How much did I actually make this week after gas and mileage? Is that expense deductible? What are my 1099 taxes going to look like? When should I drive, and which platform pays more right now?
Every gig worker and solopreneur carries some version of these questions. Until now, answering them meant opening five different apps and doing the math yourself. Sherpa changes that.
What is Sherpa?
Sherpa is an AI assistant built for gig workers and solopreneurs, available inside the Solo app on iOS and Android. Unlike a general-purpose chatbot, Sherpa is trained on the realities of independent work — rideshare, delivery, home services, freelance — and grounded in real marketplace earnings data across those verticals. Ask Sherpa what to work, what you made after expenses, or what your estimated self-employment taxes look like, and get answers calibrated to your actual numbers.
Why gig workers need a purpose-built AI, not a generic chatbot
Independent contractors have worked without the tools and data they need for too long. The platforms you work for run on proprietary algorithms and billions of data points to optimize pricing and demand. Those companies have unlocked earning opportunities — but they've kept the intelligence to themselves.
Sherpa puts that data, advanced analytics, and AI in the worker's hands — so you're no longer in the dark, alone, or left guessing.
ChatGPT doesn't know what a rideshare driver clears after gas and mileage. It doesn't know when delivery demand spikes in your city or which platform is paying better this week. Sherpa does — because it operates on real earnings data at a scale matching what the marketplaces themselves use.
Real gig earnings data from WorkSolo: $6B+ and growing
Sherpa is built on Solo's dataset of $6B+ in gig worker and solopreneur earnings across rideshare, delivery, home services, and more. That means it answers questions no general AI can:
- Which platforms are trending up in your market — see which apps are paying more this week, based on real earnings from workers in your city. Solo's Pay Insights track earnings data across 1,200+ cities.
- When demand peaks and when it drops — Sherpa reads demand patterns in your specific line of work so you can time your shifts for higher payouts.
- How your earnings compare — benchmark against real solopreneurs doing similar work in the current market, not outdated national averages.
- What workers are actually taking home — the kind of intelligence that used to live only in the heads of the most experienced drivers and couriers.
Mileage tracking, expense tracking, and tax estimates in one place
Most gig tools do one thing — track mileage, or log expenses, or estimate taxes. Sherpa connects all of it. Your earnings history, expenses, deductible miles, documents, and tax estimates all talk to each other inside Solo.
Solo's Mileage Tracker automatically logs your work miles using GPS — no manual entry. The 2026 IRS mileage rate is 76¢ per mile (effective July 1), and Sherpa applies the correct rate to your tracked miles so your deduction estimate stays current. For gig workers who drive thousands of miles a year, the mileage deduction alone can save hundreds or thousands in self-employment taxes.
Instead of opening five apps and doing the math yourself, ask one question in plain language and get an answer that accounts for your earnings across platforms, your deductible miles, and your projected quarterly taxes.
Your AI assistant for 1099 taxes and gig worker deductions
Taxes are where independent workers lose the most money. Sherpa continuously surfaces potential 1099 deductions, classifies your expenses, tracks work miles automatically, and keeps a running projection of what you owe — so there's no April surprise.
Common gig worker tax deductions Sherpa tracks include:
- Mileage deduction — at the current IRS rate of 76¢/mile, your tracked work miles convert directly to tax savings
- Phone and data plan — the business-use portion of your cell phone bill
- Supplies and equipment — phone mounts, chargers, insulated bags, cleaning supplies
- Vehicle expenses — if you use actual expenses instead of the standard mileage rate
- Self-employment tax — Sherpa estimates your SE tax liability based on your year-to-date net earnings
Ask "What can I deduct?" or "What are my estimated taxes this quarter?" and Sherpa answers using your actual numbers.
Real-time intelligence across driving, delivery, and beyond
Whether you drive for Uber, deliver for DoorDash, or run a home services business, Sherpa covers the full breadth of the solopreneur economy. Real-time event data plus years of historical trends mean you see the market as it is right now and where it's headed. Big game this weekend? A surge in local deliveries? A shift in platform incentives? Sherpa tells you what it means for your schedule and your earnings.
The most important data point is always you
Market intelligence is just the starting point. What makes Sherpa powerful is that it brings your whole professional picture into one place. This is earnings aggregation across every gig platform, unified so you see your real numbers — not a dashboard of disconnected metrics.
The result is advice calibrated to your patterns and preferences:
- Earn more — Sherpa identifies the highest-value shifts and opportunities in your market so you make the most of your time or hit an earnings goal.
- Keep more — it surfaces deductions, tracks your work miles, provides tax estimates, and flags financial gaps before they become surprises.
- Stress less — it answers the questions that used to keep you up at night, with numbers, not guesses.
- Always personal — every answer is calibrated to your specific platforms, patterns, and goals.
What's next for Sherpa
Over time, Sherpa will become a more active agent that guides you through your professional and financial life — built on a data platform spanning market rates, shift schedules, open roles, job prices, and geographic data. That means help finding new job opportunities, building a schedule that meets your budget, securing better auto loans and insurance, and preparing your taxes with free tax filing powered by April (free tax filing is included with annual Pro/Pro Plus subscriptions).
The Year of the Solopreneur
When we set out to make 2026 the Year of the Solopreneur, this is what we had in mind — not just better tools, but ones that understand what you're working toward and help you get there faster.
Sherpa is available now inside Solo. Download Solo free on iOS or Android, open Sherpa, and ask it anything.
Frequently asked questions
What is Sherpa?
Sherpa is an AI assistant built for gig workers and solopreneurs, available inside Solo on iOS and Android. It combines $6B+ of real gig-earnings data with your own earnings, miles, expenses, and tax estimates to give personalized answers about what to work, how much you'll make, and what you'll owe in taxes.
How much does Sherpa cost?
Sherpa is available inside Solo, which is free to download on iOS and Android.
What gig platforms does Sherpa support?
Sherpa covers the full solopreneur economy — rideshare (Uber, Lyft), delivery (DoorDash, Instacart, Grubhub), home services, and more. It aggregates your earnings across every gig platform you work so you see your complete financial picture in one place.
Can Sherpa help with gig worker taxes and 1099 deductions?
Yes. Sherpa surfaces and classifies deductions, tracks your work miles using Solo's automatic Mileage Tracker, and provides ongoing self-employment tax estimates so you can plan ahead and avoid surprises at tax time.
Does Sherpa track mileage automatically?
Yes. Solo's Mileage Tracker uses GPS to log your work miles automatically — no manual entry needed. Sherpa applies the current IRS mileage rate (76¢/mile as of July 1, 2026) to your tracked miles so your deduction estimate stays accurate.
How is Sherpa different from ChatGPT or other AI tools?
Generic AI tools don't know your earnings, miles, or local gig market. Sherpa is grounded in $6B+ of real marketplace earnings data and your personal financial picture, so its answers are specific to your work — not generic tax advice or gig tips pulled from the internet.
Is Sherpa a self-employment tax calculator?
Sherpa keeps a running estimate of your self-employment tax liability based on your year-to-date net earnings, tracked miles, and classified deductions. Ask "What are my estimated taxes?" anytime and get a number based on your actual data.
What is the best app for gig workers to track earnings?
Solo with Sherpa is designed to be the single app for gig workers and solopreneurs who want earnings intelligence, automatic mileage tracking, expense classification, and tax guidance in one place — all powered by AI and $6B+ in real gig-earnings data.
