In this episode, I sat down with Phil Berry, founder and CEO of Northwind Health, who has bootstrapped the company for nearly 18 years to over 100 people and close to $100M in revenue while taking on massive healthcare incumbents. We compare his early survival-mode years—keeping headcount lean, fearing payroll, and carrying the business himself—with his shift toward intentional growth, leadership hiring, and asking what the business is “called to do” beyond his personal identity. Phil shares how meaning emerged through employee wins and patient outcomes, shaped by his Catholic faith and a focus on human dignity, which he frames as serving “souls,” not “lives” or “belly buttons.” We also unpack why the healthcare system functions as “sick care,” why big players can’t structurally reduce costs, and how Northwind aims to scale high-touch, waste-removing, outcomes-driven care.01:13 Founder Mindset Shifts02:18 Early Hiring and Survival06:24 Finding Meaning in Work10:25 Planning Beyond Survival13:10 Belief and Big Bets14:42 Stewardship and Scaling20:04 Separating Identity from Business22:08 Is Growth Always Right26:46 Leading in the Tension30:06 Human Flourishing Thesis34:01 Fixing Sick Care at Scale39:14 Human Dignity in Healthcare42:49 Defining a Human SoulConnect with Phillip: • Northwind https://www.northwindhealth.comPersonal website: https://www.phillipberry.comphil.berry@northwindhealth.comConnect 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/
I sat down with Bill Benjamin to break down his research on the “last 8%”—the small but crucial part of a difficult conversation or decision we often hold back because it feels risky. Bill shares how the idea started with two executives, then expanded through studies of 34,000+ people, showing we leave an average of 7.56% unsaid, and why our brains treat conflict like a threat. We talk about recognizing last 8% moments through body cues and behaviors, the two pillars of high-performing teams (connection and courage), and common defaults like avoiding or “making a mess.” We also cover why psychological safety alone isn’t enough, how leaders can model curiosity and set team norms, and why these human skills matter even more as AI adoption struggles due to fear and disengagement.00:07 Why We Hold Back01:33 What the Research Shows02:36 Brain Science of Fear03:06 Last Eight Percent Moments03:42 Individual vs Environment05:03 Body Awareness Framework07:58 Beyond Psychological Safety09:53 Avoiders and Make a Mess11:10 Skillful Hard Conversations12:32 Founder Modeling and Norms14:50 AI Makes Humans Matter18:51 Disengagement and Connection20:09 Who Does It Best22:20 Bill Personal Turning Point24:06 Toughest Partner MomentConnect with Bill: • www.ihhp.com• https://www.linkedin.com/in/bill-benjamin-12b671/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/
AI As Strategy Workshop: Work and Grow at the Speed of Your ThoughtsMost conversations about AI begin with the model. This workshop begins with the business.In this episode explores AI as a strategy question across ownership, ethics, operating design, pricing, and net new value. Raul breaks down the AI COO harness he built for Do Good Work, explains the 5 ingredients inside it, and shares practical examples of how agents support his work without taking control of the relationships or decisions that matter.Use the episode as a workshop with your team. By the end, you will have 2 questions to work through: what you wish your business could do today, and where your business model will need to evolve next.What You'll LearnWhy a good model is just a brilliant stranger, and what makes AI useful inside a real businessThe 3 parts of AI sovereignty: your data, the model, and the harness around bothHow the restaurant analogy explains orchestrators, agents, skills, hooks, memory, and rulesThe 5 ingredients every owned AI system needsWhy every product carries a belief about people, and how Raul's 9 operating values protect human flourishingWhy memory, security, compliance, and human approval have to be designed togetherThe difference between automation, augmentation, and net new value5 examples from Raul's AI COO, including daily briefings, content production, searchable business memory, relationship research, and quality controlHow AI moves value up the Service Stack toward judgment, transformation, accountability, and beliefThe 4 pricing choices in the New Value QuadrantWhy speed to value is becoming a critical measure for product and fulfillment teams2 reflection questions to help you decide where AI belongs in your businessChapters[00:00] Why I'm sharing this workshop [01:14] Work and grow at the speed of your thoughts [01:24] The goal: own your AI instead of only renting access [01:45] What the workshop will help you decide [02:10] Why I built my own AI COO [03:14] The experience that shaped what I built [03:48] AI sovereignty: data, model, and harness [04:33] Why a good model is just a brilliant stranger [05:17] The restaurant analogy for an AI harness [06:43] The 5 ingredients: agents, skills, hooks, memory, and rules [08:29] Human flourishing and the values inside the system [10:43] Why memory improves the system over time [11:08] Security, compliance, and human approval [12:04] One orchestrator with a team of specialists [14:06] What AI actually makes possible [14:38] Automation, augmentation, and net new value [19:54] Examples from inside my own AI COO [24:28] Quality loops and the chain [26:10] How AI moves value up the Service Stack [28:08] The AI pricing trap [29:40] How service business pricing is already changing [30:21] The 4 choices in the New Value Quadrant [34:46] Speed to value as a new KPI [35:31] Why the advantage window will not stay open forever [36:34] The written workshop and reflection questions [36:49] Question 1: what do you wish you could do but are not doing [38:34] Question 2: where will your business model evolve [39:37] The build manual and additional resourcesReflection Questions1. What do you wish you could do, but are not doing today?Name the bottleneck, opportunity, client outcome, product, or operating improvement you already know deserves attention. Then decide whether it is actually solvable with AI, which data and model it requires, what should live in the harness, and which decisions must stay human.2. Where will your business model evolve, or be forced to change?Review your value proposition, customer segments, channels, customer relationships, revenue structure, costs, and key partners. Look for where AI compresses an input and where that new capacity can create greater value for the people you serve.ResourcesFree Build ManualThe AI Growth Harness Manual: the open sourced architecture to build an owned AI system with your own agentMore on StrategyHow AI Will Evolve the 7 Parts of Your Consulting Business ModelOn Creating Net New ValueThe New Value Quadrant: How to Price in the Agentic EraThe Service Stack: What Remains When AI Eats Client Services
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 Insight02:58 Statistical Knowing05:02 Virtually Unconditioned09:02 Using AI Without Outsourcing Judgment11:39 Formation in Venture Building14:19 Anthropology First Product Design17:56 Hard Rules for Human Flourishing18:53 What Ought We Build21:20 Humility and Idea Flow Playbooks24:19 Probabilistic Products and Implicit Anthropology28:48 AI as Oracle in Education34:29 Cold Storage for Venture IdeasConnect 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 Progress03:29 Diagnosing Change Problems05:22 Nuclear Plant Case Study07:32 Why Playbooks Fail09:58 The Easy Button Trap12:23 Pricing Change Work16:42 Zero Overlap Finding19:37 AI Readiness Gap22:40 Redesigning Change StrategyConnect with Michael: • www.michaeljlopez.coach, IG - @michaeljlopez9, LinkedIn - https://www.linkedin.com/in/michael-j-lopez9/ , X - @MichaelJLopez9Connect 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/