Blog 01: Origins
Kindling
This budding venture that is Cantilever emanates from the values of our founding team- altruism, sovereignty, humility, opportunity equity and curiosity. These values represent who we are and why we are here, building Cantilever in service of leaving the world a better place than we found it. And here’s how it started…
A Spark
The first sparks of Cantilever flew in May of 2017. During a seemingly innocuous round of golf, a colleague provided me some context around an upcoming investment opportunity for what is now a major player in the digital asset space. At this time I was leading East Coast and international investment efforts of a mezzanine investment fund - a business I was blessed to have the opportunity to help found, build and scale within Silicon Valley Bank.
This investment proved to be the catalyst for me to finally take this Bitcoin thing seriously. Operating in the technology, financial and venture capital markets, I had heard of Bitcoin numerous times over the years and each time quickly dismissed it as a fad, bubble or ponzi. This time was different. Due diligence for this investment was heavily focused on the emerging Bitcoin and crypto ecosystems - and figuring out why they were not a complete fraud. After spending some time running down the proverbial rabbit hole, I slowly accepted there could be profound innovation occurring in the budding digital asset space.
A Spark Becomes Fire.
By late summer 2017, in the midst of due diligence for this crypto investment, I was finally ready to take action on this taste of Bitcoin and crypto knowledge with some good, old-fashioned speculative FOMO. The crypto market was on a tear- throughout 2017, 1 BTC ripped from less than $1,000 to over $20,000 by year-end.
The memory of buying my first bitcoin is forever seared into memory:
August 18th, 2017. New York City. Navigating a crowded 5th Avenue with a friend who had been into Bitcoin for about a year prior. Syncing my bank account and smash buying Bitcoin on a shoddy mobile app called Coinbase.
The mezzanine investment closed in early January 2018. Three weeks later, the bottom fell out of the digital asset market at which point the real education began. It’s hard to understate the learnings that came from managing an underperforming investment on behalf of a risk-averse commercial bank amidst a bear market at a time when Bitcoin was still best known as the “money for drug dealers”. Not realizing it at the time, this was a critical forcing function keeping me engaged in the digital asset ecosystem throughout a multi-year bear market during which the prevailing narrative was that the entire category was dead.
Fire becomes a Blaze.
The drawdown in risk assets seen in March of 2020 was historic in both its speed and magnitude. In a matter of weeks, the S&P 500 lost over 30% of its market value, Bitcoin fell by nearly 70%. There was literal blood in the streets - society was afflicted by a virus the world knew next to nothing about. The mainstream narrative was that the economy was headed into a recession that would rival the Great Depression.
And yet…
Fueled by unprecedented monetary policy and fiscal stimulus by central banks and governments globally, by May of 2020 the S&P 500 was back within 10% of all-time-highs, ultimately reaching a new apex in August 2020. However, the pandemic continued to rage with no end in sight. People and businesses were still in lockdown. The disconnect between the economic reality of Main Street and the performance on Wall Street was unprecedented.
On a sunny May afternoon, I found myself on my back deck pondering all of this and kept asking the profound question of “What. The. Actual. F*ck”? How could it be that the average person was being impacted so hard by the externalities of the pandemic- small business closures, lockdowns, inability to work in-person- and yet Wall Street continues to make all time highs? The divide between the Haves and Have Nots just got significantly wider. Somehow all of this pushed me back into the study of Bitcoin - in a much more immersive and multi-disciplinary capacity.
As I ventured back down the rabbit hole, a positive feedback loop emerged- the more I learned about Bitcoin, the more I wanted to learn. Waking up at 4:00am to read books like The Bitcoin Standard and The Price of Tomorrow and looking forward to washing the dishes because that afforded me 15 minutes to listen to Parker Lewis and Lyn Alden on podcasts were a few vivid memories. Starting in June of 2020, I began strategically adding Bitcoin to my family’s investment portfolio - in parallel with my intellectual journey.
Over time and for better or worse, I emerged as the “Crypto Guy” within my social networks. With the tailwind of a raging bull market, family, friends and friends of friends began to reach out looking for guidance around how to approach these exploding ecosystems. One notable example was the emergence of a Tuesday night crypto riff with 5 of my college buddies. On these 2-3 hour calls, the group would talk about Bitcoin and crypto- ranging on anything from recent price action to the fundamental world problems the technology could be part of solving. There was also discussion within this group about how to operationalize some form of organization to make a real impact on challenges such as societal dependance on failing institutions, financial education and investment access. While it was not clear to us in those moments, many of these discussions fanned the slowly growing Cantilever flame.
The fire grows hotter
In early 2021, it became clear that spending my time in a professional capacity on anything other than Bitcoin and crypto was going to be unfulfilling. In July of 2021, I made the bittersweet decision to leave SVB, after 15 years at the only company I ever worked for. From there, I embarked on a 6-month sabbatical to spend even more time studying Bitcoin and the digital asset ecosystem at large. Being entirely freed from responsibility of output, I spent my days in deep thought while walking in nature, consuming vast amounts of content spanning books, audiobooks, podcasts, articles and having targeted discussion with those sharing interest or already operating in these ecosystems. Furthermore, leveraging my prior experience and network in the technology and venture capital markets, I began making personal investments into Bitcoin/crypto-native venture capital funds.
In November 2021, I began to transition from sabbatical life to thinking entrepreneurially about how to return to building something that mattered. The idea of going back to work on Wall Street or for a large organization was not interesting - given the misalignment between that path and my values and also the taste of entrepreneurship I got building the mezzanine business at SVB.
I then spent considerable time fleshing out how to best combine:
(i) prior experience of early stage technology investing
(ii) digital asset domain expertise
(iii) a belief and passion in/for Bitcoin and the broader digital asset ecosystem
(iv) overarching desire to make a small yet impact purposeful impact on the trajectory of humanity.
5+ years in the making, leveraging the educational and investment skills sets of our founders, Cantilever Advisors is officially born with a vision to equip all to live sovereignly and purposefully and a mission to bridge the gap for the intellectually curious interested in the digital asset ecosystem through education and investment access.
We’re fired up about the founding and potential of Cantilever. And we’re just getting started…