My Tussle with The Hustle — The Millennial Entrepreneur

My Tussle with The Hustle: How to Evolve as an Entrepreneur

Entrepreneurs. Those crazy cats. Whether it’s in their DNA or based on privilege and family money, we can’t help but admire the “chosen ones” willing to risk it all and not afraid to fail (and sometimes fail spectacularly). Those who’ve forsaken salaries because a fixed income is depressing (read: there’s a ceiling) and who’ve realized the “stability” of a job is an illusion. They don’t want to build someone else’s equity. We picture young guns working 80 hours a week, living off of a dream and a bottle (or two) of Mountain Dew a day. “I just clocked 18 hours straight!” and “I’m burning the midnight oil” are all part of the entrepreneurial lexicon. After all, you’re not “ramping up” your company if you don’t hear the incessant tap tap tapping of the keyboard or the chitter chatter of sales calls.

Let’s face it: we glorify “the hustle.” The men and women who have dreams and execute them. Isn’t it ironic that the word “execute” also means “to put to death?” Seriously, is working long hours and suffering simply a prerequisite for success? It sure seems like it. Practically every business book espouses the importance of “failing to succeed” and the need to “put it all on the table.” You want success? It’s simple: focus on your business more than your loved ones, until you hit some random level at which you’ll be satisfied. Work harder than anyone else. “Only for a time” they say… “it’s just a phase, your loved ones will understand losing you for a time when you win it all… it’s the decision you have to make if you want to win.”

It’s like the struggle has become a part of an entrepreneur’s supposed reality. If you’re not grinding it out, you’re not really an entrepreneur. If you’re not sleep deprived, well, you must be lazy and weak-hearted. True entrepreneurs put their companies first! They work dusk ’til dawn and then some. They forsake everything else and worry about every minute of every day and ensuring it’s used to grow their business. Whatever it takes, no holds barred. Cue Shia LaBeouf’s “Do It” speech, spit and all. Entrepreneurship has never been more attainable and the only thing stopping us is our own ability to work harder. Right?

Perhaps. But what if it’s all a lie? What if failing isn’t necessary to succeed? What if going out on your own is less of a risk than “death by cubicle?” and what if starting a company AFTER you’ve settled down and had kids is actually the best time to hang your shingle? And who said X amount of hours worked per day equals X amount of gold stars? I mean really, there are no rules, only norms and expectations. What if I told you that you could build a better, more sustainable company working less and that being an entrepreneur is not just a way to get rich, it’s a way to take ownership of your work-life balance? Would you believe me? Or just assume I’m one of the lucky ones?

I wasn’t lucky. I worked my ass off. I sacrificed my health, relationships, you name it. I started my first company at 14. I have to admit, I didn’t have much to worry about… my parents were still covering my needs and I didn’t have to worry about any mouths to feed, not even my own. There were a lot of benefits: I could spend as much time on my company as I wanted and I had nothing holding me back (except for the surprised stares at board meetings and pitches when they realized my age). It was a launchpad sent from heaven. And I did just that. I launched my company and grew it to seven figures over the following years. I ended up living in Beverly Hills, driving a Beamer and rocking a $10,000 watch around the time I could legally drink. Ahh, my hard work had paid off. The decimal point had moved and I was living proof that working harder leads to achieving “the life.” My complete lack of work-life balance had finally paid off. I had it all.

Except I didn’t. Sure, I had material possessions and the respect of others working and striving for the same pay-off. I was featured in the Los Angeles Business Journal’s Twenty in their Twenties. I traveled first-class and had ample adventures globetrotting. I had enough where pretty much nothing worried me (at least financially). I was drinking my own Kool-Aid for a while and I was intoxicated with myself. Why was it so hard for others to succeed? They just needed to work as hard as I did! They’re just lazy, I would think. Lazy and lost. Little did I know, I was the one that was lost. And empty. I wasn’t there for people. I lost my first wife. I was unavailable when my own mom was paralyzed from the waist down (she since recovered, thank God). I started to become numb to other’s and I even tattooed my company’s logo to my skin, a sign of my undying commitment and a sign that my identity was being defined by my company and not the other way around.

One crisp autumn day in LA, at the age of 22, I realized I had everything yet nothing. It’s kinda like feeling lonely in New York City. You’re surrounded by people, but you’re completely alone. I was surrounded by my success, but miserable. And alone, except for people who loved my money. Eventually, it was too much. I couldn’t go on. I left LA and “came home.” Then it started to get bad. Really bad. My former business partner literally disappeared along with a trail of collateral damage left along the way. After a decade, my business was gone. Part of me died with it. I’d let myself become my business and my business become myself.

The story didn’t end there, fortunately. I made ends meet and became a key player at several ad agencies. I spent some time overseas and got rid of practically all of my possessions. I was humbled, more than once. I apologized to my loved ones. Slowly but surely, my identity became less wrapped up in my company and work and more wrapped up in my relationships and people. I knew what it was like to have money and therefore I became less concerned with chasing it and more comfortable with being less comfortable. I consciously chose to slow down. I realized I had been moving so fast and burning so hard that my body and soul were crumbling and the years felt like a blur… a previous life to an extent.

Something strange happened after resetting my paradigm. I evolved into a better entrepreneur. A few years ago I left the comforts of a cushy agency gig with my second child on the way and nothing in savings. It was time. Bull & Beard was conceived and needed to be launched. I had found a great partner (or, more accurately, we found each other) and had the confidence that we could succeed and it was a bigger risk to not try again. But I wasn’t going to go back to my old ways. This time around I had a great marriage and two beautiful daughters. I wasn’t losing my family to my business again. I no longer believed it takes more to get more. I saw in my previous company how oftentimes the less I worried and worked, the more success I achieved. I expected it and it happened. So why couldn’t I feel and project the same confidence this time around? Why couldn’t I take the lessons learned at the top?

It has been a great ride so far. There have been bumps in the road, sure. It hasn’t been easy. Yet, in three years my business partner and I have built what it took two or three times that amount of time to build when I was younger and worked non-stop. As you grow, you realize 80% of your time is usually spent on “busy work” that makes YOU feel good, but it’s not really moving the dial. Entrepreneurship is a good thing. Too much of a good thing is a bad thing. I can honestly say that I now rarely work more than 40 hours per week (most of the time it’s more like 30–35). I’m more productive than I’ve ever been as those hours are high-energy, focused time spent on what matters the most. I let the small things go, because the small things are just distractions that eat your time. I don’t have any guilt about not being there for my family now. In fact, I’ve probably spent more time with my family in the past couple of years than I did during the life of my previous company. I got lucky in that my business partner was and is on the same page. We both think we can succeed and have balance. We both know working for the sake of working is not the path we want to take. It may make you feel better (read: more in control) thinking you’re doing everything possible to succeed by working all of the time, but it’s an illusion. There are no rules and certainly no lucky number of hours needed to succeed.

Maturing as an entrepreneur oftentimes means evolving to the point where you finally realize “hard work” has nothing to do with hours. It has everything to do with decisions. Choose today to think about the decisions you're making. Whether it’s your company, your job, your family, your time — — don’t just do what you think you’re supposed to do. Don’t just live by inertia. Don’t wake up one day surrounded by things and lacking in memories. Enjoy the journey and embrace this time. You may come to realize moving a little bit slower just might be the key to building not only a better company, but a better life. Maybe it will take a little longer this way, maybe not. When you’re on your deathbed, you won’t be analyzing the hours you should have worked… you’ll be questioning why you didn’t spend more time with your children or your spouse or your parents when you could. And you won’t have any idea what it was that was so much more important, because it wasn’t. You just bought into the hype of the hustle.