On The Brink with Castle Island Alex Wilson (Cyclops) on Crypto and Stablecoin Payment Solutions (EP.706)
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Mar 4, 2026 Alex Wilson, co-founder and co-CEO of Cyclops, a payments entrepreneur who built The Giving Block and led Shift4’s crypto team. He discusses building stablecoin payment products, the team and fundraising behind Cyclops, regulatory and licensing plans, and practical pay-with-crypto, settlement, and payout solutions for merchants and payroll.
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Founding The Giving Block And Exit
- Alex Wilson and Pat Duffy started The Giving Block in 2018 to help nonprofits accept crypto donations.
- They raised funds, worked with major charities like St. Jude, and sold the company to Shift4 in 2022 after raising ~$1.5M early on.
Lessons Learned Inside Shift4
- Alex describes learning inside Shift4 under its founder and adopting values like accountability and ownership.
- He highlights the founder's background starting the company at 16 and influence from SpaceX and Elon on culture.
Pain Of Piecing Together Crypto Infrastructure
- Building crypto and stablecoin products required stitching many vendors, custom work, and internal engineering at Shift4.
- That pain motivated Alex to start Cyclops to create a more integrated, ready-made payments solution.