Curious children in Nepal.

The Making of a Money Mindset (Part 2): Early Experiences in the “Real World”

This is part 2 in The Making of a Money Mindset series. If you haven’t already, I’d recommend reading Part 1 first which sets a direction for where this rambling reflection might (eventually) take us and explores some of the early experiences in my life that influenced the way I think about money. You can read it here: Part 1: Learning the Value of Money. 


During my summer breaks in college my parents required I cover my living expenses. This had prompted my first work experiences out in the “real world.”

Crossing a suspension bridge in Nepal.
Crossing a suspension bridge in Nepal.

I got my first job after completing my freshman year. I had moved back home for the summer and was trying to convince someone (anyone) to hire me. The only company I persuaded to interview me was Home Depot and that had gone swiftly downhill after my interviewer learned I hadn’t brought a pen with me to fill out her forms.

Mercifully, or at least I thought at the time, my girlfriend’s father pulled some strings and got me a job with a construction company. I arrived at the interview with a pen. There was no real interview, all they asked was when I could start. I had no experience to speak of—nothing to fodder up a resume with—but they were willing to pay me a whole $2 above minimum wage. It was my first lesson in that true and timeless cliche: finding work often has more to do with who you know than what you know. I hadn’t known much, but I probably should have known that my 18 year-old girlfriend’s father had never been all that enthusiastic on me dating his firstborn.

I was promptly assigned to a commercial painting outfit as a “prepper.” I’d start next Monday. On my first day of work I was given a commercial tape dispenser and a heavy, 40’ extendable ladder I could barely lift. My job was to—as fast as possible—cover up the windows, gutters and wood trim on the outside of three-story apartment complexes before they were painted.

The work was relentless and physically brutal. As preppers we were always racing to stay ahead of our boss and the roar of his motorized spray gun, which guzzled up buckets of paint and belched them out onto the apartment walls with inhuman speed. The first time I leaned off the ladder to reach a third story window I looked down and began shaking in terror. Was this what was meant by the phrase a breakneck pace?1

Besides a laughable 10 minute break in the morning and a 40 minute lunch, the only time I had to myself were the few, precious minutes I stole away while walking to the porta-potty. California experienced a record-breaking heat wave that summer. I commonly burned myself climbing onto scorching roof tiles, which baked in the sun like pizzas in a clay oven. Heat waves bounced off everything.

I doubt anyone at work expected I’d last very long. I was one of the youngest in our squad and someone quit every week. One time, a young, Mexican man a few years older than me asked if I’d like to go to a movie with him on the weekend. I thought I was finally making a friend. I wasn’t. He was joking and insinuating that I was gay in front of our coworkers—something I suspected wasn’t widely tolerated here. There were no women. Lunchtime conversation topics were lewd and disturbing—even for a freshman college student. I usually ate lunch alone in my car in the shade, counting down the minutes before I’d hear the manic sound of the paint gun’s motor whirr up again, calling me back to my ladder.

Work started at dawn. Every afternoon was the same: I’d make the 40 minute commute home while anticipating the fast-approaching climax of my day. When I arrived home I’d limp to the fridge, grab a cold beer and collapse, comatose on the living room couch for hours. Just like the minutes at lunch, the hours marched on indifferently, always dragging me back to that ladder. That awful ladder. My life orbited around a runged piece of extendable aluminum. How, I wondered, do people live like this?

Sunset over Varanasi
Varanasi, India.

After the faux movie invitation, I occasionally still risked conversation with my coworkers. I learned that one kid, around my age (19), unwound every evening by drinking a 40oz of malt liquor and smoking a bowl of marijuana. He often smoked before work too. I shuddered at the thought of his future. Another man, old enough to be my father and who I suspected was illegally in the country,2 told me that he worked a second full-time job delivering pizzas at night to support his family living in Mexico. I was shellshocked. How was that even possible? I returned to my work, awed and appalled by his martyrdom.

To Mom’s relief and everyone’s astonishment I survived the summer. Fall’s swift arrival felt like an alarm clock jolting me out of a bad dream on a school day. It had just been a dream. That wasn’t my actual life. I was grateful to be going back to college.

On my last day my coworkers sent me off with a standing ovation. Dad told me he was proud of me. In commemoration, Mom framed a 2″x2″ patch of my paint-covered work jeans, which, to this day, sits on the upper shelf of a bookcase in my former room, the only remaining relic from that terrible summer. It’s presence a haunting reminder that it had not been just a dream.


