Daniel DiGriz of MadPipe: Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life

Pirie Jones Grossman
Authority Magazine
Published in
57 min readMay 28, 2021


You will not get it right the first time. That probably seems obvious. It’s obvious to me after starting several businesses, but I didn’t really understand it the first time. I thought I would plan it, get it right, launch, and it would either work or not work. That’s true of an omelet, but not a business. That should be comforting. It’s not a binary proposition: win/lose. It’s not an all or nothing proposition.

Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50's.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Daniel DiGriz.

Daniel DiGriz operates MadPipe, a marketing agency that implements marketing, provides clients with a marketing director or CMO, and takes on marketing projects like a campaign or website. His passion is working with organizations in any industry that have a vision for making the world better and a powerful untold story to tell.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I grew up in the central swath of the US that forms the Great Plains, nourished by the Mississippi River and its various tributaries. Nonetheless, I never developed a sense of home and place. I moved between seven states and more than a dozen towns and schools. I identify with Jean Reno’s character Leon in the film “Leon: The Professional”. Like him, one might say I had no roots. What I did have was a lot of experiences that were atypical of the idyllic childhood. Everyone asks if my family was military, and I answer in the affirmative as an easy and partially correct answer but, like a lot of things, it’s more complicated than a brief introduction allows. Perhaps fittingly, I was part of one of the ‘lost generations’, namely “Generation Jones” (1964–1969), that exist on the cusp between Gen-X and the Xennials. Scholars don’t agree on the exact period, just that something was stuck, like a clog in the system, for a few years, and some of us were caught in the middle of seismic if arguably invisible forces.

It was certainly an interesting time. Conflict and hope were bedside companions. The Cold War was in full swing, with us hiding under our school desks in required drills from Leonid Brezhnev — with his nukes and enormous eyebrows. I was watching Watergate unfold on TV, in between Sesame Street and Mister Rogers. I was born in time for Haight-Ashbury (my older brother had an afro and love beads). People wore bell bottoms, earth shoes, and graffiti-art t-shirts with slogans like “I’m with Stupid” or “Dyno-mite!”. I saw and joined the proliferation of heavy metal, punk, and new wave. This is back when Progressive music was in full swing and people listened to whole albums as works of art, because it was LPs and cassettes; the CD and the Walkman hadn’t been invented to shorten our attention spans just in time for cell phones. And finally, I checked out of childhood, leaving home at 17, right after Prince and before Madonna. I happily missed grunge and alternative but had to endure disco and Urban Cowboy. I saw Star Wars in the theater and was in awe at the birth of the PC.

The most common thing I tell people is I grew up rough. That conjures various images in people’s heads. Were your parents criminals? Did you see violence? Did you do desperate things? The answer to some of that depends on the moment. Home life was violent. School was violent. And Hell, there was violence in the streets. I think a lot of people forget. It was a rough time. I prefer to focus on what I am now, but I’ll say I took enough blows to the head to be Rocky and eventually had to break free and create my own vision of being a champion.

What I don’t do is forget. Observing human behavior in a chaotic period became a source of insight. To dig a little deeper at the cultural memory, young men were coming back from Viet Nam who weren’t whole. Substance abuse was typical, whether people fought in the war or against it. Labor unrest was sweeping the country. I saw picket lines, saw people pick up bats and crowbars, and there were nights when I wasn’t sure people I cared about were coming back intact. Heads got broken. Teeth got kicked in. Things got vandalized. I saw death and despair, depression and familial harm. I saw self-harm. I saw fear and the disdain it breeds for humanity and the contempt for anyone different.

I was also born just after school desegregation and lived in places where people still didn’t accept it. You might remember that, in the mid-70s, anti-integration violence was still happening as far North as Boston. That was just the stuff people heard about from Walter Cronkite and Dan Rather. Schools aside, housing segregation was still the norm, so a lot of civil rights gains were arguably superficial. I encountered some pretty egregious violence perpetrated by people I thought I knew and people I never understood, all because someone was a different tint. I saw mass violence in Shreveport and was treated pretty badly for taking the minority side. I saw shootings in Arkansas. I stood against the Klan in South Carolina, when they had everybody scared. It was not pretty. As a kid, I did what I could, which is surprisingly much and surprisingly little.

I can talk easily about these events, because I’m not a collection of things that happened to me or images I saw. I’m not the sum of where I’ve been, but a force composed of where I’m going. I’d be lying if I said I didn’t value what I learned by paying close attention. I studied people. I watched carefully to understand what they were capable of, how they operated, what they might do under various circumstances. I “got over” as Stephen King likes to say in his great book of that era — Hearts in Atlantis. I endured and overcame, and I’m grateful I saw people endure and overcome far more. A lot of people I knew didn’t. Some aren’t with us anymore. They’re names on a rough-hewn stone in on quiet, grassy hills that traffic passes by without knowing who they were.

The most important insights I gathered and brought forward as a kid are that anyone can be wrong, might doesn’t make right, and it’s possible to hide, nurture, and protect enough of oneself, to free it, like a bird from a cage, at some later date. There’s a song by Sia — “Bird Set Free”. It’s one of my anthems. I really dig people that overcome. Blessed is the one who overcomes, says the Scripture. Their names are not always remembered now, but without them, I wonder how many of us would be here.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

It’s a line from the film The 13th Warrior — two words: “Grow stronger.” This little guy at sea is traveling with a band of enormous Vikings. They give him a Viking sword. He can’t even raise the tip of the blade. It’s so heavy. He says, “I can’t lift this.” The Viking who gave it to him says, matter-of-factly, “Grow stronger.”

We’re in a polarized culture where victim-status is fast being adopted by even the most privileged, including those who have oppressed others for generations. We face this great cognitive obstacle, where every preference is part of identity — if you don’t like what I like, then you’re attacking me and rejecting my culture and myself. And on the other hand, important matters on which good people could once disagree in a passionate yet good-natured way are becoming total — all or nothing propositions to which only dogmatic agreement exempts you from perceived enemy status.

If you don’t share my version of justice and view of how society should be ordered, you might be cancelled and destroyed, threatened or denounced, for the infraction of even raising the question. This is not strength. It’s not resilience. I know from hard experience, none of those attitudes can withstand the test of a strong wind, let alone the storms I weathered as a youth. We have significant challenges before us, and they will become more significant as we ignore them and bicker.

We must grow stronger. But we can only choose for ourselves. I’ve not had many shoulders to cry on, much forgiveness to bank on, or much recourse if my choices don’t pan out. There was no net, no one to catch me, and the stakes were high. Whenever I face an obstacle and feel as though I don’t have the strength, I remember that others have faced similar things and endured. I hear my inner Viking telling me to “Grow stronger.” We must all do this. We must be Vikings.

I looked up my DNA, by the way, and it turns out sure enough, I’ve actually got Viking coursing through my veins. My people swept down from Iceland, invaded England and Ireland, and sure gave a lot of people Hell. But their resilience calls out to me to not go ‘whining’ when things don’t fall my way. Toughen up, get smacked down, and take another run at it. Grow stronger.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

#1: I’m loyal to my crew. Tell someone you prize loyalty, and they might think of a faithful hound dog, but I think of Tony Soprano. I think of Jimmy the Saint in Things to Do in Denver When You’re Dead. You’ve got to stand by your friends, colleagues, and comrades. Their challenges are your challenges. Their aspirations are yours. My crew is my clients and those who work with me. Every member of every team I’m on in any capacity knows I’m working toward our shared goals and I’ll help them if I know how and have any energy left to give. And just as quickly, I’ll tell them if I don’t know the answer, rather than pretend I do in order to save face.

