1999 was the year Christmas and I broke up.
Category Archives: Startup Athlete
Years ago I read a study that said one of the most stated regrets of people on their deathbeds was that they hadn’t built a better relationship with their parents.
The oft repeated quote ‘no one on their deathbed wishes they spent more days at work’ has also been slyly directed my way more than once, enough that I might even start to listen. The other regret, however, weighs heavily on me.
I’ve watched with some concern as my parents get older. As a kid, time passes so slowly that you take everything for granted. Your parents have all the answers, I was sure my dad could beat up anyone else’s dad, and it just seemed like they’d both be around forever. Watching them age, even as gracefully as they have, has been a stark reminder that those regrets are rooted in a harsh reality.
I’ve had a front row seat as they both crafted entrepreneurial ventures from the ground up. They took big risks, worked hard, and eventually those ventures grew strong enough to pull us out of crippling debt. Some years later, they co-signed a loan to help me start my first restaurant.
The circle of debt continues…
My folks are the people I aspired to be. Self-made entrepreneurs who pulled themselves up by their own bootstraps, and still found a way to achieve their dreams, they were proof that you didn’t need charity, or luck, or a silver spoon. Coming from an Alberta farm, my dad’s solution to every problem was hard work, and my mother, fresh off the boat from Denmark, was always crafting, innovating, and thinking of new ways to approach old problems. Together they were a formidable pair, and watching them flip the bird to the corporate establishment and do it themselves felt like the greatest ‘fuck you’ to a world that I was just starting to realize wasn’t built to be fair.
A few years after they co-signed my first business loan, I had three busy restaurants, a social calendar filled with wine dinners, fashion galas, poker nights, wrap parties, and all the other bullshit I thought was cool at the time. I barely saw my folks in those days, I couldn’t manage to find the time to cross town and have dinner once a week, and was losing touch despite living a 30 minute drive away. It couldn’t have been any easier to stay in touch, and yet, I didn’t. I started to realize why those regrets would be on the lips of every person as they took stock of their existence. It was just so damn easy to take it for granted.
Forever isn’t forever, and time is a thief that distracts you, so that it can more easily steal your most precious moments.
I could see myself following in the footsteps of millions who came to regret their apathy, and I resolved to do something about it. Something drastic.
I moved into my parent’s basement.
It started off as awkwardly as you can imagine. The house was in a quiet suburb, populated by lousy chain restaurants, with nothing but raccoons and a long commute to keep you entertained. Restaurant life was hectic, social, and wildly unpredictable.
It seemed like I was walking away on a life that had enough booze and badly behaving people to stay interesting for quite some time.
After working for years to build the lifestyle I wanted, I had traded it in for the hope that I could avoid that single regret, the lingering wistfulness of memories that were never created, the opportunities forever lost. In retrospect, it was one of the best decisions I ever made.
Today is my father’s birthday. He is turning 74.
I’m broke, completely invested in a new business adventure, and I can’t afford to buy him a gift. I find myself quite humbled, and I’ve justified to myself that perhaps the better gift has been this time together.
It’s a lie, of course. That gift was a gift I gave myself, and keep re-gifting without guilt, year after year.
My father was my first mentor, my first business advisor, and the best sounding board I’ve ever had. He built Canada’s first microbreweries (Granville Island Brewery, Upper Canada Brewery) with a group of friends, starting one of the greatest movements the modern world has ever seen, craft beer. It was an impossible dream, an unlikely success, and was beset by obstacles, challenges, and an unproven market (there was beer, and light beer, brewed to taste ‘cold’…seriously, wtf does ‘cold’ taste like). That he did it at a time when our family was struggling with the fallout from the housing crash of ’82 is a constant reminder to me that our family is at its best when our backs are against the wall. I can still remember at 9 years old stuffing beer bottles into six pack containers to help out opening week, and getting my first hangover off batch #1 of GI lager (parenting was a little different back then).
My father’s father, Farley Sherwood, was rather persuasive about him getting a college education, so he came out west to earn a degree in forestry from UBC. He went back and landed a job on the radio, leveraged that fame to marry the local hotty, went on to sales (Imperial Oil), and eventually became the Marketing Manager for McDonald’s in Western Canada.
That was the job he quit when I was six, and to this day it remains a vivid memory. He checked out, mid way through a great career, in his prime. I remember him telling me and my brother that he was unhappy, his job wasn’t fulfilling, and he hated the politics. Confused, I struggled with the notion that your job was something you could enjoy, not just a paycheck. I was also more than a little concerned that we had just broken up with McDonalds. Even in the pre-nugget era that place had a grip on my heart, and I was pretty stoked to have happy meal connections. I was literally on a first name basis with the Hamburgler.