The following summer I took a maintenance job on campus. A close friend of mine who had already been hired put in a good word for me. The interview was a joke—I got the job by my ability to show up for it. I would be maintaining the university’s outdoor amphitheater and its professional-size sports stadium which was home to our nationally ranked, D1 men’s basketball program.

The university had required that the maintenance company hire a certain quota of students. As a result the company hired more students than they actually needed, some who didn’t know a hammer from a screwdriver. Not only knowing the difference but how to use both, my friend and I quickly distinguished ourselves as both reliable and competent.

Whenever one of our three supervisors needed us we’d get a call on the radio we were required to carry. Otherwise our main job was explicit: don’t get caught doing nothing by the executives. Once we had learned the ropes of this cat and mouse game, we’d quietly clock in, turn our radios on and disappear into the ether, silently haunting the many nooks and crannies of the stadium. I began arriving at work expecting to have at least a few hours to take a nap or finish a stack of school work. Eventually it got to the point where I would take a swim in the pool at my apartment complex or go work out in the school gym while on the clock.

Trucker in Nepal takes a nap
A trucker takes a nap in Kathmandu, Nepal.

Our three immediate supervisors were all playing the same game—often better than we were. We would all clock each other in and out of the electronic time-keeping system when someone wanted to take a late morning or an early afternoon on the company’s dime—which was most of the time. As long as we remained loyal to their radio calls and kept them out of trouble they rarely cared what we were up to. I do vaguely remember being reprimanded when word got around that instead of watering the plants in the outdoor amphitheater I had been sunbathing directly beneath our university president’s office window. But a wink and a suggestion to be a bit more discreet was all it ever amounted to.

What made it a dream job though was that the arena doubled as a concert venue for big name bands like Tool, The Foo Fighters and Marilyn Manson. I’d sign up for the night shifts loading and unloading the band’s gear before and after the show.3 Not only was the pay better, but I had backstage access to any show that toured our campus. One time when we were shorthanded I got to climb up into the rafters and operate the spotlight.

It took a while for me to start wondering if maybe I should dream a little bigger. None of my supervisors seemed particularly happy or healthy. One was an alcoholic, another was cheating on his wife again (even though she had threatened to leave him if he was caught having another affair) and the third had been court ordered out of the Hell’s Angels and was struggling with depression and going through his third divorce. My supervisors managed not to do much on company time but wasn’t it still their time they were wasting? We all had to punch our names into the same clock every morning.

I had spent most my time on the job figuring out ways not to work instead of how I might make my work meaningful. I was good at it, but the consequences of this strategy were beginning to show. I felt uneasy by my delight in stealing company time. Might it be coming at the expense of my integrity and self-respect? I noticed a growing sense of apathy and entitlement within myself. Left unchecked, I feared it might bleed into other areas of my life. Maybe it had already. I continued working at the sports arena until my senior year, by which time my scheduled hours had all but withered away and I was let go due to budget cuts.


It was around this time that I buttoned up my collar and took my first steps into my chosen field of study: finance. I had lined up an interview with a downtown hedge fund through my school’s finance and investment society. The internship was unpaid but it was a way, I figured, to get my foot in the door. For the interview I wore a shabby pair of slacks, an ill-fitting blazer and a dusty pair of dress shoes that I used primarily for schmoozing it up at sorority dances. During the interview, Donovan, the hedge fund manager, asked me what I knew about finance and investing. I nervously told him I knew nothing about finance investing. That was why I wanted the job. I got the internship.

Donovan’s lifestyle was eccentric to say the least. I and a handful of other interns would meet with him once a week in his office downtown. His office turned out to be a computer desk in the loft of his condo looking out over his living room. On the far side was a wall of windows that climbed up to meet a raised ceiling. Rays of light, no doubt pleased to end their cosmic journey in such a place, beamed down from the sky, illuminating the spacious room’s soft, pastel color scheme. Beyond the patio outside I could see the shimmering, deep blue of the San Diego bay. Off to the right side, near the bedroom, I noticed an old school Coca-Cola vending machine with a button for Pabst Blue Ribbon Beer. I wondered if it would really work. Of course it would.

