What happens when a 10-year-old SaaS company blows up its roadmap and rebuilds itself around AI—from culture to code?
In this episode, John Waldmann, Founder and CEO of Homebase, shares exactly how and why they did it.
Homebase, a platform serving over 150,000 local businesses, has shifted from traditional development to a radically faster, prototype-driven approach powered by AI. But this isn’t just about new tools—it’s about reshaping the DNA of an entire organization.

We explore how Homebase went from 20-page PRDs to live demos, why John had to reclaim product leadership to drive change, and what it means to push employees—gently or not—into their "oh shit" moment with AI. John opens up about the cultural friction, the leadership reckoning, and the tactical moves that made AI real across the company—from engineering to customer support.
Plus, we zoom out: what does this transformation mean for small businesses, the future of SaaS, and how AI can actually bring teams closer to the humans they serve? Along the way, we dive into the tension between speed and craftsmanship, the underrated power of vertical software, and why inaction might be the most dangerous leadership choice of all.

If you’re navigating an AI shift inside your company—or trying to figure out how to lead your team through one—this conversation is packed with battle-tested insight, hard-earned lessons, and a whole lot of real talk.

Key Takeaways:

• You Can’t Wait for Buy-In—Leadership Means Pushing the Shift — John didn’t wait for excitement or alignment—he took back product leadership and forced the move toward AI. It wasn’t about consensus, it was about momentum. If you’re leading a team through this kind of shift, your job isn’t to ask for permission—it’s to create urgency before it's obvious.
• Speed Over Specs — Prototypes Are the New Strategy — Homebase moved from 20-page PRDs to live demos built in hours. That switch didn’t just make shipping faster—it changed the way teams learn, think, and listen to customers. The takeaway? Stop planning in the abstract. Ship something real, now.
• Culture Is the Real AI Roadblock — The hardest part of going AI-first isn’t tech—it’s trust, fear, and inertia. From engineers to support teams, John had to help people reach their “oh shit” moment with AI. That’s when change sticks. Until then, it’s just optional homework. Leaders need to make adoption inevitable.
• AI Should Bring You Closer to Your Customers, Not Farther — This episode isn’t about chasing shiny tools. It’s about using AI to reduce the noise—so your team can focus more on humans, not less. For John, pragmatic AI is about freeing up time, getting closer to customer problems, and making the org feel smaller, not colder.

LinkedIn: John Waldmann | LinkedIn
Homebase: All-in-one Employee Scheduling, Time Clocks, Payroll, & More | Homebase

00:00 Introduction and Initial Reactions to AI
00:31 Meet John Waldmann and the Story of Homebase
00:53 Reinventing Homebase as an AI-First Company
01:46 From PRDs to Prototypes: Building Faster, Learning Smarter
05:02 How AI Is Reshaping the Customer Experience
09:19 Culture Shock: Resistance, Skepticism, and AI Adoption
14:03 The End of SaaS as We Know It?
19:34 Leading Through Disruption: Ownership, Urgency, and Org Design
25:12 Forcing the Shift: Getting Teams to Embrace AI
27:50 Hiring the Unemployed—and Other Nontraditional Talent Bets
28:56 Curiosity > Credentials: What to Look for in AI-Ready Teams
31:57 New Expectations, OKRs, and Holding Teams Accountable
37:10 Serving Small Businesses Better with AI
44:52 Final Thoughts: Team Dynamics, Founder Risk, and What’s Next

📜 Read the transcript for this episode:

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Show edited by Emma Cecilie Jensen.

In this episode, Joshua Wöhle, co-founder and CEO of Mindstone, shares how AI can go beyond automation to truly augment thinking, strategy, and workflows. He walks us through the personal rituals and frameworks he uses to spot high-leverage opportunities, and why iteration—not speed—is the real unlock.

We explore how non-technical teams can build custom tools without code, why HR is the real AI driver in most orgs, and how the shift from SaaS to tailored internal solutions is reshaping the future of work. Packed with practical insights for anyone ready to move beyond the buzzwords and into real AI-powered productivity.

