US Immigration and Plymouth Street

Summary

This episode featured Lisa Wen, founder of Plymouth Street, discussing her journey building a tech-enabled service to streamline the US immigration process for technologists, especially through the little-known O-1A visa.
Key points included an overview of US employment-based immigration, the severe limitations of the H-1B lottery, and the opportunities afforded by the O-1A visa.
Lisa shared insights into Plymouth’s playbook for simplifying and accelerating immigration petitions, her personal motivation, and guidance on both grant funding and breaking into Silicon Valley as an outsider.
Attendees included host Turner Novak and Lisa Wen; the discussion covered actionable frameworks for productivity, hiring, and entrepreneurship.

The US has both employment-based and non-employment-based immigration systems. Plymouth Street focuses on employment-based options.
The H-1B visa is heavily oversubscribed and allocated via a random lottery, resulting in most qualified applicants losing out.
Several lesser-known visa categories exist, such as country-specific visas (e.g., TN, E-3), the J-1 for cultural exchange, and the O-1A for individuals with extraordinary ability in STEM/business.
The O-1A visa is uncapped, has faster processing, and is more accessible than most realize; applicants need to meet 3 out of 8 possible criteria.
Many more people (e.g., PhDs, accomplished engineers) are eligible for the O-1A than currently apply.

The US economy and technology sector benefit disproportionately from immigrant founders—55% of unicorn startups are immigrant-founded.
The lottery system creates risk and instability for highly skilled individuals and for US innovation.
Talented workers often take circuitous routes (e.g., via Canada) to get to the US due to immigration obstacles.
The O-1A visa provides a viable alternative but is underutilized (fewer than 5,000 STEM recipients per year).

Plymouth Street accelerates the O-1A application process: applications are prepared in 4 weeks (vs. 4 months with traditional law firms); premium processing yields decisions within 15 business days.
The service is designed to remove jargon and focus on clear, precise documentation aligned to O-1A criteria, resulting in a 99% approval rate.
The application process still requires mailing a 500-page physical document.
Pricing is competitive with traditional firms; the customer experience focus includes speed and guidance (not self-serve).
Lisa’s personal immigration struggles, including a visa rejection, motivated her to build Plymouth.
Early company funding came from philanthropic grants (not VC), notably from Schmidt Futures, Emergent Ventures, the Talent Mobility Fund, and others.

Plymouth has helped over 100 technologists secure O-1A visas, leading to the growth of a community that includes events and peer support.
The goal is to expand beyond immigration to become an onramp for immigrants building life and careers in the US, fostering a pay-it-forward ecosystem.

Lisa’s path: cold outreach, leveraging weak ties and introductions, and showing authentic, relevant experience in the technology sector.
Emphasis on hustle, clear storytelling in outreach, and showing value (e.g., identifying or fixing issues for a target company).
Advice for outsiders: build a relevant track record where you are, be proactive in reaching out, and demonstrate passion for the technology sector.

Hiring: focus on understanding candidates’ hopes and fears to align motivations, in addition to skills; use contract-to-hire for early team members.
Productivity: use frameworks like “write it down, make it happen,” daily/weekly to-do lists, and regular calendar audits to ensure time is spent on high-impact activities.
Lisa’s personal productivity hack: work primarily from her laptop to minimize distractions and maximize efficiency.

Make more visa categories “dual intent” to allow travel during green card processing.
Establish a FastTrack green card path for graduates from US universities.
Transition immigration petition filings to electronic submission.

Focus Plymouth Street on O-1A visa fast-tracking — Because of its uncapped nature, high approval rate, and underutilization among technologists.

Will US immigration policy evolve to better support high-talent immigration, such as expanding dual intent categories or enabling electronic filing?
How will Plymouth’s community evolve as they expand services beyond immigration?
What are the practical next steps for scaling the O-1A visa application process as demand grows?
No specific open or unresolved action items from the meeting.