A buddy of mine spent six months planning his move to Portugal. Visa research, the whole thing. He made the move and thought he had it figured out.
Three months later he had a tax residency problem in two countries and a bank account frozen over an address mismatch.
So I looked into it and found a business idea worth building.
In Todays Edition, TL;DR
35 million people got the nomad visa and walked straight into a compliance nightmare nobody warned them about
how to win your first government contract using Claude with no experience and no money
a savings app idea where your AI companion lives or dies by your spending habits
the tools and moves worth your attention this week
The Friday Idea
💡 Papertrail: A tax and compliance coordination platform for cross-border remote workers
The Problem: Did you know theres are roughly 35 million digital nomads worldwide. That number has tripled since 2019. Over 50 countries now offer dedicated nomad visas.
However… getting the visa is the easy part. It's what the visa unlocks that nobody prepared you for.
Most nomads piece together their compliance situation from a Reddit thread or a Facebook group. The result?
Tax residency in two places at once, banking locked from address inconsistencies, and client contracts creating legal exposure in jurisdictions they've never heard of.
🛠 Solution: Think TurboTax meets a personal CFO for the person living country to country. Papertrail coordinates the full compliance picture in one place. User inputs their country, tax residency status, client locations, and banking setup. The platform maps their exposure across tax treaties, banking requirements, and contract risk.
Business Model:
Free option: Visa tracker and basic tax residency calendar. Entry point. No friction.
Pro option: Full compliance dashboard, treaty mapping, banking compatibility checker, contract risk flags.
Concierge add on: Matched referrals to vetted expat tax specialists and international legal professionals. Platform takes a referral fee per completed engagement.
The Exit: Deel, Remote, or Rippling would each absorb this. They've built the employer of record infrastructure for global remote work. The missing piece is individual worker compliance on the other side of that equation. This becomes the consumer layer they don't have.
Founder Tutorial
How to win your first government contract using Claude (no experience required)
The concept: find an open government contract on SAM.gov, drop the solicitation into Claude, and let it tell you exactly what to bid on, how to price it, and what to write in your proposal. The whole thing takes under an hour.
Heres the video explaining how to do this 👇🏻
Tutorial | TL;DR version
What you need
SAM.gov (free). Claude (free tier works). An LLC. That's it.
Step 1: Register on SAM.gov
Go to sam.gov and register your business for free. Name your LLC something generic so you're not boxed into one industry. Once registered, you can bid on anything.
Step 2: Find a contract
Filter for service contracts under 350k. Below that threshold the government doesn't ask for past performance. They just want a quote. Look for something you can understand in plain English and skip anything with 20 attachments.
Step 3: Drop the solicitation into Claude
Download all attachments. Open a Claude Project. Upload everything. Prompt it: "You are an expert in government contracting. What is being asked for, what are the submission requirements, and what do I need to submit a competitive proposal." Plain English breakdown in thirty seconds.
Step 4: Price the bid
Call subcontractors. Get a quote. Look up what the government paid for the same contract type on usaspending.gov. Put your margin on top and submit.
Step 5: Let Claude write the proposal
Prompt it: "Based on the solicitation, write a compliant proposal. My company will subcontract the work to a local provider." Review it. Submit it.
One contract. Five years of recurring income. An hour a month to maintain.
Napkin Note Ideas
💡 Petworth: A savings app where your AI companion lives or dies by your spending habits
The Problem: Can you believe the average American has under fifteen hundred dollars in savings? Sixty percent live paycheck to paycheck. Mint had 25 million users and shut down because tracking spending never actually changed it.
Knowing you're bad with money turns out to be insufficient motivation, who knew.
Tamagotchi got nineties kids sprinting home to feed a digital chicken. Duolingo built a twenty billion dollar company on grammar guilt and a passive aggressive owl.
The concept works. Nobody applied it to a bank account.
The Solution: Petworth connects to your bank and lets you set a monthly savings target and assigns you an AI companion whose health is tied directly to your habits. Crushing your goal? They're thriving, glowing, sending you celebratory voice notes. Slipping and they look exhausted, anxious, and start sending concerned check ins.
The dashboard tells you the numbers. The character tells you how bad it actually is.
Business model:
Free option with one character and basic spending breakdown
Pro plan unlocks additional characters, personality types, and behavioral insights
Financial product referrals (HYSA, credit cards) for users who hit savings milestones
Weekly Gems Worth Reading
OpenAI just launched Daybreak, AI agents for finding vulnerabilities and validating fixes inside code.
a $100M founder told us his exact meta ads strategy on mic, watch the full thing here
Khosla Ventures is betting $10M on Ian Crosby. BTW his last startup, Bench Accounting famously imploded in 2024. Second times a charm?
That’s all guys
That's Friday. A compliance coordination tool for the 35 million people who figured out the visa and nothing after it, a Claude workflow that turns government contracts into recurring income, and a savings app built on the only motivation that actually works.
Decent weekend to register an LLC.
Talk Monday.