Sunny Ray sits down with Mitchell Clarke, an investor relations professional whose career put him inside NASDAQ headquarters during Bitcoin's 2017 run. Mitchell explains how watching listed companies rebrand overnight from gold mining or marijuana to Bitcoin, often without real conviction, left him wary of the industry even as he made a small first purchase. He describes how a gold-bug father-in-law, the March 2020 market crisis, and zero interest rates pushed him to buy again and dive into the sound money rabbit hole. The turning point came when Michael Saylor began his podcast circuit after Micro Strategy bought Bitcoin. Having worked with hundreds of public company executives, Mitchell says he could quickly tell Saylor was a serious person. The conversation also covers why position sizing kept him from selling through the 2018 bear market, how treasury companies change the way newcomers get onboarded, and his current focus on the digital credit market.
After watching public companies chase Bitcoin as a fad, Mitchell Clarke explains why Michael Saylor finally made him a believer.
What did working inside NASDAQ teach you about public companies and Bitcoin?
I saw companies pivot from gold mining or marijuana to Bitcoin just because money was flowing there, not because they understood the sound money thesis. Some of the fundraising and structures had questionable moral elements. At that point I also didn't separate Bitcoin from broader crypto, so what I saw honestly turned me off the industry.
You first bought Bitcoin in 2017 but not a material amount. What held you back from going deeper?
It was too scary, and I didn't know what I didn't know. I asked a colleague what Bitcoin was and they said it's money, which didn't help. I had no books and no Bitcoiner friends, only CNBC. I finally downloaded Coinbase and bought about a month's paycheck plus commission, then watched it drop.
What kept you from selling or writing it off during 2018 and 2019?
Selling felt pointless after it had already dropped so much, and I kept seeing positive posts from people like Anthony Pompiano. Mostly, though, I owned a small amount, so I could stay calm. Without real conviction and hundreds or thousands of hours of study, you shouldn't own material amounts of Bitcoin.
How did your father-in-law's gold bug arguments shape how you first understood Bitcoin?
I was already sympathetic, since I'm conservative and went to a Ron Paul rally years ago. But gold never computed for me as a medium of exchange. Bitcoin is the evolution from the physical to the digital realm, with a hard cap of 21 million, and you can send huge value across the world instantly.
What changed in March 2020 and when Michael Saylor entered the picture?
When the crisis hit and rates went to zero with money flooding the system, I realized the Bitcoin and gold guys were right, so I bought again around $7,000. Then I watched Saylor's first interviews. I've dealt with hundreds of executives and could tell he was serious. He made me see Bitcoin as its own asset, beyond gold.
What other Saylor concepts resonated with you, and how has onboarding into Bitcoin changed?
His series with Robert Breedlove, tracing mediums of exchange from barter to seashells and beyond, was very instrumental. Back in 2020 the message was purely Bitcoin, with no treasury companies or ETFs. You had to buy real Bitcoin and understand the thesis. Many people in 2025 got onboarded through treasury companies, which is a very different experience.
What are you most interested in now?
The digital credit market, which I think is a multi-trillion dollar opportunity. I'm especially interested in STRK. As a former real estate investor, I wish it had existed then. It pays around a 10 and a half percent yield, with return of capital treatment that is tax free in the US, and none of the tenant or insurance headaches.
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