At six years old, I was served a reality check that indoctrinated me into the entrepreneurial ranks, and I had no idea.
We flirted with bankruptcy.
Actually, it was more of a long, drawn out affair. My folks had bought their dream house, and, counselled by their realtor into keeping the old one as long as possible to ride the rising market, they got caught in the crash. They owed twice as much as the houses were worth, and were getting crushed by 24% interest rates on two mortgages.
Just like that, happiness became a luxury we couldn’t afford.
We moved into the basement, and rented out the rest of the houses to help cover the mortgages, and Dad called a family meeting to craft a plan.
My brother and I got paper routes, lots of them. We stuffed flyers, mowed lawns, and did other odd jobs. My mother pulled a page out of the 3 Amigo’s script, and when asked what she could do to help, she said ‘I can sew’. Her little craft business grew into a sportswear business that grew into a national fashion company with an impressively innovative distribution model. It was the precursor to companies like Indochino, long before the digital age, and as my dad tells it, it was the rope that pulled us out of hell.
He was good at what he did, and he picked up gigs as a marketing consultant. Then, maybe because crazy plans were something he’d grown far more comfortable with, he and his friends came up with the idea to build a brewery, using the fresh Vancouver water, with all the heart and soul of being for locals, by locals. There were three large brewers at the time, and they paid the little upstart no mind. Within a year, however, they saw market share escaping, and combined forces to crush the microbrewery movement hard. It was too late, the market had gotten a taste, and soon small craft breweries were opening faster than Molson’s, Labbatt’s and O’Keefes could squash them. Unionizing plants, controlling bottle regulations, even excise and production limitations were successfully lobbied for, but microbreweries found a way to make it work, something that’s easier when you have customers clamoring for your product.
Happiness was a fish he had once tossed back into the water for being too small, and now he had hooked the big one.
My dad’s tolerance for risk had put him in deeper waters, and we almost drowned, but I’m convinced it was going through the struggles which gave him the hunger to appreciate every opportunity he had, and land that big fish when it counted. With my mom’s business thriving as well, they had pulled off the rare double, and there wasn’t a doubt left in my mind who my heroes were. The seed had been planted, my mind had been made, I saw the difficult path as the most attractive, with the biggest payoffs, and I was determined to be an entrepreneur just like them.
After 50, he started to look tired, and sometimes I wondered if he had grown a little weary of the world. He was supposed to be pushing retirement, and seemed to be genuinely considering it, even though there seemed to be lots more left in the tank. His signature glint in his eye didn’t appear so much, and I was wondering if it would ever return when the colleges came calling. That started a change.
I’d like to believe that being around young, idealistic students who still hold the notion that the world is theirs to change, was the reason he sparked up, and maybe it was just that he could stand in front of a room full of cute college girls and they’d believe every word he said (…and, I just realized I want to be a teacher), but he had a renewed energy, and the glint that had lived in his eyes for so many years was back, and brighter than ever.
He taught marketing and sales all the way up to 65, when they forced him into retirement. It was an outdated union rule that would end up being changed a couple of years too late, and I think he would have continued teaching to this day if they’d let him. The amount of his former students who still come up to me to tell me how much they learned from him, how important he was for them, and how much they loved his stories, is staggering.
I had one of them doing his best to vigorously convince me of how cool my dad is, and all I could do was nod, smile, and think, you don’t even know the half of it.
My dad’s retirement party was bittersweet. He didn’t want to celebrate it, as much as everyone wanted to celebrate him. He was getting pushed out, just when he was having the most fun. I remember thinking how odd it was, how broken the system, that its greatest contributors are removed when they’re at their most effective.
A man provides. He contributes.
We measure our worth by our ability to be the mind or muscle that moves mountains, even if it’s only a single stone at a time. We measure our lives by what we did, our contributions, and our impact. Take that away, and you take a fundamental part of our identity. We need purpose, and when we have it, we will build, we will act, we will overcome. When we don’t, we start losing our curiosity, our ambition, and our willingness to tackle anything but a ham sandwich and an afternoon nap.
When my dad retired, his signature spark, the glint in his eye, started to fade again. Without the regular influx of young idealism, boundless energy, and world changing ambition into his daily routine, I think he struggled to find a reason to give a shit. The chores around the house became the problems he needed to solve, and everyone knows that trimming the hedges doesn’t solve sweet fuck all.
I think often about carrying on the family name, of doing it justice.
My brother and I both have daughters, and that means the surname attached to our future generations won’t be his. I’m ok with it now. His surname has power to me because of who he is, who his father was, and all the fathers before him who worked their asses off to move the sticks a few yards further. They had different surnames, with different meanings to the sons and daughters who bore them on. The name represents those men, their sacrifices, their risks, their failures, and their successes, and while the name will change, their legacy will not, because of what they invested in their children, who invested it into my father, who has since invested it in me.
