Side Pocket
Founded 2020 · 22 employees on LinkedIn · 1 known investors
Sidepocket is a registered investment advisor that provides automated retirement investing and contribution planning tools for self-employed Americans, freelancers, and business owners with variable income. The platform calculates safe retirement contributions and uses tactical automated investing to help gig workers and independent professionals save for retirement throughout the year.
Also known as Sidepocket · Sidepocket Tactical IRA
Founders & leadership
Side Pocket was founded in 2020 by Morgan McQuown.
Investors · 1
Company profile
researched Aug 2026Sidepocket operates a managed retirement product marketed as the Tactical IRA, aimed at self-employed professionals whose income varies through the year. The company builds a combination of account types for each user — SEP IRA (contributions of up to $72,000/year), Traditional IRA and Roth IRA (up to $7,500/year each) — selected according to the user's income, business structure and goals, and then determines how much to direct into each account. Additional account types, including a Solo 401(k) (up to $70,000/year), an HSA (up to $4,300/year) and tax-advantaged crypto custody for assets such as Bitcoin and Ethereum, are listed as coming soon, as are backdoor Roth conversions.
Onboarding is presented as a three-step process: account structure setup, calculation of a safe contribution amount, and automated contribution and investing. Users link bank accounts through Plaid on a read-only basis, covering a stated 8,000+ banks, and funds remain at the user's bank until contributed. A dashboard displays a current-year contribution limit, tracked year-to-date income, estimated tax savings, a monthly "safe to contribute" figure and an income-tracking confidence score. The company also publishes a public calculator that estimates contribution limits from annual self-employment income, business structure (sole proprietor/LLC, partnership/multi-member LLC, or S-corporation) and income stability (stable, seasonal or variable).
Sidepocket describes itself as an SEC-registered investment advisor and fiduciary with SIPC coverage of up to $500,000, and states that it is not a tax advisor, leaving final contribution eligibility to a user's tax professional. Marketing materials cite potential annual tax savings of up to roughly $26,200–$37,000 under stated assumptions of $79,500 in combined annual contributions at top federal (37%) and state (13.3%) tax brackets.
Business model
Sidepocket manages retirement accounts for individual self-employed clients as a registered investment advisor, handling account setup, contribution calculation, investing and rebalancing; the site references a pricing page for its plans.
Advisory service with pricing published on the company's site.
Traction
The site references a portfolio track record of more than three years and typical tax savings of about $15,000 for users earning $150,000 or more who contribute at least 15% of net income.
▸Full profile — market position, technology, go-to-market, risks & controversies
Market position
Positions the Tactical IRA against a standard IRA, contrasting the $7,500 annual regular IRA cap and roughly $2,475 of maximum tax savings with combined self-employed account limits of up to $79,500 or more per year.
Combines multi-account structuring for self-employed savers with a month-by-month safe contribution limit calculated from tracked income, rather than a single determination at tax time, plus automated contributions, tactical portfolios and rebalancing.
Technology
The core component is a "Contribution Intelligence Engine," described as patent pending, which analyzes a user's income patterns from linked bank data to estimate a safe monthly contribution amount that is updated as income changes. Bank connectivity is provided via Plaid with read-only access across 8,000+ institutions, and the site cites 256-bit encryption. Portfolios are managed with automatic contributions, tactical investing and auto-rebalancing.
Go-to-market
Direct-to-consumer acquisition through its website, including a free contribution-limit calculator and self-service account opening described as taking about five minutes.
Self-employed professionals with variable or seasonal income, including sole proprietors, single- and multi-member LLC owners, partners and S-corporation owners; marketing highlights users earning $150,000 or more contributing at least 15% of net income.
Risks & controversies
Site disclosures note that calculator outputs are estimates only, that actual contribution limits are determined by IRS rules, net self-employment income and entity type, that the company is not a tax advisor, and that past performance does not indicate future results.
Compiled by commissioned research from 8 cited public sources — announcements, filings, and press listed under research sources below.
Key figures
latest reportedCompany-reported or press-reported figures, each dated to when it was claimed — not independently audited.
▸Research sources · 8
primary sources listed
- Side Pocketsidepocket.com · web
8 public sources were cited for this profile; the first-party ones are listed here.
Frequently asked questions
- What does Side Pocket do?
- SEC-registered investment advisor offering a managed self-employed IRA that calculates safe monthly retirement contributions.
- Who founded Side Pocket?
- Side Pocket was founded by Morgan McQuown in 2020.
- Who are Side Pocket's investors?
- Side Pocket's investors include Miroma Ventures.