Navigating U.S. Immigration & Startup Visas for Canadian Founders

Join Adriana Soto Ospina, a digital health entrepreneur and expert in cross-border business development, together with Ankur Sethi, Venture Capitalist & startup advisor, for a practical conversation about how Canadian founders can approach U.S. immigration pathways and the startup visa process.

Whether you’re exploring expansion, preparing to fundraise in the U.S., or simply want to understand your options, this session will give you a clear, founder-friendly overview without legal jargon.

What We’ll Cover

💡 Overview of U.S. immigration pathways for founders

— including O-1, E-2, H-1B, EB-1A, and other routes relevant to high-growth entrepreneurs.

🌎 Understanding the “startup visa” concept

— what exists, what doesn’t, and how founders are navigating current frameworks.

🚀 What Canadian startups need before entering the U.S. market

— traction, evidence, storytelling, and investor expectations.

📈 How immigration strategy connects to fundraising and expansion

— timing, risk reduction, and what U.S. VCs look for in cross-border teams.

❓ Live Q&A

Bring your questions — we’ll leave time to discuss specific scenarios and founder experiences.

Who Should Attend

• Canadian founders preparing to enter or test the U.S. market

• Startups planning to raise from U.S. venture capital

• Entrepreneurs considering relocation or building cross-border teams

• Anyone curious about realistic pathways for founders entering the U.S.

Agenda

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Speaker

Ankur Sethi - Winner Capital (Founder and General Partner)

Ankur Sethi is the Founder and General Partner of Winner Capital, a Toronto-based early-stage venture fund backing the next generation of North American consumer technology companies. He has over 17 years of experience as a consumer tech operator, having built and scaled three companies from inception to $100M+ in revenue, with one reaching a valuation above $2B.
His investment the…

Hosted By

Ankur Sethi, Director

Ankur Sethi is a seasoned entrepreneur and venture capitalist with over 17 years of experience building and scaling consumer businesses across technology, finance, and healthcare. He has led ventures from inception to over $350 million in annual revenue and $2 billion in valuation, combining operational excellence with a deep understanding of evolving consumer behavior.

Daria Tilikanova, Co-Director

Daria Tilikanova is a business and startup coach who helps founders and service-based entrepreneurs build scalable businesses with clear strategy, strong positioning, and predictable revenue systems.

Originally from Russia, she founded and sold two education companies before moving to Canada, where she shifted into full-time mentoring for early-stage and growing founders.

Daria has worked with 200+ entrepreneurs across tech, education, wellness, and agency-based businesses, guiding them from first clients to stable growth and team building. Alongside her private practice, she is a Venture Fellow at Winner Capital, supporting startup evaluation and founder readiness for investment.

Her coaching combines business structure, mindset work, and execution clarity - helping entrepreneurs grow without burnout or chaos.

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Partner

Winner Capital (https://winner.capital)
Winner Capital is an early stage to growth stage syndicate fund investing across North America

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Startup Grind is a global startup community designed to educate, inspire, and connect entrepreneurs. We host monthly events in more than 600 cities and 125+ countries featuring successful local founders, innovators, educators and investors who share personal stories and lessons learned on the road to building great companies. Our monthly fireside chat interviews, startup mixers and annual conferences provide ample opportunities to connect with amazing startups and the people behind them, tap into a strong support network, form meaningful connections and gain inspiration for the startup journey ahead. For more information visit StartupGrind.com or follow us on twitter @StartupGrind.

Complete your event RSVP here: https://www.startupgrind.com/events/details/startup-grind-toronto-presents-navigating-us-immigration-amp-startup-visas-for-canadian-founders-2025-12-10/.