Appleseed Planner

What Appleseed Planner does

Appleseed Planner operates a free, direct-to-consumer retirement planning web platform that runs Monte Carlo simulations to model financial outcomes for tech professionals holding concentrated equity compensation. Founded in 2024 by Adam Waaramaa — a former Boston Consulting Group consultant and tech corporate strategy executive with a Wharton MBA and a Group PM background in AI/ML Research — the company is headquartered in San Francisco and targets senior technology employees (including those at Google, Meta, Nvidia, and Amazon) who face planning complexities around RSU vesting, pre-IPO lockups, and concentrated stock positions.

The core product is a proprietary simulation engine that evaluates each user plan across 500 independent Monte Carlo paths, with year-by-year computation of federal and state taxes across all 50 states (including California's full marginal structure), long-term capital gains, the 3.8% NIIT surtax, FICA/payroll, and Medicare IRMAA surcharges, alongside a tax-aware withdrawal waterfall. The engine models overlapping RSU vesting waterfalls, refresh grants, pre-IPO lockup buckets, and sell-to-cover mechanics; treats housing as a full system with amortization, appreciation, maintenance, property tax, and adaptive downsizing; and offers a dedicated Dot-Com stress test that simulates employer equity against historical top-20 dot-com stock returns. An AI assistant (the Appleseed Assistant), built on Google's Gemini, reads each plan model and generates plain-English explanations of success probability, swing factors, and what-if comparisons.

The business model is freemium on the consumer side — the planning tool is 100% free with no account required — while revenue is generated through an Investment Adviser Referral Service that matches users with unaffiliated third-party Registered Investment Advisers via proprietary algorithms, for which Appleseed receives referral compensation. Investment advisory services are offered through Appleseed Advisory, LLC, an SEC-registered investment adviser; the planning tool and educational content are delivered by a separate affiliated entity, Appleseed Technologies, LLC. The company is founder-owned with no disclosed institutional funding and operates with a 1–10 person headcount.

Name

Appleseed Planner

Legal name

Appleseed Advisory, LLC

Website

https://appleseedplanner.com

Company type

Private

Founded year

2024

Operating status

Operating

Headcount range

1–10 employees

Short description

Appleseed Planner operates a free, self-serve Monte Carlo retirement planning platform built for tech professionals with concentrated equity compensation. It runs 500-path simulations covering RSU vesting, pre-IPO lockups, and tax-aware withdrawals, monetizing via referrals to third-party RIAs.

Ownership category

akta.pro rank

Product category

Retirement Planning Software

SIC

Investment Advice (6282)

akta.pro primary industry

Retirement Income Planning & Decumulation Advisory (FSAEABAD)

akta.pro secondary industry

Comprehensive Financial Planning (FSAEAAAA)

Keywords

• Retirement planning software
• Monte Carlo simulation
• RSU equity planning
• Financial planning tools
• Tax-aware modeling

Headquarters

HQ city

San Francisco

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Software

Cost components

Technology or R&D, Operations, Personnel, Marketing or Sales, Infrastructure

Revenue model

1. Investment Adviser Referral Service: The platform refers users to unaffiliated third-party Registered Investment Advisers (Third-Party RIAs). Appleseed receives compensation from these Third-Party RIAs for each referral. The selection of RIAs is based on proprietary algorithms matching user criteria. This creates a conflict of interest which is disclosed in Form ADV.

Pricing tiers

Go-to-market motion2 records

Distribution channels2 records

Marketing channels5 records

Core offering

Appleseed Planner is a free, web-based Monte Carlo simulation retirement planning platform that models income, vesting, spending, full tax computations, and tax-aware withdrawal waterfalls across 500 independent paths. It is purpose-built for senior technology employees and professionals with concentrated equity compensation, supporting RSUs, refresh grants, pre-IPO lockups, sell-to-cover mechanics, housing transitions with adaptive downsizing, and concentrated stock stress testing against a historical Dot-Com scenario.

Product overview

Appleseed Planner is a single, unified retirement planning platform that combines Monte Carlo simulation with AI-powered insights to help tech workers and professionals plan for retirement. The core product is the Appleseed Planner, which is enhanced by two specialized sub-products: the Dot-Com Stress Test for RSU risk analysis, and the Appleseed Assistant for AI-generated plan explanations. The platform integrates tax-aware simulation across all 50 states, models tech equity including RSU vesting waterfalls and pre-IPO lockups, and supports housing transition planning with adaptive downsizing. Users can access the tool via Google Authentication or magic link email, with all financial data encrypted using AES-256 at rest and HTTPS in transit.

