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.

​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

​🔘 6:00 PM — Doors Open · Registration · Light Food & Drinks

​🩷 6:30 PM — What U.S. VCs Actually Look for in Canadian Founders · Speaker - Damilare Odumosu CEO/Founder of Cropmind Inc

​🟣 7:00 PM — Cross-Border Legal: Structure Your Company the Right Way + Q&A

​🟡 7:20 PM — Immigration Strategy — O-1A/TN/L-1A/E-2 Speaker: Olga Prygoda Managing Attorney Stelmakh and Associates Business Immigration Law Firm

​🟢 7:30 PM — Rolla Demo + Networking + Drinks ·

​Sponsors — Foundhers × Black Women Talk Tech

​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.

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