I’ve realized now, that as I was building my companies, my family, and my career, I thought I was creating a legacy. I wasn’t. I’ve inherited his. It has made me even more determined to measure up. I inherited a legacy from a long line of people who struggled and sacrificed to move the sticks a little further, and I’ll be damned if I’m the generation that fucks it all up.
The birth of my daughter was unexpected, and life changing. I’ve never been more scared of anything than when she first stopped breathing, seven weeks premature, and I was completely helpless to do anything about it. My parents were there for every minute, and without them I’d have been a complete wreck. (I was still a wreck, just with the support to ensure I could fake it appropriately)
From that moment on, my father’s choices in life made perfect sense. It wasn’t ambition, or pride, or even greed, which fueled his decision to chase happiness. He had learned the stakes of the game, that once you have seen how frail and impossible happiness is, how delicate and improbable its survival, you realize you need to fight for it. You need to put the bullshit on the line, the houses, the cars, the jobs and the fancy titles, and you need to put all that shit on red and spin the fucking wheel because the cost of having it far outweighs the cost of reaching for it.
I know my parents would like me to learn from their mistakes, I just can’t.
I ignored their mistakes, I forgot the times they yelled at me for fucking up (there were more than a few of those). I wrote over any memory of my father not being the man I wanted to grow up to be like. I saw every challenge he endured only through the successful outcome he wrestled from it.
It sounds naïve, but it isn’t. I studied everything he did that made him my hero, and tossed the rest. What do I need to know about mistakes he made? I know enough about pain and struggles, I’m a fucking connoisseur of the curveballs life can throw, and the only shot I’ve had of overcoming those is from studying someone with a demonstrated expertise in overcoming them.
I’m lucky, I know. Perspective is everything for me now.
I’m lucky that my parents would put up with my shit, give me a shot at avoiding this one regret, and teach me how to bait the hook and reel happiness in. Evangeline, our daughter, has inherited her Grandfather’s signature spark, and in turn, rekindled his, and they’ve formed a two person, cookie-snatching conspiracy.
I don’t know that this was the happiness that my father had in mind when he quit his job to start us on this adventure. I do know that on my deathbed, I will have one fewer regrets to list off before I pass on the torch to Evangeline.
Today is my dad’s birthday, and when I grow up, I want to be just like him.
Go post a dirty joke on his wall, he could use some new material. https://www.facebook.com/larry.sherwood.50
In my younger years, I owned a 1973 VW van. It was a sweet ride, slow as hell, but smooth, and the pull out bed in the back was perfect for lazy afternoons and hazy nights after hitting the bars. Because I thought I was some kind of badass, I had written on the back of this shit-box, ‘don’t laugh, your daughter might be in here’.
As is the requirement when you own such a vehicle, there are times when society (and your well persuasive and most likely criminal friends) requires that it be used as a hotbox. While it was foolish, I’m a slave to convention, weak willed, and like all stupid things it seemed like a great idea at the time. It’s also at that point that I learned how words lose their meaning once you’ve said them a few times.
Jumping into the startup scene is just like climbing into that van. It looks like a party on the outside, and everyone inside is smiling, but mostly they’re just repeating the same words over, and over, and over. Those words sound so cool when you say them the first time, and your mouth forms them slower, savouring the nuances and dissonant tonalities, and one smart asshat giggles to himself when he cracks ‘I just had a vowel movement’. By the end of the night, everyone is convinced that they’ve achieved enlightenment, but the reality is they’re just high, and everything sounds cool when you’re high.
Success is one of those words that gets passed around the startup bus. It’s not a word we were worried about in those days, clearly, but lately I’ve chewed on that word daily, draw it across my palate slowly, and spit it out to read the tea leaves. I have read about, dissected, and listened to every successful person as they describe success in ways most people can’t even consider. I have become a connoisseur, a success sommellier, my nose has become attuned to discover its signature where many can only taste bitter rejection, and I have experienced it in so many flavours that I have become a connoisseur.
I can’t help but feeling, however, that I had a better understanding of it back in that van. Ignorant, carefree, reckless, and directionless. Back then, I could reduce success to a moment. A goal scored, a paycheck cashed, third base with a pretty girl, these were tangible successes that produced immediate results.
I wanted to change the world like any 20 year old does, but it was so distant a possibility, so grand an ambition, that despite talk being cheap it was the only thing I could afford.
