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.