The Playmakers: Canadian founders → U.S. Capital: The Cross-Border Playbook
The Cross-Border Startup Playbook
Toronto Tech Week
Join us for a tactical evening on how Canadian founders actually raise from U.S. investors — and structure their companies correctly before they pitch.
This is the room every Canadian founder needs before stepping into a U.S. VC meeting.
Hear directly from investors who’ve backed Canadian startups, a cross-border startup lawyer, and an immigration expert. Walk away with a clear playbook to expand south, raise American capital, and relocate yourself or your team when the time is right.
No fluff. Just execution.
An off-the-record evening for Canadian founders, operators, and investors on what it actually takes to raise from U.S. funds in 2026.
About Rolla:
Rolla is a global bank and identity security platform for remote teams. Combining USD/CAD wallets, cross-border payouts to 190+ countries, contractor payroll, and Rolla IDx — AI-powered reusable identity.
About Gold Pass Visas:
Gold Pass Visas helps entrepreneurs and business owners expand into the United States through strategic visa pathways like O-1A, L-1A and E-2. We go beyond immigration paperwork—combining business setup, compliance, and market entry support to help you launch, operate, and grow your U.S. presence with confidence.
Agenda
5:30 PM – Doors Open + Registration + Light food and Drinks
6:00 PM – Welcome + Host Intro
6:20 PM – Investor Panel
What U.S. VCs actually look for in Canadian founders
Market positioning
Delaware setup
Metrics that move deals
Valuation expectations
6:50 PM – Cross-Border Legal Session
Structuring your company the right way
Delaware C-Corp vs Canadian structure
SAFE strategy
Cap table hygiene
Avoiding costly mistakes
Open Q&A – 5 minutes
7:00 PM – Immigration Strategy by Gold Pass Visas
Move yourself and your team legally
U.S. Founder Visa Pathways: O-1A, TN, L-1A, E-2
Which visa fits your stage and timeline
L-1A for intracompany transfers
TN for eligible CUSMA roles
Open Q&A – 5 minutes
7:20 PM – Rolla Demo + Closing
How global payments and identity infrastructure support cross-border expansion
7:30 PM – Networking
We are officially part of Toronto Tech Week 2026, a weeklong citywide collection of events to connect and celebrate the builders. May 25 → May 29, 2026 | torontotechweek.com.