Now however, I have had my taste, and I want more. The genie is out of the bottle, I know we can change the world, the technology is in our hands, I have solved problems, built million dollar companies, and built a family. My tastes have grown more complex, though, and while every day I tell myself to be happy with that sunset, my beautiful family, my relatively good health, I can’t help but start looking for my next fix.
Once you believe anything is possible, how can you sit by and wait for someone else to do it?
Building Nickler has been humbling. I was prepared for the ‘it’s a marathon, not a sprint’ mentality, I was prepared for the crippling rejection from investors with little appetite for risk and even less vision for the future, I was even prepared for the mental stress of the debt I’ve racked up. What I wasn’t prepared for was being cut off from the steady drips of success through my veins.
Every project gives you little goosebumps along the way, keeping you in the game, motivated, pushing for the next little rush. Building the restaurant group, I rode those waves hard, 16 hour days of pure adrenaline, stress, and victory were easy to string together, and months went by like a blur.
Those are the times that you attract outstanding people to your cause, because awesome people look for other awesome people.
Nickler has been a grind. We started sprinting at the beginning, thinking that what we were building was a little app that would be quick to develop. Wireframes, workflows, logic, and integrations were dutifully planned out, three months turned to six, six turned to 9, and we soon realized we had created an entire platform. The genie grants wishes, but will always play his tricks, and I found myself reaching too far, a victim to my own ambition.
We had patted ourselves on the back for solving the problem on paper. We solved it elegantly, simply, and the market validation responses were rabid. All we had to do was build it, and building it with one developer has been like washing the Empire State Building with a toothbrush. There are no easy shortcuts to take, it either works completely or it’s useless. So we trudge on, and very soon, we’ll be ready for launch.
Success, that fickle tart, has been playing hard to get.
Persistence is one thing, but lately it feels like it’s flirting with insanity. I’ve had no choice but to diversify and get my fix elsewhere. It feels like cheating, but when you’ve got mouths to feed, a mortgage, and an entrepreneurial addiction, the justifications come easily.
Six months ago I started http://www.andersenwoodwork.com with a genius in the trade, Neil Andersen. We do cabinets, custom architectural millwork, and installations. Despite a slow start, today we’ve got two crews running and are on pace to hit $1m in sales this year. I’m damn proud of what Neil and I have built so early, and it speaks volumes about his reputation in that industry.
I filmed six episodes of a TV show called The Audience. I met some outstanding people, and we spent five straight days each episode solving other people’s problems.
I worked as a chef at a local daycare, for giggles, cooking for 45 toddlers, and realized we could streamline their culinary system while improving the quality of ingredients with only a few tweaks. I built a new business model for corporate that showed them how to increase quality and efficiency with only organic and local produce for less than they were currently spending.
I learned how to box, lost 25 lbs, and cracked a rib. I probably would’ve broken my jaw as well if the rib hadn’t gone first. The rush of battling pain, exhaustion, and big men who want to hurt me was the closest I’ve got so far to the fix I need. I find myself looking for scary guys to fight, I convince myself they’re packing heat to avoid fighting them.
Sometimes I convince myself of little lies to keep the illusion that I’m in control. I’m not. The biggest lie I tell myself is that I can do anything, be anything, and achieve my dreams. My dreams include private islands with submarine caverns, genetically engineering Unicorns, and becoming a martial arts expert.
For two years my plan was to build, launch, and grow Nickler into an outstanding success, and I’ve failed at that, so far. I had charted a path to success, and that path has felt like a complete shit show, a gong show, a complete goat rodeo. Lately I’ve been thinking I wouldn’t have had it any other way.
Success isn’t a thing. It’s not an achievement, a milestone, or an award.
Success is an idea, and the more you play with it, study it, and seek to understand it, the less it means. Stop studying success and go chase failure, you’ll learn far more and have way more fun.
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In boxing, everyone has a nickname. Cool ass nicknames like ‘the machine’, ‘lightning’, or ‘terminator’.
I’ve got a nickname. It’s not a cool nickname. It’s the kind of nickname you dread earning. It’s the kind that you earn in grade school and follows you forever. It’s a nickname I’ve earned, and nothing pisses me off more than that.
‘Take a knee’ Sherwood…
I readily admit, my penchant for taking a knee early on hasn’t earned me the respect of my coaches, peers, or frankly myself, but I’ve spent my whole life protecting myself from unreasonable physical harm, and it’s a tough habit to break. That coupled with the fact that I didn’t have the conditioning to last a full round, I didn’t have the defensive skill to avoid taking multiple heavy shots to the head, and I had the ill advised bravado to keep going in the ring with guys bigger, stronger and meaner than me.
