Coffee, Contracts, and Capital: A Fireside Chat with VC Deborah Hemingway and Attorney Nick Stewart Offers Straight Talk for Startups

What do you get when a venture capitalist and her longtime attorney sit down for a fireside chat in front of a room full of founders?

Apparently, ghosting stories, early-morning treadmill negotiations, and some of the most practical startup advice you don’t hear often enough.

At the latest Entrepreneur Seminar Series event hosted by Ecphora Capital, venture investor Deborah Hemingway, Managing Partner of Ecphora Capital, joined Duane Morris Partner Nick Stewart for a refreshingly candid discussion on how founders should think about legal strategy, capital raises, and the elusive art of building real trust with their lawyers.

The session, titled “Investor-Ready: Legal Moves for Securing Funding and Scaling Fast,” wasn’t your typical legal download. It was part real talk, part startup therapy, and part survival guide for early-stage entrepreneurs navigating today’s volatile venture landscape. Packed with hard truths, legal hacks, and engaging banter, the event lit up Baltimore’s medtech ecosystem and might just reshape how early-stage founders choose their legal partners moving forward.

A Professional Relationship That Didn’t Start With a Contract But a Ghosting

The conversation kicked off with Hemingway and Stewart recalling their first meeting nearly a decade ago at a networking event and horse race in Baltimore County and how Hemingway promptly ignored Stewart’s follow-up coffee invite.

“I thought, ‘Here we go, another attorney trying to get money out of me,’” she said.

Stewart, laughing, confirmed, “And then you ghosted me. Many times.”

That moment of humor set the tone for a discussion that was smart, self-aware, and surprisingly inspirational. What followed was a rapid-fire, no-BS exchange on what founders should really be looking for in legal counsel: responsiveness, adaptability, and someone who doesn't bill every phone call like it’s an SEC filing.

Lessons for Founders: What to Look for in a Legal Partner

Both Hemingway and Stewart emphasized that maximizing the attorney-client relationship isn’t just about documents, though that is, of course, important. It’s about alignment, responsiveness, and showing up when it matters most. The strongest and most productive attorney-client relationships are built on a foundation of long-term trust and support.

“Trust is just consistency over time,” Hemingway said. “Especially in this work, where you’re constantly making high-stakes decisions with limited information and often limited sleep.”

From Stewart: “If you can’t call your lawyer without fearing the bill, that’s a problem. You need someone who gives you the green light before something becomes a red flag.”

The duo touched on everything from using NVCA templates to avoid “off-market chaos” to negotiating alternative fee structures that actually work for pre-revenue companies. Founders scribbled notes and laughed knowingly at the all-too-familiar mention of the dreaded five-hour, two-sentence invoice.

“It doesn’t have to be like that,” Hemingway added. “You need someone who you can call without hesitation. Someone who picks up the phone.” 

They even shared a recent example that underscored just how aligned they’ve become. “We had a situation earlier this week where a good thing was turning into a bad thing pretty quickly,” Stewart said. “And we needed to find time to hop on the phone. At 5:30 a.m.”

“Yes, that is correct — 5:30 a.m.,” Hemingway confirmed. 

“And I happened to be on a treadmill,” Stewart continued. “That was fine too.” The room laughed, but the point landed: real support doesn’t always clock in at 9 a.m. Real support shows up when you need it most. 

Scaling in a Market That’s Anything But Stable

In a twist that would make even the coldest corporate counsel lean in, Hemingway and Stewart’s candor made legal advice feel… human.

As the conversation turned to today’s venture climate, both acknowledged that we’re still in choppy waters.

“We’re not through the reset yet,” Hemingway said. “Valuations are still recalibrating, and founders are under pressure to do more with less.”

Stewart added that many firms are reevaluating their internal models, especially as they approach the end of their investment periods. “If you don’t deploy that capital, you wind down. Full stop. That’s forcing new urgency and creativity.”

They tackled the tension between founder and investor interests, the limitations of angel funding, and the startup realities of SBIR grants drying up. “This is a dynamic time,” Stewart said. “Founders are recalibrating, funds are adapting, and we need legal partners who are ready to move fast. Not write letters like it’s 1986.”

He even addressed the looming presence of AI in legal work, embracing it, not fearing it. “AI should eat my lunch,” he declared, explaining how tech is streamlining tasks like contract review and freeing up lawyers to focus on strategy and the more nuanced, human aspects of the profession.

The Long Game: Building the Firm Maryland Needs

One of the most resonant moments of the event came when Stewart and Hemingway delved into the future opportunity before them. Hemingway laid out her vision for Ecphora Capital: to grow Maryland’s first commercial-stage venture capital firm from the ground up.

“We’re not waiting for outside firms to build here,” she said. “We’re becoming the firm that this ecosystem needs.”

Stewart’s response, without hesitation: “Let’s do this thing.”

And the room felt that. Because the foundation is here. The pieces are in place. Now it is time to go.

Final Takeaway: The Best Attorneys Don’t Just Draft. They Deliver

As the session wrapped, Stewart offered a simple litmus test for founders choosing legal partners: “If your lawyer only talks when there’s a deadline, you’re missing out. They should be thinking ahead with you, using their network, showing up early, and staying late.”

“Find someone who’s truly in your corner. Who’s proactive. Who fights for you. Who brings their network to the table. Legal shouldn’t feel transactional. It is more than just memorializing something on paper. It should feel like someone is invested in your success.”

For Hemingway, the value of having a go-to attorney wasn’t abstract. “He’s shown up — through the failed companies, the wins, the weird pivots, the tight spots. That’s what makes a difference.”

This wasn’t a stuffy legal panel. It was a living, breathing look at the trust, grit, and collaboration it takes to survive and thrive in today’s venture landscape. Hemingway and Stewart weren’t just speakers. They were collaborators, challengers, and co-architects of something bigger: a better way to build in Baltimore.

As one founder in the audience put it: “This wasn’t just a talk. This was a call to action.”

And in an industry where founders often feel lost between law firms, term sheets, and equity splits, this chat was a rare glimpse at what it looks like when the legal side truly gets it. Even after being ghosted.

Author’s Note: For more fireside brilliance like this, follow Ecphora Capital and BioBuzz for updates on future sessions. And yes, Nick Stewart does take 5:30 a.m. calls. Just maybe let him finish his treadmill sprint first.