One time I showed up for a meeting before Donovan had arrived. When I called to let him know I was there he asked me to meet him in the underground parking lot. He pulled up in a red Ferrari, stepped out of the car and rolled over to me on a pair of Heelies. (A shoe with wheels built into the heel allowing you to skate on them. They were in vogue for about two seconds.) Another time Donovan invited me to join him on a Friday night at his VIP table in one of San Diego’s premiere downtown nightclubs to see the superstar deejay Armin van Buuren. I declined because I was underage and couldn’t figure out how I’d get past the bouncer at the front door. Donovan seemed to be the finance world’s equivalent of a rockstar. He was living life on his terms. I was captivated.

Trekking in Khumbu, Nepal.
Trekking in Khumbu, Nepal.

Donovan’s lifestyle wasn’t the only thing that intrigued me about him. One time an intern showed up late to one of our meetings. Donovan roasted him in front of everyone and sent him home with the instruction not to come back unless he was on time.4 I always arrived for meetings plenty early after that. Unlike my supervisors at the sports arena, Donovan put a high value on time. He had no tolerance for people who wasted it.

It also quickly became obvious that he didn’t need any of the interns he had gone through all the trouble of hiring. He would send us off with reading and analytical assignments but we weren’t doing any real work for the fund. In fact, I wasn’t at all sure he needed the fund either—much of the profits were going to charity. What was he doing all this for?

Each week we’d sit around a table and discuss concepts and strategy. I was often intensely uncomfortable in these meetings (besides Pedram, a nerdy, extremely well-manicured kid who dressed and talked as if he’d already spent years on Wall Street, I suspect everyone was). Letting Donovan’s easygoing demeanor coax you off your guard was a mistake you weren’t likely to repeat. He was a formidable thinker and prone to put you on the spot.

He didn’t care for the rote facts and formulas that would get you off the hook with most my business professors—he had someone called Linda for that. (I later learned Linda was actually a something: an incredibly powerful and expensive piece of trading software.) He didn’t want to hear the answer, he wanted to hear my answer. How would we think about that? How about this? He seemed to be teaching us how to think for no apparent reason other than because he wanted to, and probably, I suspected, because it had worked for him.

Signpost in the Carpathian Mountains, Romania
Signpost in the Carpathian Mountains, Romania

To my credit, I realized Donovan’s interest in how I thought was at least as extraordinary as his lifestyle. After the internship ended I asked him if he’d meet me for lunch to talk about my career. He did. He’s remained a friend I can call on ever since. I had unwittingly found my first mentor.


In my senior year I took a paid internship with a consulting firm advising Fortune 500 companies on business strategy. It had come to me through my 400 level business management class. The class had been a lot like Donovan’s internship: open-ended and stimulating with a focus on how to think rather than what to think. My professor seemed cast out of iron—a true titan of the business world. She was an entrepreneur, a partner at the consulting firm that would later hire me, and was married to a corporate CEO. She had a razor sharp wit, a fierce focus and a confrontational manner that inspired alarm amongst even the most well-studied of her students. She could lock on and dismantle the most well-constructed egos within seconds of discovering their trespassing presence. She took no bullshit. I imagined she probably spent a few past lives as a shark.

She intimidated the hell out of me but she also engaged me. I silently shouldered the snide nicknames she dubbed for my friend and I (Tweedle Dee & Tweedle Dum and Beavis and Butthead, among others) and became a regular at her office hours after class. I did all the reading and agonized over our final group presentation, which didn’t prevent us from bombing it terrifically, being saved from utter annihilation in the Q&A period that followed by the end-of-class bell. I earned the top grade in her class anyhow, which was an A-. No one earned an A.

Near the end of the class she set me up with an interview at her consulting firm. It felt like a big time opportunity. I drove out to the firm’s offices in the posh La Jolla business district up the coast. I rode the elevator to the 7th floor and took a seat in an executive-style leather chair in one of the firm’s glass-panelled conference rooms that overlooked the parking lot I had pulled up in below. I had parked a ways off in hopes no one would see the 10 year-old station station wagon I arrived in. I was interviewed by an analyst who asked me to calculate, on the spot, how many people were playing volleyball right this moment in North America. It would be one of the last times anyone at the firm took an interest in what or how I thought.

