If everyone’s moving to Miami or Dubai, you probably just missed the opportunity.
The herd never gets outsized returns—especially in location. By the time Substack and LinkedIn are flooded with stories about Georgia (the country) or an exodus to Lisbon, the real rent gets baked in, the compliance sharks circle, and the easy edge vaporizes.
Here’s the reality: Founders obsessed with hype clusters are always two cycles too late. The most valuable long-term founders win by finding, exploiting, and compounding advantages in overlooked or “unsexy” geographies—before they’re cool.
While the crowd zags, the operators zig, quietly building empires in places others mock or ignore…until it’s too late.
Context/Problem: The Herd Mentality Is Your Worst Enemy in Geography
How Hype Clusters Became a Founder Trap
- 2014–2019: San Francisco = software kingmaking—then cost and competition kill all but the whales.
- 2020: Everyone says “Silicon Valley is dead”—Atlanta, Austin, Miami, Lisbon, Dubai see “Web3 bro” stampedes.
- 2022–2024: TikTokers push Georgia and Armenia as “the next digital gold rush” for nomads and crypto.
- Every time: By the time you hear about it, the arbitrage is gone.
- Cost of living doubles.
- Local compliance cracks down.
- Talent gets picked over or overpriced.
Fact:
In 2023–24, the “most discussed” startup cities (Miami, Lisbon, Dubai) saw cost of living for tech workers increase 50–120% in 24 months (Numbeo, LinkedIn Talent Trends 2024).
The Real Problem for Non-Standard Founders
- You can’t afford to follow the crowd. The more visible your play, the thinner your margin.
- By the time the legal/accounting/infra stack is “plug and play,” every drop-shipper and agency follows—until the “Dubai hack” becomes as commoditized as WeWork hotdesking in SF.
Operator Rule:
You compound returns when the rest of the table is still busy mocking your geography as “irrelevant.”
Framework/Solution: The Founder’s Contrarian Geography Stack
Stop chasing blogged-to-death locations. Here’s how to systematically identify (and exploit) real geographic opportunity before it’s “obvious.”
See how I invest my own money
My public portfolio, positions, and the boring strategy behind it.
View my investments1. Find Arbitrage While It's Unsexy
- Ignore “Best places for founders” lists—they’re lagging indicators.
- Hunt for:
- Emerging regulatory zones (pre-popular banking, pre-crowds)
- Drastically underpriced talent or services
- Pro-business but under-VC’d markets (e.g. Eastern/Central Europe 2016–21; LATAM SaaS, 2019–2023; Canada “second tier” cities right now)
- Use cold, bottom-up metrics (real estate, utility/infra costs, Stripe integration, real visa timelines)
- Run anti-consensus checks: If your top 20 founder friends would laugh at the city… that’s a positive sign.
2. Understand the Compounding Mechanisms
- Geo-blind markets: US/EU clients don’t care as long as deliverables arrive, so founders who build in “discount” cities retain 60%+ more margin (ANC portfolio data, 2024).
- First-mover local talent: Early operator founders can lock in engineer/design/ops talent at 20–30% of global rates, years before big companies flood supply (Stack Overflow Salaries 2024).
- Regulation lag: Operate in a window before everyone and their lawyer “figures out” the new tax/visa rules (previously true in Cyprus, Panama, Portugal, Latvia).
Operator Table: Arbitrage Decay Timeline
| Location | “Undiscovered” Window | Max Savings | Arbitrage Expiry Sign (months) |
|---|---|---|---|
| Tbilisi (Georgia) | 2018–2021 | 65% | Crypto wave, cost jump |
| Tallinn (Estonia) | 2014–2018 | 55% | e-residency gets mainstream |
| Porto (Portugal) | 2017–2021 | 48% | Nomad blogs, rental surge |
| Mexico City | 2015–2019, 2020–23 | 50% | EN Instagram, visa checks |
| Dubai | 2018–2021 | 40% | Twitter VC inflow, rent boom |
Data: ANC, Nomad List, Numbeo, Statista Urban Cost Index, 2014–2024
3. Exploit the Ignored “Second Cities”
- Never underestimate the power of being the first serious operator in a “tier 2” metro:
- Toronto → Hamilton
- Berlin → Leipzig
- Sydney → Adelaide
- US: Skip Austin—try Tulsa, Kansas City, or Asheville
- Early access to:
- City grants and incentives (that go unclaimed)
- Untapped local talent pools
- Absurdly cheap commercial space, hosting, infra
Fact:
60% of “second city” ANC clients in 2022–24 secured >$25k incentives or discounts not accessible in headline startup metros.
4. Anticipate the Inbound Herd—and Pre-Exit
- Plan your “in before the crowd” and your “out before oversaturation” move.
- As soon as you see global headhunter blasts, or WeWork openings, start building your exit or next lateral move.
- Document everything: infrastructure contacts, compliance steps, vendor contracts (early contracts mean better renewal leverage later).
Case Studies: Contrarian Moves That Paid Massive Dividends
Case 1: The Georgia SaaS Arbitrage (2019–2022)
- Solo founder ignored Lisbon/Dubai/Estonia hype—audited actual cost and digital infra from scratch.
- $950/month cost structure (one-bed, fast net, legal fees included)
- Outsourced frontend and CX support at 600/monthvs.600/monthvs.3k+ in Portugal.
- No “community,” but 5x more runway—bootstrapped to $900k ARR before “crypto expat” boom hit and rents spiked 3x in 12 months.
- Exited before the compliance hype—locked in 5-year personal capital gains rate.
Case 2: US Second City B2B Play (2021–2023)
- Group of agency founders skips Austin/Nashville, launches from Tulsa.
- Claims city business grants, 10kinannualinfracredits,10kinannualinfracredits,2,000/mo in rent savings.
- Outpositioned late-stage nomads as locals for government RFPs—won two $100k+ contracts unavailable to “remote” operators.
- Saw cost pressure rise 18 months later—pre-negotiated lease exit, rotated ops to Raleigh.
Case 3: LATAM B2B SaaS (2020–2024)
- Ignored Medellin hype, picked Monterrey, Mexico:
- Stable, business-friendly, $1,600/mo all-in cost for a 3-person team, deep local developer pool.
- US clients didn’t care—Stripe setup via Canada, tax handled by local CPA
- IPO-style exit at 37x TTM EBITDA, as competitor SaaS copied “Miami to CDMX” playbook and got killed by local tax rule changes.
Pull quote:
Being early feels lonely. It also feels like a 4x profit margin while the echo chamber fights for “community.”
Action Steps: Contrarian Geography Operator’s Audit
- Ignore TikTok, LinkedIn, or Top 10 Lists.
- Run bottom-up cost and banking analysis for your top 3 “unsexy” cities (real estate, Stripe/PayPal, legal, visa).
- Explore “second city” programs: Email economic development offices—ask for grants or credits (real, not PR).
- Audit arbitrage decay: Set calendar check-ins for rent, key talent, compliance news. If rent doubles, execute secondary move.
- Download the Contrarian Geography Audit Template: A table/checklist for opportunity scouting, decay timing, and local risk signals.
“There’s zero edge in being where the crowd goes. The only edge now is finding and monetizing the overlooked—before they get their Series A restaurant.”
CTA & Conversion:
When everyone is following, you’re just expense padding for landlords and regulators. Win by compounding before the blog posts—download the Contrarian Geography Audit, join ANC’s operator intelligence list, or book a diagnostic to chart your own zig.