Stephen Cole, co-founder and CEO of Castle, joins Sunny Ray to trace his path from a small Missouri town to building Bitcoin powered financial infrastructure for small and medium businesses. Cole recounts learning to code in Visual Basic under a high school teacher, self studying at a community college library, and starting his career at eBay in 2008 during the financial crisis, largely oblivious to the macro chaos around him. He describes the jump from corporate eBay to scrappy startup Cloudscaling, later acquired by EMC and then Dell, and a formative stint at PayPal during its 2010 censorship of Wikileaks payments. Cole explains how Ayn Rand, Ron Paul, and Austrian economics reshaped his worldview before he discovered Bitcoin in 2012 and bought his first coins in early 2013 amid the Mt. Gox collapse. The conversation closes on why holding Bitcoin is itself a valid use case and how that philosophy now drives Castle's mission to bring Bitcoin powered financial products to the 35 million small businesses across the US.
Castle CEO Stephen Cole on Austrian economics, PayPal censorship, and building Bitcoin infrastructure for small businesses.
What are you building at Castle?
I'm co-founder and CEO of Castle. We're building financial infrastructure for small and medium businesses powered by Bitcoin. SMBs have been overlooked compared to individual investors or Wall Street. There are 35 million SMBs in the US alone, and we're laser focused on giving them Bitcoin powered products so they can upgrade their financial stack and get a leg up on competition.
Take me back to young Stephen. What was the kid like before computers and capital markets took over your life?
I just turned 40, born in 1986, and grew up in a small town in Missouri. I remember life before the internet and watched it transform the world after being misunderstood at first. I saw small business owners on Main Street with real pride and craftsmanship, and that stuck with me. I studied computer science and moved to Silicon Valley, but that small town still feels like home.
When did code first click for you, and who lit that spark?
A high school teacher, Dr. Cummins, changed my life. He taught the only computing class in my small town school, in Visual Basic, and I was hooked at fifteen. I kept asking for more, so the faculty let me work in IT for credit while I read bulky computer books and stacked up certifications like Linux+ and A+, even before I'd touched a real Linux server.
You started your career around 2008, as the financial system was melting down. How did that shape how you thought about money?
Honestly it didn't shape me at the time. I started at eBay in 2008 right as everything was melting down, but I was so heads down learning tech that I barely registered the layoffs happening around me. It wasn't until years later, looking back, that I realized how significant that moment was. I feel fortunate it played out the way it did for me.
eBay and Cloudscaling back to back, scrappy startups and giant enterprises. What did each teach you that you still carry today?
eBay taught me the ins and outs of big corporates, the good and the unnecessary red tape. Around 2012 I became enchanted with startups when a leader I admired left eBay for a tiny cloud computing startup called Cloudscaling. I bugged them until they hired me, and I loved the small team and mission driven energy so much I knew I wanted to stay startup centric going forward.
Ayn Rand, Ron Paul, Rothbard. What was the first idea that really cracked your worldview open?
Atlas Shrugged changed my life. It gave me a profound respect for builders and for the nobility of any work, blue collar or white collar. It also planted seeds about money, like why gold matters and why value shouldn't be printed out of thin air. Ron Paul's 2008 campaign sent me down a related path when he talked about eliminating the IRS and introduced me to Mises and Austrian economics.
In 2010 you were an engineer at PayPal when they censored Wikileaks. Walk me through what you were thinking in that moment.
I worked in PayPal's network operations center when PayPal censored payments to Wikileaks. My job became defending against denial of service attacks from Anonymous in retaliation. Once the dust settled, I remember thinking, are we the good guys? Wikileaks told a hard truth and we censored the truth tellers. That was the first time I really questioned the centralization of money and censorable payments.
Take us back. You find Bitcoin. Paint the scene, what made you click the link?
A friend kept emailing me about Bitcoin in 2012 when it was three dollars, but I was too busy to listen. He ended up trying to build mining chips instead of buying and never owned any. I finally bought my first bit in early 2013 during the Mt. Gox meltdown, and the price crashed right after, which forced me to research it more seriously.
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