“What if we could do it better than anyone else in the ecosystem?” Nathan McCauley asked himself while co-founding Anchorage Digital, a unicorn assets platform that provides instantly settled key storage and custody—holding investments on behalf of investors—for digital assets like Bitcoin and Ethereum. Before starting this venture, he worked at financial services platform Square, where he performed what he called “financial security” for four years with his future Anchorage Digital co-founder Diogo Monica. There the two helped to design the digital card reader with Jack Dorsey. Wanting to learn more about the sales, marketing and development aspects of B2B business before starting their own company, he and Diogo joined Docker, a software platform that helps developers to build, run and share applications.
Nathan talks about working at Square with Jack Dorsey and Keith Rabois, their unique approaches to leadership, and what the experience at Docker was versus what he thought it was going to be. Brendan explains the problem with overindexing on opportunities to make what turn out to be largely unneeded products. Early on in his career, Nathan’s managers constantly evaluated him as having “irrational optimism.” He later learned about the power of being paranoid.
Nathan started Anchorage because he wanted to build a culture, one in which his employees could find a purpose and enrich their lives. With this motivation still at the forefront, he spends a lot of time interviewing potential employees. He explains the key to finding the right people who align with the company’s mission.
Quotes:
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“This idea of sitting around and waiting for good opportunities and then when you find them, putting everything into them. One of the things that would’ve happened if I decided to start a company just after Square is I would’ve probably gone after a smaller opportunity that wasn’t as high leverage as Anchorage. And so I’m extremely grateful for the patience aspect of it. In terms of waiting for the right opportunity, that was a good fit for mine and my co-founders’ skillset. That’s not to say that I didn’t learn a ton from Docker. I actually did learn a ton from Docker too. But it’s kind of a dual purpose of learning a lot, learning about enterprise sales, learning about marketing, but also not jumping into something that was not as big of an opportunity as it possibly could have been.” ([24:29]-[25:18] | Nathan)
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“We had this idea of a very secure system without a problem that actually needed solving that way, the custody problem coming along was almost this conceptual model of an idea of a very secure system that finally had a use case that we could build towards. So the answer to that ends up being that we had a very clear product vision very early on what needed to get built, but we did not want to build an mvp. because we knew the very nature of the product was likely to hold non-trivial amounts of funds very early on. We didn’t want to do anything less than good enough in the first version.” ([29:44]-[30:27] | Nathan)
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“The most useful outlet for fear is to keep innovating.” ([35:46]-[35:50] | Nathan)
Connect with Brendan Dell:
LinkedIn: https://www.linkedin.com/in/brendandell/
YouTube: https://www.youtube.com/c/BrendanDell
Instagram: @thebrendandell
TikTok: @brendandell39
Buy a copy of Brendan’s Book, The 12 Immutable Laws of High-Impact Messaging: https://www.indiebound.org/book/9780578210926
Connect with Nathan McCauley:
Anchorage.com
Check out Nathan’s recommended books:
Only the Paranoid Survive: How to Exploit the Crisis Points that Challenge Every Company by Andrew S. Grove
https://www.indiebound.org/book/9780385483827
Titan: The Life of John D. Rockefeller, Sr. by Ron Chernow
https://www.indiebound.org/book/9781400077304
A History of the World in Ten and a Half Chapters by Julian Barnes
https://www.indiebound.org/book/9780679731375
Raids on the Unspeakable by Thomas Merton
https://www.indiebound.org/book/9780811201018
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About the Author
Brendan Dell
Brendan Dell is an author and the founder of The Daily Creative. As a freelancer he's worked with clients like Expedia, Cvent, Panasonic, Brother, Windstream and 100+ more to build unignorable tech brands. At The Daily Creative, he shares advice and lessons to help freelancers level up.
