Think back to when you were 25 years old. Now place yourself into the most recognizable office in America, sitting across from the most recognizable businessman in America.  

That's where my husband and I found ourselves in 2004, when we secured the most important meeting of our young careers: 15 minutes at Trump Tower, during which we were to request a $1 million cash investment from the man whose name was plastered onto the building.  

Calling it surreal is an epic understatement. Remember: This is fresh off the first season of The Apprentice. Not only were we meeting with the biggest business celebrity in the world on his turf, but his turf was the set of the No.1 show on television. 

It was hard not to feel like there were cameras rolling - especially since the office looked exactly how it did on NBC: with the gorgeous Central Park views, stacks of papers sprawled all over, and walls plastered with dozens - maybe hundreds - of portraits and magazine covers featuring the man we were about to meet. 

What made things doubly challenging: Our company didn't have a whole lot to offer. 

Less than three years after we founded Arkadium, we had no major deals under our belt, let alone any high-stakes meetings like this. So the conversation starter wasn't "Nice to meet you Mr. Trump, we're the creators of games that deliver 1 billion hours of entertainment every year!" That wouldn't be the case for a few more years. This was, effectively, "Hi, Mr. Trump. All we have to sell you is a lot of potential." 

We were nervous, and very obviously punching above our weight class, but we knew this was the single biggest moment for our company to date. So we had a plan.  

Unsurprisingly, he very quickly got down to business. 

"How can I help you?" He seemed genuinely interested as long as we wouldn't take up much of his time. 

It was time to unleash our big ask. We outlined what a seven-figure investment would do for our company, and how it would benefit him. Luckily, we were prepared to hear the word no. Because that was his response. 

"What else can I do for you?" We had our No. 2 ask lined up. We asked him to join Arkadium's board. 

Nope. Next. 

Our third ask was dialed back a few notches, but we felt confident. Knowing that he controlled several casinos, we asked if he could put Arkadium's online casino games onto his casinos' websites.  

"Rhona!" He called over to his longtime assistant, Rhona Graff, and instructed her to get us in touch with the people in charge of the company's websites. Less than a week later, Arkadium games were on every site in the network.  

Nearly 20 years later, our company has evolved several times over, and Kenny and I have been in hundreds of high-stakes meeting situations. (Trump has done some... evolving since then, too.) But looking back, there are three clear takeaways for young entrepreneurs looking to grow their businesses. 

Always have a second - and third, and fourth - ask ready

The best of the best expect this level of preparation in meetings like this one. We came prepared with a physical list of asks, knowing that the ones toward the top were less than likely. 

Even if we were confident that Donald Trump was prepared to open his checkbook for a pair of 25-year-olds and their new gaming company, Options B, C, D and E would've still been necessary. If you get caught unprepared in a meeting of that magnitude, you most likely won't get another. 

You can't always control the timing of the meetings you get. 

I talk a lot about the differences between "good" nervous and "bad" nervous. This was the good kind - I was anxious to be in a situation I'd never been in before and wanted to represent myself and my company well on a big stage. 

Harnessing that anxiousness requires mastering your nerves and emotions. We were confident in our company, and even though we'd never faced that kind of situation, we knew that this was our moment to make something happen. Which leads into my final point: 

Winners don't let big opportunities pass them by. 

The most crucial moments are rarely comfortable - the key is pushing past your comfort zone and stepping up, even when you don't feel ready. If you're confident in your business and in yourself, you'll find a way. But if you shy away from moments like this one, you'll never be in a position to take major steps toward reaching greatness.  

Published on: Aug 15, 2019
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