Pioneer Square Labs

Jul 31, 2025

But there are ways to successfully manage both. In an event called “Entrepreneurial Unlock: How to go from H-1B to CEO,” a panel of experts on Tuesday provided paths for gaining necessary visas without relying solely on luck-based lotteries and employer support, while also cautioning against potential pitfalls. The conversation was part of Seattle Tech Week , a five-day conference running through Aug. 1 and featuring nearly 100 meetups around the region. The goal of the immigration-focused panel, said Xiao Wang , CEO and founder of Boundless Immigration , was to empower people on their journey to work in the U.S. and potentially gain citizenship, which can take many years to complete. It's helping people, Wang said, “live the life that you want, where you want, doing the work that you love, and to try to take all of that chance out of the equation and take things into your control.” RELATED: Immigration crackdown rattles tech employers and workers amid ICE raids The timing is significant. Since President Trump returned to office, the immigration process has become more challenging. The backlog of pending visa cases has swelled, wait times are increasing, and approval rates have slightly declined for employment-based immigration, according to research by Boundless. Participants of the session included moderator Vivek Ladsariya , managing director at Pioneer Square Labs (PSL) , and panelists Hendrik Pretorius , director of immigration strategy and partnerships at Boundless; Britt Provost , chief HR officer for Siteimprove Ankit Dhawan , founder of BluePill AI ; and Lisa Wehden , founder of the immigration startup Plymouth The event was hosted by Boundless, PSL and JP Morgan and held at the Smith Tower. Here was some of their advice: Take control of the process. Many foreign-born workers are using H-1B visas that are annually awarded by lottery for eligible candidates, but that route is dependent on luck and support from employers. To be successful, workers should explore additional options for visas and green cards that fit their needs and qualifications. Consider other visa options. That includes O-1 and EB-1A visas awarded to individuals who demonstrate extraordinary abilities in their field and allow immigrants to work as startup founders. Wehden advised that applicants need to shed some humility that might have held sway in their native countries. “I talk to people who are incredibly modest and say, ‘I'm not extraordinary, I don't believe this visa pathway's for me.' And I totally get it, but we're in America now, so you have to sell yourself,” she said. Boosting one's professional profile. It might be that an individual doesn't immediately tick all of the boxes for O-1 and EB-1A visas, but they can work towards the qualifications. That includes activities such as presenting at events, judging contests and hackathons, receiving media coverage, publishing academic papers and demonstrating leadership in a field. Learn the fine print. Visas have different quirks and rules. If someone with an O-1 visa who has applied for a change of status or an extension travels outside the U.S., for example, that can delay the immigration process. H1-B green cards don't explicitly allow people to “moonlight” or work on their own startups while sponsored by an employer. Entrepreneurs with H1-B status can do research for their startup, but need to proceed cautiously. That includes not accepting any customer payments, and using only personal and not work-issued devices to avoid intellectual property conflicts. Seek trusted relationships. Securing visas and green cards are not solo efforts. It's key to find trusted legal support and to build relationships with workplace managers who can provide references that bolster an applicant's professional claims. “These are hard, emotional experiences for everybody. You're moving yourself, you're moving your family. You've got all these other things you're dealing with,” Provost said. “So work with people you trust.” Prep for expenses. Immigration costs add up — but are likely more affordable with the help of companies including Boundless, Plymouth and the recently launched Casium . Services vary between companies and Pretorius gave a range of $10,000-$30,000 or more for Boundless customers, while Wehden gave a price tag of $5,000-$13,000 for Plymouth. There are additional costs charged by the U.S. government. While that adds up, one event participant said he spent closer to $100,000 on the process, which he navigated before these companies existed, and included his own missteps.