Glen Caplan, Partner, Robinson Bradshaw

Invest: spoke with Glen Caplan, partner at corporate law firm Robinson Bradshaw, about how AI is reshaping the capital needs of technology companies, why the Triangle remains a strong market for innovation, and how entrepreneurs can position themselves for growth. “Quality wins, and if you have a compelling business with strong customer demand, then money finds you,” Caplan said.

What changes over the past year have most impacted your clients, and how are companies adjusting to those shifts?

Most of my clients are software and technology companies, so they are going through a dramatic revolution with AI. At this point, every company has to have an AI solution that it is integrating into its products, or it has to reinvent itself around AI. When I talk about AI, I am thinking both about generative AI, such as ChatGPT and Claude, and also agentic AI, using agents to do things that humans historically handled or that software once completed through longer processes.

It is probably the biggest shift I have seen in my 25-year career. It is transformative, and it is exciting. Companies are moving quickly to understand how these tools can improve their products, operations, and competitiveness. The question now is no longer whether AI matters. It is how fast companies can adapt and how effectively they can implement it.

How would you describe the environment for business growth and investment, and what are founders and investors most focused on today?

This area continues to be a great place for business. We see a lot of opportunity here, driven by a highly educated and highly skilled workforce and by continued in-migration from other regions. Access to capital is also strong. Twenty years ago, it was difficult to get out-of-state venture investors to spend time looking at this market. Since the pandemic, that has changed significantly. Investors are far more open to backing companies remotely and no longer feel they need to be able to drop into an office every month to check on a portfolio company.

That shift has created more opportunities for growth companies in this region. I am bullish on where the Triangle is headed. There is still a tremendous amount of opportunity ahead, and founders and investors alike are focused on how to build businesses that can scale efficiently in a market that continues to attract talent and capital.

What trends are shaping how companies raise capital and structure their business in today’s market?

One of the biggest trends is capital efficiency. Because of the gains AI is making in software development, companies can do much more with much less. What used to require a team of 10 engineers can now sometimes be done by one. I have clients building sophisticated products that, even five years ago, would have required them to raise $10 million or $15 million. Today, some of them are doing it with less than $1 million because of these development efficiencies.

I have one client with just two founders who told me that a few years ago they would have needed 10 or 15 engineers to build what they are building today. Instead, the two of them are doing it themselves. That is a dramatic change, and it is affecting how companies think about structure, hiring, and fundraising from the beginning.

As a result, I think companies are going to move from inception to exit much faster than they have historically. Businesses can get to product, market traction, and scale more quickly, and that is changing the entire pace of the life cycle.

What are the most common challenges you are seeing across different stages of a company’s life cycle?

For more established companies, especially those that are not AI-native, the challenge is that the investment community is so focused on AI that it is discounting the valuation of businesses that may still be strong, profitable, and well-run. If a company has been around for 10 years or more and is not viewed as part of that AI wave, that can create a real headwind.

For earlier-stage companies, the Triangle has a strong investor community, but the move from seed funding to Series A funding and beyond can still be difficult. We do not have many local Series A investors based in North Carolina, although we have some excellent ones in Cofounders Capital, Bull City Venture Partners, and IDEA Fund Partners, among others, so as companies mature and need to raise larger amounts of capital, they often have to look outside the region.

It is becoming less of an obstacle than it used to be, but it is still a challenge. It is naturally easier to raise money from people in your own community, people who know you and have watched your progress. When you go outside the market, you need to educate new investors. Still, quality wins, and if you have a really strong business, then money finds you.

How has the role of legal counsel evolved as companies navigate a more complex business and regulatory environment?

I do not know that my role has fundamentally changed, but I am seeing clients become more proactive in using AI tools to try to do their own legal research and contract review. The issue is that the results these tools bring back are not always accurate. They can sound persuasive, but that does not mean the analysis is reliable.

That means experience still matters. You need background in the underlying material to know whether what you are reading is actually correct. At the core, our job remains the same. We are here to provide high-quality counsel, efficient service, help clients understand the landscape based on the deals we have seen over the years, and guide them through important decisions.

One of the more underrated parts of the job is also helping make human connections. We are not investment bankers, but we know the investor community, and helping connect companies with investors or other strategic partners is a meaningful part of what we do.

What patterns are you seeing in how companies approach partnerships, transactions, and long-term value creation?

The biggest change is that, since the pandemic, many of the barriers to doing business remotely have lowered. Companies are striking partnerships all over the world, and the idea of a distributed team is the new normal. I have several clients that are headquartered in North Carolina, with leadership teams based here, but with workforces spread across the country or across the globe.

That broader, more virtual approach is changing how businesses think about growth and collaboration. Companies are no longer constrained in the same way by geography, whether they are hiring talent, working with partners, or building customer relationships.

What opportunities are emerging for innovation-driven companies in today’s environment?

AI is opening the door for many more people to become entrepreneurs. It is simply not as difficult as it once was to build a technology product and company. I know of a nontechnical founder who created a business that downloads podcasts, transcribes them, and sends subscribers a daily digest. That person had no technical background and stood the business up in about three weeks.

That is a remarkable shift. It means innovation is no longer limited to people with deep engineering expertise or large amounts of capital. More people can bring ideas to market, test them, and build businesses around them.

Looking ahead, what are your top priorities in advising clients, and how do you see the broader business and investment landscape evolving over the next three to five years?

I am bullish on this region. The Triangle has a business-forward mindset, strong institutional ties, and a growing list of large companies that are relocating here. The region is also attracting talent from California, New York, and Massachusetts, among many others. Some people are moving for lifestyle reasons, some for cost of living, and some because remote work gives them more flexibility, but the result is the same: more experienced talent is landing here.

This is the brightest future I have seen for the region since I moved here in 2005. That is exciting.

When it comes to advising clients, my priority is helping entrepreneurs stay nimble because everything is changing quickly. Most of my clients are building businesses around novel intellectual property that require outside capital to rapidly scale, so a big part of my role is helping them position themselves to raise that capital effectively. The goal is to give them the best opportunity to build the business they envision and create strong returns for them and their investors.

What makes North Carolina especially compelling is that it supports the full spectrum of the business world. It is hospitable to nascent companies, but it is also home to major corporations and sophisticated capital providers. You can see the whole value chain here, from limited partners investing in funds, to funds backing startups, to those startups growing and ultimately being acquired by larger strategic or financial buyers. That full-stack ecosystem makes this an exciting place to build.