Monkey See, Monkey Do

Ryan Rickerts
19 min readMay 13, 2021

This article is a response to a prompt by Balaji Srinivasan on his task completion project, It will get much more personal than intellectual. I will use a compact version of my life story thus far — the familial, financial, educational, and professional parts — as anecdotal evidence to help shade the contrasts written by Balaji in Founding vs. Inheriting.

I also hope to draw in some similarities, as the world is not so binary as our computer-oriented logic prefers to fashion it, either true or false (1 or 0). In fact, as a natural phenomena, our human tendencies would better be described in the terms of quantum bits — or qubits — which can exist simultaneously in both positions (aka superposition).

Baby macaque imitating facial expressions (source: Wikipedia)

I am investing some time at my keyboard today, writing standard bits to our collective cloud memory, in support of the hypothesis that founding anything is hard — but very necessary — work on the path of evolving society, while inheriting is easier and therefore a much more likely avenue for most would-be innovators. Balaji categorizes the former as the “West Coast” approach, placing the Silicon Valley boom as analogous with the American frontier mindset, and the latter outcome as “East Coast” which is synonymous with old money and more entrenched institutions (e.g. U.S. Congress, Wall Street, etc.).

I also appreciate his terminology of “crypto” or “decentralized” as the new term for any cutting edge, startup mentality and “fiat” or “centralized” for the older model. I first learned of the existence of Mr. Srinivasan from his interview on Tim Ferriss’ podcast, an episode entitled Bitcoin and Ethereum, Crypto Oracles, and More. I’m obviously at least an observer of blockchain technology and cryptocurrency where the referenced author made some of his own fame & fortune. I’m also a big fan of the pseudonymous inventor of Bitcoin, Satoshi Nakamoto, who Balaji lists as on par (eventually) with the founder of the U.S. central banking system, Alexander Hamilton.

Now that you know a few of my biases, let’s ask a few framing questions:
What type of attributes must a person have to pull off massive feats such as those mentioned, and once discovered, should we aspire to incorporate this mentality into our everyday decisions?
What are the tradeoffs of adopting such an aggressive stance?

I hope to unpack a bit of the answers in my story, as I’ve always seen myself as much more of a Founder type than Inheritor. That being said, we are all standing on the shoulders of Giants, and I will be recognizing that I have inherited a great deal of assets, just not all in a material form.

Now, for my story. Buckle your seatbelt, as this will be a long, bumpy ride. Feel free to skip to the final section if you don’t benefit much from allegory — I won’t take it personally. It’s possible I just needed to write this down.

My father, Robert Rickerts, grew up in Palo Alto in the 1960s in the shadow of that startup-making factory, Stanford, from which students emerged to found nearly 40,000 companies since the year 1930. The brick home he grew up in was situated among mostly orchards and now, sitting at the heart of the tech-fueled real estate boom in the Greater Bay Area, is likely worth millions of dollars. However, my grandparents of German descent, Richard and Helen Rickerts, spent their retirement in a mobile home park in nearby Sunnyvale. So whenever they sold that home, it likely did not set them up for a very cushy retirement, as my grandfather was a humble pipe fitter for submarines. He left an amazing legacy, however, by bringing the martial arts of judo and jujitsu back from his service during World War II on the Hawaiian islands to the Bay Area. His legacy, fortunately, is well documented on the internet.

My grandfather, Richard (Dick) Rickerts

My father’s highest level of educational achievement was an Associates Degree. On the day of my birth in 1976 in small-town Coeur d’Alene, ID — the site of my mother’s even more humble upbringing (described next) — he was on staff at the Kootenai County Hospital as a respiratory therapist. That role, plus being the maintenance man at a condominium complex in Saratoga, CA, were the only “real” jobs I remember him holding. He was a serial entrepreneur and tried many different ideas — chimney sweeping, passive solar home building, smoking cessation therapy, exercise machine inventing — but he persisted at very few. Spoiler alert: he succeeded at none of them.

When I was about 11 years old, in the year 1988, my father inherited a small sum of cash from a great aunt who passed. My guess is the sum was less than $100K, just enough to give him the confidence to quit his maintenance job in Cali, move back to North Idaho to spend more time with my sister and I, buy a small house, and purchase the capital required to start an innovative small business. This time he chose concrete restoration and named the company New Surface Construction. When a homeowner’s concrete driveway or sidewalk inevitably filled with cracks as the soil beneath it shifted under a freeze and thaw cycle, he could offer to patch it for less cost than replacing it, as well as offer that good-as-new concrete look!

