Unconventional Investor, LLC
Data sourced from SEC public records (and other sources when available). Refreshed weekly • Updated today.
About
Unconventional Investor serves individual clients, including high-net-worth individuals, managing roughly $302.5 million across 88 accounts through a two-advisor team. The firm provides portfolio evaluation, ongoing discretionary portfolio management, and integrated financial planning as part of its management services.
The firm follows a Swensen-style asset allocation philosophy that emphasizes simple, low-cost index funds for equities and U.S. Treasury securities/TIPS for fixed income, favoring long-term buy-and-hold positions and infrequent trading. Portfolios are mass-customized to client risk profiles and goals, with ongoing monitoring, periodic rebalancing, and scheduled outreach to review plans as circumstances change.
What stands out for this firm is the concentration of assets relative to its small advisory team, producing a high assets-per-advisor and assets-per-client profile compared with peers. Operationally it requires custody with its chosen custodian and handles trading under limited powers of attorney—executing trades for individual accounts rather than aggregating orders—and it does not accept proxy-voting authority on client securities.
Client services
Expertise
Fee options
$0 - $500,000: 0.40% annually $500,001+: 0.20% annually
Account minimum: $250,000
Main office
See officePortsmouth NH
Advisors at this office
1
Most active in
California · New Hampshire · North Carolina · Texas
Disclosures
Exclamation point means they have disclosures of this type. Check mark means no disclosures of this type were found.
Business activities & affiliations
Is not active or affiliated with:
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Insurance agent
They sell insurance products and may earn commissions on those sales.
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Broker-dealer / trader
They provide brokerage services and may earn transaction-based compensation in addition to advisory fees.
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Bank
They're affiliated with a bank that may offer its own financial products and services.
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Trust company
They provide trust and estate administration services, typically for separate fees.
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Fund sponsor
They manage or sponsor investment funds and may earn management or performance-based fees if clients invest in them.
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Accountant / CPA / tax prep
They offer tax and accounting services, typically for separate fees.
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Lawyer
They provide legal services, typically billed separately.
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Real estate agent
They facilitate real estate transactions and may earn commissions.
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Other specialized services
They may provide services such as pension consulting or municipal advisory work, typically for separate fees.
Advisors at this firm
Christopher O
Series 65
Charlotte, NC
Unconventional Investor, LLC
Christopher O'Leary is a financial advisor with Unconventional Investor, LLC in Charlotte, NC, holding a Series 65 designation and six years of industry experience. Prior to joining Unconventional Investor in 2019, he worked at Keyence Corporation from 2014 to 2018. Unconventional Investor primarily serves individual clients, including both high-net-worth and non-HNW individuals, offering discretionary portfolio management, initial portfolio evaluations, and periodic financial planning. The firm’s investment approach emphasizes asset allocation using low-cost equity index funds and U.S. Treasury bonds, with portfolios customized to each client’s risk profile and managed with a buy-and-hold, low-turnover strategy.
Paul O
Series 65
Portsmouth, NH
Unconventional Investor, LLC
Paul O'Leary is a financial advisor at Unconventional Investor, LLC with 18 years of industry experience. He holds a Series 65 credential and has been with Unconventional Investor since 2007. Unconventional Investor primarily serves individual clients, including both high-net-worth and non-HNW individuals, offering discretionary portfolio management, initial portfolio evaluations, and periodic financial planning. The firm’s investment approach emphasizes asset allocation based on a framework influenced by David Swensen, utilizing low-cost equity index funds and U.S. Treasury bonds and TIPS, with portfolios customized to client risk profiles and managed with a buy-and-hold, low-turnover discipline.
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