Gambling On Myself Made Me Serious About Becoming An Entrepreneur

Here's why gambling on myself was the best idea Shut Up & Hustle Founder Nick Dimengo ever had.
Image via Nick Dimengo

Gambling on myself was something that I always wanted to do, but, like a lot of people out there — especially those in the “millennial” category — it was easier said than done. Sure, working in Corporate America can really suck. Between all the bullshit office politics, awkward conversations to pass time with coworkers and demanding expectations of “showing face” for clients or bosses, I always loathed going into an office every single day. But want to know what’s not bullshit? Having a steady paycheck; and that’s just one of the reasons why gambling on myself was going to be so difficult to do.

That is, until I just decided to fucking do it.

Look, being an entrepreneur isn’t easy — which is an old cliche, but true on so many levels — so I’m not even going to try and say otherwise. Plus, I’m at the very itsy bitsy beginning of this wild journey that I’m embarking on, so who the hell knows how it’s all going to turn out for me? But one thing I already know is that, by gambling on myself and putting my own money on me, I’ve already done something most people wouldn’t dare do.

So Why Did Gambling On Myself Make Me More Serious About Starting A Company?

This is one of the simplest answers I’ve ever had. To be blunt: money.

Think about all the bad money habits we have. We spend money on things like streaming TV and music to help us waste time. We poison ourselves with booze on the weekends by dropping hundreds of dollars. We splurge on vacations and fancy things. We struggle to say “no” for fear of missing out… and there’s plenty more where all that come from.

What made me get serious as an entrepreneur was putting my money back into me, with the investment serving as a wake up call that it’s time to shut the fuck up and hustle. No more talk. No more “one day I’ll do this.” It was time to get to work.

It’s one thing to get money from an investor and have the pressure of repaying them for taking the risk and buying into you. It’s a whole different animal when you’re the one spending your own money to follow your dreams, knowing that, by doing so, you may not be able to work from a coffee shop by the final week of the month because spending just $5 to do so isn’t financially feasible. Yes, that’s the ugly truth about being an entrepreneur with an idea and passion — you’ll do it for fucking free; and it’s all kind of rewarding.

What Has Gambling On Myself Taught Me?

For one, it’s put things into perspective, making me rethink what is, and whom is, important in my life. It’s made me value the time I spend with people and hobbies that inspire and support me. It’s taught me to say no. It’s led me to practicing healthier daily habits.

But, let’s not sensationalize this thing as being ever-changing, because I have yet to make it. I have yet to make a single penny off of this idea I have and, for that reason, gambling on myself’s also brought on a ton of anxiety and stress and uncertainty. It’s made me challenge myself. It’s made me listen to suggestions. It’s made me learn. It’s made me lose lots of sleep. It’s made me get up early with excitement that, just maybe, that’ll be the day I get a call from someone telling me that they’re willing to partner up on something that will make Shut Up & Hustle a business and not just a hobby.

It’s also taught me to stay the course. There’s no taking the easy way out by applying to a full-time job for a steady paycheck. There’s no job out there that can give me the satisfaction I have every single minute of my day as this journey I’ve just started on, and there won’t be. Ever.

What Happens If Gambling On Myself Fails?

You know what? I fail… a lot… every single day. I learn from those failures as best I can, and am lucky enough to have smart, experienced and passionate people around me to keep me in my lane, reminding me that I don’t need to know everything right now. It’s a timeless lesson, really.

In terms of the big picture, though, I won’t fail. I can’t. I know what’s behind Door A, and I wasn’t satisfied. I don’t know what’s behind Door B; but, fuck, I sure am willing to knock on that thing as much as possible till it opens up for me and I get what I’m working towards.

Work. I mean, really, really work at it.

Gambling on myself was a difficult decision, because it’s not for everybody. It’s not something you just wake up one day and say you’re going to do. It’s something that, in my experience, has been the microcosm of my entire life, knowing that my stubbornness, passion and unwillingness to feel fulfilled by chasing someone else’s dreams will leave me satisfied.

Sure, I’m hustling on the side and working for someone else right now to make ends meet. I’m doing what I can to survive. Welcome to the life of an entrepreneur, where an extra couple bucks feels like a massive pay raise.

This journey of mine is only getting started. With blood, sweat, tears and lots of hustle, by gambling on myself, it’s proved to me that there’s no more time for talk, there’s only time for action.

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