US Expansion Legal Update with Allan Rooney

However, entering the US presents unique legal challenges that companies must navigate carefully to avoid costly mistakes. From setting up the right legal entity to understanding tax implications and protecting intellectual property, numerous legal considerations exist to address.

Bill Kenney:
Hi, and welcome to the next episode of Belly2Belly. Today, we’re joined by my good friend Allan Rooney from Rooney Law. As you can imagine, our topic today is U.S. expansion legal updates. Our audience consists of companies that have either expanded into the U.S. from abroad or are planning to do so. Before we dive into the topic, Alan, could you take a minute to tell us a little about Rooney Law and the work you do for companies expanding into the U.S.?

Allan Rooney:
Absolutely, Bill. Thanks for having me, and thank you to everyone tuning in. We’re excited to be here. I founded Rooney Law in 2007 as a boutique firm based in the New York City area, with a team spread across the U.S. We work with a variety of businesses, primarily focusing on corporate and business law. Over the years, we’ve helped around 300 companies expand into the U.S., especially those from markets like the UK, Ireland, and Australia. We’ve gained a lot of experience working with businesses across different sectors and entry strategies. Our goal is to support the legal needs of companies entering the U.S. market and help them integrate into the business ecosystem here through introductions and other resources.

Bill Kenney:
That’s fantastic. With the 300 companies you’ve worked with, what are some of the common challenges you’ve seen them face during their expansion into the U.S.? Where do they typically struggle?

Allan Rooney:
I’d say the challenges can be grouped into two buckets: legal and business. From a business perspective, there’s always an element of execution risk. Did they hire the right people? Is the timing right? These are questions businesses must address. The economic climate matters—are they entering during boom times or a downturn? As for legal pitfalls, I often see mistakes like improper setup or tax issues that companies weren’t prepared for. The U.S. market is complex, and it’s essential to seek advice, not just legal, but business guidance too. The cost of fixing a legal problem down the road is often far higher than getting the right advice upfront. For example, we’ve seen clients embroiled in expensive litigation over poorly drafted distribution agreements that could have been avoided with better legal counsel. Similarly, issues like trademark disputes can blindside companies that think they’re safe but later find themselves accused of infringing on someone else’s intellectual property.

From a business perspective, companies need to think about how to crack the U.S. market. Do they bring over their founders or hire locally? We’ve seen that companies that bring over some key team members from their home country, in combination with U.S. hires, tend to perform better. Compensation is often higher in the U.S., especially in places like New York, but the rewards are there if done right. Investing in the right talent and being willing to take on financial risk is essential. It’s also crucial to have the executive bandwidth to support the U.S. operations—don’t neglect your home market while trying to grow in the U.S.

Bill Kenney:
Right. And I think you’re highlighting exactly the things we see in our work with scaling companies. You’ve mentioned the challenges. Now, one question we get from early-stage companies is when should they establish a legal U.S. entity? There are different factors at play here, but could you provide some general guidelines on when a company should think about forming a U.S. entity?

Allan Rooney:
That’s a great question, and one we get a lot. Companies often wonder if they really need a U.S. entity early on, or if they can just rely on a representative office or some other informal setup. I always try to demystify this because establishing a U.S. entity isn’t that difficult or expensive, and the limited liability protection it provides is invaluable, especially in a litigious environment like the U.S. Even if your costs are only a few thousand dollars annually for tax filings and accounting, the protection you gain is well worth it.

In terms of timing, it’s often a combination of factors. Maybe you’ve landed a major client or formed a strategic partnership—these milestones can make it clear that it’s time to formalize your presence here. Alternatively, it could be that a key team member is moving to the U.S. on a work visa, and suddenly you have the resources to open an entity. Another scenario might be an opportunistic decision, where you see the chance to set up a presence in a new market, like Atlanta, and take advantage of that opening.

But overall, I always advise companies to do it early, even if they’re just testing the waters. You can always dissolve the entity later if things don’t work out, but the protection and tax benefits are worth the effort. Plus, it’s easier to navigate contracts, payroll, and potential legal issues with a U.S. entity in place.

Bill Kenney:
Absolutely. We’ve always said, even without legal training, that it’s crucial to consult an attorney. But hearing your perspective, especially on when to form the U.S. entity, really helps. Now, looking back on the companies you’ve worked with, what characteristics do you see in the most successful founders? What sets them apart?

Allan Rooney:
Great question. I’ve worked with a lot of entrepreneurs, and I’ve found that those who succeed in the U.S. share a few key traits. First and foremost, they embrace the “sky’s the limit” attitude that is so common in the U.S. When I first came here as an exchange student, I was struck by how much opportunity there is, and the most successful founders really seize that mindset. They recognize the potential of the U.S. market and aren’t afraid to leverage their background—whether it’s their accent, their company’s story, or their product—to build trust and gain access.

Another important trait is confidence. In the U.S., especially in places like New York, people are willing to give you a chance if you can show you’re interesting and can bring value to the table. That means being comfortable with rejection and learning from it, but also having the persistence to keep pushing forward. There are cultural differences to be aware of, especially if you’re coming from a place like the UK. For example, self-deprecating humor, which is common in the UK, can be misinterpreted here. Americans tend to be more direct and confident in their pitch. So, understanding and adapting to the local culture can make a huge difference in building relationships.

Bill Kenney:
That’s great advice. So, any parting words for companies thinking about expanding to the U.S.?

Allan Rooney:
Yes, one thing I’d say is that building a strong network is critical. Seek advice from trusted sources and tap into resources like government trade desks or organizations like Enterprise Ireland, which can help connect you with local contacts. Networking is key—ask for introductions, because Americans are generally very open to helping others connect. Just be clear on what you need, whether it’s legal advice, an accountant, or something else. Having a short list of priorities will help you leverage the network more effectively. It takes time and persistence, but the opportunity here is worth it.

Bill Kenney:
Fantastic. Alan, thank you so much for your time today. It’s been incredibly valuable. Can I include your contact info in the description below?

Allan Rooney:
Of course, Bill. Thanks for having me. Happy holidays to everyone!

Bill Kenney:
Thank you! We’ll talk soon.

For More on This Topic

Read our previous legal update with Dan Glaser from Wilson Sonsini.

About

MEET helps international B2B & B2G companies gain traction and scale in the U.S. through trade shows, events, and strategic connections. Contact Bill Kenney for a no-obligation conversation:  bill@meetroi.com or +1 (860) 573-4821.