My crew is in the high double digits. I work with a lot of people. Sometimes they’re not aligned at all, and I’ll even settle disputes. That’s loyalty, too — trying to see from the perspectives of two people you care about who are at odds. You have to temporarily suspend self-interest. I don’t understand people who could play on a team and not give all they have to their teammates. I don’t hold back. That sense of being musketeers who stick together, comrades in arms, has been crucial. There’s an adage from BNI (Business Networking International): “Givers gain.” I know loyalty breeds reciprocal loyalty as well as trust, and I’ve benefited from that, but the most powerful thing it has engendered, for me, is a community in which I can move and breathe and be respected. I prize that most of all. Wherever I go, I start building a crew.

Thinking this way has expanded my organization. I know a lot of business owners whose companies don’t have budget for a guy like me. Nevertheless, I get value from partnering with some of those businesses. They improve my life. They bring me joy, delight, and comfort. Occasionally I like to do something to help them advance their cause, even if only by inches here and there. I do it just as if I was ‘on the job’. I say, “I took the liberty of helping, so here you go.” To my business partners, when an eyebrow gets raised, I say, “Oh that guy. He’s part of my organization.” I think of my organization as constantly growing. The way I see things, everyone I deal with is potentially part of my organization, if they deal honorably with me and trade value for value. I won’t forget them, if a time comes when I can provide a service. A guy makes me a great sandwich, talks to me a little over the counter, adds some extra goodness to my life, maybe hands me a little something extra in appreciation of the bond. I’m going to remember that. So it’s not just being loyal to your crew, it’s remembering who your crew really is. It’s those people who have taken the trouble to make our lives better. We can’t just disregard that stuff.

#2: I’m candid. If someone gives me a greenlight to tell them exactly what I think, they’ll get a direct answer, and as exact an answer as I can provide. It’ll have no buffer of safe (for me) ambiguity and no calculation as to how well they’re going to like it. The result is clients, colleagues, and friends can bank on what I’m telling them being the best I’ve got to offer. I might piss them off, but they’ll know I’m not shining them on.

One of my favorite moments in Gettysburg, a spectacular film based on Michael Shaara’s Civil War book, Killer Angels, is when General Longstreet says to General Lee, “I’ve been a soldier all my life. I’ve fought from the ranks on up, you know my service. But sir, I must tell you now, I believe this attack will fail.” You can barely buy that level of honesty. It’s priceless. It’s essential. Had Lee heeded those insights, granting that the historical account of that dialogue is disputed by some, the tragedy written in blood that so moved Lincoln in his Gettysburg Address might have been averted. Longstreet risked the respect of his superior, his professional standing, and his career reputation arguing with the most revered commander of the Army of Northern Virginia, for the sake of his crew and his commander’s success. The duty of candor was more important. What he retained for that candor was the trust, of both his soldiers and his commander. I share that core value.

My other business is a consulting firm called Free Agent Source Inc. Imagine a full-on consulting firm that delivers enterprise projects for corporate clients in the most obvious, least circuitous manner, with the project owner’s priorities driving the boat, instead of the “land and expand”, spend all your time on PowerPoint presentations and outright malingering that’s come to typify the mainstream consulting culture. We’ve all seen it: keep pushing out the timeline and adding on additional meetings. We’re a no-nonsense bunch, fiercely independent, and performance tuned to get things done. We pretty much suck at PowerPoint presentations. But sometimes we have to do them, so my partner is routinely bringing me his deck and saying, “What do you think?” We usually spend a couple of minutes on, “Do you mean what do I really think, or do what do I think that I think you’ll want to hear, or what do I think the other guy will think?” The answer is always the same: “Give it to me straight, like a whiskey too precious to water down.” In exchange, it’s funny, when I show him something I’ve written, I get similar utter destruction of some of my most precious copy. I wouldn’t have it any other way. I don’t put water in my Scotch. I don’t need someone to water down the hard conversations.

#3 I’m invincible. As soon as you say that, someone punches you on the arm and says, “did you feel it?” If you don’t have a friend like that, I’ll introduce you to my go-to tough guy, Chris Harper. He tests out my most precious self-descriptions with reminders that I’ve lost not a few wrestling matches where he was only using 20% strength. What I mean by invincible is the capacity to meet the impossible hurdle with irrational resilience. I’ve gotten this strange grace that I feel unworthy of — to endure extraordinary hardship and come out achieving unlikely things. Given how I grew up, and the people who didn’t make it, there’s no rational justification for me even being here, let alone having what I have. I only know how to call that being “invincible”. It’s a gift, for which I’m incredibly grateful. There’s another song by Sia. I don’t go in for pop music, but I dig Sia. She has come out of flame and thunder, just like me, and she’s strong. The song is Titanium: “I’m bulletproof. Fire away. It’ll ricochet.” I have that hashtag (#titanium) on my social profiles. I rose through tough times. I came out titanium.

I really dig stories — it’s probably obvious. They play an enormous role in my business of distilling and conveying client stories for MadPipe, my marketing firm. Stories compress immensely powerful ideas and encapsulate them in universal memes. In Knockaround Guys, Vin Diesel’s crew is challenged to a fight. His character says, “500 fights. That’s the number I figured as a kid. 500 street fights and you could consider yourself a legitimate tough guy. You need them for experience. To develop leather skin.” In Fight Club, Tyler Durden’s alter ego says, “A guy who came to Fight Club for the first time, his ass was a wad of cookie dough. After a few weeks, he was carved out of wood.” Sia is that way in my view. Just watch her sometime — pull up a video of her on SNL. She’s retained an incredibly precious humility even after breaking out “Like a Bird Set Free”, achieving fame and acclaim and emerging carved out of “Titanium.” As a kid, I liked the Louisville Lip, The Champ, the Greatest. If you were around then, you know who I mean.

Growing up, when things were hard, I used to look at Muhammad Ali, the philosopher of the boxing ring, as a source of encouragement. There was nothing quite like the privilege of living at the same time as that man and seeing him on TV, especially given what was happening with civil rights and the challenges he faced to be respected for who he was. Ali is thought to have said, “Impossible is just a big word thrown around by small men who find it easier to live in the world they’ve been given than to explore the power they have to change it. Impossible is not a fact. It’s an opinion. Impossible is not a declaration. It’s a dare. Impossible is potential. Impossible is temporary. Impossible is nothing.” The fact that it was actually an ad copywriter that penned that observation for Adidas, who used Ali’s picture with it, doesn’t diminish it for me. We all knew what The People’s Champion was saying when he belted out those legitimate one-liners: “If you even dream of beating me, you’d better wake up and apologize.” It’s more complex than mere ‘tougness’ and much simpler than conjuring what people call belief in oneself. It’s the simple observation that the flame that burns in a deluge cannot be quenched. A close friend who knew me when I was still a boy said to me one day, “you’re a bonfire.” Like Ali, I’ve concluded by experience, observation, and conviction, that I’m unquenchable.

When I got cancer, a new opponent from within, and we cut it out of me and threw it away, my favorite thing I got to do was work a little from bed. I could only get in a couple of hours at time. I could have just watched movies, but what I liked best was remaining effective. The feeling of power that gives any of us is palpable. I asked them for the piece they cut out of me, so I could keep it in a jar in my office. I could tell prospective clients, “I did that to cancer. Imagine what I’m going to do to your problem. Now let’s solve for X.” Unfortunately, there’s some sort of rule around medical waste, and no one gets to keep their tumor as a trophy in a jar of formaldehyde. I might be invincible, but bureaucracy is no slouch, either.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

It was a series of leaps. I left a Midwestern home at 17, with few professional skills and no real prospects. I knew a lot of things, but I didn’t realize I knew them, and didn’t know how to parlay them into work. I spent a number of years scraping together a living doing day labor for cash — everything from pouring concrete to rolling hot steel in a foundry. I bought day-old bread from an outlet and donated blood plasma to make ends meet. It was often not enough, so periodically I had to pawn whatever I had, borrow money, or rely on gifts from relatives. I didn’t care much for my life at that time.

