In this episode, I sit down with Taylor Black, who leads AI and venture ecosystem work in Microsoft’s Office of the CTO and brings a deep “better-formed humans” conviction to the AI conversation. We draw a hard line between intelligence (statistical knowing) and insight—where a human knower makes the categorical leap to “this is true,” what Taylor calls grasping the “virtually unconditioned.” We talk about how LLMs can pattern experience to help us reach insight but can’t replace judgment, and why venture building should be anthropology-first: every product ships an implicit view of the human person. We cover the risk of using AI as an oracle that shortcuts productive struggle (especially in education), the importance of humility and sustaining the tension of inquiry for product-market fit, and Taylor’s “cold storage” idea—using AI as a context engine to shelve, monitor, and revive ventures when conditions change. We close on the key builder question: not what can we build, but what ought we build?

02:08 Intelligence vs Insight

02:58 Statistical Knowing

05:02 Virtually Unconditioned

09:02 Using AI Without Outsourcing Judgment

11:39 Formation in Venture Building

14:19 Anthropology First Product Design

17:56 Hard Rules for Human Flourishing

18:53 What Ought We Build

21:20 Humility and Idea Flow Playbooks

24:19 Probabilistic Products and Implicit Anthropology

28:48 AI as Oracle in Education

34:29 Cold Storage for Venture Ideas

Connect with Taylor:

• https://substack.com/@pourbrew

• https://www.linkedin.com/in/blacktaylor/

• https://leonum.catholic.edu/

• https://innovate.pourbrew.me/

Connect with Raul:

• Work with Raul: https://dogoodwork.io

• Free Growth Resources: https://dogoodwork.io/resources

• Connect with Raul on LinkedIn (DMs open): https://www.linkedin.com/in/dogoodwork/

In this episode, I sit down with Michael Lopez, a Fortune 500 transformation consultant and author of “Change,” to break down why stress and resistance can be biological signs that change is working and why leaders often abandon transformation too early. We unpack Michael’s national workforce study, Rethinking Change Management, which surveyed 1,000 U.S. employees and found “zero overlap” between the top five change supports companies provide (like emails, newsletters, and training) and the top five things employees say they actually need (time and space to experiment, coaching, permission to fail, and leaders modeling change). We also discuss the AI readiness gap—65% of executives feeling ready versus about 29% of employees—and how “licenses without direction” leads to passive resistance and stalled pilots. Michael shares what real change requires: honest expectations, redesigned incentives, and an 18–24 month adaptation journey.

01:12 Stress Means Progress

03:29 Diagnosing Change Problems

05:22 Nuclear Plant Case Study

07:32 Why Playbooks Fail

09:58 The Easy Button Trap

12:23 Pricing Change Work

16:42 Zero Overlap Finding

19:37 AI Readiness Gap

22:40 Redesigning Change Strategy

Connect with Michael:

• www.michaeljlopez.coach, IG - @michaeljlopez9, LinkedIn - https://www.linkedin.com/in/michael-j-lopez9/ , X - @MichaelJLopez9

Connect with Raul:

• Work with Raul: https://dogoodwork.io/apply

• Free Growth Resources: https://dogoodwork.io/free-growth-resources

• Connect with Raul on LinkedIn (DMs open): https://www.linkedin.com/in/dogoodwork/

In this episode, I’m joined by Jim Schleckser, founder and CEO of The CEO Project, to break down how CEOs identify and fix the real constraint in their business. We cover practical signals for finding the “kink in the hose,” including where inventory accumulates, cycle time slows, congestion builds, or customer complaints spike—and why top-performing CEOs consistently spend meaningful time at the constraint. Jim explains when the CEO becomes the bottleneck (as the constant decider or by staying stuck in a functional role) and shares his Five Hats framework: learner/analyst and player to find constraints, and architect, coach, and engineer to solve them through business design, talent, and systems. We also dig into why values and mission are part of the operating system, Jim’s grounded view of AI as mostly augmentation amid hype, and what business types may be more resilient long term.

01:25 Why Constraints Matter

03:27 Finding the Business Kink

04:51 When the CEO Is Bottleneck

07:27 Five Hats Framework

09:14 Design Talent Systems Fixes

12:27 Big Model Shifts and Pivots

13:24 Balancing CEO Hats Over Time

13:59 Client Story Clairvoyant Service

14:38 Firing Unprofitable Clients

15:39 Small Shifts That Matter

16:13 AI as Human Amplifier

17:06 Hype Cycles and ROI

18:39 Is AI Creating New Value

21:18 Professional Services Pricing Shock

22:29 Best Businesses in an AI Future

24:46 Constraints Versus Opportunities

25:19 CEO Surprises and AI Doomsday

Connect with Jim:

• IG: @the_ceoproject

• Twitter: @the_CEO_Project

• YouTube: https://www.youtube.com/@CEOProject

• LinkedIn: https://www.linkedin.com/in/jimschleckser/

• Links: Podcast: https://theceoproject.com/the-podcast/

• Website: https://theceoproject.com/ and https://jimschleckser.com/great-ceos-are-lazy/

Connect with Raul:

• Work with Raul: https://dogoodwork.io

• Free Growth Resources: https://dogoodwork.io/resources

• Connect with Raul on LinkedIn (DMs open): https://www.linkedin.com/in/dogoodwork/