What I learn from my (by far) more social colleagues

From the Archives

Originally published October 30, 2015

A few weeks ago, I caught up with some former colleagues for dinner, drinks, and camaraderie. One of them left a steady paycheck to pursue a startup idea that had been swirling around in his head for a while. Today, his vision is coming to fruition after a year and a half of unrelenting focus and hard work. What he shared later that night when we met up with a group of five other former colleagues is inspirational. It’s not necessarily what he shared, but that he shared and that he did so with great candor. Meet the illustrious – the Real – Josh Nespo.

You should know up front that this chap is a partier. I mean, he knows how to party, and as little partying as he has been doing in recent months, he does it right when he gets around to it. (I’ve heard the stories, and I’ve seen a few videos.) So when he takes a break from building his empire, I’m interested not only in how much fun I’ll have, but also in how much I still have to learn from him. Here’s what impressed me his last time in Philly.

1) Work hard. From meeting with influential people to building a client base to scoping out buildings that will house his brick-and-mortar operations, it’s important to put in the hours and to pay attention to the details. That has to happen even on days you don’t feel like getting out of bed.

2) Stay in bed. Every now and then, it’s also OK to take a mental, spiritual, and physical break from the daily grind. It’s healthy, and the most successful entrepreneurs have figured that out. Do that. And then get right back on your feet before bad habits kick in.

3) Be honest. Start by being truthful with yourself, and you will only ever act with integrity and authenticity toward others. If you start a project or business and are scared of what’s going to happen next, let yourself experience that feeling. If you need help or encouragement, don’t pretend you can make do without it. Ask for hep. Seek counsel. Knock on doors. Tell the truth in words and actions.

4) Relax, have fun. When it’s time to strike a balance between business and social interactions, know when you need time to hang out with family, friends, or both and just bug out. Whatever fun means for you, go do that thing to clear your head for a night or two. Take the weekend off. Stay at a hotel or a friend’s house. Get out of the environment that reminds you of work.

5) Take care. Some years ago, I got word that with compounded medical issues, I wouldn’t likely live beyond the two or three years stretched in front of me. I took that to mean that I should get my affairs in order, secure a future for my loved ones, and then live as if every day was my last. Well, that is until I rejected the idea that I wouldn’t live to be 120. Through conversations with this fellow when we still worked together, I developed a very different outlook. I treated every day as a new beginning and not as some symptom of the very end.

On his most recent storm though Philly, he reminded me of our deeply philosophical talks about my health and my increasingly callous attitude toward it. So inspired am I by his thirst for life and fulfillment, that I haven’t given much thought about that part of my history. When he brought it up the other week, it occurred to me that it has been about four years since I was told – by two different professionals – that I had about two years to live. I still live on the edge in some regards, though I take care to mind that my health is largely how I feel about it. I’m grateful to him for reminding me of that.

6) Pay it forward. Some day we’re all going to be working for this guy. I can only hope I’ve done enough good in this life to sit at this captain’s table when it happens. In the meantime, I’ll settle for taking advantage of every opportunity I can to share with others his bits of wisdom, zest for life, enthusiasm for giving back, and vision for building community.

What are some of your tips for striking a balance between business and pleasure? Please share in comments below. Thank you for reading.