I got into a fundamentalist group, initially as a ticket out of despair and depression, and at the same time started working my way through college, getting what grants and loans I could. I never stopped scanning around for a possible future. I quickly found those two worlds incompatible and finally had to choose. Education revealed more inconsistencies in fundamentalism than the other way around, so I stuck with the education and kept trying my hand at the usual student jobs. At one point, I got fed up with the standard food service and delivery jobs and decided to do something I’d tried as a kid. I started mowing lawns for a living. A friend invested a bit of money in that endeavor, more to help me than to turn a profit, and I bought a truck, signs, and equipment, printed up flyers, started doing door to door sales, and made a real go of it. It was largely seasonal work, but for a good chunk of the year it paid the rent, and I liked working outdoors. I grew lean and muscular, and I ran that business all the way through college.

College took me ten years, going part time, but then I graduated and started grad school where I quickly encountered people who had seen more of the world that I had. I envied their opportunities. They seemed to have advantages that I didn’t. I knew from years of study of history, philosophy, and the humanities that the world was much bigger than I was getting to experience, but I was still running a “mow, blow, and go” service and didn’t have any conceivable way of getting abroad to see for myself what was out there. A professor recruited me as part of her own side hustle for a contract teaching gig in South Korea, and I jumped on it.

It was like leaping off a cliff. I arrived with maybe a hundred bucks in my pocket, no knowledge of the language, a bundle of misinformation and assumptions about what to expect, and three days later the bottom fell out of the Pan-Asian economic system. It’s now known as the Asian Financial Crisis, and it was their version of the 2007 crash. I spent the next several years effectively stranded abroad, working within a system that could be deeply exploitative of foreign workers, but instead of fleeing I doubled down and dug in. I finally returned as we started the new Millennium — with money in my pocket and a vastly evolved perspective on the shape of the world. I don’t mean just geographically, but conceptually. I tell people, “Draw a circle around anything you want, and call it ‘the world’. I’ll draw an open-ended circle around that, and say the world is actually bigger, and much of it remains unknown.

The world is big. Living as though it’s big and open-ended is a significant shift in mindset. You can’t go back to parochial attitudes after that without doing violence to a part of yourself.

In 2000, I did B2B sales at which I excelled. I started grad school again, but quit because the commissions flowing in to my bank account from full-time selling were too lucrative to pass up. But I wasn’t going to settle for one or the other. I ended up finding a way to do a grad degree entirely by distance learning, going from cold calling to teaching rooms full of salespeople the techniques that had made me successful, and using my workplace to conduct the graduate research project using sales and training data. I parlayed that diploma into a career jump which tripled my income, and then I made a mistake. I spent the decade trying hard to fit into a traditional organization. It was not a comfortable fit.

In 2007, the bottom fell out of the American economy, the real estate market crashed, and I was working for the world’s largest real estate technology firm. I’ve never seen so many people laid off so fast. When Countrywide went down, it was like a giant gong sounded “last call”, and there weren’t enough rooms to hold all the exit interviews. I got laid off in the cafeteria, because there were still people crying in the offices. You could have played hopscotch on the rows of empty desks. The upside was I decided to start a marketing company. My former employer became a referral source, and I spent the next three years saving as many small businesses as possible from the effects of the collapse. I was teaching again — showing business owners who had never done digital marketing a new way to acquire clientele. The mission of the brand was simply put: “I’ll keep you in business, and you’ll keep me in business.”

I couldn’t believe that I was actually getting a life I wanted. It seemed too good to be true. I had my own business, and I was helping people and building a crew. I was also afraid. It was the last time I can remember being afraid, but even a little fear skews one’s choices. The idea that I was entirely in charge of determining where my next meal came from — no student loan to tide me over, no W-2 paycheck, made me nervous. I’d always hedged my bets a little. I was used to wearing multiple hats and doing several things at once. So that’s what I did. For my business, I was salesperson, recruiter, head of operations, and even my own bookkeeper back then. On top of that, I had a full-time corporate job. Taking another conventional job was a mistake, but the contrast it provided was invaluable.

That last job convinced me that flying my own flag was the only way for me. In a traditional organization, loyalty can take a backseat to one-upmanship, and unfettered candor is likely to be resented. I had plenty of money coming into my own brand, and I began to wonder what I was doing taking orders from people that accepted my dedication and zeal but frequently didn’t reciprocate with respect and comradery. Instead of a crew, I felt forced into a competition with my fellow employees. So, I made a deal with myself: accumulate X-dollars in my capital account, using the paycheck to invest in my business, and then shred the resume. We brought the 10-million dollar corporate project we were working on to completion, and that put exactly the right amount of bonus cash in my hands, so I tossed the college degrees in a drawer, donated my “work slacks” to Goodwill, and vowed to never take another traditional job. I’d fly my own pirate flag from then on.

There was only one problem. 2010 and President Obama’s leadership brought hope to the American horizon. We saw the biggest economic recovery in our nation’s history, and my business was built on the idea of riding through economic turmoil. It wasn’t designed to operate in a climate of prosperity. Business growth tapered off. The pitch of getting through tough economic times wasn’t working anymore. The only thing I could do was take another leap.

And how did you “reinvent yourself” in your Second Chapter?

You could take the entire chapter until now and call it figuring out who I was and what I knew how to do, and what the life I wanted felt like. What I still had to figure out was how to make it last and grow, and what that looked like. I had taken a lot of leaps away from things, but only just started leaping toward something. I wanted a recession-proof business built to work with aspirational partners that created around me a community of peers.

I decided that not only was selling survival no longer a practical option, I was tired of it. I wanted to work with clients keen to thrive. I was also tired of where I was living. As a small child, I’d watch stories of New York, Boston, and Philadelphia and the culture they represented to me contrasted deeply with the parochialism I had experienced routinely, for all that middle-America had taught me and the value I still sometimes call out and protect. There are a handful of things I still can’t find in New York, but I’ve never looked back from that trade-off.

On the cusp of 50, I took a deep breath, tore down my business to the bones, built a new one on the skeleton, which involved letting most of my clients go, and I moved to New York City. Effectively, I started a new life, and it worked. My new brand prospered, and I was happy. If I stopped there, it would leave out what all stories have that make them great — the inevitable “and then the bottom fell out from under our hero.”

Then came the cancer diagnosis. You’re never quite ready to hear something like that. But I’ve got Viking in me, and I turned into the wind and faced it. I put my affairs in order, made arrangements for my loved ones, left instructions for disposing of my estate and, freed of those concerns and encumbrances, went and found a surgeon who would be a Viking with me. That’s Nipa Gandhi over at Mount Sinai in Manhattan. I interviewed other people, some who had been doing it longer, but Gandhi had three things I wanted. She refused a one-size fits-all template, where others kept citing the textbook for what to expect and what had to be done. She kept the ball in my court, so I could drive the process. I was the General of my care, and she was my special forces. She joined me with a vision of winning. I’ll take someone like that every time over all the ribbons, trophies, and 40-year-old diplomas in the world.

I thought I was going to die. I didn’t tell people that. Why burden others? Besides, I wasn’t afraid. Death seems miniscule compared to the obstacles that dot the landscape of the ordinary people every damned day. Where are the people I saw stand and face worse, growing up? Where is Muhammed Ali? Those people are victorious, whether they won or not, because they stood and didn’t back down. This rare gift I’ve somehow acquired, for which I am grateful to others, is the ability to fight on, regardless of whether I’m outnumbered, likely to lose, and surely doomed. I don’t need a guarantee. We all like success, but I think the kind of people who are successful consistently can stand, and face anything, even with no assurance of victory. Still, I thought, “this is how the story goes. It’s a tragedy.” I was surprised when I woke up, unable yet to open my eyes, and they were feeding me ice chips and asking me to rate my pain. I wasn’t fully aware and asked for more “pain chips”. I joked with the nurse. Then it went black again, and I opened my eyes a few hours later in a room overlooking the Hudson River.