My first job would be working a few days for him, and I remember seeing the outcome after a day of curing. I could see the old cracks appearing and foolishly pointed them out in front of the customer (I was too young to know better). The product may have been technologically immature, or Dad was mixing or applying the product incorrectly, applying it under the unfavorable temperature or moisture conditions, or it was a hard sell in that particular market, or possibly a combination of all of these factors. The field can be an unkind place for experimentation if you have no budget for learning from mistakes.

My father fell under hard times, couldn’t pay his mortgage or the debt on all the snazzy concrete resurfacing equipment he had purchased, and became severely depressed. He committed suicide when I was 12 years old, the day after my puppy died (coincidentally because she didn’t receive consistent & timely vaccinations for Canine Coronavirus Disease, or CCoV). His sister in California was named executor of estate, but she could not (or would not) make the trip to handle disposition of his assets. My distraught and bitter mother took over even though they had been divorced for six years because she was the only adult close to him in the area. She held a massive yard sale and sold every last bench vice and hammer. I received approx. $800 from the proceeds with which I bought a dirt bike. I also have a wood burl coffee table that he refinished sitting in my living room. This was the extent of my inheritance from my father’s side.

Before his death, I had been working on a hobby engineering project with a dear friend, one of the funniest and most intelligent tinkerers in my childhood circle. We planned to build an underwater vehicle powered by two bicycles and were researching suitable vessels to install them into. The last breakthrough I remember was seeing a yard full of septic tanks. We were trying to determine how we could install windows in the plastic that could withstand the pressure of a 50 foot dive in Lake Coeur d’Alene. After his death, the project stalled. My last memory as an aspiring inventor was what it would feel like to pedal a plastic tank underwater without windows. I do not recall attempting to innovate for a very long time after that fateful day in October 1989.

I wish to tell you the maternal side of my lineage was a happier tale with a better outcome, but it was not. It was only different, first & foremost being a lineage of Irish Catholic farmers and lumberjacks who landed out West in Northern Idaho near the turn of the 20th century, truly a wild frontier kind of place. My grandfather owned a lumber mill in St Maries, ID (total population in 2019 was still less than 3,000). He died in his early 30s of an asthma-induced heart attack when my mother was 3 years old. My grandmother remarried and moved to Coeur d’Alene where my mother spent the rest of her days. Mom was a hard-talking, hard-smoking, and hard-drinking woman who remained dedicated to a steady paycheck to feed her kids and keep a roof over the head, although not much more. She worked mainly as a bookkeeper and office manager in various small manufacturing companies, answering phones and keeping an eye on the administrative details.

Jenifer Ryan (her maiden name) finally bought her own house when I was in middle school ca. 1990 (with any money from my father’s liquidated estate, I do not know, but certainly no family money). She remarried a humble laborer a few years later, a man who performed car body work and restored antique models for a living (my second job was sanding the patches made in dented metal). When my mom died in 2017, the house had been refinanced several times to fund her “retirement” as she was sick with smoking-related cancer conditions for at least a decade. Medicaid and Social Security helped her limp along financially until the end at age 68. Her last word to her second husband was spoken while holding a checkbook writing out a payment for a medical bill.

Needless to say, I once again inherited nothing. The house I grew up in and she died in now belongs to her new husband, and I may one day see money from it, but I’m not counting on it.

This was a very long-winded way of leading you into a situation where a person can start from zero and truly have to bootstrap to find any modicum of success. I worked very hard in high school to earn academic scholarships for nearby community and state colleges. My undergraduate degree in Math & Computer Science took 10 years to complete because I was simultaneously working to stay afloat and changing majors towards those with promising salaries in local job markets (since big cities intimidated me) from Wildlife Biology to Mechanical Engineering to Mathematics to Computer Science (job description: programmer). After the scholarship money disappeared or drifted towards candidates needing a bigger equality boost (I am white and male), I carried federally-backed loans that took 15 years to pay off.

