Bursting into tears in front of one of our lead investors was not my proudest moment. The investor, Nancy, and her husband Dan were good friends of mine. I was sitting across from them at their dinner table and had just revealed my brilliant plan to raise more money for the startup in which Nancy was heavily invested. Instead of just going about the same routine, contacting people I knew to see if they would invest, I had decided to visualize or “manifest” a firm goal, a technique I had been hearing a lot about. I was going to raise another $200,000 in two-and-a-half months, and by visualizing a set amount and a firm date, by God, I was going to make it happen.

Dan, who happens to be a brilliant financial advisor, nodded. “That’s great,” he said. “How are you going to do it?”

“I’m going to get in touch with everyone who has passed so far, tell them about all of our progress, and make my pitch again.”

“Uh huh,” he said.

“What?”

“Why aren’t you contacting people who’ve already invested?”

“Uhm, because they already invested.”

“Right. So you should go back to them and tell them to invest more.”

That sounded like a horrible idea to me. “I can’t do that!”

“Why?”

I was really uncomfortable. “Because I already asked them for money, and they gave it to me.” (I still had the mindset that these people had done me a huge favor.)

“Right,” said Dan, “they did. You offered them an opportunity, and they took it. And with the money they gave you, you turned an idea into an actual product that is winning awards, getting industry praise, and is now on shelves in brick-and-mortar stores. So go back to them and tell them you want them to double their investment.”

Double? I was flabbergasted. “I can’t do that,” I said.

“Why not?”

I looked over at Nancy. She had a bemused look on her face . . . half-smile, eyebrows raised.

“They already gave me money. I can’t just ask them for more.”

“They didn’t give you money. They invested money. And you’re not going to ask them for more money. You’re going to tell them you want them to double their investment.”

“That sounds like a horrible idea.”

“Why? You’re doing what you said you’d do. Tell them that. Call each of your investors and say, ‘You believed in Batch 22 when it was just an idea. It’s not an idea anymore. We’re in production, we’re winning awards, we're making sales, and I want you to double your current investment so we can continue to grow.’”

“I’m not going to do that. It feels like . . . .”

“What? It feels like what?”

I didn’t even know how to put it into words. Asking this would be the most massive presumption and overstepping and rudeness I could imagine. I looked to Nancy for help. Surely she would understand, but she was still just sitting there with that look on her face. “I really think it would alienate them,” I said.

Dan raised his voice. “I’m telling you, if you want to hit your goal, call each of your investors. I’ll say it again. Don’t ask them for more money. Tell them: ‘You believed in Batch 22 when it was just an idea. It’s not an idea anymore. We’re in production, we’re winning awards, we're making sales, and I want you to double your current investment so we can continue to grow.’”

Nancy was still looking at me like I was an idiot. Her subtext was clear: I’m right here. I turned to her.

“Nancy?”

“Yes?”

I was trembling, but I kept going and made myself say the words. “You believed in Batch 22 when it was just an idea. It’s not an idea anymore. We’re in production, we’re winning awards, we're making sales, and I want you to double your current investment so we can continue to grow.”

She smiled. “Okay,” she said. And with that, she got up, walked into the other room, wrote out a check, and handed it to me. I took it from her, and then I burst into tears.

“You guys played me,” I said.

They both came around the table and hugged me. “Yeah,” Dan said, “we did. This is hard stuff to learn, and we had to teach you a lesson.”

The next day, heart pounding and still filled with doubt, I called each investor and said exactly what I’d said to Nancy. A few of them said they were in as deep as they were prepared to go. A few more said to ask again in a few months. Three agreed to double their participation. I had met my goal. It took less than an hour, and every one of them that I spoke with responded as if my request was the most reasonable thing in the world.

I’ve spent a lot of time since that evening trying to figure out why it was so difficult for me to step up to the plate in the way that Dan was suggesting. I’m not shy, by any stretch of the imagination. I’ve done thousands of performances on stage, including on Broadway in front of thousands of people. I’ve argued an appeal in front of a bench of seven judges in the highest court in New York State. On all of those occasions, I have had a surfeit of confidence. What was it about the simple act of asking for money that could tie me up in knots and lead me to such painful self-doubt?

What I have come to is this: When I ask a potential investor for money, I’m asking them to believe in me. It feels personal in a way that acting and lawyering does not. When I’m on stage, I’m a vehicle for the words and the message being conveyed by the rest of the creative team. I’m asking the audience to surrender to an illusion that will convey a story and the playwright’s message. When I was in court, I was fighting for someone else, trying to sway the judges to my client’s cause and my interpretation of the law. But when I ask someone for money for my company, I’m asking them to believe in me.

As the owner of a start up, you have to be ready for that. You’re going to be asking people to believe in your idea, your product, and your ability to execute. You’re going to ask them to believe in you, and that will put you on the line in a way that you may have never been before. If you’re a newcomer to the role of entrepreneur, as I was, this is terrifying.

So how have I learned to overcome fear? I focus on four things:

First, Batch 22 is a truly exceptional product. Of course, at the beginning of our venture, this was a subjective assessment. Now it’s an objective one. We have won too many awards, received too many industry accolades in print, and converted too many customers for it to be anything else.

Second, I do know what I’m talking about. Although the learning curve has been steep, my partner and I have mastered what we needed to know each step along the way.

Third, to a large degree, we have already succeeded. Aside from all of the awards, accolades, and sales, 95% of start-ups in the spirits industry flame out by year two. Of those that survive that milestone, 50% drop out shortly thereafter. We’re in year seven, and growth is accelerating.

Finally, because of all of those points, I know that when I am asking someone to invest, I am not asking for a favor. I am offering an opportunity, the chance to be part of something that will reshape the landscape of the back bar across the country and the world. I am clear and honest about our product, our capabilities, and the risks. And I am clear about the opportunity for extraordinary returns when we succeed.

If you’re just beginning on your road as an entrepreneur, I hope these points will help you along your journey. And I’d ask you to always keep the last point front of mind. Nobody has to invest. But those who do will want to invest in someone with confidence and a clear vision.