Beforehand, I had to tell some of my colleagues and clients that I was going under the knife. Some people who heard about it said, “I’m so sorry.” It was like they were already mourning my passing. I realized no one knows what to say in those moments, so I’ll tell you. You say, “Go kick it’s ass. I mean it. Murder that cancer. Be a Viking. Come back with your shield or on it.” A couple of friends said exactly that. What I needed, at that time, was to thump my chest, square my shoulders, and tell it “I’m coming for you. You will not survive. You can try to take me, but I will beat you.” I thought I would lose, but I determined to win. You really can hold that contradiction in the mind, if you have the heart.

Well, we murdered that cancer. I didn’t think I was coming back, but I was going to make it buy every inch of my life at a dear price. I figured, in the end, it would outdo me. It didn’t. We gave it the heave ho, and I returned stronger and ready for the next thing. The trophy is the scars — little knife wounds of resilience.

Ali said, “Live everyday as if it were your last, because someday you’re going to be right.” There’s a thing that happens when you face death with defiance. When you’re willing to fight it tooth and nail and lose if you have to, but you refuse to just let it have you if you have anything to say about it. Everything tastes sweeter. Music is brighter. But those are minor compared to what it does to your outlook. I faced death multiple times as a kid, and as a young man. I’ve been shot at, quite a lot, though it was mostly in my wild youth. Yet it was never quite as definitive as cancer. Hearing you have cancer is like hearing an army of untold power has landed on your beautiful shore.

Once you beat death, solidly, even once, and even knowing that eventually you’ll lose in some distant, future fight, like an aging boxer entering the ring, full of bravado but aware you’ve got a date with the reaper and it could be this time, you mercifully lose the ability to be afraid of much of anything. It’s fearlessness with an exponent. You’re ready to take on just about anything. I don’t mean a fist fight, but stuff that’s much scarier. That could be self-doubt, embarrassment, fear of failure. It works for the other thing, too. A nearby restauranteur said, “be safe” as I was leaving one night. This is when shootings were up by quite a lot in Brooklyn. But I laughed. I faced cancer. What can anyone out here do to me? Please.

We might not think we’re afraid of anything. Fear has a way of covering its tracks. It’s cloaked a lot of the time and operates by stealth. Here’s how I know. I’m in the middle of my life, and it dawned on me, I’ve got maybe the same amount of life left as I had starting out. I always wished I could go back and start over knowing then what I know now. Regret is good. The only people with no regret are people with too little life experience to be aware of their mistakes or sociopaths who don’t feel responsible for them. There are a dozen things I would have learned and a dozen things I would have avoided, because now I know there’s no water in that well. But actually, that choice is right here in front of me, or any of us if we’ve got some life left in us, even if it’s just ten years.

In ten years, I could learn to play guitar like Eddie Van Halen. You don’t have to believe me, but I know it’s true. I could become a black belt in an Okinawan karate. I could learn to speak a couple of extra languages fluently. I could skipper my own boat. I could do all of those things, while hiking, dancing, boxing, writing, and continuing to build businesses. 50 is the new 16. We just tend to sleep through it, because some fear has pulled the wool over our eyes — maybe fear that it’s too late, or just something an adult doesn’t do.

People talk about a mid-life crisis, because there’s some template for how you’re supposed to plan out your life, just like there’s a template some doctors have for how we quietly accept our fate as we let the textbook tell us our prognosis. I have a vision of winning. I never got to study music, so I’m doing it now. I want both boxing and karate, so I’m studying both. I was 16, the last time I threw a front kick like I did the other day. I own an electric guitar.

It’s not a crisis, it’s an awakening. Nothing is left that can make me afraid, ashamed, or uncertain of my direction. King’s book, “Hearts in Atlantis” has one character ask another, “Do you have the heart of a lion?” My answer is that I work out every day. I hike, dance, boat, spar, study languages and music, work like a demon, and I’m carved out of wood. Hashtag titanium. Not long ago, the itch of the serial entrepreneur kicked in again, and I launched yet another side business.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

It didn’t happen all at once. It’s a punctuated equilibrium — less a single trigger than a 21-gun salute spread over a few years. But the major beats in the story are these:

Moving to New York in 2013 was huge. One of my favorite documentaries is Blank City, which is about the creative crucible of New York City in the eighties. It’s superb. And someone in it said, “I came to New York, not really intending to spend the rest of my life here. I immediately felt at home, like so many of the dispossessed do.” I have a home, now. I really do think of it as home. I’d been visiting it whenever I could for a few years, and I just knew. I never had that before. I dig Jersey, and Northern Washington, and I could live in those places. But my first home will always be New York City.

Building a brand based on aspiration instead of desperation was an enormous pivot. Letting go of my only guarantee of independence, the book of business I built up in the early years, certainly made me nervous. But I saved, hedged, and inevitably accepted the risk. It was both the focus on aspirational thinking and risking the most valuable thing I own — my freedom and independence — that conditioned me to venture even farther. My friends have always called me fearless and adventurous, but I think choices like these make you more of who you are — more fearless, more adventurous still. They add an exponent to what you are.

I’d be remiss if I didn’t give credit to Landmark Education. They’re headquartered here in New York, and they deeply augmented my thinking. Josselyne Herman-Saccio over there sparred with me intellectually and it’s probably the best contest of starting from an outlook of abundance versus coming from a place of lack I’ve ever witnessed. We had a fairly rapt audience. All I did was try to decimate all that ‘positive thinking crap’ with my formidable training in logic, and all she did was keep comparing the outcomes of starting from what we want more of instead of what we wish were less. It was frustrating, hilarious, powerful, and it changed my life. I’ll never forget it.

Once I was starting from what’s possible rather than what’s wrong, my brand really took off, my standard and quality of life went up, and a seminal question arose. I’m having a conversation with a colleague — my business partner Steve Pruneau — and I mention how much I like stories and storytelling, and how different it is from my ‘day job’. He says it’s really not, and why can’t I bring that passion to my business? I chose right then to pivot and take a specific approach to marketing. I decided to focus on unearthing a firm’s brand story and convey it powerfully to an audience. So, it wasn’t just client aspirations I was after, but my own, and I made them align. Story is one of the most powerful and universal ways to connect with an audience, and many of the good ones are untapped resources. They don’t get told. I’m all about collecting, curating, and amplifying great stories.

Then there’s the bad boy, cancer. It was actually quite good for me. It was an opponent trying to take everything away — everything I have. And the first thing I did was dig in and arrange to do my duty to those I care about — my crew, if you will — my organization. The second was insist on candor — it might indeed kill me. Death is possible, but I refuse to flinch or let it get me down or just avoid thinking about it and watch a lot of TV and eat ice cream while I wait for an outcome. Instead, I planned my attack and taunt death, tell it to expect combat, and dare it to try and take me, which is insistence on being invincible until I’m not. You go into a prize fight swinging like Ali, and you come out of it smiling through bloody teeth for the camera. It was worth it. It tells me who I am. Guess what I’ll do next. Anything. Whatever I always wanted to do that I’m passionate about.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

Fearlessness and aspirational thinking are a skillset. I think first, however, you need a baseline. A lot of people have incredible skills. We’ve got a nearly invisible potential workforce of people who, for one reason or another, don’t fit a particular template of superficial and relatively unimportant characteristics. They don’t look the part. Often, they’re not able to make the leap to finding what they’re ultimately ‘meant’ to do, because they’re too busy surviving. I think first you’ve got to get to a place where you’re doing some things that create a life closer to the one you want — for me it was entrepreneurship — and from that ground, you can begin to seek more clarity and refinement which could result in doing something completely different or doing the same things but in an entirely different way.

