Building a Business - Vol. 1

I haven't published anything in a while, at least a few weeks now, even though I write 500 to 2,000+ words daily. Writing for public consumption has come to a halt for one reason: I am building a business, and it takes up almost all of my mind – not my time, but my mind, which is far worse, at least to me.

I don't write about my business for one reason – and one reason alone: it could fail. The idea of exposing my dreams and vulnerabilities is too much. But I regularly preach about the importance of getting out of your comfort zone. So, in the interest of not being a hypocrite, I'll go WAY outside of my comfort zone.

Here goes...

I've been working on this business for two decades. I was 24 years old when I came up with the idea. Back then, podcasts didn't exist, so there wasn't a place to listen to a million different "entrepreneurs" pontificate on this and that. And every other source of tech media was in its infancy, if it existed at all. In 20/20 hindsight, it was fertile ground for a real entrepreneur in that you had to build relationships – face to face. There just wasn't any other way to learn. And the word "entrepreneur" wasn't really in the nation's lexicon – thank God for that.

I didn't consider myself an entrepreneur. I just had a vision for a business – for a way of life, really. That's it. Nothing special. Outside of Tony Robbins, there wasn't a global community of "living your best life" bullshit, "side-hustles," and young people with all the answers. You simply had to figure everything out – and by everything – I mean every single thing.

I remember going to bookstores in a vain attempt to find "The Book." By that, I mean a book that spelled out how to build something from nothing. Guess what – it didn't exist. And it still doesn't. I sort of feel sorry for new business builders who are led to believe that these books not only exist but there are millions to choose from by "subject matter experts" with websites, social media, podcasts, Zoom classes, conferences, books, etc. And again, most of them are a few years removed from being able to legally consume alcohol.

I find it hard to understand how these "experts" have time to create media platforms in addition to building an actual business. It's almost as if (wink wink) they don't build businesses but create moronic media personalities. Lots of sizzle – no steak.

Anyway, I've been busy building my business. Like anyone else who's embarked on creating something out of nothing, it's an All-encompassing endeavor. My brain never stops thinking about it. I dream about it. Truly, I do. It NEVER ends.

It's why I go for long walks several times a week. I've been a "walker" my entire life, but for the last few decades, walking has been my source of equanimity. I cannot live without it. I must be in the woods, alone. I have a five-mile walk that is mine. I don't own the land on which it sits (the county does), but it's mine. Maybe when I'm walking, the aforementioned media tycoons are creating "content."

I have a few things that I do to ensure I get the most out of my walks:

1st – I try to shower before I walk. It's not always possible, but I strive for it because it adds an element of formality – it sets the tone.

2nd – I wear the same thing: in the summer it's a pair of Patagonia running shorts and a white cotton t-shirt, and in the winter it's sweatpants and a hooded sweatshirt from my squash club in Boston. I always walk in New Balance 990s and an '89 Walker Cup hat from Peachtree Golf Club in Atlanta.

3rd – I make sure I am hydrated, and I never walk after eating. Walking on a full stomach is a distraction, as is being thirsty. I also don't carry a bottle of water – that's distracting too.

4th – I bring a three-inch golf pencil and a single sheet of 5x7 paper to write down ideas. 90% of every idea I've had over the last twenty-five years came to me on a walk.

5th – I prefer to walk while the sun is setting.

In a perfect world, every walk would look like this:

Time of the year: September, October, November. I prefer cool autumn weather.

Color of Leaves: The following Crayola colors (feels like I'm in a Wes Anderson film):

  • Scarlet

  • Burnt Orange

  • Mango Tango

  • Dandelion

  • Asparagus

  • Fuzzy Wuzzy

Time of Day: 30 minutes before sunset through civil twilight. I love seeing the sun slice through barren trees.

Lastly, and most importantly, I never bring my phone. In fact, when I see idiots talking on their phones, it takes everything inside of me not to say something. The woods are a place of respite. If I were President, I'd pass an executive order forbidding the use of technology in the woods. I just don't understand these idiots. When 99% of the people around you have intentionally not brought their phones and you find it acceptable to do the opposite, well, let's hope these idiots don't procreate. The world needs fewer of them.