While attending Western Washington University in Bellingham, WA, I started the college’s first cycling team in 2003. I followed the models of other university teams (such as Stanford’s) by hand-building a website, designing jerseys, soliciting outside sponsors, pitching our budget to the Campus Recreation department, recruiting riders, scheduling rides, and hosting events. By the time I graduated in 2005, our team had won the Northwest Collegiate Cycling Conference, topping elite schools like the University of Washington, and qualified for Nationals. Our riders took first and second place in the Div. II road race in Lawrence, KS that year (pictured). The team continues to function much under the same format to this day. Even the logo we designed remains.

WWU Cycling was Northwest Collegiate Cycling Conference Div. II champions in 2005 (source: Bill Wykoff)

After graduation, I entered the family life (marriage & baby) and an attempt at home ownership. When I bought a house in 2005 shortly after college graduation with my wife at the time, we borrowed 100% (because you could, and her parents offered no down payment either). After putting a chunk of my first good salary as a programmer in the finance industry towards some nice upgrades, we still lost that house during the 2008 financial crisis. This coincided with our divorce, and we came out quite negative economically from it. I felt doomed to be repeating nearly the exact scenario my parents faced in 1979 when the bank foreclosed on the underground house my dad had built in N. Idaho, a truly rare design for the time. They divorced within a few years when I was six years old. My daughter at the time of our split in 2009 was two years old.

I continued to hold the same drab job for 12 years at this small West Coast investment firm because they paid well and I was able to slog my way financially forward, even after the relatively high cost of living in Bellingham, WA (i.e. rent and food), child support, and debt payments. Not feeling satisfied with my contribution to humanity, I started a bicycle race series in 2007 that ran for 10 years under the name Cascade Cross Series (‘cross being short for cyclocross). I hosted over 60 events on weekends between October and January. The events were never really “profitable” as I pumped all proceeds back into the series in the form of prizes, series finale parties, or equipment for the next season (shown below). I gave away the series in 2017 to a community-oriented guy who converted it to a non-profit. Except for the 2020–21 season, the series continues to function much as I created it. The formula was working and didn’t need changing. The template had been created, and I was satisfied to pass it on for posterity. I was also exhausted, and I had likely made less than $10/hour for my cumulative efforts over the decade.

Cascade Cross Series finale party with custom awards, ca. 2013

I dove back into real estate in 2014 by purchasing a rural acre in Maple Falls, WA for $80,000. It came with a working water well, a functioning septic system, and a dilapidated 50 year old cabin. It seemed like a humble way to start over and build basically from scratch in the middle of nowhere. It had been passed down through the family through a few generations, and was called The Alta.

Although many would have torn the existing structure down and started over, I spent the next year fixing it up to make a cozy ski cabin, then another round of improvements, then another round to make my daughter her own loft bedroom (stairs are pictured).

While working in the city full time and paying the high rent prices, I eventually put the cabin on AirBnB. This appealed to folks seeking retreat from Seattle or Vancouver and eager to ski or hike near Mt Baker. I acted as both host and cleaning staff while also holding my day job and co-parenting my young daughter. It was like second job and a decent way to offset the costs of this investment. When the COVID lockdown began in the spring of 2020, I vacated my rental house and moved to the cabin full-time and began working remote.

Besides this humble investment which has ultimately worked out in my favor (it’s likely worth less around $200K and I owe $110K on it), I have owned a few other mainstream asset classes through my employer’s 401k plan. I was not allowed to hold Bitcoin or participate in any other risky or non-traditional investment vehicles such as IPOs, but I have a balanced mix of mutual funds and equities in established tech companies. I continue to monitor these assets in an IRA Rollover account held through my former employer. This local company was a retirement-focused financial services provider, so they were quite generous in helping me build the type of wealth “focused on the future” via profit-sharing and bonuses, and for that I am grateful.

So did I inherit a bit of wealth from that founding family? Or did I shave off from their relatively massive fortunes what was deserved through the sweat of my brow and liberal use of my ingenuity to further their company mission? I sometimes felt a bit like a just another racehorse in their corral, as they could afford to keep me around even weren’t they weren’t really leveraging my talents to their full capacity. It was nice for them to have me on reserve, and it was nice for me to feel safe financially after my upbringing. I more often felt like I was being compensated for the opportunity cost of going out into the wider world where true opportunity awaits (but may be far less family friendly).

