When trying to entice a potential investor to put money into your startup over a business meal, it’s not always what you eat, but where you eat, that can make all the difference.

Gaby, a high-end French restaurant in Manhattan’s Sofitel New York, launched a lunch idea earlier this summer: 30 bucks for a 30-minute meal.

Could this be ideal for the savvy entrepreneur looking to butter up more than bread with a potential client or investor? Maybe not.

More than ever before, the wide array of lunchtime options makes picking a venue a bit of a crapshoot. Do you opt for a longish, pricey meal that evokes the Mad Men era? How about those 30-minute briskly moving sit-down affairs? Maybe “trucking it” is a better choice to demonstrate your hipness factor. And, hey, what about just ordering in?

“Picking the best lunch option is about intent, location, and perception,” says David Leite, the publisher of Leite’s Culinaria, an online food publication, and the author of The New Portuguese Table. Leite, who has 18 years’ experience in the advertising business, says one of the biggest challenges facing an entrepreneur trying to advance a lunch deal is time.

“The world has really sped up,” says Leite. “If you’re presenting to me, I need to know what you have to offer me right up front, so we’re not going to waste each other’s time. You’re going to have to dazzle me. Ultimately it’s about seduction. Where you do the seducing communicates something about you, so it has to be carefully thought out. No matter where you take the person, there has to be an alignment between the venue, what you’re trying to sell, and how your message will be received.”

So, keeping in mind that the grub—and where you eat it—communicates something about you and your business acumen, here are some tips to chew on.

Fine Dining

Upside: Taking a potential partner to an upscale restaurant signals “immediate impressiveness,” says Leite. “It says the presenter has gone out of his way.” For Leite, this experience works better after you’ve had a successful first meeting. “In a fine-dining establishment, as someone being presented to, I know I can have a conversation with the person and, after two hours, can walk away more knowledgeable about what he can offer me.”

Downside: Make sure the venture capitalist you’re courting won’t brand you as a spendthrift. “Research your target,” he says, noting that if the venture capitalist is known for being thrifty, then don’t waste your time, money, and a potential deal on a luxe lunch.”

30-Minute Lunch

Upside: Sounds promising, right? What’s not to like about a good-looking venue with expertise in making good on their well-clocked offerings? Thirty minutes might be fine if time is limited. But be careful. That allure may be superficial.

Downside: “I need more than 30 minutes to feel out someone’s ideas,” says Leite, noting that interruptions by wait staff may cut down eating time by as much as half, and noise may be problematic as you’re trying to make your presentation. “To me, it’s like speed dating,” he says.

Booze-Enhanced Lunch

Upside: No problem, generally speaking, says Leite. When the entrepreneur is involved with high-end products or services, a bottle of wine or champagne often plays into what’s being sold and sets a good tone. And, he suggests, if owners of a young startup are involved with technology—for example, music-related products or smartphone apps—then an evening rendezvous at a bar filled with the very people who will buy the product might also be appropriate.

Downside: Loose lips sink ships and deals. A potential investor will be watching how much the entrepreneur and entourage drink, says Leite, noting that if the fund seekers drink inappropriately when in need of cash, imagine what happens when the startup is flush with funds.

Food Trucks

Upside: “Lunching at a food truck is great if the food truck location is in sync with your proposition, such as pointing to the well-trafficked area as a potential site for, say, another food truck or a business related to outdoor dining,” says Leite. Because a food-truck scenario typically moves at a brisk pace, he considers it a good first date that allows the entrepreneur to present ideas briefly. It’s also fine when the people who meet share enough quick outdoor-eating experience that eating at food trucks is not distracting. It may be best for hearty souls who can walk and eat at the same time.

Downside: Eating standing up and constantly shifting your body to not drip food on your clothes can be distracting, he says, noting that, although you might think you’re doing out-of-towners a favor by giving them an “experience,” you may be shooting yourself in the foot. “The food truck itself may wind up eclipsing the point of your meeting.”


Upside: It’s logical that entrepreneurs consider their lairs to be perfect backdrops for lunch with a potential investor. After all, they reason, a funder will note the young company’s energetic crew, the burgeoning culture, and even experience the nostalgia of seeing futons that evoke 22-hour workdays. And how about all that free time to chat while waiting for the food delivery?

Downside: Leite would not be impressed. “It would turn me right off, unless I’d been at the office before,” he says, suggesting any investor’s appreciation of entrepreneurial forethought that would eliminate the need for paper plates, containers, and plastic cutlery. If the entrepreneur wants to capitalize on the informality associated with eating at a conference table, Leite suggests the entrepreneur invite the investor for a meeting at the office sans food. Or, he says, present the best cookies and lemonade—or any well-put-together treats—in your arsenal. It doesn’t have to be lunch. “An investor pays attention to everything: how the entrepreneur dresses, speaks, and even the lighting and furniture in the space,” he says. So the food had better taste and look good, and you have lots more control when you’re not pulling it out of a shopping bag.

Leite concedes that strategizing the best lunch option might take a little homework. He suggests scouring the Internet for stories about the person you’re wooing. The rest is common sense.

“If I’m a venture capitalist in my 50s and thinking about investing in your company, and you’re taking me out to lunch, we’d better not be going to Coney Island, unless you’ve got a Coney Island-style business,” he says.


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