Some problems are addressable, like conditioning, defense, and movement. Others, like a preference for diplomatic discussion as soon as I get punched in the face, are a bit more difficult to train away. That said, I spent the last two weeks dedicated to duct taping the gaping holes in my defense, doubled down on movement drills, and spent the off days on strength and conditioning training. Those were controllable issues that formed most of my excuses, the rest is just a question of mettle.
Monday’s training came, and two weeks of training had made me stronger, fitter, and far more defensive, so I called out coach Brian and went into the ring with the single goal of going the full round.
Brian is a solid, strong, and quick guy, but I’ve got 30 pounds on him. By rights, I should have an advantage, but he’s fast, skilled, and beats on guys like me for a living.
Like a surgeon, he picked apart my defense and threw quick, stinging shots anywhere and everywhere. I panicked, turtled, and covered any part of me I could. Immediately, I knew how this movie would end, and resigned myself to find a way to last it out. I was throwing jabs, and he was answering with quick combos, finding spots to nip, tuck, and tweak. I found myself tiring at that familiar place one minute in, I had blown it all again on punches that never pierced his guard, and had two minutes to turtle, catch my breath, and hopefully avoid the crusher.
But it didn’t end, I didn’t tire out, and I felt for the first time like I had the energy to mount a counter-attack. He was dancing around me, backing me into the ropes, and picking me apart. Like always, I felt like quitting, making the pain stop, and taking a knee, but the weeks of conditioning and the training kicked in, and my second wind arrived.
I threw a jab, then two, and the stinging stopped. My shoulders, usually weighted with fatigue, had strength, a bit of energy, and were more than a little pissed off. I threw another jab, and followed it with a right so filled with righteous anger it pushed through his flawless defense and landed. Adrenaline, sweet and pure, poured fuel on a fire that had finally turned to flame inside me, and I answered his barrage with a flurry of jab, hook, uppercut combos, pushing him against the ropes, wearing a turtle shell of his own. It was empowering, amazing, and a little frightening. For the first time in the ring, I was in control, I was the harbinger of justice, and justice was being served.
I was proud as hell, but spent. I wasn’t going to be able to keep up the torrid pace, and with a minute left I backed off to center ring, gave Brian a chance to recover, and waited for him to come to me. My defense had held up, I’d weathered the storm, but another one was coming, and this one had a purpose. Coach was intent on teaching a different kind of lesson, one that leaves a slightly deeper impression.
Speed is everything in boxing. Speed is power. Like a golf swing, the perfect punch seems effortless, and is honed to rote execution from years of dedicated practice. Jab, punch, hook. It’s a basic combination designed to break apart a defensive guard and set it up for a devastating hook at the end. Seasoned boxers do this combo in their sleep, rhythmically pounding it out on heavy bags day after day after day. It is so ingrained into their muscle memory that it escapes thought, avoids the microsecond delays of conscious thought, and becomes reflex itself.
Jab, punch, hook. I saw it coming, and knew it instantly. I had practiced this, I knew this, I could defend this. Every shot that had dropped me to this point had been to the head, and I locked that shit up like Fort Knox. Coolly, I nudged the jab aside, curved my glove against the incoming punch and deflected it upwards, with this economy of motion I ensured both hands were up and I was ready for the incoming hook. I was already planning my jab, jab, punch response when it came, low, and in the ribs, lifting me off the canvas with a yelp and into gravity’s familiar embrace.
The contact was unexpected, and quite an unsettling surprise, but more so was the sharp pain and shortness of breath from having my lungs collapsed. What was worse, though, was that I was there on one knee, on the canvas, begging for oxygen, humbled once again. I anticipated the head and he took the body. My normal fat based defense worn away by the weeks and months of training left my ribs without cushion for all 160 lbs of Brian to be concentrated into a single point of devastating impact, and it dropped me.
With 15 seconds left on the clock, time wound down, and another round where I had been measured, and found lacking, had passed.
A hard lesson learned, with a painful reminder. It’s clear that coach Brian knows how to make sure the curriculum sinks in.
I went home and iced it, popped some pills, and walked it off. Being humbled I’m used to, sports injuries are nothing new, and I was happy to see some progress, but to end up on my knee once again was demoralizing. I nursed my wounds in a hot bath with a cold beer, and I made a silent promise to myself that I would never stay down again. If they want to see me on my knees again, they’ll have to put me there.
But only if I don’t put them there first
Every morning I wake up to her. Sometimes she lies with me, quietly, and helps me ease into the day. Most times she is impatient, insistent. She won’t accept anything less than the complete enforcement of her presence upon me. She will not dictate my actions, but her presence alone spurs me forward, outward, into motion, away from her, but yet always within her embrace.