Getting a taste of the rich man’s world was obviously attractive to me, although it was clearly a nepotistic, inheritance-driven business run in a conservative fashion within a highly institutionalized industry. Any attempt at true innovation was an uphill battle, especially with the company founder (the father of the current president) still pulling the puppet strings. I admired him for taking an East Coast model from his early career in Chicago and migrating out West back to his roots in Bellingham, starting a family business in the early 90s with a very small staff, and building his own software systems based on Apple computers (which were faux pas to non-existent in the finance industry back then).

However, his drive for innovation petered out once the company reached a certain size, stabilized, and was passed on to the second generation near his retirement (much as we have seen with the other big tech firms like Apple). His daughter continued to mimic the existing model and brought very few original ideas to the table. I witnessed a focus on status, appearances, competing with entrenched players, safety, stability, continuity… not exactly characteristics synonymous with innovation. We were West Coast but looking at the Inheritance model directly in the face. I pushed the envelope as far as I could as an Instigator/Founder persona, often bumping against management prerogatives and landing myself on probation for “insubordination,” until my tolerance for favoring these other priorities hit an inevitable limit.

buy a home together

My next attempt at forwarding my career ambitions would be flavored by a complete flip in the approach. I joined a startup founded by a group of friends, and it would involve helping ordinary folks purchase real estate where otherwise they are being left out of the equation.

For a founders group, we had what appeared to be a dream team: a middle-aged, ambitious white guy very experienced in running a real estate brokerage; a middle-aged, ambitious white guy very experienced in running marketing & advertising campaigns; a middle-aged, ambitious white guy very experienced in business administration; and a middle-aged, ambitious white guy — aka myself — very experienced in technology. It seemed like an awesome recipe for success, other than the combination of egos in a relatively tiny space (running a small company), plus the remote-only factor, and something described by Balaji on which inspired this long story. That is, we applied existing approaches learned in our previous incarnations — real estate, marketing, business administration, and enterprise technology — to try and hack a problem that may require a fundamentally new approach. That approach may be so foreign and scary — a sign of true innovation — that the conservative sides of our collective company mind could not see it.

After listening to Balaji’s talk with Tim Ferriss very closely, I begin to realize the value and possibility of building a cloud country. That is, a discontiguous collection of real estate owners, where the network is the product. Through the use of technology, we could gather like-minded people who purchased homes under this belief system — supporting, aligning, and connecting them with tools for their home ownership journey. We could issue a cryptocurrency that captured their fractional ownership of property, no matter where it is physically located on the planet, like shares of a company. That ownership percentage could be pegged against any currency, much like BTC is often compared to USD but exists independently of it. When members of the network wanted to trade homes (few people who sell their primary home don’t purchase another one immediately and cough up massive fees to intermediaries), this cryptocurrency could be used as a medium of exchange. Only one out of three of my fellow co-founders even wanted to entertain the conversation. “We’re not doing crypto,” said the other two.

After a solid six months of collective efforts in sales, marketing, business, and technology development with over a dozen pitches to potential investors, we had little traction among our target consumers and only a small war chest for a few months’ worth of salaries. Like a match on a dry pile of tinder, it took only a wrongly timed disagreement with the original founder to trigger an aggressive firing response. I had pushed on the wrong ego button by openly questioning his competency and was unceremoniously exited from the company. I walked away with only two months of salary for seven months of near full-time work and a legal offer for only 1/4 of my 5% equity stake in the company (which may ultimately be worthless). Meanwhile, I had burned through significant chunk of my personal savings from my previous stint in finance to sustain myself during the company’s incubation period. The other founders had deeper pockets, stronger connections to big money, and more refined online etiquette, so they remain engaged in the team effort (so far).

I seem to have landed myself, once again, in nearly the exact scenario my father had created for himself 30 years earlier, although I “inherited” a wad of cash from myself (i.e. providing my labor to someone else who inherited a steady revenue producing institution). The dozen years I spent suffering in a stifling corporate environment to provide an emergency cushion, plus my continuous effort on advancing my technical skills and education (I am just finishing a self-funded online Masters in Computer Science degree at UIUC via Coursera), are making a significant difference in preventing a total panic or depressive response. I also have the great fortune of our higher general awareness today around of mental health & wellness. Perhaps unlike men of my father’s generation, I do not value my life only in terms of financial or career status. My psychological pump has been primed for a positive outlook on this situation.

