How Watching Jerry Maguire Can Help You Raise Money

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Five minutes before my first-ever pitch to an investor, I practiced Jerry Maguire in the mirror.

By Nayia Moysidis (Founder, Writer’s Bloq)

“Show me the money,” I told myself six or seven times, and then just once, just as a final pump-up tactic, one epic shout: “SHOW ME THE MONEY!” When I emerged from the Starbucks bathroom, a young woman peeked inside, visibly nervous and probably searching for the body of a murdered drug lord within.

Interestingly enough, I’ve done this before. Not the show me the money bit necessarily, but I’m no stranger to talking to my reflection. Quite a few of my loved ones have caught me serenading myself with highly complimentary statements that serve to over-inflate my ego. But this time, the pep talk had a real purpose. For the next two hours, I’d need to be absolutely unshakeable. I’d need to be unrealistically optimistic about tremendous obstacles I had yet to fathom.

This prospective investor was a professional schmoozer, and he thought he’d warm me up first. He told his business partner, also present at our meeting, that I’d make the ideal CEO, that I was bright but stern, that I clearly had experienced enough adversity in my past to face the struggles of entrepreneurship. The empty compliments reflected off my surface, but like the mirror had taught me, I smiled back at him, showing him only what he wanted to see. Long ago, I made it my policy to ignore both criticism and praise that rode on the shoulders of motive. This policy has served me well.

Towards the end of the hour-long coffee, he made his move. He put a check on the table. I didn’t look down at it. I knew the zeros would hypnotize me. All I had at that moment was a concept, a painful desire to solve a problem I had personally suffered, and 4,000 of my own dollars in the bank. I had just finished college a few weeks prior, and the ink on my bachelor’s degree in creative writing was probably still wet. This man had nearly 50 years more experience than I, five decades more practice sizing people up, dozens of perfected negotiation tactics than I didn’t even know existed, and he knew. He knew he had the advantage, but I knew something he didn’t, one thing that made all the difference. He thought I was living in the present, a college kid desperate for someone to pat me on the back, but I’d already made a home in the future. I already knew, without a shadow of a doubt, who I could be and what I could do a few years down the road.

So when he suggested that he would own 10% of my company for that check amount, a sum that at that time he expected would impress a recent graduate, I refused. And he wouldn’t negotiate, certain that I would give in by month’s end. I thanked him for his time and departed.

Three weeks later, I had a check in my hand that was quadruple the size. The investors cared about the publishing industry, and the deal was fair. It valued both the people who were taking a gamble on a young entrepreneur, and myself, the one who was about to be sleepless and stressed and overworked for the next two years.

Only then did I allow myself a Rod Tidwell victory dance. And then I deposited that check and looked further into the future.

Women 2.0: How do you psyche yourself up before an important meeting?

Photo credit: ElHormiguero via Flickr

About the guest blogger: Nayia Moysidis is the Founder of Writer’s Bloq, a literary collective that helps great writers get discovered. Nayia graduated from Columbia’s Creative Writing program in May 2011. During her years at Columbia, she played Division I soccer, explored six continents, and held positions at Film London, VISA, SportsMark, and Simon & Schuster. She has been published in Women 2.0, The Levo League, The Daily Muse, The Huffington Post and Forbes. Follow her on Twitter at @NAYIAisms.