1. Pick one narrow designer and one painful moment
Don't target all freelancers. Pick something like US-based freelance brand designers in their first or second year who just got a surprise tax bill or are facing their first quarterly estimated payment. That moment, usually around the quarterly estimated payment deadlines and in March and April, is when they will pay to make the pain stop.
2. Find them where they already complain
Search Reddit in r/freelance, r/graphic_design, r/UXDesign and r/tax for posts like "freelance designer taxes first year" or "1099 quarterly estimated taxes". Also search the Designer Hangout Slack, design Discord servers and Twitter/X for "freelance taxes" plus "designer". Save 30 people who posted about this in the last few months.
3. Help first, in public
Reply to their posts with a genuinely useful answer: which expenses designers commonly miss, like software subscriptions, a portion of their phone bill and font licenses, and how to set money aside each month. Mention a bookkeeper or CPA for anything complex. Only add one line at the end saying you're building a tool for this and happy to show them.
4. Send short direct messages
DM the people who posted recently. Example: "Saw your post about the surprise tax bill. I'm building a simple tool that pulls a freelance designer's income and expenses into one place and estimates quarterly taxes. Could I set you up free for 20 minutes this week and you tell me what's missing?" Send 10 a day.
5. Do the work by hand on a call
On the call, have them share their bank or Stripe/PayPal exports and organize their year with your tool while they watch. Fix gaps manually if the AI misses something. The goal is that they leave with a clean expense list and a quarterly estimate they trust.
6. Ask for money before the call ends
If they found it useful, say: "I'm charging a small founding price for the year, which includes me checking your categories before you send them to your accountant. Want in?" Send a Stripe payment link on the spot. A clear yes or no is more useful than "maybe later".
7. Reach designers through their accountants and peers
Ask every user for one designer friend who is also behind on taxes. Also message solo CPAs and bookkeepers on LinkedIn who list creative freelancers as clients: "Your designer clients probably send messy records. I organize them before they reach you. Want to try it with one client?"
8. Repeat daily and track replies
Keep a simple sheet: name, where you found them, message sent, reply, call, paid. Adjust your message weekly based on which line gets replies. Hulby, an AI cofounder, runs this finding and outreach work daily for founders who want help keeping it going.
People asking this right now
Real, public posts from the last few weeks. Each one is somebody you could help today.
Mistakes to skip
- Targeting all freelancers instead of one type of designer with one tax moment.
- Posting links in communities before helping anyone, which gets you banned.
- Giving tax advice you aren't qualified to give instead of pointing to a CPA for complex cases.
- Offering endless free trials instead of asking for payment after a useful call.
Want this done for your AI tax organizer for freelance designers, every day?
Hulby finds the people asking for what you built, writes every reply and email, and keeps you on it until they pay. Free to start.
Find my first customersQuestions
When is the best time to reach freelance designers?
Right before quarterly estimated tax deadlines and from January to April, when tax pain is fresh.
How much should I charge the first customer?
Pick a simple yearly price they can say yes to on the call. You can raise it later.
Do I need a finished product?
No. A working core plus manual help on a call is enough to get paid.
Is it risky to handle someone's tax data?
Yes. Ask only for what you need, explain how you store it, and say clearly that you organize records and aren't a tax preparer.