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Once upon a time, there was a young and scrappy entrepreneur who sent an email to a famous billionaire he didn’t know and ended up getting a $1 million investment.
This isn’t a fairy tale; it’s what happened when I sat at my desk one evening and decided to take a shot and email Mark Cuban. I’ve always admired his ideas and his approach to business, and I thought he’d appreciate my startup, SAVRpak, which helps keep takeout, packaged foods and produce fresher for longer. So I found his address, dropped him a note, and forgot all about it, thinking there was little-to-no chance the man who stars on ABC’s Shark Tank and owns the Dallas Mavericks would rush to answer my email.
A few hours later, while cooking dinner for some friends, I pulled out my phone to check something and, by force of habit, took a quick look at my inbox. And there it was. A reply from Mark Cuban. It was just a few words long, but I didn’t care; it was an invitation to an engagement, an engagement that, in my case, ended with Cuban becoming my investor.
I’ll be honest: If this wasn’t my story, and if I had heard the very tale I’m telling you now, I might’ve dismissed it as a one-off, some crazy fantasy that never really happens in the real world to guys like me. But having lived through this thrilling and deeply instructive experience, allow me to offer five pieces of advice on how you, too, can take the sort of initiative that might end with a very famous investor and a very large check in the bank.
Take the chance!
It might sound obvious, but it’s not. Anyone looking over my shoulder as I drafted that initial note to Cuban might have very well advised me not to waste my time. Such a critic might’ve noted that cold-emailing celebrity billionaires is hardly the most prudent and logical approach, and such a critic would’ve been right. But business, like life, isn’t always rational, and sometimes just jumping right in and making an ask defies logic and rewards the bold. So, as the old and wise slogan goes, just do it.
Treat it like a sport
How to do it, however, is an entirely different question, one that I can answer with great joy: Treat it like a sport. There’s a reason why so many business people are fond of using athletic metaphor, like saying a deal is a home run or that the negotiations are on the five-yard line. It’s because capitalism, like sport, is, at its best, a respectful and rule-bound, yet playful and muscular competition. My conversation with Cuban is a case in point: One or two emails into our conversations, the famously outspoken investor tried to rattle my confidence by dismissing the potential worth of my business. I remained polite, of course — you’d be foolish not to when talking to a man who knows a thing or two about business — but shot back with my own reply, which not only delivered facts and figures I thought Cuban should know but also showed him that I can play the game.
Have a conversation
This leads me to my third point: When engaging a high-profile potential investor, you’re not really pitching; you’re having a conversation. Once Cuban was convinced that I was someone who knew his business and had the wherewithal to stand his ground and champion his own cause, he asked excellent and insightful questions and made great suggestions that I happily followed. I didn’t just try to sell him on my company; I listened, and this engagement is what took our exchange from a random back-and-forth online to a real and fruitful business relationship.
Of course, in business, like in, say, dating, you can hardly get very far unless you have a pretty good idea of what the other side likes. Before writing Cuban that first note, I spent a good bit of time reading up on him and getting a good sense of how he approached deal-making. I learned how he liked to communicate and what he considered to be an utter waste of time, which helped me hit the right notes early and make our interaction a meaningful one.
Again, like dating, make sure everyone is having fun. For example, when Cuban wrote and tweaked me by suggesting that my company wasn’t worth as much as I believed, I didn’t respond with an indignant missive or a spreadsheet dense with numbers. I just sent him a sad face emoji before writing back a short and polite response stating my opinion. That silly little gesture isn’t the sort of tactic they teach you at business school, but it told Cuban a lot about me and how I approach life, showing him that I’m serious about business but also a down-to-earth guy who isn’t above a bit of banter when the occasion calls for it. This is exactly the sort of realness that moves a relationship forward fast, even — or especially — when the person you’re trying to court is one of the world’s busiest and most sought-after investors.
Follow these lessons, and you might not land a business partner of Cuban’s caliber, but I guarantee you’ll do much, much better than you would have otherwise. Trust me: If you take chances and have fun, do your work and stand your ground, engage and educate and enchant, you, too, will have your happily ever after.