Objectively, I’m noticing how much of our behaviors, belief systems, and status in society are inherited. Generational wealth and hand-me-downs in the form of real estate, seed money for business startups, successful business models, and even recognized family names are very real factors in traditional success and acquisition of power, despite the myth of meritocracy in America. How many people in this country really start with nothing and build something amazing?

Rather than getting mired in poor odds and apparent impossibilities, let’s try a shift in perspective by flipping the question: can one apply their ideas, states of mind, beliefs, and even money & resources inherited from previous experiences (even previous generations) to found something completely new? Or must you engage yourself in such a way that abilities emerge to solve the problem that otherwise would have remained latent? In other words, will the situation you find yourself in creating a company make you so desperate to succeed that you will entertain any idea, no matter how radical, and a new thing emerges? Ye olde “Necessity is the mother of invention” or even Survival mode.

I used to get angry about my inheritance (or lack thereof) from my parents. I would dwell in a quiet state of victimhood where I had received nothing and most other successful people I observed — whether fundamentally talented or not — had some sort of backing, inspiration, or confidence from their previous generation. The only transcendence I could find from this oppressive view came from the old adage, Give a Man a Fish or Teach a Man to Fish:

Maybe I have been overthinking it. Success is not that hard. Maybe my parents didn’t give me material things with which to start my adult life other than food & shelter. Maybe they didn’t hand me a tool or skillset that led to the acquisition of more material things, such as knowing how to fish. They did give me the ability to think, to innovate, to strive, to discover the skills that lead to possessions (aka assets) and meeting of physical needs. That ability came purely through giving me life and leaving me with the desire to stay alive. That’s it! They left me hungry and smart but not excessively damaged or dead.

A hungry person who doesn’t know how to fish or find other food will find the way, or they will die. That is a true Founder, like Tom Hanks’ character in Cast Away. Those who do not want to face the prospect of death would never choose this mode of education, so I conjecture it is therefore rare. Safety, security, avoidance of deadly scenarios… these are primal desires for any living creature.

Yet, we have all inherited a planet abundant with food, oxygen and water, our inherent intelligence, our functioning bodies and physical strength, a community willing to support us, all things written or recorded in languages we can understand, and an abundance of examples of successful people eager to share what they have learned (such as Balaji).

I venture to say none of us are truly alone in our quest to thrive. Most of us inherit our approaches, much as all primates and many mammals learn through copying those that came before. A few must start from scratch and they might be better for it, even if not formally recognized. Ask yourself: Who was the first chimpanzee to poke a stick in an ant hill? How hungry were they?

Chimpanzees indeed possess culture when it is defined as the transmission of information from generation to generation via social learning. Source:

Like all humans, I was born into a situation that I strive not to resent. However, I often wonder if contrary to Nietzsche’s famous saying, I am not still disadvantaged. Psychological research has found that what doesn’t kill you, makes you weaker:

Another reason is that American culture, itself born of trauma and imbued with a hopeful can-do ethos, wants to believe this idea, finding it self-affirming. Once we have acquired a certain belief, we tend to see, remember, and report mostly instances and events that support it.

Would I have rather been handed a bag of tools (money, companies, skills) with which to succeed at feeding & sheltering myself, my offspring, and even some family, friends, and the community who surrounds me? Certainly.

Will I “fail at life” as a result of this not happening? Not likely. I am too determined after seeing my predecessors fail, at least by my standards. They did succeed at passing the pure experience of life on to me, so who am I to judge?

Will society gain a new approach to existence as a result of my survivalist-mode inspired innovation? Likely. Otherwise, I wouldn’t be motivated enough to write this article.

Will I be personally “better off” at the end of my life as a result of this outcome? Not likely. However, I seem to have no other choice, so who am I to question what is the best use of this one life I have been granted?

Will I pass on whatever I succeed at building to my daughter to make her life easier? Certainly.

Perhaps the personal satisfaction from handling this dilemma of these two seemingly competing forces — Founding vs. Inheriting — is the great reward. The journey is the destination.

Thanks for reading,