We didn’t meet by accident, or by design. One morning – our first – I awoke to her touch, and although unfamiliar, it wasn’t foreign, or frightening, and I found myself retracing the previous night’s adventures in an attempt remember the details of our little indiscretion.
She visited me often, never giving any indication she would stay, or any idea of when she might return. To say we felt love would be an exaggeration. We were intimate, she knowing far more about me than I her, but we weren’t beholden. I knew she had others, I knew some of them were better men than me, more deserving. I knew they had fought to earn her attention, while I had simply gone about my life, waiting for her to randomly show up, never really knowing what it was to love her, to need her, or to lose her.
As the years went by, my life got quiet, I settled down, I got comfortable. Fewer wild nights led to fewer nights together, until I rarely saw her at all. The few times she did show up, my resentment was so much that I rejected her, and soon she simply never returned. I began to erase all memory of her, and life became easy, comfortable even.
I never understood what her touch meant to me until years had passed, and I looked into the mirror to see an old, tired man staring back. The smile that had come so easily when I was younger now felt forced and awkward. The years of comfort had softened all my lines, and I no longer felt invincible. I was ashamed of this face that I wore, it had grown soft to hide the scars, and the eyes simply stared back. There was no fire, no spark. I had become a drone.
I knew full well that she had been the catalyst. She was the sum total of my failures, my weakness, and my humility. I had embraced her, accepted her, and made her mine, and in return she molded me into the man I wanted to become.
Age is a funny thing. At some point you realize and accept your mortality, the fearlessness that youthful ignorance infuses you with is finally challenged, and you need to make a choice, destiny or self-determination.
If you choose self-determination, you recognize that you are the sole arbiter of your fate, and thus you may take greater steps to protect yourself from an untimely end through unnecessary risks.
Destiny commands that you accept your fate, at whatever time and place it may come, and with that the freedom of mind to engage, with reckless abandon, this playground we’re given.
Instinctively we avoid her, but we forget that her opposite is numbness. She reminds us of our weakness, humbles us by how much our fragile bodies can endure, and forces us to recognize that we aren’t judged by our words, but by our actions.
I awoke every morning thereafter and felt her absence hanging in the room. Although I had gone so long without her, I hungered for her touch. Apathy had smothered me, jealously guarding me from a life filled with failures, skinned knees, and bruised egos. There was nothing left to do, but start moving.
I moved slowly at first, gasping as my lungs protested the cold November air. I pushed hard up the mountain trail, but the heaving and retching of my lungs was too much to continue, and defeated, I crawled home.
Every day I moved, eventually convincing my lungs to process enough oxygen to keep my doughy frame in flight. Each morning I awoke alone, the only witness to my solitude a pair of muddy runners, beckoning a return to their mountain playground.
Days passed, snow turned to rain, the mountain streams gave up their icicles for green mossy rocks, and my lungs filled with spring air, thick and heavy from fresh rain and damp earth. I ran further, my breath no longer holding me back, my legs finding rhythm, my mind finding silence, and the endorphins started trickling slowly through me. For a moment I forgot about the man who had hijacked my reflection, I forgot about being old, and I forgot about being tired.
I awoke the following day to find her, waiting. No words were spoken, no explanations needed. She simply lay with me as she had so often before. Whereas before I had only noted her presence, I now revelled in it, like the essence of life itself was rekindled, sparking and sputtering beneath my skin with her every touch. Tentatively, I turned to the trail-stained shoes to negotiate an off day, that I might lie with her longer, but the instinct was too strong, and in a moment I was in motion again. Her touch lingered with me the entire day like the memory of a lover’s perfume, every thought of it was exhilarating.
She arrived every morning after that, and every day just as the last I thought of breaking my stride to lie with her, exhale through the pillows and let the morning take me slowly into the day. Every day just as the last I awoke with her and went to the mountain.
Today, I know her like she knows me. She is my constant companion, she is my muse. She is the path to my best self, my greatest ambitions, and noblest pursuits. She is my pain, and she is my concubine.
Aprons for Gloves tryouts and a solid beating received. This guy looked about 6’6″, 230, and mean. The session starts with me doing 50? situps, one minute on a heavy bag, and then sprinting into the ring for an ass kicking.
I’d like to think he wailed on me because he figured I could bring some game, I threw everything i had on him, hooks, jabs, uppercuts. I danced, bobbed, and weaved, and for a total of 26 seconds it looked like the old man could still deliver the milk.
Something changed after those glorious seconds passed, and as I took a moment to catch my breath and think about how awesome a pugilist I was, the sky darkened.
In an instant, I was in a hailstorm of mitts, lost in a tornado of black gloves and hate. I tried to hold my ground, I locked eyes with my assailant, and all he returned was a grim smile. I could see that my weakness was like fried bacon on sunday morning for him, and he was coming in hungover and hungry.
