Meet Kirk
Meet Kirk Drake – the entrepreneur, author, and keynote speaker on a mission to disrupt business norms and accelerate innovation with adventure, integrity, and humor.
With decades of experience as a digital architect and technology pioneer in both the credit union and fintech spaces, Kirk is a master at using humor to explain complex ideas and drive change.
As a serial entrepreneur with limitless creativity, Kirk is not afraid to challenge the status quo and push boundaries in order to achieve success. With his captivating presence, strategic thinking, and visionary approach, he inspires audiences to think outside the box and embrace disruptive ideas that can revolutionize their industries.
He founded Ongoing Operations, acquired by Trellance in 2022, co-founded CU Wallet, acquired by the Michigan Credit Union League in 2016, and founded CU 2.0, a fintech and AI digital studio for credit unions that grew out of his 2017 book. He is President of XDI, a document intelligence platform for financial institutions, and founder and President of Painted Hills CUSO, and has been part of eight exits as a founder or owner. At home in Ashland he and his wife run Resistance Wine Company, where she makes the wine and his AI tools keep the books.
In addition to his extensive career in technology and entrepreneurship, Kirk is also a published author and sought-after speaker who has brought his message of innovation and humor to countless events and organizations. With his deep thinking and sharp wit, he delivers keynote speeches that leave audiences feeling energized, inspired, and ready to tackle the future with a fresh perspective.
Whether you're looking to disrupt the norm, challenge your thinking, or simply add a touch of humor to your next event, Kirk Drake is the visionary leader you've been searching for.
Join him on his mission to shake up the business world, and prepare to be inspired, entertained, and transformed.
Fun facts
- Orange Theory Classes Attended
- 578Orange Theory Classes Attended
- Wineries Visited
- 238Wineries Visited
- Keynotes
- 147Keynotes
- Fintechs Launched
- 98Fintechs Launched
- Years in Banking/Credit Unions
- 30Years in Banking/Credit Unions
- Comedy Shows
- 7Comedy Shows
- Books Written
- 2Books Written
- Wife
- 1Wife
Frequently Asked
- Who is Kirk Drake?
- Kirk Drake is an author, keynote speaker, digital architect, and technology pioneer based in Ashland, Oregon. He's spent three decades in credit unions and fintech, building companies and speaking on AI, disruption, and building an anti-ordinary business.
- What companies has Kirk Drake founded?
- Kirk founded Ongoing Operations, a disaster-recovery and cloud CUSO acquired by Trellance in 2022; co-founded CU Wallet, acquired by the Michigan Credit Union League in 2016; and founded CU 2.0, a fintech and AI digital studio for credit unions, and Painted Hills CUSO, where he is President. He is also President of XDI, a document intelligence platform for financial institutions, and runs Resistance Wine Company with his wife, its winemaker. He has been part of eight exits as a founder or owner.
- What books has Kirk Drake written?
- Kirk wrote "FinAncIal: Helping Financial Services Executives Prepare for an Artificial World" (2020), on what financial services leaders need to know and do about AI, and "CU 2.0: A Guide for Credit Unions Competing in the Digital Age" (2017), a plan for credit unions to use technology to compete with banks.
- What does Kirk Drake speak about?
- "Disrupt or Get Disrupted: AI for Credit Unions," "Anti-Ordinary: Building It All With AI," and "AI, Meet Compliance" — keynotes on where AI creates real value, how regulated institutions adopt it safely, and how he runs a portfolio of very different businesses on the same AI playbook.