Key Takeaways:

• AI’s Real Value: Augmentation Over Automation — Joshua explains why the biggest win with AI isn’t cutting tasks—it's using AI to amplify your thinking. If you’re only automating, you’re missing out on AI as a creative and strategic partner.
• Crack the Code on the "Utility Threshold" — AI should save you time or improve outcomes. If it doesn’t, you haven’t hit the utility threshold yet. Joshua shares how to spot when AI becomes truly useful—and how small tweaks can unlock massive gains.
• Why You Should Build, Not Buy (No Coding Needed) — Forget pricey SaaS tools. Joshua reveals how anyone—yes, even non-tech teams—can quickly build custom AI solutions that fit their workflow, saving time, money, and boosting flexibility.
• HR: The Unexpected Hero of AI Adoption — It’s not your CTO driving AI success—it’s HR. Joshua makes the case for why empowering people, not just deploying tech, is key to creating AI-augmented teams that thrive in the future of work.

LinkedIn: Joshua Wöhle | LinkedIn
Mindstone: Mindstone - Empower Your Team with Practical AI Skills

00:00 Introduction to Joshua Wöhle and Mindstone
01:10 Personal Practices for Automation
02:35 Early Wins in AI Automation
11:23 Levels of AI Proficiency
14:59 Utility Threshold in AI
24:51 AI in Organizational Structures
33:21 Introduction to the Early Space and AI Integration
33:45 Joshua's Entrepreneurial Journey and AI Augmentation
34:37 Challenges and Breakthroughs with AI
35:32 The Evolution of Building with Generative AI
37:56 The Future of SaaS and Internal Development
40:34 Practical Examples of AI Implementation
50:14 The Importance of Iteration and High-Value Tasks
54:56 Concluding Thoughts and Reflections

📜 Read the transcript for this episode: Transcript of Why HR not CTOs Will Lead AI Augmentation - with Joshua Wöhle |

For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:

Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley

Show edited by Emma Cecilie Jensen.

In this episode, Nicholas Thompson, CEO of The Atlantic, shares a personal and expansive look at how AI is reshaping creativity, leadership, and human connection. From using ChatGPT in marathon training to rethinking journalism in the age of agents, Nicholas explores AI not just as a tool—but as a thought partner.

We dive into cognitive offloading vs. augmentation, the ethics of AI-generated content, and why preserving “unwired” intelligence still matters. He also reflects on leading through disruption, building analog habits, and fostering team-wide experimentation. A rich conversation on staying human in an increasingly automated world.

Key Takeaways:

• Your “unwired” intelligence is your AI superpower — The more human skills you build—like deep focus, emotional presence, and analog thinking—the better you’ll be at wielding AI. Thompson argues that cultivating these unwired abilities isn’t just about staying grounded—it’s about unlocking the full potential of the tools.
• Don’t fight the storm—gear up and adapt — AI is already transforming media and creative industries. Thompson compares it to a coming storm: you can’t stop it by yelling at the clouds. Instead, embrace it, understand it deeply, and make strategic decisions based on where it’s heading.
• Leadership means showing, not just telling — As a CEO navigating disruption, Thompson doesn’t just advocate for AI exploration—he models it. From training staff on GPTs to walking the halls and testing ideas live, he treats leadership as a practice of visible experimentation and continuous learning.
• AI relationships can’t replace real connection—but they can confuse it — Whether it's logging meals with a bot or losing a personalized Enneagram coach to a reset, Thompson highlights the emotional pull of AI and the dangers of relying on digital companions over human ones. Staying socially connected, especially through “third spaces,” is more important than ever.

LinkedIn: Nicholas Thompson | LinkedIn
The Atlantic: World Edition - The Atlantic
Website: Home - Nicholas Thompson
X: nxthompson (@nxthompson)
Strava: Cycling & Biking App - Tracker, Trails, Training & More | Strava
Caitlin Flanagan – Sex Without Women: Article:SexWithoutWomen-TheAtlantic

00:00 Introduction to Nicholas Thompson
00:11 Navigating the Information Overload
01:10 Daily Tech Insights and Tools
02:10 Using AI for Content Creation
04:39 AI as a Personal Trainer
08:02 Emotional Connections with AI
12:12 The Risks of AI Relationships
16:17 Preparing for AGI and Cognitive Offloading
30:26 AI's Impact on Leadership
31:10 Navigating AI Competitors
32:01 Internal AI Strategies
32:49 Ethical Considerations in AI Usage
34:07 AI in Journalism and Writing
36:32 Practical AI Applications
40:27 Balancing AI and Human Skills
49:27 Future of AI in Media
53:50 Final Thoughts and Reflections

📜 Read the transcript for this episode: Transcript of What AI Can't Replace – How The Atlantic Deals with Disruption |

For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:

Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley

Show edited by Emma Cecilie Jensen.