I put up a wall (cowered in the corner) and the assault continued. The crowd, once cheering me on as I murdered a heavy bag, crushed crunches like Balboa, and swaggered around the ring like a caged tiger, suddenly turned. Cheers of encouragement quickly turned to concern, and one voice, as if by divine intervention, yelled ‘take a knee you’re getting killed’.
It seemed a simple strategy, but all the begging, cowering, and weeping had done little to stop the pain’icane, taking a knee seemed counter-intuitive. The good news is that I was most of the way there anyways, so when it dipped down, brushing the welcoming canvas every so lightly, the skies parted, the beating stopped, and I had a chance to catch my breath.
Then this guy starts counting to 10, and I won’t lie, I was a bit concerned that this meant there was more to come if I didn’t stay down.
I consider myself a logical man, to a fault, but as i was fumbling for the keys to my logic-mobile, I could see this behemoth of a man glowering at me with a cruel anticipation of all the harm he was going to inflict if I had the misfortune of lifting that knee. The keys slipped, I stood up on the 8 count, and I’m pretty sure I beckoned him over, determined to go out swinging.
He came at me fast, tossing aside any concept of mercy to an old, doughy, dreamer who didn’t have enough sense to stay down. In a moment, I formulated a plan that included a distance game, keeping him away with jabs, and staying mobile. It made sense in my head, as key scenes from Rocky’s 1 and 2 ran quickly through my mind.
The sky darkened again, the room went quiet, but not in awe. What little respect they may have had for a good effort had changed to confusion. There was no pity, just confusion. Why, oh why, would you do that…
My mind braced for the impact, I initiated the multi-faceted plan of movement and attack. I waited for limbs to move, legs to shuffle, head to bob, and quickly realized I had used it all. Every bit of oxygen, protein, sugar, and sheer will had been used. Scenes from Rocky were quickly replaced by scenes of Scotty in engineering screaming, “she’s given all she’s got, we’re sitting ducks out here! Brace for impact!”
I heard it before I felt it.
Time slowed, as if by some mercy to give me time to ponder my last moments, and seconds clicked by. I had no epiphanies, no sudden realization that I had wasted my life on trashy women and booze (those are investments, kind sir). Like a man walking the green mile, I had gone dead inside, transitioning into flesh and bone while my soul started the long journey elsewhere. I was no longer present, and I surrendered my flesh to the fates.
The sound was at first soft, and then as it bore into my consciousness it grew more grating, harsher, as if to worm its way into my mind and physically pull the conscious mind out of its panic room. I had never heard this noise before, it was a buzzer of sorts, but it didn’t belong here, in this cathedral of death and pain. It belonged somewhere sporting, like a gym, or ..oh shit here he comes.
He stopped right at my face, leaned way down, and whispered “you’re so damn lucky”.
Moments after I had made my peace with my fate, I was free. Free to suck in as much sweat stained air as I wanted, free to release my pillowy gloves from the protective detail around my face, free to finally pursue that relationship with the canvas floor. Coyly, I grabbed the ropes, held onto them with an iron grip, and whispered softly to the mat. ‘Our time will come, wait for me’.
I may have been bested, by a bigger, stronger, and more skilled man. A man whom I will forever have nightmares about, and always picture as the cruel overseer of whichever hell I land in, but I have tasted death, and I no longer fear it.
I will not back down, I will not give up, and I will not quit. I will stand or I will fall, but I will do so with every intention of emptying the tank on whoever stands in front of me.
I will get stronger.
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Why being broke is the best start-up strategy there is.
Startups are hard, but not because entrepreneurs don’t have an appetite for hard work. Rather, it’s the constant rejection, the inability to convince people of your glorious vision, and the ever present threat of failure that make pushing forward seem like reckless insanity. The secret to startup success is in embracing that insanity.
I look back to opening the first restaurant, at a time when I had no money, no network, a few close friends, and a cat named Monty, so named for his awkward resemblance to one Mr. Burns. He wouldn’t win any beauty contests, but he had the kind of human personality to make you think twice about the possibility of reincarnation. Opening day of the restaurant, after pulling a complete 30 hour work day to get it open, Monty got hit by a bus.
I got the call at the restaurant as I was doing the books trying to figure out how to manage the ridiculous amount of debt we had just put ourselves in. I was alone in an empty building, sitting in an empty kitchen, and felt like the last part of anything beautiful and hopeful had drained out of me for good.
I saw that memory as a tragedy, a sad time in my life, but recently I found my thoughts drifting, and the memory wafted into my mind for a moment with a different perspective. I remembered the terrible crushing sadness, and then the cold, clear certainty that followed. If there was a fate, destiny, or karma, it was trying to push me down, kick me in the junk and make me quit.