Melissa Whitaker, a fine artist who does bespoke digital illustration for business clients — she’s the official artist of my brand — started out doing real estate. She didn’t really know what direction she would take a commercial art practice. She had to get to a baseline of producing art full time, and then start seeking clearer answers to those questions. That process has mirrored my own, and I think it’s quite common.

As a young man — a kid, when I built my first business and worked my way through college, I discovered I could both sell and teach. I knew how to do manual labor and liked that I could do it. It was invaluable to learn to be effective with that kind of work. But discovering that I knew how to sell work, and teach people to do certain kinds of work, including how to sell, was huge. I thought I didn’t know how to do anything, but I just didn’t know that I knew. It was locked up in a context of ‘getting by’.

If I thought back far enough, I used to Watergate the doors to the computer lab in my High School (a trick I learned from watching Watergate reporting on TV as a kid — you put tape on a door’s lock bolt, so it doesn’t latch) and I taught underground classes in the evenings to other kids — members of my crew — who weren’t allowed to use the lab. In the early days, tech wasn’t a right; you had to have really high math scores to get in. But I knew tech was a possible future and would be a life skill for these kids. I was always teaching. I was always finding untapped resources.

Going back even farther, when I was twelve, in Middle School (they called it Junior High back then), my father gave me unlimited use of his tools and let me take all the wood I wanted from his basement shop. As an engineer, he was skilled in everything from radio circuits to construction. I had helped, in the way kids do, which is nominally, with a few projects. Seeing a zero-overhead, zero startup cost opportunity, I started a little business making and selling rubber band guns to neighborhood kids. I even got some competition from copycat producers, but they made an inferior product because it was easier to do so, and I prospered. It came to a halt when a boy shot his sister in the eye. She was fine, but it brought tears and scared parents to our door, and I was ordered to shut down. Still, it was my first brush with selling and entrepreneurship. It’s funny how you can forget what you know if no one tells you that you’re good at it, and you don’t keep doing things to reinforce it, especially if your first plan didn’t work out as intended.

Out on my own, it was only after dumping the crappy jobs and spot work and launching my own business that I was able to learn some of what I could do well. That first adult business, landscaping, was an important step. Fast forward twenty plus years, and I have another unearthed skill. I can find, craft, and tell stories effectively. It was there all along. It’s part of why I could sell. But it takes a crucible of learning, fraught with obstacles, to teach you what you already know so you can choose to hone it and improve.

When I was considering the move to New York, I said to Steve Pruneau that I didn’t think it would happen. Too many hurdles stood in the way. He said something I’ll never forget. “You don’t get anywhere by looking at the barriers. You get there by deciding a thing will happen and, because you’ve committed to it, seeing opportunities you wouldn’t see if you were still looking at the barriers. It’s incremental, but that’s how it happens, when you reverse engineer achievement.” That was the TNT that broke through any roadblocks in my way. I made the decision, and here I am. I tend to trust that anything I decide will happen is going to happen. I don’t have to know how, at first. I just have to commit to it.

How are things going with this new initiative? We would love to hear some specific examples or stories.

I love my life. In social media, when it asks your “status”, that’s what I put. I think that’s the standard by which success is measured. Someone always has a template, but the template really only applies to them. If you don’t love your life, you have to add the word “yet” and determine that, even though you don’t know how you’re going to make it happen, you will do so. Even if it looks insurmountable, and you will almost certainly fail, reject that vision in principle, and keep looking at your goal. Nurture it. Cultivate it. Say it again and again. Don’t turn back from it. I don’t mean to offer advice so much as to describe something that could sound like magical thinking or even like arrogance in a different light. I love my life even though it’s not done yet. When someone asks me what I want, I just say “more”. I want more of this. I don’t know yet what that looks like or how it’s going to happen exactly, but it will. I’m set on it. I’ve made up my mind. I love my life, and I will have more of this. There are no storms that will dissuade me. So, that’s how it’s going. Pretty damned great.

Getting more specific, my business thrives, I prosper, I have a community of peers, and my life is filled with delight and wonder. An army always lands on the beautiful shore and threatens it all. That hasn’t changed.

My boy, my baby boy, my beloved rescue dog of fourteen years, has gone deaf and blind, has epileptic seizures, and was recently diagnosed with both heart valve disease and a brain tumor. He is with me nearly every moment of every day. He’s two feet from me as I say this. He’s with me on every client call and with every project I undertake. If you look at my LinkedIn profile, you’ll see him in a chair in my office, while I work.

I really identify with the hurdles he has faced. He was dumped in the woods as a kid by breeders, left in deplorable conditions, and was shy of people when we came together. In his early years, I rocked him as a mother would an infant, and he sees me as his world. He doesn’t do well without me, and I love him more than life. I will stand by him as his defender and protector for whatever years, if any, remain. I’m not heartbroken. I can’t be broken, and that lets me do as right by him as I know how to do. I’m simply facing these challenges with him as long as there is anything to face.

Dogs are people. I’ve lost a lot of people in life, and I always wish I had done more, been more, been there for them more. I am trying every day to redeem every failure to be all that I can be for anyone in my crew with him and with all those in my life. I am learning, growing, and serving to the best of my ability. His name is Moongchee which, in Korean, means “Incorrigible” because, like me, he has an iron will — he can’t be broken. It’s interesting how many business leaders I talk to who immediately understand and open up with me about their beloved pets or tell me about the thing they’re facing that could cost them everything. The reality is that when you build a life you love, and you are being true to who you are, nothing can ever take all of that away. A life we love is a fortress. It’s impregnable. It’s titanium.

I am teaching my boy to trust walking with me on the sidewalks of Brooklyn without any sight or sound to guide or reassure him. He just has me, giving him love, and letting him know I’m still here. I’m still here.

I suppose that’s not a typical business story, straight out of Forbes. For me, however, it recapitulates why I do what I do, what it means to me, and the commitment I bring. We are these kinds of business leaders, because we are these kinds of people. The divide between commerce and our personal identities is artificial, and it’s not very robust.

I recently worked with Lily Dulberg on the data science team of The Clark Hulings Fund to produce its seminal report — The Report on the Working Artist — which outlines the hurdles to prosperity faced by creative professionals, and how supporting their entrepreneurial efforts can produce objective, measurable change. With the right training, tools, and support, those business owners’ sales improve, their revenue increases, their incomes rise, and they become job creators that do increased business with other industries, from financial institutions to manufacturers and suppliers. That drives increased economic growth at the local, state, and national level. Seeing others prosper as a result of one’s work is priceless. One could stop there, and it’s more than enough. But it doesn’t stop there.

I got a note from Lily recently which it would be immodest to quote, because it’s really glowing, but I’ll say that hearing how focusing on aspirational goals affected the professional path of a colleague, added an exponent to her practice area, and helped her make important decisions about her future is just one extra data point that tells me I’m on the right path. When a member of your crew borrows these ideas and builds their own unique edifice on them, so she can love her life as much as I love mine — that’s irreplaceable for me. I dig it. I can’t tell you how much I dig that. Building a life we love is contagious. Aspirational thinking is viral. I want more.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Certainly, I have not achieved anything alone. Steve Pruneau, my business partner at Free Agent Source Inc, Jean Tang at MarketSmiths, the copywriting firm, and Elizabeth Hulings at The Clark Hulings Fund, have each consistently turned to me as a “sounding board” for exploring new ideas, a problem-solver for overcoming challenges, and a collaborator for adapting to changing circumstances. We might not think of trust itself as a contribution, but it’s incredibly powerful. When people plug you in to their goals, ask your input in solving problems, and rely on you to add value and give it to them straight, it doesn’t just reaffirm that you have something to offer — it underscores the value of relationships built on trust. It’s an honor to connect with people at that level.

When people know you’ll look at the thing they’re looking at, make their purposes your purposes, their challenges your challenges, and deal honestly and reliably, that’s a sound basis for meaningful relationships in general. Each of the people I mentioned do that and reciprocate.