As interns our primary job was to perform espionage on our client’s competitors and churn out powerpoint presentations called “deliverables.” There was an enormous pressure to serve up proprietary data for our clients. If I couldn’t find the data we needed online I picked up the phone and called our client’s competitors directly—often under the pretense of a student doing a research project, a confused customer or potential job applicant. In other words, I lied. I don’t remember if I was explicitly taught to do this or if I absorbed it through osmosis. Ethics was never discussed. This was less an act of omission by the firm than it was a complete failure to provide any training at all. It was sink or swim. I picked up the phone.

If I had brought a canary into that office it would have died within hours. Like our deliverables, everything else at the firm seemed enshrouded in secrecy—I never had more than a murky sense of how the company actually operated. People always seemed strung up and tense. I was usually one of them. My office was down a long hallway lined on both sides with closed doors and drawn shades that concealed everything but the faint sound of muffled voices as I walked by. Rumors roamed more freely among the offices than their occupants. Was he fired? Who slept under his desk last weekend? Is she the one really calling the shots? Are we on the edge of bankruptcy without that client?

WW2 Bunker
WW2 bunker on the border of Czech Republic and Poland.

Fear was my major motivator. Attention from the higher ups was dubious and cause for concern. I did my best to do what I was told and keep a low profile. When the internship ended I wasn’t invited to join the firm full-time.

Despite having an office only a few doors down, my professor became exceedingly distant with me over the course of my internship. Had I had fallen out of favor? Failed some unknown test? If I had I didn’t know why or what to do about it. She never gave me any feedback. Occasionally her office door would be cracked open and I’d steal a glimpse of her, hunched over her computer screen, as I walked down the hall. Those are the images I remember of her now.

After the internship ended she dropped out of my life completely. I made several attempts to keep in touch over the years but she never responded to any of my emails.5 At the end of her class I asked her for a letter of recommendation which she did indeed write for me. It was a page and a half long. I felt vindicated. When I gave it to my future employer he commented that the letter had mostly talked about her.

I never felt good enough around my professor. For a while at least, it motivated me to try and prove myself to her. Maybe the same feeling was motivating her too.

Graffiti in Tbilisi
Graffiti in Tbilisi , Georgia.

I took one last job before I graduated. It was with a company with a cryptic name that could have meant anything. The interview took place in a cramped office tucked away in a colorless industrial park on the south side of the city. I arrived to find a long line of interviewees ahead of me. I was handed a form to fill out and waited for my name to be called. The interview went well but after I still had no clue what the company actually did. It was 2009. The stock market had crashed and the entire country was struggling to breathe under the weight of the economic recession that followed. My dad was laid off, again. I was months away from graduation. I couldn’t stay in San Diego without a job. So when the company called back and offered me one, I took it. No questions asked.

On my first day I was given a red polo to put on. I would be shadowing a senior employee “out in the field.” What the company called “the field” most people would call a gas station. My job was to sell cheap and fast windshield repairs to drivers with chipped windshields as they stopped to fill up their gas tanks. They weren’t really that cheap but most driver’s insurance plans covered them which meant they paid very little out of pocket. That was pretty much our pitch. They were fast though as all we did was a smear a little bit of clear, liquid resin over the chipped surface. They weren’t actually our products either. Our company received a commission from the manufacturer for each unit sold, which they then split 50/50 with the salesmen who sold it. I’m pretty sure the company also paid the gas stations under the table for the privilege of having us stand outside and hassle their customers into insurance scams.

My mentor was a bright and ambitious woman a couple years older than I was. If she kept up her numbers and produced enough successful trainees beneath her, she told me, she’d be running her own office with the company in a year or two. Opening up an office was every new recruit’s goal. She had the numbers all worked out. She knew how much she was going to make and what it would take to get there. I was impressed by her clarity.

She approached prospects at the pump fearlessly. It was a numbers game, she told me during a lull. If 99% of the time the answer was no then we just needed to ask 100 times. Simple as that. I didn’t suggest that if those were the odds maybe we should be asking a different question. She seemed completely insulated from the constant, awkward pain of rejection by an impenetrable armor of positivity and ambition. I had no such armor. By the end of my first day on the hot, oily asphalt of “the field” I had sold one window repair for a total commission of $10. It was humiliating.

There was one other coworker on our team and she had also made only one sale that day. I remember her being overweight and incredibly pessimistic. She barely made any effort to sell the product, content to sit around and smoke cigarettes most the time. My group leader told me she had been with the company for a few months now but was struggling to hit her numbers. I couldn’t understand why she was still here. After our first couple weeks of training our compensation was based entirely on our sales commissions. Didn’t she have something better to do?

