Master Your Taxes
Like a Pro
Expert tax planning for high-income professionals—beyond filing, designed to save you more.
Expert tax planning for high-income professionals—beyond filing, designed to save you more.
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Avoid quarterly underpayment fines
Strategic timing on RSUs, crypto, real estate
Alerts for changes in tax law, income, or life events
Write off the gains when you sell property so you can take on the next project or diversify.
It's the biggest win you're likely to see. Keep more of it and make your hard-earned gains work for you.
You made a smart bet, and it's paid off.
Diversify your portfolio and eliminate the tax bill.
You've decided to take some gains. Eliminate the taxes and redeploy 100% of your capital immediately.
Write down what matters most to you
Plan recurring and one-time purchases
Estimate taxes, itemized deductions, & tax rate
Reconcile Student loans, mortages, & credit cards
Lesser has been designed for high-income earners—executives, entrepreneurs, doctors, and tech professionals. If you make over $200k, join members who are making smarter, faster financial moves.
Book a callLesser helped me easily navigate ISO exercises by building a model to weigh the pros and cons.
They handle all my K-1s without any hassle, and I don’t have to worry about a thing.
Lesser helped me estimate my tax obligations and stay on top of quarterly payments.
The process is super smooth, and the team at Lesser really knows their stuff.
Lesser helped me sell the right RSU shares on the right dates to maximize tax write-offs.
Lesser took care of my stock options, investment income and salary—without missing a beat.
Starting with the human experience.
The journey begins with our team of expert advisors, who prioritize understanding the unique financial needs of each member. Our financial advisors, backed by cutting-edge tools, ensure that every recommendation is crafted with care and context.
Our advisors work hand-in-hand with cutting-edge AI tools to pioneer intelligent automation in finance. From cash flow projections to tax optimization, we're creating seamless, data-driven solutions that reduce complexity and improve outcomes.
Our vision is to create AI capable of providing expert-level financial advice autonomously. Today, our team of trusted advisors is at the core of delivering personalized guidance, but we are building a future where AI can offer this same level of tailored support seamlessly.
How are we not? At Lesser, you have access to multiple advisors who will advise on all aspects of your finances—not just investment or retirement planning. Lesser gives you more than just access to advisors, we deliver a tech platform armed with your aggregated, real time data, available for you to access 24/7.
Nope. One advisor is the old way of doing things. At Lesser, we want to give you the best advice based on your specific situation or question—which is why we arm you with a team of experts (and tools) to address whatever your need might be.
We have a team of highly qualified advisors and experts working with our members. Amongst our advisors, we have:
Certified Financial Planner (CFP)
IRS Enrolled Agent (EA)
Certified Public Accountant (CPA)
Equity Compensation Associate (ECA)
Chartered Financial Analyst (CFA)
Chartered Retirement Plans Specialist (CRPS)
Masters in Business Administration (MBA)
Our team brings a wealth of experience - pun intended - from their previous employers, having spent time working at JP Morgan, TIAA, Vanguard, UBS, Wells Fargo, Credit Suisse, Goldman Sachs - amongst others. We hire only the most qualified, and aim to represent a diverse set of expertise to best serve our Members.
When your RSUs vest, they are treated as ordinary income based on the fair market value of the shares at vesting. Taxes are withheld, often at the supplemental rate of 22%, but this may not cover your actual tax liability, especially if you're in a higher tax bracket.
Yes, many companies allow you to adjust the withholding rate on your RSUs.
Increasing the withholding can help prevent a surprise tax bill when you file your return.
If you're selling all your RSU shares and have no upcoming vesting events within 30 days, wash sales may not be a concern. However, if you have regular vesting schedules, especially monthly, wash sales can become more complicated.