I think a lot of people treat work relationships as a special category. But work is how we will spend the most productive hours of at least the most energetic years of our lives. It’s how a lot of us express our deepest aspirations and is perhaps the primary way we interact with the world during most of our waking hours. Professional relationships, therefore, and I’d call them professional friendships, are utterly foundational. The community that arises from our work has the potential to be predicated on our mutual pursuit of transcendent meaning. We hold up stories of amazing friendships, passionate romances, and deep commitment to family. I look to work relationships as my primary source of community

I also credit teachers, though less recently, for maintaining belief when my own belief wavered. I suppose it’s more dignified to say that Steve Jobs inspired me. But I’m not ashamed to say that, decades later, I still remember how individual teachers nurtured my gifts when most of the people in my early life were saying I’d never amount to anything. Teachers pushed me to compete and lauded my triumphs when others only asked me to keep up. One teacher handed me machines to repair and difficult novels to read, when I was just keeping my head down and knocking out the requirements. She could see my creative mind was like a bird in a cage longing to fly. It’s the same thing, really. A teacher says, “I don’t know to fix this. Maybe you do.” Or “I think you can tackle more substantive problems. Let’s not under-utilize your capabilities.” That’s huge.

Another teacher put the oddball kid on the staff of the school literary magazine, when others just shook their heads. I sat on the back row. I had long hair. I smoked. I skipped more classes than I attended. I stayed out all night, rocking and getting into bars. My friends were hoods. That doesn’t embarrass me; they disdained a culture of “fit” based on popularity, what clothes you wore, or how much money you had, the very school culture that intentionally prepares one for that of the traditional corporation, and they welcomed me. I wasn’t the iconic English major. But when I recited Coleridge from memory, the teacher chose that over superficial appearances. Needless to say, I never missed his classes. He put trust in me. In college, a Humanities instructor insisted I read Boethius, because the textbook wasn’t going to go deep enough to satisfy my curiosity and she knew I needed more input, not less. I had my share of teachers that went through the motions but, consistently, teachers saw a fire in me and poured fuel on the flame. Without them, where would I be?

There’s a thing we do in a world of LinkedIn profiles and resumes of presenting ourselves as a finished product. We have our ‘personal brand’, and it’s got no real backstory. Or the backstory is sanitized. I don’t mind saying I grew up rough, had a raucous youth, and would drag race on the public streets for gas money while pumping out Black Sabbath and Uriah Heep at volumes that rattled June Cleaver’s windows. I’m glad for all that, too, because all that formative rebellion provided the esters without which the distilled life would have lower proof and less flavor coming out of the distillery. We’re all a mix, and the failures and flirtations with the edge are part of the character that makes the brew. Like any spirit, there’s a finishing stage, and I count the contributions of later years in human relationships.

Can you share the most interesting story that happened to you since you started in this new direction?

COVID-19. I can feel the eyes rolling. Really? We’re all ready to get past it, right? But it’s been a fascinating year. Obviously tragic loss of life, every person of which is someone’s mom or sister or son. It’s brutal. And immense destruction of wealth. That sounds theoretical, but we’re talking about people’s life savings gone, their businesses closed, their dreams dashed, and a lot of people upside down on debt. People have lost their homes, and their aspirations teeter on the unknown. Every third window on some commercial streets has a ‘for rent’ sign with no takers. I hate it. I think it’s inexcusable. I think a lot of it was preventable. I think it underscores that a lot of people have prioritized ideology above human beings, and I despise that. Poor and immigrant populations, as usual when we tolerate misuses of power and neglect at the highest levels, have suffered disproportionately.

I also think it was a contributing factor in an attempted overthrow of our form of government and that’s iconic of a breach in mutual trust, which I’ve underscored as essential to communities that collaborate in the pursuit of goodness and meaning for all participants. We might want to move on, but we’re going to be dealing with the damage for a century at least. That’s not about lacking optimism. It’s information readily available in our experience of human history.

Given all that, it might seem inappropriate to find any joy in it. And indeed, the opportunities for joy in 2020 were disproportionately the province of the affluent. But it does no good to deny one’s experience, just because it’s not universal. I’ve been doing what I can, back to my entrepreneurial roots as a social entrepreneur helping small entrepreneurs, who are the perhaps most vulnerable, weather the storm. But, for instance, a neighbor of mine said to me the other day, “The streets are quieter. I’ve gotten things done. There’s something to be said for people staying closer to home.” I can’t disagree, in my own experience.

Suddenly, there was time to learn something new, to start a new thing, and a whole host of people no longer see a need to spend most of their waking hours in a cubicle. The birds are out in greater numbers. There is song in the streets. In my neighborhood a band played every night on someone’s front porch, to inject some beauty in the midst of devastation. People said “thank you” to mail carriers, and tipped delivery people extra. It would be a mistake to ignore the rays of sunshine for the sake of the hurricane, just as it was a mistake to deny the weather reports because they were, for some, ideologically inconvenient.

My own business did not suffer measurably as a result of the pandemic. I did not suffer personally. I did not lose a loved one. I prospered financially and emotionally, and without guilt. In the evenings of 2020, I walked long distances every night. Social distancing was good for my constitution. I ate more home cooked meals. I spent far more time with my dog. It was a time of clarification that allowed me to more fully elaborate the reasons for my choices, and what I want. It was during COVID-19, which isn’t over, that I started studying music — a lifelong goal.

I cheered on people who didn’t fold, flee New York, and hide in some rural bunker. I saw yoga schools go entirely virtual and triple participation and prosper. I helped conferences convert to virtual and proceed as planned, learn how to do digital and decide to never go back to a purely analog experience. I saw more books being read and more runners than ever. I watched a live concert on Zoom. Someone called 2020 a “golden age” for pets. A restaurant PR consultant saw her business dry up, pivoted, and became a digital marketing firm.

All of this underscored for me a key value — that of resilience. Human beings are highly adaptable, when they want to be. When I see legacy industries like coal, failing, and people ask, “What are the miners supposed to do? Learn a new skill, at 50?” Yes, I think that’s exactly what has to happen. That, and start living in a world where we all need to nurture more than one capability. It might be unrealistic to say everyone’s going to get a green job, just as it’s indifferent to say, “sure, those people are screwed, but other people will get work in the new economy”. But it’s also lazy to suggest anyone should be exempt from having to change, and monstrous to sell out our mutual accord to anyone that promises political favoritism in exchange for loyalty and hate.

Cycles of change are coming faster than ever. If a pandemic accelerated that, for some, it didn’t cause it. Whatever we’re doing will evolve massively in some number of years, and if we dig in and keep doing the same things, we won’t have a pivot to make. Some things have to change just because it’s stupid to saw off the limb on which we’re all standing. Saying gravity is a hoax doesn’t stop it from killing us.

The idea that we can do one thing all our lives as long as we empower some demagogue to protect it from competition, changes in customer demand, and failures of bureaucracy, is magical thinking. We’re not going to go back to coal. When’s the last time you boarded a steam ship or heard the whistle of a coal-powered train go by? We’re not going back to lamp oil and horse-drawn buggies either. So, the quintessential skill of the future is not one thing, it’s adaptability. That requires us to be multi-faceted, self-reliant (instead of relying on bailouts and rescues) and to have the personal courage to stop doing the thing we thought was going to typify our whole lives and do something new. It requires us to be prepared for that. We must see many possible implementations of our dreams, not cling to any one of them as the only possible answer.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

It wasn’t a struggle to believe in myself. It was a struggle not to believe what others said about me. When you’re a kid, you think, at the start, that other people know what they’re doing. You believe they know what they’re talking about. You trust them when they tell you a thing is this way and not that way. If they’re in ‘authority’, which is really just a lot of other people saying, “that guys knows,” it’s reinforced even stronger. We all have to find our inner rebel, and we all do at some point.

