In this episode, I talked with Keith Jacobs, CEO of geniant, and Grant Baldwin, Partner at geniant, about why most AI investments never show up on the P&L, and what the small group of companies making real money on AI actually does differently. Grant walks through a McKinsey study of 1,700 companies where only 6% are making real money on AI, and Keith and Grant make the case that what sets that 6% apart is redesigning how the work gets done instead of automating a broken process, what Keith calls paving the cow path. We get into why geniant puts anthropologists and psychologists to work before its designers start building with AI, the Olympic level of performance employees will need once the busy work disappears, and why leadership has to clear the path from the top or AI initiatives slow down considerably. We also run a thought experiment on the future of software, closing the context gap until every piece of software is custom to the person using it, and talk about who should own your data and why an opt-in model matters.

Chapters:

• 00:00 The Olympian Worker
• 02:35 Performing at a Higher Level
• 06:46 Building the Right Thing
• 09:51 The 6% Making Real Money
• 11:53 Paving the Cow Path
• 15:52 Scared to Admit Using AI
• 17:54 Air Cover From the Top
• 20:49 A Behavior First Operating Model
• 22:46 Staying Optimistic About the Risk
• 24:45 100 Times More Capable
• 27:23 Closing the Context Gap
• 30:48 Who Should Own Your Data
• 33:19 Every Employee Owns Equity
• 36:38 Thinking Like a CEO

Connect with Keith & Grant:

• geniant
• geniant on LinkedIn
• Keith Jacobs on LinkedIn

Connect with Raul:

• Work with Raul
• Free Growth Resources
• Connect with Raul on LinkedIn (DMs open)

In this episode, I talked with Garrick Van Buren about pricing as value creation and why every price is really set against the status quo of “doing nothing,” meaning you must outcompete the comfort of not fixing a problem. We break down value as transformation from current to future state and how to quantify it through revenue gains, cost savings, time savings, and especially retention/churn, with examples like a real estate brokerage commission tool where agent retention drove the true value. Garrick shares his “value stack,” customer rediscovery interviews to uncover unpriced value and unmet needs, and a “How’s My Driving” approach to re-segment customers and refine positioning. We also discuss AI, speed-to-value premiums, services vs product tradeoffs, incremental pricing rollouts, and why founders must remove their own money emotions from pricing using metrics like percentage of annual revenue and risk mitigation.

00:00 Pricing Against Status Quo

04:34 Quantifying Value Shifts

06:24 Revenue Retention and Churn

08:35 The Value Stack Framework

09:59 Real Estate CFO Case Study

14:17 Net New Value With AI

17:52 Customer Rediscovery Calls

19:56 Unpriced Value and Missing Offers

21:31 Services Strategy and Time to Value

23:21 AI as New KPI

24:41 Niching and Positioning

25:01 Customer Rediscovery Buckets

27:03 Pricing Power Signals

29:18 Incremental Price Rollouts

33:02 AI Discounts Debate

34:26 Speed to Value Premium

39:23 Jobs to Be Done Lens

42:28 Detach Emotions from Pricing

45:40 Risk Transfer and Credibility

Connect with Garrick:

• https://forstarters.substack.com

• https://linkedin.com/in/garrickvanburen

• https://pricingfromthestart.com

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 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 Shifts

02:18 Early Hiring and Survival

06:24 Finding Meaning in Work

10:25 Planning Beyond Survival

13:10 Belief and Big Bets

14:42 Stewardship and Scaling

20:04 Separating Identity from Business

22:08 Is Growth Always Right

26:46 Leading in the Tension

30:06 Human Flourishing Thesis

34:01 Fixing Sick Care at Scale

39:14 Human Dignity in Healthcare

42:49 Defining a Human Soul

Connect with Phillip:

• Northwind https://www.northwindhealth.com

Personal website: https://www.phillipberry.com

phil.berry@northwindhealth.com

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/