On the morning of the second day I was required to attend an early, all-staff sales meeting before heading back out into “the field.” Around 20 sales agents packed into a small room in the back of the main office. There was whiteboard on one wall. We formed a semicircle facing our lead supervisor who ran the office. She didn’t go out in “the field” anymore. She was attractive, blonde and charismatic. I guessed she was probably in her mid twenties. She started in on a long motivational speech peppered with sales strategies (it’s a numbers game), past success stories that had become the stuff of company lore and legend and stories from her own meteoric rise within the company. People started to fidget. The room got warmer.

She introduced the acronym “JUICE!”—what it had stood for I no longer recall but everyone there knew it. People began enthusiastically belting it back in response to our supervisor’s preaching which was now in full swing. Then she brought it home: we were in the right place if we wanted to work for ourselves, if we wanted to take control of our lives. With the right attitude and determination we too could climb up into the upper echelons of the company and make fistfuls of cash like her. People jostled around excitedly; the room now hot. I looked around. The ratio of field workers to supervisors was 20 to 1—didn’t anyone else notice this?

Sheep on a desert road in Armenia.
Sheep on a desert road in Armenia.

Then it got truly weird. With promises of financial freedom aplenty, our leader whipped the room into a frenzy. People were jumping, cheering, and clapping. The pungent smell of sweat reached my nostrils. We formed a circle around our all-knowing leader and one by one, she announced—as if they were entering the ring for the big fight—each person’s name along with their recent sales numbers. In her best announcer voice, each person was introduced as “juicy!”, sometimes being “theeeee juiciest!” or “his juicinesssss!” Then there would be a fresh round of ruckus-making and the person announced would run around the perimeter as if it were a game of duck duck goose, high-fiving each person along the way while everyone chanted loudly in unison: “JUICE! JUICE! JUICE!”

My turn for juicy glory arrived. I meekly jogged around the circle and collected my high-fives. Then we headed out “into the field.” The motivational pep talk didn’t take hold; I ended the day with one sale. I handed my red polo in at the office and told them I wasn’t coming back. It was the first time I ever quit a job. I never received a check for the two sales I made.


While cutting my teeth out in the “real world” I also cofounded a business back on my college campus. I sold marijuana. A friend and I had been outraged by the low quality and high prices in San Diego. Why not do something about it? It was a radical question. We pooled our money together, bought two ounces of good marijuana and told our friends to come by if they wanted some. Before long our friends told their friends and we were in business. Soon we realized we could solve other equally common problems in the black market. We were friendly, trustworthy and white. We lived close to campus. One of us was almost always available to meet the same day. Business boomed.

After college we shut down our small, clandestine operation for good. The business may not have been legitimate but the lessons learned were. Instead of just studying how successful businesses worked I had run my own. The business principles that had been too dense and abstract to interest me in my classes were now immediately relevant and applying them paid off. This was why people learned this stuff. Developing a referral marketing policy was requiring our clients to be friends of friends. Managing cash flow was making sure we saved enough money to buy more product. Keeping our clients coming back was sales and customer service. Making sure our product stayed fresh was inventory management and required good supplier relations.

It never felt like a job. I enjoyed the work and set my own schedule. I made enough money to do the things I wanted and I had the time to do them. It was a throwback to those hot summer days I spent as a kid washing cars. I was working for myself again. I seemed to have a knack for it.

But what stuck with me the most was how the business had begun: as a question. A question that my friend and I had the audacity to answer for ourselves.

Why not do something about it?

Why not indeed.

Me looking out over the countryside.

*Read Part 3: Developing a Money Discipline here.

**Featured photo at the beginning of this post is of children in a backwater village in Nepal. 

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I spend hours putting it together and it only takes minutes to read.
  1. It was considered good practice for a second person to hold the ladder, acting as an anchor, but that routinely didn’t happen.
  2. Although I had no way to confirm it this was rumored to be the case with many of my coworkers.
  3. Beyonce once brought 17 semi trucks with her.
  4. I’m not sure he ever did come back.
  5. Oddly though, she recently invited me to connect with her on LinkedIn but has still never messaged me personally.

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Hello. I’m Alasdair.

Hello. I’m Alasdair.

I believe that being aware of who I am and mindful of who I am becoming is the best investment I can make in my life —and that when we focus our efforts within, the rewards naturally flow outward to those we love and through the communities we belong to.