,000; typically $10,000 to $15,000; hourly advice at $385/hour; Signature Coaching Program monthly fees start at $4,000/month
Westminster, CO
Colorado · Texas
Scholar Financial Advising
2023 - Present (3 years)
Cheshire Financial Services
2022 - Present (4 years)
Origin Financial
2022 - 2023 (1 year)
Level 10 CFO
2020 - Present (6 years)
Securities America, Inc.
2019 - 2022 (3 years)
Townsend Retirement
2019 - 2022 (3 years)
U.S. Bancorp Investments, Inc.
2017 - 2019 (2 years)
Ameriprise Financial Services, Inc.
2013 - 2017 (4 years)
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Insurance agent
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Accountant / CPA / tax prep
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Lawyer
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Real estate agent
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