The first time a kid discovers there are people that can’t be trusted, it’s a watershed moment. He might take away the notion that people in general are unreliable, or perhaps identify unreliability with people that match the superficial characteristics of the deceiver. There are other options. It’s not a given how someone will end up seeing other people.

For me, a really valuable experience occurred when I was three. My mom scolded me for putting my socks on the wrong feet, told me to change them, and came back. I had changed them, but she scolded me for still having them on the wrong feet. “When I come back, they’d better be right.” I started to change them again, but I had an idea. I simply did nothing. When she came back, she said, “OK, now they’re on the right feet.” Later, I studied those socks, and realized there’s no difference in them. Socks don’t have lefts and rights. It’s a kid’s lesson, but I realized at three that adults could be wrong. They could be wrong on multiple levels — on both what is so, and how things work.

In fact, it’s the earliest thing I can remember learning at all. When you’re three, everyone’s a giant. Parents, pastors, police, school leaders — everyone knows what’s what, and they tell you how things are. This translates quickly, as you grow, into the realization that anyone can be wrong. It would be silly to paint that on a given race, gender, job, or some kind of status. It’s just the way people are. People are fallible. I don’t know if other people understood fallibility at three years old, but it had a profound influence on my interactions with the world and how I saw the prevailing orthodoxies and the cultural consensus of the time. It helped me decode prejudice when I saw it and choose my own code of right and wrong.

It wasn’t absolute. You might know that people can be wrong, but if a message is repeated enough times by enough people, who validate each other, and you don’t have your own fairly robust competing narrative, it’s hard not to adopt their framework as a baseline or a default. It was never so much that I needed to throw off limiting beliefs as that I needed to acquire robust beliefs in an atmosphere were few people seemed to have access to them.

Imagine you’re surrounded by alcoholics, bullies, people with narrow ideologies or parochial values. Finding light can be difficult when you’re raised in the dark. When you’re older, and you can, you go looking for something different, but you’re going to make mistakes and land on false solutions and dry wells. It took a long time to figure out that people don’t have the answers. It’s not just that people put out limiting beliefs, it’s that the culture of advice itself is largely bereft of discernment. People sell countless books and courses promising the answers to fundamental questions. I’m not a nihilist who thinks there are no answers to ultimate questions. I just think there are answers you can’t get from other people. And perhaps those answers correspond to the questions that are actually the most important.

I think all of us are on a quest to answer three questions: Who am I? What is the world? What must I do now? or (put another way) What is my relationship to the world? No one can tell us who we are. People will try. You’re good at math. You’re not very mechanical. You’re task oriented. You’re not great at human relationships. The contradictions are the most bewildering. You’re funny. You’re not funny. You’re interesting. You’re boring. You’re smart. You’re not very smart. This underscores the nature of those answers. They’re not answers that can come entirely from other people. Context is a huge factor. And you must determine your context.

I’ve spent my life finding answers for the questions I want to answer about myself, my life, my work. Occasionally, I compare notes with what I remember detractors saying, those limiting beliefs they offer, and my answers are better, backed by better evidence, and substantiated in my routine experience. Those voices fade into the ether. I occasionally check in and challenge them to a debate, but they’re just ghosts. They moan and go away.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

The people were there already. That’s because, if they’re not there before you do something hard, they’re unlikely to be there when you attempt it. In 1874, Mary Mapes Dodge wrote a now classic American fable called “The Little Red Hen”. She decides to bake bread and is visited by a number of other animals who, one by one, say some version of, “I can’t help, but call me when you succeed, so I can enjoy it with you.” If you’re going to rely on people, they have to be up for the hard thing as well as the easy.

I told my crew what I needed. Someone helped me move. Someone helped with intel on how to get things done in a new environment. In some cases, I asked for confidentiality. In others, I said “this is what I need to hear to encourage me.” You have to tell people, even people that know you, how to love you. Gary Chapman’s book, “The Five Love Languages” is about how we have different ways we need to be loved, and we can’t assume what we would need in a similar situation is what another person does. I think people put that in the context of romantic relationships, but I think it applies to relationships in general.

One of the best things ever is when someone asks, “How can I support you in this? What do you need?” It might be something we need less of — “I need to go into my cave and be alone with this.” When I had cancer, it was, “I need you to cheer from the stands while I as the gladiator face it in battle. Don’t tell me it’ll turn out all right. Pound your fist and tell me to kick its ass.” It’s crazy powerful when someone asks you what you need, then does that thing — does just what you need at the right time. Asking what you need is stronger than saying, “Let me know if you need anything.”

Doing what you need, even if it’s alien or strange to the other person, that’s camaraderie. That’s fierce. At one point, when I was tearing down the first iteration of my business and moving to New York, I said to a work friend, “I need to know I will not go down.” He said, “I will not let you go down. No matter what, you will not go down. If you want, I will list half a dozen things I will do if you even come close, but only if you need.” I didn’t need. That was superb. “We’re your crew. We’re with you.” That’s probably the most valuable thing I can hear and, while it’s not tit for tat, I pay into that fund heartily whenever I can. We’re there for each other. Us for us. It’s the Dumas school of camaraderie, as in “All for one, and one for all.”

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

I like things pre-planned. I like to go over and over the plan looking for holes. I like to plan for unknowns with several contingencies. I like fallback plans. I like sticking to a plan once it’s right. I like all of that stuff, but once a change begins, as anyone who has conducted a military operation can tell you, plans start to come apart. You’re supposed to take a lightly guarded hill but, on the night of the operation, a sudden rainstorm turns the ground to mud, the hill is heavily reinforced, and they’ve mined the only approach. Soldiers in Viet Nam lost their lives taking such a hill, when orders were pressed, oblivious of changing conditions. For that very reason, contemporary military doctrine now builds in more flexibility for the leader on the ground to adapt to changing conditions. What counts is not better planning, but flexibility, adaptability, and resilience.

Malcolm Gladwell wrote that there are two deeply entrenched ways of handling change that are largely a product of the culture into which you are born. When conditions change, some cultures pivot relatively quickly and easily. Others tend to stay on target, stick to the original plan, and try to ride out the changing conditions. This can determine whether your ship sinks in a sudden storm. Birth isn’t destiny, but it’s not nothing, and my people were known for riding the ship straight through the eye of the storm, even if it were raining fire all around them. It sounds dumb, but it’s also a kind of resilience. It breeds a kind of toughness. It can also be suicidal if not homicidal, as some of our national obstinance around the pandemic has shown.

I’ve had to intentionally learn to flex. I’m goal driven and built to get to the place we originally intended. I prefer if we say we’re going for Italian, and the place is closed, we at least go to another Italian restaurant, even if there are four perfectly good restaurants of another type around us, and one of them is five stars with a sudden cancellation and a perfect open table. We said Italian.

I like to stick to a plan, but I have learned to flex, or at least keep learning to do so. What’s the bane of all plans? Uncertainty. The more uncertainty, the more planning is either worthless or deliberately accounts for ambiguity. When you can’t account for everything, some items in a plan need to reflect a high degree of confidence that “well figure it out on the ground.” I had to accept a higher-than-normal degree of that in conducting a complete tear down and rebuild of my company coupled with a relocation. I’ve also found that the kind of clients that business attracts also demand more flexibility than before. So, it’s been useful. We start out doing one thing and, as we get to know one another, that thing evolves into something else. That’s a higher level, higher value relationship.

Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

1. You will not get it right the first time. That probably seems obvious. It’s obvious to me after starting several businesses, but I didn’t really understand it the first time. I thought I would plan it, get it right, launch, and it would either work or not work. That’s true of an omelet, but not a business. That should be comforting. It’s not a binary proposition: win/lose. It’s not an all or nothing proposition.