I usually do five miles at a clip. Two and a half in, two and a half out. And it's almost always around mile marker two that my mind transcends into peace. It takes about 4,000 steps to turn my brain off (the average person takes 2,100 steps in a mile, but I have long legs, so mine is shorter). At two miles I have clarity, and it's at this time when I avoid human beings at all costs. If a gaggle of retirees, teenagers, or the aforementioned idiots are within earshot, I let them pass. This is when the trail becomes mine. I know I have 6,000 more steps to dream, to think deeply, and to enjoy nature.

That said, there are times when I approach 4,000 steps and I know I need more time. If I'm chewing on a big idea, I don't turn around at two and a half miles. I keep walking and turn my walk into a ten-miler. I especially love these walks, though I don't often need them. The only downside to doubling down is bruised toenails and an aching back. But most of the time, five miles works fine.

I've been on a lot of walks lately. Building this business is (I can't believe I'm saying this) no walk in the park. Horrible – I know. I'm too lazy to find another analogy. But it's hard damn work. So hard, in fact, that two months ago I came to the conclusion that I was out of ideas. The well was empty. I had no energy for it. I thought about quitting, but like always, I didn't. Sometimes I wish I was a quitter. I really do – I'm not just saying that. Life would be so much easier if I'd quit sometimes.

In lieu of quitting, I gave myself a 90-day reprieve. Since nothing was happening anyway, I figured I'd give it until year-end to see if I'd find a new source of inspiration, energy, anything at all. Only those who have built companies know what I'm talking about. There comes a time when you are done – totally spent. You've been running on fumes for too long. And no matter how much harder you work, you get the feeling that the universe is telling you to stop. If you're young, you keep going because you can, but if you're approaching middle age or older, you eventually realize this is non-negotiable. You accept your limitations.

Somewhere between late 20s and middle age, at the precious age when I was still too dumb to know I couldn't do it all, but I sort of saw the writing on the wall, I pushed it – again, and again, and again. I don't know if I'd call what happened a nervous breakdown, only because I don't know the official definition, but I hit the wall – and I hit the wall HARD.

It was so hard that it scared the hell out of me. I knew what physical exhaustion felt like on account of doing a triathlon and completing a half-marathon, but those paled in comparison. A complete mental exhaustion is a thousand times worse. And it happened twice. I didn't learn much the first time, so, like a jackass, I doubled down, but the consequences weren't twice as bad – they were twenty times as bad. The universe 10x'd it – and it was BRUTAL.

These are the things that "entrepreneurs" rarely talk about on social media. The terrible sacrifices that no one wants to hear. After all, if I'm selling the dream – you know what I'm talking about: not having a boss, unlimited income potential (operative word being potential), and all the other bullshit, your average 20 or 30-something isn't going to tell the truth, but not necessarily because he's dishonest, but because he hasn't experienced it yet. The fact is he hasn't lived long enough. And he's not stupid – he knows no one will buy what he's selling if it came with the equivalent of a Surgeon General's warning: This lifestyle will cause mental, physical, and financial ruin.

Bottom line is this: building a company isn't what it's cracked up to be – ask anyone over the age of 40 if you need proof. But let's add another layer to it – one that NO ONE discusses: and that is the contingent of "entrepreneurs" who have a safety net that looks a lot like daddy.

Allow me to let you in on a secret: a lot of "entrepreneurs" didn't bootstrap it. Not by a LONG shot. A lot of these clowns were born on third base, believing they hit a triple. I'll explain how this phenomenon works: a young buck, usually educated in a private school K-12, goes on to college, gets a degree (usually in the humanities), and starts a company in his mid to late 20s. As his business starts to take off, he has a remarkable ability to weather storms that knock out 99% of other people doing the same thing. But junior does it, and everyone is impressed – least of which is junior himself, because, after all, he "did it." He managed to stay in business for years on end, but there's something that everyone eventually starts to wonder: how does junior pay his rent? Or, as the case is more often than not, how does he pay his mortgage? And how does he afford ski trips to Telluride and weekends in Napa? And wasn't it odd that he got his pilot's license? As the years go by, this line of questioning extends to, "How did he afford his country club membership?" Before you know it, junior's life starts to resemble his father's life, but his business hasn't cash flowed.

