What if gaining success only raises the stakes?

Having operated at the center of scale, Michael Tannenbaum, the former COO of Brex and now CEO of Figure and Arthur Levy, CBO of Brex, share how they’ve kept their edge, and where AI is pushing fintech next.

They join Jason Shuman to discuss:

• ​there’s more to operating than being great at finance
• ​how saying ‘no’ becomes the hardest part of success
• ​why financial services should focus on Blockchain over AI
• ​why AI is still being used as an experimental tool by enterprises

Connect with us here:

1. ​ Michael Tannenbaum- https://www.linkedin.com/in/michaeltannenbaum/
2. ​ Arthur Levy- https://www.linkedin.com/in/arthurlevy/
3. ​ Jason Shuman- https://www.linkedin.com/in/jasonshuman/
4. ​ Change Order- https://www.linkedin.com/company/change-order/
5. ​ Primary Venture Partners- https://www.linkedin.com/company/primary-venture-partners/

00:52 Introduction & Guest Background

01:11 VC-to-Operator Transition

01:50 Choosing SoFi: Strategy & Early Growth

03:07 SoFi’s Scale & Role Scope

05:52 First Meeting in Cancun & Boston Roots

07:02 Reconnecting in San Francisco & Partnerships

09:14 Mentor-to-Peer Dynamics

11:06 Recruiting Art to Brex & First Republic Deal

15:45 Role Evolution & Career Pivot at Brex

20:26 Fall ’23 Crisis & Strategic Refocus

22:04 “Big Rocks” Focus Framework

24:34 AI vs. Blockchain in Financial Services

29:59 Internal AI Adoption & Use Cases

33:02 Reimagining Sales Motion with AI

38:35 Market Segmentation & Customer Focus

41:43 Rapid-Fire Insights: Mistakes, Books, Mayoral Picks

49:24 Blockchain & Stablecoin in Capital Markets

53:02 Leading AI Adoption: Teams & Strategy

56:46 Future of SDR & GTM Roles with AI

59:59 AI’s Broader Impact on Ecosystem

1:04:27 Rapid-Fire Round: Personal Picks

1:09:51 Closing Remarks & Outro