Differentiator

Problem solved

Functional benefit

Products and services

• Appleseed Planner A free, web-based Monte Carlo simulation retirement planning tool that evaluates each user's plan across 500 independent paths, modeling income, RSU vesting, spending, full federal and state tax computations (all 50 states), tax-aware withdrawal waterfalls, housing transitions, and adaptive downsizing. Targeted at tech workers and professionals with concentrated equity compensation who want advisor-grade probabilistic retirement planning without paying traditional advisor fees.
• Dot-Com Stress Test A standalone concentrated-stock stress testing tool that separates employer equity from broad market risk and simulates a concentrated position using historical returns and volatility of the top 20 dot-com stocks since the 2000 bust, allowing tech employees to test whether their financial plan survives a repeat of the Nasdaq's 77% fall. Free to use.

Quantifiable outcome

• 500 independent Monte Carlo paths per plan
• +2 more outcomes

Named customers2 records

Segments3 records

Ideal customer profiles2 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration2 records

AI capability3 records

Feature6 records

Partnerships

One partnership is on record.

• Third-Party Registered Investment AdviserscoreChannel Partner/ Reseller/ DistributorAppleseed operates an Investment Adviser Referral Service that uses proprietary algorithms to match platform users with unaffiliated Third-Party RIAs. Based on user questionnaire responses and RIA profiles, the platform selects RIAs that appear to best match user needs. Appleseed receives compensation from these Third-Party RIAs for referrals, creating a revenue stream. This is disclosed as a conflict of interest in Form ADV and CRS filings.

Scale indicators4 records

Recent moves5 records

Expansion highlights5 records

Broad incumbents

• eMoney Advisor: eMoney Advisor is a comprehensive financial planning platform used by advisors and their clients for retirement, tax, estate and Monte Carlo-based planning. It addresses the same planning workflow as Appleseed, but is positioned as a professional-grade incumbent serving advisor firms.
• Empower (Personal Capital): Empower is a large retail wealth platform — combining the legacy Personal Capital dashboard with retirement accounts and advisory services — and serves millions of consumers with planning, account aggregation and advisory tools. It overlaps with Appleseed on retirement planning and investment advisory, but at vastly larger scale across a broader user base.

Others

• Pontera: Pontera is a platform that enables advisors to manage clients' retirement accounts (401(k), 403(b), etc.) held at other institutions. It is adjacent to Appleseed's retirement planning theme — sitting in the same tech-savvy retirement ecosystem — but facilitates ongoing account management rather than direct Monte Carlo planning.

Emerging players

• Wealth.com: Wealth.com is an estate and financial planning platform for advisors that incorporates tax-aware, Monte Carlo-based projections. It addresses a similar Monte Carlo planning workflow to Appleseed, but is positioned for advisor distribution and includes a heavy estate-planning emphasis.
• Origin: Origin is a financial planning platform focused on tech employees and their equity compensation, offering RSU modeling and integrated advisory services. It targets the same senior-tech-worker persona as Appleseed and overlaps strongly on RSU-centric retirement planning.
• Monarch Money: Monarch Money is a consumer personal finance and wealth planning platform with budgeting, goal tracking, and now planning and advisory layers. It overlaps with Appleseed on the consumer financial planning front and on serving tech-savvy DIY users with retirement and goal planning.
• Holistiplan: Holistiplan is a tax planning tool for advisors and consumers that automates year-round tax projections and integrates with retirement planning workflows. It is adjacent to Appleseed's tax-aware simulation capability, intersecting on the consumer/tech-tax-planning workflow but focused on tax rather than full retirement projection.

Direct peers

• RightCapital: RightCapital is a financial planning software for advisors that offers goal-based, Monte Carlo-driven retirement projections, tax planning and household aggregation. It is a close comparable to Appleseed on the Monte Carlo planning core, though primarily advisor-distributed rather than direct-to-consumer.
• Boldin (formerly NewRetirement): Boldin is a consumer-facing retirement planning platform that runs Monte Carlo simulations and financial planning scenarios for individuals. It overlaps directly with Appleseed's core self-serve retirement modeling offering and targets similar DIY retirement planners.
• MoneyGuidePro: MoneyGuidePro is an established Monte Carlo-based financial planning application widely used by financial advisors to produce goal-based, Monte Carlo-driven retirement projections for clients. It competes in the same Monte Carlo retirement-planning category that Appleseed has differentiated with tech-equity specialization.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

• LinkedInlinkedin.com/company/appleseed-planner

Compliance2 records

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Appleseed Planner