Obviously I did what any male in his 20’s would do, and promptly gave fate the finger and did my level best to make sure it couldn’t see me cry. Fuck fate, I’ll make this shit happen until it throws me in front of a bus, too.
We did, eventually, make it. It was hard work, and we were young enough to know everything, which meant we had no idea what we had to learn. The lessons came fast, and were unforgiving. Every single mistake cost us precious money, and they came like waves, so that just as we caught our breath, another was upon us. We were destined to drown, and saw it clearly. With no moves left, we just started trying to earn one customer at a time. It sounds simple, even cliché, but it forced us into a mentality that analyzed every single second of our customer’s experience, what went well, what needed to improve, and what they really wanted. Not surprisingly, it worked, and after three weeks we saw a huge increase in sales, most of our new customers had become regulars, and we hadn’t done a lick of advertising or promotion. Six months later we were playing to full houses, a great staff, and some of the best years of my life.
It taught me that my best work comes when I’m seriously fucked and out of options, and maybe I’ve been ignoring that lesson for too long.
Success does funny things to entrepreneurs. At some point they lose the ‘entrepreneur’ mentality and become businessmen and ‘managers’. Some of us get nervous, like we got lucky, and if we don’t fight like badgers to keep it, we’ll be right back in the kitchen crying over a dead cat. For me, each new venture required slightly more capital, was slightly more ambitious, and required hiring more and more staff to manage them. I was trying to build a fortress, as if the rolling tide of mistakes would keep crashing forever, and the only defense was bigger walls, more sales, more cash reserves, and more venues.
When I sold, I remember feeling that I had lost the spirit of who I was, and the spirit of what had created the success to begin with. I had become a manager, and it was a betrayal of the philosophies that had brought me this far. It was time to divest.
Starting Nickler was a perfect tonic, not only was it something I was driven to create from over a decade of hating paperwork, but it was in a completely new industry, technology and accounting. It was pretty clear I was about to get schooled like the new kid in gym class, but the deep end of the ocean was beckoning, and this time I was wearing water wings, and had developed a taste for brine.
The learning curve was just like the last time, except fate was kind enough to spare my cat.
I still had some bad habits, like hiring fast, pushing to product, and pitching before we were ready. I tried to raise investment like we did with the restaurants. This time, however, the investors weren’t impressed by a nice bottle of wine or a cute bartender, and selling them the dream got me kicked out of too many meetings to mention. I was sure the quickest path was the best path, and that meant raising enough money to hire a big team.
So I spent, and pitched, and hired, and pitched, and bitched, and pitched some more. I knew I needed to learn how to pitch better, and relished the opportunities to practice, but we were about to be out of money, fast, and I was running out of moves, and investors. Finally in February, I sat down with the team and we had ‘the talk’. March 1 was the end of the money, and it was up to Don (our CTO and my co-founder) and I to take it the last 10 yards. We stared deep into the abyss that day, and questioned every decision that had brought us here.
And then we jumped.
It was time to embrace the insanity. Don sold his car, dropped every expense but his phone, and moved in. I started looking for odd jobs to keep the coffee flowing and the internet on (thank you ayoudo.com!). Shit just got real.
The world changes when you have no goals left but to get yourself fed, survive, and make it until the next day. Your heart gets hard, but your mind gets focused. There isn’t any question of motivation, because the luxury of choice is removed. There is no think, only do.
Two weeks ago, after getting rejected by Ycombinator, we sat down and chose one of our beta customers. This will be our first customer to earn. We took apart the entire app and rebuilt it, piece by piece, in a painstaking process of perfecting what our users want from Nickler, and removing everything that didn’t make the workflow smoother, simpler, and relevant. It was gut wrenching to delete features we’d spent weeks building, but we need to eat, we need to continue, we need to earn the first one, so that we can move on to earn the next one.
I heard a quote from an old movie on Paul Gaugin, who, upon learning his neighbour who worked in government was also an aspiring opera singer, told him quite succinctly “you’ll never make it as an artist, because you don’t have to make it as an artist”. Basically, feed yourself with your craft, and you’ll soon learn whether you’ve got the stones for it.
I’ve never been happier with our company, its goals, and the vision of where we’re headed. I’ve lost ten pounds, I’m running every day, and can just barely hear the Rocky theme going on constant loop in the back of my mind. Our partnership has never been stronger, as we support, motivate, and challenge each other to get through another day.
Sure, I’m broke, but I’ve never felt more alive, more focused, and more determined to make this happen.
I’ve never felt more like an entrepreneur.