Anyone with a brain knows good and well that he's being fed with the same silver spoon that his nanny used to play airplane with, but these days it's his father's accountant wiring "loans." After all, he was going to get the money anyway, so might as well front-load his inheritance into his "business." This is a win-win in that daddy can brag about his offspring while junior "bootstraps" his dream. This happens more often than you may think, and it happens quite frequently in certain zip codes: 30327 in Atlanta, 02115 in Boston, 94027 in San Francisco. But why pop his bubble? Junior believes in his work ethic, despite his single-digit handicap and three martini lunches. If you don't believe him, just ask his friends who "run" similar "companies."

Now, in the interest of full disclosure, I have had some major advantages in life. My parents didn't bankroll my business, but they certainly helped in many ways. For starters, they've been married for fifty years; having a stable family who loves you is a HUGE advantage in life. My parents also made sure I had the best education possible. I went to the best public schools and my parents put me through college. Put another way, I was always in advantageous places and around people who encouraged me to succeed. Environment plays a massive role in life.

Growing up middle class in post-WWII to pre-9/11 America may have been the single greatest years for a human being to be alive. America was thriving on unprecedented levels and the middle class flourished. I was born in 1979 and graduated high school in 1997 – talk about luck. Add to that, I'm male, white, over six feet tall, and I'm athletic enough not to embarrass myself in any sport. I hit the genetic lottery, and I know it (so does Warren Buffett). So, while I'm not above throwing entitled rich kids under the bus, I do realize I was born into a fortunate set of circumstances.

But that doesn't mean building this business of mine came easy. And I'm not "there" yet. This whole thing could still fall apart. And if it does, the last thing I want are articles about it, but, as I said earlier, I need to practice what I preach. So, I'm penning this piece with the hope that the good Lord will see fit to my succeeding. I have failed so much that I forgot what success felt like. But that's par for course as a builder. As hard as it has been, there is an indescribable feeling to being a creator. To dream something up and see it come to fruition is one of life's greatest experiences. Like everything else, it's slow to build – like watching a model airplane being put together. The highs are extremely high, and the lows are terribly low. The mind games... they're cruel and usually self-inflicted. Some days I feel like I've mastered the art of kicking myself in the balls.

Like a sailor in a storm, you have to constantly reset your rhumb line. When a storm knocks you off course, you have to immediately address your whereabouts and get back to sailing in the right direction. It's hard damn work and it never gets easier, but the mind does get wiser. I have this prayer I do every morning: first, I pray that my will is aligned with God's. I have a track record of keeping my ship lost at sea with bad decisions and an ego run riot. My only hope is aligning myself with my higher power. Second, I pray for the patience of knowing today will probably be just like every other day in that nothing exciting or life-changing is going to happen. Life is mostly a string of boring days stacked on top of one another – and that's OK. And lastly, I pray for acceptance – to accept at least one thing is going to happen today that I don't like, and my response to it will determine how the rest of my day goes. So, as a mentor has always said, "You can react with character defects, or respond with character qualities." As long as I do all three, I know I'm going to be just fine and that everything will work out in accordance with His will (again, I trust the will of God over mine).

But there is one more thing. Something that I was recently introduced to that made a HUGE difference in the quality of my life – chew on this: if you knew that everything would work out perfectly in one year, how would you live for the next year? Think about that for a moment. My first response was to work harder – until I realized there couldn't be a worse answer.

The best answer is to slow down, breathe, relax, and be grateful. And that's how I live these days. Everything will work out the way it's supposed to, and I can't really do a thing about it. I have little control over anything outside of my attitude and who I spend my time with. Other than that, it's foolish to believe you control anything. So, I tend to sit back and relax more these days.

I'm still aiming at a moving target. I'd like to believe everything will work out, but I'm human, which means I'm plagued with insecurities and the ghosts of Christmas Past. I've been in the race long enough to recognize momentum and when things appear to be genuinely coming together, and that's what it feels like, but damned if those ghosts don't live rent-free in my head.

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The Executive Workout

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Where I Am