2. Building a business is building a community. We’ve all heard the maxim, “Business is about relationships.” I had no idea how much I would find in common with my clients, how much trust and collaboration would deepen those relationships, and how much I would grow to rely on them for the joy of productive collaboration. I spend more time with clients than I do with non-client friends. It’s fascinating to me that part of the DNA of entrepreneurship is building a community. You can study business in general, and learn a lot about client turnover and attrition, but people really don’t leave as easily as those statistics make it seem. Some clients stay forever, continue to refer people, and even become friends you have a beer with. Either way, at least for me, a deal is more likely to begin with a drink than a proposal. You size up who a person is, and you find your people through the vehicle of working together.

One of my clients came about while listening to a Frank Sinatra cover band in a cigar club in Manhattan. On a break, I asked the guy parked in the leather armchair next to me where his shoes were made. We struck up a conversation punctuated by “Sinatra” himself coming over, and we ended up exchanging business cards as the place was closing and two prostitutes lavishing attention on a former boxer at the bar started heckling us for not taking professional interest in their work. They had some choice quotes, and it remains a story I tell when the Sales team gathers for its annual summit. Another client deal was struck over caipirinhas in Union Square.

3. Your role will change many times. What you do for clients can evolve, and the job you have in your company shifts substantially over time. For clients, I might start out working on growth and end up working on brand, I might get involved with their product team and wind up helping them produce data. For more than one client, I end up leading an educational or media initiative. Through the initial collaboration, both parties start spotting opportunities to collaborate more deeply. As that happens, you end up handing off portions of what you do to other team members internally, and your place at the helm of your own company evolves.

I’ve changed titles so many times on one client team, it’s become a thing that I just periodically announce what to call me. I’ve been Director of Technology, of Education, of Marketing, of Messaging, Creative Director, and others. The last time they needed to confirm my title for a press release or something, I just said “Whatever seems to fit.” I’m involved in too many initials to count. At some point, the title and the sales pitch aren’t important, just the problems we solve and the value we deliver.

4. Laughter is essential. In traditional corporate environments, there can be pretty tight holds over the content of communications and even the conduct of meetings, which is one reason they’re so boring. It took a while to realize how much permission was really there to exhale, loosen the collar, and even cut up.

Some of my clients send me photos from Happy Hour, which I happily caption. We tell each other stories. Sometimes we confide hard things in each other. I think laughter is permission to be more fully expressed in a work relationship. If we can’t laugh, it’s just a job. I have one client who used to be in a glam-rock hair band in the 80s. He sends me pictures of his bass guitar and vintage photos of him with long hair. I fire back embarrassing shots of his period-correct twin, Vince Neil (of Mötley Crüe). Recently, I sent him a vid of me doing terrible things to a Waylon Jennings song.

5. Be the standard. “Do what you say when you say,” is something I say a lot. I value my word. My freedom is bound up in being able to give my word and mean it. It’s the badge of an independent, empowered individual. In Landmark Education, they say “be your word.” Our word is, in a way, who we are.

When I first started out, I thought that was too high a standard to apply to people who work for me. I’d hire a designer, an ad manager, a writer, and deadlines would get missed, then updated deadlines. People would get busy, forget requirements, and turn in work that didn’t match what we agreed on. I gave multiple second chances. I offered remedial measures to help people grow into the standard. It’s not productive. Training is a solution if the requirements aren’t clear. You can build skills, and you can even build habits. But you can’t build integrity. Being your word is not an impossible standard only a few people can attain. It’s the baseline — so much so that I expect of it of clients, too. “Hold up your end,” says one of MadPipe’s video commercials.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I would do one of two things.

Option one: I’d try to make it so any kid in any country could go live, learn, and work for a couple of years in a country as different as possible from their own. You need about six months to get past culture shock, and then longer to really start learning. You need to eat the same food, go to the same doctors and dentists, buy from the same stores and vendors. You need to vet the hosts. Ultimately, if kids in Texas and Utah lived in East Asia, and kids in Kabul and Jalalabad lived in Philadelphia and Seattle, you would start to unravel, perhaps, the fundamental bigotries that arise from ignorance and fear. It’d be a ticket to immense personal growth and intellectual perspective for some of these kids, and it might just be resilient enough that what they learned couldn’t be squeezed back out of them by a homogenous environment that tends to demonize the ‘other’. It’s a fraught idea in practical terms, but practical ideas start with impractical dreams. The wheel came from a desire to get over the mountain.

Option two: With a feasible plan, I’d work to eliminate the state-based system in the U.S. That’ll bother some people, and I understand that. But I think we can either continue to act like the proverbial Balkans or we can get it together more like the EU. We have fifty governments in the U.S., and the past five years have demonstrated just how unfortunate that fragmentation has become for us and for the world. This movement wouldn’t be solving world hunger, fixing the environment — that is, fixing what we do to it, or saving the whales, all of which are important. But all of that stuff hinges partly on the inaction, stalemate, and petty bickering that is the present balkanized system crippling the world’s once most significant superpower. Sad nods to Russia and China for seizing the opportunities created by precisely this problem.

The compromise between a confederation and a federal system has run its course. It’s not the system that failed us, but we have shown that we can’t live up to its highest purpose. Let’s act like a nation, not a cluster of hot mess. As a nation, structured like a nation, we could create more justice for more of our people and less chaos for the people of other nations. Remember, the UK ended slavery voluntarily by an Act of Parliament, 32 years before we ended it only in the context of a brutal civil war between states polarized by some of the same conflicts that led to an attempted insurrection this year. And even then, states created ways to perpetuate it under other names and public fictions. We don’t create justice on our shores when we don’t share a legal and political culture with similar notions of justice. When’s the last time anyone heard the phrase, “from sea to shining sea” and understood we were speaking of just such a shared culture?

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. :-)

Stephen King. I have endless admiration for what he has done, and for who he is that he has graciously shared with the world. Aside from his literature, of which I’m enormously fond, it’s King himself that interests me even more. In his work, you see a tremendous grasp of what human beings are. He finds the depths of our depravity and does so with unmatched generosity and compassion. I’m in awe of his humanitarian work.

I think he tends to shun labels like humanitarian or philanthropist. I think it’s because he sees these things as just how people deal with people, how we pay what we owe, how we honor and recognize those who contributed to the world we love and enjoy and that enabled us to pursue our aspirations. The words are shorthand, but I look at King when I want to define my goal of being a better man.

I aspire to be half the person Stephen King is. He’s a mentor for me, of how to simultaneously look at the world for what it is, no illusions, no dressing it up as prettier than it is, so that we can feel better about ourselves, acknowledging the dark, but to also love, nurture the flickering flame in a desolate wind, and love the rich warmth we’re capable of as human beings. I don’t see in King so much a fetish for evil, though I know those peculiar interests are essential to his work, and he digs bravely, gravely, and deeply enough to understand better than most people dare, but I detect a profound attachment to goodness, human dignity, and ordinary heroism.

When I was a kid, I was afraid of the dark. So, I taught myself to be the scariest thing in the dark. Whatever might be there, I would be waiting for it. When I was older, and death came for me in the form of cancer, I went after cancer the way that child would have a monster in the closet or under his bed. When I discovered Stephen King, first the books, then the man, I knew that he knew there really are monsters, and that we don’t have to be afraid to acknowledge them. His stories make me happy, and the gifts he continues to quietly give all of us make me want to be someone’s quiet hero. He’s mine.

How can our readers further follow your work online?

I write occasional non-fiction articles and business stories for my LinkedIn profile, my Medium account, and The Corporate Story blog at MadPipe. Fiction is still a puzzle box I’m trying to unlock, but I’m dead set on it.

Thank you so much for sharing these important insights. We wish you continued success and good health!



Pirie Jones Grossman
Authority Magazine

TedX Speaker, Influencer, Bestselling Author and former TV host for E! Entertainment Television, Fox Television, NBC, CBS and ABC.