Sidepocket

Sidepocket is a venture-backed deep-tech company and SEC-Registered Investment Advisor built to solve a structural flaw in America's retirement system: self-employed workers cannot know how much they're allowed to contribute to tax-advantaged accounts like SEP IRAs or Solo 401(k)s until their income is finalized. Self-employment is the fastest-growing segment of the American workforce—accelerated by AI, the creator economy, and the shift toward independent work. Yet these 36 million Americans remain trapped between two bad options: overcontribute and risk IRS penalties, or contribute nothing for nearly a full year. The result is predictable. More than $200 billion in deductions and contribution room goes unused annually, and 99% of eligible independents contribute only at tax time—forfeiting up to 11 months of compounding. The IRS technically permits year-round contributions. But without knowing net earnings in advance, compliant monthly funding has been effectively impossible. Until now. The Tactical IRA™ eliminates this constraint. Powered by our patented Contribution Intelligence Engine™, the platform continuously analyzes real income patterns, models earnings volatility, and calculates safe contribution thresholds across multiple plan types—enabling fully compliant monthly contributions before income is finalized. This allows investors to deduct earlier, invest earlier, and compound earlier, without overcontributing or triggering penalties. Beyond contribution timing, the Tactical IRA™ employs regime-aware asset allocation, adaptive rebalancing, and volatility-sensitive hedging to reduce drawdowns across market cycles. The combination—continuous funding paired with institutionally-informed portfolio management—addresses what many consider a "holy grail" problem in retirement planning: transforming unpredictable income and tax complexity into consistent, optimized, year-round compounding. By delivering the timing discipline that institutions have always