Kendall Weihe, Jordan's co-founder at Bitment, joins the pod for a rare deep dive into what actually changed in software engineering — and by extension, financial services — over the last 12 months.
Kendall walks through his path from a corporate software engineering job at KFC to Coinmetrics (Nick Carter's data analytics company), to Jack Dorsey's Block, where he worked on the TBDEX decentralized exchange protocol, and finally into stablecoins before going all-in on Bitment. Along the way: why cold emails still work, why he thinks the "VC talking his book" critique of Nick Carter misses the point, and what it was actually like spending two days a year frying chicken as a corporate KFC policy.
The back half is the real meat: Kendall argues that since roughly December 2025, AI coding tools have fundamentally changed what it means to build software — he barely writes or reads code anymore, and instead manages AI agents the way he'd manage employees. He breaks down why software was ground zero for this shift (Linux standardization, decades of developers automating their own jobs) while human systems like finance, law, and government will take much longer to diffuse. He also makes the case for vibe coding as a communication tool rather than a shortcut, uses a "skyscraper" analogy for why AI-assisted engineering is still laborious, and lays out his vertical-vs-horizontal, diffusion-vs-standardization framework for what a real AI-native operating system for financial services actually requires.
Chapters
00:00 Introduction
01:35 How Kendall and Jordan Met
03:22 Kendall's Background: KFC to Coinmetrics to Block
06:27 Inside TBDEX: Building a Decentralized Exchange at Block
08:56 The KFC Colonel Question
10:35 Cold Emails and Getting Into Coinmetrics
12:46 Is Nick Carter Misunderstood?
16:07 Double-Entry Bookkeeping, Bitcoin, and AI for Financial Advisors
22:03 "Learn to Code" Aged Poorly: AI and the Disruption of Software Engineering
28:35 Vibe Coding: Powerful Tool, Dangerous Shortcut
33:41 The Skyscraper Theory of AI-Assisted Engineering
36:38 Diffusion vs. Standardization: Decentralizing Big Tech
43:56 Vertical vs. Horizontal: What It Takes to Build an AI-Native OS
47:40 Closing Thoughts
Host Links
Wyatt O'Rourke
X: x.com/wyattorourke_
Website: basilic.io
Jordan Guess
X: x.com/jordanguess
LinkedIn: linkedin.com/in/jordan-guess-cpa
Website: bitment.co
Bitcoin Financial Services Media
X: x.com/bffs_media
Website: bffs.media
YouTube: @bffs_media
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